I was heartbroken that i had to take off everything, but i did and i put everything in the room back to the way it was. At least once a week i would dress up in different clothes, but the time after this was when i really discovered how fun it was to cross dress.After the first time i crossdressed in my sisters clothes, i just had to do it again. It was a week until i had the house to myself for a couple hours. Right when my family left i went to my sisters room and picked out some clothes different than the ones i wore last time. I chose my sisters dark purple prom dress that goes down to my upper thighs. I also got her black strapless bra, her cute black thong, the blonde wig and makeup bag from last time, I went back to my room and locked the door to re shaved everything again, I slowly put on the thong because i love the feeling, then put on and stuffed the bra. It took me a little bit to get the dress on but when i finally did it was worth it. After i applied the make up and put. I suggested playing some board games and some video games to pass the time. So, by the time we had run out of things to play it was around 11 that night. As I folded out the futon bed I recall her asking me something very personal: “Hey David….um…have you ever been with a girl. You know like intimately?” Shocked at her question I hesitated a bit and then said “No, have you ever been with a guy before?” “No, I was just wondering.” That was a relief, I did not want my precious flower to have been soiled by some jerk at school. After a while of trying to decide what we wanted to do for the rest of the night (movies, games, etc. were all mentioned), I had a sinister idea to perhaps be her first. I mentioned that maybe we should make up a game. She was all ears and grabbed a piece of paper to write down the score and perhaps some rules. “Okay” I said, “Basically this is a game of bravery. You score one point for every easy challenge and 2 points for a difficult challenge. Now, once you.
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