phtlc
Super-Earth
- Joined
- Jun 11, 2009
Dinner Date
The game was tight, but we beat them. While I was not the top player on the team (although I was an OK player), this was definitely my best game. Looking out at the stands she was there. Her name was Helen, or Ms. Caldwell as she called herself. She was so hot, I always checked her out. She was in her 30’s and had a fucking amazing body. She looked so sexy in her business suit, and I couldn’t help but wonder what she was doing at the game. She smiled at me when people cheered my performance, and it made me rubbery legged. She was always so sweet to me, but I know she just thinks of me as a boy and nothing more. I on the other hand, had harboured a massive crush on her since I was in training wheels. Now as a teen, I felt like I should come across as more mature, however the fact remained, that while I was working out and it was starting to show, I still had a teens body, not a man’s body. I didn’t shave yet, and had no hair on my chest.
As I made my way off the field, I started putting my equipment in my bag, I said goodbye to my team mates and coach and started heading home.
‘Hey Rick, Great game!”
Her voice....my legs went rubbery
“oh hi...uh...uhm yeah I think....” fuck I sounded like an awkward shy boy, “Uhm yeah, thank you Ms. Caldwell....I am glad you liked it”. Fuck I sounded like a kid!
Smiling at me, as though trying to be understanding about my awkwardness she walked up to me.
“Heading home? I’ll walk with you”, she said as her hips wiggled hotly while she walked in her heels.
“OK, sure!” I cringed at how excited I sounded when I said that.
She walked home with me, talking away with me as we went. I was so excited at the opportunity to walk with her that I could feel my heart speed up.
“Play any other sports at your school?” She asked with genuine interest
“Uhm....well not right now, this is the only sport this season. I am planning on joining the wrestling team though” This was a lie. I had no interest, but I figured it would sound macho. She smiled her approval.
She made small talk for the duration of our walk, and I did my best to engage in conversation with her, while trying to sound mature. As we walked, I did everything I could to try to stick my chest out, without making it look like I was sticking my chest out. I was in very good shape, but I still had a teen body, rather than a man’s body, which made me feel shy around her. Helen on the other hand definitely had a woman’s body. She had curvaceous hips, a small waist and perfectly sized breasts for her body size. The way her body moved as she walked, combined with the click of her heels was soooooo fucking hot it was driving me insane. I sincerely hoped she couldn’t tell what I was thinking of her. As a grown adult, if she had any idea of the sexual thoughts going through my mind, she would have been highly offended and unimpressed with me.
The whole time we talked, she seemed genuinely interested in what I had to say, which was flattering to me. Don’t get me wrong, I was no geek, but I was definitely shy around girls, and was still a virgin. Most of my friends were too, but we all lied and made up stories of having scored despite the fact that we had only scored with our hands. We were still young, so time would change that.
Eventually she got around to asking if I had a girlfriend. I didn’t have anyone serious. I had fooled around with one girl, and managed to feel her breasts through her bra, but that was about it. I had kissed a couple of girls, but only managed to fondle the one. Most of my friends had gone a bit further than that. My problem was not my looks, but the fact that I was shy.
“Uh...uhm well nothing that’s....serious you know” I said awkwardly
“No need to rush into anything serious, you’re still young” she said reassuringly. I couldn’t tell if she was giving advice or just patronizing me out of sympathy. As if reading my thoughts, she spoke again.
“You’ll do fine when the time comes...you’re a very good looking guy. There are plenty of girls who would like to be with you”, she said with a genuine smile and sincerity. This made my heart speed up with excitement. Ms. Caldwell had called me good looking!!!!
“Uh..thank you” I said, trying not to sound too excited or boyish. I’m not sure how good of a job I did.
As we approached her house, more than a block before mine, I prepared to say goodbye to her when she spoke
“Rick, are you in a hurry? I have some things I need brought down to my basement, and I could use a strong guy to do some lifting. I would really appreciate your help” She asked.
‘Sure!” I said, and immediately cringed at how enthusiastic I sounded. That must have sounded like a dead giveaway. “I mean...I don’t mind helping”, feeling even more flustered at my pathetic attempt at recovering.
‘Oh excellent, thank you!” She said with a smile, “I’ll make it worth your while” she said.
I certainly knew how I would like her to make it worth my while, but that was obviously not what she meant by that.
I followed her up to her door, checking her out from behind as her heels clicked on the walkway. My mind was abound with fantasies of her jumping me when we got inside, but that stuff was the product of Penthouse forum stories, and not reality. She was fucking hot, and dated men, not boys, but still the fantasy was there.
“OK, those boxes over there need to go in the basement, and those three in the separate pile need to go upstairs.” She said, “Thanks again for doing this Rick”
“No problem Ms. Caldwell”
“Call me Helen”, she said sweetly. Holy shit!
“OK... Helen”, fuck, I could feel I was blushing.
Walking over to the first box, I grabbed onto it and realized it was quite heavy. I was determined however to look as manly as possible, so I lifted while trying to maintain a facial expression that showed total relaxation. She smiled approvingly as I lifted. I did everything in my power to flex my muscles, without making it obvious I was doing so.
Heading downstairs, I carried the first box, following her as she showed me where it was going. It was quite heavy, so I was relieved when we finally got there, but again I made a point of acting like it was easy to carry.
“Looks like you are managing just fine” she said with a smile.
I spent the next little while, lifting boxes, carrying them downstairs, always trying to puff out my chest, and flex my biceps. It felt incredible to be doing manly work in front of Helen, as she watched. I tried to imagine that she was getting turned on by this, but again this was just fantasy.
When I finished with the boxes going downstairs, I approached her to find out where the other boxes were going.
“Grab the box with the yellow tape on it and come with me”, she said walking toward the stairs. I followed, and as we ascended the stairs, I couldn’t help but stair at the bottom of her skirt, as from this angle I could get a better view. I still couldn’t see her panties or anything but the look of her lower thighs from behind was a sight for a young guy like me.
“You managing that OK?” she asked, as I looked up rapidly to see her looking back at me. I hoped to fuck she didn’t see me checking her out. ‘Please...tell me she didn’t bust me!’ I thought.
She smiled sweetly, and guided me to her den and showed me where the box went. I went to get the other box, as she waited for me. As I walked towards the den, she stepped out and instructed me to follow her as she guided me into....her bedroom! Holy shit! I’m in Helen Caldwell’s bedroom! I thought. Many fantasies had placed me in this room.
“OK, just put it over there young man” she said with a cheerful tone as I caught her smiling at me, mostly sweetly, but partly with a faint sense of amusement. I couldn’t help but wonder if my expression had tipped her off as to what I was thinking. I was blushing again.
Heading downstairs, I grabbed the other box and carried it upstairs to the hot looking goddess’s bedroom. I didn’t hurry too much when I got there. I was not likely to ever be in her bedroom again, so I figured I might as well make it last. Putting down the box, I made sure to posture myself well, but again not to be too obvious.
Standing, I looked at her. ‘So...uhm....is that..uh..it?”, I shifted awkwardly.
“Yup, that’s all. Good thing I ran into you. I never could have lifted those boxes” she said. Reaching out she put her hand on my bicep.
“For strong guy like you, I’m sure it was no problem” she said. My knees just about buckled!
‘Uhm...ahem uh yeah, it was no problem” I said, trying to seem manly. Fuck I felt awkward. I hoped she wasn’t patronizing me. I worked out, and had biceps, but it was still boyish muscle and not the beefy hard manly muscle.
“Come on downstairs. Let me make you something to eat” she said, heading out of the room.
“OK” I said, wishing we could stay in the room.
Heading downstairs, I went to her kitchen and sat down as she prepared some food. I still couldn’t believe I was here, and now going to eat with her.
“Do you want something to drink? After hard work a man could probably use a cold beer”
Holy fuck!!! She just called me a man!...and offered me a beer!!!!
“Sure please!” I said, trying to control myself.
She reached into the fridge and pulled out a cold bottle, twisting the top off and handing it to me. I raised the bottle to my mouth and took a swig, trying to look natural. I really wasn’t a very experienced drinker. There was no way I would be able to go to a beer store without getting carded. My friend’s older brother had fake ID and could get beer, but he rarely ever got any for us.
She started preparing a tray with various cheeses, spreads and meats, with some crackers and other assorted items.
“Let’s go down to the recreation room in the basement”, she said wistfully. Following her, I walked into the darkened interior of the basement, which had a combination of rustic and postmodern design. The floor was stonework, with a marble top coffee table. It all looked very expensive, and she must have paid quite a fair amount of money to get this. The couch was nice leather and there was an exotic looking recliner.
‘Sit there” she said, gesturing to the couch.
I sat quickly, almost obediently. She placed the platter down in front of me. It looked amazing.
“Go ahead, eat” she said encouragingly. I leaned forward and grabbed a cracker and cut some cheese, placing it on the cracker. Let me tell you, this was the most amazing cheese I had ever tasted. I started sampling the wares, overwhelmed by the kaleidoscope of flavours I was experiencing. The cheeses, the meats, and other treats were all so good, I found myself pigging out and immediately felt self conscious.
“Are you having any?” I asked, gesturing to the tray
“Not now, but you go ahead. I have plenty more” she said as she walked over to a door off to the right. She emerged with a bottle of red wine, and opened it, grabbing some glasses. Walking back towards me she sat down and poured herself a glass. Then she went to pour me some and paused.
“I could get you another beer instead?” she asked, gesturing towards my near empty bottle. My first thought was to get another beer, but then wine seemed more to set a romantic tone.
“Wine would be nice” I said, trying to sound cool and relaxed. It may be nothing, but sitting in Helens nicely finished basement, having wine and cheese as we sit on the same couch. I was getting as horny as hell.
She handed me a glass and raised hers gesturing to me to do the same. Raising mine, I allowed it to clink lightly against hers and then took it to my mouth and took a swig. I almost immediately gagged...it was not cold. It was almost warm. I tried to hide the grimace.
‘Everything OK?” she asked
“Uhm, it’s fine, I guess it’s just that it’s not chilled”
“Oh you don’t chill red wine dear, just white wine”. DOH! I must have looked like an idiot.
“I can get you another beer?” she offered.
“No, this is fine thanks” as I took a small careful sip. I wanted to try to appear as mature and sophisticated as possible. She seemed to smile reassuringly. Did she realize how hard I was trying to impress her. We made small talk for awhile, and she seemed very friendly. When I said something that made her laugh, she sort of slapped my chest playfully. She may have just been being friendly, but to be a teenage boy, having a hot looking mature lady like her making any physical contact caused an instant hardon. I shifted uncomfortably, trying to position myself so she wouldn’t see it. As we talked some more, she seemed to be leaning in, getting herself very close to me, really maintaining eye contact. At one point she reached out and swept some crumbs off my shirt. My mind was going crazy, imagining that she was flirting with me. Part of me, the realistic part of me dismissed that as silly. I was a boy, and there was no way a hottie like her would choose a boy when she could have any man. I was still getting as horny as hell!
As we talked she was leaning forward, and I was getting a half decent (but not perfect) view of her cleavage. As I looked through the top of her blouse, she leaned ever so slightly forward as I strained my eyes to catch a glimpse.
I caught her looking down as though wondering what I was looking at and immediately brought my eyes up, hoping she didn’t bust me. She responded by sitting up a bit straighter, so I wouldn’t have as good of a view. I blushed, knowing deep down that I had been busted. At least she didn’t confront me on it. I would have just died of she did that.
As we talked, she brought her feet up onto the couch, and I was aware of the fact that I had a half decent view up her skirt now. I couldn’t tell because I was determined not to look directly. I didn’t want to push my luck and piss her off. The problem was, she was sort of sitting with her legs curled up beside her as she sat with her side against the back of the couch, facing me. As a result, every time she shifted a bit, the opening between her knees in her skirt tempted me. It was a game of willpower for me to not look up her skirt. Eventually I slipped and reflectively cast a glance at a view of her inner thighs, but did not get a look at her panties. She smiled at me, and I felt myself blush more. Did she catch that one? It was less than a second and she was reaching for her wine. Fuck, please tell me she didn’t catch me looking up her skirt. PLEASE!
We talked some more, her filling my glass of wine again, as I continued to drink it, trying to be all sophisticated. The truth was, I just wasn’t much a wine person I guess, but there was no way I was letting her know that.
Eventually the topic of a school dance came up. She had heard one of the girls in the stand talking about it.
“Are you taking some lucky girl to the dance?”
What a terrible question. I didn’t have a date, and didn’t have the nerve to ask a girl to the dance. The last school dance I went to, I stood there most of the time with my friends, and only in the last twenty minutes did I end up dancing with a girl. She had liked me, and I had liked her, but I stood there like an idiot most of the night until my friends practically told the two of us to dance. I had no idea what I was doing.
‘Uhm, not really...I guess I wasn’t sure if I was going to go”, I answered a bit embarrassed.
“Not going to go?” she said with alarm. “Rick, you only get to be young once. Don’t live with regret for the things you didn’t do!”
“Well, uh..I don’t really have a date, and uh......”, I flustered
“So if you don’t have a date that means you can dance with several young ladies. Think of it as an opportunity” she said with encouragement.
“Well, I guess I’m just....well I’m not a good dancer”, I admitted.
“Rick, you just have to relax and go with it. Besides, you can always do the slow dances. Those ones are nicer anyway” she said.
“I guess, but I don’t really know how to dance formal slow dances”, I admitted
“And most high schoolers don’t know how. Haven’t you seen them. The guy just put’s his arms around the girls waist and she puts hers around his neck, and they simply rotate slowly in a circle.”, she said with a bit of a laugh. She was right actually, that’s all they seemed to do.
Slapping me on the thigh, missing my erection by an inch, she stood.
“Come on, I’ll show you” she said, holding her hand out to me. I really didn’t want to stand, since my boner would be much more visible. Had her slap been an inch off I would have been busted. Fuck she was hot! Why couldn’t I make this stupid erection go away?!
“Come on, take my hand” she said gesturing.
Reluctantly, I reached out and took it and she pulled gently. I stood, moving awkwardly, trying to keep my hands low in front of me to cover my erection, but not be obvious that I was hiding something.
She reached out, and put her arms around my neck, and moved in close.
“Put your arms around my waist”, she instructed. I did this awkwardly, unable to believe I was now in such an intimate position with Helen.
“Now we just slowly go in circles, making small steps...anybody can do it” she said. I followed her instructions, and tried to look like I was calm and relaxed, when I was as excited as hell. Helen and I were standing face to face, dancing in a romantic kind of way, alone in her basement. Holy shit! If my friends could just see me now!
As we danced, she started moving in closer as she gave minor instructions and encouragements. I was worried, because if she pressed up against me she would feel my erection, and I was terrified about her spotting that. I tried to keep my hips back, so she would not brush up against it, but she told me to straighten up, while smiling encouragingly, telling me I was doing fine.
Suddenly without warning, she moved her hips forward a bit, and before I could even react her thigh brushed against it and I knew right away that she felt it. She immediately paused, and stepped back.
“Uh-oh, what is this?” she said in a serious tone. I tried to twist away but she stopped me, and looked down. I could feel my face blushing insanely, and wanted to just disappear. She was being nice to me and I was just getting horny.
Looking at me with an accusing look, she asked me in a stern tone
“Would you care to explain yourself Rick?”
Holy shit this was horrible. She was a grown woman and I was caught getting all horny over her. Shit! Would I be in trouble? Would she say something to my parents? Fuck I was so embarrassed.
“Rick?” she asked, questioningly. I was staring down, fumbling for words
“Rick, look at me when you talk to me”. I looked up, horribly embarrassed, with an apologetic look on my face, as I fumbled for words. I wished I could just die at that moment.
She looked at me hard for another few seconds, then a huge smirk broke out on her face and she let out a burst of laughter.
“Relax, I’m just giving you a hard time. That’s perfectly normal for a guy your age. I should have been more careful. Any of your classmates would have had the same reaction, so don’t feel embarrassed”, she said with a reassuring smile, touching my face.
I was still having a hard time talking, as my face glowed.
“Oh, I’m sorry” she said mirthfully, “ I was just having a bit of fun with you...I shouldn’t have teased you like that” as she touched my cheek tenderly.
“Come on, let’s get you seated down so you will be able to relax” she said, taking my hand and guiding me to the couch.
“Rick, I’m not upset OK. I’m flattered to be honest, a handsome young guy like you finding a lady my age attractive” she said with a flashing smile.
‘Her age’ I thought? She was in her early 30’s not her fucking 60’s for crying out loud. And she obviously worked out regularly and watched her diet. Besides her face was very smooth, with no wrinkles.
Sitting down, I tried to relax as she sat beside me, facing me on the couch.
“Here, have some more wine” she said. This time I took a huge swig, trying to get my heart to stop pounding.
“Have some snacks, they’ll help you relax” she said as she grabbed a cracker, and spread some sort of hot jelly on it for me.
“Here, you haven’t tried this one yet” she said, holding it out to me as I took it from her and held it to my mouth, taking a bite. She was immediately preparing another smaller cracker for me, this time with some sort of meat spread. The cracker I was eating was overloaded and I got the jelly all over my fingers as I ate. She held the other one up and as I reached for it, she shook her head.
“No, you have that pepper jelly all over your fingers...here, just open your mouth” she said as she held the cracker to my face. Oh my god! I opened my mouth, and tried to take the cracker from her fingers, but as she pushed it in, her fingers went too far and her finger flicked my tongue. It was the most erotic thing I had ever experienced in my young life.
She smiled, and as I looked around for a tissue for my sticky fingers, she took my hand and brought it close to her.
“Here, let’s not let this go to waste”, and she took one of her own fingers and used it to wipe the jelly off of the finger that had the least jelly on it. With that, she raised her finger to her mouth and licked it off. I could feel some wetness inside my pants, and my boner was screaming and twitching for release.
Then she took the next finger and raised it directly to her mouth, and stuck out her tongue and started licking the jelly off of my finger. Holy fuck, I realize she was just licking my finger, but this was so fucking hot I couldn’t believe it! Smiling, she took the last finger, and raising it to her mouth she stuck it in her mouth and started sucking the jelly off, her tongue swirling around my finger as she sucked. I could barely breathe, and realized my mouth was hanging open. My finger was still in her mouth when she looked at me deviously as she took it out, and she leaned forward. Touching her hand to my thigh, she spoke;
“Oh yes, I’m very flattered” she said as her hand slid towards my erection, gliding over the material covering it, as my erection jumped and twitched.
“I was trying to get you going from the start” she said with a smile, “ I just enjoyed the suspense, but I can’t torture you forever..............besides I want to have you right now”, she said, leaning way forward, starting to climb on top of me.
WHAT THE FUCK!? Was I dreaming? My mouth was wide open as she moved over me and leaned in to kiss me. The suddenness of her turnaround hit me like a train.
“Nervous? I don’t bite” she said, responding to the fact that I was frozen. Her lips touched mine and I felt a jolt go through me at the contact. I was on a couch, making out with the hottest looking lady in town. She leaned into me, her body pressing against mine as her tongue probed my mouth.
Breaking the kiss she spoke, “Relax, you’re so tense, and you’re not breathing”
I did my best to relax, but I was overwhelmed with the moment. It was hot, yet I was nervous as hell. I had no experience! I had kissed another girl at the school, and had felt her a bit, outside her clothes, but I had never had sex! I didn’t know what to do! I hadn’t even seen or touched a girls pussy! Hell I hadn’t touched a girls tits except through her clothes.
The feel of her warm body pressed against mine had me twitching with excitement, as I felt slight moisture inside my underwear. We kissed for several more minutes, her on top of me as I leaned back in the couch, feeling her slender body pressing down on mine. I was so horny it was killing me. Our hands roamed over each other’s bodies, as I stroked her back, and her sides. I wanted to bring my hands around front and feel her breasts but was not sure if she would mind.
As if reading my mind she spoke, “Rick, you can let your hands explore...I’m pretty sure I know where you want to put them” she said encouragingly. I didn’t need to be told twice, and immediately brought my hands to her breasts, feeling them through her shirt.
“Let me help you” she said, moving my hands away as she sat up, straddling me. She gently brought her hands up to her blouse and started undoing the buttons very slowly, smiling seductively the whole time as I stared at her opening cleavage like a deer in the headlights. As her shirt fell open, she reached forward and undid her bra which was one of those front opening ones. Falling out of the opening bra was the most beautiful set of tits in the world; not exceptionally big, but so well formed and tender looking!
Tentatively, I reached foreward, placing my palms on them and as soon as my skin made contact with them, I almost gasped from excitement at the feel of these soft yet formed orbs in my hands as I massaged them, playing with them getting lost in the excitement of them. I squeezed them, stroked them, felt the nipples.
“Don’t forget that the rest of me is still here Rick?” she said jokingly.
She took my hands and pulled them away, pushing them back so they were beside my shoulders. Then she leaned forward, riding a bit and brought those amazing tits close to my face so I could access them with my mouth. My head was spinning with excitement. I had the hottest lady in the neighbourhood sticking her tits in my face!
Opening my mouth, I tentatively took a nipple into it and closed my lips upon it, running my tongue over it.
“Ooooohh, Rick, you have no idea how good that feels” she purred as she started grinding her body on top of mine. I was almost spinning with ecstasy, as her body pressed down on me, her crotch grinding into mine as I sucked on her nipple. She took my head in her two hands and started grinding her tits up against my face, allowing me to suck on them one at a time. The sensations through my body, in my groin were overwhelming me, almost as though about to cause me a short circuit.
“Oh my god Rick, this is getting me so hot!” she purred sensuously as her crotch ground against me. ‘getting her so hot?’ I mused. I could feel the heat from her pussy radiating through the thin material of her panties, and then through my pants against my straining cock. I started grinding my hips upwards to meet her grinding as I continued sucking on her tits.
Her hands started aggressively going under my shirt, yanking it up over my head so aggressively she caused a small rip. She was almost attacking me sexually, as though starving for sex (which was perfectly fine by me), but it seemed so weird for such a hot looking woman. I mean, there’s nothing wrong with me or anything, but I’m just an average teen, yet she was attacking me like I was some sort of sex god. I wasn’t about to argue
“Let’s get these off of you there young man” she said as she started undoing my pants. I sort of nodded, and tried to speak, but instead fumbled my words. She barely noticed as she started yanking and tugging on the pants as I raised my butt off the couch to allow her to remove them. She got them off in no time, taking my underwear with them. Shortly thereafter she removed her own remaining clothing and before I knew it I was naked with the hottest looking lady in our entire town!
Sitting there naked on the couch with her, I was exploding with hormones! My cock was straining to the point of exploding as I took in the softness of her flesh and her feminine scent! Just the smell of her was driving me crazy. Oh my god I wanted her. Closing my eyes, I breathed in, taking in her perfume, as I felt her soft skin against mine. The whole experience was driving me wild with arousal.
Her hands ran over my body, feeling my chest as I sat there, kind of wishing I had at least a bit of hair on my chest. As she ran a hand over my arm, I made a conscious effort to tense my bicep, without making it obvious I was doing so.
“Oh, I love your hot young body” she purred as she gently traced her hand down my navel. Her hand moved towards my cock, and when it touched me I almost gasped from the sensation. She wrapped her soft hand around my cock, and started gently stroking it up and down as I tried to control my breathing.
My hands were roaming over her body, feeling her breasts, and her ass. I started tentatively moving my hand between her legs, gently bringing it up her inner thigh, not sure if I had permission to touch her pussy. She quickly reached down and grabbed my hand, and pulled it to her pussy. When my finger touched her soft flesh, I was almost out of control with excitement. I was touching a girl’s pussy for the first time! I had always wondered what one would actually feel like, and now that I was touching one I wasn’t disappointed. I started exploring, feeling the flesh, and probing inside of her as she squirmed against my body, stroking my cock.
I explored her a little further, seeking out her clitoris. I had never seen one, but had an idea where it would be. I found a soft little bump, just forward of her opening and stroked it gently. She immediately gasped and tensed up over me as she kissed me hard on the mouth.
“Oh Rick, you make me feel so good” She said in a husky voice. “Do you want to do something for me; to make me feel real good?” she asked seductively. I could barely speak, and just nodded my head dumbly.
She pushed me down on the couch, so I was laying on my back, and then she lay down on top of me naked, as I felt the heat from her pussy inches from my throbbing cock. She kissed my hard, squirming her body on top of mine, then started moving forward, bring first her neck close to my mouth, and then her breasts as she moved foreward more. Her body moved up even more as her belly was touching my mouth. I kissed and licked it, hoping it felt good for her. As she moved her body forward more, it became evident she wanted to put her pussy up to my mouth, so I could eat her. I was both excited and nervous at the same time. On one hand, placing ones mouth on another genitals seems a bit weird, yet apparently many guys like doing that with a woman. Would it taste bad? Would it taste good. My questions were quickly answered as she straddled my face, pushing her pussy up against my mouth. The scent was strong, but not at all bad. She seemed eager for me to get started, and literally ground her pussy against my mouth.
“Oh be a good boy, and use your tongue on me. Put it in there sweetheart...oh god I want you to eat me” she said, riding my face. I stuck my tongue out, and pushed it between her folds making her almost jump. I pushed further, seeing how far I could push my tongue into her depths, as I felt her internal muscles, contracting around my tongue.
“You don’t have to push deep sweetheart. Less is more. Be gentle, and gradually work closer to my clitoris, but don’t lick it directly, at least not right away”
Complying with her instructions, I worked on her pussy as she rode my face like it was a horse. It felt a little one sided, but I was still thrilled to have my face between her legs like this. Oh my god, if my friends could just see me now. I was with a woman I had fantasized about for years, but never imagined I would actually touch......and I had already gone father with her than I had with any girl at my school.
I worked my tongue closer and closer to her clitoris with each stroke, as her body undulated erotically as though dancing over my face. My cock was straining with excitement, pre-cum dripping out of the end. Her taste in my mouth was such an erotic experience.
“Ok now start lightly licking the clitoris....delicately, like a feather”
Complying, I started flicking it and she immediately squealed, grinding herself down on my face. “Oh, I want to just keep you here forever....such a sweet boy, so hot!”
The whole ‘sweet boy’ thing didn’t sit well with me as I wanted her to see me as a man, but with the hottest looking cougar/MILF sticking her pussy in my young teenage face I was not about to start correcting her. So long as she was sexing me up like this she could call me anything she wanted.
“Oh faster Rick.....start putting more pressure” she moaned heatedly as she started moving her hips faster over my face, swaying her body as her perfect beautiful breasts swayed with the motion of her body. I complied, licking faster and harder, making this hot looking lady squeal and moan as she rode my face like a bucking bronco.
“Oh yes...suck my clit into your mouth,”
Complying I sucked the little nub into my mouth, sucking hard as she squealed and ground her crotch into my face.
“Oh yes Rick! Suck on at and use your tongue at the same time!”
I did exactly that and it pushed her right over the edge as she tensed up on top of my face, emitting a squealing moan of ecstasy as he body quivered over me with her delicious pussy on my mouth. Her orgasm held for another moment or two until she stopped trembling and twitching, and then relaxed, breathing heavily.
Crawling off of my face she smiled, while laying down on top of me; she started kissing my neck as I savoured the sensation. She started gradually working her way down my body, kissing my chest, my abdomen....and eventually she was down, kneeling forward looking at my straining cock. I was tense with excitement as she breathed on my erection, her warm moist breath teasing the sensitive organ as I lay there trying to control my breathing.
She leaned forward and kissed it, causing me to gasp from the sensation. It may seem pretty ordinary to you, but for a young virgin my age, with the hottest looking lady on the block, that kiss on the dick was heaven.
She started gently moving her lips along the hardened flesh, breathing on it, barely touching it as I strained. She worked her way from the base, up to the tip, and then back down to the base. Then she touched her tongue to the base, making my cock jump with excitement. She tenderly ran her tongue along the shaft as I lay there gasping, my fists clenched. She kept this up for several minutes, driving me crazy until she brought her mouth up to the tip, and then very gently, she opened her mouth, and closed it over the head of my cock as I arched my back from the sensation. I could see her eyes looking at me mischievously as she held it gently there in her mouth. Then I just about jumped again, when her tongue touched the opening at the end while my head was in her mouth. She was lightly sucking on the head as her tongue teased the opening at the end of my cock. I was straining, and then as if things couldn’t get more intense, she started taking more of my cock into her mouth, while maintaining eye contact, a smile evident in her eyes. She could see what this was doing to me and she liked it.
As she started taking more in, I felt as though I was about to come soon.
“Ms. Cald.....I mean Helen, I think I’m going to...”
She pulled her mouth away, “You’re going to come?” she asked smiling.
“Let’s see if we can make this last” she said smiling, as she went to work. She would work on me, turning up the pressure, taking my cock in her mouth, until I was about to come, and then she would release it and go back to teasing it. She knew exactly what she was doing. At one point she had my entire cock in her mouth, with the head right at the back of her throat as she worked her tongue over the shaft. This kept up for several minutes, then as she was teasing the head again, while running her tongue over the hole, she grabbed my balls and started gently squeezing them as I delighted in the sensation. I suddenly felt my orgasm coming as she worked my balls and my shaft.
‘I’m going to......come.” I said in warning, but she ignored it and kept working me, until suddenly I exploded in her mouth. She suddenly sucked hard in the end of my cock as she squeezed my balls, which were now pimping semen right into her mouth. She was swallowing vigorously as I climaxed, still working me like an expert.
When I finished, and she milked the last drop out of me, swallowing it eagerly, she released my cock and balls, then looked at me.
“I had to get that out of the way. I don’t want you to have a hair trigger when we take this to the next level”
Next level! No way!
She crawled back up smothering me with kisses, molesting me with her hands as I did the same. I still couldn’t believe, that a shy young inexperienced teen like me had her soft skin up against me, ....and that I had just came in her mouth! Holy shit!.
“Looks like you enjoyed that sweetheart!” she said tenderly. She started rubbing herself all over me, and playing with me. Suddenly she lay back and pulled me towards her. So I lay on top of her. Holy shit I was about to have sex with her! I kissed her passionately, as I tried to get between her legs, but she started squirming, pushing on my shoulders, making me move down her body. I suddenly realized she wanted me to go down on her again. I was partly disappointed, because I really wanted to have sex with her, but I figured I could wait. I would eat her pussy for ten hours straight if that’s what I had to do to get to have sex with her.
Moving rapidly down her abdomen, I started kissing her flesh as I went.
“Oooohh....Rick, you know what a lady wants don’t you” she stated excitedly. I felt immediately flattered and was determined to give her the best oral sex she had ever had. Or at least I would try!
Moving my face down to her tender looking pussy, all I could think about was how that would feel around my cock. Fuck I wanted to have sex with her. I was dying.
As soon as my tongue touched her flesh, her body quivered and she arched her back, while spreading her legs wider. I went to work with considerable zeal. She had been the object of my fantasies for years. Many a nights had been spent masturbating while fantasizing about this scenario, but I never truly imagined it could happen for real.
I licked and sucked her clitoris as she squealed, and ground her pelvis up into my face. Her legs thrashed around, her abdomen fluttered and she literally squealed in delight as I ate her. Soon she started getting more excited and reached down with both hands, grabbing my hair and grinding my face into her crotch as she literally thrust her hips up, as though fucking my face until she suddenly seized up, quivering as she cried out in heated moans, her thighs clamping tightly on the sides of my head, her hand still pushing my face into her pussy for several more seconds until her body relaxed and she started catching her breath.
“Oh, that was so good. Your learning fast my young sweetheart.”. She seemed to be talking to me like I was just a boy, but that just wasn’t the case. I was a teen, practically a man, or at least in a few years. I didn’t shave yet or anything, but still.
“Let me show you something fun” she said with a mischievous smile. Sitting up, she pushed me back so I lay in my back. Then she crawled herself over me, reversing herself so she was sitting on my face, but facing my feet this time. She lowered herself down, pushing her pussy down to my face. In response, my tongue came out and started probing and teasing her. She ground her hips around as she rode my face like a horse.
“Oh that’s right...oh, you darling boy, I wish I could just keep you here forever” she moaned, as I licked her clitoris. Then she did something unexpected, and leaned forward, laying herself down on me so her face was right by my cock. Holy shit...we were about to do a 69! I had heard of this, but never imagined I would do it. Especially not with her!
As her face came closer to my cock, I could feel her hair falling around it, and her warm breath on it, as she teased me.
“Doesn’t look like I’ll have too much trouble getting this guy going again” she said in reference to my cock which started straining as her face got closer to it. She opened her mouth, and gently took the head in, expertly manipulating it with her tongue as I returned the favour.
The two of us lay on the large couch, her on top of me, as we made love orally with heated passion. It felt so good, so right. My crush on her felt like love at this moment as the two of us communicated through each other’s sexual organs, pleasing each other in mutual passion. I could have lain here forever doing this to her, but as the movements started to really heat up, she removed her mouth from my cock and pulled her pussy away from my face. I had to admit I was marginally disappointed.
As she mover her body up, she turned and looked at me with a smile.
“Ok sit up, now darling.”, she said in a hot erotic voice. Sitting up, I leaned forward, but she gently placed a hand on my chest, applying light pressure,. “Just sit back there sweetheart”, as I complied and leaned back sitting in her couch.
She crawled up onto me, straddling me with a leg on either side of me as I sat back, letting her take command.
“Ok, I think it’s time we consummate this relationship!” She said sweetly. Consummate? Did she mean....................?
“I need to make love to you now! I want to feel you inside me so bad, it’s killing me!”
Holy shit! This is it! I’m about to lose my virginity! With Helen!
She smiled, mischievously, as though reading my thoughts.
“Now control yourself there love. I don’t want you having a heart attack on me”, as she lowered her body into my lap. In the back of my mind, I thought for a second about protection, but quickly dismissed the thought. She was probably on the pill, and if not she would probably have me pull out.
I sat there, tensed and excited, knowing that I was seconds away from losing my virginity. My straining cock could literally feel the heat radiating from her pussy as she lowered herself into position. My cock was twitching with excitement as she deliberately delayed the process, teasing me with her pussy just millimetres away from the head of my cock, as I could feel her moist heat emanating towards my bell end.
I wanted this so bad it was killing me. Looking into my eyes, she lowered her body until her soft moist flesh touched the head of my cock, causing me to gasp from the sensation as she smiled sweetly.
“I’m flattered that I have this effect on you Rick” she said seductively
“Let’s see if we can take this a little further” she said, and gently she lowered herself down a bit so her weight pushed her pussy lips against my cock head. Her clenching lips resisted for a second, then yielded to her weight, and parted, allowing my cock head to slip inside her pussy.
My eyes popped wide open, as I gasped, my heart pounding. It was incredible, the sensation of her soft womanly flesh, grasping the sensitive head of my rock hard cock. I was in heaven and I wasn’t even all the way in yet. I had always fantasized about sex, imagined what a woman’s pussy would actually feel like wrapped around my cock, and here it was way better than I imagined. Every nerve ending in my cock head was screaming with excitement at the feel of her soft warm flesh grasping my cock head. Looking at her, I couldn’t believe that such a beautiful woman was doing this with me. Compared to the men should could have, I was just a boy, yet here she was, lowering herself onto my body, taking my cock inside her.
She smiled, at my facial expression, not in a mocking way, but in an understanding way. Leaning in she kissed me tenderly on the lips, then pulled her face back, and maintaining eye contact, released her weight slowly, allowing her to impale herself slowly on my cock.
As the grasping ring inside her pussy lips clung to me, I was overwhelmed by the sensation of her grasping pussy sliding over my sensitive skin, grasping my throbbing cock as it slowly engulfed it. The moment seemed to take forever, as the feelings took over my body. I couldn’t even speak, I just sat there gasping, barely able to breath as my wide open eyes were locked on her beautiful eyes, and I just accepted what was happening to me.
Slowly, as her flesh slid over me, she eventually took the whole thing inside as her buttocks pressed against my pelvis/thighs and her pussy grasped the entire length of my cock. I couldn’t move. I just sat there, panting, feeling my heart pound against my chest as I sat there captive to the overwhelming sensations assailing me. I had no idea sex could be so physically, mentally and emotionally powerful. In addition to the wonderful feeling of her pussy grasping my young cock, I had the feel of her soft skin against my body, her erect nipples brushing against my chest, the visual presentation of such a beautiful woman, her sexy perfume combined with the scent coming from her pussy. I never wanted this moment to end. Nothing in life would ever compare against this. Most guys would lose their virginity in a clumsy fumble with another high school girl, using a condom and here I was having the most intense sexual experience ever with the hottest looking cougar lady ever.........and I was only a high school kid! Doing this at my age......with this super hot looking goddess! Fuck!
I opened my mouth and was about to say something when she flexed her pussy suddenly, clamping down on my cock, causing me to gasp loudly instead of speaking, my back arching as my entire body jumped from the sensation. Maintaining eye contact she smiled sweetly at my reaction. I tried again to speak and she did it again, and again my words were lost in a gasp.
“Oh, I see you like that.” she said in a husky voice. Leaning in she kissed me on the lips, her tongue probing my mouth as I kissed back. Breaking the kiss, she mover her mouth slowly alongside my check, breathing lustily on my skin as her mouth approached my ear; As her lips touched my ear, I could feel her warm breath entering as her lips touched my ear, and my whole body quivered from the sensation.
“Oh, I’m going to enjoy introducing you to the ways a body can feel pleasure”, and with that she really clamped down, causing my head to jerk back as I gasped, more of a yelp while she threw her head back almost as though in victory, causing her hair to swirl wonderfully around her face.
Looking back at her, we maintained eye contact, which was in itself so intimate, enhancing the physical pleasure of the moment. Then she started to rise, raising her body as her flesh slowly slid off of my cock, gradually freeing it, inch by inch until only the head remained. She paused there, looking at me for a second and then she lowered herself onto me, slowly but assertively as her flesh slid over me again, causing me to moan from the feeling of her grasping pussy sliding over my cock, taking it in, massaging it as she went. Several times as she slowly took it in, she clamped, causing me to jerk and gasp as she did this until she was fully seated again.
Leaning in, she touched her nipples to my chest, her lips to my mouth and repeated the process, clamping her mouth on mine when I gasped, forcing a kiss as her tongue explored my mouth and our tongues danced.
Then she started fucking me. Slowly, but continuously as she slowly went up, pausing then down, repeatedly as her hands caressed my body, and mine hers, and we kissed romantically, passionately like lovers. I was having the most powerful sexual experience I think a guy could have and I didn’t even have my driver’s licence!
She rode me, slowly, rhythmically as I took in the sensations. Her body undulated erotically as she did this, and the visual of her movements alone were hot as hell, but the feel of her pussy grasping me, her smell, her touch and the taste of her mouth were just overpowering me. She was in complete control of my body and mind, and she knew it.
This went on for some time, her body moving over mine as she fucked me on the couch in her basement, our bodies moving against each others, our hands exploring. I started instinctively raising my pelvis up as we made love passionately, my hips coming up to meet her buttocks as she came down.
At one point she started brushing her nipples up against my face as she rode me, and I opened my mouth, taking one of the tender yet firm buds in my mouth and started teasing it, licking it, sucking on it.
‘Oh yes Rick....oh yes! Do that darling! Oh god you’re making me hot” as she started speeding up her actions, riding me faster now. The feeling of my cock, penetrating into her pussy, past those delicate lips and deep into her womanly body felt so right. I didn’t think beyond the present or anything else; just focusing on the fact that my most intimate body part was penetrating past hers, and was deep inside her body. Just the thought of it alone was erotic.
She started fucking me faster, riding me as my hands started grabbing her ass, feeling those soft yet toned lady buttocks. She started fucking faster, and faster, riding me aggressively. As our movements increased, she started to perspire, her body glowing with perspiration as the wetness of her skin shone erotically in the dim light of the basement. The sweat on her face, her breasts, her body was a visual picture of erotic perfection as she rode me. The feel of her damp skin against mine was even more arousing than it had been before.
“Oh you’re mine! I’ve claimed you as mine!” she said lustily!
I wanted to speak, but still was trying to just control my breathing.
She leaned in, her mouth close to my ear, her breath teasing it, as her lips gingerly brushed against it.
“Tell me you’re mine Rick! “
I took in a deep breath, and gasped “I’m yours”
“Call me Helen Rick” as she rode me like she was possessed, fucking me with hard aggression now.
“”I’m yours Helen” I gasped again
“Oh I love you Rick. You beautiful boy......I love you.....you’re mine. I claim you!” She moaned. This seemed a bit over the top but at the same time I liked it. She was better looking than any girl in my school.
“Do you love me Rick?” she asked, which caught me off guard, but then I thought, yes. Of course. She’s beautiful, and evidently loves me or she wouldn’t be asking.
“Yes” I gasped
“Say it!” she said insistently as she rode me harder
“I love you!” I gasped as she rode me faster, with almost desperate urgency
“Say it and call me Helen!” she moaned, pulling her face away from my ears, looking into my eyes.
“I love you Helen!” I said, sincerely. Hell yes I loved her. I had had a thing for her since I was in training wheels, and now she took my virginity, loved me. Heck, I didn’t care if she was using protection. I would marry her even, so lost I was in her beauty and tenderness. The thought even crossed my mind that I might impregnate her....and I liked it.
She smiled upon hearing the words, and started fucking me faster, harder, her body almost assaulting mine her copulation became so urgent in her need for release she rode my body hard, her tender womanly flower grasping my hardness as it went up, sliding almost all the way off my cock and then down, slamming herself down to be impaled as her buttocks slammed into my hips while she rode me.
All this was great but I was starting to come to the end. The feel of her soft delicate flesh sliding over my sensitive cock as she grasped me tightly with her inner muscles, the feel of her skin against me, her warmth, her scent, her beauty were all driving me to the edge and I didn’t think I would be able to hold out much longer.
“Oh Rick, I’m going to come soon...come with me! Come inside me!”
She didn’t need to encourage me at all. I was ready to climax and soon, the heat, the sensation, the intimacy of the moment and of course her tight grasping pussy, grasping me, sliding over my flesh drove me over the edge and I felt my orgasm about to start.
“Oh Rick! I’m coming!” she screamed as she pounded her body down onto my hips ferociously, and then suddenly my orgasm exploded ferociously, taking over my whole body as though every fiber of my being was having an orgasm, and I arched my back, throwing my head back as I gave myself to the sensation.
At the same time she screamed in heat; “Yes! I’m coming! Oh Rick” as she planted her body down hard, driving her buttocks down onto my hips as she engulfed my entire cock inside her and she kissed me hard on the mouth as we both climaxed simultaneously. My cock erupted inside her, spewing my semen up inside her as though with jet propulsion, as her pussy quivered and clamped down on me, while she kissed me as though starving for my mouth and both of our bodies quivered in excitement and heat as my fluids released themselves deep inside her body. We quivered like this for seemingly an eternity as our bodies felt the release they needed and then both of us sagged simultaneously, her hot sweaty body collapsing against my chest limply. Her pounding heart beat through her chest into mine as mine pounded back. My cock still twitched, sending residual spurts into her as her pussy still twitched in reflex to the climax it just experienced.
We sat there, our bodies and souls connected, as her tender delicate ladies body lay forward against mine as I sat back on the couch, my hardened flesh still inside her. I had just made love to a woman who had been in my fantasies since childhood. She had taken my virginity, and I came inside her body without protection, and it felt so right.
Finally she moved her head away from my shoulder, looking at me.
“Rick, I’ve been watching you for awhile now, and just knew you would be perfect for me” she said with sincerity, as I basked in the compliment. I was faintly aware of the fact that I was still inside her.
Leaning forward, she placed her mouth against my ear, and spoke huskily;
“I wanted you! I knew I had to have you; to take you, to make you mine! I just had to take you. I love knowing that you never had sex before me. I’m your first, your last,.......your only” she said lovingly as her mouth moved away from my ear, towards my neck.
I was in the process of wondering what she meant by ‘my last and only’ when her mouth seemed to clamp down on the side of my neck, and suddenly a piercing pain drove into my neck as she seemed to bite down with tremendous force. I jerked and tried to scream but my throat seemed to be unable to work, with steely prongs driven into it. I panicked in my agony, and struggled to throw her off, but her arms were like steel, pinning me effortlessly as they held me in place while she dug herself into my throat. She was a small woman, but she overpowered me like I was a child, and held me still as she bit deep into my throat. Terror gripped me, even more so than the pain. What the hell was she doing to me? I felt what seemed like two short fangs from her bottom jaw clamping onto my neck, while two long fangs in her upper jaw drove inside, tearing my throat, entering my windpipe, causing blood to spray inside as I choked.
Withdrawing the fangs, she released the hold on my neck, pulling her head back to look at me, yet her insanely powerful body held me in place. I could see now what my mind knew but tried to deny. It was a terrifying sight. Her face still looked mostly the same in all its beauty, but there were terrifying changes to it. First, her eyes no longer looked the same; they had changed colour to something much darker. Secondly, she had long fangs protruding from her mouth, and blood dribbling out of her mouth and down her chin.
I was terrified. I fought furiously against the steely arms pinning me down with ease. The pain in my neck, the difficulty breathing with my neck injury and the terror of seeing what a beast she was had me struggling desperately for my life. I wanted to live!
“Rick,...sweetheart, don’t fight it; your just making it harder for yourself. Give in, let it happen...it will be a lot easier for you that way dear; much easier. I promise, you’ll see”
With that she opened her mouth, and with a beastly howl, her face shot forward with almost blinding speed, and she clamped down on my neck, tearing into it painfully as I thrashed helplessly in her arms. Suddenly I felt something rupture in my neck, and could sense the blood suddenly flow like as though from a pump. I saw it spray on the part of her face I could see, and suddenly felt hot thick fluid spraying into my windpipe, filling into my lungs as I gagged and choked.
Her mouth clamped onto the opening in my neck and I could feel her sucking ferociously as though starving.
I fought back still, struggling as I gurgled blood, yet I felt my arms and legs rapidly weakening, as they started to go numb with a tingly sensation. At the same time, I felt my eyelids getting heavy as they fluttered, and my field of vision started to get spotty.
I felt my eyelids flickering as everything started to go black..................
The game was tight, but we beat them. While I was not the top player on the team (although I was an OK player), this was definitely my best game. Looking out at the stands she was there. Her name was Helen, or Ms. Caldwell as she called herself. She was so hot, I always checked her out. She was in her 30’s and had a fucking amazing body. She looked so sexy in her business suit, and I couldn’t help but wonder what she was doing at the game. She smiled at me when people cheered my performance, and it made me rubbery legged. She was always so sweet to me, but I know she just thinks of me as a boy and nothing more. I on the other hand, had harboured a massive crush on her since I was in training wheels. Now as a teen, I felt like I should come across as more mature, however the fact remained, that while I was working out and it was starting to show, I still had a teens body, not a man’s body. I didn’t shave yet, and had no hair on my chest.
As I made my way off the field, I started putting my equipment in my bag, I said goodbye to my team mates and coach and started heading home.
‘Hey Rick, Great game!”
Her voice....my legs went rubbery
“oh hi...uh...uhm yeah I think....” fuck I sounded like an awkward shy boy, “Uhm yeah, thank you Ms. Caldwell....I am glad you liked it”. Fuck I sounded like a kid!
Smiling at me, as though trying to be understanding about my awkwardness she walked up to me.
“Heading home? I’ll walk with you”, she said as her hips wiggled hotly while she walked in her heels.
“OK, sure!” I cringed at how excited I sounded when I said that.
She walked home with me, talking away with me as we went. I was so excited at the opportunity to walk with her that I could feel my heart speed up.
“Play any other sports at your school?” She asked with genuine interest
“Uhm....well not right now, this is the only sport this season. I am planning on joining the wrestling team though” This was a lie. I had no interest, but I figured it would sound macho. She smiled her approval.
She made small talk for the duration of our walk, and I did my best to engage in conversation with her, while trying to sound mature. As we walked, I did everything I could to try to stick my chest out, without making it look like I was sticking my chest out. I was in very good shape, but I still had a teen body, rather than a man’s body, which made me feel shy around her. Helen on the other hand definitely had a woman’s body. She had curvaceous hips, a small waist and perfectly sized breasts for her body size. The way her body moved as she walked, combined with the click of her heels was soooooo fucking hot it was driving me insane. I sincerely hoped she couldn’t tell what I was thinking of her. As a grown adult, if she had any idea of the sexual thoughts going through my mind, she would have been highly offended and unimpressed with me.
The whole time we talked, she seemed genuinely interested in what I had to say, which was flattering to me. Don’t get me wrong, I was no geek, but I was definitely shy around girls, and was still a virgin. Most of my friends were too, but we all lied and made up stories of having scored despite the fact that we had only scored with our hands. We were still young, so time would change that.
Eventually she got around to asking if I had a girlfriend. I didn’t have anyone serious. I had fooled around with one girl, and managed to feel her breasts through her bra, but that was about it. I had kissed a couple of girls, but only managed to fondle the one. Most of my friends had gone a bit further than that. My problem was not my looks, but the fact that I was shy.
“Uh...uhm well nothing that’s....serious you know” I said awkwardly
“No need to rush into anything serious, you’re still young” she said reassuringly. I couldn’t tell if she was giving advice or just patronizing me out of sympathy. As if reading my thoughts, she spoke again.
“You’ll do fine when the time comes...you’re a very good looking guy. There are plenty of girls who would like to be with you”, she said with a genuine smile and sincerity. This made my heart speed up with excitement. Ms. Caldwell had called me good looking!!!!
“Uh..thank you” I said, trying not to sound too excited or boyish. I’m not sure how good of a job I did.
As we approached her house, more than a block before mine, I prepared to say goodbye to her when she spoke
“Rick, are you in a hurry? I have some things I need brought down to my basement, and I could use a strong guy to do some lifting. I would really appreciate your help” She asked.
‘Sure!” I said, and immediately cringed at how enthusiastic I sounded. That must have sounded like a dead giveaway. “I mean...I don’t mind helping”, feeling even more flustered at my pathetic attempt at recovering.
‘Oh excellent, thank you!” She said with a smile, “I’ll make it worth your while” she said.
I certainly knew how I would like her to make it worth my while, but that was obviously not what she meant by that.
I followed her up to her door, checking her out from behind as her heels clicked on the walkway. My mind was abound with fantasies of her jumping me when we got inside, but that stuff was the product of Penthouse forum stories, and not reality. She was fucking hot, and dated men, not boys, but still the fantasy was there.
“OK, those boxes over there need to go in the basement, and those three in the separate pile need to go upstairs.” She said, “Thanks again for doing this Rick”
“No problem Ms. Caldwell”
“Call me Helen”, she said sweetly. Holy shit!
“OK... Helen”, fuck, I could feel I was blushing.
Walking over to the first box, I grabbed onto it and realized it was quite heavy. I was determined however to look as manly as possible, so I lifted while trying to maintain a facial expression that showed total relaxation. She smiled approvingly as I lifted. I did everything in my power to flex my muscles, without making it obvious I was doing so.
Heading downstairs, I carried the first box, following her as she showed me where it was going. It was quite heavy, so I was relieved when we finally got there, but again I made a point of acting like it was easy to carry.
“Looks like you are managing just fine” she said with a smile.
I spent the next little while, lifting boxes, carrying them downstairs, always trying to puff out my chest, and flex my biceps. It felt incredible to be doing manly work in front of Helen, as she watched. I tried to imagine that she was getting turned on by this, but again this was just fantasy.
When I finished with the boxes going downstairs, I approached her to find out where the other boxes were going.
“Grab the box with the yellow tape on it and come with me”, she said walking toward the stairs. I followed, and as we ascended the stairs, I couldn’t help but stair at the bottom of her skirt, as from this angle I could get a better view. I still couldn’t see her panties or anything but the look of her lower thighs from behind was a sight for a young guy like me.
“You managing that OK?” she asked, as I looked up rapidly to see her looking back at me. I hoped to fuck she didn’t see me checking her out. ‘Please...tell me she didn’t bust me!’ I thought.
She smiled sweetly, and guided me to her den and showed me where the box went. I went to get the other box, as she waited for me. As I walked towards the den, she stepped out and instructed me to follow her as she guided me into....her bedroom! Holy shit! I’m in Helen Caldwell’s bedroom! I thought. Many fantasies had placed me in this room.
“OK, just put it over there young man” she said with a cheerful tone as I caught her smiling at me, mostly sweetly, but partly with a faint sense of amusement. I couldn’t help but wonder if my expression had tipped her off as to what I was thinking. I was blushing again.
Heading downstairs, I grabbed the other box and carried it upstairs to the hot looking goddess’s bedroom. I didn’t hurry too much when I got there. I was not likely to ever be in her bedroom again, so I figured I might as well make it last. Putting down the box, I made sure to posture myself well, but again not to be too obvious.
Standing, I looked at her. ‘So...uhm....is that..uh..it?”, I shifted awkwardly.
“Yup, that’s all. Good thing I ran into you. I never could have lifted those boxes” she said. Reaching out she put her hand on my bicep.
“For strong guy like you, I’m sure it was no problem” she said. My knees just about buckled!
‘Uhm...ahem uh yeah, it was no problem” I said, trying to seem manly. Fuck I felt awkward. I hoped she wasn’t patronizing me. I worked out, and had biceps, but it was still boyish muscle and not the beefy hard manly muscle.
“Come on downstairs. Let me make you something to eat” she said, heading out of the room.
“OK” I said, wishing we could stay in the room.
Heading downstairs, I went to her kitchen and sat down as she prepared some food. I still couldn’t believe I was here, and now going to eat with her.
“Do you want something to drink? After hard work a man could probably use a cold beer”
Holy fuck!!! She just called me a man!...and offered me a beer!!!!
“Sure please!” I said, trying to control myself.
She reached into the fridge and pulled out a cold bottle, twisting the top off and handing it to me. I raised the bottle to my mouth and took a swig, trying to look natural. I really wasn’t a very experienced drinker. There was no way I would be able to go to a beer store without getting carded. My friend’s older brother had fake ID and could get beer, but he rarely ever got any for us.
She started preparing a tray with various cheeses, spreads and meats, with some crackers and other assorted items.
“Let’s go down to the recreation room in the basement”, she said wistfully. Following her, I walked into the darkened interior of the basement, which had a combination of rustic and postmodern design. The floor was stonework, with a marble top coffee table. It all looked very expensive, and she must have paid quite a fair amount of money to get this. The couch was nice leather and there was an exotic looking recliner.
‘Sit there” she said, gesturing to the couch.
I sat quickly, almost obediently. She placed the platter down in front of me. It looked amazing.
“Go ahead, eat” she said encouragingly. I leaned forward and grabbed a cracker and cut some cheese, placing it on the cracker. Let me tell you, this was the most amazing cheese I had ever tasted. I started sampling the wares, overwhelmed by the kaleidoscope of flavours I was experiencing. The cheeses, the meats, and other treats were all so good, I found myself pigging out and immediately felt self conscious.
“Are you having any?” I asked, gesturing to the tray
“Not now, but you go ahead. I have plenty more” she said as she walked over to a door off to the right. She emerged with a bottle of red wine, and opened it, grabbing some glasses. Walking back towards me she sat down and poured herself a glass. Then she went to pour me some and paused.
“I could get you another beer instead?” she asked, gesturing towards my near empty bottle. My first thought was to get another beer, but then wine seemed more to set a romantic tone.
“Wine would be nice” I said, trying to sound cool and relaxed. It may be nothing, but sitting in Helens nicely finished basement, having wine and cheese as we sit on the same couch. I was getting as horny as hell.
She handed me a glass and raised hers gesturing to me to do the same. Raising mine, I allowed it to clink lightly against hers and then took it to my mouth and took a swig. I almost immediately gagged...it was not cold. It was almost warm. I tried to hide the grimace.
‘Everything OK?” she asked
“Uhm, it’s fine, I guess it’s just that it’s not chilled”
“Oh you don’t chill red wine dear, just white wine”. DOH! I must have looked like an idiot.
“I can get you another beer?” she offered.
“No, this is fine thanks” as I took a small careful sip. I wanted to try to appear as mature and sophisticated as possible. She seemed to smile reassuringly. Did she realize how hard I was trying to impress her. We made small talk for awhile, and she seemed very friendly. When I said something that made her laugh, she sort of slapped my chest playfully. She may have just been being friendly, but to be a teenage boy, having a hot looking mature lady like her making any physical contact caused an instant hardon. I shifted uncomfortably, trying to position myself so she wouldn’t see it. As we talked some more, she seemed to be leaning in, getting herself very close to me, really maintaining eye contact. At one point she reached out and swept some crumbs off my shirt. My mind was going crazy, imagining that she was flirting with me. Part of me, the realistic part of me dismissed that as silly. I was a boy, and there was no way a hottie like her would choose a boy when she could have any man. I was still getting as horny as hell!
As we talked she was leaning forward, and I was getting a half decent (but not perfect) view of her cleavage. As I looked through the top of her blouse, she leaned ever so slightly forward as I strained my eyes to catch a glimpse.
I caught her looking down as though wondering what I was looking at and immediately brought my eyes up, hoping she didn’t bust me. She responded by sitting up a bit straighter, so I wouldn’t have as good of a view. I blushed, knowing deep down that I had been busted. At least she didn’t confront me on it. I would have just died of she did that.
As we talked, she brought her feet up onto the couch, and I was aware of the fact that I had a half decent view up her skirt now. I couldn’t tell because I was determined not to look directly. I didn’t want to push my luck and piss her off. The problem was, she was sort of sitting with her legs curled up beside her as she sat with her side against the back of the couch, facing me. As a result, every time she shifted a bit, the opening between her knees in her skirt tempted me. It was a game of willpower for me to not look up her skirt. Eventually I slipped and reflectively cast a glance at a view of her inner thighs, but did not get a look at her panties. She smiled at me, and I felt myself blush more. Did she catch that one? It was less than a second and she was reaching for her wine. Fuck, please tell me she didn’t catch me looking up her skirt. PLEASE!
We talked some more, her filling my glass of wine again, as I continued to drink it, trying to be all sophisticated. The truth was, I just wasn’t much a wine person I guess, but there was no way I was letting her know that.
Eventually the topic of a school dance came up. She had heard one of the girls in the stand talking about it.
“Are you taking some lucky girl to the dance?”
What a terrible question. I didn’t have a date, and didn’t have the nerve to ask a girl to the dance. The last school dance I went to, I stood there most of the time with my friends, and only in the last twenty minutes did I end up dancing with a girl. She had liked me, and I had liked her, but I stood there like an idiot most of the night until my friends practically told the two of us to dance. I had no idea what I was doing.
‘Uhm, not really...I guess I wasn’t sure if I was going to go”, I answered a bit embarrassed.
“Not going to go?” she said with alarm. “Rick, you only get to be young once. Don’t live with regret for the things you didn’t do!”
“Well, uh..I don’t really have a date, and uh......”, I flustered
“So if you don’t have a date that means you can dance with several young ladies. Think of it as an opportunity” she said with encouragement.
“Well, I guess I’m just....well I’m not a good dancer”, I admitted.
“Rick, you just have to relax and go with it. Besides, you can always do the slow dances. Those ones are nicer anyway” she said.
“I guess, but I don’t really know how to dance formal slow dances”, I admitted
“And most high schoolers don’t know how. Haven’t you seen them. The guy just put’s his arms around the girls waist and she puts hers around his neck, and they simply rotate slowly in a circle.”, she said with a bit of a laugh. She was right actually, that’s all they seemed to do.
Slapping me on the thigh, missing my erection by an inch, she stood.
“Come on, I’ll show you” she said, holding her hand out to me. I really didn’t want to stand, since my boner would be much more visible. Had her slap been an inch off I would have been busted. Fuck she was hot! Why couldn’t I make this stupid erection go away?!
“Come on, take my hand” she said gesturing.
Reluctantly, I reached out and took it and she pulled gently. I stood, moving awkwardly, trying to keep my hands low in front of me to cover my erection, but not be obvious that I was hiding something.
She reached out, and put her arms around my neck, and moved in close.
“Put your arms around my waist”, she instructed. I did this awkwardly, unable to believe I was now in such an intimate position with Helen.
“Now we just slowly go in circles, making small steps...anybody can do it” she said. I followed her instructions, and tried to look like I was calm and relaxed, when I was as excited as hell. Helen and I were standing face to face, dancing in a romantic kind of way, alone in her basement. Holy shit! If my friends could just see me now!
As we danced, she started moving in closer as she gave minor instructions and encouragements. I was worried, because if she pressed up against me she would feel my erection, and I was terrified about her spotting that. I tried to keep my hips back, so she would not brush up against it, but she told me to straighten up, while smiling encouragingly, telling me I was doing fine.
Suddenly without warning, she moved her hips forward a bit, and before I could even react her thigh brushed against it and I knew right away that she felt it. She immediately paused, and stepped back.
“Uh-oh, what is this?” she said in a serious tone. I tried to twist away but she stopped me, and looked down. I could feel my face blushing insanely, and wanted to just disappear. She was being nice to me and I was just getting horny.
Looking at me with an accusing look, she asked me in a stern tone
“Would you care to explain yourself Rick?”
Holy shit this was horrible. She was a grown woman and I was caught getting all horny over her. Shit! Would I be in trouble? Would she say something to my parents? Fuck I was so embarrassed.
“Rick?” she asked, questioningly. I was staring down, fumbling for words
“Rick, look at me when you talk to me”. I looked up, horribly embarrassed, with an apologetic look on my face, as I fumbled for words. I wished I could just die at that moment.
She looked at me hard for another few seconds, then a huge smirk broke out on her face and she let out a burst of laughter.
“Relax, I’m just giving you a hard time. That’s perfectly normal for a guy your age. I should have been more careful. Any of your classmates would have had the same reaction, so don’t feel embarrassed”, she said with a reassuring smile, touching my face.
I was still having a hard time talking, as my face glowed.
“Oh, I’m sorry” she said mirthfully, “ I was just having a bit of fun with you...I shouldn’t have teased you like that” as she touched my cheek tenderly.
“Come on, let’s get you seated down so you will be able to relax” she said, taking my hand and guiding me to the couch.
“Rick, I’m not upset OK. I’m flattered to be honest, a handsome young guy like you finding a lady my age attractive” she said with a flashing smile.
‘Her age’ I thought? She was in her early 30’s not her fucking 60’s for crying out loud. And she obviously worked out regularly and watched her diet. Besides her face was very smooth, with no wrinkles.
Sitting down, I tried to relax as she sat beside me, facing me on the couch.
“Here, have some more wine” she said. This time I took a huge swig, trying to get my heart to stop pounding.
“Have some snacks, they’ll help you relax” she said as she grabbed a cracker, and spread some sort of hot jelly on it for me.
“Here, you haven’t tried this one yet” she said, holding it out to me as I took it from her and held it to my mouth, taking a bite. She was immediately preparing another smaller cracker for me, this time with some sort of meat spread. The cracker I was eating was overloaded and I got the jelly all over my fingers as I ate. She held the other one up and as I reached for it, she shook her head.
“No, you have that pepper jelly all over your fingers...here, just open your mouth” she said as she held the cracker to my face. Oh my god! I opened my mouth, and tried to take the cracker from her fingers, but as she pushed it in, her fingers went too far and her finger flicked my tongue. It was the most erotic thing I had ever experienced in my young life.
She smiled, and as I looked around for a tissue for my sticky fingers, she took my hand and brought it close to her.
“Here, let’s not let this go to waste”, and she took one of her own fingers and used it to wipe the jelly off of the finger that had the least jelly on it. With that, she raised her finger to her mouth and licked it off. I could feel some wetness inside my pants, and my boner was screaming and twitching for release.
Then she took the next finger and raised it directly to her mouth, and stuck out her tongue and started licking the jelly off of my finger. Holy fuck, I realize she was just licking my finger, but this was so fucking hot I couldn’t believe it! Smiling, she took the last finger, and raising it to her mouth she stuck it in her mouth and started sucking the jelly off, her tongue swirling around my finger as she sucked. I could barely breathe, and realized my mouth was hanging open. My finger was still in her mouth when she looked at me deviously as she took it out, and she leaned forward. Touching her hand to my thigh, she spoke;
“Oh yes, I’m very flattered” she said as her hand slid towards my erection, gliding over the material covering it, as my erection jumped and twitched.
“I was trying to get you going from the start” she said with a smile, “ I just enjoyed the suspense, but I can’t torture you forever..............besides I want to have you right now”, she said, leaning way forward, starting to climb on top of me.
WHAT THE FUCK!? Was I dreaming? My mouth was wide open as she moved over me and leaned in to kiss me. The suddenness of her turnaround hit me like a train.
“Nervous? I don’t bite” she said, responding to the fact that I was frozen. Her lips touched mine and I felt a jolt go through me at the contact. I was on a couch, making out with the hottest looking lady in town. She leaned into me, her body pressing against mine as her tongue probed my mouth.
Breaking the kiss she spoke, “Relax, you’re so tense, and you’re not breathing”
I did my best to relax, but I was overwhelmed with the moment. It was hot, yet I was nervous as hell. I had no experience! I had kissed another girl at the school, and had felt her a bit, outside her clothes, but I had never had sex! I didn’t know what to do! I hadn’t even seen or touched a girls pussy! Hell I hadn’t touched a girls tits except through her clothes.
The feel of her warm body pressed against mine had me twitching with excitement, as I felt slight moisture inside my underwear. We kissed for several more minutes, her on top of me as I leaned back in the couch, feeling her slender body pressing down on mine. I was so horny it was killing me. Our hands roamed over each other’s bodies, as I stroked her back, and her sides. I wanted to bring my hands around front and feel her breasts but was not sure if she would mind.
As if reading my mind she spoke, “Rick, you can let your hands explore...I’m pretty sure I know where you want to put them” she said encouragingly. I didn’t need to be told twice, and immediately brought my hands to her breasts, feeling them through her shirt.
“Let me help you” she said, moving my hands away as she sat up, straddling me. She gently brought her hands up to her blouse and started undoing the buttons very slowly, smiling seductively the whole time as I stared at her opening cleavage like a deer in the headlights. As her shirt fell open, she reached forward and undid her bra which was one of those front opening ones. Falling out of the opening bra was the most beautiful set of tits in the world; not exceptionally big, but so well formed and tender looking!
Tentatively, I reached foreward, placing my palms on them and as soon as my skin made contact with them, I almost gasped from excitement at the feel of these soft yet formed orbs in my hands as I massaged them, playing with them getting lost in the excitement of them. I squeezed them, stroked them, felt the nipples.
“Don’t forget that the rest of me is still here Rick?” she said jokingly.
She took my hands and pulled them away, pushing them back so they were beside my shoulders. Then she leaned forward, riding a bit and brought those amazing tits close to my face so I could access them with my mouth. My head was spinning with excitement. I had the hottest lady in the neighbourhood sticking her tits in my face!
Opening my mouth, I tentatively took a nipple into it and closed my lips upon it, running my tongue over it.
“Ooooohh, Rick, you have no idea how good that feels” she purred as she started grinding her body on top of mine. I was almost spinning with ecstasy, as her body pressed down on me, her crotch grinding into mine as I sucked on her nipple. She took my head in her two hands and started grinding her tits up against my face, allowing me to suck on them one at a time. The sensations through my body, in my groin were overwhelming me, almost as though about to cause me a short circuit.
“Oh my god Rick, this is getting me so hot!” she purred sensuously as her crotch ground against me. ‘getting her so hot?’ I mused. I could feel the heat from her pussy radiating through the thin material of her panties, and then through my pants against my straining cock. I started grinding my hips upwards to meet her grinding as I continued sucking on her tits.
Her hands started aggressively going under my shirt, yanking it up over my head so aggressively she caused a small rip. She was almost attacking me sexually, as though starving for sex (which was perfectly fine by me), but it seemed so weird for such a hot looking woman. I mean, there’s nothing wrong with me or anything, but I’m just an average teen, yet she was attacking me like I was some sort of sex god. I wasn’t about to argue
“Let’s get these off of you there young man” she said as she started undoing my pants. I sort of nodded, and tried to speak, but instead fumbled my words. She barely noticed as she started yanking and tugging on the pants as I raised my butt off the couch to allow her to remove them. She got them off in no time, taking my underwear with them. Shortly thereafter she removed her own remaining clothing and before I knew it I was naked with the hottest looking lady in our entire town!
Sitting there naked on the couch with her, I was exploding with hormones! My cock was straining to the point of exploding as I took in the softness of her flesh and her feminine scent! Just the smell of her was driving me crazy. Oh my god I wanted her. Closing my eyes, I breathed in, taking in her perfume, as I felt her soft skin against mine. The whole experience was driving me wild with arousal.
Her hands ran over my body, feeling my chest as I sat there, kind of wishing I had at least a bit of hair on my chest. As she ran a hand over my arm, I made a conscious effort to tense my bicep, without making it obvious I was doing so.
“Oh, I love your hot young body” she purred as she gently traced her hand down my navel. Her hand moved towards my cock, and when it touched me I almost gasped from the sensation. She wrapped her soft hand around my cock, and started gently stroking it up and down as I tried to control my breathing.
My hands were roaming over her body, feeling her breasts, and her ass. I started tentatively moving my hand between her legs, gently bringing it up her inner thigh, not sure if I had permission to touch her pussy. She quickly reached down and grabbed my hand, and pulled it to her pussy. When my finger touched her soft flesh, I was almost out of control with excitement. I was touching a girl’s pussy for the first time! I had always wondered what one would actually feel like, and now that I was touching one I wasn’t disappointed. I started exploring, feeling the flesh, and probing inside of her as she squirmed against my body, stroking my cock.
I explored her a little further, seeking out her clitoris. I had never seen one, but had an idea where it would be. I found a soft little bump, just forward of her opening and stroked it gently. She immediately gasped and tensed up over me as she kissed me hard on the mouth.
“Oh Rick, you make me feel so good” She said in a husky voice. “Do you want to do something for me; to make me feel real good?” she asked seductively. I could barely speak, and just nodded my head dumbly.
She pushed me down on the couch, so I was laying on my back, and then she lay down on top of me naked, as I felt the heat from her pussy inches from my throbbing cock. She kissed my hard, squirming her body on top of mine, then started moving forward, bring first her neck close to my mouth, and then her breasts as she moved foreward more. Her body moved up even more as her belly was touching my mouth. I kissed and licked it, hoping it felt good for her. As she moved her body forward more, it became evident she wanted to put her pussy up to my mouth, so I could eat her. I was both excited and nervous at the same time. On one hand, placing ones mouth on another genitals seems a bit weird, yet apparently many guys like doing that with a woman. Would it taste bad? Would it taste good. My questions were quickly answered as she straddled my face, pushing her pussy up against my mouth. The scent was strong, but not at all bad. She seemed eager for me to get started, and literally ground her pussy against my mouth.
“Oh be a good boy, and use your tongue on me. Put it in there sweetheart...oh god I want you to eat me” she said, riding my face. I stuck my tongue out, and pushed it between her folds making her almost jump. I pushed further, seeing how far I could push my tongue into her depths, as I felt her internal muscles, contracting around my tongue.
“You don’t have to push deep sweetheart. Less is more. Be gentle, and gradually work closer to my clitoris, but don’t lick it directly, at least not right away”
Complying with her instructions, I worked on her pussy as she rode my face like it was a horse. It felt a little one sided, but I was still thrilled to have my face between her legs like this. Oh my god, if my friends could just see me now. I was with a woman I had fantasized about for years, but never imagined I would actually touch......and I had already gone father with her than I had with any girl at my school.
I worked my tongue closer and closer to her clitoris with each stroke, as her body undulated erotically as though dancing over my face. My cock was straining with excitement, pre-cum dripping out of the end. Her taste in my mouth was such an erotic experience.
“Ok now start lightly licking the clitoris....delicately, like a feather”
Complying, I started flicking it and she immediately squealed, grinding herself down on my face. “Oh, I want to just keep you here forever....such a sweet boy, so hot!”
The whole ‘sweet boy’ thing didn’t sit well with me as I wanted her to see me as a man, but with the hottest looking cougar/MILF sticking her pussy in my young teenage face I was not about to start correcting her. So long as she was sexing me up like this she could call me anything she wanted.
“Oh faster Rick.....start putting more pressure” she moaned heatedly as she started moving her hips faster over my face, swaying her body as her perfect beautiful breasts swayed with the motion of her body. I complied, licking faster and harder, making this hot looking lady squeal and moan as she rode my face like a bucking bronco.
“Oh yes...suck my clit into your mouth,”
Complying I sucked the little nub into my mouth, sucking hard as she squealed and ground her crotch into my face.
“Oh yes Rick! Suck on at and use your tongue at the same time!”
I did exactly that and it pushed her right over the edge as she tensed up on top of my face, emitting a squealing moan of ecstasy as he body quivered over me with her delicious pussy on my mouth. Her orgasm held for another moment or two until she stopped trembling and twitching, and then relaxed, breathing heavily.
Crawling off of my face she smiled, while laying down on top of me; she started kissing my neck as I savoured the sensation. She started gradually working her way down my body, kissing my chest, my abdomen....and eventually she was down, kneeling forward looking at my straining cock. I was tense with excitement as she breathed on my erection, her warm moist breath teasing the sensitive organ as I lay there trying to control my breathing.
She leaned forward and kissed it, causing me to gasp from the sensation. It may seem pretty ordinary to you, but for a young virgin my age, with the hottest looking lady on the block, that kiss on the dick was heaven.
She started gently moving her lips along the hardened flesh, breathing on it, barely touching it as I strained. She worked her way from the base, up to the tip, and then back down to the base. Then she touched her tongue to the base, making my cock jump with excitement. She tenderly ran her tongue along the shaft as I lay there gasping, my fists clenched. She kept this up for several minutes, driving me crazy until she brought her mouth up to the tip, and then very gently, she opened her mouth, and closed it over the head of my cock as I arched my back from the sensation. I could see her eyes looking at me mischievously as she held it gently there in her mouth. Then I just about jumped again, when her tongue touched the opening at the end while my head was in her mouth. She was lightly sucking on the head as her tongue teased the opening at the end of my cock. I was straining, and then as if things couldn’t get more intense, she started taking more of my cock into her mouth, while maintaining eye contact, a smile evident in her eyes. She could see what this was doing to me and she liked it.
As she started taking more in, I felt as though I was about to come soon.
“Ms. Cald.....I mean Helen, I think I’m going to...”
She pulled her mouth away, “You’re going to come?” she asked smiling.
“Let’s see if we can make this last” she said smiling, as she went to work. She would work on me, turning up the pressure, taking my cock in her mouth, until I was about to come, and then she would release it and go back to teasing it. She knew exactly what she was doing. At one point she had my entire cock in her mouth, with the head right at the back of her throat as she worked her tongue over the shaft. This kept up for several minutes, then as she was teasing the head again, while running her tongue over the hole, she grabbed my balls and started gently squeezing them as I delighted in the sensation. I suddenly felt my orgasm coming as she worked my balls and my shaft.
‘I’m going to......come.” I said in warning, but she ignored it and kept working me, until suddenly I exploded in her mouth. She suddenly sucked hard in the end of my cock as she squeezed my balls, which were now pimping semen right into her mouth. She was swallowing vigorously as I climaxed, still working me like an expert.
When I finished, and she milked the last drop out of me, swallowing it eagerly, she released my cock and balls, then looked at me.
“I had to get that out of the way. I don’t want you to have a hair trigger when we take this to the next level”
Next level! No way!
She crawled back up smothering me with kisses, molesting me with her hands as I did the same. I still couldn’t believe, that a shy young inexperienced teen like me had her soft skin up against me, ....and that I had just came in her mouth! Holy shit!.
“Looks like you enjoyed that sweetheart!” she said tenderly. She started rubbing herself all over me, and playing with me. Suddenly she lay back and pulled me towards her. So I lay on top of her. Holy shit I was about to have sex with her! I kissed her passionately, as I tried to get between her legs, but she started squirming, pushing on my shoulders, making me move down her body. I suddenly realized she wanted me to go down on her again. I was partly disappointed, because I really wanted to have sex with her, but I figured I could wait. I would eat her pussy for ten hours straight if that’s what I had to do to get to have sex with her.
Moving rapidly down her abdomen, I started kissing her flesh as I went.
“Oooohh....Rick, you know what a lady wants don’t you” she stated excitedly. I felt immediately flattered and was determined to give her the best oral sex she had ever had. Or at least I would try!
Moving my face down to her tender looking pussy, all I could think about was how that would feel around my cock. Fuck I wanted to have sex with her. I was dying.
As soon as my tongue touched her flesh, her body quivered and she arched her back, while spreading her legs wider. I went to work with considerable zeal. She had been the object of my fantasies for years. Many a nights had been spent masturbating while fantasizing about this scenario, but I never truly imagined it could happen for real.
I licked and sucked her clitoris as she squealed, and ground her pelvis up into my face. Her legs thrashed around, her abdomen fluttered and she literally squealed in delight as I ate her. Soon she started getting more excited and reached down with both hands, grabbing my hair and grinding my face into her crotch as she literally thrust her hips up, as though fucking my face until she suddenly seized up, quivering as she cried out in heated moans, her thighs clamping tightly on the sides of my head, her hand still pushing my face into her pussy for several more seconds until her body relaxed and she started catching her breath.
“Oh, that was so good. Your learning fast my young sweetheart.”. She seemed to be talking to me like I was just a boy, but that just wasn’t the case. I was a teen, practically a man, or at least in a few years. I didn’t shave yet or anything, but still.
“Let me show you something fun” she said with a mischievous smile. Sitting up, she pushed me back so I lay in my back. Then she crawled herself over me, reversing herself so she was sitting on my face, but facing my feet this time. She lowered herself down, pushing her pussy down to my face. In response, my tongue came out and started probing and teasing her. She ground her hips around as she rode my face like a horse.
“Oh that’s right...oh, you darling boy, I wish I could just keep you here forever” she moaned, as I licked her clitoris. Then she did something unexpected, and leaned forward, laying herself down on me so her face was right by my cock. Holy shit...we were about to do a 69! I had heard of this, but never imagined I would do it. Especially not with her!
As her face came closer to my cock, I could feel her hair falling around it, and her warm breath on it, as she teased me.
“Doesn’t look like I’ll have too much trouble getting this guy going again” she said in reference to my cock which started straining as her face got closer to it. She opened her mouth, and gently took the head in, expertly manipulating it with her tongue as I returned the favour.
The two of us lay on the large couch, her on top of me, as we made love orally with heated passion. It felt so good, so right. My crush on her felt like love at this moment as the two of us communicated through each other’s sexual organs, pleasing each other in mutual passion. I could have lain here forever doing this to her, but as the movements started to really heat up, she removed her mouth from my cock and pulled her pussy away from my face. I had to admit I was marginally disappointed.
As she mover her body up, she turned and looked at me with a smile.
“Ok sit up, now darling.”, she said in a hot erotic voice. Sitting up, I leaned forward, but she gently placed a hand on my chest, applying light pressure,. “Just sit back there sweetheart”, as I complied and leaned back sitting in her couch.
She crawled up onto me, straddling me with a leg on either side of me as I sat back, letting her take command.
“Ok, I think it’s time we consummate this relationship!” She said sweetly. Consummate? Did she mean....................?
“I need to make love to you now! I want to feel you inside me so bad, it’s killing me!”
Holy shit! This is it! I’m about to lose my virginity! With Helen!
She smiled, mischievously, as though reading my thoughts.
“Now control yourself there love. I don’t want you having a heart attack on me”, as she lowered her body into my lap. In the back of my mind, I thought for a second about protection, but quickly dismissed the thought. She was probably on the pill, and if not she would probably have me pull out.
I sat there, tensed and excited, knowing that I was seconds away from losing my virginity. My straining cock could literally feel the heat radiating from her pussy as she lowered herself into position. My cock was twitching with excitement as she deliberately delayed the process, teasing me with her pussy just millimetres away from the head of my cock, as I could feel her moist heat emanating towards my bell end.
I wanted this so bad it was killing me. Looking into my eyes, she lowered her body until her soft moist flesh touched the head of my cock, causing me to gasp from the sensation as she smiled sweetly.
“I’m flattered that I have this effect on you Rick” she said seductively
“Let’s see if we can take this a little further” she said, and gently she lowered herself down a bit so her weight pushed her pussy lips against my cock head. Her clenching lips resisted for a second, then yielded to her weight, and parted, allowing my cock head to slip inside her pussy.
My eyes popped wide open, as I gasped, my heart pounding. It was incredible, the sensation of her soft womanly flesh, grasping the sensitive head of my rock hard cock. I was in heaven and I wasn’t even all the way in yet. I had always fantasized about sex, imagined what a woman’s pussy would actually feel like wrapped around my cock, and here it was way better than I imagined. Every nerve ending in my cock head was screaming with excitement at the feel of her soft warm flesh grasping my cock head. Looking at her, I couldn’t believe that such a beautiful woman was doing this with me. Compared to the men should could have, I was just a boy, yet here she was, lowering herself onto my body, taking my cock inside her.
She smiled, at my facial expression, not in a mocking way, but in an understanding way. Leaning in she kissed me tenderly on the lips, then pulled her face back, and maintaining eye contact, released her weight slowly, allowing her to impale herself slowly on my cock.
As the grasping ring inside her pussy lips clung to me, I was overwhelmed by the sensation of her grasping pussy sliding over my sensitive skin, grasping my throbbing cock as it slowly engulfed it. The moment seemed to take forever, as the feelings took over my body. I couldn’t even speak, I just sat there gasping, barely able to breath as my wide open eyes were locked on her beautiful eyes, and I just accepted what was happening to me.
Slowly, as her flesh slid over me, she eventually took the whole thing inside as her buttocks pressed against my pelvis/thighs and her pussy grasped the entire length of my cock. I couldn’t move. I just sat there, panting, feeling my heart pound against my chest as I sat there captive to the overwhelming sensations assailing me. I had no idea sex could be so physically, mentally and emotionally powerful. In addition to the wonderful feeling of her pussy grasping my young cock, I had the feel of her soft skin against my body, her erect nipples brushing against my chest, the visual presentation of such a beautiful woman, her sexy perfume combined with the scent coming from her pussy. I never wanted this moment to end. Nothing in life would ever compare against this. Most guys would lose their virginity in a clumsy fumble with another high school girl, using a condom and here I was having the most intense sexual experience ever with the hottest looking cougar lady ever.........and I was only a high school kid! Doing this at my age......with this super hot looking goddess! Fuck!
I opened my mouth and was about to say something when she flexed her pussy suddenly, clamping down on my cock, causing me to gasp loudly instead of speaking, my back arching as my entire body jumped from the sensation. Maintaining eye contact she smiled sweetly at my reaction. I tried again to speak and she did it again, and again my words were lost in a gasp.
“Oh, I see you like that.” she said in a husky voice. Leaning in she kissed me on the lips, her tongue probing my mouth as I kissed back. Breaking the kiss, she mover her mouth slowly alongside my check, breathing lustily on my skin as her mouth approached my ear; As her lips touched my ear, I could feel her warm breath entering as her lips touched my ear, and my whole body quivered from the sensation.
“Oh, I’m going to enjoy introducing you to the ways a body can feel pleasure”, and with that she really clamped down, causing my head to jerk back as I gasped, more of a yelp while she threw her head back almost as though in victory, causing her hair to swirl wonderfully around her face.
Looking back at her, we maintained eye contact, which was in itself so intimate, enhancing the physical pleasure of the moment. Then she started to rise, raising her body as her flesh slowly slid off of my cock, gradually freeing it, inch by inch until only the head remained. She paused there, looking at me for a second and then she lowered herself onto me, slowly but assertively as her flesh slid over me again, causing me to moan from the feeling of her grasping pussy sliding over my cock, taking it in, massaging it as she went. Several times as she slowly took it in, she clamped, causing me to jerk and gasp as she did this until she was fully seated again.
Leaning in, she touched her nipples to my chest, her lips to my mouth and repeated the process, clamping her mouth on mine when I gasped, forcing a kiss as her tongue explored my mouth and our tongues danced.
Then she started fucking me. Slowly, but continuously as she slowly went up, pausing then down, repeatedly as her hands caressed my body, and mine hers, and we kissed romantically, passionately like lovers. I was having the most powerful sexual experience I think a guy could have and I didn’t even have my driver’s licence!
She rode me, slowly, rhythmically as I took in the sensations. Her body undulated erotically as she did this, and the visual of her movements alone were hot as hell, but the feel of her pussy grasping me, her smell, her touch and the taste of her mouth were just overpowering me. She was in complete control of my body and mind, and she knew it.
This went on for some time, her body moving over mine as she fucked me on the couch in her basement, our bodies moving against each others, our hands exploring. I started instinctively raising my pelvis up as we made love passionately, my hips coming up to meet her buttocks as she came down.
At one point she started brushing her nipples up against my face as she rode me, and I opened my mouth, taking one of the tender yet firm buds in my mouth and started teasing it, licking it, sucking on it.
‘Oh yes Rick....oh yes! Do that darling! Oh god you’re making me hot” as she started speeding up her actions, riding me faster now. The feeling of my cock, penetrating into her pussy, past those delicate lips and deep into her womanly body felt so right. I didn’t think beyond the present or anything else; just focusing on the fact that my most intimate body part was penetrating past hers, and was deep inside her body. Just the thought of it alone was erotic.
She started fucking me faster, riding me as my hands started grabbing her ass, feeling those soft yet toned lady buttocks. She started fucking faster, and faster, riding me aggressively. As our movements increased, she started to perspire, her body glowing with perspiration as the wetness of her skin shone erotically in the dim light of the basement. The sweat on her face, her breasts, her body was a visual picture of erotic perfection as she rode me. The feel of her damp skin against mine was even more arousing than it had been before.
“Oh you’re mine! I’ve claimed you as mine!” she said lustily!
I wanted to speak, but still was trying to just control my breathing.
She leaned in, her mouth close to my ear, her breath teasing it, as her lips gingerly brushed against it.
“Tell me you’re mine Rick! “
I took in a deep breath, and gasped “I’m yours”
“Call me Helen Rick” as she rode me like she was possessed, fucking me with hard aggression now.
“”I’m yours Helen” I gasped again
“Oh I love you Rick. You beautiful boy......I love you.....you’re mine. I claim you!” She moaned. This seemed a bit over the top but at the same time I liked it. She was better looking than any girl in my school.
“Do you love me Rick?” she asked, which caught me off guard, but then I thought, yes. Of course. She’s beautiful, and evidently loves me or she wouldn’t be asking.
“Yes” I gasped
“Say it!” she said insistently as she rode me harder
“I love you!” I gasped as she rode me faster, with almost desperate urgency
“Say it and call me Helen!” she moaned, pulling her face away from my ears, looking into my eyes.
“I love you Helen!” I said, sincerely. Hell yes I loved her. I had had a thing for her since I was in training wheels, and now she took my virginity, loved me. Heck, I didn’t care if she was using protection. I would marry her even, so lost I was in her beauty and tenderness. The thought even crossed my mind that I might impregnate her....and I liked it.
She smiled upon hearing the words, and started fucking me faster, harder, her body almost assaulting mine her copulation became so urgent in her need for release she rode my body hard, her tender womanly flower grasping my hardness as it went up, sliding almost all the way off my cock and then down, slamming herself down to be impaled as her buttocks slammed into my hips while she rode me.
All this was great but I was starting to come to the end. The feel of her soft delicate flesh sliding over my sensitive cock as she grasped me tightly with her inner muscles, the feel of her skin against me, her warmth, her scent, her beauty were all driving me to the edge and I didn’t think I would be able to hold out much longer.
“Oh Rick, I’m going to come soon...come with me! Come inside me!”
She didn’t need to encourage me at all. I was ready to climax and soon, the heat, the sensation, the intimacy of the moment and of course her tight grasping pussy, grasping me, sliding over my flesh drove me over the edge and I felt my orgasm about to start.
“Oh Rick! I’m coming!” she screamed as she pounded her body down onto my hips ferociously, and then suddenly my orgasm exploded ferociously, taking over my whole body as though every fiber of my being was having an orgasm, and I arched my back, throwing my head back as I gave myself to the sensation.
At the same time she screamed in heat; “Yes! I’m coming! Oh Rick” as she planted her body down hard, driving her buttocks down onto my hips as she engulfed my entire cock inside her and she kissed me hard on the mouth as we both climaxed simultaneously. My cock erupted inside her, spewing my semen up inside her as though with jet propulsion, as her pussy quivered and clamped down on me, while she kissed me as though starving for my mouth and both of our bodies quivered in excitement and heat as my fluids released themselves deep inside her body. We quivered like this for seemingly an eternity as our bodies felt the release they needed and then both of us sagged simultaneously, her hot sweaty body collapsing against my chest limply. Her pounding heart beat through her chest into mine as mine pounded back. My cock still twitched, sending residual spurts into her as her pussy still twitched in reflex to the climax it just experienced.
We sat there, our bodies and souls connected, as her tender delicate ladies body lay forward against mine as I sat back on the couch, my hardened flesh still inside her. I had just made love to a woman who had been in my fantasies since childhood. She had taken my virginity, and I came inside her body without protection, and it felt so right.
Finally she moved her head away from my shoulder, looking at me.
“Rick, I’ve been watching you for awhile now, and just knew you would be perfect for me” she said with sincerity, as I basked in the compliment. I was faintly aware of the fact that I was still inside her.
Leaning forward, she placed her mouth against my ear, and spoke huskily;
“I wanted you! I knew I had to have you; to take you, to make you mine! I just had to take you. I love knowing that you never had sex before me. I’m your first, your last,.......your only” she said lovingly as her mouth moved away from my ear, towards my neck.
I was in the process of wondering what she meant by ‘my last and only’ when her mouth seemed to clamp down on the side of my neck, and suddenly a piercing pain drove into my neck as she seemed to bite down with tremendous force. I jerked and tried to scream but my throat seemed to be unable to work, with steely prongs driven into it. I panicked in my agony, and struggled to throw her off, but her arms were like steel, pinning me effortlessly as they held me in place while she dug herself into my throat. She was a small woman, but she overpowered me like I was a child, and held me still as she bit deep into my throat. Terror gripped me, even more so than the pain. What the hell was she doing to me? I felt what seemed like two short fangs from her bottom jaw clamping onto my neck, while two long fangs in her upper jaw drove inside, tearing my throat, entering my windpipe, causing blood to spray inside as I choked.
Withdrawing the fangs, she released the hold on my neck, pulling her head back to look at me, yet her insanely powerful body held me in place. I could see now what my mind knew but tried to deny. It was a terrifying sight. Her face still looked mostly the same in all its beauty, but there were terrifying changes to it. First, her eyes no longer looked the same; they had changed colour to something much darker. Secondly, she had long fangs protruding from her mouth, and blood dribbling out of her mouth and down her chin.
I was terrified. I fought furiously against the steely arms pinning me down with ease. The pain in my neck, the difficulty breathing with my neck injury and the terror of seeing what a beast she was had me struggling desperately for my life. I wanted to live!
“Rick,...sweetheart, don’t fight it; your just making it harder for yourself. Give in, let it happen...it will be a lot easier for you that way dear; much easier. I promise, you’ll see”
With that she opened her mouth, and with a beastly howl, her face shot forward with almost blinding speed, and she clamped down on my neck, tearing into it painfully as I thrashed helplessly in her arms. Suddenly I felt something rupture in my neck, and could sense the blood suddenly flow like as though from a pump. I saw it spray on the part of her face I could see, and suddenly felt hot thick fluid spraying into my windpipe, filling into my lungs as I gagged and choked.
Her mouth clamped onto the opening in my neck and I could feel her sucking ferociously as though starving.
I fought back still, struggling as I gurgled blood, yet I felt my arms and legs rapidly weakening, as they started to go numb with a tingly sensation. At the same time, I felt my eyelids getting heavy as they fluttered, and my field of vision started to get spotty.
I felt my eyelids flickering as everything started to go black..................
