I was 13 going on 14 when I got my first boyfriend. He was my best friend we had known each other for a year almost 2. We had the normal sleepovers kids have. I seen him naked and he seen me naked. He didn't know that I was a crossdresser or that I even pretended to be a girl some times I didn't even know what it was called back in 1993, I just knew I was different. It happened one snowy day in January of 94. School had been closed for the day. I was always over there at 600 in the morning to walk to the bus stop with him and our other buddies. So naturally I went there like I always did. I walked in and his parents had left for work already and his little brother was at the babysitters. Nothing different than any other day, except the fact that Mike wasn't up yet. I called out his name and he called out in my room. I went to his room and I opened the door and walked in there he was laying in bed naked with a hard-on. I've never seen his dick hard before I got all flustered and said fuck sorry and closed the door. I went and sat on the couch thinking of his dick and how inwanted it in my mouth and to sit on it. He came out and sat down and we started watching TV. After a while he asked if inwanted to go look in his mom and dad's room for their cigarettes so we had a pack for the day I said yes. We went in the room and started looking for them. I immediately went to his mom's side of the dresser and started looking threw the drawers. To my surprise she had some very sexy panties. Nothing like I ever seen before. Now mind you up until now the only access I had to woman's clothing was my heavy set mother's granny panties and moomoos and my sisters normal 90s kids clothing. When I saw the panties and bras his mom had my mind started racing. As I touched the soft material my heart was pounding and I was wishing I could try some of it on but didn't want to be made fun of by Mike. So I closed the drawer and went to the closet.i opened the closet amd there in front of me were some sexy dresses. I couldn't handle it I needed to try stuff on. But how? I asked Mike of he found the smokes yet he said no and I said me either. Just then I heard the distinct sound of a vhs tape being pushed into a vcr. My 80s and 90s people know the sound I'm talking about lol.i turn around and my eyes get locked on the TV of a guy getting a blowjob by this brunette. I looked at Mike who was sitting on the bed watching, he said wanna watch with me? I went and sat next to him and watched my first porno movie. He looked at me and said to bad theres no girl here and he chuckled. I laughed and said yeah right. A couple more minutes went by and my little clit was getting harder and harder. I glanced over at Mike and could see he had a huge bulge in his underwear. We made eye contact and he said we could do what they are doing I won't tell if you won't. I said ok but under one condition, he said what's that I replied with you have to let me be the girl and I get to dress in your mom's clothes. He just stared at me...immediately my heart started racing thinking oh fuck oh fuck...when he replied with you do that? You want to be the girl. Then I explained to him about me and he was like ok I don't care. So I made him get out while I picked out the perfect outfit. I was overly excited I only dressed in front of 1 other person and that don't count to me ill explain that in another story. I picked a pair of black thigh highs and then I picked out a silky sorta see thru night gown. I grabbed a bra and put it on I stuffed it with a couple tshirts. I stood there and looked at myself in the mirror. This was way better then my mom's granny nightgowns. I got on the bed and called him in. He walked in and saw me and said wow you make a cute girl. I just smiled and said thanks. He got on the bed and I stripped him out of his clothes. The girl on TV was sucking the guys cock so I didn't waste any time. I grabbed his 8 inch cock and immediately put it in my mouth.