My First Time Crossdressing.
The first time that I crossdressed I was 15 and at my friend's house. We had been left alone on the farm, the three of us, and we couldn't wait to be wild and crazy guys. After watching a huge block of Anime and drinking a few two liters each (possibly 3 or 4) we ran out of ideas as we did not want to start a new game of Monopisk LOTR version (playing monopoly and risk Lord of the Rings versions at the same time). I had been at the time reading stories of crossdressing and transgendered people for a week or so and got the bright idea that we should see what it would be like to be a girl. My friend whose house we were staying at said that if we did it all we had was his mom's clothes. We talked about it for a bit and agreed that we would all do it. We went upstairs and into his parents' room. We opened his mother's closet and drawers when my other friend saw her panties. We didn't want to be total freaks about it so we agreed to wear the panties over our boxers. After about ten minuets I had gotten into a set of white cotton bra and panties and slipped into a pair of her tight jeans and pulled on a floral blouse. My friend (house friend known now as HF) had slipped also into white bra and panties but put on her black dress that she wore to parties. Our other friend (OF) had found her red silk set and put it on while sliding on a short skirt and vest. We laughed for awhile and then decided to put on some make-up and grab a pair of shoes and go into the barn and have a laugh.
We finished up after spending an hour or so in the barn and then returned everything and took a rest. We haven't done anything like that in awhile but we hope to give in another shot someday.