This is a print version of story How I Became a Cross Dresser by kbking70 from

How I Became a Cross Dresser

For as long as I can remember, my s****r dressed me in her clothes and makeup every chance she could find. She was two years older than me, so I didn't have much choice when I was very young. Up until I was about 12 or 13, my mother allowed this to go on, and by the time she said no more dressing me up, it was too late. My s****r and I continued to dress me up in whatever we could find every time my mom left the house.

When I was 15, she had a group of girls sl**p over, and they called me into her room. My s****r had told them all that I liked to dress like a girl, and they wanted to see for themselves. Next thing I knew there were eight girls around me doing my makeup and forcing me to try on various outfits. At 5'4" and 120 lbs at the time, I didn't need much more than a cheap costume wig to look pretty fem. I was loving the attention and never considered the potential repercussions.

By Monday morning my entire high school knew. I was the 10th grade "queer" that liked to dress like a girl. Having such a small frame and a high pitched voice didn't help. I immediately went from being somewhat popular to being outcast. At this point, I didn't even knew I liked men. That changed very quickly though.

Shortly after my 16th birthday, my mom and s****r went to look at a college, and left me home alone for the weekend. About 10 pm on the Friday night, there was a knock at my door. When I opened it, one of my s****r's boyfriends, Paul, was standing at the door. He was a senior and very cute. Preppy guy about 5'10" and 185 lbs. I believe he played wide receiver for the football team. He asked if he could come in.

He came inside and offered me a beer and we began chatting. Paul finally asked, "So is it really true you like dressing like a girl, or was that just a one-time deal?" I don't know why, but I admitted I liked it. He then asked, "Can I see?"

We went back to my s****r's room and I did my makeup and put on a blonde wig I stole from my mom's closet (not sure why she had it). With my hair and makeup done, he made a comment that I looked just like my s****r. I asked him what he wanted me to wear, and without hesitation he said, "Her cheer leader uniform." I fit into it well, and have to admit, I looked pretty good. Had I had access to the quality of wigs I wear today, I would have been basically undetectable as a male.

He stared at me for a while in disbelief and then just walked over and kissed me. I couldn't believe what was happening. I finally started kissing back and began enjoying myself. Everything felt so right.

Paul then said, "Have you ever sucked a guy before?" I told him no, and that I didn't know if we should be doing this. He responded by dropping his pants and saying, "all the cheerleaders like sucking this dick, even your s****r, and now is your only chance."

My head was swirling around and my heart was pounding in anticipation, so I slowly lowered myself to my knees and grabbed his 6.5" cock. It felt like an eternity before I could, but I took his head in my mouth. "That's a good girl." Paul said.

As soon as his cock was in my mouth, he grabbed the back of my head and started bucking his hips. I had never felt more alive, or sexier, than I did on my knees, dressed like a cheerleader, and getting face fucked by Paul. It didn't take long before his cock started pulsing in my mouth, and I felt the first hot squirt of cum hit the back of my throat. "Swallow like your s****r," was all I remember Paul saying at the time.

When he finished Paul said, "Take off those bloomers and let me see what a cheerleader with a cock looks like." I did as directed and lifted up my skirt to show him my rock hard 6" cock. He said, "Look, I'm not gay, but I understand what's fair is fair. Find me some lotion and I'll jack you off." I didn't waste any time finding that lotion, and then I sat on my s****r’s bed. Paul sat next to me and kissed me while jerking my cock slowly. His tongue was deep in my mouth and he tongue fucked me while jerking on my cock. Within two minutes, I came the most intense orgasm of my life. Paul kissed me one last time, and said he had to go, but he'd be back.

I laid down in my s****r's bed and thought about what had happened. It was the most amazing night of my life, and I learned that there are a group of men out there who loved cross dressers, and I knew I was going to spend the rest of my life finding and pleasing the men.

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