My buddy Jason has always had a bit of an obsessive streak about him. Nothing too odd, you understand, just a bit more obsessive than the regular guy. Take poker, for example. Once Jason decided he wanted to learn to play poker well, he studied every book he could find, learned every technique that he thought reasonable, and practiced as often as he could. He started out with blackjack, and could soon accurately card count a six-deck shoe. More often than not, he could play blackjack for hours at a time, generally coming out ahead. He didn't particularly like to gamble, he just liked to play.
Then he discovered Texas Hold 'Em. The old obsessive behavior came back, and he studied and practiced and played and played and played. He began to host tournaments at his house on a regular basis, and hosted an eight to ten person game almost every weekend. He taught me to play, although I never was very good, but we enjoyed many hours matching wits and skills. His wife, Jenny, played almost as often as Jason did, and became fairly skilled in her own right, although she was never as obsessive as Jason.
The best game I ever played happened early into the Texas Hold 'Em obsession. I had stopped in one evening to shoot the breeze and drink his beer, and Jason and Jennifer suggested we play poker. We broke out the chips and cards and played for a while, just to knock the rust off. After a couple games and several beers, our chat had turned rather blue, with Jenny holding up her end of the innuendos quite ably. I always suspected that she had a bit of wild streak in her, but I never knew exactly how wild.
Somehow, our discussion turned to strip poker, and the wild claims people we had known had made about games they had played. At one point, Jenny said, with an off-hand tone, that we should play strip Texas Hold 'Em. I looked at Jason, as I didn't want to appear to lust after his wife, even though I did. She was a petite thing, very pretty with long curly hair, not quite five foot, a slender, willowy blond with perky A-cup tits and a sweet curvy ass. Jason was looking at Jenny, trying to determine if she serious. He said to her, "I'm game if you are." They both then looked at me.
"What the heck," I said. "Should be interesting." I leered at Jenny and she giggled, then I winked at Jason. He smiled back and we started talking about how to structure the game. We agreed that we would start out with a set amount of chips. The game would be played normally, expect that in the event that there was a showdown between two or more players, the loser of the showdown would also lose a piece of clothing. If you mucked your cards, there was no penalty, but if you went into a showdown, you might come out short more than just chips. Also, we decided that you could make unlimited rebuys of the initial chip count. The cost would be one piece of clothing, and you could not use your last piece of clothing for the rebuy. If you were out of chips and chose not to rebuy or couldn't rebuy, you lost and had to strip down. Clothing could not be rebought. First person naked would be the loser, and would have to stay naked to deal the rest of the game and serve drinks and snacks to the remaining players, while they played the rest of game out. We began cautiously, with most of the hands being folded early. The first showdown was between Jason and Jenny, and Jason came out on top. Jenny reached down, took off a shoe, and tossed it off to the side.
The game went on, with all of us shedding shoes and socks as play continued. It became pretty apparent that Jenny and I were fairly evenly matched, while Jason was far superior. Jenny had a slight advantage in that she was wearing a bra, which gave her one extra piece of clothing. I made up for that when we went head-to-head. We both had our shirt, shorts and underwear on, but she was on a short stack when I pushed her to go all in. I took the pot with a pocket pair and a pair on the board against her Big Slick. She was now faced with an unenviable choice. She lost her top with the hand, and was now out of chips. She decided to toss her shorts off as well so that she could get a rebuy and stay in the game.
Seeing her strip off her shirt and shorts gave me an instant throbbing erection. She was wearing a sweet lacy push-up demi-bra with matching thong panties in a deep red, almost ruby color. The underwear color set off her creamy skin perfectly, and she posed there for a second, doing a slow pirouette, letting us admire her shapely ass before she took her seat again to resume the game.
Jason kept winning, depleting our stacks and taking me down to my underwear. Jenny managed to hang on to her bra and panties for a while, but shortly after I lost my shorts, Jenny lost a showdown to Jason and had to give up her bra. She sat back and pushed her softly curled hair off her shoulders. She slowly reached up between her breasts and undid the clasp between the bra cups. Jenny slipped the bra off while managing to keep one arm over her tits until the bra had fallen off the other arm and onto the floor. She then slowly dropped her arm, exposing her perky tits with their small, hard nipples to my avid gaze. Jason stared as well, seeming to enjoy both the interest I showed in his wife's tits and her excitement in exposing them to us.
After catching our breath, play resumed. Since Jenny and I were both down to our underwear pants, as well as having short stacks, it became a hard-fought match between us not to lose. It came down to one last hand, with both of us all in. I had a low pair, while Jenny had unsuited connectors. The flop came down with Jenny getting two more connectors for a possible straight, with nothing for me. The turn gave Jenny a pair, which was higher than mine, and I began to steel myself to being the naked guy serving drinks and dealing the remaining hands. The river card came down, and I stared at the card matching my pair and giving me trips to beat Jenny's pair.
Jenny and Jason both stared at the card, and then looked up at each other. I began to say that Jenny didn't have to strip off, trying to play the gentleman, but Jason stopped me, saying "A bet's a bet and a deal is a deal. Jenny, you agreed to this, so drop those drawers and bring us drinks."
Jenny sat there a minute, then stood up, looking between us while she gathered her courage. Finally, as we both watched, she stood, slid her hands under the sides of the thong and slid the garment down her shapely thighs, then kicked the scrap of lace onto the pile of clothes. Jenny stood there, blushing while Jason and I stared and drooled. Jenny kept her pubic hair neatly trimmed in a small triangle above her lips, which were slightly puffy and coral-colored, betraying her excitement from being on display. She turned slowly away from us, bending from the waist to pick up her shoes to move them to the entryway. By bending over that way, she gave us a beaver shot of epic proportions as well as a good look at her nether eye. She held the pose for a few seconds longer than she needed to and then sashayed to the entryway, taking the shoes with her. "Damn," I breathed, swallowing hard and tearing my gaze away from Jenny's sweetly swaying ass. Jason said, "Yeah. Damn. That's quite a performance. I don't think I knew what I was getting into."
"Lucky you," I said as I smiled.
"I'm guessing she's going to be incredibly horny tonight," Jason said as he smiled back.
"Do you want me to take off so you can get to ... ah ... other activities?"
Jenny interrupted as she came back, two beers in her hands and a mock frown on her face, "Don't even think about it! The deal was that you two now have to play this out, so sit down while I deal. I'm not going to be the only one naked here!"
So, we sat down and went back to the game. It was clear that it was only a matter of time before Jason finished me off. Jenny didn't help, either. As she dealt, she kept pushing her tits together with her arms, disrupting my concentration and making it more difficult to focus on the game. She began to be more brazen, rubbing her nipples, or pinching them and moaning while we bet and drawing our attention to her chest rather than our cards. At one point, she reached her hand down under the table, closed her eyes and moved her hand around while she moaned. I couldn't see what she was doing, but it was clear that she was masturbating, running her finger through her slit while rocking gently back and forth. As we watched, she brought her hand out from under the table and sniffing it, then running her finger along Jason's upper lip.
Jason closed his eyes and breathed deeply. Jenny smirked, got up and went to the kitchen to get herself a drink. As she did, she walked by me, and I could see the wetness in her matted hair and I could easily smell her excitement. The scent was intoxicating. By now, my hard-on was almost painful and the pre-cum had soaked through the fabric of my boxers. By the way Jason shifted uncomfortably in his chair, I would have bet he was in the same condition.
It wasn't long after Jenny came back to the table that the game ended. As was perfectly obvious over the last several hands, I was short stacked and had to go all in to try to get back in the game. Jason decided that it was time put an end to the game and pushed me all in. His 7 and 9 offsuit turned into a full house on the table and it was my turn to do the strip-tease.
Jason began whistling the Deliverance theme. Jenny, picking up the cue, said, "Them panties. Take 'em off. Just take 'em right off." I laughed when Jenny, doing a bad hillbilly accent, said, "Just drop 'em, boy!" I pulled the waistband out over my dick and dropped the shorts to the floor. Jenny gave a little wolf-whistle while Jason pointed and laughed. While I knew he was just ribbing me, I also knew that I was just average in the endowment department, while some of Jason's previous girlfriends had intimated that Jason was...impressive. I sat back down, laughing nervously.
"So, what do we do now?" Jason asked. He began to collect the cards and chips and put them away. Jenny, with a mischievous grin, said, "Don't you think it's a bit rude that you're the only one wearing clothes? I think you should make our guest feel at home by joining the skin party!" I had no great need to see Jason naked, but it seemed like Jenny was going somewhere with this and I wanted to see how far she was willing to go. I said, "It's ok, Jenny. Jason's never been known for his interpersonal skills." Jenny winked at me, and when Jason's back was turned to put the chips away, she reached over and without warning, stripped Jason's shorts and underwear down.
While Jason spluttered and tried to grab for his shorts, Jenny giggled and said, "Now we're all even!" Jenny turned and put her foot on Jason's shorts so that he was unable to pull them up. When he tried to take a step back, he stepped right out of the shorts and was left standing there, naked. A quick look told me that his past girlfriends were right. He was ... impressive, and quite erect. He said, "Now how is this fair? I won the game. You lost. If anything, you should be doing something to reward me for winning."
"Well, I did have that in mind for later, but if you don't want to wait..." She spocked an eyebrow at him with a quick glance toward me. Now that sounded like a setup to me, so I decided to take a swing at it. "Oh, don't let me stop you. I'll just sit in the corner and watch. Go ahead and do what you do."
Jenny turned to look at me. "You just want to watch?"
"Well, since we seem to be missing an unattached female, playing along doesn't seem to be in the cards, and I can't imagine any straight guy would object to watching a beautiful woman make love. So, yeah, I want to watch. I hope you won't mind if I ...um... entertain myself while I watch."
Jenny looked at Jason and them moved toward me. Without hesitating she reached out and grabbed my dick and began to stroke. "I don't think you'll need to go to that extreme."
I was shocked. I couldn't move. I looked over at Jason while his wife continued to stroke me. He smiled and said, "Jenny has always been a little adventurous. We made a deal shortly after we got married. We would each be able to invite someone to join us, but only if we both agreed and both of us were present. Jenny enjoys threeways with both boys and girls, and I enjoy Jenny. It seems to work."
Jenny looked at me without stopping her efforts and said, "You've been on the list for a while, but the opportunity never presented itself. This seems like a good time." She reached her other hand behind my head and pulled me into a deep kiss. Our lips met with a quick electric shock and then our tongues began exploring. As we kissed, I heard Jason move toward us and felt him slip his hands around Jenny's waist and up onto her tits. He began nibbling the back of her neck while we continued kissing.
After a few minutes, she turned to face Jason and began to kiss him, while I ran my hands up her flanks and closed them over her perky tits. As I did so, I took her small, prominent nipples between my fingers and twisted and pinched them, drawing moans from deep in her throat. At the same time, I used my dick and rubbed the head up and down between the cheeks of her butt. Meanwhile, I could tell that Jason had reached his hand down to stroke her pussy. She was squirming and moaning continuously, and we were all getting pretty worked up.
Jenny disengaged from Jason, turned so that she could put her arms around us and led us over to the couch. She directed us to sit down and knelt in front of us, taking a cock in each hand. She stroked us, and then began licking the head of each cock, starting with Jason's and then moving to mine. She spent a few minutes on each before shifting to the other one. After a while, she sat back on her heels, still stroking gently, and said, "OK, who wants to eat me?"
Jason and I both chorused 'me' and Jenny told Jason to lay on the floor. She knelt between his legs, bending over to take his cock in her mouth. Just before he did, she looked over at me and said, "What are you waiting for? It ain't eating itself!" I didn't need any more encouragement. I slid off the couch and knelt behind Jenny, resting my hands on the curves of her ass. I bent my head to her and began to lick and nibble the cheeks of her ass, working my way down to her thighs and circling her ass and cunt with licks and kisses. I focused first on her puckered ass and licked around it lightly before stiffening my tongue and plunging it into her hole. She squirmed and pushed back toward my face, which I took as a sign she was enjoying the attention I was paying to her butt, and continued in the same vein for a few minutes.
I then began running my tongue down along her slit, gathering the sweet nectar I found there until I reached her clit, peeking out out from its hood like a pearl. I stroked the little bud with my tongue, drawing a moan and a quiver from the otherwise-occupied Jenny. I kept playing with her pussy lips and clit, drawing them into my mouth before letting them slip out again. Then I would plunge my tongue into her pussy before returning to her clit.
By this time, my ministrations had worked her up to a frenzy of actions as she made circles with her hips while continuing to thrust them back at me. As the same time, she frantically bobbing up and down on Jason's cock until with a loud moan, he erupted into her mouth. Once she had finished cleaning him off with her lips and tongue, she spun around and pushed me to the floor. Almost at once, she buried my cock in her mouth, taking me all the way down her throat. She began to withdraw from my dick, then slowly licked around the head and taking me back in her mouth again. She kept up this motion, occasionally burying her nose in my public hair. While she was doing that, Jason had moved into position behind her and started licking his wife's gorgeous pussy. Much as she had done when I was eating her, she moaned and fidgeted in time with Jason's ministrations. In the meantime, she was expressing her pleasure in the way she was sucking my cock and I was getting close to filling her mouth.
I told her so, and she just continued to suck my dick, adding a stroking motion with her hand. I tensed up, the pleasure sending me over the edge, and I came in great spurting gobs. Jenny took it all, slowing down and looking up at me with a smile while Jason brought her off. As she orgasmed, she collapsed on my leg, shuddering with the aftershocks of her pleasure.
We all lay there, spent. I was laying up against the couch. Jenny was face down, her head pillowed on my thigh. Jason lay on his side, his head resting on the shapely cheek of Jenny's ass. Jenny stirred first, getting up and moving toward the bathroom. Her beautiful ass swayed sensuously as she walked away from us. She called back over her shoulder, "I'll be right back."
Jason sat up and leaned against the couch a few feet away from me. We looked over at each other and smiled. I took a breath and said, "Wow...Just, wow." Jason nodded his head in agreement and we sat there in companionable silence.
Jenny came back, looking radiant and carrying a towel. The towel looked like it was wrapped around something small, but I couldn't tell what it was. She sat down between us, putting the towel on her lap, and sat back against the couch. She looked from Jason to me and back to Jason again, a small smile playing across her lips. "I have a request. I know Jason won, and I have to do what he says, so I thought I would make a suggestion for Jason to ask."
Neither of us interrupted her. I was thinking that whatever she wanted to do was sure to be interesting and a lot of fun. As long as Jason agreed, I didn't see that anything she could suggest could be bad. Jenny continued, "Actually, Brian gave me the idea when he was giving me a rim job earlier. I want to get stuffed."
I had no idea what the heck she was talking about. Jason looked at me and said to Jenny, "How do you want it?" Obviously, he knew what she was talking about and didn't seem to have an objection.
"I thought Brian should have the honors, if that's alright with you," Jenny said.
"Sounds good. Do you have everything you need?"
Jenny nodded and pointed to the towel. I said, "Anybody feel like filling me in?"
Jenny smiled coquettishly, reached out and took my cock in her hand while reaching for Jason's cock with her other. As she stroked us, she said, "I've always wanted to get stuffed, but never had the opportunity. Given my size and Jason's ... endowment, it was never an option. Not that you're a midget, mind you, but you I could tell when I deep-throated you that you would do fine."
"Get me stuffed. It's taking two guys at the same time, one up front and one back there. Jason and I have tried anal a couple time, but I've never been able to take him back there. I'm hoping that I'll have better luck with you. As a bonus, I get to enjoy Jason at the same time!" Jenny was fairly beaming as she finished her description.
"Don't you think it will hurt?" I didn't want to hurt her, but the idea she described excited me, as she could readily tell.
"No, I don't think so. I've used some toys back there before, so I'm not worried about that. You'll just need to use a fair amount of lube to make sure things go ... smoothly." With that, she unwrapped the towel to display a tube of KY, which she then handed to me. Jenny then began issuing instructions. "Jason, you lay on the floor there, and I'll get on top. Once we get set, you get behind me and put it in."
I nodded and opened the lube. Meanwhile, Jenny had mounted Jason and was positioning his massive organ at the entrance to her slit. I watch while his monster member spread her lips open as she slowly lowered herself down, rocking back and forth to get him fully seated within her. When she was, she bent forward so that her ass was fully exposed with her cheeks spread wide. She looked back over her shoulder and said huskily, "Go ahead and put it in."