raw ass fucking

in my previous post transfag barebacking i wrote about how i was going through this period of doing a good amount of barebacking.  and to be honest it scared me a bit.  however writing that piece helped me to figure out what i wanted in a way that i could make safer choices.

i know there may be disapproval about this piece, but its a choice i made, definitely after some thought, it was not the safest choice and i'm not at all advocating it, but i own it as a decision i made at the time.  

so there is this dude i've been fucking for over a year now.  guy of color, round my age, bi but only fucks non trans women now except for me.  he's a real fucking asshole in alot of ways.  i would never date him, however he is a good to great fuck and very convenient. 

he says he's free of stds and i know he tests regularly for everything cuz he wants to be a sperm donor to make extra cash.  for better or worse i believe him. 

anyways, when we first started hookin up he asked if he could fuck my ass raw.  i said maybe after we've gotten to know each other a little better.  i don't know why i said that since at the time i had no intention of letting that happen.  actually to be honest i probably said it cuz i wanted to make sure he kept fucking me.  however so every once in a while he will check in.  "can i fuck ur ass raw now?".  i always say "not yet man". 

however, recently i decided that he is pretty safe given all of the above.  so he hit me up one night and i told him, i decided he could fuck me raw. 

and i really want it.  i want to feel a dude cum in my ass.  sorry to be crude but that's what i want.

i get to his place, we chat a bit then get to fucking.  i suck his cock til he's hard.  then i bend over, lube up my ass and he puts the tip of his cock to my hole.  he begins to push in.  i'm tight but he takes it slow until his cock pops into place.  then he begins to stroke me.  so hot.  we are both moaning and loving it.  he fucks me for a while and he says do you want me to cum.  i say yeah, but he says he's not even close.

he fucks me for a while more, but i can't take it anymore (i can last way longer with pussy fucking).  so he pulls out.  its a bit messy which is not so much my thing or his so he we both clean up.  it was however still very hot.

he's still hard.  he sits back on a chair and i kneel between his legs taking his cock into my mouth.  i suck him off while jerking myself off.  i cum hard his cock in my mouth.  i keep sucking him off til i feel him starting to cum.  i keep my mouth around his cock licking his tip as he shoots a huge load into my mouth. 

ass fisting

so i have fisted my share of pussy/front holes.  i luv it.  luv slipping a finger in, then two, then three until my entire hand is inside the person, feeling the walls contracting around my fist.  so hot.

however, i have never fisted ass before. 

that is until tonite.

so this dude hit me up.  attractive guy.  he wanted me to fist him.  i told him i had never fisted a dude before and was nervous about it.  he said no worries - he would show me.   cool.

i asked if he'd ever fisted a pussy before.  he said never.  i said cool, well yuh can fist me if you like.  it will be a first for both of us.

so i've fucked my share of dudes, but i was real nervous and unsure about this.  i just have never fisted an ass before.  so it took me a while to actually arrange the hook up.  i procrastinated for some time. 

even up until i was supposed to head over i was thinking if i should bail.  however, i've been feeling really bored with vanilla so i thought what the fuck, just do it.

so i get to his place.  fancy, upscale, apartment.  doorman.  i kind of hate having to deal with a doorman, as you never know if the name someone told you is real or not, and once i had an embarrassing moment with an over diligent doorman when the name i knew the guy by and the name he knew the guy by were different.  anyways, sorry not the point of this post. 

i get to his door and knock.  the door swings open and there is no one there.  weird.  i tentatively step in.  he's standing behind the door.  very weird.  he does not look anything like his pics.  way older and way less attractive - like seriously the pictures he posted must have been over two decades ago.  don't get me wrong a hot daddy type is a major turn on for me, however he is not what i would consider a hot daddy.  but i'm here so what the fuck lets just do this. 

big fancy apartment, a bit of a goth, dark feel to it he has porn on the tube.  literally the first thing he says is 'you ready to fist me'.  i haven't even taken my coat off or put down my bag.  not even a out of habit - hi.  normally this would be a major turn on for me but i'm already nervous.

i sit on the couch he says, let me go get clean for you.  cool, i wait as he heads into his bathroom.  he comes out a while later.  he doesn't offer so i ask for something to drink - he offers a soda - i ask if he has anything stronger, i have a feeling i'm going to need it.  he pours me a drink and we head to his room.

we strip and get to it.  no kissing or foreplay.  i just grab a glove and lube and begin slipping my fingers into his ass.  i have no idea what i'm doing.  and he's not helping me out so i just say tell me if its too much.  he says ok.  i slip my whole fucking fist into his ass.  its kind of amazing it feels very different than what i've experienced before, roomier actually, maybe i don't understand anatomy.  i stroke him a bit, carefully and he tells me to pull out.

he turns me around and begins fingering my ass and my clit.

i say i want to fuck you more.  he says ok.  i grab more lube and begin sliding my hand into his ass until my whole fist is inside him again.  i begin fucking him, this time i'm not being so careful, pumping my fist in and out, he's moaning and grinding on my fist, until he tells me to stop and pull out.  he gasps as my fist leaves his hole. 

then i say yuh wanna do me.  he says sure.  grabs a glove and slips two fingers in my pussy, then three, then four, he trys to fist me but i can't take it, his hands too big.  he finger fucks me for a while until i'm sore and ask him to stop.  he asks if he can paddle my ass, normally i would have gone for it but i'm not sure i'm that into this.  i say no.  he says he's tired and needs to stop which is cool with me. 

i go to his bathroom to clean up but his showers messed up so i clean up the best i can.  i come back and we chat some about our lives, what we do, family, etc. as i finish my drink and put my clothes back on.  its always interesting to me when some of the kinkier dudes have serious coat and tie straight lace jobs. 

then i thank him and head out the door my ass and cunt still slick

my first fireman

who knew?  so i always thought the gay male obsession with firemen was some kind of stereotypical gay boy thing (i do understand this obsession with firemen crosses many genders - lol).  yuh know i've always resisted the obsession some have with law enforcement, firemen, etc.  i am not a fan of the police.  however today i did my first fireman and i do have to say, i mean maybe it was just this dude, but there is something about firemen that is unbelievably hot.

so this guy had actually hit me up in the past but in his pic he kind of looked like a serial killer so i never responded.  he hit me up again recently and he had some new pics.  in these pics he didn't look like a serial killer, he actually looked pretty hot.  so i thought why not, maybe he's not a serial killer (sometimes i'm so ridiculous), and we started chatting.

guy of color, he's been with trans guys before, identifies as bi. wants to fuck all my holes.  hot chats.

so it took a bit to arrange but we finally set a date.  i get to his place.  he looks at least a decade older than his pics, which is hot, what i find attractive is all over the map and changes frequently, but i do have a thing for a hot daddy.  sometimes i want to give people pic advice.  like this dude looks way hotter in person, as his real age, i actually think it does him a disservice to post those pics from a decade ago, however i get all the ugly ageism of the hook up world.

so we are doing the usual pre fuck chat.  he did all the work in his apartment, its a really nice place, he's clearly very proud of it. we are sitting on his couch he leans over and kisses me.  he pulls back and say come here.  i climb on top of him and we kiss and grind.  he unbuttons my shirt and sucks my nipples.  then he puts his hands under my arms and lifts me up off his lap so i'm standing in front of him.  i reach for his shirt but he pushes my hand away. he unbuttons my pants, pulls off my boxers so i'm standing there naked.  sometimes i can be self conscious about how i look naked like that, but he sits back and just looks at me, clearly liking what he sees.  then he leans in and begins kissing my stomache, my chest.  i reach down and pull of his shirt.  he stands up i unbutton his pants and go to work on his cock for a while.  then he leans down, picks me up, i wrap my legs around his waist and he carries me like that to his bedroom.  i love how strong this guy is. 

he lays back on the bed and says 'i wanna taste you'.  i straddle his face, he's good, blows me til i can't take it anymore, i pull away, he says what's wrong, i say nothing its too much, i can't take it anymore.  yes you can he says and pulls me back.  he goes at me some more and won't let me go, i'm writhing and squirming until i really can't anymore and tell him he really needs to stop.  he lets me up and i crawl down to his cock.  he has a mirror at the head of his bed so i watch as i blow him.  very hot.  i'm really turned on.  i really want him to fuck me.  condom, i ask he nods towards the nightstand.  i grab one and slip it on him lube him up and guide him into me.  i go slow as he's big and its been a couple days since i've been fucked.  he says when were you last fucked - i say about a week ago as his cock slides into place.  i ride him for a while then he sits up and i wrap my legs and arms around him, he stands up and he fucks me standing - this dude is so incredibly strong. 

we fucked for nearly 3 hours so i'm not gonna give a blow by blow account.  suffice to say many positions, rough and hard, very hot.  he kept picking me up and moving me where he wanted me, this is i think what i love about firemen, i mean i've been with muscular guys, strong guys, but there is something about someone who is used to throwing heavy things over his shoulder on a daily basis, who's life depends on doing so, that is very hot.

towards the end he asked if he could fuck my ass.  this is not usually my thing however i'm very turned on and i can see he really wants it, so i say you have to go very slow, he says i can be gentle.  he lubes up, i get on my knees, he puts the tip of his cock to my ass.  he slowly pushes in, takes it real slow, gentle strokes til i start fucking him back, then he's fucking me hard, fucks my ass for a while, he says, 'you wanna be my boy', 'im gonna make you my boy' over and over, hot, i start to feel like i can't any more, i start to pull away and he says what's wrong.  i say nothing i just can't anymore.  he says i'm not hurting you am i.  i say no its just too much.

he says you can do more and lifts me up and turns me on my back, he's lying on top of me kissing me, he pushes my legs up and puts his cock to my ass again.  he pushes in slowly, inch by inch, stopping and letting my ass get used to his cock before pushing in more, he's kissing me as he does it, saying 'i'm gonna make you my boy, no one's gonna hurt you boy, you can do it'.  its kind of sweet and gentle and hot at the same time.  he's really good and takes it so slow that he's able to get his cock all the way inside me.  i've done anal before but this guy has a huge cock...  'see boy, no one's gonna hurt you, my cocks all up in you, do you want me to stroke you or just hold like this'  hold i say and it just feels amazing his cocks huge and filling my ass.  then i begin to move against him.  he moans and begins stroking me slowly.  after a bit i feel like i can't anymore, i can't i say, he says 'its ok boy, yes you can and he stops stroking and just holds inside me until i'm ready again.  its so hot.  we fuck like this for a while.  he's such a daddy dom, pushing my limits, yet so gentle and sweet, it was pretty incredible.

afterwards, i shower and he's such a sweetie, i have a real thing for those masculine, muscular guys who are also such gentle sweet hearts.  i'm drying off and he says, here let me get your back and drys me off.  such a sweetie.

we are chatting some as i'm leaving.  he's shirtless and i run my hand down his chest.  he thinks i'm looking at a scar that starts on his side and goes across his back, i'm not, but he tells me that he's actually on leave from work right now cuz there was an accident at work, i'm thinking shit that was some major accident, he says he's supposed to take a cardio test next week and if he passes he'll go back.  then he says, with a wink, but i think this was enough of a test and i passed.  i say, thank god you passed, i'm thinking what the fuck what if he'd gone into cardiac arrest or something while we were fucking.  like he knows what i'm thinking he laughs, yeah, that would have sucked if you had to call 911 or something.  i'm thinking seriously dude, wtf.

anyways i kiss him good bye.  possible 911 call and all i now have a thing for firemen.

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...