Cassy's Game

On our first night out, Cassy dressed herself in a short black lace cocktail dress and black Christian Louboutin heels. She looks great in black with her dark brunette hair and olive skin.

"Are you sure you want to do this?" Cassy said nervously as we were about to head to the bar.

"Absolutely," I said. "This will be the only night where either of us can stop it. Let's have fun."

"I'm scared," she said.

"Don't be," I reassured her. "I'll be close by. I'll always be there to protect you."

When we got off the elevator, I kissed Cassy's cheek and told her not to lose. I had her walk ahead of me so she could enter the bar alone. Watching the door close behind her reminded me of the finality of what we were about to do.

I entered the door a minute later and made my way to the main bar area. Cassy was seated at one of the stools and was looking around nervously. We made brief eye contact as I took a seat at a table close by. I ordered a glass of whiskey to calm my nerves. My hands were shaking, I was so nervous.

Cassy's nerves were also taking their toll on her. She felt a huge knot in her stomach as she sat at the bar wondering who it would be. Would it be someone she was attracted to? Would he be creepy? Would she disappoint me if she ended it too soon?

Not long after, a man approached her and asked if he could sit down. She nodded, nervously. He was about six feet tall with graying hair. He looked like he was in his late forties or early fifties. He was dressed nice and had what looked like a Bulgari watch on his wrist. He seemed like one of those guys who was trying to look like a high roller. He had a completely average build and was average in the looks department as well.

I watched as they talked for a few minutes. He ordered drinks with the bartender. A few minutes later, he returned with a glass of champagne for my wife and a beer for him. Cassy was playing the game well so far.

Cassy sipped her champagne as they talked. She was sitting at the barstool with her toned legs facing him. Her cleavage was spilling out of the lacie top. I could see his eyes drift over my wife's body. She smiled up at him, and it was apparent that whatever he was saying to her was not bothering her or making her feel uncomfortable.

The man leaned in close to her and said something in her ear. As he sat back up, he placed his hand over hers on the bar. She did not pull it back, and she turned to look at me briefly. His hand rubbed her hand affectionately as they talked. I took a drag of my whiskey as my pants tightened.

Their conversation continued, and they ordered another round of drinks. I was nursing my second whiskey as I watched my wife being seduced by another man. I was so used to being in control. I learned at a young age how to take control of situations, and I never looked back. I always tried to maintain a sense of order around my life. Doing this was in direct opposition to everything I'd ever known, and it was driving me insane.

I questioned my decision as I watched his hand on my wife's while she laughed at his words. How far would she go? How far would I let it go? Who would win the game? What made me want to do this? All of these questions boiled to the surface as his other hand reached down and landed on her bare leg just above her knee.

The older man left his hand there, and when she did not pull away I could see a flush to her skin and could tell she was either nervous or getting turned on. I had a feeling it was the latter. She looked at me briefly, and she had to have noticed the hungry look in her eyes. She knew I liked what was happening, and it pushed her forward.

His hands began moving on her leg, slowly caressing her as they talked. His fingers danced across her skin. Slowly, the older man moved his hand up my wife's smooth thigh. She smiled at him without batting an eye as he moved his fingertips in small circles on her skin.

After a few minutes of conversation, Cassy slid off her barstool, and walked toward me, but turned and walked toward the restrooms. For a brief second, I thought she was ending the game. A few moments later, my phone rang with her on the line.

"I'm going to leave my phone on speaker so you can hear our conversation," she told me. "Put your phone on mute when you hear me leave."

"Okay, how are you?" I asked, concerned.

"Soaking wet," she said. "I'm going back to Tim now. I hope you are enjoying this as much as I am."

I put my phone on mute as she returned to the bar. We made eye contact briefly and her lips curled up in a sexy smile. My wife had an extra sway in her hips as she approached Tim at the bar. His eyes devoured her as she returned to her seat.

"I'm sure you hear this all the time, but you are the most beautiful woman I've ever met, Cassy," Tim said as he leaned down and kissed her cheek.

"Awe, that's sweet of you to say," Cassy smiled as she sat down again, playing her phone on the counter between them face down.

"I mean it," Tim continued. "You have a great body and the most electrifying eyes I've ever seen. Your husband is a lucky man."

"Thank you again," Cassy smiled. "You're really sweet."

Tim placed his hand back on my wife's thigh as they continued their conversation. He was really pouring on the charm. He claimed to be an attorney from L.A., who was in Vegas on business. He continued pouring on the compliments. He slid his hand higher and higher up her thigh until it reached the bottom hem of her dress. He again moved his fingers in small circles across her skin.

"I know this is presumptuous of me, but I thought I'd ask," Tim said, making time slow down. I knew what was coming, and I wondered how she would respond. I could see her eyes widen as she knew what he was about to ask. "Would you like to come up to my room, Cassy?"

"I, I, I can't," Cassy replied hesitantly. "I really need to get to bed. I have a conference in the morning. I really should be going."

"I understand," he replied disappointedly. "If you change your mind, I'm in room 1520."

"Thank you for talking to me tonight, and thanks for the drinks," Cassy said as she started to stand.

"Can I get a kiss before you go?" Tim said.

She'd already lost the game, and she didn't need to say yes. She stood there and looked up at him with her big blue eyes, looking vulnerable. They slowly closed the distance between each other until their lips met in a soft kiss. Ted's hands reached behind my wife's back and pulled her into him, and he kissed her again much harder this time. She kissed him back as their bodies pressed together in front of the bar. After several seconds of making out, they finally separated. Cassy was breathing hard while looking up at him with glazed eyes.

"I really need to get going," Cassy said breathlessly. "Thank you for everything."

"1520 if you change your mind," Tim told her again. "And thank you, Cassy. You made my week."

I met Cassy in the hallway outside of the bar. Her hands were shaking and she was visibly flushed. Her body was on fire. When we entered the elevator, I attacked her instantly, kissing her wildly as our passion took over both of us. Knowing her lips and tongue were just on another man made me crazy with desire for her.

That night, we had the best sex of our life up until then. Cassy told me everything that was said leading up to her turning her phone on. She'd told Tim we were in an open relationship. He didn't seem to mind and continued his advances.

Our test run of the game worked surprisingly well. We played the game a few more times while at least an hour from our home. We took turns winning and losing and never went further than heavy petting and kissing. We liked to go to urban jazz bars the most. We seemed to have the most success at those places. I loved watching men trying to lure her into their beds. I wondered when one would succeed.

On New Years, we went to a jazz bar in LA that was supposed to be one of the best. Cassy lost the last time we played the game, and she was not allowed to say no tonight. She was wearing another black cocktail dress with sparkling silver sequins above her left leg in the shape of flowers. The dress had a single strap over her right shoulder. Her black heels had matching silver sequins, and her toes were freshly pedicured. Her dark long hair was held up sexily on her head, leaving her slender neck and shoulders bare. Her makeup highlighted her long eyelashes and her thick pink lips. She looked as sexy as I'd ever seen her. We were staying at a hotel close to the bar, and did not need to drive.

Again, Cassy entered the bar a minute before I did. The inside of the bar had lots of seating and deep booths around the edges. Cassy took a seat at the main bar, and I sat off to the side.

Cassy's nerves were getting to her as she wondered who it would be this time. Not knowing who was going to approach her made it that much more exciting. Her hands shook with anticipation.

A few minutes after sitting down, a large Polynesian man sat next to Cassy and started talking to her as she sipped her martini. He appeared to be in his mid fifties, but he seemed like he took good care of himself physically. He looked like an older version of The Rock with less steroids. They chatted for several minutes as the jazz band played in the background.

I couldn't hear what they were saying, but I could tell Cassy was attracted to him by the way she was laughing at his jokes and touching his arm.

At one point, I saw him touch her diamond wedding ring as he said something to her. She said something to him and then pointed over at me. He turned and smiled, lifting his hands and waving me over to him. Shit, gig is up, I thought to myself. The huge man towered over me as he stood to shake my hand, introducing himself.

"Hi, my name's Jason," he said as his hand enveloped mine.

"I'm Bobby," I said nervously. I hadn't been caught by anyone playing the game up until now.

"Your young wife tells me you two are playing a game?" He said grinning. "Tell me more."

I gave him a brief rundown of what we'd been doing, and I even told him that Cassy was not allowed to say no tonight.

"Interesting," Jason said as he scratched his chin, thinking."So if I tell her to go to the restroom and take her panties off, she can't say no?"

"That's the rule," I smiled. I liked his way of thinking.

"First I want to see them, Cassy," Jason said. "Pull up your dress so I can see them on your hot little body."

I could see fear in her eyes as she looked around the bar apprehensively. She turned her barstool so her legs were facing him, but no one else close by could see and parted her legs until her black lace panties became visible. I could easily see her moist slit through her panties, and so could Jason. She was biting her lower lip and breathing rapidly.

"Beautiful," Jason said as he looked down at her exposure. "Now go take them off and bring them back to me."

Cassy closed her legs, spun on her stool, and stood to go to the restroom. She had a sexy nervous grin on her face as walked past me.

"Your wife is a firecracker, Bobby," Jason smiled as we watched her walk away.

"I know," I agreed.

"How far are you willing to take her?" He asked candidly.

"She hasn't done anything more than some petting over clothing and makeout sessions," I said. "It's a new year though. Maybe we can start 2022 with something a bit better."

"I'll see what I can do," Jason said, smiling.

Cassy returned from the restroom a short time later. She made eye contact with Jason as she returned to the bar. The look on her face was provocative as she gazed into his hungry eyes. She swayed her hips seductively as she walked. She was playing her game well, trying not to look as nervous as she actually was inside. She handed her balled up panties to him, hoping he wouldn't open them in front of the bar. She brought them up to his nose and sniffed them before putting them into his pocket.

"You even smell beautiful, Cassy," Jason said.

"Thank you," Cassy replied, unsure how to respond.

"I own this bar, Cassy," Jason said. "Would you and your husband like to take a tour?"

"Sure," she replied, unable to say no.

We walked to the back of the bar, and he opened a door leading to an office and what looked like a cigar lounge. No one was inside at this time. There was a one-way glass window overlooking the club from the lounge. There were comfortable leather couches and chairs, along with signed memorabilia from famous musicians adorning the walls.

"Have a seat, Cassy," Jason said, patting the couch beside him. "Make yourself comfortable."

She sat next to him, looking nervously at me, before looking back at Jason, who wrapped his big arm around her. She looked nervous and afraid, but did not seem to mind the attention Jason was providing her. I was not going to stop them.

"Will you kiss me, Cassy?" Jason asked her.

She nodded and looked up at him expectantly with her big blue eyes. He moved his lips to hers and kissed her deeply. I was sitting in the chair across from them as the huge man kissed her lips and sucked her tongue into his mouth. I could hear their lips smacking and their tongues exploring each other. Across a bar is one thing. This was intimate.

Jason's hands moved up my wife's thigh as they made out in front of me. His huge hand made its way under her short dress with no barrier between him and her moist folds. Her body tensed, and she moaned into their kiss as his fingers made contact with her pussy. This was the first time another man touched Cassy there. Cassy spread her legs, giving him more access with his hand as they kissed wildly on the leather couch. I could see his big finger pushing into her very moist folds. Her bald pussy was taking another man's finger for the very first time.

Jason stopped kissing her suddenly as he looked into her eyes saying, "Take your dress off, Cassy. Stand in front of me, and do it slowly."

My wife gasped as realization hit her where this was going. She looked at me, wondering if I was going to stop it. If this was going to be enough. When she saw the hungry look in my eyes, she realized I was not stopping them. She slowly stood and turned toward Jason.

My trembling wife reached down to the hem of her dress, raising it slowly up her body. More and more of her creamy thighs were revealed as she lifted the dress until I could see the bottom of her round ass. Jason was treated with her very bald pussy as she lifted it up her skin. Cassy peeled the dress up and off her and dropped it on the couch, leaving her in just heels and a bra.

Jason held out his hand saying, "The bra too."

Cassy reached behind her and unlatched the back of her bra and pulled it off her arms, revealing her entire nude body to Jason's hungry eyes. She handed Jason her bra, and he tossed it on top of her dress as he reached out and pulled her down on top of him.

I watched my nude wife straddle another man's body as they kissed deeply in front of me. He had uninhibited access to her body as they made out, and he was making the best of it. His hands slid up to her perfect breasts and pinched her pink nipples, making her moan loudly. Jason slid his other hand down to her round ass cheeks and caressed them as she ground on the huge bulge in his pants. Her body was catching fire.

Jason flipped her over on her back and spread her legs widely. Her pretty pink pussy was soaked. Jason wasted no time and dug into her with his tongue, making her groan loudly. He licked her wildly as savored the taste of her. His huge hands were under her knees pushing her legs up and back, spreading her lewdly as he feasted on her pink folds. Her high heels pointed up toward the ceiling.

"Tell your husband what I'm doing to you," Jason said huskily. "Tell him how I'm making you feel."

"Oh God, Bobby, he's eating me so good," Cassy gasped. "I don't think I'm gonna last long. I'm gonna cum all over another man's tongue. Ohhh fuuck!

Cassy's body was trembling in ecstasy as Jason feasted on her in front of me. My cock was throbbing in my pants, and I did not know how much more I could watch before I'd burst. She was moaning in ways I'd never heard before.

Cassy looked into Jason's eyes as he licked her most intimate parts. He was making her feel a way only her husband should. She was conflicted with emotion as something so wrong felt so overwhelmingly good. She was submitting herself completely to another man as I watched her. She looked into my eyes as she let the pleasure course through her body.

"Oh Bobby, he's making me cum. I'm gonna cum. Uhhh! Oh fuck!" she cried as her body climaxed on Jason's tongue, spurting fluids all over the couch below her.

Cassy's body writhed in pleasure as her body released months of tension. We'd been playing the game for over six months and never made it this far. All the teasing and talking had led to this moment, and she released all of her carnal passion into the man who was giving her pleasure. A man who was not her husband. She held the back of his head as he continued to lick her through her orgasm.

Jason held her still as she came down from her orgasm. He let go of her legs, and she fell back on the couch, sighing. He stood and looked down at my satiated wife, admiring her still trembling nude body.

"Cassy, will you suck my cock?" Jason asked, knowing she couldn't say no. "Tell me." She looked at me again to see if I was going to stop her, ending the game. All she saw was wanton desire in my eyes.

"I want to suck your big cock, Jason," Cassy said sexily.

"How do you know it's big?" he asked teasingly.

"I could feel it earlier, when I was sitting on you," she admitted.

"Take it out and see for yourself," Jason told her.

Cassy sat up on the couch and leaned forward to unbutton his pants. She slid off the couch and kneeled in front of him. As she unzipped his fly. She pulled down on his waistband until the base of his thick cock came into view. She gasped as she saw it. She pulled more exposing his long shaft to her wide eyes. This was the second cock she'd ever seen in person, and it was a lot bigger than mine. She pulled his pants to his knees, freeing his large brown cock to her feasting eyes.

"Tell me and your husband what you think," Jason said.

"Baby, I'm touching another man's big cock," she said as she reached up to grasp his thick nine inch dick with her left hand.

"What are you gonna do with it?" Jason asked. "Tell us."

"I'm gonna make it feel good for him, baby," Cassy said admiringly. "I'm gonna make him cum."

She couldn't get her fingers around it as her wedding ring sparkled in the light. Her small white hand contrasted against his huge brown cock. She squeezed and stroked him as she admired his firmness and size. A dollop of precum dripped from the tip. She leaned forward and opened her mouth with a hungry look in her eyes. Her tongue reached out between her parted lips and licked the precum off his cockhead, making her moan as she tasted him.

She opened her mouth and pushed the crown of his cock between her pink lips. She had to open wide to get it inside. She slowly worked him as she licked around his crown and shaft as more and more of his cock entered her mouth. His cock touched her tonsils, but she did not gag. She'd practiced on her big dildo at home and learned to suppress that impulse.

I watched as my nude wife took more and more of Jason's cock into her mouth and throat. She now had half of his thick cock in her mouth, and she was trying to get more in. She was fondling his huge hanging balls with her small hands as she did everything she could to please the man in front of her.

"Damn, Bobby, your wife can suck dick!" Jason said as he pulled her face into him even more, making her moan in front of both of us. "And I think this is turning her on. Maybe I should eat her sweet pussy again."