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.

Beaded Penis

He'd had beads inserted into his penis. When he showed it to me later, I was struck by the ordinariness of it. His penis was short and stump with these tiny sperical objects sticking out at odd intervals. Immediately, I could tell why he needed to adorn his dick with jewelry. Obviously he wanted something more than it could offer. "It enhances the sensation" he said with a smile and I smiled back, more out of politeness than anything. The color of his dick was pretty though. Reddish brown. Slightly darker than the rest of him. It brought to mind ovaltine and for that reason I wanted to taste it. I decided to call him "bumpy" and no, the beads didn't enhance a thing. Bumpy was alright in the sack, though "doggy-style" was certainly his piece de resistance.

Let me say a thing or two about doggy-style. One: rarely do I say "doggy-style" out loud without dissolving into a fit of giggles. It's just such a silly name and belies the seriousness of the act. Two: In my former life, I hated this position. It just seemed too vulnerable of a state to be in. Getting down on all fours, and allowing someone else to see all into your asscrack. My middle-class demure upbringing just wouldn't let me get into it! This was of course back when I set way too many boundaries around my sexuality, or rather when I allowed social norms to dictate how and when I should fuck. Well, here I am years later and I have to say "doggy" or "down on all fours" has become one of my faves. Not only does it make it easier for my g-spot to be stimulated, it also is just erotic as hell when a guy hangs onto my waist or my ass for leverage and pounds my ass. There's something so primal about the position which also adds to the appeal of it. And whatever Bumpy lacked in dick girth, he certainly made up in motion. Yeah, there may be a thing or two to that "motion in the ocean" adage.

Bumpy and I rendezvous-ed twice, which is my limit with most men I sleep with. I rarely ever cross over into thrice or we may as well be dating. I don't do "regular fucks". I figure if I've reached that level with a dude, then there had better be more than just fucking going on. In other words, I tend to get attached. It's the way I'm made up. Anyway, Bumpy and I did our thing twice and the 2nd time was even hotter. He hosted this time and his roommate, the ex-girlfriend (or so I was told), was out doing god knows what. He invited me into his giant soft bed and proceeded to lick the hell out of my pussy. That-is-what-I-am-talking-about. I may have said that out loud, in between bellows of "yes" and "god" and "I'm gonna cum". Yeah, it was good that 2nd time.

And there would have been a 3rd time if he hadn't gone and freaked out over the trans bit. By fuck session number 2 I'd started experiencing all the usual changes trans dudes experience. I don't know who he thought he was screwing. He must have blocked out the "I'm a trans dude" portion of our introduction. For some reason he'd look at the hair growing on my chin and chest, hear my deep voice, and still refer to me as "ma". After the umpteenth time of this I had to remind him. Well, lets just say, my usual "I'm a dude with a vag" shpiel is a bit of a mind fuck for people who aren't in the know. I understand that. After all, we all grow up hearing and believing so many untruths about gender. Hell, I hardly know what it is any more. I'm a patient dude. I can wait for you to have your epiphany and realize that actually there isn't a lot about gender that's set in stone or genetically predetermined. I do draw the line at pretending though. If you're turned on by this here trans boy and we're going to fuck, you'd better face up to what you're desiring. Bumpy couldn't, or rather, he wouldn't. Goodbye Bumpy!

Tall, dark, n' lovely.

He fucked me hard and deep. 6 feet 5. Locks down his back, formed into pretty long braids that he kept having to flip out of his face as he bent over me and entered me gently. He hadn't had pussy in 3 years and some change. The ideas of a guy with a vag confused and turned him on simultaneously. That's the reason he hit me up on adam4adam. That and the picture where I'm flexing my arms - one of my best features, by the way. He flipped my legs up in the air. Placed my feet on his chest. I could feel his heart hammering away. His big dick plunged into me and I gasped. He was gentle at first. "You're so tight," he whispered as he withdrew and entered faster this time. I closed my eyes and moaned. God he could fuck. God he was big. And I could no longer stop the sounds spewing out of my mouth. This is why I love Black men - the connection formed as skin comes upon skin.

"Hold onto my arms like that, baby boi. I got you," he said as he plunged in deeper. I grabbed his shoulders, now thinly layered by a film of sweat. It was almost too much. A sweet, delicious pain. I dared to look down to where the action was happening. "You see that dick?" he grunted as he fucked me faster. I did. I got wetter at the sight if his dick going in and out of me. This 6 foot 5 giant now cradling my ass with a gentleness challenged only by the ferocity with which he pounded my pussy. His eyes boring into mine. My mouth agape. Sounds I could barely recognize as mine escaping them. I thought, as he leaned down to wrap his tongue around mine, I am never fucking white men again.