Guess: The Ultimate Sex Game

To anyone who was expecting this story that I promised a while ago, I apologize (life events happen). But at long last, here is Part 1. Part 2 will come in another week or so (I hope).

Guess: The Ultimate Sex Game

Part 1

Danielle was struggling to ring the doorbell while holding the bottle of wine and plate of cheese, but she somehow managed to use her elbow to announce her arrival. She had been to her friend Stacy's apartment many times before so she wasn't sure why she was having so much trouble tonight. It was probably the nervousness.

The door opened and Danielle saw the familiar warm smile she always looked forward to seeing. "Hey there! Glad you could make it! Let me help you with that!" Stacy grabbed the plate of cheese from her hands. "Come in and say hi to everyone! I think you know everyone already." Stacy had invited Danielle over tonight along with several other friends of hers. Danielle was good friends with Stacy, whom she has known for many years, but she didn't know the other people in the group very well, other than the few sporadic times she saw them at various parties.

As Danielle took off her jacket, she smiled at everyone in the room. Louis was a nice looking guy who, like her, had graduated college a couple of years ago but didn't really stand out personality wise. Remmy was a little older and worked as a bartender, which seemed to fit him well considering how socially outgoing he was. Christy was basically the same age as the rest of them, but Danielle always found her vapid with no curiosity about much of anything outside of her latest issue of Cosmo.

When she saw that Peter was there, she groaned internally. Peter was one of those good looking guys who knew he was a good looking guy and strutted around with an arrogant charm that everybody else found endearing but she always found repulsive and a little creepy. She politely smiled at him, but the way he smiled back at her made her skin crawl.

"So is everyone ready to play?" Stacy asked the crowd who all, except for Danielle, responded enthusiastically. Danielle wasn't as thrilled, but Stacy had repeatedly begged her to come tonight. A friend of Stacy's had found some board game on the internet that was purported to be the sexiest game in existence. She couldn't believe Stacy actually paid good money for this game and invited all these people to come play. When Stacy asked her to come, Danielle knew it was terrible idea and that she shouldn't do it but she nevertheless agreed after Stacy had relentlessly pleaded for her to take part.

"How about you, Danielle?" Peter gave her a smirk that was pure dare. He looked up and down at her. Danielle had worn a modest blouse and blue jeans, but his eyes seemed to be undressing her as though he was trying to imagine what the skin of her 38-inch chest looked like, which made her a little uncomfortable. Her sizable chest had always been a prominent feature of her 5'7" frame and all her life she had become accustomed to men lustfully looking at her extra-large distracters, but now that she was about to play some sort of sex game with these strangers, she felt extremely self-conscious about her body.

"I'm ready!" she said, looking Peter straight in the eye. Sure, Danielle wasn't the most sexually adventuresome person, she knew that about herself and this was not the sort of game she would have wanted to play if it were up to her. But there was no way she was going to be intimidated by him.

Peter guffawed, "Right." And the others laughed as well. Danielle had always had trouble making friends throughout her life. People had told her she was "stuck up," "conceited," "too goody-goody," "better than everyone else," and "egotistical." She had never found it easy to lighten up and go with the flow. During her psych course, she discovered the paragraph on controlling personalities described her way too well, and ever since then she made a point to do things outside her comfort zone every so often. Now that she was here, though, she wondered if maybe this particular event was more than she could endure. Looking at the faces of all these people eyeing her with suspicion, she could tell they wondered the same thing. Danielle decided to shove her fears aside and was determined to prove them, and herself, wrong.

"So what are we supposed to do?" Christy asked in a particularly bubbly way that made Danielle wince.

"Basically we work our way through this booklet here," Stacy said reaching into a square-shaped duffel bag and pulling out a scarlet book with gold letters saying GUESS WHO? emblazoned on the front, the same word printed on the side of the bag. "There are a bunch of challenges, and whoever gets the most points wins."

"Great. What's the first challenge?" Danielle asked, hoping to get this game over with quickly.

"Let's see... yadda yadda..." Danielle thought about taking the booklet from Stacy, who was not the fastest reader but Stacy continued, "ok, here it is, Challenge One. Everyone must take off all their clothes except for underwear. The first person to get everything off gets five points, the last person gets negative-five points. Everyone else gets three points."

"I've set my phone to countdown in five seconds, is everyone ready?" Danielle was already feeling uncomfortable at the thought of undressing in front of other people she barely knew, especially one whom she particularly despised. But she was determined to see the game through.

BEEP! At the sound of the phone, everyone started frantically taking off their shirts and pants. The room was filled with arms and bodies in constant motion and articles of clothing being flung in every direction. "Done!" Peter exclaimed, and Danielle took a quick glance at him and saw that he was in fact completely naked except for the boxer briefs that clung tightly to the bulge in his crotch.

Stacy cried, "Done!" next and Danielle cursed herself for having trouble pulling her pants around her ankles. When at last she did, she triumphantly said, "Done!" as well, as did all the remaining people.

Christy asked, "Who came in last?"

Peter had a wicked smile on his face. "Well, Danielle still has her socks on, so she's not actually done yet." Danielle looked down and sure enough, she had forgotten all about her socks. She cursed herself as she pulled her stupid socks off. "And it looks like she came in last." Peter laughed. It had only been one challenge and already Danielle hated the sound of his voice.

"Ok, Challenge Two," Stacy said reading through the next page in the book and reaching into the GUESS WHO? bag to pull out three blindfolds. "Says here that there are two stages to this challenge. For the ladies, we need to put these blindfolds on and put our arms behind our backs, then each guy has one minute to put their hands on our bras. After each person has a turn, we ladies have to write down which guy was first, second, and third. Each correct answer earns three points."

Danielle could feel the eyes of the men sneaking looks at her breasts, just as she always knew when men were looking at her bosom. She stared at Stacy incredulously, "Wait, I'm supposed to let these three guys just... fondle me?"

"I told you inviting her was a mistake," Peter said to Stacy. "I knew she would ruin everything."

"I'm not trying to ruin anything, I'm just not... comfortable with this part of the game, that's all." Standing there in a thin, skin-tight lace bra and panties, Danielle felt a chill run through her body that made the hairs on her arms covering her chest stand on end.

"Face it, you're a prude." Peter said to Danielle as he snatched his pants off the floor before turning to the others. "Forget it, she's not going to go through with the game, so let's stop now and get someone else who's capable of having fun and isn't so uptight." Everyone else reached down and grabbed their clothes as well, some of them looking at Danielle with a disappointment as if all their perceptions of Danielle as a prissy, timid puritan had been proven.

"No, wait, I didn't say I wouldn't. I was surprised." Danielle's voice sounded more sheepish than she wanted. "Come on, let's keep going."

Peter kept putting his shirt back on. "You'll just balk at the next challenge. Or the next one after that. Just forget it." Danielle knew he was using reverse psychology and that he was manipulatively goading her. She knew that, but she couldn't stand having that arrogant asshole grandstand in front of everyone as if he had proven beyond a shadow of a doubt what a sexually repressed person she was.

She could feel part of her screaming for her to forget these people, stop caring what their opinions of her are, and walk away now while she could. But the part of her that had always motivated her to succeed took over and defiantly gritted her teeth, "I said, I'd finish the game and I meant it."

"Or what?" Peter looked at Danielle.

"What do you mean?"

"I mean I want some assurance that you're not going to wimp out at another challenge." Peter had a way of speaking as if he was enormously pleased with the sound of his own voice. "So what are you willing to do if you don't finish the game?"

"I... I don't know."

"Tell you what, here's the deal. If you don't finish the game, then I get one hour with you to do whatever I want to you." Peter was standing so close in front of her that she could catch a whiff of garlic from something he had eaten earlier that day. "You'll let me fuck you, you'll suck my cock, I can fuck you in the ass, whip you, ANYthing I want for one whole hour."

"What? I'm not going to agree to that!" She thought this would prove to everyone what a monumental asshole Peter was, but as she looked around the room, the only smirks and looks of disappointment she saw seemed focused on her.

"What did I tell you, she's too much of a prude to do this." Peter turned and started picking up his clothes again, and the other guys did as well. "Let's go home and find someone else tomorrow." Christy seemed unsure what to do next, but she started scanning around the room for her belongings also.

Danielle said in a determined voice, "I said I'd finish this." But as soon as she heard her own voice, she knew she sounded as skeptical of her own words as it sounded to everyone else.

Peter stared intently at her, "Then you won't have a problem agreeing to my deal, right?" Danielle could feel her face become warm with anger. She looked over at Stacy, who was standing there helplessly staring back at Danielle with eyes that pleaded for her to agree. She looked at the others who had a judgmental gaze that was accusing her of being a stuck up bitch with a superiority complex.

And then she coldly looked back at Peter who had such a sickening, lustful smirk on his face that she would have done anything to embarrass him the way he was humiliating her right now. "Fine. You've got a deal." Danielle said flatly.

Stacy walked up to Danielle and handed her one of the blindfolds. "Remember, we're all doing this. So just relax and have fun, ok?" One of the reasons Danielle felt a special bond with her friend was the sunny disposition she displayed whenever Danielle was feeling low or dejected, but at this moment, Danielle couldn't help but find Stacy to be naïve and simplistic.

Danielle took the blindfold saying, "Thanks." As she strapped the elastic band around her head that held the cotton cover firmly over her eyes, she shook her head at herself. She knew she had a tendency to be dark and, if she were totally honest, a little prudish. She was completely blind and not a single speck of light was coming into her vision. Danielle remembered the times she had felt envious of all the women she saw at the beach who could wear skimpy bikinis without any self-consciousness, including Stacy. Danielle knew she did need to relax a little. No, a lot.

Stacy called out, "Does everyone have the blindfolds on?" and both Danielle and Christy said yes. "And did someone set the timer?" A muffled mmm-hmmm came from Danielle's right, but she didn't know whose voice it was. She put her hands behind her back and waited for the challenge to begin.

BEEP! For Danielle the world was completely black but she could feel the fingers sliding over her bra. A few second later and she could feel those same fingers digging into her breasts in a way that made her squirm a little. She tried to focus on the side of the fingers and determine the size of the hands, but she had no idea. All she knew is that those fingers had caressed every inch of her sizable breasts.

BEEP! It only took a few seconds for another pair of hands to find their way to her breasts. Once again, she felt the cold fingers squeezing her breasts tightly. She gritted her teeth as the hands searched her chest for her nipples underneath the lace and, when finding them, pinched them as hard as they could. She listened to see if she could hear the other women grunting from discomfort but all she could hear was her own groans softly rumbling in her throat. She made a mental note to say Peter was second for her.

BEEP! These last hands were even rougher than the others. Because Danielle had always had sensitive breasts, she had always put strict rules on the few boys whom she had allowed to touch her chest. Feeling her breasts being brutally clawed at in such an aggressive way made her gasp in pain. What was equally humiliating, however, was that all the physical sensations on such a sensitive area was making her pussy damp, which she very much tried to ignore.

By now she was second-guessing herself and thinking this was Peter, but she didn't know who the first two were. Or maybe it was Louis, whom she didn't really know all that well, maybe he was capable of savaging grabbing her flesh? She tried to focus on the pitch of the heavy breathing, the height the person seemed to be, anything that could reveal who the person mauling her tender breasts might be, but it was difficult to piece together any possible evidence with her chest throbbing in agony.

When the final beep sounded, the hands squeezed hard one last time before releasing. She heard the sounds of footsteps backing away from her as she tried to take the blindfold off, but by the time she had slipped the elastic band through her hair, all the men were in a huddled group. Danielle noted that Remmy was the man closest to her, but she realized that for all she knew, they had switched places in order to confuse her. "Write down the order of guys who had touched you on this piece of paper," Stacy said sweetly as she handed a pad and pencil to Danielle and Christy while keeping one for herself.

Danielle stared at the blank piece of paper not having any idea which guy belonged to which hands. She looked over and saw that Stacy and Christy had already finished, so she took a breath and wrote "Louis, Remmy, Peter" on her paper.

The guys took all three pieces of paper and looked each one over. "Wow Christy, you got all three right. You get nine points. Stacy, you got one of three correct, so you get three." They giggled at each other while looking over the final paper. "Danielle, I can't believe it, but you didn't get a single one right."

Danielle tried to ignore the warmth in her cheeks, hoping no one noticed her embarrassment. She hadn't felt this embarrassed since she was 14, when one night she let a boy she liked at church camp feel her already well-developed breasts. After he told everyone what happened, she had to endure every boy at camp for the rest of the week continually asking if she'd let him squeeze her titties, and she could even feel some of the male counselors giving her leering looks as well.

"Alright, now it's the guys' turn. Put on these blindfolds and put your arms behind your back," Stacy commanded. "Ladies, we have one minute with each guy to touch their underwear and anything underneath," unable to stop herself from giggling. "And then they have to guess which of us was in which order. I'll set the timer."

As all the guys put on their blindfolds, Danielle surveyed all of their bodies and noted how sleek and muscular they all were, Louis in particular was well-toned. Danielle looked at the other women and they randomly switched places and stood in front of their respective man. Danielle was left standing a few feet in front of Peter, and as much as she loathed the thought of him having touched her body in any way, or the thought of touching him sexually, she had to admit that he had an attractive physique.

BEEP! Danielle hesitated a few seconds before lightly pressing her palm against his groin. She rubbed her hands clockwise a couple of times and could feel his penis stiffening. As she continued rubbing, his cock quickly became hard and upright. Her chest was still throbbing in pain, so she decided to give his penis a good hard squeeze in retaliation for whoever had done that to her, even if it wasn't him. But as she clenched her fist as hard as she could, she looked up and saw Peter with a contented smile that made her sick to her stomach.

BEEP! Danielle was grateful to move on to Remmy, and as she reached down she of course found his cock already very rigid. She moved her hand up and down his shaft and could feel him become engorged. She liked Remmy, at least as much as any of Stacy's other friends, so she didn't mind seeing his bright smile as she stroked his dick. In fact, she could feel herself become more damp in her groin as she moved along his stiffness.

BEEP! She wished she had more time with Remmy, but she obediently went to Louis. She knew she had met him before at other parties, but she tried to remember which ones and what they had talked about, but for the life of her she couldn't remember anything about him. She stroked his cock slowly a few times, and smiled when she heard him groan in satisfaction. Then she decided to grab his cock and thrust her hand up and down as fast as she could. Within seconds, Louis's entire body began trembling and he was gasping for air. Danielle couldn't help but feel proud as she continued satisfying him. She was sure she could make him ejaculate before the beeper went off, so she was disappointed when the timer beeped and Louis was simply panting with no sticky spot on his underwear after all.

The guys wrote down their deductions for the names of the girls in order. Both Peter and Remmy got all three names correct, but Louis only got one and it wasn't Danielle. She smiled to herself that she was able to fool him by being more sexually playful than he gave her credit.

"Alright, the book says to tally up all the scores so far and see if anyone has a negative number. It looks like... Danielle is the only one who is negative so far."

"So what does that mean?" Danielle asked, not sure if she wanted to know the answer.

"According to the book, anyone who has a negative number after the first two challenges must do a Penalty Challenge. If the person is female, then..." Stacy's voice trailed off as she continued reading to herself. Without a word, she reached into the duffel bag and pulled out some dice and handcuffs. As she took a blindfold from Remmy, she said, "Danielle, you need to take your bra and panties off."

"You cannot be serious!"

"Come on, we're all adults here. Just do it. We'll all be naked before too long." Danielle could feel the lust in the men and the envy in the women. Her breasts have always garnered her attention, and usually not the kind she sought. She knew, though, that she had protested so many things already tonight, and it would be better to just reach behind her and unclasp her bra with as much pride as she could maintain. As her breasts jiggled free, she felt the cool air against her nipples that made them instantly erect. She pulled her panties below her rounded hips and let them fall to the floor.