I was 16 when i first felt a cock pushing inside my tight asshole, I knew this is the only way I am going to have for the rest of my life......SISSY FOR LIFE

So my 10th grade year, my best friend (at the time) and I started talking about how we would masturbate. Sometimes when we would stay the night at each other’s house, we would decide to masturbate but not looking at each other. We would fantasize about the hot girl together. Well one day we were just hanging out in his parent’s camper behind the house. We lifted up the mattress pad and found his elder brother stash of porno magz. We browsed through them and decided to masturbate. So it sorta became a thing to masturbate together to his brother's porn. We found a video once to and would like masturbate… well after a while of masturbating in each other’s presence we started to joke about “I’ll do you if you do me” type of thing… well i eventually was like sure.. So we would masturbate each other off in my parent’s boat house. It just kept escalating… eventually I would suck his cock and then he would suck me. I had an older sister, who was in college… well one time my friend was like “dude you should wear your sisters clothes, you are feminine and you would look like a hot girl.” I said no way. However it did turn me on a little. I was joking and said the only way I would do that is if I could look like a girl. Like with a wig or whatever. Well I think we were sorta excited by it maybe for different reasons. I had dabbled in x dressing before since like 8th grade. He was obviously not aware. I think he just liked the idea of a girl getting him off. Well he got the courage to walk into a high end shop for like lingerie and toys. They had above party wig quality wigs… he showed up one night when we were spending the night. Pulled out the blonde bob style and said let’s see if you put on the girl outfit… I was nervous. I told him just wait a second… I wanted to go full out, so I did makeup and everything (which I stole from my sister) shaved what little hair I had off my legs and put on some nylons and wore the lingerie and on top wore a mini skirt and hatler blouse and the wig. I walk into the room soo embarrassed but he was in shock. I was too because already he was super hard. I felt vulnerable as the skirt was so short and I knew the panties were showing. But I got down on my knees and sucked him off. It just continued to escalate. One time I climbed on the bed after teasing him and giving him a bj for a bit. I bent over in a doggy style position, and told him he could fuck me. He tore the nylons, pulled the panty to the side… and he (with some lube) fucked me until he came inside me… It turned me on so much that he got hard thinking of me and his blonde cheerleader. I sexual fantasy and in those moments he thought of me as a girl and I felt the same. I would just masturbate during those moments. I guess I took his virginity, and in a way he lost it to a blonde babe. Lol