“We are not playing Truth or Dare! Are you joking? I’ve always hated it," said Melissa. She was always the most vociferous of the group, friends in the last year of college.
They were spending the weekend at one of their parents’ vacation house. After a lazy day by the pool, they had gathered at night in the family room of the house.
“Why not? We’re all sitting around drinking ourselves blind because we’re bored. Jill is falling asleep over there. Let’s liven things up a little.” That was Harry talking. The male equivalent of Melissa. Making things happen.
“The only purpose of Truth or Dare is to get people naked,” replied Melissa. “Aren’t we beyond that? Can’t we do something more creative?”
“You’ve got it all wrong,” Harry argued. “Truth or Dare is a sophisticated exploration of people’s inner truths. It’s a way of getting to know them, with defenses down. You learn things even one’s partner might not know. When in regular life do we ask the hard questions – or challenge someone to do a hard thing?”
“Yeah, hard things, like strip to the waist and shake your breasts,” Melissa retorted, perhaps remembering some particularly impolite prior T or D game.
“We’re not like that,” David said, although in truth he tucked that idea away for a later time. “Yeah, there may be some skin involved, but it’s all in good fun, among friends.”
“Tell you what,” Harry mediated. “Everyone gets one free pass. If you’re uncomfortable with either a Truth or a Dare, you have an escape. And of course, nobody’s in handcuffs; you can always flat-out quit the game, although you’ll be forever known as a quitter, a yellow-belly, and a wimp. But after your free pass, if you won’t answer a question, or don’t complete a dare, you lose an article of clothes.”
Melissa mumbled, “Well, what do you guys think?” to the other three women. “I guess I’ll do it if you will.”
“I like naked people,” said Margaret, a smile on her lips.
“Will the guys have to shake their parts, too? If so, I’m in,” said Jill, with a yawn. (Harry was right -- without something to liven up the night, she was about to drift off to sleep. She never could handle alcohol.)
Robin, the fourth girl, was not at all comfortable with this game. She was the shy one, and she had small breasts, unlike her friends. Her breasts never properly filled a bra. She wanted to keep her clothes on, not out of fear of being ogled, but the opposite. Robin was one of the group but always hung in the back, so to speak, lacking in self-confidence. She was too timid to say ‘no’ to the game if the others were willing.
The guys of course were good with it, so that’s how it happened. Eight friends, four guys and four girls, were about to embark on a game of discovery.
“Great,” said Harry. “We’ll start to my left. Jill, Truth or Dare?”
Jill, in accord with the unwritten law of Truth or Dare, started with “Truth.”
“What’s your very best sexual experience," Harry asked. "And we want names, please.”
Jill smiled. It was a pleasant memory.
“It was that time my boyfriend Joe and I went canoeing on the Shawnee River. Heading back, we took a wrong bend in the river and ended up far from the campground. It was getting dark, so we pulled ashore to wait for dawn. We had nothing but a blanket with us. The night was cold, there was nothing to do, so we clung to each other for warmth under the blanket. We made love over and over under the stars until morning. We were so tired I’m not sure how we paddled. But it sure was worth it.”
“A sweet memory, Jill, thank you,” said Harry. “Billy’s turn. T or D? Jill, you ask.”
Billy chose Truth. It’s always a wait for someone to find the courage to be the first to choose Dare.
“Billy,” Jill asked. “What was your worst sexual experience?”
“Whoops, that’s a nasty question,” said Billy, but without rancor. “Melissa, is it ok if I tell that story about us from freshman year?”
Melissa replied, “Well, now that you’ve outed me, I guess there will be no peace until they hear it.”
Billy smiled. Not everyone knew he and Melissa had once hooked up.
“It was after a football game. My roommate was on the team, and the team always stayed late after a game for the coach to berate them – or as he’d put it, provide guidance. Melissa and I had just started dating. We decided to use that time to get to know each other better. We were butt naked in my dorm room, with me inside her, about to achieve some needed release, when my roommate came in. The coach’s son was sick so he had cut the post-game review short. Melissa screamed, threw me off her, grabbed her clothes, and ran into the bathroom. Then she fled. I was left there with a raging erection that wouldn’t go away for fifteen minutes after. Melissa and I never hooked up again. I’m still annoyed.”
“You poor soul,” commiserated Melissa. “You probably never had sex with anyone after that. Missed your one chance.”
There was laughter over the story. As Harry predicted, interesting facts about people were coming out. A sweet game, this Truth or Dare, right?
“OK, it’s Margaret’s turn.”
She turned to Harry. “Truth or Dare, Harry?”
Harry, whose idea this game was, felt obligated to move things along.
“Dare.”
Margaret thought for a while.
“Harry, I dare you to grope Billy.”
Silence. “You’re forcing me to use my free pass, aren’t you? You know I won’t do guy on guy stuff,” said Harry.
“Yup. Your choice.”
“OK, I use my pass. No guy stuff please.”
It was Harry’s turn, and he was already plotting payback for Margaret. He asked her to choose. She foolishly chose Dare.
“Margaret, I dare you to find out who among the guys is uncircumcised. And you’ll be blindfolded, so you have to do it by touch.”
“I can do that,” said Margaret with a smile.
But Johnny’s mouth dropped open. “Hey, is this her dare or ours?”
“Don’t get modest on me,” Harry retorted. “You’d normally be paying to have this done.”
Harry had a point.
A dish towel was tied around Margaret’s eye. The guys lined up. Margaret grabbed the first guy and thrust her hand down his trousers. She felt around the tip of the penis, moving her fingers back and forth to detect loose skin. The penis conveniently began to grow with the attention. That made the examination easier.
“Definitely circumcised,” she said and felt for the next guy.
Dave was next; he was hard before she touched him, in anticipation. Margaret massaged the penis, then for good measure, fondled the testicles. “Nope, this one is cut, too.” She completed her rounds and accurately identified who was and who wasn’t. (The guys confirmed.)
“That was the best dare ever,” Margaret smiled. “I’m beginning to like this game.”
The risqué nature of the dare, even though no skin had been shown, ignited the group. The “Dare” dam had broken. It was clear where this game was headed.
Dave chose Dare.
“Dave, your dare is to figure out who belongs to which bra. Each lady will place her bra on the table. You will need to assess who is the owner of each garment. If you get it wrong, you lose some clothes.”
With Dave’s back turned, the women reached under their clothes and removed their bras.
Dave grabbed the first one. It was a heavily padded bra, but still the smallest. That was easy. “This belongs to Robin.”
Robin took the bra back in silence. She did not like to acknowledge what didn’t require acknowledgment – that she had the smallest chest in the group.
Dave handled the second one, a light blue, medium-sized bra, with lace. He couldn’t tell from the size which of the remaining three ladies was the owner, but Margaret was wearing a blue blouse. “This is Margaret’s,” he said, accurately.
The remaining two bras were a dilemma. They seemed comparable. He eyed the chests of the two ladies but couldn’t tell.
“I need to do some research,” he said, as he walked to Melissa and placed his hands on her breast. He made a great show of trying to gauge the size, the heft on each breast, comparing it to the bra in his hand.
Then he went to Jill and did the same thing.
It was not-very-well-concealed groping, but the ladies were good sports and let him.
“OK, this one belongs to Melissa, and this one to Jill,” he declared.
But he got them backwards and had to relinquish his shirt.
Harry was pleased that his game was going well. Any initial reticence about its sexual nature has slipped away. He refilled everyone’s glass with the rum cocktail they were drinking. Alcohol is always an important part of truth or dare.
Next up was Robin.
“I choose Truth,” she said.
“Chicken.”
“Boo.”
She was greeted with derision for choosing the safety of Truth. Or what she thought was safety.
“Robin, how many sex partners have you had?”
Robin hadn’t anticipated that and was stunned. She cast her eyes down. This was not the reaction the group had expected.
“I use my free pass,” she said.
There was silence among the group. Clearly, Robin was still a virgin. No one had realized it, until then. She was not a beauty but had a pleasant face. It had to be her lack of self-confidence, and her fixation on the small size of her breasts, that kept her from finding a partner.
Melissa went over to her and gave her a hug. “You’re beautiful, Robin,” she said.
A tear formed in Robin’s eye. Then she began to cry.
“I’m not pretty like you girls,” she whimpered. “I’m flat-chested when all that guys want are big boobs.”
A sex game is fun when everyone has a young, attractive body when everyone is flirty. It turns sour quickly if the ‘wrong’ truth is revealed.
Harry spoke up. “Robin, we have a dare for you. And it’s one you have to accept. Dare to let us love you. All of us.”
“What?” was all that Robin could muster in reply before they all went to her. She was stretched out on the floor. One stroked her face, another removed her shoes and massaged her feet. Billy stroked under her skirt, rubbing the thighs, teasingly close to the center of her womanhood.
“Lay back and enjoy,” Harry said. “You’re going to have a sexual experience to remember.”
Some of the women said words of encouragement to Robin, as Dave and Billy began to remove her clothes. She protested meekly but did not stop them. Soon she was only wearing her panties. Her small but cute breasts were exposed. Billy used his mouth and sucked on the nipples, causing them to swell. Dave rubbed on the groin and used a finger on the lips of the vulva outlined in her panties.
“What are you doing,” Robin mumbled, but her heart was not in her protest. She was filled with pleasure as multiple partners excited her senses. Her panties grew moist.
“You and I are going into the bedroom, Robin,” said Dave. It was clear when was going to happen, and Dave did not want that culmination of pleasure, her first experience as a full woman, to be a spectacle.
“You don’t have to do this,” said Robin.
“I want to. You’re one of us. I want you to remember this night always. It’s going to be wonderful.”
They left for the bedroom. The game was halted while everyone refreshed their drinks and tried not to focus on what they knew was happening in the next room.
“Margaret,” Billy said, “I dare you to go into the bedroom.”
“Yeah, right,” laughed Margaret. “I feel like a protective mother, worrying if my child is okay. I’d love to know how it’s going, but I’m not going in there.”
After about fifteen minutes, Dave and Robin came out. Robin had a sheepish grin on her face.
“I’m ready to answer that Truth question now,” she said. Everyone laughed and Robin blushed. But it was all good-natured.
“Let’s get back to the game,” said Robin. “I’m the only one who’s been sprawled on the floor, naked. I want a chance to even the score.”
The mood of the group was clear. There would be no more “Truth” questions.
Johnny: “Dare”
“You are dared to unbutton your trousers, then choose a woman to take them off without using her hands.”
He chose Jill. He stood in front of her, his back against the wall. She got on her knees, and pressed herself against his groin, as she tried to grasp the zipper with her teeth. It was hard to hold onto the small zipper especially as Johnny moved around, reacting to the pressure of her face pressed against his private parts.
As she pushed into his front, a bulge appeared in the trousers, his body seemingly trying to ward her off. It was a battle, but Jill got the zipper down. Then she used her teeth to pull down first one side of the pants, then the other. In the process, Johnny’s underwear slid part way down, but that was just a bonus. He stood there, just clad in his half-lowered underwear, pubic hair peeking out. He yanked the underwear up. A fuller view would have to await another dare.
The group applauded Jill’s effort. It was a lot of work. But worth it.
It was Margaret’s turn. David asked her to choose.
“Dare.”
“You said you like naked people. I dare you to perform a strip tease for us, to music of your choice.”
“You’re getting right to it, then, aren’t you?” said Margaret.
“You can always use your free pass,” David replied.
“No way. I’ll save that in case this gets nasty. I can take off my clothes. I do it every night before I go to bed,” she joked.
An iPhone with a music streaming connection was produced, and the song “Like a Virgin,” by Madonna began to fill the room.
“Turn down the lights,” Margaret said. “If I’m doing this, there’s got to be atmosphere.”
The lights in the room were turned off, except for one small lamp, which provided soft illumination.
Margaret began to sway with the music, her shape moving in the dimmed light. She slowly began to unbutton her blouse and pulled it off. That blue bra which had appeared before now was in its true glory, filled to the brim with Margaret’s ample breasts. Her hands slowly inched down her skirt, revealing blue panties. She turned her back to the group, and loosened the clasp on the bra. She tossed the bra aside, continuing to move with the music. Then she slowly slid down the panties. Her naked back and buttocks tantalized, and the guys had to wait for her to turn around to reveal her full self. Which she did. Facing them, she leaned over and shook her breasts.
“That was for you, Melissa,” she said with a smile.
Everyone laughed, especially Dave.
Then she finished, to great applause. “You were great, Margaret,” someone cried out.
Margaret retrieved her clothes, but only put back on her underwear. She went back to her seat. The lights went back on.
“Who’s next, and how are you going to top that?” said Dave.
“It’s going to be difficult,” said Harry, “but we’re going to try. We’re going to have a double challenge. The next up are Robin and Billy. And it’s a joint dare for each of them.”
“What evil do you have in mind for us?” asked Billy.
“It’s easy. Billy is going to strip down to his underwear. Robin’s dare is to do whatever is necessary to arouse Billy. Billy’s challenge is to not become aroused. You have five minutes. One of you is going to lose. May the best man or woman win.”
Billy thought this was fantastic, having to hold out until the pleasure was too great to resist. Even if he lost, this looked to him like a win.
Robin, on the other hand, was petrified. She came into the evening a virgin. Now she had to play the vamp and arouse a man. Something she had never done before.
“I don’t know how,” she said softly.
“Don’t worry, men are easy,” said Melissa. “We’ll guide you.”
“I’m on it,” said Margaret. “I’ve always said I could teach this stuff.”
Billy, the ‘victim’ lay down on the floor in his underwear. His penis began to stir inside his shorts from all the attention, even before the festivities began.
“Billy,” Johnny said, “think of your sister. Think of your Aunt Mildred. Get that rod of yours back down.”
The guys became were a team too, to counter the ministrations of Robin and her supporters.
The battle was joined.
“Begin by rubbing his belly,” advised Jill. “Tease him, don’t touch the penis yet. Let him sweat a little, make him beg for it.”
“Use your other hand to rub inside the thighs,” suggested Margaret.
“Use your mouth and blow gently on his neck while you rub the penis,” said Melissa. “They love that.”
“Close your eyes and think of something else,” offered Dave. “Pretend you’re in church and it’s a boring sermon.”
Robin did all she was told, but it wasn’t working. There was only little movement inside the shorts. Either she wasn’t good at this, or Billy was too good at his task.
“You’ll have to step up your game,” said Margaret. “Reach inside and stroke the tip.”
Robin did as she was told, and Billy began to make little noises. But the penis remained soft in her hand.
“OK, we’re going to DefCon 3. You’ll need to put the penis in your mouth,” said Jill.
“I’m going to do what?” shrieked Robin.
“It’s like when you had a Good Humor icicle when you were a kid,” said Jill. “Remember sucking in all that flavor? Just do it.”
Robin freed the penis from the shorts and gingerly inserted it into her mouth. She slowly made little movements with her mouth.
“Do it like you mean it,” Margaret exhorted her. “No guy can resist this. Get going!”
Robin moved her mouth more forcibly and Billy began to moan.
Up and back, up and back, Robin massaged the appendage with her tongue and lips.
“Caress the balls while you’re doing that,” counseled Jill.
That did the trick. The penis grew in size until Robin was frightened at what she had unleashed.
“When can I stop?” she mumbled between breaths.
“I think that’s a full erection. Great job, Robin. You’re the winner,” said Harry.
Robin released the penis, which stayed erect in the air.
Billy looked around, “You can’t leave me like this. I need some satisfaction!”
“Sorry, that’s another dare, Billy. Maybe you’ll get lucky and one of these ladies will choose you for the next dare.”
There was general amusement at Billy’s plight, but no lady offered what he wanted.
“I think we need a group dare,” said Harry. “Everybody strip, and let’s get in the pool.”
Everyone was hot from the game, literally and figuratively. The clothes were shed in a frenzy and they raced for the pool.
“Great idea, Harry,” said Melissa. “Let’s play this game again tomorrow.”