I was the most straight laced kid ever. All through high school I didn't drink, rarely dated, got straight A's, and read books just for fun. I was a total prude too, which is partly why I rarely dated. Then I went to college at a small liberal arts school, discovered that I enjoyed wine and could tolerate beer, and totally came out of my shell. Most of the people who knew me had no idea about my transformation and frankly I kept it pretty much to myself. But after a few drinks, I would sometimes get a little crazy.
About a year after I graduated, I was hanging out with my older sister and her fiancé at their apartment. They were getting married in a few weeks and I was helping my sister with some last minute details including her final dress fitting and picking out the lingerie she would be wearing under her dress.
I had always been a prude, and wasn't even comfortable changing in front of other girls, but my sister was much more open and over the course of a couple hours of her trying on different lingerie and her wedding dress and me trying on my bridesmaid dress I had gotten in the spirit and by the end of the day I wasn't even turning my back to get changed.
We arrived back at her apartment and opened a bottle of wine and kept talking about wedding and honeymoon plans. The earlier casual nudity combined with the wine and hearing my sister talk about her honeymoon had me in a low-grade horny place for reasons I didn't really understand.
Her fiancé came home about an hour later, and we already had a bit of a buzz going. He started drinking beer and we all caught up on our day. I made a few references to the lingerie he would be seeing in a couple weeks and that he was going to like it a lot. He asked for a fashion show, but my sister insisted that was for the wedding night.
We debated going out to a bar, but they were saving every penny for the wedding and we decided to stay in and play some cards instead. We played hearts, and gin, and over the next couple hours finished our second bottle of wine while he stuck to drinking beer.
We were trying to figure out what card game to play next, and I said, "well we could play poker, but I know you guys are trying to save money, so we would have to play strip poker."
Everything got really quiet. My sister looked at me with a total look of shock on her face. They both still thought of me as a total prude, and I was buzzed enough that I thought I needed to make a point. So I started saying that I wasn't going to have to strip because I was going to kick their asses. (I think I had just one the last two games of gin.) This brought out the sister-sister competitiveness that we had always had being less than 2 years apart in age.
My future BIL said, "Jane, we all know you're not going to play strip poker." In retrospect this was a great play on his part. Gave him cover with his soon to be wife, he wasn't pushing it, but it also put a challenge to me. He called my bluff, after all, I was the one who brought up strip poker.
Now it was just a question of who would back down first. They were sure I would back down. And I was pretty sure my sister wouldn't let it happen, or would stop before it went too far. I was wrong. We were all buzzed enough, and from what she told me later I was being really annoying about how good I was at cards, so my sister just decided to let things play out. Plus I found out later that her fiancé loved playing strip games and they had done it just the two of them and with other people a few times. It wasn't a huge turn on for her, but she didn't mind it and she knew how much he liked it so she was pretty game, at least if she was buzzed. I realized that she was going to make a great wife.
So my bluff has been called, and I decided that I'm not backing down. I pick up the cards and start dealing, 5 card draw, deuces wild. We played for 5-6 hands where the losing hand was someone different every time and we all had lost our shoes and socks. Still plenty of time for someone to end this.
Then (future) BIL loses three hands in a row and is down to his boxers. I of course start totally trash talking about how good I am at cards and how he's going to be naked in a minute. But he doesn't react at all except to say that I'm just getting lucky, and just picks up the deck, shuffles and deals.
On the next hand I try for a straight and end up with 9 as my highest card. My winning streak is over. And for the first time, I realize that while I still feel totally dressed (sweat pants, t-shirt, bra and panties) with this loss I'm going to be showing either my bra or panties right now. I totally freeze trying to figure out if I'm actually doing this, and if I am what should I take off.
(future) BIL says, "It's ok Jane, we knew you aren't comfortable doing this. It's ok to quit". The fact that we was saying this while sitting in his boxers, one hand away from being naked, made the point that he wasn't backing down. My sister was dressed the same as me, and was mostly just tired of my trash talking.
I jumped up and stripped off my t-shirt and made some joke about my small boobs. Nobody took the bait and my sister dealt the next hand. She lost and removed her t-shirt, leaving us both sitting in our bras. I didn't like the comparison between her C+ cups and my B- cups, but nobody was making comments like that and the game quickly resumed.
I lost the next hand, and took off my sweat pants without standing up. Now it was getting serious. I kept telling myself that if BIL lost just one hand we could call the game over without anyone giving in, but he kept not losing.
My sister lost the next hand and took of her pants. This was now real strip poker. The next hand we were going to see something we had never seen before.
My sister lost again, and with no hesitation reached behind her back, un-clasped her bra, and flung it into the corner of the room. She sat up proudly, didn't cover her boobs at all, and just said, "deal." It was at that moment that I realized that I was going to get naked. I wasn't going to back down, and clearly neither were they.
I didn't have to wait long, I lost the next hand. I tried to match my sister's casual removal of the bra, and came up with what I thought was a great line. "Take a good luck guys, only a few people have seen these tiny boobs."
They both complimented me on my boobs and my bravery, and we dealt the next hand.
I lost again. I couldn't believe it. My sister and I had lost 7 out of the last 8 games and now I had to take off my undies.
I stood up to make a statement that I would proudly get naked not hide under the table. Before I could take off my panties, BIL suggested that since we were all down to one item, we just stand up and strip together. This made sense in our drunken state and so we all stood up and said 1-2-3 and then we all pushed down and stepped out of our underwear.
We stood there for a minute openly checking each other out. Then my sister said, "group hug" and we all hugged naked for a minute. Then we got dressed and put on a movie.
That was my first time playing strip poker, and it was awesome.
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