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. So my first time was followed ten minutes later by my second time. He then fucks me from behind laying down. He asks me to take off my dress and lay on my belly. He's hard again in ten minutes! I ask him to fuck me again, and he, of course, doesn't say no. Not more than a couple minutes later it's over, but not for long. He made love to me, gentle and deep and awesome, just an incredible feeling! 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. But it made me feel so much like the woman I wanted to be that night. 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. I was feeling electrified! He didn't waste any time, pulling out the couch into a bed. I come back out to his living room and he was very satisfied with what he saw. 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. 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. He lets me in to a nice place, and we sit on the couch and talk for a while. I get to his apartment feeling so nervous yet more alive than ever. 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 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.
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I whacked off countless times fantasizing about how it would be, what it would feel like.įinally, the day came. I just couldn't wait for that day to come! It was a week away yet. He wanted to double to me exactly what I wanted him to do to me. It has to be mutual for anything to work. We talked about what we wanted out of this, and we were definitely on the same page. He seemed really nice, Laos back, and understood my nerves and that it would be my first time. So I went out back where I would have privacy, and dialed the number he left in my message box on the dating service. The work, having some complex accessories installed, would take a few hours. I would be waiting for it as my wife didn't drive not did we have two vehicles. I had an appointment to have some work done on my car. 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. They had pretty much just come out to 'the masses' at that time. Now, in 1994, I got my very first cell phone. But I did have someone reply to my ad, and my first time was off to the races. Not too successful, people didn't like paying for stuff (some things haven't changed though lol).
FIRST TIME CROSSDRESSER IN A GAY BAR PORN FOR FREE
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. I knew what I wanted, and I wanted to be fucked by a man!Īt that time the best means of 'hooking up' was putting an ad in the local paper dating section. There came a point where fantasy just wasn't enough anymore.
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I had fantasized for many years about getting together with a man while dressed how I love to be dressed. I was feeling a different feeling than ever before. This was before the explosion of the Internet and smartphones. I am very lucky to have had these experiences and I hope you enjoy my sharing them with you. As I said in my first story, MY stories are totally real, they really happened and happened just as I describe.
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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.