Ever since I was young I have always been attracted to Lady's clothes over boring mens. I started wearing my sisters skirts and dresses when I was four years old. I just loved the feeling compared boys.
And so it started. Throughout by early life I would try on my big sisters clothes in secret. I was wear her makeup, I just loved to feel so girly.
As I grew older I moved away from home to go to college, a new life a new me. I bought some clothes, including panties and bras, I starting wearing it around the dorm. It felt great, but always in private. I then house shared, whenever my room mate was at work, the skirts would come out.
When I was 25 I told a close friend, it was such a huge relief, then came the parents and work colleagues, I don't want to look like a women, I just love the clothes they wear. When I was 27 I started wearing mainly skirts to work. It was a big step, but no one battered an eyelid.
I had always been attracted to Men as well as Women, I was sat at my desk one day, one of the guys, he is married with two kids, came over so I could show him how to do something. Whilst he was sat at my desk he slipped his hand up my skirt and started rubbing my silk pink panties, wow! I was not expecting that. I came almost immediately. I couldn't move my cock was so hard. I calmed down and had to go to the bathroom to masturbate. The guy came over more often after that, always slipping his hand into the inside of my leg, he made me so horny, I just wanted him to fuck me there and then.
I would go home of an evening and stick a vibrator up my ass whilst thinking of him.
I organized a meeting with him in one of the conference rooms, I was wearing a short mini skirt and tight top. I made sure my makeup was immaculate. My choice of panties was a crotchless pair ensuring my ass was easily accessible. The night before I had prepared by ass to make it nice and tight.
I sat down with him, put my hands over his, he slipped his right hand off the table, I knew was was coming next, but this time I was sure we were both going to have a good time. His hand slipped between by legs, my cock was already as hard as it has ever been, it slipped out, he grabbed it and started rubbing it, I ejaculated in seconds. I could see through his trousers he was hard, I undid his belt and slid his trousers down. I wrapped by mouth round his cock and gave him a blow job to remember. We were all over each other, I just hoped no one walked in on us.
I then bent over the table, he could see straight away what I was thinking, he could see my ass primed and ready to go. He slid his cock into my tight ass, I had dreamed and fascinated about this for months, it was now finally happening. He exploded into my ass. Wow, it was just as I wanted.
We were at it in total for two hours, I had to go to the bathroom to wipe his cum from my ass before I could go back to my desk.
Amazing is not the word. We kept going for a few months, I tried to persuade him to leave his wife, but he just wasn't having it. He used to come over to my appartment purely for the sex, but I had to end it.
I am now seeing another guy, we have bought an appartment in midtown New York, and now I can have his cock inside me anytime I want. I am now more or less a full time cross dresser, I have thought about the op, but right now, I am happy being a man, just with the freedom of wearing what I want.
