I have had only two experiences with strip poker, and I lost both times, but it was not all bad.
The first time happened when my brother was staying with me, and a couple of his friends stopped by to wait for him to get home from work. He worked a swing shift, so they had a few hours before he would be home. These friends were a guy and a girl. The guy was hoping to get lucky, hence her company. Somehow—and I don’t remember how—, the topic turned to cards and then, naturally enough, to strip poker. I don’t play cards at all, but when she agreed, I figured, what the hell. Whoever won got whatever they wanted.
She was a petite natural blonde and a single mother taking a night for herself. She wasn’t particularly attractive, but she wasn’t ugly either—maybe a 5. Most importantly was that she was present. Without all of the boring details, I have to admit that I was naked in no time flat, so I mostly watched the rest of the game from the sideline. She was pretty good. She was down do her bra and panties, and he was down to is BVDs and a shirt. She lost the next hand. I found it interesting that she chose to remove her panties instead of her bra. Did I mention she was a natural blonde? Yep. The carpet matched the drapes. He lost the next two hands, and she won.
Her anything she wanted was to get a baby oil massage by both of us. She unleashed her A cups—I might be overstating her cup size—and got on the carpet. I have to say I enjoyed rubbing her down—and our hands strayed quite a bit along the way. We kept this up for about half an hour or less when she decided she wanted to take a bath to rinse off the oil. The catch was she only invited me. Her friend was less than elated.
We took a bath and made the further decision to go into my room. Her friend was even less thrilled. She was probably 5′ even and thin. She had a nice untrimmed blonde bush and the kind of pussy where her labia minora protrude significantly past her labia majora—roast beef, I believe is the vernacular. I had never before and never since been with a woman with a pussy like this, but I have seen pictures—on some other guy’s computer, I swear. Her breasts were not only small, they were like deflated balloons. I felt bad for her. No wonder she wanted to take off her panties before her bra, but she was naked and in my bed, so what was I to do?
She resisted my going down on her and just wanted me to fuck her. I tried to get her to help me get started by sucking my cock, but she didn’t want any part of that either. When I stuck my cock into her pussy, it was so loose. I have only ever fucked two women who were so loose, and she was the first. If it wasn’t for all of the excess of folds of her pussy lips, I am not sure there would have been enough friction for me to cum, but I did. I know loose pussies do not come from fucking too much. I have been with enough women to know that. It must be genetic. I never saw her again.
The next time I played strip poker, I was the loser. No, I didn’t play, but this time it was my girlfriend who wanted to play with three other guys we met at a club. She was the only female but fancied herself a skilled player. She wasn’t. As I recall, she lost pretty much every hand from the get go. Even so, she thought she could win—or just wanted to lose. When she was stark naked, she wanted to play a last hand. If she lost, she would give the winner a blowjob while everybody else could watch. I can’t say I wasn’t pissed at the prospect of having my girlfriend suck off some stranger we had just met at a club. Well, sure enough she lost, and somebody did end up winning.
When it came time to paying off her debt, I wasn’t interested in watching. I left the room, and she came out in a few minutes with some snickering guys saying nothing happened. I guess it was comeuppance for my previous game. No more strip poker for me.