Tom

Your heart skips a beat as you read Tom's name on the piece of paper, remembering that he's still in the closet with Nicole. However, you internally rejoice as you realize you can kill two birds with one stone with this new dare.

Walking over to the closed closet door, you quietly place your ear against it, trying to hear what's going on inside. You hear some whispering and shuffling, but can't make out any more detail than that. At least it's not moaning or sounds of sex. Stepping back a bit, you knock, and then loudly announce, "Tom, I got you. I dare you to come out of the closet with Nicole, and, in addition, take Sarah's anal virginity!"

You immediately hear Sarah gasp in shock and indignation, and she glares furiously at you. A few months ago, at a boozed up party similar to this, a very drunk Sarah had confided in you that although she had a not untrue reputation for being a slut and sleeping with a lot of guys, she'd never done anal before, partly because she was afraid it would hurt, and partly because she enjoyed the sense of power it gave her to dangle it as a false hope in front of guys. She probably assumed you'd been as drunk and had forgotten, but it was too juicy a fact for you to ever forget, and you knew now was a perfect time to use it to get back at her. Judging by the looks on Matt and Miranda's face, they hadn't known either.

You're distracted as the closet door creaks open. You breathe a sigh of relief as you see that her panties are still on, but can't help but be infuriated when you see that Tom predictably is roughly fondling and squeezing her ample breasts, while his crotch is pressed up against her. As soon as the door is open, Nicole pushes his hands off of her, and stumbles out, before collapsing on the floor, panting. You're confused, as both her and Tom's clothes are still on, but it's obvious from how flushed and flustered she is that something had happened in the closet.

Tom, meanwhile, saunters out, having forgotten Nicole for now as he gazes hungrily at Sarah. "You're kidding, right John? Sarah, the most infamous slut in our grade, an anal virgin? That's impossible. Well, doesn't matter either way to me, I'm going to enjoy taking that plump ass! But first things first." Reaching back into the closet, Tom grabs a towel, and tosses it at Sarah. "Clean up that mess on your face and chest, you look filthy!"

Sarah pouts and sticks out her tongue at Tom from where' she's sitting, but does as he suggested, using the towel to wipe Matt's cum off of herself. She starts with her stomach and breasts, meticulously cleaning every bit off, then began to wipe her face off with it, covering her eyes. When she finished and removed the towel, she gasped in surprise as she saw that Tom, who had taken the opportunity when her face was covered to move up to her, now had his already hard cock out and waving in front of her face. Her gasp of surprise became one of disbelief and shock, as she saw just how massive and how thick Tom's cock was. "Oh my god, that thing will never fit in me!" She exclaimed.

"Sure it will, although I bet it's much more impressive than Matt's tool! We'll just have to make sure it's properly lubricated first!" Tom said, and proceeded to press the tip of his cock against Sarah's lips. Sarah instinctively opened her mouth, and almost gagged as Tom immediately and roughly started shoving his cock into her mouth. Sarah was no stranger to giving blowjobs, but she doubted any of the other guys had been nearly as well endowed, and her jaw ached as it stretched to fit Tom's girth. He wasn't going easy on her either, grabbing her hair and the back of her head to pull her face towards his crotch while he steadily pushed forwards.

After only having taken 5 out of Tom's impressive 8 inches, Sarah could feel his cock head hitting the back of her mouth, preventing it from going deeper. She expected him to then pull back, but instead he just pushed harder, and Sarah gagged as his cock incredibly began to slide deeper in, pushing into her throat now. At first half an inch, then an inch, then two, and inevitably all 3 extra inches slid past her lips, and the tip of his dick and shaft were firmly lodged in her throat, preventing her from drawing breath. Sarah started struggling, trying to use her hands to push him off, but he easily grabbed her wrists in one hand and pinned them down, while using the other to hold her head tightly against his crotch.

You stare in guilty fascination at the scene unfolding. The sight of Sarah, naked and on her knees, being dominated by Tom, can't help but turn you on. Her generously proportioned tits are quivering and bouncing as her whole body convulses with her attempts to push him off. You can actually see the bulge in her throat from Tom's cock invading her, and stare intently as Tom finally starts pumping in and out, following the outline of his shaft and cock tip against her throat as he does so. Sarah desperately draws a quick breath each time Tom slides his cock outwards, only to gag again when he plunges it back all the way in. He's soon set a furious pace, and the room fills with the wet, slurping, gargling sounds of Sarah's rough face-fucking, and the slapping sounds of Tom's balls hitting her chin with every thrust. A copious amount of spit and drool is leaking from Sarah's lips, coating Tom's cock and dripping down her chin onto the floor and her legs.

You sneak a glance at the others in the room, and aren't surprised that Matt is staring just as intently as you were, looking both incredibly horny and distraught at the sight of his crush being used like a fuck doll by the class asshole, and knowing he'd soon be taking her anal virginity. You are surprised and a bit worried to see that Miranda seems just as fascinated. Was she comparing Sarah's oral skills to the earlier blowjob she had given Tom? Was she wishing it was her instead? You then look over at Nicole, and notice that she's sitting on a chair and grinding her panties against it, lips parted. What was going on with her? The behavior wasn't like her, and once again you can't help but wonder what happened in the closet between her and Tom.

Without warning, Tom lets go of Sarah's head and arms and leans back, pulling his cock free of her mouth and splattering her face with her spit. He grabs her shoulders and roughly pulls her to her feet, then spins her around and shoves her, causing her to stumble and fall against the couch, her face and tits against the cushions and her ass pointing up invitingly. He follows her over to the couch and quickly positions his cock between her ass cheeks before she can get up. Tom reaches down and grabs one of Sarah's ass cheeks in each hand, and pulls them apart, revealing her pink, puckered asshole and causing it to part invitingly ever so sightly. He slides his cock against it a few times, making sure to transfer plenty of Sarah's drool from his dick onto her asshole.

Sarah meanwhile seems to have given up resisting, and has a look of nervous anticipation on her face, biting her lips hard and grabbing onto the couch with her hands. "Be gentle Tom, I'm begging you. I've never had anything up there before." she pleaded.

"Don't worry, every slut I've fucked up the ass has learned to love it and have come back to me begging for me, and you won't be any different!" Tom bragged. Feeling that she was lubricated enough now from her own spit, Tom grabbed his cock shaft with one hand, lined up the bulbous tip against her asshole, and started pushing. Sarah moaned loud and long as for the first time in her life she felt something sliding into her butt. She desperately tried to relax, but it didn't help that Tom was extra well endowed, and it was proving to be a real challenge for her first time. Finally, impossibly, the tip of Tom's cock slipped past her sphincter, and Sarah breathed a sigh of relief. Mercifully, Tom stopped to let her adjust before pushing in further.

"Damn Sarah, your ass is super fucking tight! Feels like it has a vice hard grip on my cock, good thing I made you lubricate me or I'd never be able to get the rest in! I guess it really IS possible your an anal virgin, there's no other way you'd be THIS tight!" Tom teased Sarah mercilessly.

Meanwhile, you noticed that Miranda had gotten up from her seat and walked over to Tom and Sarah, trying to get a better view. She was craning her neck to see Tom's cock, mesmerized by the sight of it lodged firmly and tightly in Sarah's ass.

"Like what you see Miranda?" Tom asked, having noticed her moving closer. "Maybe you should pull up a chair! Don't worry, there's plenty of me to go around, I'll get to you. I'll be sure to give that tight ass of yours a thorough pounding too, until you can't sit straight for a week!" Tom sneered, while looking directly into her eyes. Miranda glared at him, but you notice that she didn't move back, and nor did she refuse him, causing the gnawing worry in your stomach to grow. While Sarah's body could be described as busty and curvaceous, with a bubble butt, Miranda had a more slim and toned build, with a perfect tight butt that was often accentuated by the body hugging jeans and yoga pants she often wore, and a body that made her look like a busty ballerina. You weren't sure how if Sarah was having so much trouble fitting Tom's cock in her asshole, Miranda would ever manage, and you weren't sure you wanted to find out.

Tom meanwhile had turned his attention back to Sarah. He gave her ass a sharp and solid slap with his hand, causing her to yelp and clench her sphincter around him. When she inevitably relaxed again, he took the opportunity to slide another inch of his cock into her ass, causing her to tense up again. He followed this with more spanking, sliding his cock in further each time. Sarah alternates helplessly between yelps and moans between the sharp pain from her ass being slapped to the unexpected pleasure of something so hard and solid sliding into her bowels, until finally all 8 inches of Tom's cock were buried hilt deep in her ass. Without pausing, Tom started pulling back until only the tip was once again left inside of her, before thrusting in again all the way.

Despite her earlier objections, Sarah was obviously starting to enjoy her first anal fuck, and reached one hand back between her spread legs to stroke her clit. She slid one finger between her dripping pussy lips, gasping and parting her lips as she fingered herself. Soon, a second finger joined the first, and she was sliding both knuckles deep into herself. She timed her fingers to plunge into her pussy each time Tom's cock slid out of her ass, and slide back out when his cock plunged back in, establishing an alternating rhythm.

"Oh fuck, I can actually feel your fingers in your pussy while I'm fucking your ass!" Tom exclaimed. "Oh god, you feel even tighter now, holy SHIT!" He picked up the pace, grabbing onto her hips with his hands and pulling her ass back against him with each thrust, plunging his thick cock deep in and out of her ass. Sarah's moans and groans quickly grew in pitch and volume, as she worked herself closer and closer to the edge. Before long, she screamed in pleasure, her whole body convulsing as a huge orgasm ripped its way through her, her ass bucking against Tom. The feeling of her sphincter tightening and pulsing around his cock as she came was too much for him to bear, and with a loud groan of his own, Tom thrust his cock all the way into Sarah's ass for the final time, and unleashed a huge torrent of cum deep into her bowels. They both seemed to cum for what seemed like an eternity, until, spent, Sarah collapsed forwards against the couch, pulling her asshole free of Tom's cock with a wet obscene sounding slurp. Tom plopped down on the couch next to her, and once again grabbed her butt cheeks and pulled them apart, giving everyone in the room a clear view of his handiwork. Sarah's originally virgin and puckered asshole was now noticeably more flushed, and was still pulsing from her orgasm and from being so thoroughly violated. As everyone watched, a thick, white stream of Tom's semen started leaking out of her asshole with each pulse, sliding down her taint and then between her pussy lips, mixing with her own juices.

"Oh my god Tom, holy shit you were right, that was fucking amazing. I can't believe what I was missing out on before. God you're a stud." Sarah gasped out, as she slowly pulled herself up, using the towel to clean herself up a bit and holding it against her still leaking ass.

"It can't have been all that, after all he came in like 30 seconds!" You countered, having noticed the interest both Nicole and Miranda were showing in Tom after his performance, and desperately trying to bring him down a bit.

"Shut up John, like you could have done any better? I bet no girl's ever let you fuck them in the ass before, pervert!" Sarah snapped at you. Tom didn't say anything, instead just looking at you triumphantly, knowing he had won. "Well then, that was fun, but it's time for me to pick a dare. Let's see who gets a piece of me now!" Tom says, getting up and walking over to the bowl.