Heads or Tails
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Heads You Win, Tails I Lose free porn video
Tom recognized Joan from his game theory class. True to her nerdy looks, she had her book and computer open, sitting alone in the corner of the café.
“Studying for the midterm?” he half-asked, taking his coffee toward a table near her. “I wish I understood that Prisoner’s Dilemma better. It’s not a situation I’d ever be in, so it just isn’t intuitive."
She looked up, surprised that anyone had noticed her.
“It’s a basic example,” she explained. “It doesn’t have to be prisoners. Any two people making separate decisions with various rewards and penalties can fit into it.”
He decided to push his luck.
“Like whether or not you should invite me to join you, and whether or not I should just pull up a chair and sit at your table.”
He flashed her a smile.
“Sort of, but not exactly,” she said, her awkwardness at being approached was reduced by her confidence expounding on the subject.
She moved her book and he dragged a chair and they continued the discussion. Before long, he had slipped in sexual references and she was getting into the spirit.
“What if the choice is oral or anal?” he flirted.
“It could depend on whose mouth and whose ass,” she giggled.
He had expected it to be harder to move the topic to sex and thought that she might demur, but her grin encouraged him to follow through.
“Would you like me to walk you back to your room?” he asked when their cups were empty and they had run out of quips.
Her eyes grew wide at the offer.
“Okey-dokey,” she said, assessing him skeptically.
Outside her door, he asked if he could kiss her. She replied by pulling him down and mashing her lips to his, parting them to use her tongue. Happily surprised, he reciprocated.
“Wanna come inside?” she whispered when they broke for a breath.
After the hour of ribald repartee at the café, few words were necessary as they disrobed amid their kisses and caresses. The only negotiation was when they reached their destination.
“I like it from behind,” she said, crawling naked onto her bed.
Standing, he grabbed her generous hips and pressed his cock against her opening. Clearly horny, she rocked back and absorbed him.
“No hair pulling,” she warned. “But if you want to put a finger in my ass, I wouldn’t mind it.”
They moved in counterpoint, gradually going faster. Her liquid spheres rippled as he bounced against them.
“Oh, woh, woh, woh, woh,” she tolled in time with each impact.
Lowering her face to the mattress, she leaned on one shoulder, the other arm reaching underneath her. In that position, she became a more stable target for him.
“Fuck me,” she gasped.
Her hand grazed his shaft and balls as she worked her pussy. Seeing her pucker between her cheeks, he dared only to tease it with his thumb as he steadied himself gripping one globe. She grew silent but he could feel the tension in her thighs. The only sound was the slapping of his belly against her butt.
Suddenly she started quivering from the waist down. His assumption that she was climaxing triggered his eruption and he groaned his elation as he pumped into her. Requited, with a noisy sigh, she flopped on her side, disimpaling herself.
Looking down to remove the condom, Tom noticed blood on it.
“Um, Joan?” he didn’t really know how to ask. “Were you still a…?”
Following his eyes to his wrapped penis, she saw the reason for the question.
“Oops! That orgasm must have started my period. I was about due.” She spoke without embarrassment. “I’ve been randy for a week but didn’t get to hook up until tonight. Glad we finished before the flood gates opened!”
In the bathroom, he snapped a pic of the cum-filled slightly bloody rubber before he disposed of it.
“That’s one,” he thought.
Like many stupid ideas, the contest arose when he and Jerry were drunk. Bragging about their conquests led to a challenge of who could have the most sex in a week. The loser would pay a thousand dollars to the winner. Any sex act counted as long as someone had an orgasm. They agreed to limit it to one a day and each had to be different.
“What about a threesome? That should count for two.” The alcohol made Jerry optimistic.
Knowing neither of them had managed that before, Tom agreed, “But they both have to participate. Just having someone watch doesn’t count.”
Jerry also scored that Monday. Both knew a few women who would have sex with them on occasion, from quick handjobs or oral in the car to overnight lovemaking.
Tom worried that Jerry had a longer list, so he focused on new possibilities. If he didn’t find someone earlier in the day, he would try a late-night booty call with a prior partner.
Tuesday, he struck out in the afternoon and was considering who to call later. He had dinner with Mila, his teammate for the computer programming assignment. Distracted by the contest, he hadn’t completed his part of it. He didn’t think of her as a prospect. Serious and intimidating, none of the guys had gotten anywhere with her.
“Why don’t I take over this module and you can focus on that one,” she frowned, disappointed with his progress.
She was determined to get an “A” even if she had to do the whole thing herself.
“I feel bad making you do more work,” Tom apologized.
For some reason, her disdainful look provoked an idea.
“Why don’t I make it up to you?” Unsure who or what compelled him, he blurted, “Let me give you a tonguejob.”
She recoiled at the suggestion, “I don’t have time for sex!”
“Hear me out,” he petitioned. “You don’t have to do anything to me. I know I don’t deserve the chance, but I want to prove my contrition.”
Trying to look more penitent than eager, he nonetheless managed to lick his lips artfully. Whether her intense stare was anger or something else, she held it long enough that she must have been considering the offer.
“Alright, but I’m going to sit on your face,” she said with determination. “And if you don’t make me cum in five minutes, you’re off the team.”
Tom’s shocked expression hid his elation. He wasn’t positive he could do it that fast but was willing to try.
In her dorm room, he got on his back on her bed while she stripped off only jeans and panties. When she knelt over him, all he saw was a thick patch of fur descending onto his face. It was fluffy and dry, but as he extended his tongue, the distinctive scent and taste made his mouth water. She left him enough room to maneuver and dampen her curls and underlying flesh.
Within a couple of minutes, she began to produce her own broth and started pressing against him. As he explored her folds, she moved to align his mouth with her most sensitive spots. Wedged in position, he licked and nibbled and sucked whatever he could.
Her moans grew louder as she humped his face, putting his nose to use as well. Although he hadn’t thought of it before, it made sense that Mila, bright and forceful academically, would know what she wanted from sex.
With no sense of time, he slurped her cooch blindly but enthusiastically. He could only hope that if it took longer than five minutes, he did well enough to make her forget the time limit.
Grinding against him as she sought her fruition, she ordered, “Suck my clit. Suck it!”
He suckled her dangling lips, latching onto them while his tongue danced between them. Her moan crescendoed with a slow tremolo then ended with a sharp, deep breath that she held. Whether intentional or inadvertent, her suddenly slack thighs caused her pussy to smother him. Long silent seconds passed motionlessly. Her noisy exhalation was accompanied by a lower release just as he had a chance to gasp for air. He wasn’t sure whether it was a queef or a fart—neither sound nor smell was definitive and it could have been both.
Rolling off him and sitting next to his head, Mila glanced at the tent in his pants and glowered, “I accept your apology, but you get nothing until you start pulling your weight on this assignment.”
Tom struggled to look chastised while celebrating his point for the day—as well as imagining getting something in the future. He was definitely going to put more effort into their project next week.
He didn’t dare take a picture, but the sound he recorded on the phone in his pocket would be enough proof.
It seemed that every coed on campus had a midterm on Thursday because neither he nor Jerry could get any interest on Wednesday. With four days left, Tom thought about the four women he considered likely.
“Rosé Rosie” would be the easiest. She was known for her love of wine and the loving she did under its influence. Jerry knew her, too, so Tom made sure to talk to her right after the midterm. He guessed she would be in the mood to release some tension that evening.
They shared the bottle he brought as they watched a steamy French film. Before long, she had his pants undone and he had her blouse unbuttoned and her bra moved aside. When she stood to shove her pants to her ankles, he did the same.
The mutual masturbation escalated when the on-screen love scene made it unnecessary to read subtitles. Tom sucked her nipples as he strummed her clit. Rosie closed her eyes and leaned back, surrendering to his dexterity.
Her stiffening body lifted her ass off the couch as she whimpered. He slipped two fingers inside her as he buffed her muff.
“Oh, oui! Baisez-moi! Je jouis!” she squealed. The way she bucked, Tom didn’t need subtitles to understand her.
When she collapsed back onto the couch, she closed her legs, trapping his hand against her hot wet sex. He thought about trying to get a picture since her eyes were still closed, but he couldn’t get to his phone without disturbing her euphoria.
Something exciting happened in the film because the sound grew louder, breaking her reverie. She released his hand and, noticing him sucking his fingers, regrabbed his projecting pole. Slinking off the couch, she knelt to swallow it.
Rosie liked sucking dicks and was good at it, able to make guys last as long or finish as fast as she wanted. Today it was the latter. With her head in his lap, Tom was able to slip his phone from his pocket and snap a selfie without her seeing or pausing.
He had no choice when she took him deep and sucked hard—he spurted into her throat. Maybe it was the wine, maybe it was her position, but she gagged a bit then lifted her head as she coughed. Without warning, she heaved a spray of disgusting gastric fluids onto his lap.
Jumping to her feet, she put her hand over her mouth and ran to the bathroom to complete her disgorgement. With no good choices, he removed and used his soiled shirt to mop up what he could.
“C’est la vie,” she giggled when he went to check on and console her. “Je t’en dois une belle.”
“No worries, that one still counts!” he chuckled at his double entendre; of course she didn’t know about the contest.
Bare-chested, he jogged back to his room carrying his defiled shirt.
Friday was more involved. Sarah expected dinner in a restaurant and a movie in a theater before she would put out, but that plan had worked many times before.
Unfortunately, when they got to her door, she gave him a peck on the cheek and snapped, “Goodnight!”
Before he could try to protest, she interrupted. “Oh, I heard about the contest you and Jerry are having, and I’m not going to play,” she sneered. “In fact, none of us are!”
Tom was aghast.
“That’s right. After Jerry had sex with Becky tonight he bragged about it. She threw him out and sent us all a text. Fortunately, I saw it while you were driving. You’ll both find it hard to score another point!”
She turned and slammed the door in his face.
“That bastard,” thought Tom. “I bet he did it deliberately. Jerry got today’s point so he was ahead. If neither of us can score this weekend, he wins.”
Tom sent him some profanity-loaded texts and voicemails while trying to figure out how he could score in the next two days.
Julia and Tom had dated in high school and ended up at the same university. They remained friends with benefits as they explored opportunities with other partners. She was his ultimate fallback and he was hers.
He brought her favorite sushi to her room at the sorority house Saturday afternoon. She had heard of the contest, so knew what he probably wanted. Confessing his predicament, he begged for her help.
“Despite the ridiculousness of your contest, it seems Jerry did cheat by revealing it when he did. I might be willing to help you even the score,” she said.
So long as she didn’t absolutely refuse, Tom knew a way to convince her.
“I’ll do your feet,” he beamed.
Her face lit up.
Julia’s girl-next-door looks were attractive enough. With makeup and the right clothes, she was downright bodacious. But her size twelve feet were big and unsightly. Her long toes had odd shapes and angles; she would never wear sandals.
It had been a long time since he worshipped her feet, but when he had, she loved it. He sat her in a comfortable chair and filled a basin with hot water. Removing her sneakers and socks, he massaged her feet as they soaked for a bit, then washed and dried them.
Taking one foot, he kissed it all over from callused heel to wayward pinky. Usually trying not to tickle her, he occasionally impishly dragged a fingernail across her arch to make her jump. He tenderly licked around and between each toe.
“You suck them just like you do my clit,” she sighed as he took each digit between his lips.
Not by accident, when he switched to the other foot, he rested the first against his crotch. She traced the outline of his erection with her big toe. Her fidgeting encouraged it as he worked on her other foot. After giving it equal time, he took them together, playing her toes like a harmonica and snuggling his face between her soles.
Jumping up, he disappeared into the bathroom and emerged carrying a bottle of baby oil—naked from the waist down. His rigid rod left no doubt about his desires.
When he knelt in front of her, Julia stood up, saying, “Well that’s not fair!”
With a few movements, she stepped out of her shorts and panties and sat back down.
Applying oil to her feet, Tom could not avoid leering at her neatly trimmed pussy. She had scooted forward slightly to make it easier to stroke herself. Neither rushed as he massaged her slippery feet and she fingered her slippery folds. The combination soon had her moaning softly.
His dick was bobbing and dripping but he ignored it. Julia’s eyes were half-closed, her breath growing ragged, her nipples poking through her bra and shirt.
Finally, she sighed, “Okay, go ahead. Just don’t make a mess.”
Tom spread a palm of oil on his banana and kiwi fruit, then positioned himself between her arches. She squirmed a little as his mushroom cap tickled her. Taking the initiative for a few moments, she used her feet to test the ripeness of his produce. Giggling, she pinched his firm and squishy parts with her toes.
Returning control to him, her fingers became more active and focused. A deep breath suggested she was reaching the home stretch, so Tom moved her feet to the most effective position.
Spreading her knees wide brought her heels together, which allowed her long toes to form a plausible grip. His hips thrusting and his hands pumping her feet would eventually be enough. Watching and hearing her polish her hood ornament drove him to the edge.
She opened her eyes and locked on his as she reached her peak. Her fingers had been a blur but stroked slowly and deliberately as they sparked the bolts of pleasure from her electrode. The unavoidable jolting of her legs set him back a few strokes and he waited for her to calm before resuming speed. Post-orgasmic sensitivity made her feet twitch as he fucked them, but he was too close to be deterred.
“I’m gonna cum on your magnificent feet,” Tom exclaimed.
When the spasm arrived, he aimed his hose at her toes, making sure his creamy lotion was kept off the floor. He wrang a few final drops from his tube then smeared his load all over her feet, using his fingers to get it between her toes.
“I thought I said don’t make a mess,” Julia laughed as she regained her composure.
“Oh, but ziss is an important part of ze treatment,” he faked a bad accent. “All ze essential oils and proteins and moisturizers.”
Alternately tickling and soothing, the goo soon became sticky, so he hopped up to refill the basin and give another footbath. Patting them dry with the towel, he did one last round of kisses.
“Thank you so much for letting me even the score,” Tom said as they put their clothes back on. “Unfortunately, if he finds someone today and tomorrow, I would need a threesome to tie. I have to hope he doesn’t as well as find someone myself tomorrow.”
“Well…,” Julia started, getting his attention. She had decided to stay barefoot for a while. “You did do a terrific job on my weird feet and we have been friends for a long time.” She left it hanging for an eternal moment. “I might be able to arrange a threesome.”
“It can’t include you, according to the rules,” Tom reminded her.
He hoped some of her sorority sisters didn’t know Becky.
Julia looked smug when she stopped by Sunday.
“I can solve your problem but it’s going to cost you. I have two friends who will do you, but they want two-fifty each.”
“Alright,” he acquiesced. “I guess I’d rather end up with five hundred than owing a thousand.”
“Well,” she winked, “I think I deserve two-fifty for arranging it… and another two-fifty for yesterday!”
“That’s extortion!” he objected.
“Just the cost of doing business,” she grinned. “If you’d rather pay a thousand to Jerry….”
Expletives were all he could utter.
“There are other constraints, but I worked them out. You’ll see I earned my commission,” she explained. “Both of them are in relationships and don’t want their boyfriends to find out, so you’ll have to be blindfolded. They’ll do it together, so it will be a threesome. One of them secretly has the hots for you and would love to give you a blowjob.”
He nodded, wondering who that might be.
“I hope this isn’t a dealbreaker, but the other one wants to pop a guy’s anal cherry. You’re still a virgin back there, aren’t you?” She burst out laughing at his stunned expression. “I assume that counts as sex for the bet.”
He was ready to explode and not in a good way. But when Jerry insisted a threesome counted as two, he didn’t specify details.
Tom had thought about getting pegged but never pursued it, not knowing any women who might want to do it. “Maybe Mila,” he thought, remembering their encounter.
It was not what he had hoped for, but time was running out and he was desperate.
“Okay, you win,” he sighed. “But if I can’t know who they are, you better be there to be a witness.”
“Don’t worry,” she smiled. “Go clean your rectum and meet me at eight.”
Jerry had missed Saturday but had already found someone that day so Tom knew the threesome would decide the winner. Julia led him in the back door of her sorority house to a room in the basement. At one end, there was a large odd-looking chair. As they approached it, he realized what it was.
What he initially thought was the back of the chair had three holes arranged horizontally, a large one in the middle and smaller ones on either side. It was a pillory! The odd seat was for your knees when your head and arms were in the holes.
“It’s for sorority discipline but it will work for tonight. It’s the only way to be sure you don’t peek and both insist on that,” she explained.
He resigned to his fate. “Let’s get this over with.”
“You’re going to get a blowjob,” she smirked. “The rest is just the cost of doing business.” She pinched his ass to punctuate the comment.
Tom undressed and knelt in place as she lifted the top piece, lowering it when his head and hands were in position. The frame provided access to his private parts from the front as well as behind.
“Relax,” Julia said as she applied the blindfold. “I’ll be here the whole time. They won’t say anything, since they don’t want you to recognize their voices.”
After a few moments, he heard a door open and close.
“Is everybody ready?” After a pause, she added, “There is one tradition that should be observed. We always warm up the errant party. Would you like a brief demonstration, Tom?”
She dragged a wooden slat across his backside. He shuddered, hoping she meant it when she said “brief”.
“If you think it’s necessary,” he whined.
It was a lightweight instrument and probably no worse than her hand would have been. She scattered ten swats around his cheeks. They did sting and he couldn’t avoid reacting.
“Someone is being tempted by that ass,” Julia crowed when she finished.
He tensed in the silence, unsure what to expect first. The answer came quickly as fingers touched his member. “Heads”—as he dubbed her—tugged at him gently, getting familiar with his organ as it expanded. He enumerated the women he knew in relationships, wondering who lusted after him. Her head grazed his stomach as she moved under him. Her wet, warm lips were electric as they touched the tip. Wrapping her mouth around the head, she washed the glans with her tongue.
Heads had some skills. As she slowly bobbed on his shaft, taking and wetting more of it as she went, she cupped and fondled his balls. Pressing her fingers into his taint made his genitals throb. He was approaching his full length and she showed no reluctance to swallowing all of it. No porn star, Tom was still big enough that many women wouldn’t take him deep.
Heads pressed her nose against his belly as his cockhead found the back of her throat. Satisfied that she had it all, she slowly withdrew. He winced when he realized she had taken him completely out of her mouth, but squirmed as she painted the underside of his cock with her tongue, flicking back and forth rapidly as she moved from base to tip to base to tip.
Gripping him like an ice cream cone, she lapped his knob. Just as she took him back in her mouth, he felt hands on his ass. He was so focused on the blowjob from Heads that he had forgotten about “Tails”. With one hand squeezing his dick and another juggling his nuts, the additional hands on his butt were a momentary surprise.
He didn’t necessarily know Tails; she just wanted an asshole to deflower. Whether she was a novice who wanted to practice before pegging her boyfriend or a veteran who had just never been anyone’s first, he couldn’t guess.
It was strange being double-teamed, each one’s attentions distracting from the other’s but also enhancing them. As hard as it was to believe, his fuel injector slowed to idle when his tailpipe roared to life.
There were only a few tentative probes before he felt something drip into his crack. Agile fingers spread the lube and kept circling back to his bunghole. First, only a tip pushed inward, then a knuckle breached, then a whole finger slid in and out, then it began to swirl. Each time it popped out, it returned with another dollop of lube. Soon it was so slippery, he hardly noticed when a second finger joined it.
As if coordinated, while Heads kept him on simmer, Tails raised him to a boil. Tom quaked at the intensity when her fingers found his prostate. Although he had played with it on occasion, this felt different in a dozen ways. He expected the butt stuff to be something he tolerated for the sake of the contest; it was beginning to feel like a substantial bonus.
She didn’t rush and he was soon moaning in appreciation of the novel stimulation. A third finger was added without difficulty. Tom almost forgot the ultimate goal before Tails withdrew her fingers and introduced a smooth, round bulb.
After he relaxed his initial clench, he accepted the intruder. Bigger, but no less slippery than the three fingers, it moved in and out only slightly and slowly at first. Tails’s hands held his hips as she fucked him, incrementally deeper and faster.
Despite the blindfold, when that thick probe pushed against his p-spot, it was as if someone turned on bright lights. His whole body quivered as everything from the glans of his penis, which was being tongued, to the ring of his anus, which was being stretched, glowed with intense delight.
It was like an orgasm that hadn’t started and wasn’t ending. He was near the edge, but the complexity of the sensations would not allow him too close. Tom was deep in Heads’s throat while Tails was equally deep in his ass. It rewrote the cliché of fucking someone with someone else’s cock.
“Oh yeah, fuck me, suck me,” he repeated, the words coming from somewhere other than his brain.
Despite being bound in position and held by Tails, he could not keep his body from writhing with tingling excitement. At their mercy, he could only witness his body’s response.
Driven to such a high plateau, it was hard to say there was a further peak, but at some point, he realized his glands were pumping. Normally he would have warned Heads, but with her tongue against his shaft and fingers on his balls, she knew as soon as he did.
Meanwhile, Tails continued pounding, churning his insides, his grasping sphincter offering minimal resistance to the plunging piston. Overloaded with exhilaration, Tom’s animal grunts and growls drowned out any sounds the other two might have made.
He shivered with aftershocks as the ecstasy ebbed. Heads had swallowed his load and suctioned him dry before kissing the last drops from the aperture. Tails came to a stop, grinding a memento of the maximum penetration before slowly withdrawing. When his back door snapped shut, he felt an unexpected emptiness.
“Congratulations, Tom!” Julia’s voice brought him back to reality, as unreal as it was. “Thank you, you two. I’ll ensure you get your compensation. I hope you both got what you wanted out of this encounter. I’ll wait for you to exit before releasing him, so your secrecy is maintained.”
He knew it was Julia’s hand on his rear end as she gave him a few playful swats.
“I always said you had a nice butt for a guy,” she chuckled. He jerked as she circled a finger around his hypersensitive opening. “You always wanted me to try anal sex. Now that you’ve done it, maybe I’ll let you fuck my ass—after I fuck yours!”
The banter had allowed the others to depart. She removed the blindfold and released him. Drenched in oxytocin, Tom hugged and kissed Julia—and not just for helping him win. He got dressed and texted Jerry to meet them behind the sorority house.
“What are you trying to pull?” he demanded when he arrived. “You say you had a threesome and she’s the witness? After she was your score yesterday? I know you’ve been friends forever. Why should I believe you?”
“If I was going to make up a story, it wouldn’t involve me getting pegged,” Tom rejoined. “After you eliminated all my options by talking to Becky, I had to take what I could get.”
“I thought you might doubt my word,” Julia grinned slyly, “so I took a picture.” She held up her phone.
“What the fuck?” Jerry exclaimed as he tried to understand what it showed. “They put you in that contraption? Wait…!”
Tom suddenly realized what had shut Jerry up. The photo hid Heads’s face in his crotch and cropped off Tails’s head but clearly showed their bodies and what they were doing.
Both were men! What Tom thought was a strapon dildo had been a real cock in a condom.
“That doesn’t count!” laughed Jerry. “They’re guys!”
Tom choked and stared at Julia. Had she been helping him or teaching him a lesson?
“The rules didn’t say they had to be female,” she taunted.
“Yeah! You said threesome, you didn’t say what sex anyone had to be!” Tom couldn’t believe the position that he was arguing for—any more than the position that had left him with a pleasantly sore butthole.
“You two go argue somewhere else,” Julia insisted, turning back to her sorority house.
She knew Tom would honor his debt to her however the dispute was resolved.
Trisha
- 26.08.2022
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