Guess: the Ultimate Sex Game

This is a continuation of a story line by bobrobertson. The first two chapters of his story are two of my favorite chapters on this site. After noticing a long hiatus after the second chapter was posted, I wrote to him to see if there was any progress. He admitted that he has been inundated lately, and asked if I would be willing to pick up where he had left off. I was all too happy to oblige.

I strongly encourage you to read the first two chapters of bobrobertson's story, which can be found here:

http://www.literotica.com/s/guess-the-ultimate-sex-game

and here:

http://www.literotica.com/s/guess-the-ultimate-sex-game-ch-02

This chapter has been read and approved by bobrobertson. I am interested in having this become a chain story, with another author picking it up from here. If you are interested, please contact me to discuss.

As always, comments are welcome and appreciated.

Enjoy!

.....

Danielle woke up with a start from the same dream she had been having repeatedly over the last three weeks, ever since that night of playing that Guess sex game at her friend's place. The dream was always the same, involving her being fucked by at least six men, all of them with featureless faces, and her begging them to fuck her again. After they had shoved themselves into her mouth and pussy, and sometimes her ass, she always ended up in her dream alone in the dark and weeping for someone else to fuck her some more. That was when she always woke up feeling empty and depressed.

The problem was that she actually had sex a few times since then. With her new found confidence, she had the nerve to not only talk to some men but even invite them to spend the night with her; in fact, earlier that night she had just had sex for the third time with some cute guy she met at a party. She enjoyed the feeling of his body on top of her and pushing his cock deep inside her, but the truth was that she just couldn't orgasm. She faked it, of course, and he left her apartment feeling gratified while she still yearned for the exhilaration she felt at the Guess game.

The thought that upset her most, however, was that maybe she could never be satisfied having sex with just one person ever again. Maybe that night of orgasms with that group of people ruined her so that the only way she would ever orgasm again is by being fucked by multiple people. She wished with all her heart that it wasn't true, but her dream and her unfulfilling night of sex made her wonder.

Her phone suddenly whistled, notifying her that a text had just arrived. She looked who it was from and saw it was Peter. Danielle had just gotten to the point when she wasn't obsessed with what he told her three weeks ago and was just starting to breathe easier. Since she hadn't heard from him in all this time, she thought that he didn't have any videos of her after all. Or maybe his fingers slipped while he was jerking himself off and erased everything. Her blood froze when she saw his name and she almost turned her phone off, but curiosity got the better of her and she clicked on his message. "Come over now" was all it said.

She typed back, "Fuck you," and slammed her phone on the bed. Glancing at the clock, she saw that it was 1am, which made her even more irritated that he would be texting her so late.

Another whistle sounded a few seconds later, so she clicked on the new message. "Now. Or else." Chills ran down her naked body, remembering his threat to send her videos to her parents, coworkers, and friends. She thought about having him arrested for extortion, but she didn't have clear evidence yet, and even if she did she could imagine the looks of disapproval from the police and prosecutors when she explained what she was doing in the video and why.

She decided to avoid confrontation and typed, "What do you want?"

"My hour. Now," along with the address, was the only reply she got. She told herself she did not want it see him ever again, but she decided to go and see what he wanted her to do. As the memories from him during the game filled her head, she felt her nipples harden.

She hopped out of bed and started putting some lingerie on, but then she remembered last time he spoke to her, he explicitly instructed her not to wear any. So instead she threw on a shirt and sweatpants without any underwear, and the feeling of her erect nipples on her 38-inch chest rubbing against the fabric was more stimulating than she expected. Then she got in her car and followed her phone's GPS directions to the address.

She parked and crossed the street to a townhouse with the matching house number. It was late summer, but the temperature was still warm enough that she didn't need a jacket as she knocked on the door.

Peter opened the door and said, "Come in and sit down."

She snorted, "Hello to you, too."

"Sit," he commanded, which she didn't appreciate but decided to let it go for now. She walked into the place and saw every light was off except for a single lamp in the living room beside an ordinary wood chair.

She walked over and sat down in a huff, "What do you want?"

"Take off your shirt." Peter had already taken off his shirt, and now he was unzipping his pants.

"I don't owe you an hour! So I'm not going to..."

"Now."

She fell silent since there was something in his voice that made her unsure exactly what would happen if she refused. She reluctantly pulled her t-shirt over her head, and her bare breasts hung open.

"And your sweats."

She opened her mouth to protest, but instead she just grimaced as she pulled her pants down over her curvaceous hips and let them fall to the floor. She could feel her pubic hairs get goosebumps now that they were exposed.

"What are you going to do now?" She heard some shuffling and saw three other men, completely naked, step out of the shadows. "What is this? Are you going to rape me now, you motherfucker?"

"You can leave if you want, go ahead." Peter held his hand out towards the door. She picked up her clothes but didn't move. She told her body to start walking, but for whatever reason she stayed motionless, not moving a muscle, other than to stare at the naked men surrounding her. She told herself that she needed to secure the videos first, so she dare not leave yet. But what she was really thinking about was imagining them all fucking her and how their cocks would feel moving inside her pussy, which she could feel becoming wet, and what their cum might taste like. After a minute, she was still standing there.

"Do you want to leave or not?" Peter's lips twisted into a smirk that she found just as annoying now as she had last time she saw him.

"I... I..." But she found she couldn't come up with an answer. She wasn't sure what answer she wanted to say. She knew the correct answer was to leave and never look back. But as the chill of the air enveloped her naked body and she looked at all of the men standing around her, her body refused to go anywhere. She has already been standing there silent for at least a full minute, and the awkwardness of each passing second made it even more difficult for her to find the answer.

Finally, Peter walked up to her and after a few seconds went by, "Put your hands behind you." She hated the sound of his demanding voice, but she told herself as long as he had that video, she had to do whatever he says. He grabbed her tits and squeezed them until she winced in pain. Then he moved one of his hands to her crotch and thrust two fingers into her soaking wet pussy. She wanted to tell him to get his fucking hands off of her, but the only sound she made was a low moan of approval that she immediately regretted.

He slid in and out of her for several minutes, all the while squeezing her breast with his other hand and pinching her nipple, as the other men continued staring at her. She could see the lust in their eyes, and she could feel an orgasm start to form within her. The rest of them walked up to her until they were encircling her just a few feet away.

"You made a promise, and I expect you to honor it." He stared into her eyes with a leering smirk. "Just one hour, and I'll give you the video." Her face was set in a scowl, but she did like how his hands felt as they dug into her soft flesh. She looked around and saw the other men becoming erect and holding their stiff shafts pointed at her, and she became wetter than any time in the past few weeks.

The rational part of her brain was insisting that she tell them all to go fuck themselves and go to the police, but she was still afraid of what Peter might do with the video. As the spongy walls of her soaking wet vagina swelled around his thrusting fingers, she figured giving him and his friends one stupid hour would probably be the simplest way to end this. Plus if she were being completely honest, she did promise this hour to him if she bailed on the game, which technically she did. She sighed, "Fine. What do you want me to do?"

"Give all of us a blowjob." She looked down at the four erections pointing towards her, and she instinctively licked her lips which she was immediately embarrassed about doing. She didn't recognize any of the other guys, so she assumed they were some asshole friends of Peter.

She reluctantly got down on her knees in front of them all and felt the plush carpet beneath her knees.

"Tell you what," Peter laughed, "I'll give you a chance to end this sooner." Peter leered at her as he slid a blindfold over her eyes and Danielle found herself in total darkness and unable to see. "After you give all four of us a blowjob, if you can guess which one is me, we'll end this whole thing and you can have the video."

"And if I can't?"

"Then we keep going until my hour is up." He laughed and heard the sound of shuffling all around her. The men were clearly changing positions, and although she tried to keep track of where Peter was moving, she quickly lost him.

When she felt someone's hand rest on the side of her head, she opened her mouth and felt a warm, soft shaft slide into her wet mouth. As she slid her tongue up and down his cock, she felt someone grab her legs. Then as she heard a pair of handcuffs being strapped around her ankles, she felt her arms forcefully yanked behind her. She felt another pair of handcuffs click around her wrists, and when she pulled on them, she realized the chains had been wrapped around each other.

The chains of both handcuffs were extremely short, only three inches, so her hands and feet were all practically on top of each other. Her back was now arched at a painful angle, and she struggled a little to get into a better position that didn't hurt her spine.

She was about to protest, but the man in front of her grabbed her hair and jerked her head forward all the way onto his cock, and she gagged a little as the tip of his dick rubbed against the sides of her throat. He thrust himself hard into her mouth by slamming his body into her face as hard as he could, and she tried to relax the muscles of her neck so that she could swallow his cock without too much pain.

She felt him grip her hair tight and grab the side of her head, then he pushed his cock down her throat as far as he could and held her tightly so she couldn't move. She struggled to breathe but he was too strong to let her move, and with her arms shackled behind her, she couldn't do anything to stop him. He kept her still so that she was deep throating him, and she could feel his cock throbbing within her esophagus.

He shoved himself into her mouth several more times, each one more forceful than before. Just when she thought she might pass out, he relented and let her go. He pulled himself out of her and she desperately gasped for air. She managed to get a couple of breaths before another cock was crammed into her mouth, and she wrapped her lips around it and sucked hard.

Because she was blindfolded, she wasn't sure who was moving behind her and kneeling. But whoever it was, she felt his hands reach around her body and squeeze her nipples. With an erect cock filling her mouth, she could only groan in pleasure as he kneaded her tender breasts and dug his fingers deep into her mounds of soft flesh. When he took her erect nipples between his fingers and pinched, she felt an orgasm approaching.

Her head was being held still as the man in front of her hammered his cock deep into her mouth, as the person kneeling behind her continued rubbing her massive chest. She moaned in appreciation as her tongue explored the cock ramming into her neck. When her nipples were rolled between his clenched fingers, she squealed with pleasure but was muffled by the cock plunging fiercely into her throat. She rocked her hips hopelessly against the air in front of them, wishing one of them would just touch her clit so she could cum.

Suddenly the cock in her mouth was pulled out and drops of pre-cum splattered on her cheek. The man behind her stood up as well. With the blindfold on, she couldn't see what was happening, but when she felt the fingers pulling on her hair, she opened her mouth as wide as she could to let another cock shove into her mouth. Whoever was holding her hair was pulling so hard that the follicles in her skull felt like tiny needles of intense pain.

But that was nothing compared to the pain of the cock pummeling into her mouth like a jackhammer. He was slamming his body into her face at least three or four times a second, and the intense grip he had on her head made it impossible for her to stop for a breath. She strained against the handcuffs pulling her arms back and thrusting her immense, jiggling breasts forward, but she was unable to free her hands.

She felt the weight of someone kneeling behind her before she felt a pair of large hands grab her tits and squeeze her nipples hard. Her wet pussy was throbbing with pleasure, but the man in front of her continued to batter his cock deeper and faster into her mouth. The sound of the flesh on her forehead slapping against the skin of his hairy crotch was like a muffled woodpecker rapping against a helpless tree.

Danielle could feel some pain in her back as the incessant battering against her face was starting to take its toll. She thought about biting down on the cock in her mouth to get his attention and force him to stop. As the wetness of her pussy streamed down her thighs, however, she could feel the beginnings of an orgasm.

She realized she hadn't been able to orgasm with the last three decent guys who had performed loving, gentle sex with her, but merely giving blowjobs to complete strangers who were treating her with cruel mercilessness had her on the precipice of climax. That awareness made her feel like such a slut that a single tear fell down the side of her cheek as she sucked as hard as she could on the cock hammering inside her accommodating mouth.

Air was no longer getting to her lungs, and she could feel herself start to pass out, as the fingers around her sensitive tits continued to squeeze and dig into her soft flesh without a modicum of tenderness. Suddenly she could feel the cock in her mouth throb and soon her mouth and throat were filled with warm, salty cum.

She swallowed as much as she could as the cock continued to thrust in and out of her. The dick soon slowed down, and as she took a deep breath through her nose, she gave the jism-soaked shaft one long, slow suck as cum spilled out and over her chin before it dripped onto her tits.

When the cock was finally pulled out of her mouth, she took a deep gulp but there was still cum in her mouth as the next cock was pushed within her jism-covered lips. Her jaw was already becoming tired from the constant sucking and ramming, but she eagerly opened wide to allow the dick to thrust deep inside her throat.

Her breasts were beginning to ache from the intense squeezing, even the pain from the fingers clawing at her helpless tits made her pussy throb with stimulation. She could feel two hands on each side of her head hold her still as the man crashed his cock into her mouth repeatedly. After he violently thrust himself into her several times, her body started to quiver. All she needed was one second of clitorial stimulation and she would erupt.

Alas, with her knees spread wide and no assistance from the men, she lacked the stimulation necessary to finish what could have been a mind-numbing orgasm.

With a few more thrusts and her strong sucking on his stiff shaft, she felt him swell in her mouth before a wad of cum exploded down her throat. The warm, sticky jism felt nice as she swallowed some of it down, but then he pulled his cock out of her and, still holding her head firmly in place, wiped his dick on her face until globs of cum covered most of her face that wasn't under the blindfold. She stretched her tongue out as far as she could to lap up what cum she could reach as the hands on her tits clenched so hard that she gasped.

"So," she heard Peter ask, "which one was me?" She could practically hear the vile snicker in his voice.

"The last one." Even though she was grateful to find sexual satisfaction, she hated Peter for the contemptuous way he wiped his cum off on her face. "I doubt anyone else could act as despicable as you."

"I hate to tell you this, but no, that wasn't me." Danielle tried to remember the faces of the other men to think of who among them would have behaved that way, but she honestly was too busy thinking about their cocks to have spent much time focused on their faces. "I have to admit, that did look like fun. You sure seemed to enjoy it. Maybe I'll try that sometime." The laughter among the group of men made her sneer with contempt as she felt another glob of cum slide off her cheek and fall on her breasts.

"In fact, I wasn't even one of the two guys who cummed on you, and I have to say me and my friend are a little envious." From the sound of his voice, it seemed as though Peter had moved behind her, and as he continued talking, she felt the handcuffs on her ankles fall away. "So here's your next opportunity to end this."

"I want to fuck that awesome pussy of yours. While I'm doing that, if you can get my friend here to cum, then same as before, we'll end this and you can leave with the video." Danielle was lifted onto a plush ottoman and she laid on her back with her hands still shackled in handcuffs underneath her.

"You ready?" She was still blindfolded so she nodded in agreement, which made Peter laugh. "I was talking to him." She hated them all for laughing at her, but she hated herself for nodding so eagerly as though she couldn't wait for the two of them to fuck her. But as her pussy became soaked with anticipation at being fucked by multiple people for the first time since the game, she felt a strange impatience for them to start.

As her head dangled off the edge of the ottoman, she felt a pair of hands on her face and neck grab her as a stiff cock was pushed against her moist lips. Her legs were thrown apart and she could feel Peter rubbing his dick around the damp folds of her pulsing cunt.

"Go!" Instantly the two men shoved their cocks into her pussy and mouth respectively and the two of them began thrusting inside her as hard as each one could. She could already feel an orgasm begin to build inside her, and she cursed herself for being turned on by the two of them exploiting her powerless body.

Her enormous breasts heaved up and down as her body was buffeted back and forth between them, but she was determined to win this round. She ignored the weary muscles along her face and jaw and she sucked on his cock with an intensity that made him gasp, "Oh shit!" His balls were resting on her nose as he shoved his cock so far into her mouth that she could feel him throbbing along the sides of her neck.

She felt Peter start thrusting even faster, and the slapping of his flesh against her groin filled the air. Her tits were flailing in every direction now as he pounded against her, and she ignored the discomfort of the handcuffs around her wrists digging into the small of her back beneath her.