My Second Time

I hope you've been enjoying my previous stories thus far. As you know (unless you HAVEN'T read them) my stories are short, true, and to the point, so you may enjoy them that much quicker without reading long drawn out writings. So here is another true story for your enjoyment.

This was my second time (well, technically my third, as the first guy fucked me twice within ten minutes). From back in the days of placing ads in the personals section of a local paper (the youth of today has no idea what the pre-smartphone era was like), this story takes place. It was somewhere around '96 or' 97, and not too long after the first time. I was married to my first wife at that time, later becoming my ex (but ironically, we got divorced because SHE cheated on ME, having had no idea that I was cheating on HER, by getting fucked by men while dressed in women's clothes. But isn't it cheating only if it were another woman...?).

So, having really (REALLY) enjoyed my first time, I placed my ad in the paper, and waited, and hoped for, the replies to start coming. Of course I received plenty of replies, just not many serious (or sane) ones. But alas, finally, after a couple weeks if I recall, I got one that I went with (who agreed to meet and could host, the latter of which was, and still is, a must). He lived alone, was about the same age, and was close to where I lived. The shorter the time away from home the better as to not arouse too much suspicion. He was also a crossdresser, which peaked my interest even more.

For the week prior to the agreed upon date, I was nervous as hell, just like I had been leading up to my first time, and every time thereafter. The nerves never go away, it feels like the first meeting every time. You just don't know what you're getting into until you get there. I've had sex with 19 men to date, the next one will be number 20! Hoping to make this happen very soon, but unfortunately, sometimes the dry spell lasts a year or more. That's not good, but thank goodness for porn and masturbation. And thank goodness for Craigslist too! Sure wish they'd been around back then; I'd be WELL over 19 by now. But better late than never!

So the day finally came. The day dragged on at work, of course, the anticipation of what would happen later that evening predominantly occupying my mind. I had again made up another story about helping a friend or meeting some guys from work. I had to keep my stuff hidden away, my first wife knew but disapproved of my dressing. So I kept my stash all stuffed away in my toolbox in my basement. We lived in an apartment and had a shared basement, and I would often go down there and change, sneak over to the other side of the basement (someone else's space, so quite risky but so much more erotic), and rubbed one out. Left a lot of DNA in that basement, never getting caught, but came real close a couple times. Just adds to the thrill, and a much more powerful orgasm!

But on this day, my stash would make it out of the toolbox and into my car for an evening out. Following the directions he gave me (no GPS's back then either, I'm feeling old), and arrived at his apartment. I rang the bell and he buzzed me in. It was a two-family unit, he was in the upstairs apartment, and was waiting atop the stairs dressed in a hot minidress, nylons and high heels. We went inside, he saying he couldn't wait to see me dressed. We talked for what seemed to be too long (I wasn't there to talk), before he finally suggested I change in the bathroom. I changed into the same red velvet dress I wore during my first time, a purple teddy, black fishnets and black 4" strapped sandal 'fuck-me' shoes.

At this point, I had very little experience, as this was only my second hookup with a guy. I asked if I could ride, he agreed, and I tried. I got on it but it was too painful (now I can ride a baseball bat but not back in the early days). We moved to the floor and I got on all fours. He entered me in what was to be my very first doggy fuck! It hurt as well, but I was going to go to the end. No matter how much it hurt, it was still an amazing feeling, a big cock stretching my asshole to the point of never before. In and out, I couldn't wait for him to finish, and at the same time, I hoped it wouldn't end!

Eventually (and sadly as well) he came, his cock pulsating in my ass, I could feel it against the ring of my anus. I told him I wanted to fuck him now, but as with most guys, nobody wants to GET fucked after they cum. I look forward to the opportunity to GET fucked AFTER I fuck someone else. I guess it's called 'flip' fucking. I so love getting fucked that I'd have no problem doing that. So as usual, I took care of myself, but certainly was not leaving disappointed! There have been plenty of hookups that WERE disappointing, a 'failure to launch' type of thing, but the majority of my hookups have been successful and memorable, and I'm glad to finally share them with other like-minded people. It's nice to be able to be honest, to share my life experiences, and not be judged as society judges people who engage in this type of lifestyle. They just don't know what they're missing!

As always, I hope you have enjoyed reading. This was as accurate as I can remember, being so long ago. I might follow with another story if I get enough requests to do so. Thanks to everyone who has read my stories, and special thanks for the kind positive comments, I'm glad you enjoy what I share with you!