by Lovinhose 09/20/13
When I posted my first story, about my most recent experience, I promised to follow up with other stories, including my first time sex as a crossdresser. So here it is. This is the story of my very first time. As I said in my first story, MY stories are totally real, they really happened and happened just as I describe. Nothing at all is made up. I am very lucky to have had these experiences and I hope you enjoy my sharing them with you.
My first time. It happened back in 1996. This was before the explosion of the Internet and smartphones. I was feeling a different feeling than ever before. I had fantasized for many years about getting together with a man while dressed how I love to be dressed. There came a point where fantasy just wasn't enough anymore. I knew what I wanted, and I wanted to be fucked by a man!
At that time the best means of 'hooking up' was putting an ad in the local paper dating section. You could place an ad for free but anyone who wanted to respond, via a voice-message system, had to pay with 'credits' you could buy. Not too successful, people didn't like paying for stuff (some things haven't changed though lol). But I did have someone reply to my ad, and my first time was off to the races.
Now, in 1994, I got my very first cell phone. They had pretty much just come out to 'the masses' at that time. This was a very good thing. Trying to carry on a conversation on a public phone or at home, about the subject matter in which we would be discussing, wasn't a desirable situation. So my cell came in very handy.
I had an appointment to have some work done on my car. I would be waiting for it as my wife didn't drive not did we have two vehicles. The work, having some complex accessories installed, would take a few hours. So I went out back where I would have privacy, and dialed the number he left in my message box on the dating service. We hit it off right away. He seemed really nice, Laos back, and understood my nerves and that it would be my first time. My excitement level was peaked!
We talked about what we wanted out of this, and we were definitely on the same page. It has to be mutual for anything to work. He wanted to double to me exactly what I wanted him to do to me. We agreed on a day to meet. I just couldn't wait for that day to come! It was a week away yet. I was a wreck for that week. Nerves. Anxiety. Excitement. Anticipation. I whacked off countless times fantasizing about how it would be, what it would feel like.
Finally, the day came. It was the longest work day of my life. I told my wife was going to help a friend move some stuff after work so she wouldn't question why I was home later than usual. I had my stuff in the car already. I got off work, called him to make sure we were still on (a part of me hoping something had come up so I wouldn't have to go through with it...cold feet I guess), and subsequently drove over to his place with the directions he gave me.
I get to his apartment feeling so nervous yet more alive than ever. More nervous than ever in my life. He lets me in to a nice place, and we sit on the couch and talk for a while. He asks me if I'm still wanting to so this and I said I definitely was! He said I could change in the other room. In I went with my box of stuff. I put on a little makeup, then black panties, black thighs highs, a purple teddy with black lace trim, and a long sleeve red velvet below - the - knee dress.
I come back out to his living room and he was very satisfied with what he saw. I was feeling electrified! He didn't waste any time, pulling out the couch into a bed. I lay on my back, and he starts kissing me! That was a first, well, all of this was, but I never factored that into what we'd be doing. But it made me feel so much like the woman I wanted to be that night. Then comes the best part. He penetrator me (wearing a condom), and just like in the movies, and like the women I've fucked, I wrap my legs around his back, and I am no longer a virgin! It doesn't hurt like I heard, surprisingly no pain, and he was the biggest to fuck me to this day. He made love to me, gentle and deep and awesome, just an incredible feeling!
Not more than a couple minutes later it's over, but not for long. He's hard again in ten minutes! I ask him to fuck me again, and he, of course, doesn't say no. He asks me to take off my dress and lay on my belly. He then fucks me from behind laying down. So my first time was followed ten minutes later by my second time. It is very unfortunate that time got away from us after that, and we never did meet again, but seldom do you meet the same person again anyway. I did have a regular for a short time, and I'll tell you all about that in a later offering. Hope you enjoyed this, and my previous stories. All my stories really happened. Another story to follow, if you guys want me to write about more of my many experiences.
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