my first time

I had seen his ad on Craigslist something along the lines of bio guy looking for an ftm. I had just started exploring the world of anonymous play with non trans guys, but had yet to actually do a hookup. I had been surfing the net a lot – reading mystery fag and transfag blogs which are hot if you have not read them check them out. I also had read the safer sex for trans guys guide a ridiculous amount of times. Nerd that i am i had done my homework.

I had posted on Craigslist and gotten a lot of response, a few interesting, a few creepy, and a lot in between. I was on Manhunt and Adam4Adam but in a very tentative kind of way which for me looked like a clothed pic and blurry face pics and a profile that didn’t say much. I had chatted with some guys, but I had yet to set something up.

His ad said he’d been with trans guys before so I decided to message him. He responded right away and we exchanged pics. He was cute, late 20’s or so, black guy, skinny. We chatted for a while exchanging a lot of emails. So he said when you want to meet. I was pretty nervous about it all, but there really wasn’t anymore to say via email, I put it off for a bit, but then decided to just go for it and we set a date.

That night I put on a cute outfit, made sure I was bound up (i used to worry that because i have not had top surgery it would turns guys off but that has not been an issue so far), trying to look as 'guy' like as possible, I headed out. I was nervous but excited.

When I was a few blocks from his place I texted him, he said he would meet me outside. I got to his place. He looks different than I expected, extra skinny, very gay, not my kind of hot, but not unattractive, he just got off work so has on a button up and slacks. I say stupid nervous stuff as we head up to his apartment. He takes me to his room which is incredibly neat. We sit on his bed and chat about random stuff. Then he says you are way cuter than your pictures. I just smile.

He leans in and kisses me. We kiss for a while, he is a really good kisser. He's very confident which i like, he unbuttons my shirt and pulls of my top and binder and unbuttons my pants, I pull them off and help him with his. I’ve been pussy fucked before, but never with a live cock. I’m nervous.

As a result, I don’t remember a whole lot about the fucking except that it was good and not long but not short and that there were some hot moments. I also let him fuck me in the ass which was incredibly painful and a little messy which I felt embarrassed about but he didn’t care. The ass fucking wasn’t particularly enjoyable and I know that at the time I did it because I felt I needed to in order to fuck gay boys.

After we fucked, we chatted more about our lives, he kept saying how hot i was, how sexy I am, how he’s sure I can get any guy I want. It was a definite ego boost. As I’m getting up to go he asks if I want to see him again, he says be honest, I’m not sure but say yes.

Heading home, I stop at a coffee shop to use the bathroom and clean up. I don’t know yet to just ask to use the bathroom and rinse off before I leave a hookup. My ass is sore, I feel like I smell like sex, I clearly need a shower. To be honest while I would like to say I was totally happy and excited, I remember mostly feeling glad that I hadn’t been killed, robbed or made to do things I didn’t want – basically I remember feeling sticky, sore and relieved that I had finally done it.

I got home, showered, and made some food. Once I was feeling a little more together I remember smiling to myself – I felt good in my body – good that I had overcome my fear and nervousness, good that I had taken control of my sexuality in a way I had not before, good to be desired and considered hot and sexy, just good in all off my little transboy gayness.