My First Time With Crossdresser

I wrote a story on here on my first time dressing in pantyhose and heels and having my female friend make me suck her dildo. After a few months of doing this, I began to get curious on what it is like to suck a real cock. I finally did it with a super hot, petite, totally passable Transsexual who no one would ever know she wasn't a 100% female. I really enjoyed doing it my first time.

A month later, I was checking out Tranny escort ads on the web one morning and see an ad a hot Tranny blonde visiting from Texas. She was staying just 2 miles from me. I called, went over and sucked her cock. She fucked my mouth and was pushing my head all the way down on her cock. She came twice. But like a lot of TS girls, nothing comes out because of hormones. I got home and I was craving more. I had answered a few ads on Craiglist for guys looking for guying.

Most of them, like me were married or divorced and discovered the bi fun in their middle ages. I never had the nerve to go through with meeting another guy. I didn't know if I can actually do it. I mean, the Trannies looked just like women. Both were about 5'6" 125lbs, no body hair, smooth skin and tits. But I was so horny I finally wrote a married guy who was persistant on meeting.

He, like I, liked to put on pantyhose, panties and heels. He said to meet him at a motel and he wants to swallow my cum. He did it once before and wants more. So I stopped at Walmart and bought a cheap pair of heels in his size. I brought my pair. He stopped and picked up two pairs of pantyhose. I told him I am not sure I can suck a guy, but at I would give him a hand job. I pulled into the motel parking lot and he was already there. In the room we both get naked and put on the pantyhose and heels.

We lay next to each other rubbing our legs against each others and rubbing each other's cocks through the nylon. I was so turned on thinking to myself, I just sucked off a TS girl and here I am in a motel room with a guy playing with his cock. I made the first move and went down and licked his cock through his pantyhose. I wasn't sure I could suck a guys cock, but I pulled down the waist band of his pantyhose and put it right in my mouth.

He had a nice cock. 7 1/2 inch and cut. I put it all the way in my mouth feeling his head hit the back of my throat. I sucked him for a while and then he went down on me. We 69'd and I was ready to cum. I told him and he said he wants to swallow my load. I did and a few minutes later, he warned me he was going to cum. I told him go ahead and let him cum in my mouth. I did not swallow but let it run out the side of my mouth.

We rested for about 10 minutes and asked him if he can cum again. He said yes. I got lotion I brought with me and started giving him a hand job while I fingered his ass. This was the first time he had anything in his ass. He blew a second load in a short time. We kept our pantyhose and heels on the whole time.

I never thought about dressing up or sucking cock until I was 49 or 50 years old. If I knew it was this much fun, I would have started a long time ago.

cyfree's avatar
cyfree posted 6 year ago

Great story, what an adventure. More. thanks, cyfree<img src="" alt="" class="blog_image" />

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