Vanessa's First Date

By vanessagrrl

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Tags: crossdressing, mm, handjob, hotel

Added: 02 Jan 2013 Views: 14358 Avg Score: 4.38

This is a memoir of my first time meeting a man.

I'd been crossdressing for many years. I had many fun nights dressing up and playing with my toys but I wanted something more. I liked to get on the phone with guys and play around. I had my favorite toys to use, especially my eight inch dildo and my butt plug. I really got into my phone sessions, but I felt like I wanted to go further.

There was a nice guy who I had been talking to for a while, and I got to know a little better than the average phone fuck. He was friendly and sweet, and made me comfortable.

One night, he finally asked me if I wanted to get together. I was surprised it took him so long to pop that question, but maybe that was why I felt so comfortable with him. I was nervous, but I decided that it was time to give it a shot.

We agreed to meet at a local motel. I got dressed in a sexy tight, mini-skirt, blouse, garters, stockings, lacy bra and thong, and five inch heels. I did my make up nice and sexy with red lips and nails. I looked so slutty, and I wanted to make this guy's jaw drop.

We pulled up to each other in the parking lot as agreed. We wanted to make sure we were both comfortable before going any further. One look was all it took, and we agreed that he would go get us a room. He came back and we walked into the room together. We stood there for a few minutes, a little bit nervous. He had some booze, so he poured us both a drink to loosen us up. Then, after talking for a little bit, he asked me if it would be okay if he took down his pants and showed me his cock. I told him that I'd like that, so he did. It was about six inches and thick.

I reached out to touch it. It was so strange, but such a turn on. I had never felt another man's cock in my hand before, but I liked the way it felt. I liked hearing him moan as I stroked it, and got it harder. We moved over to the bed, and he pulled my skirt up and moved my thong over so he could stroke my already hard cock. We played with each others' cocks for a while, enjoying each others' moans.

I wasn't sure where this would lead, but I figured I might as well go one step further. I was about to put my mouth on his cock when he exploded his load in my hand. What a disappointment! Not wanting me to leave without having some fun, he asked me to do what I would normally do. Good thing I brought my big eight inch dildo with me.

I lubed myself up and began fucking myself with it, until he grabbed it and took over. He fucked me with that dildo so good. It was the first time I had another person use it on me, and it was so hot. I told him, "Next time I want that to be your cock inside me," and he fucked me faster with it.

I was fantasizing about him fucking me, and shooting his hot cum deep inside me. He kept it up until I shot my load all over myself. We talked for a bit and got cleaned up. I drove home that night feeling a little tense, but knowing that I took that next necessary step into my girlhood.

When I got in, I looked at Vanessa in the mirror and enjoyed the memory of my first cock.