Chapter 3
Never Have I Ever Played Strip Poker
Am I really going to play strip poker with my new Friend and a man I just met?
Derek parked the car, and he led Sheila to his friend Alexander’s apartment. Sheila was nervous since she didn’t know what to expect, but she was eager to find out.
Alexander offered them drinks with a gracious smile. She and Derek sat on the couch while Alexander chose a nearby chair. They made small talk and drank for a few minutes before Alexander leaned forward and set his drink down.
“Okay, I’ve got to know. What was going on with you two at the restaurant?”
Sheila turned bright red but said nothing, and Derek smirked.
“That’s what I thought. Did you have some kind of device?” he asked Derek. “I thought I heard a low buzzing noise a few times, but I wasn’t sure.”
Again, Derek remained silent. Sheila wondered if it was possible to die from embarrassment.
“Hey,” he assured her. “I’m not trying to embarrass you. It was sexy as fuck. I just didn’t expect—“
“I thought we were going to play cards,” Derek interrupted.
“Okay, okay. I can take a hint. What are we playing?”
Both men looked at Sheila. She downed the rest of her drink and stuck her hand out for a refill.
“Strip poker,” she said with a confidence she wished she felt.
The two men exchanged similar shit-eating grins. Alexander jumped up to grab the cards and a few bottles of water. Derek mixed her another drink, which she sipped.
They established the rules for the game and their clothing.
“If you get bored, or it’s not fun anymore, just let me know,” Derek reminded her.
“Thanks, but I don’t see how I could be bored with this company,” Sheila simpered.
A few hands in, it was obvious to everyone Sheila was a terrible poker player. She’d already given up both shoes, her bracelet, and her bra. All she had left was her dress and her thong. Derek hadn’t lost anything, while Alexander was down to his pants and whatever he wore underneath them.
“We can stop the game at any time,” Derek reminded her. “We don’t have to do anything you don’t want to do. You’re in charge.”
Sheila thought for a moment, but she was enjoying herself. She liked the way both men’s eyes followed her jiggling breasts whenever she gestured or moved. While she wasn’t an exhibitionist, she felt powerful and aroused by these two sexy men paying her such close attention.
She wasn’t ready to bring another person into her face-to-face sex games with Derek, but she wanted to play at least one more hand of cards.
Throughout the evening, she had drunk enough to feel flirty and confident, but not so much that she didn’t have control of her decisions or would have regrets.
When she won her first hand, she was thrilled to watch Derek strip off his pants. He removed his shoes earlier and hadn’t bothered to replace them before the game. Alexander stood up to take off his pants, which left him in just his boxer briefs. They left nothing to the imagination.
A few months ago, she would never have imagined sitting at a table in only soaked panties and a thin dress with two men similarly undressed.
“Are you up for one more round?” Derek asked with a grin.
Her mouth dry with excitement, she nodded, and he dealt another hand.
Sheila assessed the possible outcomes. Derek still had his shirt.
Unless Alexander won, he’d be naked at the end of this round.
Sheila couldn’t count on another accidental win.
If she lost as she expected, she’d have to choose between her dress and her thong.
She flushed at the thought of sitting topless with the two of them. Derek winked at her as if he knew her thoughts, and he very well might.
When the hand ended, Alexander won. Derek drew off his shirt, leaving him in only his boxer briefs, and then both men’s attention shifted to her. As Derek opened his mouth, probably to remind her again she had the power to stop the game, she whipped her dress off over her head.
Now all three of them sat around the table in just their underwear. Sheila’s nipples tightened further at the hunger in their gazes. She had to clear her throat twice before she spoke, and her voice was husky with arousal.
“Are we going to play some more?” she asked with a slight quaver.
“Let’s play a different game,” Derek replied.
Sheila was surprised. She wondered if this was another tactic to keep her from being overwhelmed. Before she asked, Alexander responded.
“What kind of game?”
“Never have I ever.”
“I don’t know what that entails,” Sheila said with a self-conscious giggle.
It felt strange, yet so thrilling, to sit around wearing only panties while they talked and acted as if everything were normal.
“It’s a drinking game, but it’s also a fun ice breaker.
You think of random things to say you’ve never done, and everyone who’s done it takes a drink.
‘Never have I ever called in sick to work when I was fine’ for example.
It’s silly, but it’s fun. We can find questions online, or we can make up our own. ”
“Sure, that sounds good,” she said.
Alexander agreed.
“I’ll start,” Derek said. “Never have I ever kissed a woman.”
Both men drank.
“My turn.” Alexander thought for a moment and then grinned. “Never have I ever played strip poker.”
Everyone laughed and drank. Sheila looked up questions on her phone, so she had her first one. She wasn’t quite brave enough to ask the questions she wanted to yet, but she hoped to work up the nerve.
“Never have I ever hooked up with an ex.”
All three grimaced and drank.
Derek’s turn again. “Never have I ever used a dating app.”
No one drank.
“Really?” Sheila asked. “I thought I was the only one.”
“I wasn’t interested in dating.” Derek shrugged.
“I’ve never needed one,” Alexander commented.
Sheila giggled again.
It was Alexander’s turn. By the glint in his eye, she expected something risqué.
“Never have I ever been to a strip club,” he asked.
Sheila smirked and took another sip. Both men raised their eyebrows as they lifted their glasses.
“I’d like to know the story behind that,” Alexander muttered.
“It wasn’t as interesting as it sounds. My college roommate needed someone to go with her for reasons that aren’t mine to share, so I went. It was the middle of the day and sad.” She took a deep breath. “But now it’s my turn.”
She tapped her chin in thought. Maybe one more round, and then she’d feel brave enough.
Instead, she said, “Never have I ever had an orgasm in a public or semi-public place.”
Alexander groaned, and all three of them drank.
“You guys are taunting me, aren’t you?” Alexander complained.
Derek snickered before he posed his challenge. “Never have I ever kissed more than one person on the same day.”
Alexander took another drink with no hesitation. Neither Derek nor Sheila did, but he stared at her intensely. He was giving her the choice to keep the game flirty or move it in a more physical direction.
Given the question she planned to ask next, she could have kissed him for his perspicacity.
So, she did. Sheila got up in just her tiny thong and walked over to his chair. Leaning forward so her ass was on display for Alexander, she put on a show.
Sheila and Derek exchanged a sultry kiss while she wiggled and writhed for Alexander.
Derek fondled her breasts while they kissed.
It turned her on even more that she was mostly naked while she kissed one almost nude man and was ogled by another.
She hoped both men would be as excited by her idea as she was.
As she finished, she rubbed her hand over Derek’s straining erection and squeezed. He hissed and pulled sharply on her nipples, which turned her on even more. Then she stood up and whirled around to face Alexander. Without a bra, her heavy breasts swung and jiggled, which he clearly appreciated.
“Like what you see?” she asked.
“Fuck, yeah.”
She prowled to his chair. His erection tented his briefs, and she made a swift change in her plans. Instead of kissing him bent over like with Derek, she straddled his lap but kept both feet on the ground.
Sheila lowered herself partially down without letting herself completely settle on his lap. They both groaned as her wet heat rubbed against his throbbing cock, and then she grazed her tits against his bare chest. She hopped up again.
“Oops. This is supposed to be a kiss.” She smirked and thrust her tongue in his mouth.
Their tongues dueled, and his hands caressed her breasts and played with her nipples. As the kiss grew hotter, Sheila gentled it and tore herself away.
When she returned to her chair, she preened at their expressions.
“Whew,” she said. “That’s thirsty work!”
She picked up her glass of water and quaffed half of it.
Alexander and Derek burst into laughter, and Derek drank some of his water, too.
Derek’s next question gave her ideas. “Have you ever used handcuffs or any kind of restraints?”
Alexander drank, but neither of the other two did. Sheila hoped she and Derek would have the chance to change that together.
Now it was Alexander’s turn again. It was impossible to concentrate, she was so excited about her next question, and she had to ask him to repeat himself.
“Have you ever masturbated in front of someone else?”
Sheila pinked.
“Yes,” she whispered. “Earlier tonight.”
She drank. So did both men.
Now’s the time. Be brave.
“Have you ever made out with more than one person at the same time?” she asked.
Nervously, she looked from one to the other. Neither took a drink, but their gazes set her skin on fire. The question in their eyes was clear.
“Part two of my question: would you like to?”
“What are you asking?” Derek growled. “What do you want to do?”
Her skin prickled at the sexy timbre of his voice, and she fought for courage. She wanted this. Badly.
“I want to know if you’d like to move this party to the couch. I’m not talking about a threesome,”—she blushed just saying the word—“but I would very much like to play. Does that… is that okay?”
Both men stood so quickly their chairs rocked.
Derek led her to the living room while Alexander moved the coffee table out of the way. The three of them squeezed onto the couch, Sheila sandwiched between them. Suddenly shy, she didn’t know what to say or do.
“I’m not sure how to start,” she confessed.
“Kiss me,” Derek ordered.
Relieved to have instruction, she did. Their mouths met in a soft kiss that reassured her. She had a lovely buzz from the alcohol which made her limbs somewhat heavy, but her mind was clear.
Sheila startled when Alexander moved behind her. He kissed and nibbled the back of her neck and shoulders. Goosebumps broke out along her body. Inexplicably, two men wanted to touch and kiss her at the same time.
After a few minutes of Derek’s kisses and caresses from Alexander, the latter tapped her shoulder. She turned to him, and he pressed his mouth to hers.
Alexander’s embrace was more heated than the one she shared with Derek. However, Derek didn’t limit himself to her neck and shoulders the way his friend had. He fondled her tits, twisting and pinching them while Alexander kissed her. He was also more talkative.
“Do you like this, baby?” Derek asked her. “You’re the focus of our attention, and there are so many different ways we can have fun tonight. I’ve wanted to touch you like this where you can be free and uninhibited for so long.”
Sheila whimpered as Derek made love to her with his hands and words.
After some time, he scooted so his back pressed into the couch. Then he plopped her on his lap, tearing her away from her kiss with Alexander. She wiggled to get comfortable as his erection poked into her, and he draped her legs over his spread hips.
While she still wore her soaked panties, her mind spun with the knowledge that she was otherwise naked, displayed, aroused, and open to their eager gazes.
“Fuck, that’s one sexy sight,” Alexander said.
“What do you have under here, I wonder?” Derek asked.
His fingers hovered mere centimeters from her aching pussy, but he didn’t touch her there.
“Hey, it’s still my turn. You took her away before I finished kissing her,” Alexander argued. “Hold her there.”
He tossed some pillows to the floor while Derek played more with her nipples. Sheila hissed when Alexander knelt at her feet and licked the inside of her left knee and then her right. He alternated kisses along both of her inner thighs until he reached her soaked, panty-covered pussy.
“May I?” he asked.
To her delight, his finger traced along the edge of her underwear.
“Yes,” she moaned.
She looked at him through slit eyes. As much as Sheila wanted to memorize everything, the sensations they aroused in her overwhelmed her.
She held her breath as Alexander pushed the gusset aside and licked the full length of her snatch. When he did it again repeatedly, she shuddered, even though he completely avoided her tumescent clit.
“Oh, she likes that,” Derek said. “Her nipples have drawn up so tight they could cut diamonds.”
Derek twisted those same nipples, and Sheila squirmed. He monitored Alexander’s actions while he fondled Sheila’s upper body. When he delicately traced his fingertips over her lips, Sheila sucked on.
“Not yet, babe. I already know I like your mouth on me. Right now, I’m still figuring out what makes you feel good.”
His hands whispered across her skin while they spoke, sending shivers along her spine.
“Everything you guys are doing makes me feel good,” she said on a breathy gasp.
“Even this?”
Derek trailed his fingertips from her breasts, along her breast plate to her collar. Her skin tingled everywhere he touched, and her heartbeat thundered in her ears. When his fingers slowly glided up her neck, she panted out her agreement.
Then Alexander finally sucked on her clit at the same time he slid a finger into her pussy. Derek wrapped his fingers around the column of her neck and squeezed. The combination of sensations and the sheer eroticism of the moment led to a screaming orgasm in short order.
“Oh my God, oh my God, I’m coming! I’m coming!” she screamed.
Derek twitched as she came, and his cock rubbed against her ass. She wiggled against him, and he choked her a little tighter.
“Did you like that, darlin’? You enjoyed having two men pleasure you at once. Don’t you? Are you ready to do it again? I’ve got so many ideas.”
“Let her have some water and a minute to calm down. We don’t want to chase her off,” Alexander scolded.