my army guy - about an orgasm

I had hooked up with this guy before, for a while he was one of my regulars, gay, white, working class, used to be in the army, in his 40’s, big tall guy, I wanna say more than 6 feet, 200 something lbs, big and strong, a bears build but with incredibly smooth skin. He has a stunningly beautiful face, just striking, like when he was younger he was one of those shirtless boys on the cover of gay mags, however he looks and dresses like the guy next door mowing his lawn on weekends - Bermuda style shorts, short sleeve button up that stretches over his belly, flip flops.

He’s also a real sweetie. I love big burly ultra masculine guys who are sweethearts.

He sent me a text earlier in the week where he said he wanted to tell me something but didn’t know how to say it in a respectful way (I’m his first trans guy) to which I said just say it no worries. So he said in his entire lifetime he’s only had sex with two women before me or something to that effect… I can feel everyone cringing as you read this, however like I said he’s a total sweet heart and I know he respects my gender, I can tell he’s just struggling with words. So I just say well you know I’m a guy… he said yeah, of course, so I say each trans guy is different but for me you can say I’m only the third pussy you’ve ever fucked unless that’s too crude for you... Then he actually repeats it back to me via text – third pussy I’ve fucked. Totally made me smile. Very teachable.

Anyways onto the fucking cuz that's what this piece is really about.

So I get to his place and he starts kissing me as soon as i walk through the door. I can feel his hard on through his shorts, I'm very turned on. However, he wants to take a shower before we fuck so I decide to join him. His shower is real old school where there is just a shower head and drain in the floor of the bathroom – no stall or tub. This set up makes it extra hot, I’ve never been in a bathhouse but its what I imagine one would be like. We play around some, soaping each other up, I suck him off a bit, then this huge guy, kneels down before me on the old white tile floor and sucks me off, I place my hand on his head as he blows me – shower blow jobs – very hot. We dry off and head to his room.

He lies down on the bed and I climb on top of him, i say climb because that's how big he is. We kiss for a long time – he is an incredible kisser. He flips me over and sucks my nipples then tongues my clit for a while until its too much and I push him off. I put his cock in my mouth, he is already hard as I wrap my lips around his dick, he has a beautiful cock and I go at him for a bit, taking him down my throat, he groans.

He pulls me off and grabs a condom, I lube him up. He lies back and lifts me on top of him, I guide him into me, he's big and thick so i have to go slow at first, just the head until I can take more, he moans as my cunt finally fully encases his cock, I ride him for a while loving the look of pleasure on his face, then he turns me over, fucks me for a while in a couple different position until he lays me on my back puts my legs on his shoulders and as he's stroking says he's gonna cum, I tell him 'cum for me baby' and he starts pounding his full weight into me, until finally he shoots cumming inside me. so hot.

All the while we are fucking he keeps saying how amazing and sexy I am.

We rest for a bit, curled up together, he's a great cuddler. We chat some about our lives, then he starts talking politics, this is when i wish he would stop talking, he's a total conservative. I quickly change the subject - i'm here cuz you're a sweetie and amazing in bed - I don't want to get into your problematic political views.... thankfully, we talk about other random things then he kisses me and i can feel that he's hard again.

He begins fingering my nipples then put his lips around one, sucking until its erect, all the while he's playing with my clit, i moan wanting him badly, he says i just want to make you feel good. i tell him to get a condom and I pull him on top of me. He slowly pushes into me, then begins fucking me missionary style. He fucks me like this for a while and he's stroking me just right... in that way where his cock is filling me up and his body is rubbing my clit just hard enough. I’m glad no one else is home because between the banging of the bed and both of our moans we are being very loud.

He fucks me like this for a long time, our bodies pressed closely together and I can feel that i'm getting close to cumming, i wrap my arms around him, well as far as they'll go, and say into his ear 'don't stop'. he keeps going, stroking me harder and grinding his body against my clit and i'm losing it at this point, i'm raising my hips to meet each stroke, our fucking is frantic, i just keep saying 'don't stop' and he doesn't, as I start to cum his cock plunging deep inside me I hold him even tighter until my body literally explodes, i don't even know what i'm doing as i simultaneously clutch at him and push him away, one of the most incredible orgasms i've ever had.

He’s still fucking me and I can’t take it anymore, i tell him to stop, he stops immediately and looks at me concerned asks if I’m ok, if he hurt me, I shake my head and smile, ‘no man that was amazing’, funny thing about alot of gay boys they have no idea when your cumming. Anyways, he’s still hard, asks if i need to rest, and I do, but i want him to cum too so i shake my head turn around and he fucks me doggy style, its starting to be too much again and i'm about to tell him i can't anymore when he groans and collapses on top of me.

We lie like that for a while, then i move out from under him and put my head on his chest and we just rest.

Then i have to go. As i'm heading out the door I kiss him goodbye and he says please text me so i know you got home safe. I say you're such a sweetie. to which he says, "well we have to look out for each other because no one else will". bad politics and all I can't help but like this guy.

roof top screw

So I have a thing for roof tops. Hooked up with my regular who I’m always
questioning if I should hook up with again. I’ve written about him before. Latino bear daddy type. Its just I have a thing for daddy types sometimes… so we arranged to meet at his place, he said he had a family thing to go to beforehand but I was like no worries I can hang at the bar if you’re running late. Got to the bar and he texted that he was gonna be late and that I could meet him at his family thing if I wanted (oh yeah forgot to mention the reason I’m always questioning this guy is he is a bit much, he wants way more than a hook up… borders on obsessive... however he is a really good fuck). I said no I would hang at the bar. Waited for a very long time…. Annoyed and about to leave but then he showed up.

His family was home when we got to his apartment, which is awkward, so we went up to his roof top. This made the wait worth it. It’s a nice summer night. We drink some wine. He kisses me and plays with my nipples through my shirt, very hot. I unbutton his pants and kneel down in front of him. I take his cock into my mouth, he is already hard, I suck him off while he plays with my nipples through my shirt. He unbuttons my pants and fingers my clit. He puts his shirt on the ground and lays me down on top of it and pulls off my pants, i slip a condom over his dick, he drops his pants to his ankles and he pushes into me. The ground is way too uncomfortable so I stop him and get up. At this point he kicks off his pants and picks me up in his arms, i wrap my arms around his neck, my legs around his waist and he slides into me, fucks me standing – love it. Love that he is so big and strong and can fuck me like that. We fuck like that for a while. Then he carries me over to a bench that they have on the roof and I ride him for a while, i look up at the stars as we fuck. Shit so hot. I ride him til we both cum. I put my pants back on and we drink some more wine. We head back downstairs to his apartment.

We get to his room and he lays me on the bed and we start kissing and grinding. We strip again and he sucks me off and then starts tongueing my ass. He’s hard again and he turns me over and asks if he can fuck me there. This is not something I normally do but I’m in the mood (I’m also a little sore in front from previous hookups…). I say yeah but to go slow, he slips on a condom and rubs the tip of his cock against my asshole, until i'm wanting it, grinding back on him, then he slowly pushes in, fucking me slow at first then fast and hard until I can’t take it any more. I tell him to switch condoms and he fucks my pussy for what seems like forever until we both cum. I lie on top of him exhausted.

At some point I must have fallen asleep, I wake up and the sun is starting to come up, I don’t like to spend the night at my hookups, just a thing I have, however I’m still here… he's spooning me and i feel his cock against my ass, he’s hard, we grind for a while then I tell him to get a condom and he pushes inside me, fucks me slow and hard, I rub my clit as we fuck, he keeps fucking me then pulls out, takes of the condom and shoots all over my back.

I clean up and tell him i have to go, he offers to make breakfast, to call me a cab, all which i decline. i kiss him goodbye as i leave. The sun has just come up as i'm walking home, love early mornings especially after i've been fucked...

The Craigslist Hook Up

One of the least enjoyable aspects of the anonymous sex scene is what I refer to as the "setting up" stage. The moment when you're horny as all hell and you've exhausted the million different ways to fuck yourself with your favorite dildo and you're way overdue for someone else to be wielding a cock in your general direction. So you hop onto one of the sites - craigslist, adam4adam, manhunt, etc. Some sites are more effective than others. I've tried all three of these with varying success.

Craigslist is a "you gotta work for it" kinda site. First there's the ad development phase. You have to decide how you want to describe your "trans-ness". Using terms like FTM, Trans Man, Trans Boy, has to be a deliberate choice, because each term draws a particular type of "gent". If you describe yourself as "FTM", you're more likely to draw a guy, for whom attraction for trans men has been tried, tested, and proven to be true. He can actually say "female to male" without tripping over words and looking seriously confused. This is my favorite kind of CL hook up because the sex is usually hot. If you describe yourself as a "Trans Boy", then expect the "daddy" types to hit you up. For some reason, the term "Trans Man" draws a lot more guys who are actually looking for trans women. Go figure.

Once the ad has been placed and the responses start trickling or rolling in, then the real work begins. Some men aren't scared to air their shit - they'll send cock pics right away, want to meet that day, and eagerly list all the many dirty things they'd like to do to you. Others are shy and hesitant. They're usually living a totally straight (and narrow) life with a girlfriend or wife, so every once in a while they gotta get a little kink in their life and that's where you come in. I generally steer clear of these guys, because, well...there's just too much potential for drama. Then there are the fools who, even after you've been clear about what being a trans guy means in your ad, you've emailed back and forth about this, they've seen your pictures (face and torso), they know about the facial hair, somehow after all this they're expecting (hoping and praying for) you to look more like a butch woman. I can tell you from experience, very rarely does meeting up with a guy like this result in sex (or even good sex). Once in a while, yes, a dude surprises the hell out of you and you walk away all glowing and shit, but most of the time, it results in nothing or nothing to write home about. You may have to wade through tons of responses from CL, a lot of them icky, and really only find one guy that you'd disrobe for, which is quite common, as well as time consuming! So, yeah, the CL hook up usually requires a lot of work.

he asked - when did you get your dick removed...

Met up with one of my regulars last night. He’s one I’m always questioning if I want to do again. And last nite kind of sucked... I got home in the early morn and was feeling like I needed something more. So I got on my sites to see what I could make happen. Made plans with a guy i had been chatting with for a bit for later that night. In the process got hit up by this guy who is in biking distance (I’m a real sucker for anything local) it was clear it was gonna be a quick thing he only had an hour and a half so i thought why not? So I hop on my bike and head over. Young looking guy says he’s 30 but looks ways younger, cute, latino, smooth, thin. I get there, its clearly a family home, kids toys around, etc.

he takes me to his room and the first thing i notice is the bunk bed.

he says that his little brother, who is six, shares his room. We chat for literally a minute and he pulls out his cock. I suck him off some, he asks me if i like his cock. we both strip, I slip a condom over him, he lies me down on the bottom bunk (fucking hilarious) pushes in side me and fucks me hard missionary style, he comes real fast, shoots inside me though which always turns me on.

Afterwards as I’m putting my clothes back on he asks when I had the surgery, I say what do you mean, he says yuh know when did you get your dick removed…. In my head I’m thinking what the fuck, but I just say patiently, cuz he doesn't say it in a shady way, I was born like this, i was born female and now i'm a guy. He just nods and say oh still looking a little confused. I finish getting dressed, we thank each other and I head out the door….