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A Lesson in Babysitting (Tyr & Katy108)

RE: A Lesson in Babysitting

As she sat on the chair, giving the blonde man opposite an unobstructed view of her pussy whilst her left foor moved between his legs, two things happened and one didn't. At least as far as Jenna could see, no-one else happened to see what was happening or the state of her undress and for that she was grateful. She wasnt sure how long that would continue. Of the two things that did happen, the first she was expecting. She felt embarrassed. She had never been this forward with a guy before. Hell she'd never been forward with a guy before. She always waited for them to come to her. This was very different. Jenna felt cheap. She felt like a slut which of course was completely in keeping with how she was now dressed. Her mind drifted back to the previous night for a second. Jack had said she was already his slut. What she was not expecting was to find that she was feeling turned on by what Jack was having her do. She didn't know whether it was the fact that she was doing what she was told or if it was what she was doing and where, but she could feel herself getting a little more turned on as each moment passed.

Her thoughts were interrupted as the man opposite her shifted in his seat. She looked up to see that Jake was now waiting again to see the second pair of shoes. She stood up, pulling the hem of the dress down again and made the same back and forth walk, letting Jake see what it was he was 'creating'. But when he indicated for her to go to him, her body tensed and she wondered exactly what it was he was going to have her do now. She was a little scared, and as much as she might try to deny it even to herself, she was a little excited too. When he told her, she froze for a moment and slowly looked up at him. How was she supposed to do that without anyone else seeing? Without the short dress revealing everything? As she turned around still a little stunned, she felt the playful slap on her ass.

She sat down. The man opposite looked at her, up to Jake who was already turning away, and then back to her. This time he had a slight cheesy grin on his face. She looked back at him and smiled nervously. She let him undo the shoes. As he slipped the left shoe off, she brought her left foot down to the floor a little wider than she would otherwise have done. As soon as he lifted her right foot to undo the shoe, he immediately had a view of her pussy. His smile broadened a little as his gaze flashed over to Jake, who still didn't appear to be paying any attention, and then back to her and her pussy. As he looked back, he saw her hand sliding slowly up her thigh, moving the hem of the dress up as she did so. It was impossible to do otherwise. The man reached out for the final pair of shoes without taking his gaze off of the point between Jenna's legs.

As he picked up the shoes, Jenna brought her right foot back to his bulging crotch. Moving her foot gently back and forth, scrunching her toes, the spreading them out, caressing and gently massaging his dick, feeling it responding. At the same time her own fingers reached her pussy. She couldn't believe how wet she was. She sighed softly as her fingers slipped between her pussy lips and she leaned back onto her other hand. As she looked across at the blonde, she chewed her lower lip and moaned softly
 
RE: A Lesson in Babysitting

From a rack of clothing at a safe distance John could see the young woman move and arch her back giving the young man an excellent show he hoped. Not really caring about the show as much as her compliance with his request, he moved off so they would have a moment without him spooking the boy. Not only was he trying to draw Jenna out, but each of the things he was having her do, would hopefully get her hotter and more bothered, which he felt would help reduce her resistance. Still she was proving to be a very special young woman, and was pleasantly surprising him.

Johnny tried to as much as he could inconspicuously shift his leg and relieve some of the pressure from his member going down his pant leg. Yet, again the sexy woman, for she was no girl did a show for her man, but it seemed like in no time she was again sitting ready for him to remove the second pair and put on the last. The older man she was with seemed yet again to move off, which pleased Johnny but so to he was so unsure what he should do. That decision of course wasn’t his to control, as he lifted the last pair out of the box, and prepared to put them on the long toned legged woman.

The young woman gave him not an accidental glancing view of her sexy pussy, but a complete unobstructed presentation of it. There was no doubt in Johnny’s mind that the old guy was the money, and that this girl was prowling and playing with guys her own age. Still there was nothing he could do about it here and now, and not possible loose his job. Feeling a little more confident, he started to put the shoe on slowly letting his hands caress her ankle and lower calf as he did so, with the older guy off in some other part of the store he felt this would at least indicate his appreciation and interest in her. So he muffled a groan when her foot again gave his trapped length attention. All of this would have been more than sufficient to make this the best shoe fitting experience in his life, but what blew him away, was her hand sliding between her legs. Johnny couldn't help but gasp in shock as she begins to play with herself. A large smile plastered across his face as this wondrous sight presented itself, though the more bold her action, the more shocked he was. His young body just froze, he didn’t know what to do, and he’d never met a woman of any age that was this bold or this confident. Johnny’s limited experience showed, as he just squatted there staring mesmerized by Jenna’s actions, his mouth agape.

The only thing causing him to pull away, was the fear, that if she kept up even a little bit more than he would cum in pants. With great reluctance, he helped place the last shoe on her remaining foot. In the distance Johnny could see the older guy meandering back, obviously in no particular rush.

Ahhhh… ummm…. Ahhh.. wow, ahhh does … is that okay?

The words Johnny said just sort of fumbled out as he tried to say something, anything.
 
RE: A Lesson in Babysitting

Jenna drew her finger back and forth in the folds of her pussy. She would circle her clit and then slip her fingers down, before drawing the back up. she moaned softly and in time with the movement of both her hand and her foot. She could feel her sense of arousal getting a little stronger but her mind was thinking more about Jake than it was the blonde man opposite her.

Then she was suddenly aware of him standing up, coughing, stumbling over his words. For a moment she thought perhaps someone had seen; another customer? A boss? But when she removed her hand, fingers wet, and stood up quickly. But all she saw was Jake approaching from a short distance. She smiled at him sheepishly, asked what he thought of these shoes and then asked what his preference was.

The blonde stepped back a little letting the woman's 'sugar daddy' (or so he thought) move in. Jenna was more than aware now of both of them staring at her. She kept tugging at the hem of the skirt as she moved a little left then right. And she waited for Jake's approval.
 
RE: A Lesson in Babysitting

Johnny saw the older man rounding the corner, and not wanting to get the sexy woman in trouble he stands, using the box as cover for his condition. He was jealous when her attention quickly turns to the older man and gets his opinion on the shoes. What the fuck did she see in that guy? Shit he was probably old enough to be her father. Yeah he looked big and built like brick house, still it wasn’t fair. Johnny retreated to the little check out area with the boxes, using the counter for cover. Jake gave Jenna a smile as she approached.

You look hot! Let’s get the dresses and shoes and get out of here. Oh and I found a few more things for you while you were trying on your shoes.

There were some clingy tops, short shorts, and other items that left little or nothing to the imagination. Jake whipped out his platinum card and quickly paid for all the items, not in the least concerned about the price, the results were all that matter to him. Before Jenna could return to the changing room, he let her know what he expected.

Leave the dress and the shoes on.

There was no need to have her change back into her old clothes, as he planned for this transformation to continue, and the outfit was just the first part. The prior cloths represented her normal collegiate look, and the new ones as his personal possession. Her new attire now selected to show of as much of her gorgeous body as possible. Jake felt no jealousy that other men or even women would ogle or be jealous of her, because he was showing her off on purpose, letting others know what he had.

Anything else here you think might go nice with your new outfits?

If so he would purchase them, but either way he would again take her into his arm, his hand holding her close, as they made their way to the car and their next stop. The young man having slipped his phone number onto a card into one of the shoe boxes, hoping he might get lucky.
 
RE: A Lesson in Babysitting

As Jake complimented her on the shoes and on how she looked, she just smiled and nodded and gave her thanks. When they were stood at the cash till, she stood close to him, but occasionally her gaze fell on the blonde. She was imagining what he was going to be telling his friend that night and probably tomorrow and again the day after. Even though she obviously didn't know who he would be telling but she felt a tinge of embarrassment nonetheless at the idea of him telling them about the real slut who had bought shoes today.

When Jake told her that she didn't need to change back, she couldn't help but see the young man lift his head. Obviously the all now knew that she would be walking out of the shop and then who knows where with no panties covering her now wet pussy. But she said nothing and when he asked if she could think of anything else.

"Not that I can see. And thank you for buying these for me."

Once the bill was paid she walked again in the curve of his arm. And now she did start to notice the look from an odd person here or there. Usually the looks from women were frowns...disgusted or shocked or contemptuous...and that was without knowing she had no underwear on. Men who noticed her generally seemed to have a bit of a grin on their mouths and most of them didn't make eye contact with. As they looked she pressed a little closer to Jake. There were both quiet as they headed back to the car, Jenna having no idea as to the next stage of the journey
 
RE: A Lesson in Babysitting

The trip to the car was short, and all the new clothes quickly loaded in the trunk. Opening the door for Jenna, he held it till she got in, then Jake quickly moved around to the drivers side and got in. In Jake’s own strange way he was appreciative of a woman, that wasn’t afraid to be a woman. The next stop was across town, so he had some time to play with Jenna on the way there.

You did well in there; I think you made the boy’s day!

John casually said as he started the car pulled out of the parking lot. Once he’d pulled out into the main street, he left on hand one the wheel and the other on Jenna. The top down, the cooler air going by on a hot day.

Did you enjoy it, my dear?

Even as Jake asks the question of her the hand on the top of her legs begins to delve lower, and moves deeper between her legs. The hand quickly coming in contact with the hem of her short skirt, and begins to push it up as he is obviously physically confirming the fact that she enjoyed it or not.
 
RE: A Lesson in Babysitting

She went to get into the car foot first... they way she always got into a car. But then she remembered and smiled sheepishly at Jake. She turned a little to face him as he held the door open, then after straightening the skirt over her rear, she sat down. Only then did she lift her legs into the car. She watched as Jake closed the door and then turned her head to look at the driver's side, waiting the few seconds until he climbed in and was settling himself in. She couldn't help but giggle a little at the idea that she had made his day.

"You realize he's going to tell all his friends... for days." Jenna looked down as she felt Jake's hand placing iself on her knee. The Z4 was not a big car and her knee was a comfortable reach for him. His hand felt good. Just as she had last night, she liked the feel of his hands on her. She looked back up at him and asked where they were going next. Jake acted as if he hadnt heard her and simply asked if she had enjoyed her time in the store. She paused for a moment. Had she enjoyed it? She'd spent a lot of the time scared that someone would see; a lot of the time scared that the assistant would make some scene over what she was doing. But towards the end of the whole experience she had started to realize how sexually excited the activcity had made her. As she sat thinking, she felt Jake's hand moving up her thigh. She looked down at it again and this time her knees parted. The fact that the skirt of the dress was so short meant that there was nothing to cause any restriction. Her knees spread. Her thighs parted. Jenna sighed softly and looked back to Jake.

"I think so... it was... different."
 
RE: A Lesson in Babysitting

Jenna gave no resistance that he could tell as she naturally spread her legs and gave him full access. So they spoke as the buildings passed by, other vehicles went about their day, no one but the two of them knowing what was going on in the car. Well maybe no one except the large delivery truck that could look right down into the small sports car, its drivers attention drawn to the lovely woman sitting in the passenger’s side. Pulling right alongside the rough looking driver couldn’t help but stare down smiling at the show.

You shouldn’t worry, men love when a beautiful woman who gives them some attention.

Jake's reaches between her legs, and is happy to feel her dampness, and know that what had happened caused her arousal. It just further cemented for him that she had strong sexual desires that just needed to be drawn out. So his skilled hand worked her wetness as the large delivery truck pulled alongside, Jake's eyes naturally and briefly drawn to it, saw were the drivers attention was and smiled. His hand pulled her short dress up a little more, not only to give himself more access, but to make sure the that he wasn’t the only one enjoying the show. Jake loved when other men drooled at his possessions, for him it was an ego boost; something about flaunting it thrilled him. That at this moment the item in question was Jenna just made it even better. As the traffic moved along, Jake made sure his vehicle stayed right alongside the delivery truck as his experienced hand went to work.

That’s good! I’m glad you are willing to try different things, not afraid to take risks and are open minded. You need to learn to enjoy your body, and let others take pleasure in everything you have to offer.
 
RE: A Lesson in Babysitting

Jenna stiffened a little as Jake's hand reached her pussy and she gasped softly. Her legs opened wider and she sat a deeper into the seat. She let her head fall back for a moment, her eyes closing as she felt his fingers working and she sighed, her hips very slowly moving forward a few inches and then back. Her activities in the store had already started to excite her and so her natural reticence and shyness was already weakened when Jake started to play in the car.

Jenna felt the skirt of the dress being lifted further and she smiled and opened her eyes again as Jake's hand returned. Perhaps it was the noise; perhaps it was a shadow, but something made Jenna look to her right and without really thinking, almost nonchalantly, her gaze drifted up. And then her body really did tense.

"Oh God... Jake... the driver..." She closed her legs about Jakes hand and turned her head sharply to look at him, her cheeks flushed with embarrassment. "...he can see what we're doing." Jenna had put her left hand onto Jake's wrists, partly holding it, partly trying to pull it back. Jake didn't do anything. His hand stayed where it was. His fingers kept moving. Jenna looked back around and up at the truck driver, this time noticing his somewhat dirty grin as he seemed to chew slowly... maybe gum or chewing tobacco.

"Jake... we should aahmmm... maybe we should stop... or aammm... or let him pass."
 
RE: A Lesson in Babysitting

Jake’s fingers never slowed or stopped as Jenna might have wanted or at least professed. Though Jake could not really look and see Jenna’s nervousness and embarrassment, her voice clearly indicated her discomfort. The anxiety and stress were just something she was going to deal with, thought Jake’s opinion as he continued to have his hand and fingers invade her most private of areas.

So what, he can see? He’s just watching.

Now Jake could have given her a way out or offered her an opportunity to escape the situation, but he didn’t. He didn’t even give her a choice as he issued his next command.

Open you legs. I want him to see that I’ve got the sexiest woman he’s ever seen with me. That way he can go home to his wife or girlfriend tonight and close his eyes while he fucks her while thinking about you.

Open up wider!

The tone wasn’t harsh or mean; it simply was a forceful command that came through with strength when Jake’s deep voice said it. Jenna was going to learn that she wasn’t only his girl, but also his possession to be shown off and used as he saw fit. Jake’s large hand continuing to rub her wet slit and clit, even moving partially out of the way so the guy in the truck got even a better view.
 
RE: A Lesson in Babysitting

She was a little surprised by Jake's reaction...or lack of it. So what? So what? Just watching? He could see practically the whole of her upper thighs. He could see where Jake's hand was. He could probably guess what was his fingers were doing. His fingers did feel good though and despite her concerns about their voyeur, and Jenna couldn't help but moan again. Her hand didn't let go of his wrist but she stopped any attempt to push it out of the way... And slowly in response to his instructions, her legs opened wider.

She dropped her head and closed her eyes, trying to push our the fact of the truck driver out of her mind. Focus on Jake...on what he was doing. But after a few moments she realised she couldn't and that in truth the strangers presence even in the truck added something to everything that was happening. Every emotion and sensation seemed heightened in some way. What the he'll was happening to her? Had Jake brought about this change in her? Was he just bringing a part of her out to the world that really was there all along? What had he said last night ... Already her his slut.

In response to the repeated instruction Jenna opened her legs wider still. She had no idea what the truck driver could or couldn't see, but surely it can't have been that much.
 
RE: A Lesson in Babysitting

The man was almost hanging out the truck window, watching the spectacle going on below him, a big smile on his face. What he could see was in actuality very little, but it was more than enough to know exactly what was going on. The hot number in the red dress spread her legs and gave her guy even more access, and from where he was looking down, the dress barely covered her hot body, and now even less. When ever he could his hand was between his legs rubbing his swollen length through his work pants.

Jenna didn’t say a thing, but her body for a moment hesitated, before she complied with his command. Her glorious sexy legs spreading, opening for him, her body made even more available to him. John could just barely hear the soft moan the slipped from her lips as she enjoyed the effort of his fingers upon her heat. The young woman probably never imagined or conceived of such a thing before, but as he guided her along this path, each step taking her a little further forward than the last. They came to one more light; soon Jack knew he would have to turn and this little festivity would be over. Still it left him just a little more time, to get the maximum effect out of it while he could. So while at the stop, John gave maximum effort to giving Jenna some serious attention, knowing she was being watched. Once at the stop, he could see that she had her eyes closed and was getting pleasure from it.

Open you eyes, and look at him. Let him see how much you are enjoying it. How much you like it. How much you want it.
 
RE: A Lesson in Babysitting

Janna"s moans became a little louder, a little more desperate and needy. As limited as her movement was in the seat of the car, her hips did move a kittle back and forth against the movement of Jake"s fingers. As she moved, her body slipped down in the seat allowing her legs to open wider still. The voice of the 'old' Jenna spoke softly in her head questioning her actions, telling her she had to stop. But that voice was being almost drowned out. She didn't want Jake to stop and the fact someone else was watching didn't matter. A particularly dark voice in her head was even telling her that the fact that someone else could see...knew what Jake was doing...knew what she was...made it even better.

At Jake"s instruction she complied. Lifting, tipping her head back to rest on the seat behind her. Opening her eyes. Looking at the man. Making eye contact as she chewed on her lower lip. Without really thinking her right hand moved up to her right breast. She caressed and squeezed her tit through the fabric of the dress, all the time looking at the driver. All the time her climax building.

"Oh god...mmmmmm....yes...I want it Jake...please don't stop...I wanna cum..." She saw the man smile as she spoke. Either he could hear her over the noise of the traffic or he could lip-read, but he seemed to know what she said. And he certainly recognised the moment that he did cum... Her eyes closing tight, a long moan louder than any before, and her legs closing tight around Jake's hand, the hand she was now holding in place between her legs.
 
RE: A Lesson in Babysitting

The driver of the truck had seen a lot of crazy shit, but the young woman with the dude’s hand between her legs ranked at the top of that list. The stiff rod that ached in his pants let him know just how much he enjoyed the show her and her man had put on. Unfortunately though not unexpected, the fancy sports car, turned at the next light, the guys hand raised above his head and waving good bye as he sped off. What he would have given to have a girl like that, the dream of every guy.

Jake’s wet hand briefly withdrew from between Jenna’s legs as he waved and turned leaving the truck and its driver behind. Finally he lowered his hand bringing it to her mouth for her to suckle on, his wet fingers lightly and affectionately touching her lips as he sped down the last street to his next intended stop. He pulled his hand away as her, as he had to make the turn into the parking lot. The building was a windowless retail store in a mediocre part of town, the signage outside clearly indicating that it was a store selling adult products.

You were amazing! I think that’s one very happy driver.

Jake parked and came around, helping Jenna out of the car. Taking her again into his arms, he pulled her close as he escorted her to the glass doors that had blackout windows. The large building inside was divided into various areas holding similar types of products, a candy store for those interested in adult play. There were mostly men in the store, though a few women were there too, most of the men trying to look inconspicuous as they shopped for things. Jake seemed little concerned that others would see him, and smiled at one of the attendants as he strode in with Jenna. Even though Jake was tall and broad shouldered, most the eyes followed Jenna as Jake led her over to an area that had various pieces: dildos, vibrators and butt plugs, along the way he picked up a shopping basket. Standing close to her, Jake couldn’t help but smell the aroma of sex wafting from her, as the young woman, hadn’t had any opportunity to clean up or wash. The smell was invigorating as Jake looked through the various devices.

See anything you would like? How about this one or this?

The matter of fact tone he used, and the way he appeared not in the least nervous as his hands shuffled through the various products, extracting a nice colored dildo and clear butt plug.
 
RE: A Lesson in Babysitting

Jenna sat in the seat,bhead back, eyes closed, letting her breathing settle. She wasn't aware of the truck driver waving as the two vehicles went their different ways and but for Jake removing her hand from between her legs she wasn't really conscious of Jake's acknowledgement of the truck driver.

When she felt his fingers at her lips however she instinctively opened her mouth. Without giving it any thought whatsoever she began to lick and suck on the gently, letting Jake move his fingers presenting them in different ways for her to lick, or to slide into her mouthbto suck softly. There was the merest hint of his cologne but predominantly of course all she could taste was her own cum. She only really became aware of her surroundings as Jake withdrew his fingers and turned into the almost deserted parking lot. She couldn't help but smile though as she climbed out of the car hearing Jake's comment and as before, when his arm wrapped around her, she settled comfortably as they worked. She had absolutely no idea where they were going and when they stepped into the store, she was genuinely surprised. She had never seen anything like it.

Some of the things on display were a complete mystery to her. Others she knew what they were but she'd never used anything like them before...or had them used on her. She was conscious of eyes following her as she and Jake moved steadily from one aisle to another. When Jake picked anything up she shrugged a little.

"I... I dint know. I... Guess...whatever you think."
 
RE: A Lesson in Babysitting

Smiling Jake continued to slowly fill the basket, getting some batteries, cream, an egg vibrator with remote, lube and lotion, as he moved around the store. Guiding her over to the clothing section, which had even more risqué items than the prior store, and most were made with a minimalist in mind. The first thing Jake moved toward was a spot that had lots of articles of clothing in leather. He found a nice leather collar, and took it off of a hook that it rested on, then handed it to her.

Put this on.

It was a statement calm but commanding, as almost all of his were. It was obvious that he was selecting and determining how she was to dress and to act. The choice he was making, made it clear that he had a specific vision of who and what she was going to be. While she was putting on the collar, he found a pair of small leather panties and bra, and tossed them into the basket. When he was done, he turned back and looked her over, the black leather contrasting nicely with her dress.

Excellent, I like it.

The shopping continued as he picked up a leash and tossed it in the basket, the basket now had a wide assortment of adult items. Another collar was tossed into the basket, as they moved through the store. Eyes were still following them, watching from between the racks and shelves as they moved around. More than a few had the glint of hunger in their eyes.

Is there anything else you’d like to try on?

There was a small room in the corner set aside, for changing, and Jake was ready to guide her that direction. Though this time he planned to follow her into the small enclosure.
 
RE: A Lesson in Babysitting

Jenna stayed close to Jake as they went from aisle to aisle. As the minutes past she became a little less self-conscious of where she was and of what she was looking at but most of it she had only seen in pictures or porn movies if at all. As Jake picked up each item and placed it in the basket, her gaze followed it. She was pretty sure she knew what everything was and she couldn't help but think about how and what she was going to feel when they were used at some point. When Jake handed her the collar, she was a little surprised. She hesitated for a moment and then reached out her hand and took it tentatively.

http://www.leatheretc.com/Merchant2/merchant.mvc?Screen=PROD&Store_Code=LE&Product_Code=5465Collar-Bkpt&Category_Code=Bondage_Collar

She looked up at Jake but he was already selecting other items for the basket. She brought the collar around her neck and secured it so that it was possible to perhaps squeeze one finger between it and her neck. She liked the way it felt around her neck. She felt her cheeks flush a little as she looked around nervously and saw one or two people watching her. She smiled when he finally looked at her and gave his approval before moving on. She followed dutifully. This was definitely not what she had expected. Last night had been... it had been the best fuck of her life but she had never thought that... She took a breath and exhaled slowly. She didn't really know what she was getting herself into her, but for the most part, she didnt care. It was exciting. Yes she was a little nervous, scared maybe. But it had been the best fuck of her life and Jake made her feel like she needed to be fucked like that every time.

As her gaze moved around the store and the shelves, occasionally she met the looks of others. She smiled nervously and looked away quickly, moving a little closer to Jake. Suddenly she was aware of him talking to her again.

"What...erm... no... I mean.. whatever you'd like... is fine." Her smile broadened a little.
 
RE: A Lesson in Babysitting

Jack smiled at her rather vague answer and acquiescence to his question.

Be careful what you agree to, I have a wide range of desires.

Guiding her to the small room set aside for changing, there were the normal various warnings about theft and such. Inside the small room were a bench, several hooks and a small full-length mirror on one wall. Jake set down the basket, and took a moment to enjoy Jenna’s new collar. Even as he speaks he pulls her into his arms, his arms wrapping around her.

I don’t know about the other people, but I’m having trouble keeping my hands of you.

Jake's hands hold her tight against his chest and loins, as he kisses her. The fingers press into the soft thin material of her clinging outfit. Even as he held her, his hand lifted and gently pulled at her outfit, till he’d raised the lower part up and about her waist.

And lately you seem to be having all the fun!

The hands that had been lifting her outfit, now slide down and over the smooth skin of her behind, the fingers kneading the firm flesh as the go.

So let’s see how you look in some of this other stuff.

Though the statement seemed nothing out of the ordinary, many of the items within the basket weren’t something one normally would wear, though that was exactly what Jake intended by the comment.
 
RE: A Lesson in Babysitting

Jenn smiled at him and then gripped his hand tightly as he led her to the changing room where she was surprised twice. Firstly she was surprised that he had come into the changing room with her; it made the whole thing seem somewhat illicit... or perhaps more illicit was more accurate she thought, in light of the kind of store they were in. Secondly, whilst it was small inside, she was still surprised at how much space there was. She was looking around the place when she felt Jake suddenly grab hold of her and pull her towards him. She squealed a little and then giggled as she lay her body against his. She wrapped her hand around his waist and kissed him back, moaning softly into his mouth as she felt his hands on her ass.

He was right of course; she had been having quite a lot of fun but she was pretty sure he quite enjoyed having her play the slut in front of strangers.

As he suggested that she try on some of the things that were now in the basket, she simply continued to kiss him and nodded her head briefly. Then she stepped back and wondered what it was he wanted to see her putting on
 
RE: A Lesson in Babysitting

Jake was almost reluctant to let the sexy thing out of his grasp, but he wanted to continue with her education, because that was what it was. Jenna had shown potential, but he needed to work on drawing it out of her and to increase her need. What he hoped to do was keep her in an elevated state of arousal that would assist in breaking down whatever walls or resistance she still had left. Fearful if he did it all at once she would bolt, so he was slowly ramping it up, pushing her to go further. Smiling he turned to the basket and popped the little egg shaped vibrator out of his plastic container, and installed the batteries, that he'd picked up. Smiling at her he held it up for her to see.

I thought I should give you something to remind you of me while we shop. A little gift that will just keeps giving. Now spread your legs sexy.

The device had a thick soft string handing from it, as Jake cupped it in his hand. Stepping up to her, he brought the hand holding the devices up and between her legs. Even before his hand reached its intended target, his other hand reaches around behind her neck and pulls her face closer to his. Jake’s mouth opens to kiss her passionately as his hand begins to slide the device up and into her pussy. His finger gently nestling the egg in, then pushing it deeper, as his tongue slips into her mouth. Jake didn’t ask her if she wanted this intrusion or what she thought, he just did it. Once it was far enough in, it wouldn’t slip out, his hand withdraws, only the string left to show something was buried in her, and he puts his hand into his pocket, and tests the remote control on a low setting.
 
RE: A Lesson in Babysitting

Jenna watched him as he pulled something out of the basket. She couldnt deny that she was somewhat excited. After the guy selling the shoes, then the trucker, then wandering around the store, the collar... it was all beginning to make Jenna a little... heated. After the car journey, she knew obviously she was wet but it wwasn't as if the stimulation had stopped then... it had just become more mental than physical.

Her gaze shifted to the small egg as Jake took it out of the wrapper. She smiled a little but then looked up to him. "You want me to... here ... now... I... I thought that was for... when we were home... "

As he stepped closer to her though she moved her left foot wider without him having to say anything. And then as he pulled her back into him again, she forgot about the egg... just for a moment. She moaned softly as he kissed her; Jenna opened her mouth immediately to him, and then she feels it. She groans, louder this time, although still muffled by the kiss. She kisses him back more earnestly, hungrily, whilst at the same time pushing herself down a little onto the egg as Jake pushed it up.

When it sparked into life it took her somewaht by surprise and she gasped, closing her eyes as she felt it buzzing deep inside her wet cunt.

"ohhhmmmmmmmmm"
 
RE: A Lesson in Babysitting

Jake smiled and kissed her, as she moaned, his lips aggressively kissing her. His mouth sucked on her lips, only broken by his delving tongue exploring her mouth, as he shared in her reaction to the small device buried between her legs. Jake left it on a low setting, not yet wanting to increase it, knowing he had plenty of time to do that later. The kiss finally broken, his large hands move to her waist and turn her around. As he talks one of his hands presses against her back, and the other explores her backside.

Now bend over a little bit … a little bit more.

The strong hand reaches down the backside of her leg and rises up, as he plays with her. With her dress still about her waist, he can easily see her glistening slit, and the moisture clinging to it. The strong and not unpleasant aroma of her desire caresses his nose as he brings his hand up higher.

Have you ever had a man make love to your ass before?

Even as he said it, he kneeled down behind her. His two large hands, spreading the cheeks of her ass. The intensity of kisses he had just administered to her mouth, now trailed down and over her ass. Soon his tongue was sliding between the cleft of her cheeks, till it began to gently lick her backdoor. His warm wet tongue circled her little puckered portal, plying it with attention. Jake's hot breath gently brushing past as his tongue slowly pressed against her asshole.

Leaning past her he picks up the bottle of lube, applies some to his fingertip. Then he quirts some at the top of her ass crack, knowing where it would natural flow. While one hand slides up from the bottom of her ass, to meet the slowing sliding lubricant. The fingers intentionally seeking the small puckered opening of her ass that hid between the two luscious firm sexy cheeks.

Have you ever had a man fuck you in ass before?

The lubed fingers slide over her little soft delicate ring of muscles. The tips softly caressing them as he talks to her. That he was doing this, in all places a changing room in an adult store, didn’t bother him, but added to the thrill. There was a dirty raunchy nature to the whole thing that made it so exquisitely pleasing. The tips of his fingers slowly circling her asshole, rubbing and caressing it, making sure she was ready, before he tried to work one in.
 
RE: A Lesson in Babysitting

As Jake turned her round, she caught sight of herself in the full length mirror. She was a little surprised. For just a moment there she looked so very different. The new red heels with the dress and the shiny black collar around her neck. She looked like exactly what Jak had wanted her to look like of course - a slut, and with the slightly messed up hair and the flushed red cheeks, she kne why people had been staring at her. She baulked a little. She had never seen herself look like this before and she was sure her father would have a heart attack if he could see her now.

Before she could say or do anything she felt Jake's hand on her back pushing her forward. She bent forward, then partially changed her mind and looked tom stand up again, but Jake just eased her into the position he wanted. She moaned softly at the feel of his hands on her legs and ass. And then finally her brain recognised the question.

"What?...erm... No...no-one...never. Jake...maybe we should ahhhmmmmm" she was going to suggest that perhaps they should go home before they did anything else, but then she felt something that she had never felt before and it made her moan loudly again. Whatever h was doing felt really good. She heard the question again and finally her brain put it together.

No..no-one's ever...Jake. I'm not sure...I mean ... It's gonna hurt... Mmmmmm oohhh god...."
 
RE: A Lesson in Babysitting

Now as Jenna admits that she’d never been truly touched in this forbidden way, Jake just smiles enjoying her confession. In so many ways she was innocent or at least inexperienced, and yet there was already something about her that spoke to the person he felt and hoped she would become. Slowly Jake applied pressure with the tip of his finger against her puckered portal, his finger worming its way into her backside. The other hand gently applied pressure to her back, to keep her bent over, as his finger slowly penetrated her virgin ass.

Good then, we’ll get you ready for your first time.

Jake turned and twisted his single long digit as it continued to push its way into her ass, the lubricant helping it slip past the tight ring of muscles that resisted the intrusion. The moan that slipped from her lips delighted him, as he gently began to stroke his finger in and out of her ass, short slow strokes that would gradually grow in length and intensity. The hand on her back, moving up and grabbing her head by the hair and giving it a tug as he took further control of his conquest.

You like that don’t you? You like the way my finger feels in your dirty ass?
 
RE: A Lesson in Babysitting

Jenna reached out her hands, placing then on the floor in front of her to give her some balance. Her eyes closed and she moaned as she felt his finger pushing inside her. In her head she knew she should be stopping this...she certainly shouldn't be enjoying it. This wasn't something that was supposed to be pleasurable... And they shouldn't be doing this here. The otherside of the door was lord knows how many people...and what if they could hear. But as illicit as it was in every sense, it felt good; so much better than she could ever have imagined.

The suggestion that she be readied for 'her first time'... Her first time being fucked in the ass panicked her a little more. Here?! Now?! But before she could formulate any words of objection, she felt his finger twisting and pushing a litle deeper with each stroke. All she could do was moan. And whilst she felt his hand moving reassuringly - or so she thought - up her back she was surprised as her head was suddenly pulled back. There was only one answer to his question though. In a short half gasped, half whispered expression, she gave only a one word response.

"........... Yes......mmmmmmmm"
 
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