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Surprise for the Babysitter (me x TeacherSerena)

S

ShadowFighter88

Star
Joined
Oct 25, 2009
Location
Australia
Normally, I find a bath to be relaxing. That night; not so much. My parents had gone out to celebrate their anniversary and hired a babysitter. It wasn't the first time my parents had hired her for this; I didn't know it at the time but they were very sexually active people and couldn't really indulge at home in-case they woke me up.

In a way, it was the babysitter's fault for making my bath a bit less comfortable than normal; she was, to be blunt, drop-dead sexy and my wandering mind had conjured up all kinds of images of her while I soaked, leaving me with one hell of a hard-on. Now that may seem simply annoying to some of you; but I'm somewhat... gifted in that area. At full-mast, my cock reaches somewhere around the fourteen-inch mark (never bothered to actually measure it) and about two and a half inches in diameter. Stick that on a fourteen year old boy who was a bit short for his age and you might understand why an erection for me is a bit more than annoying.

I couldn't leave the bathroom like that since I'd have to walk past the doorway to the den (where my babysitter was watching a movie) to get to my room. So I did what any teenage boy with hormones raging more than a psychotic berserker who just found out his wife was screwing half the clan would do. I don't know how long it took me to 'work out the frustration' but I knew it was a temporary measure at best; I can recover surprisingly quickly and it would only take a few mental images of my babysitter to make all that work go to waste.

After cleaning up the shower, emptying the bath and drying myself off, I wrapped a towel around my waist and headed for my room. Out of curiosity, I glanced into the den to see what the babysitter was watching.

Name: Erik Reilly
Age: 14
Height: 5'
Hair: Dark and reaching to his waist
Eyes: One green, one blue
 
"It was just like any other sitting," I thought to myself. "I've done a thousand of these." I'm often called on to sit simply because I've never had a complaint about my skills; I like to think it's me but sometimes I would say the children I sit simply want to see me back because of my figure. I stand a modest 5'5'', but a chest at 36DD and an ass to match belie my height. I have no doubt that many of my sits have oogled me, but it's no thing to me.

I decided to spice up the night myself; while the kid will be in the bath, I decided to pop in my favorite porno. 15 or 20 minutes would give me more than enough time. As soon as he headed up for the bath, I reached below my skirt, playing the movie as I began to play with myself. 5 minutes in, still no climax. ten in, still nothing. This may have been pushing it, but I decided it was not going to cause any problems. I continued to work myself, not noticing the silence of the shower being turned off as he finished.
 
Looking into the den, I stopped in... well not quite shock, more like a strong surprise. There on the big screen was a porn film and my sitter was on the couch, masturbating. Needless to say, my bit or relief earlier was now a total waste as I felt blood surge into my cock, causing it to start tenting the front of my towel.

I stayed quiet, mainly to watch both the movie and the sitter, but also because I was worried about getting caught. Judging by what was happening on the screen though, I started wondering if she liked 'well-equipped' guys; the one in the movie was impressively above-average, but I was still larger then him by several inches (or at least that's how it looked, there wasn't exactly a ruler in the shot for me to check).
 
She began to get into it. Slight moans escaped her lips as the action in the movie escalated. She leaned back slightly to facilitate her actions. She pulled her shirt up slightly, toying with her breasts. She was unable to hear anything over both her sultry moans and the grunts of the actors in the movie. The movie was only halfway over; she was hoping that the kid had finished his bath and gone to bed. Sadly, this wasn't the case but she was unaware. She closed her eyes, leaning her head back as she continued to probe herself.
 
I started squeezing myself through the towel to get some relief as her moans turned me on even more. The gap in the towel (where the two ends overlapped) was soon parted by length as it reached full size. I wanted to just beat off right there, but the resulting mess would be hell to clean up and the less my parents knew about this the better. Plus my parents had their porn stash in the den too and I knew which cabinet it was and it's not secret that I can pick locks, so it wouldn't take Sherlock Holmes to reach the obvious conclusion to finding cum stains on the floor of the den.

Instead, I just continued squeezing the base of my shaft and occasionally by heavy balls too. I was torn between going to my room to jack myself senseless or staying there and seeing what happened.
 
The porno began to reach it's climax. She worked herself hurriedly, hoping to be done as soon as possible. She pulled her shirt off fully, tossing it behind her (in the direction Erik was standing, no less) leaving her in her bra. Her skirt soon followed, following the same flight path as her shirt. She gripped and groped her breasts as she pressed three fingers into her. After a minute or so of this, she moaned out in orgasm, slowing down as she was panting heavily. She turned the tv down as she caught her breath.
 
I was surprised when she tossed her shirt and skirt off but was too stunned by the situation to move. Her shirt landed on the floor beside me, but the skirt ended up hooking over my cock, like that ring toss carnival game. Before I could think of what to do, I heard her moans reach their peak which just made my cock harder and leave me stunned, no idea what to do.

Considering how the rest of the night went, it's probably a good thing my normally quick mind decided to take the night off.
 
She got up slowly, stretching her arms out. She turned the tv back to regularly scheduled programming before turning around to grab her clothes. Before she even finished her rotation, she stopped. She saw him standing in the doorway, wearing only a towel and her suspended skirt. She didn't know what to say. She stood there shocked for what seemed an hour. After the awkward silence, she mustered up the courage. "What are you doing here...? weren't you supposed to go to bed?" She said, her voice quivering (possibly from her recent orgasm).
 
"I was wondering what you were watching." I was surprised at how deadpan I sounded, I think my brain was still having trouble processing what was happening. I'd just caught Serena mastubating to a porno and she was now standing in-front of me wearing nothing but a bra while I was standing in the doorway with just a towel on and her skirt hanging from a cock that looked far too large for someone my age and size to have, the base of which I was still idly squeezing without realising it. I'm not surprised my mind was still scratching its head about what to do; it was an impossible situation that I didn't think happened outside of erotic literature.
 
She paid no mind in attempting to cover it up. She slowly walked over, her large hips swaying seductively. She stood just a few feet in front of him, leaning over slightly. "Now, I understand you're a bit shocked right now. I just need you to not tell your parents about this, okay? I don't care if you tell your friends or whoever, just not your parents." She stood back up, smiling, almost sure she would take her request.
 
I tried to keep my eyes on her face, to show I was serious (not an easy task, believe you me). "Don't worry; if I told them, they probably wouldn't hire you again. I'd probably get stuck with some dottery old woman as your replacement." I smiled. My brain must've sorted itself out by then if I could make a joke.
 
"Good. Besides, that's probably the coolest thing you will ever see your babysitter do." She reached down, grabbing her shirt from the floor. "Hold still for just one second, I need to grab my skirt." She didn't seems to realize how it was suspended in mid-air, but she paid no mind to that. She grabbed it by the waistband, pulling it from him. Her eyes grew big as the skirt no longer blocked him. "Wow."
 
"And the only time I'll see it, I assume?" I said before she picked up her shirt. As she reached for her skirt, I held still like she asked and wanted for her reaction. How she didn't notice my size before removing the skirt, I don't know, but she certainly noticed it now. Without the skirt weighting my length down, it rose up until it was a bit above perpendicular with my body, jutting out just over a foot and feeling as hard as it had ever been.

Whichever way the rest of the night went; I knew I'd need a lot of release from this.
 
"we'll see, we'll see." She was still shocked at the size. "it's that big? Really? How do you keep this hidden...?" On one hand, she was strangely attracted; on the other, she feared for her job. "Now, I need you to promise me, really. You aren't going to tell your parents, right?" She held out her pinky, thinking a pinky promise still meant something to kids his age.
 
"With sturdy, long pants and a lot of mental discipline." I couldn't help but be a little snarky with my reply. Wise-ass comments seem to come naturally. Probably from all of the old british comedy shows I watch - Blackadder, Dad's Army, Red Dwarf and so on - which use snarkery a lot.

When she held out her pinky, I placed my hand over hers. "As far as my parents'll know; I went to bed right after my bath." I smiled before continuing. "And like I said before; if they stopped hiring you I'd probably end up with an old hag with a stick up her arse instead. The sort who'd insist on using iodine if I cut myself with a craft knife like I did last week."

Me and dad both play a tabletop wargame called Warhammer 40,000 and I'd been putting an Assault Marine together last week while Serena was babysitting when the knife slipped off the part (I was shaving off pieces of the frame that were left on the part) and gave me a nasty cut on my finger. It wasn't bad enough to go to the hospital with, but it did look like it was going to scar.

((OOC: True story that; started collecting models for the game a few weeks ago and cut myself like that on one of the Assault Marines. Don't know if it'll scar but it wouldn't surprise me. What was surprising was that there wasn't any blood on the knife so it must've cut pretty cleanly. Not bad for a $8 knife I got from Toyworld.))
 
"Well now that I have your word, I suppose I can show you another reason why I'm always coming back to the same houses all the time." She pulled his hand away from his monstrous cock, grabbing the base herself. She lightly licked the tip, her tongue darting around the head. She lifted his huge rod, running her tonuge the full length on the underside, stopping when she reached the top to go back down and suck on his balls a bit. "This is why you can't tell."
 
My cock twitched as she wrapped her hand around the base and it felt like a lightning bolt shot up my spine as her skillful tongue went to work, precum already drooling from the tip. I placed a hand on her head, not to guide her but just because I felt I had to do something beyond stand there.

"As long as this isn't a one-night thing." I joked. I wouldn't tell even if this was only for one night and I'm sure Serena knew that.
 
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