The Babysitter's Seduction

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Tamara is trapped and must complete tasks to escape.
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With William asleep at last, Tamara relaxed on the sofa to watch her series on Netflix. The Thompsons would not be back for hours yet, and Tamara was currently without boyfriend to chat with. Her best friend Georgia was out on a date and was clearly too wrapped up in that to respond to Tamara's demands for a status update. "Have you done it yet, slut?" she sent. Georgia had been hoping to lose her virginity at last, but if she had achieved that, she wasn't deigning to tell Tamara.

Tamara herself was no virgin, although she wasn't all that experienced either. She was only eighteen, after all, and her parents were super strict about boys. Between that and school studies, it hadn't been until this final summer holiday before college that she'd finally been able to really spend time with Zack. Finally their on-and-off relationship had progressed beyond kisses and furtive groping.

Not that they had had anywhere to do it, except in Zack's dad's car. She liked to stroke his hard cock while he was driving, and he liked it when they parked in the woods and she would suck his cock, but she was unhappy about the idea of him coming in her mouth, and he was unhappy that she insisted on a condom the few times they went further - an awkward and uncomfortable experience within the car, made both exciting and ultimately too distracting by being basically out in public.

But overall it had been good with Zack, right up until the point she discovered he'd been seeing Georgia's older sister Carol - who had no reservations, apparently, when it came to swallowing cum. Both Tamara and Georgia agreed that this was a very slutty thing to do, but Carol was the sort of girl who could keep two boyfriends on the go. She had huge tits and used them the way God intended. Tamara envied her more than hated her, but Zack could fuck off for being a cheating bastard.

Unfortunately, that meant her night spent babysitting for the Thompsons was boring in the extreme. Tamara was too awake to sleep, and too horny to relax and chill. She fingered herself idly while she watched TV, and out of curiosity sucked on her fingers to taste herself. Zack had never wanted to go down on her, and anyway it would have been physically awkward in the car, but apparently Carol had persuaded him to do it to her, presumably in exchange for swallowing his cum.

Perhaps they had even done sixty-nine. Everyone sniggered about the number sixty-nine, and Tamara had seen the position talked about often enough in magazine sex columns, but she struggled to imagine what it would actually be like. Plus, was it really possible to come while worrying about the other person finishing in her mouth? While worrying about the fact that the other person was effectively staring at her ass?

Tamara's friend Lucy - well, sort-of her friend - was one of those girls who prided herself on still being a virgin. Her parents were very devout, but at the end-of-school party Tamara had walked in on Lucy mid-fuck. Tamara had been searching for a free bathroom to use, and had been treated - if that was the word - to the sight of Steve's bare cock being denied entry into Lucy's virgin pussy. "My ass, Steve," Lucy insisted, before noticing Tamara watching from the doorway and blushing bright red. "Either join in or fuck off," she hissed, and Steve wasn't waiting to find out which. His fingers, thickly coated with lubricant, lined up with Lucy's rear entry and pushed slowly in.

Zack had never wanted anal, to Tamara's relief. Probably he would have, eventually. Magazine sex columns were full of advice about anal, and Tamara had watched enough porn clips to know porn sex always progressed from mouth to pussy to ass and back to mouth again. In porn, also, no one had any hair down there. Tamara was willing to bet that Carol had no hair down there. Had she offered her ass to Zack too, before swallowing his cum?

Bored of her series, Tamara checked on William - he was sound asleep - and on impulse opened the door to the Thompsons' bedroom. It was a large, en suite room, beautifully decorated with a large double bed. Placed on top of the silky blue duvet was a wooden box, a card on top reading, "Happy Birthday," in gold calligraphy.

It was Mrs Thompson's birthday. That was why they had gone out, leaving Tamara to babysit William. Tamara studied the box. There was no lock that she could see, nothing to prevent her from peeking inside to see what gift had been prepared. Peeking into someone else's present was wrong, of course, and Tamara resisted for almost a whole minute before lifting the lid just a crack...

... and then all the way, because it was just the simple lid of a simple wooden box, and what she glimpsed inside was too intriguing not to get a proper look at: a collar. A thick, purple, leather collar, clearly designed to be worn by a woman. Tamara lifted it carefully from the box, studying it from all angles. Clearly the Thompsons were into some kinky stuff.

Kinky, but certainly expensive too. And real leather. It felt very solid in her hands, and strangely seductive too. Tamara wondered what it would look like about her own neck - and, indeed, whether it would even fit. She would not be able to move her head much, even if it did. The collar locked automatically at the back, but there was a key in the box, so there was nothing to stop her trying it on - except that it wasn't her gift, and the sensible thing to do was to return it to the box.

Tamara was a sensible girl - usually, anyway. Boredom, curiosity and opportunity combined to produce a terrible temptation, however. She stood in front of the floor-length mirror as she wrapped the collar about her neck - and it did fit, so snugly however that she had to hold her head upright, neck fully extended, before the collar clicked shut.

Tamara loved the look of it, and was surprised by how much she enjoyed its firm grip on her. For something that was basically a dirty bedroom secret, it had an elegance and eroticism to it that made her look particularly sexy. The purple suited her brown eyes and dark curls too.

In the corner of the room, a laptop computer stirred to life, and the sudden sound of a lock turning came from the bedroom door. "What the fuck?" she said, and hurried across the room to test the door - it was definitely locked. She was about to bang on it and call for help, when she remembered she was alone save for William, and she'd left her phone downstairs too, so there was no calling anyone else for help, not without breaking out of the room first - while wearing a gift that hadn't been intended for her.

"Fuck," she said, and retrieved the key from the box.

Except the key in the box would not fit in the collar, or in the door, and her increasing state of panic did not help in the effort. She searched through the drawers and looked in the wardrobe, but saw only clothes. No keys. "To unlock the collar," a synthetic voice spoke from the laptop, "you must first complete the following tasks. One: Remove all clothing."

Tamara stared at the computer in shock. Slowly it dawned on her that in daring to put on the collar she had unwittingly become a part of whatever sex game went along with it. And further, while it might be possible for her to escape the room somehow, there was no way to escape the Thompsons discovering that she had worn the collar - which would be extremely embarrassing.

No way, that is, except following the instructions. If she could get the collar off and back in the box, there was still a chance the Thompsons wouldn't suspect a thing. She could be back downstairs and happily watching her series when they eventually got home, and William still fast asleep, undisturbed by her predicament.

She stared at the green light on the laptop that told her the camera was active. Was someone watching her, or was it just a program? She tried pressing keys and moving the mouse, but the screen stayed blank except for that same instruction in bold white letters: "One: Remove all clothing."

Tamara peered out of the window and imagined herself climbing down - or dropping down, more likely, into the dark of the large back garden... but none of that solved the problem of the collar. There was likely no way to get it off without damaging it, and that meant either waiting for the Thompsons to come home and find her, or following the computer's deviant instructions in the desperate hope that no one was watching her - or, worse, recording her.

And that 'One'... If removing her clothes was only the first step towards freedom, what would be next? Tamara's panic receded, giving way to a shameful excitement. As utterly foolish as it no doubt would be to yield to the computer's demands, she was certainly no longer bored. The mistake was already made, the moment she took the collar from the box and fitted it about her neck.

"Fine," she said, glaring at the camera for effect. "You win. But you better not be recording this."

In a way, it was easier to imagine that there was someone watching her, although the idea of that being really the case was far worse. It was easier to imagine a lover watching, because there was nothing sexy or exciting about removing her clothes for an unfeeling computer program. Tamara was not shy about revealing herself to a lover. Zack used to murmur, "Sweet caramel curves," as he kissed her breasts - not as big as Carol's, of course, but a good size and shape.

Tamara kept her eyes on the camera as she tugged her blouse and vest off. The collar about her neck was a constant presence, a comfortable but firm grip on her neck that prevented natural movement. She removed her socks and leggings next, and admired her figure in the long mirror. Regular exercise kept her muscles toned and her belly flat, and between the collar and her black lace underwear she really did look good enough to eat. "Well?" she said to the camera, pirouetting like a glamour model.

There was no response, just that continued instruction. "Fine," she muttered, and unclasped and removed her bra, baring her breasts to the camera and jiggling them for effect. She hesitated before removing her knickers, however. If this was being recorded, there was little shame in being topless, but if her pussy ended up all over the internet...

Tamara shuddered - and then laughed as she imagined her mother being far more upset that she'd opened someone else's gift. "Well, young lady, if you're going to act like a slut, then you'll get what you deserve, but Tamara... Why would you open Mrs Thompson's gift? Didn't we raise you better than that?"

Taking a deep breath, she peeled that last, delicate undergarment down her legs, and stepped out. "Satisfied?" she demanded, aware from a glance at the mirror that her cheeks were bright red as she stood collared but otherwise naked in front of the camera.

"Two," the synthetic voice spoke out. "Dress for school." The words on the computer screen changed to match the instruction, but beneath the words was an illustration of a bed with a box underneath.

"Dress for school," Tamara muttered indignantly. "I thought I'd left school." She got down on her knees and peered beneath the bed - and, indeed, there was a large cardboard box squeezed beneath it. She tugged it out and lifted the lid off to see knee-high black leather boots, a tartan skirt, a white, button-up shirt, and lipstick. Tamara snorted with amusement. "I would have been kicked out of school for wearing this," she said.

It wasn't a school uniform. It was pure stripper-wear. Glad as Tamara was to put something on at least, the white shirt didn't even reach her belly and the skirt was so short it barely covered her bum - and that was with her standing up. The boots were wearable, laced up at the front, and had thick platforms and high heels; she was grateful that the heels were chunky, since walking in them was already hard enough without having to balance on the sharp points of stilettos.

As ridiculous as the whole idea of it was, it did fit her well. Tamara stood in front of the mirror to apply the lipstick - bright red - and couldn't help admiring how sexy she looked. Slutty, of course, but very sexy. It was a shame Zack wasn't there to see her.

"Happy?" she asked her unseen lover, wondering if this was maybe it. She teased a finger beneath her skirt, pressing it between her labia to determine just how wet she was - and she certainly was. Tamara was enjoying this teasing sex game so far.

"Three. Insert plug." This time the computer's illustration of the bed had an arrow pointing to under the pillows. Tamara was uncertain what was meant exactly, but obediently checked under the pillows on the bed and found a tube of anal lube and a black silicone toy with a jewelled base.

The toy was shaped like an egg with a thick stem, and seeing it triggered a memory from those porn clips she'd watched with Georgia. A blonde actress had been walking around a shopping mall with a vibrator in her pants and another toy, a lot like this one, in her ass. Tamara stared at the toy - the plug - and the tube of anal lubricant, and read again the words on the computer screen. "You want me to put this in my ass?" she asked with an unhappy frown.

There was no answer. She hadn't expected one, but playing dress up was a lot different from sticking scary toys in her virgin ass. The situation was surreal. She was supposed to be babysitting, and instead she was trapped in a bedroom wearing a thick collar and dressed like a sexy schoolgirl stripper - and a computer was telling her to insert a sex toy. While possibly recording her. She wasn't even sure it was possible to insert it, although clearly Mr Thompson thought it was something his wife would do.

Tamara stared at the plug in her hand. It was such a little thing in itself, but considering where it needed to go, it was huge. And also, it was one thing to wear another woman's collar, but to use someone else's sex toy... It was clean, but was it new? Maybe it was regularly in Mrs Thompson's ass.

She sighed with frustration. When she'd left her house that evening, she could never have imagined she'd end up having to stick a plug in her ass. "Fine," she muttered. "I'll try." Although how, she wasn't sure. Tamara had never stuck anything in her ass before, and was pretty sure it would hurt. She snatched up the lube and marched angrily into the bathroom. She would try, but the computer and whoever didn't need to watch her sticking her lubed up fingers into her ass in preparation. The plug was humiliating enough without that.

With one boot propped up on the side of the bath, she contorted herself until her fingers could apply gel to the target location. It was a position that really exposed her pussy - not that anyone was looking, but between that and touching herself in the dirtiest of ways, she felt more like a stripper than ever. Worse, like a streetwalker. Like a prostitute preparing her ass for a client's thick cock.

The sensation of her fingertips poking in through that tight ring of muscle was interesting. Intense and a little confusing, but not actually painful. When she smothered the plug in more lube and tried to push it in, that intense, stretching sensation built, and built, until she was gasping with effort - and suddenly it slipped through her fingers and fell into the bath with a thud. "Fuck," she hissed, panting. How much had gone in? Probably not much. Certainly nowhere near enough.

She tried again, pressing the plug a little way in, then as much as she could stand to, before letting it slip a little way out. By pressing, then relaxing, she was able to fuck herself with the tip of the plug, and hoped thereby to gradually deepen the thrusts until it was fully within - but that stretching was too intense. Weirdly good, but still too intense. Always there was a point where the intensity turned to pain and she worried that she would damage herself in the attempt.

Her pussy was so wet though, and her clit demanded the touch of her fingers, so that for a minute or two Tamara was both rubbing her clit and fucking her ass - and if it hadn't been killing her legs to hold this position she might have succeeded in doing more.

She almost admitted defeat, but the thought of having come so far - that damn computer had got her fingering her ass like a dirty slut, or like a Carol! - and not actually completing the challenge... well, that would just be humiliation without the reward.

Tamara straddled the edge of the bath and slowly lowered her bum onto the plug that she held still there with some difficulty. She let gravity do the work, pulling her down onto that brutal invader that stretched her wider and wider. "Fuck," she said, breathing heavily, struggling to think beyond that unnatural penetration. It became a mantra: "Fuck. Fuck. Fuck."

And just when she could take no more, it slotted abruptly into place within. Worried that it might disappear inside her completely, she studied it with her fingertips, until she was reassured that it was secure - and, importantly, that she could remove it again as soon as this kinky and very unexpected sex game was done.

Finally catching her breath again, Tamara wiped away the excess lube from her crack and washed her hands, then walked back out into the bedroom, really quite enjoying the sensation of that plug within her, and oddly proud of her achievement. She even laughed as she turned and bent over, spreading her cheeks so that the camera could have an unhindered view of the gem. She wished she could see it properly herself, but the collar made it difficult.

And of her pussy too, the black curls glistening with moisture to prove that Tamara could be just as much a slut as any Carol.

"Four," the voice said. "Come." The screen echoed the command, this time the illustration of the bed having a woman lying on it and fingering herself.

"Right," Tamara said with a wry grin.

With a sigh of frustration, she surveyed the bed. Once this next step was done, assuming it was the last - and there was no guarantee of that! - she would have to tidy the bed, clean herself and the plug in the bathroom (making sure to leave the bathroom as spotless as she found it), pack the schoolgirl costume away in its box under the bed, and return the collar and plug too. All of which would take time, and at some point the Thompsons would be home again.

Added to which, Tamara usually saved her masturbation sessions for when she was in the shower, because she could get very wet. That one time with Zack in his dad's car when she'd actually come, she'd gushed so much that the seat's fabric had been left visibly damp afterwards.

She pulled the duvet away and laid a large towel from the bathroom onto the bed, aware constantly of that plug filling and stretching her ass. Aware too, each time she passed the mirror, of how slutty she looked - and how slutty she felt too. Even knowing the computer might be recording her, she'd showed it her wet pussy and her plugged ass, and she was about to make herself come in full view of the camera. Only a slut would do all that.

After all that agonising she had done over the third task, Tamara barely stopped to question the fourth. Indeed, she had started it already, fingering herself in the bathroom while teasing her ass. All prepared, she positioned herself on the bed, her bum on the towel, her chunky heels digging into the sheet either side of it. There was, of course, no need to undress. Her skirt covered nothing, and her shirt was thin enough for her to tease her nipples through the cotton with one hand while the other delved between her thighs in search of her clit.

The way her ass kept clenching about the plug was a delightful sensation that added to the sweet pleasure of her fingertips against her clit, against her nipples. In the quiet of the bedroom, there was only the sound of her breathing, the occasional involuntary moan that she tried to suppress for fear of waking William, and the squelching of her fingers gliding through her wet pussy.