Strip Poker with Dares

Sat, 08/10/2013 - 20:45 -- aryaisthebest

In college I started playing poker. It was really popular at the time and was a fun thing to do in the middle of the week. We’d meet at a friends apartment and play for a few hours. Each person would put in $10, so it wasn’t like there was a lot to lose, but if by some chance I won it was a nice bit of money for the rest of the week. We played fairly regularly and I was very good, or very lucky if you hear it from the guys. One of the guys, lets call him Brad, would complain often that I was winning due to luck rather than skill. He would always get really mad when I beat him, which added to the enjoyment, since he was a bit of an ass.

After a few months of playing, Brad had had enough, and said that the only reason I was winning was because I was not afraid to lose and was taking risks. He would always tell us stories about playing poker in Vegas or online and how good he was. He always acted like he was the professional and we were just wannabes, which made beating him even more fun. Finally I teased him one too many times because he refused to play again unless we upped the odds. Brad and the others wanted to raise the buy in to $100, but I was completely broke and even spending $10 on the games was becoming too much. I complained and finally they relented but said there has to be a way to increase the risk. Then Brad suggested we try playing strip poker. Since I was winning a lot, I figured the odds were on my side. Besides, forcing Brad to strip naked was way better than taking his $10. Surprisingly, the other girls in the group agreed as well.

The way we set it up, each piece of clothes was worth a few chips. You only had to pay up and remove the clothes if you lost. This was good and bad. It allowed each person to bet a lot without having to strip. The problem was that it was easy to lose a lot and suddenly be forced to strip more than initially comfortable with.

Our first strip poker game started off great. We were 4 guys and 3 girls so I was confident that at the very least, I won’t be the first naked. I won the first few hands and was feeling very confident. Then I lost a few hands in a row and got some bad cards and suddenly I was sitting there in my bra, panties and a t-shirt while everyone else had more clothes than me. Suddenly the risk of being naked, or at least showing some skin was very real. I began playing a lot more carefully and, just like Brad predicted, things were not going well. My shirt came off immediately. I managed to come out ok in the next few hands, and one of the guys was down to his boxers while another girl was also down to her underwear when I lost big. I had some good cards, tried to take advantage of it and ended up losing everything. I had to stand up and strip naked in front of them.

Brad had the biggest shit-eating grin on his face as I got up and faced them. Everyone looked up and was waiting for me to strip naked. I remember feeling very self conscience as I first took my bra off, and then, while trying to keep my boobs covered with one hand, tried slipping my panties off. I pulled them down on one side and they stretched and caught on the other side, leaving my pussy bare while I desperately tried to pull them down as fast as possible. It just wasn’t working and I was flashing them my pussy for what seemed like forever, when with an exasperated sigh I uncovered my boobs and quickly pulled down my panties with both hands. I stepped out of them, threw them to the side and quickly sat back down, with both hands covering my boobs.

I wasn’t about to be the only one naked, so I said we should keep going. The guys readily agreed and the girls grudgingly agreed as well. The problem was that I was out of chips. I begged or some more and finally they said that I can have more chips if I agree to do dares. I reluctantly agreed, since I figured the dares would be things like showing them my body, which they had seen anyways.

I tried to cover myself up, but holding the cards with one hand and having to throw chips into the center of the table meant that I often had to uncover my breasts. Then I realized that I could use my nakedness as an advantage, since my boobs were distracting the guys. We ended up playing until everyone was naked and the worst dare I had to do was a few poses showing them my body, nothing too bad. One of the girls, Michelle, had to bend over and spread her butt cheeks, but that was the worst we did.

The next time we played, I was a lot less worried about being naked. I was the last one to get naked and I even got to dare Brad to do some naked jumping jacks. He was furious and said it was all luck. Because the risk of being naked was no longer enough to change my playing style, Brad demanded we start doing more serious dares. Our games started getting more serious and the dares raunchier and raunchier. The first line we crossed was when Brad asked me for a hand job. He always tried to humiliate me as much as possible to make me play more defensively. I agreed and ended up jerking him in front of everyone. The problem was that I didn’t know how to get him back. Asking him to finger me or eat me out in front of everyone seemed less of a punishment for him as for me. When I won big against him, I dared him to let me stick a finger in his ass. He was mad as hell, but we grabbed some vaseline and a glove and I shoved my finger in there. He was warm and tight and he became really hard. I teased him that he enjoyed it and he was really embarrassed. I remember that was a really great night.

Because the dares were getting raunchier and us girls had a hard time coming up with dares for the boys, we started bringing toys into the game. The guys were terrified that we would stick anything in their ass which evened the playing field, until our last game. Things quickly got heated up since we were all playing aggressively. Being naked was no longer a worry and we quickly got to doing dares. Another girl, Melissa, ended up owing a lot of money. We had quickly established that the more you lose in a hand, the worst the dare is. The guys obviously wanted to fuck us, so we made that limit really high. Over $100 in chips, which was hard to get since the whole table was maybe $500. Melissa unfortunately was doing really well, most of us had folded quickly and she ended up losing over $100 in one round. She was a bit of a plump girl, not fat, but could definitely stand to lose a few pounds. She lost to one of the guys, Randy, and, right before the last card, he told her that the dare was going to be sex. She responded that she was going to stick a vibrator up his ass. She ended up losing and I still remember the look on her face.

Randy just got up, took her hand and asked her how she wanted to do it. Still in shock, she didn’t really know what to say, so he helped her lie on her back on the couch and got on top of her. He was already hard as he slipped on a condom and he asked her if she needed lube. she just shook her head and he entered her, right in front of us. He started fucking her hard and I remember that everything on her was jiggling. The sound of his body slapping against hers is something I’ll never forget. At first she was in complete shock, with one hand trying to cover her boobs and the other her eyes, as he fucked away, but pretty soon she started moaning and before long she was screaming “oh god” while looking at us. She gripped the sides of the couch as he fucked her hard and she ended up having multiple orgasms. Each time she screamed loudly “oh my god I am cumming!”. That was the first time we had ever taken it that far.

Since she was out of money she just ended up lying on the couch naked for a while, trying to recover from her orgasms. Randy re-joined the table and we kept playing. Even though he had the most money, he ended up slowly losing it until finally it was only me and Brad. We were both naked and had over $200 each. We almost had the same amount and I got a great hand. I raised big and he matched me each time, until finally we both went all in. Along the way he tried to get me to fold, telling me of the dares he was going to do me as the pot got bigger and bigger. At first he was saying how he was going to make me masturbate in front of everyone, then how he was going to finger my ass. Then as we crossed the $100 limit he said he was going to fuck me doggy style and make me cum. When we crossed the $200 limit, he told me he was going to fuck me in the ass. I tried to remain calm, I had great cards and was sure he was bluffing. I was feeling high, and since we were drinking all night had a good buzz going, and felt that this was finally my chance to put him in his place. I countered and told him I was going to do embarrassing things to him, finally even threatening to fuck him in the ass with a strapon in front of everyone.

I had a flush, right from the start and was really confident. When it came time to show our cards, I slapped mine on the table. I yelled “I got you!” and jumped out of the chair and was jumping up and down at how I finally got him. I didn’t even care that I was naked and showing everyone my body. He just sat there, completely quiet, and slowly revealed his cards. He had a full house. Somewhere in the back of my mind it clicked that I had lost. I couldn’t believe it. I completely missed the possibility of him getting a full house. The worst part is that he got the full house only on the last card. I just stood there naked looking at the cards in shock as he got up and walked around to where I was. He grabbed my hips and pulled me back, then placed his hands on my thighs and got me to spread my legs. I still hadn’t quite registered what had happened when he spread my butt cheeks and started pushing his cock into my pussy.

I was already really wet and he was able to slip it right in. I didn’t even get a chance to say anything and he was already fucking me from behind. I just gripped the table as his body slapped against mine. I ended up leaning forward, my head and chest lying on the table as he fucked me from behind. He was fucking me hard, and I started hoping that maybe he won’t be able to last and will forget about the anal part, but right then he suddenly asked for lube. I don’t know who gave it to him, but he grabbed one of my butt cheeks, pulled it to the side and started pouring lube down my crack. Then, while his cock was still in my pussy, he started rubbing the lube into my ass pucker with his thumb, until he finally managed to push it in all the way. I couldn’t control myself and started moaning. He then pulled his thumb out of my butt with a wet pop, and at the same time slowly withdrew his penis from my pussy. I felt the tip of his penis against my butt. I couldn’t believe this was happening. I said “wait”, but he just started pushing his penis in. I let out a gasp as his cock went deeper and deeper. Each time he would pull out a bit, pour more lube, and then push it deeper until finally he was in all the way. I looked up and saw that everyone was standing around looking at me.Even Melissa had gotten up off the couch to watch.

Brad started fucking my ass, at first slowly, but then he picked up his pace. I couldn’t help but moan and started to feel an orgasm building. I managed to reach back with one hand and started playing with my pussy. By now Brad was fucking me like there was no tomorrow. I couldn’t help it and was yelling “oh god” at each thrust. I kept waiting for him to cum, but he was able to last no matter how fast he went. Finally I couldn’t hold the orgasm in anymore and I felt it explode inside of me. I yelled out that I was cumming. As the orgasm washed over me, Brad suddenly groaned and I felt him cumming and pumping his seed deep inside my ass. It was only then that I realized that he never bothered with a condom.

When he was done, Brad pulled out. I could feel his cum spilling out of my ass, over my pussy and down my legs. My legs were shaking and I could barely support myself. Randy and Michelle helped me get to the bathroom where I managed to clean myself up. Brad never let me live it down and I had to concede that he was the better player.The fact that he made me orgasm was worse than getting ass fucked in front of everyone. We played a few more times after that, but no one ever lost as badly again.

aryaisthebest's picture

Toward the end of my Sophomore year in college, I dated this guy for a bit. We were really into each other and it felt like things were getting serious quickly. Over the summer he invited me to go on vacation with his family. I want to share my experience here.