Once I posted a M4W Casual Encounters ad on Craigslist, which included a couple of the pictures from my profile here. One response I got was from someone who didn’t say much more than that she was a “cute girl” who thought that my “um, parts, are kind of amazing!”. I responded, but never heard anything more from the cute girl.

Until several months later. Out of nowhere the girl picked up the conversation again as though she were responding to me the very next day. She was still interested; was I?

I was: still available, and curious to see if I’d be interested in hooking up with this person. So we got to talking and sending pics to each other. M.’s pics were very nice, although in a slightly off-putting way (you already know from the title of this entry why that was the case). She was interested in phone sex pretty much right away, so we did that. I’m not crazy about phone sex because I’m not great at sex talk, but it was hot for me, and even hotter for M., who (ostensibly at least) orgasmed during it.

After that, M. was very interested in meeting in person. And it was only at this time that she cleared up some ambiguity about her gender: she was in fact a female-to-male transsexual who had already been in the process of taking hormones to become more masculine.

So now it was on me to decide whether I was willing to proceed to an in-person meeting. I spent a lot of time agonizing over this decision. On the one hand, M. was quite attractive and had a nice body (as a female). She was several years younger than me, and latin (I have a major thing for latin women). She said she was a squirter, which is something I had never experienced before (and definitely wanted to). She said that the hormones she’d been taking were making her crazy horny. They’d also made her clit huge; I’d never played with a particularly big clit before, much less a huge one, and this was another thing that I’d been interested in experiencing.

On the other hand, of course, M. was, well, technically male. She considered herself a guy, and her hormone treatments had certainly gone a long way toward making her look that way.

The thing that I eventually realized that was key to making my decision was that, whatever M. or the people around her or society or the law thought of her gender, for the purposes of my sexual attraction to her, she was definitely female to me (hence my consistent use of feminine pronouns for her here). This wasn’t a reasoned choice; it was how my body FELT toward her. I knew that her masculine characteristics would undercut that attraction somewhat, and I wouldn’t know to what extent it would do so until/if we actually got to the point of having sex. But I did want to get to that point. I was too turned on by the “on the one hand” qualities described above.

So we met up. We started with drinks at a bar near where she lived, to make sure we were both okay with going further. We were; we hit it off great, and M. looked plenty fuckable to me. On to her place then!

Once at M.'s place, we wasted no more time in getting down to it. She sure hadn't been lying about being very horny; she was an absolutely ferocious fuck, full of energy and orgasms. I made a point of seeing what her huge clit was like. The light was really low in the room, so I basically didn't get to see it; but feeling it against my tongue and in my mouth, I could tell it really was huge. It wasn't "hard", though. At any rate, I didn't get to spend very long eating her out; M. wanted me inside her bad, so she pushed to get to that point.

And I dare say she was happy with it. M. had come through on the super horniness and the big clit claims; soon enough she also proved her squirting ability as well. Like I said, I had never experienced this before, so it was very exciting for me. Though, there wasn't much to it. M. had her first orgasm (she was on top at the time), and suddenly there was warm water all over my legs.

That was the only time that M. squirted, but far from the first time that she had an orgasm. At one point, she said "I love your cock. It made me cum three times!" And she went on to cum another four times. I had one myself, my usual. But I kept going for a long second (or third, or whatever) round, which is how M. got to her high orgasm count.

I ended up staying the night. I don't think M. wanted (or liked) this, but she kept me up so late with the long sex session and then watching DVD's afterward (and I was so drunk; we did a lot of drinking) that my going home became unthinkable. We had another round of sex in the morning, but it was much shorter, and I think there wasn't a single orgasm during it. It didn't help (me) that for the morning sex I was seeing M. in full daylight - seeing just how masculine she really was starting to look. It was frankly a little disturbing, and it made me realize that there was no way that M. and I could hook up again. And so it was that we left it at just the one wild, wild night.