20 Questions

Sylvia lay on the bed next to her boyfriend, lover and roommate. “Twenty Questions,” he had said. “That’s the game. I have a surprise, and you have to guess what it is.”

Sylvia looked at Ron, appraising him. He’d brought her upstairs and had her lie on the bed. Then he’d told her about the game. She was normally all for a little fun, but hated it when Ron had a secret. “Just tell me!” she said, curious.

“No,” he laughed. “You have to discover it for yourself. That’s the way 20 questions works.”

“Arrrgh. I *hate* that game. So repetitive.”

“So we change the rules. Let’s see… For every question asked, if the answer is ‘yes’ then the answerer — that would be me — loses an article of clothing. If the answer is no, then the asker — you — would lose one.”

Sylvia smiled. This could be fun, then. “When we run out of clothes, we move on to…other stuff.”

“Sounds good to me.”

“I’m going to like this game,” Sylvia said. “Prepare to be stripped.”

“We’ll see…” Ron said. “So, start with your questions. I’ll tell you this: it’s an object, and it’s not an animal or vegetable.”

“OK,” she said. She turned in the bed and looked at him. He was sitting on the edge of the bed, with one of his legs dangling off the side, and the other tucked underneath. She pulled her legs in, and sat up, sitting cross-legged. “This isn’t another of your corny gifts is it? Just to get that out of the way.”

“No,” Ron said, and reached out to her. He began unbuttoning her blouse, but stopped halfway. Sylvia looked at him, and he said, “I’m done.”

“Trying to prolong it?” she asked.

“Yes,” he said, and began to unbutton his shirt, halfway.

Dammit, she’d been tricked. Maybe this whole thing was a gag, a joke on her. Something she couldn’t guess. “Is this a gag? Did Joe put you up to this?”

“No,” came the response. “This is not a gag.” He unbuttoned her shirt the rest of the way, revealing a lacy white bra. At least she had worn one of her nicer ones today. He pulled her shirt off, and she felt his hands at the snap of her pants. “And no, Joe didn’t put me up to it.”

“Arrrgh,” she growled, and leaned on her back. She pulled her pants off.

“Plain white cotton,” he said, caressing her revealed thigh.

“I didn’t know we were going to be playing sex games, or you’d have gotten the red lacy ones.”

“I’ll remember that for next time,” he said.

“OK,” Sylvia stopped for a moment. She had to think about what this. She was way behind and needed to figure this out. “What I know,” she thought, “is that I’m down to undies and socks, and he hasn’t taken his shirt off yet! I need to approach this more logically…”

She thought for a moment more and looked at Ron. “OK, is it bigger than a breadbox?” she asked.

“No,” Ron said, and pulled off one of her socks.

“Is it in the room with us?”

“Yes,” Ron said, and pulled off his shirt.

“Finally,” she said. “I’ll get you naked yet.”

“If you don’t, curiosity will kill you.”

Sylvia looked around the room. It was in here somewhere. “Is it…something I can see?”

“No.” As Ron pulled off her other sock, she mock kicked at him. “Only two more ‘no’ questions, and I have you at my mercy,” he said chuckling.

“I know, I know!” Maybe he was getting her undressed so he could put her in what he had bought…Maybe something sexy. “Is it something I can wear in bed?” Sylvia asked flirtatiously.

Ron laughed, and said “Why, yes it is something you can wear in bed.” He stood up and slid his pants down, bending so she could see his tight ass. She reached out and caressed it through his briefs. “Now wait, Sylvia. You’ve got a few questions to go before you can do that.” Ron sat back down, and faced her. He was still wearing socks, so he was one article of clothing ahead.

“Is it… lingerie?” she asked.

Ron smiled, “Nope.”

“Damn.” she said. She sat up and removed her bra, cupping her breasts and letting the straps fall. She slowly moved her hands down, revealing her breasts. She could tell Ron was watching as she undressed, and she had to admit she was enjoying teasing him.

“OK, then, is it something I could wear anywhere?”

Ron paused for a moment, and thought for a second. “Yes, I suppose you could wear it anywhere.”

Sylvia laughed, and pulled one of his socks off. “So is it clothing?”

He laughed then, “No, it’s not clothing. And you are naked.” He reached over, and took the elastic band of her panties, and pulled them down her legs. She lifted her ass to help him do it. She always enjoyed it when he did that.

Sylvia sighed. “I still think this is some kind of sex game.” Ron grinned at her, and she tried to divine whether it was or not. “So I think it’s some sort of sex toy — something I could strap on, maybe.”

Ron didn’t say anything. Sylvia looked at him expectantly. “That wasn’t a question,” he said.

“Oh, ok. Is it a sex toy?”

“No, it’s not!” he leered. He curled up next to her, and she felt his hand on one breast, and his mouth on another, his tongue flicking back and forth against the nipple. His fingers found her other nipple, and began twisting it a bit, bringing it to hardness. Sylvia moaned as he played with her tits. Then he stopped.

“You stopped.”

“Yes, it’s time for another question.”

“OK, is it…jewelry?”

“Yes, it is.”

“Ooooh.” She said, as she sat up, and pulled off his other sock. “You’re just down to one garment, now,” she said, as she rubbed the front of it with one hand.

“Now, now,” he said, as he wagged his hand. “You’ve still got two questions to go before you can do that.”

“But I know you like it.” She squeezed his hardening cock with her hand. “I can just tell these things.”

“Now, come on Sylvia. Play fair. Ask another question.”

“OK. It’s not cheap is it?” she asked, playfully.

“No,” he said laughing. He lowered his mouth to her breast, and sucked it in. His free hand slid down between her legs, and began caressing her wet pussy lips. She pushed forward with her pelvis, trying to get him to slide his fingers inside of her. He just kept rubbing outside, up and down her mound, pressing down over her clit, but not sliding inside.

She gasped as he nipped at her breast in time with his finger’s pressure. Then he lifted his hand off her mound, and pulled his lips from her breast. It was time for another question.

She smiled at him; she knew what it was, now, or thought she did. The question was, did she want to prolong it or not. She thought about his mouth on her breasts. Yes, prolonging it would be a good thing. “Is it a…neck lace?” She asked.

“No,” he said, and lowered his mouth to her other breast. This time his finger slid inside of her. His middle finger found her clit, and moved it just so, in little circles. She gasped and sighed and thrust her pelvis against his hand.

Before he could stop, she asked, between gasping breaths, “Is it earrings?”

He lifted his mouth off her breast, and whispered “No.”

Then he did stop, and she cried out, “No…” But he was moving, sliding down her body, promising something more. She lifted her legs, and separated them, and he settled in between her legs, his mouth on her pussy.

She felt his hands separate her pussy lips, and then his tongue, sliding from the bottom to the top, stopping there, resting on her clitoris. She gasped as he played with it, tonguing it gently, tap, tap tap, sending little pulses of pleasure up and down her spine.

Sylvia wrapped her legs around his head, and pulled him to her. He sped up, going faster. Ron’s tongue began doing what seemed like a wild dance then, lick, twirl, tap, twirl, tap, tap, twirl.

“Yes yes, yes,” Sylvia cried, keep doing that.” He complied, twirling his tongue around her clit, and she moved back, towards him, grinding her pelvis into his face and mouth. The pleasure built higher and higher, and she pulled him tighter and tighter with her legs, and then she came, crying out in ecstasy. She let him go then.

He looked up at her with a sparkle in his eye. “You better get it right, now. I’m not sure I could survive another ‘No’ answer.”

She laughed happily. “OK, sweetie. Is it a ring?”

“Yes,” he said. She sat up. He lay down on his back, and she pulled his underwear off of him, releasing his cock. It sprung out from behind his briefs, standing tall and hard. She ran her hand over it. “You have to ask a question!” he admonished.

“OK. Does the ring have a stone?”

“Yes, it does,” he said. She smiled at him and ran her hand up and down his cock, stroking it. She sped up, faster and faster. She could see the look of excitement on his face as she stroked his cock. He stretched out, pointing his toes like he always did right before he was going to come, and she stopped.

He groaned, painfully. “Time for another question,” she said. “Is it an engagement ring?”

She saw a twinkle in his eye. “Yes, yes, it is.”

He started to move, as if to get it, but she stopped him. “I get my prize,” she said, and lowered her mouth over his cock. He groaned happily and lay back down.

Sylvia moved slowly up and down his cock, running her tongue over it, sliding her tongue between his slit. She took a hand and cupped his balls, gently playing with them. She moved a little faster, and felt him begin to move, just a little bit. She squeezed his balls, and began sucking hard. “It won’t be long now,” she thought.

And she was right, she squeezed a little harder on his balls, and he went rigid, pumping his come into her mouth. Sylvia moved a couple more times, up and down his cock, cleaning it off. She looked up at him, and swallowed.

Ron gazed down at her, his eyes twinkling, obviously happy. He moved languorously, to the side of the bed. He reached down between the mattresses underneath where he had just lain, and pulled out a small jewelry box. He opened it up and showed it to her.

“Now it’s time for my question,” he said. “Will you marry me?”

Sylvia looked at the ring — it was beautiful. But even more beautiful was the man holding it. He had completely surprised her by this, and now she had to think. There were so many questions in her mind, so many doubts. But deep in her gut, she knew it would be ok. “Yes,” she said. “I will.”

He slid the ring on her finger, and kissed her. As they kissed he rolled her onto her back, and slid between her legs. He was hard again, already. She looked up at him quizzically

“The asker gets a prize if the answer is yes.” he said, matter-of-factly.

“Oh,” she said, and slid her legs wide apart. “Then, my love, my fiance, come and claim your prize.”

She looked up at him, as he slid between her legs, and then between her nether lips, sliding all the way home. One of his hands brushed her hair. “You, he said are the most wonderful prize of all.”

Sylvia felt a tear leave her eye. “Take me,” she whispered.

And he did, several times.

Without question.