holiday fuck

i was out of town visiting fam for the holiday.  i was getting hit up alot on all the sites - a wide variety of cuties.  however, i'm here to spend time with my family who i don't see often and it doesn't feel right to leave them alone while i go fuck some dudes.  i am in town for nearly two weeks though so i figure i'll give myself one day to play.  i decide on this one dude because he is interesting, into bdsm, lots of tats, brown skin, just a little taller than me so not a big guy but very cute.

however he is very, very persistent which is a flag for me, not always but often in my experience overly persistent guys either want more than just a fuck i.e. become stalkerish and/or want to be your husband after the first meet up or are desperate for a fuck for a wide range for reasons....(no judgement, just not my thing) but there is something about this particular guy that intrigues me.

we chat on and off for a few days.  i will be his first trans guy.  even though getting to him will be a trek i decide to go for it over closer options.    the day arrives when we have arranged to meet.  i tell my family i'm meeting a friend and head for the bus.  i'm still feeling unsure and nervous about this hook up.  i know that its largely because i'm not on my home turf so feel off my game.  there is also something about his look that is borderline hot/serial killer...  i mean he is very nice but aren't most serial killers nice at the start?  he offers to pick me up repeatedly which i decline, i always feel safer being able to get to a hookup on my own.  he seems to sense my uncertainty suggesting i take a picture of his home and text it to someone when i get there.  which actually makes me more nervous in some kind of weird way i.e. maybe this means i definitely should be nervous.

however i decide to proceed.  its a long bus ride and the bus stop is a bit of a trek to his place, i stop and pick up some beers on the walk.  i finally get there and his home reassures me, for some reason i was picturing a small house, with an empty yard and one car in the front, i don't know why that says serial killer to me...  but instead its a small home with no real yard, a kayak hanging in the garage, a couple cars in front (turns out he has a roomie), a mountain bike chained to the fence.

he lets me into his place which is neat and clean (a thing i have) and has a really nice view.  he is cuter than his pics in person.  he says his roomie is home but doesn't care.  i tell him i brought some beers to which he says he does not drink.  i immediately feel like an ass, i usually ask guys before i bring beer, so much of our communities are in recovery and all.  i apologize and say i don't need to drink and start to put the beer away.  but he say's no its cool, he has been in recovery for a while and doesn't have cravings anymore and he wants me to be comfortable.  he cracks one open and hands it to me.

i take a few sips.  he says you are so cute and sexy and runs his hands down my back.  i smile and put the beer down.  we start making out and he is a very good kisser.  i pull off his shirt and take off mine.  he has the most incredible six pack i have ever seen.  i lie back on the bed and he lies on top of me kissing and grinding.  he starts to suck my nipples which is always an immediate turn on for me.   i reach down for his belt, undue his jeans and stroke his sizable cock through his briefs.  he's hard.  i push him back and we both strip.  i lie back on his bed buck naked.  he says 'you are so hot' as he looks down at me.

i sit up and take his hard thickness in my mouth.  my tongue sliding up and down his length, my lips wrapped around his head.  he groans.  i go at him for a bit then he stops me and asks if he can give me a massage.  nice.  he turns me onto my back and begins to rub oil down my back, ass, legs, his sizable hands kneading my shoulders and moving down.  then he turns me over and begins kissing my nipples and moves down between my legs.  he licks at my clit with the tip of his tongue.  asks if its ok, i tell him to do it a bit lighter, which he does and it feels fucking amazing.  his tongue slides up and down the length of me repeatedly, slipping in and out of me.  i'm very wet and at this point i want more.

i stop him and ask if he has a condom.  he grabs one out of his dresser and puts it on the bed, but then pushes me back plunging his head between my legs.  i just can't get enough he says as his tongue circles my clit.  finally i really can't take anymore and i push him onto his back, grab the condom and slip it on.  then i mount him, slowly as he is a good size, i slide slowly down his cock until he is deep inside me.  we both moan.  i ride him taking the full length of him then pull him on top of me and he fucks me deep, his hips pounding between my legs our bodies rubbing tightly together my legs entwined with his.  we fuck hard and fast, i grab his ass pushing him deep with each stroke.  then he sits up so he's kneeling and can watch his cock sliding in and out of me.  he reaches over and grabs a vibrator from his dresser and places its tip on my clit as he fucks me.  the thrusting of his cock and the vibrations on my clit are bringing me very close.

then he pulls me over so i'm riding him again.  our bodies are slick with the massage oil.  i ride him slow at first, feeling his thickness, then faster, my clit sliding against him as i ride, until i cum collapsing on top of him.  he is still hard as a rock however, but he pulls out and wraps me in a spoon.   we rest for a bit and i look up and realize i've been there over two hours at this point and i need to go.  he says you have to go huh?  i say yeah, but you haven't even cum.  he says no worries, it was more than hot.

i feel a bit bad but not enough to be late to meet my fam so we both clean up.  he insists on at least driving me part of the way which i accept.  on the way we chat he is a really nice guy but i realize that my initial instincts were somewhat right on.  if i actually lived here i think he would have already had boyfriend visions in his head.  however this was definitely a hot fuck.  he drops me off and we part with a quick kiss.  

quickie

i was out of town visiting family.  i had just finished working out at the local gym.  it was about 7am or so.  i logged onto scruff cuz there is a starbucks next to the gym re:  free wifi.  this dude i had been chatting with hit me up.  i said well i'm just leaving the gym but if your up for a quickie i'm game, where yuh at?  he sent me his address and he was very close by.  i said i can head over now if you like, do you have condoms?  he said no do you?  But don't worry i'm hiv negative.  i said no i don't have one (i was just going to the gym not expecting play....) and safe only.  he says let me look.  his next message says, ok found one.  cool i say.  i'll head over.

he says i want you to come in, get on your knees, suck me off hard and then bend over and let me fuck you from behind with your clothes still on.  then i want to pull out and cum on your asshole.  i say all cool, but you can cum on my back.

i head over, get a bit lost on the way but it really takes less than five minute.  i knock and he lets me in.  his cock is already out and he's stroking it.  its dark in his living room. i say are you the only one home?  he says no.  i take off my hoodie and drape it over a chair.  get on my knees and take his cock into my mouth.  i suck him off good and hard.  to be honest i barely looked at the dude.  i vaguely remember from his profile that he's a cute 20's something bearded type.  after a bit i pull back he's erect but not as hard as i prefer but i'm ready to be fucked.

he picks up a condom, lubes up.  i turn around, drop my gym shorts and briefs down to my knees and bend over his couch.  he pushes into me doggy style.  fucks me hard and fast.  i grunt and moan as i take his cock.  after a bit he pulls out.   strips off the condom and begins jerking off.  i do the same.  stroking my clit as he strokes his dick.  as i feel his cum spurt on my back i begin to cum.  he shoots a huge, huge load all over me.  when we are both done he says don't move.  his cum is dripping all over me, down my back, onto my ass.  he grabs a towel, wipes me up, somewhat.  i pull up my gym shorts his cum making the fabric stick to my legs.  thank him and head out the door.  hop back in the family car and head home for a shower. 

finger fucking

I really liked fingering her.

It was the way she'd grab me and squeeze, her wetness coating my finger as I stroked. I loved the way her body would buckle when my finger curled inside her, rubbing a spot that'd make her moan and scream. She came faster and more often than any one I'd ever fucked. The first time we made out, we were chilling on my sofa, sexual tension in the air so thick. I could tell she wanted me to make the move and I'm usually the trepidatious one when it comes to first moves.
"Can I kiss you?" I finally asked.
"Don't you mean may I?" Yes, yes, she'd been giving me sexy snarkiness all night. Her brand of flirtatiousness I guess.

She was all tongue when we kissed and I loved it. The longer we kissed the more turned on I got, like I was falling into some lust-ridden ocean. Have you ever experienced that? A lust that just deepens and deepens till it feels way bigger than you and the other person (or persons) creating it? Before I knew it her tank was down to her waist. Her hands were up my A-shirt. We were twisting our bodies to fit in that couch, not noticing how uncomfortably cramped it was because we just wanted to get closer and closer.

My hand crept up her bare thigh to her wet panties and I played on the outside of her, enjoying the feel of her moisture soaked underwear and her pussy beneath. She felt hot under there and I wanted to slip my finger through the fabric and into her. Instead I held back and slowly circled her hard clit, which I could feel. She sighed into my mouth, her tongue working mine more vigorously, her hand around my neck, craning to bring me closer to her if that was even possible given how physically wrapped around each other we already were. Eventually she stood up, took my arm and dragged-pulled me into my dimly lit bedroom. She was not shy, this one. She pushed me onto my bed, straddled me and slowly took off her tank and sports bra. I tried to sit up because I really wanted to lick and suck her nipples, but she held me down and roughly pulled off my a-shirt. Then she placed both hands on my chest, moved her skirt out of the way and ground her hot and wet panty-ed crotch on mine. She moved like she knew what the fuck she was doing. My hands wrapped around her round ass and squeezed, grinding her hard, internally cursing the shorts and boxers barrier between our bare pussies. I wanted to feel her but I wanted her to decide when. Eventually she grabbed my shoulders and did this hot flip over thing and then I was on top and she pulled my head down to her chest. I hungrily lapped and sucked and encircled with my tongue, alternating between nipples.

At first I was gentle, but her sighs and moans and groans got me hungrier so I bit hard on a nipple.
She emitted a "yes..." while her legs curled underneath me. I spread them, moved her panties to one side with my fingers and my god she was so fucking wet.

"You're so fucking wet," I said into her breast where my mouth was still planted, kissing and licking while my middle finger parted her pussy and plunged into her quickly, making her buckle and twist and utter unintelligibles. I wanted her bad. This wasn't going to be no slow n' gentle finger fucking. As I fucked her I licked and bit my way from her breasts up her neck to her open mouth and her tongue was ready. I sucked that too. She reciprocated with mine. Our mouths clasped and wouldn't let go. Down below, my middle finger was curling and uncurling, gently twisting, roughly going in and out. Our mouths unclasped.

"Oh god...," she muttered
"You like that?"
"Yes...god." I slipped in another finger which made for an even tighter fit.
"You like me fucking your pussy?" I was whispering into her ear and she must have liked that because I felt more wetness on my fingers and hand.
"Yes...oh god...don't stop. I'm gonna..." Her body did the buckling and winding thing beneath me. Her hands around me tightly. Suddenly I wanted to see my what my fingers were doing. I wanted to see her pussy swallow them in. So I moved down her stomach, kissing and licking on my way down and the sight that awaited me was just...

I wanted to fuck her deeper. Normally my strap-on cock would have made an appearance, but she just felt so damn good on my fingers. I lifted and bent one of her legs 90 degrees style, which opened her more and I slipped in deeper. The way her pussy would grab me was heaven. The wetness, the sounds as I slipped in and out, all of this just drove me wild.
"I could fuck you all night," and I meant it. Just as I said that she tightened around me. I didn't think she could get any tighter and I felt her orgasm start building, so I moved faster. Feeling every surface of her, curling and flicking my fingers inside her. She got really loud as she came and her body arched off the bed and damn what a beautiful sight. When she came down from that, she pulled me to her and held me in a tight embrace.

A few minutes later, I still lay on top of her. We kissed softly and gently, over and over and over. No tongue. Just wet lips clasping and unclasping, making loud suction sounds, hmm-ing from time to time. Then her hands wrapped around my shoulder, the kisses grew more urgent, her legs parted and my hand started sliding down...

just a good fuck

dude had hit me up on line the day before but i wasn't free.  twink of color.  twinks are usually not my type but he has a huge cock and that's what i happen to be looking for at the moment.  he has never been with a trans guy before.  we arrange to meet up.  he is mad late which is annoying.  he shows up and he is actually not twinkish at all.  big tall corn fed type.  not skinny, not muscular, not big or bearish.  very hot.  very much my type.  he's also incredibly smooth which i'm starting to realize is my preference.

we chat a bit over a beer then get to it.  we kiss our clothes still on. he's a good kisser.  i pull off his shirt and take of mine.  we kiss and grind just feeling each other's bodies.  i kneel down between his legs and unbutton his jeans pulling out his sizable cock.  i put him in my mouth and blow him.  he's big but for some reason i'm able to deep throat him which is very hot.  usually i can only deep throat with smaller guys.

i pull back and take of his jeans.  i strip and lie back on the bed.  he sucks my nipples and plays with my clit. then he spreads my legs and kneels down between them.  i feel his tongue on my clit, stroking it, then i feel his tongue inside me, as he licks the full length of me.  he seems like he could do this for a while but i can only take so much.  i stop him and push him onto his back.

i blow him a bit but he's fully hard and clearly ready.  i grab a condom (magnum xl) slip it on him, lube him up and put his tip to my hole.  i take it slow as he is big.  easing him into me until i can take the full length then i ride him.  as i ride him he moans and say my name.  hot.

so this was a very long session - it lasted 2 and half hours thus i can only give highlights.

he is kneeling between my legs, stroking me slow and steady, i can feel an orgasm building, nothing is touching my clit, the size of his cock and the angle of his fuck are making me cum.  he keeps stroking me as my body starts to tighten, i moan and grab his arms, his cock plunging in and out of me, so thick its stimulating my clit, i have never cum like this before, i throw my head back my eyes closed and cum hard

he is in a seated position and i'm riding him.  i'm fucking the full length of him, slamming my body onto his cock hard and fast and he's raising his hips to meet me.  its hard and loud and the bed threatens to break as we fuck each other.

he turns me over onto my hands and knees.  pushes the head of his cock into me.  slowly just the head at first.  then he begins stroking me slow i look back see him watching his cock slide in and out of me sometimes just the tip other times giving me his full length.  like he's exploring different ways to fill me.

we literally fucked for about 2 and a half hours non stop. towards the end i told him i couldn't do anymore.  he stripped off the condom and i blew him a bit then he jerked off,  stroking himself while playing with my clit.  blows his load on my chest.

a daddy fuck

it was about 11pm.  i had just gotten home after a party which i left early.  i was feeling a bit down.  not a good reason to go on a hook up but it is what it is.  i know that sometimes i use hookups as an escape mechanism.  gotta write a piece about that.

i get on the sites and immediately this guy who i had chatted with before hit me up.  he has a nice body lots of tats which i'm into but is only somewhat attractive to me.  however he lives a few blocks away so i decide to go for it.

i grab my supplies and a few beers and head over to his place.  he is older than he looks in his pics still only somewhat attractive to me.  he has this old, latin daddy thug type thing going though that is a bit of a turn on.  we open the beers.  i take a drink and he pulls me towards him.  starts kissing me and feeling my body.  i put the beer down.  no prefuck chat needed here.  he says you are so hot.  you look just like a little boy.  he unbuttons his khakis.  i kneel down.  he says 'suck daddy's cock boy'.  i take him into my mouth.  he is already hard.  sizable and uncut.  i go at him.  he grabs my head with his hands guiding my strokes.  i try to deep throat him but he's too big.

i pull back and go to my bag for condoms and lube.  i slip a condom on him and lube him up.  he bends me over his couch, spreads my legs and pushes into me.  i slow him down as he is big and i need to get used to him.  when i'm ready i push back hard and he starts to pound me.  hands on my hips fucking me hard his balls smacking into my clit as he fucks me.  this goes on for quite sometime, hard, rough fucking.  then i stop him and lie back on his couch.  he mounts me slides his dick into me  and pounds his hips between my legs.  he says 'you like daddy's cock boy?'  as he's fucking me.

then he turns me over onto my stomach and push his cock into me from behind.  grinding into me, my face smashed into his couch, he plays with my clit as he fucks me and i cum hard.

i pull him down onto the couch and get on top of him.  i slide down his cock and ride him.  i tighten around his cock on each upward stroke.  he moans 'yeah boy'.  i fuck him hard and fast til he cums, shooting a huge load inside me.

i slip off him, ask to use his bathroom, pee, dress, grab my stuff, thank him and kiss him goodbye.  he tells me to text him so he know's i got home ok.

Grins

i've been going through a bit of a hookup slump.  the kind of slump where i'm just not sure what i'm looking for alot of the time.  case in point this friday nite.  i am an introvert.  this means that i need to make sure i have an adequate amount of alone time.  the last few weeks were full of alot of socializing  as a result i had not had enough alone time and was very grouchy.  friday nite i had no plans except to spend time with myself.  however at some point i started to feel a bit horny.  like i wanted to do a hookup.

i had not done one in a very long time, at least a few weeks.  i pondered hitting up one of my regulars but i was not feeling like anything long or involved.  all my regulars right now are not short fucks.  they are nice guys and we often chat a bit before they proceed to fuck me for hours.  so i got on the sites to see what was happening.  again i just was not sure what i wanted and was also having a very slow nite.  after not many hits and none of them interesting i called it a nite.

the next day i decided to post an ad on craigs list which i have not done in a very very long time.  CL just tends to feel like more work than the sites and i am lazy.  in my ad i said i wanted something short and sweet.  fuck me then leave.  that's it.  surprisingly right away i got a good number of interesting responses.  in the past this has never happened to me before.

a thick well endowed tatted and muscled dude, a clean cut young guy, a 'straight' guy, and a scruffy type were my top choices.  as usual my indecisiveness kicked in and i couldn't decide which one i wanted to do.  i decided to go with the first one who hit me up - the thick well endowed tatted dude for no real reason except that he hit me up first -lol.

we arranged a meet up for the afternoon.  dude came over and was cute and muscled like his pics and definitely well endowed.  he fucked me for a bit but then he couldn't keep it up.  instead he sucked me off and finger fucked me then i blew him.  all good but i was really looking for a fuck...

dude left and i was still horny.  i had been chatting with someone that morning on one of the sites who lives a block away.  however i had not pursued it as i already was having trouble making a decision.  but now i'm horny and frustrated.  i get on line and he's there.  small, skinny, young asian guy.  i'm not usually into younger nor into ultra skinny however he is a block away and i'm horny.  we start chatting, he says he's gotta head out soon, so we decide on a quicky and he heads over.  only thing is that he's never done a trans guys before wants to but is nervous/unsure.  so this could go either way.

he's there in five minutes, cuter that his pics.  we chat a bit and then start making out.  we're kissing and grinding. he's on top of me and i can feel his hard on through his jeans.  its very hot.  we have surprising sexual chemistry like i have not had with someone in a while.  yuh know when you both are just into each other's bodies, each other's vibe.  we strip and make out some more then we look at each other and grin.  which thinking back on it is kind of funny, we're both looking at each other naked with silly grins on our faces - we just couldn't help it.

i blow him for a bit, he's got a nice average size cock, i like a wide range of cock sizes.  he plays with my nipples while i blow him.  i grab a condom slip it on and ride him.  we're both moaning our bodies grinding.  again we look at each other and grin...  he flips me over and fucks me missionary style which is my fav.  i raise my hips to meet each stroke and he moans.  he pulls back, puts my legs on his shoulders and fucks me fast and hard.  i pull him back on top of me, grab his ass and raise my hips fucking him til i cum.

then he turns me over on my hands and knees and fucks me doggy.  fast strokes our bodies smacking against each other.  he says i'm gonna make him cum.  i say go right ahead man.  he fucks faster and moans as he shoots inside me.

we both collapse on the bed.  he rolls off me and we both turn to each other and grin.  we chat a bit but i know he's gotta go.  as he's leaving we do the usual lets do it again maybe chat and laugh as we realize we have not even exchanged names.

i couldn't get it in

this has never happened to me before.  i just did this hook up and i couldn't get it in.  i've done some big dudes before - the giant cock, Mr Thick, to name a few.  however i've never come across one that i really could not get in at all.

on a side note, i used to think that i knew my limits for example, there is one dude i had been chatting with who is fourteen inches and i don't think he is exaggerating.  i was gonna give it a go however i found out he was also thicker than a beer can so i got scared and didn't pursue it.

however with this dude we had been chatting on and off for some time but our schedules had not lined up, i knew he was a good size but really had no idea...

one morning i unexpectedly had the day off work and i woke up extra horny.  i got online to see what i could make happen.  i had a few dudes pending when this guy hit me up.  dark skinned skinny guy and he was ready to come over right away so i said yeah lets make it happen.

dude came over.  not a talker at all.  i'm used to a little pre fuck chat but he barely said two words.  no problem on my end.  i just want to get fucked.  he lies back on the bed and i run my hand up his thigh.  i feel his sizable cock through his jeans.  he is not even hard yet.  we kiss and make out some.  i pull of his shirt and unbutton his fly.  he pulls off his jeans and i realize he is huge.  long and ridiculously thick.    i suck him off the best i can which is not that great so i kind of give up.

then i try to slip a magnum on him.  i feel bad as i do it as it just looks like its squeezing his dick in a way that must be incredible painful.  however again he doesn't say anything. i push him onto his back and i try to get him into me but i can't.  this has never happened before.

he turns me over so i'm on my hand and knees and he fucks me for a bit, just the tip, that's all he can get in and even that is actually painful.  finally we give up.

i lie back and he finger fucks me, then he says he wants to taste me and blows me til i cum.  he however has not cum.  i suck him off some but i know i'm not doing it as i can barely wrap my mouth around him and i can only go so long...  i jerk him off some instead for a bit but then he says its ok he has to go anyways.  i don't take it personally figure if he wanted to cum he could always jerk himself off.

damn first cock i couldn't do...

virgin play

This guy and i had been chatting on and off on one of the sites for a while.  i want to say its been six months or so.  He's very cute in his pics.  Short, thin white dude, a bit of a hipster look.  He is gay, only fucks non-trans dudes, he says he's never done a trans guy.

he also says he's not into hook ups he is more of the dating type.  i'm thinking why are you looking for dates on this site, but from the start i am clear i'm NSA but luv a good fuck bud.  this is good with him so we kept chatting and arrange a date to meet.

dude gets to my place and he has this nerdy awkward thing going which i like.  we sit and chat on my couch for a bit.  usual prefuck chat.  at one point i'm talking about my current NSA/non dating place in my life and he says 'you mean this is not a date?'.  i kind of laugh thinking he's joking but then realize maybe he's not and i say 'no its not'.  he pauses for a second and then just says ok.  whatever... i was clear with dude from the get about the situation if he chose not to listen its not my issue.

we move on from that awkward moment to a bit more awkwardness as conversation wanes and its clear someone is going to have to make a move.  he is very nervous and its seems i'm gonna have to be the one so i lean in and we start kissing and making out.  i tell him we should go to my bedroom.

we kiss and make out some more.  i pull off his shirt and pants and take off mine.  he is hard and i bend down and take him into my mouth.  he groans.  i reach for a condom, slip it on and lube him up.  he climbs on top of me, spreads my legs and after a moment of hesitation pushes into me.  hot.  missionary is my favorite.  he strokes me slowly, moaning, then harder and faster til he cums.  its good, not incredible but good.

afterwards he admits that while he dated a woman once they didn't fuck.  i've fucked dudes before who have never fucked a pussy/front hole but they usually admit it to me ahead of time.

as we are lying back in that post fuck stupor he asks if he can see me gesturing towards my crotch.  i laugh and say of course.  i spread my legs and he reaches down and frees my cock.  he says 'wow' and has this look of amazement and wonder on his face like its the most incredible thing he has ever seen.  he says 'wow it looks like a tiny dick' i laugh out loud cuz he looks exactly like a little kid in a candy store. he asks if he can touch it.  i say of course.  he begins to stroke me and jerk me off the whole time with this look of wonderment and amazement on his face.  its quite cute.  i lay back and let him jerk me off til i cum again.

the musician

just did another hook up with a new guy.  this is the third time we've hooked up.  tall, beautiful, dark skinned dude with locks.  he is a musician by trade.  classical music.  nice guy. closeted.  i'm the first trans guy he has hooked up with, at least that he know's of.  identifies as bi.  the first two times we hooked up he was really nervous.  we chatted for a long time and then i had to make the first move.  at this point in my hook up history i'm used to nervous guys so don't mind it, though i prefer dom guys and/or confident take the lead dudes.

this third time i figured he would have gotten over the nervousness.  not the case.  we chatted about what was going on in our lives for a while and i started to feel impatient.  so again made the first move.  again with his nervouseness....  however we moved onto fucking.

we kiss and make out our clothes still on.  he is an ok kisser.  kissing well is a skill.  i pull his shirt off and take off mine and we make out topless for a bit.  i can feel his hard on through his jeans which i quickly unbutton.  we both strip.  he is hard as a rock.  he has a very thick sizable cock.  nice.  i have not done a big cock in a while and have been craving it.  he climbs on top of me and sucks my nipples, his erect dick brushes my thigh as i moan.  i push him onto his back and take him into my mouth.  he is big and thick so i do my best sucking mostly just the first half.  i grab a condom and lube him up.  i slowly lower myself onto his cock.  i take it real slow as i'm tight.  its been a while since something this big has been inside me.  i ride just the first half for a bit then slowly slide down his full length.  i moan as his cock pops into place and just hold still for a minute feeling him deep.  then i ride him, slowly, sliding up and down his thickness, he moans.  then i'm grinding against him harder.  its a little painful due to his size but i want it.

i pull him on top of me and he fucks me missionary.   his hips pounding between my legs.  at one point he puts my legs on his shoulders and pushes into me deep, but its too much and i push him back. he apologizes and stops, but i shake my head and pull him back into me at a different angle.  i luv missionary but realize missionary is not everyone's strength.... i push him onto his back and ride him.  i tighten myself around his cock on every up stroke.  he moans.  i ride him harder and faster and he groans.  says he's close.  shoots a huge load inside me.

he pulls out and then immediately starts sucking my nipples and playing with my clit.  i'm good but can always cum again.  then he slips his fingers inside my wet cunt.  i moan as he strokes me, finger fucking me slowly while sucking my nipples, his fingers are deep in me and he strokes me until i cum again.  i lie back exhausted.  he runs his fingertips up and down my chest slowly - just enjoying the feel of my body.  it feels amazing til we both doze off.

a tale of two cocks

So I don't usually write about my regulars. Just a thing I have. However this just felt like a tale that needed to be told.

I had told one of my regulars i would swing by his place after i had dinner with a friend. this regular is not one of my favs but he is convenient, usually available and a decent to hot fuck.  Guy of color, bi but mostly fucks non trans girls.  Sometimes he just wants a blow job though which usually is not something i do, i like to get fucked, however once i agreed to it and it was actually very hot - it involved a workout machine...

anyways i was in the mood for whatever this particular night, so i told him i was up to fuck or just suck. up to him. here is an account of my night

8:45 pm finished dinner with a friend. texted blowjob (bj) boy to say i was heading over and would be there in 20

8:50 pm on my way over to bj boy's place got a text from a regular, a fav, guy of color, beautiful, sexy dude, we have hot, sensual, amazing sex but hook up infrequently due to both our living situations. he says he can host til round midnight. i would much rather hook up with my fav but don't want to be an asshole and cancel on bj boy. so i tell my fav i can't.

9:05 pm i get to bj boys place. we chat a bit.

9:10 pm he starts to strip. i follow suit. he climbs on the bed and lays back. i kneel between his legs and take his cock into my mouth and begin sucking him off. i know how he likes it, tight, lots of suction. he's hard and i take him down my throat, throat fucking him.

9:20 pm he says he's gonna cum, this is unusually fast for him, i mean he's fucked me non stop for over an hour before, but it is what it is, i let him shoot into my mouth, not normally something i do, but i do it with him, we've been playing around for over a year so there are some things i do with him that i don't with anyone else

9:22 pm after i've cleaned up some, i ask him if he minds if i jerk off. i reach down and stroke my clit, i'm not very turned on, its not very hot, he just sits there, doesn't really watch, it turns me on to have a guy watch me jerk off if it turns him on - this can be very hot, this present situation is not hot, i barely cum.

9:30 pm we chat some as i am getting dressed. i want to leave but he's chattie. however i am ready to go

9:45 pm i'm at the bus stop waiting for the bus feeling very unsatisfied and i decide to see if my sensual fav is still free so i text him saying i could be there in about an hour

10:05 pm the bus finally arrives, i have not heard from sensual fav so figure its a no go

10:15 pm sensual fav texts and says sorry but he's not at home anymore. oh well, i continue on my journey home

10:35 pm i'm at the store near my place picking up some snacks when my cell rings. its sensual fav. he says he can head home now and meet me at his place. i say its gonna take me at least 20 to 30 mins to get there. he says no worries he should have the place to himself til at least 12:30. i say cool lets do it.

10:37 pm i hop back on the bus. i throw some gum into my mouth - i figure its the least i can do given i just blew a guy less than an hour ago.

11:05 pm i get to sensual favs place. we strip immediately and kiss. he's a really good kisser. we move to his bed. he lays back and we kiss and grind. i suck his nipples and lick my way down to his cock. i take his cock into my mouth and stroke him, my lips around him, taking him slowly down my throat. he groans. i go at him for a while until he pulls me back on top of him.

we kiss and grind. he pushes me onto my back and sucks my nipples his lips moving up and down my body. he spreads my legs and begins tongueing my clit. stroking it just right until i can't take it. i pull him up on top of me. he rubs his head against my clit. he's very hard. i slip a condom over his cock and he pushes into me. we both groan. he says, you feel so good. he's stroking me missionary style, our bodies close and tight, slow then hard and fast. after a while he says he's close.

he pulls out and spreads my legs and goes at my clit with his tongue. i throw my head back, enjoying it, my body shakes, i clutch the sheets my body tight and cum hard. i pull him back on top and into me. he's fucking me deep, we are holding each other close, stroking, our bodies intertwined, he cums hard shooting into me.

11:50pm he gets up to clean off. i'm lying on my stomach, worn out. he sits beside me and runs his fingers up and down my back.

12:00am i get up, shower, put my clothes back on, kiss him good bye and head out the door

cock before dinner with the fam - a tale of hometown play

So I did my first out of town hook up today. I’m visiting relatives in the town where I grew up. When I had visited in the past by the end of the visit I would be near explosion with sexual frustration. So I had decided ahead of time that I would see if I could arrange something for this visit. A week or two beforehand I added to my profiles that I would be in my hometown and the dates of my visit and then I changed my location to that city. I got hit up pretty quickly by a cute guy who had been with a trans guy once before and was not far from where I would be staying. We chatted for a bit, seemed very hot and then exchanged numbers. Cool.

So the week of my trip comes and he texts me to see if we are still on. I say yeah, most definitely so we arrange date, time, etc.

My hometown is the kind of place where you have to have a car – public transportation is really bad – so I realized I didn’t really have a way to get to his place. He offered to pick me up, but I was not OK with my hook up picking me up at my family’s place.....

So instead I asked my little brother to drop me off – LOL. I’m out to my little brother, but telling him to drop me off at a hook ups place is a little more disclosure than our relationship entails. So I tell him I’m meeting a friend and just have him drop me off at a coffee shop near the hook up.

I walk to his apartment, which is in an area I’m familiar with, as I walk I'm thinking about how the last time I was there I was in high school hanging with friends, now years later, I’m a little transqueer walking to get fucked by some guy I met online.

I get to his place, nice guy, cute, looks older than his pic which is hot as he has a bit of a youngish silver fox thing going. We chat for a bit sitting on his couch. He is very stereotypically gay. Then we start kissing – we make out for a while on his couch, clothes still on, its get me very hard. Then he leads me to his bedroom. We kiss, he’s a really good kisser, and we make out some more shirts off, I can feel his hard on through his jeans as he grinds into me. Its too much for both of us – he pulls back, strips then unbuttons my pants and pulls them off. We kiss and grind for a while just enjoying the feeling of each others bodies.

Then I push him back and take his cock into my mouth, he’s got a beautiful cock, he moans as i guide my mouth up and down his shaft, he is the perfect size where I’m able to take his cock fully down my throat, he moans and fucks my throat until I can’t take it anymore, then pushing me onto my back he spreads my legs and begins to tongue my front hole, this I love, after sometime he climbs on top of me grabs my head and face fucks me hard.

He grabs a condom, slips it on and moans as he slowly pushes his cock into me, he lifts my legs up over my head and fucks me, slow long strokes, after a while he wraps his arms around me and pulls me up on top of him, my arms around his neck and my legs around his waist i ride him as he kneels back meeting each stroke. He says he's gonna cum soon and pushes me onto my back, we’re both moaning and fucking each other frantically, he shoots and it must be a huge load cuz even with the condom I feel his hot cum shoot into me (no worries the condom didn’t break).

He pulls out cleans up and then collapses on top of me. We lie like that for a while. Just chatting about our lives and stuff. He’s a talker which is good cuz I’m feeling a little off my normal chat game. We chat for quite a while about our lives. I like him.

Then he starts kissing me again, we kiss and grind urgently, I can feel that he’s already hard again, he grabs a condom and pushes hard into me, I pull him to me and we kiss and fuck, our bodies tightly together, he’s fucking me hard and fast, he says he gonna cum again and we keep fucking until he lets out a huge groan, he keeps stroking me and I’m cumming as well until he collapses on top of me, his body against my clit and his cock still in me I hold him tightly to me as i feel my body continue to spasm and shake.

Afterwards we lie back and chat for a while more. I ask if he needs to go soon and he says yeah but he doesn’t want to so we just cuddle and chat. Then he really needs go to. He offers to drive me where ever I need. I just ask him to drop me in town near the bus. As he’s dropping me off he kisses me good bye.

So I’m waiting for the bus for over half an hour (like i said public transit in my home town sucks) when my little brother calls me to say that they are in town having dinner and asking where I am and to join them. I hesitate a bit cuz something seems not right about going straight from a hook up to dinner with the family, but whatever.

So I meet them at a local restaurant. As we are chatting over dinner i keep thinking is it obvious I’ve just been fucking some guy, do i smell like sex? surreal to go from an anonymous cock in my mouth to sharing a slice of pie with my mom.

transfag barebacking

this piece is somewhat of a continuation of an earlier piece i wrote unsafe sex

this piece is about barebacking - fucking without a condom

However I want to be very clear from the start that I am NOT advocating sex without a condom.

i do want to talk about it though

so this is how it started. i had been messaging with this guy late one night. hot, muscular guy. that stereotypical gay boy kind of sexy. we had been messaging for a while. he had only been with non trans guys - never been with a trans guy or any other gender for that matter. And he really wanted to try pussy fucking. I was pretty horny and really wanted a hook up.

We kept chatting and the messages were getting me even more turned on. Then he asked if he could fuck me without a condom (this is not an unusual request from guys) he said he was negative, tests regularly, etc. I said no. Safe only. He said yeah he knows but he just wants to feel what it feels like. I say no man sorry we gotta be safe. At which point he says can i just put it in once to see how it feels.

I stop and consider it.

This is when i make a bad decision, i don't know why, maybe i let my hornyness get the better of me, maybe its that i'm a little buzzed, i don't know... I rationalize in my head, well just once, that's low risk, what's the big deal. So I say ok, just once.

He's really close by so i hop on my bike and head over. We chat a little, he is just as hot in person as his pics. I suck him off some and climb on top off him. He is not very aggressive so i'm taking the lead. I guide him into me raw. I'm taking the lead so I own this as all of my own, it definitely becomes more than one stroke, its very hot, and i get lost in it. After a couple of minutes he says he's getting close. I come to my senses enough at this point to stop, grab a condom and slip it over his cock, we fuck a few minutes more before he cums.

I can hear all of what folks are thinking as you're reading this cuz i would think the same thing. This was not a smart thing to do - even though safer sex education does not target trans people and definitely does not target trans guys or gender queers folks - at least in most urban centers safer sex messaging is pretty clear - its safer to use a condom.

I've never met this guy before, I don't know anything about him really, he could be lying about getting tested, even if he isn't there is a window period so unless you get tested and then are abstinent for 3-6 months there is no way to know and most people who are positive don't know it. Not even mentioning other STDs… Yeah, there was no exchange of cum, but there probably was exchange of pre-cum and I’m just lucky that he didn’t try to keep fucking me and was cool with stopping and rubbering up.

While some of it may have been that i really wanted to fuck this guy and was worried he would turn me down if i said no. And i could try and rationalize it to internalized transphobia and low self esteem, which is the reason that the few studies there have been about transfags would give for it, i'm not disagreeing with those studies or disregarding that reality.

Its just that if i really think about it and am honest with myself I don't think that was really it.

I was buzzed at the time so i'm sure that was a factor. However lots of guys have asked to fuck raw before, and some of those times i've been buzzed or even more than buzzed, and I have always said no.

Having come into my own as a gay guy with lots of access to safer sex information fucking a hook up without a condom was something i never even considered. So what happened?

If it had just been the one incident maybe i could have let it got but the thing is that sometime after this particular incident i went through this period where i was taking alot of risks. meaning on more than one occasion i was barebacking - pussy fucking without a condom. it was always with guys i consider regulars, so it was not like my 'let me put it in once guy' who i had never met before and never saw again, this only makes it marginally less risky - but its still very very risky.

the first time was with one of my regulars who i really like beyond fucking and we've been playing around for a couple months now, he asked and i said yes, he says he's negative, he doesn't play around and just got out of a monogamous relationship, somehow i rationalized that all in my head to mean it was ok (though there are countless reasons why its not). i have to admit we fucked raw more than once.

the 2nd time was with a guy who is a nice guy, fun to fuck, he is very gay and plays around some, we've known each other for a couple months as well. we were in the midst of playing around and i told him to put on a condom, he stopped and said "do we have to? i just tested negative last month". i said "well that doesn't mean anything there's a 3 month waiting period" to which he said "i know that's how i test, i've been safe in the last 3 months and its not like i've hooked up with that many guys anyways". Note all this convo is happening with us both naked, him perched over me with his hard cock pointed right at me. I waiver, i really want to, so i say yes, just don't cum inside me, so we fuck raw and its very hot.

so the last time was with a new regular, i like him, but i need to keep reminding him that this is NSA, he says he's neg tested a few months ago, gay, plays around some, we're fucking around and i guide him into me raw, he doesn't ask, i just do it, i want it. he looks at me and says is this ok. i say yeah. we fuck and at various points both of us say we should stop until finally we do before he cums.

the last time was when i realized that i needed to figure out what the hell was going on with me. that was actually when i started working on this piece.

none of it made sense, these guys are regulars, i have no fear of rejection with them in fact, i don't want to sound egotistical but all three of them are very into me, we've fucked before with condoms and i know we will fuck again with condoms. drinking was only a factor with one of them. i wasn't particularly depressed or down. so what the hell was i doing?

I've been wanting to write about this for a while. I know that I feel a great deal of shame about it, clearly I should know better, yet I believe shame and the silence that often follows do not serve anyone well.

If I'm honest with myself i believe the first guys request of just one stroke, then my regulars 'safer' (with very big quotes) sexual histories were a way for me to rationalize doing something I hadn't realized that i wanted so badly - sex without barriers - flesh on flesh - to feel a warm cock stroking me - to feel the skin of a cock inside me.

Let me be very clear I am NOT advocating sex without a condom.

I'm just trying to be honest and real with myself. I'm just trying to figure out how to live safer in the future and the only way i know how is to be real with myself about why i made those decisions.

Audre Lorde said, "Your silence will not protect you". While I'm sure she never considered it being used in this context, I think about this quote when i think about all this.

I believe if i speak this need, this desire that i have, then its real and not shameful. Even if i only speak it to myself.

Once its real, once i acknowledge it and stop hiding behind an image of safety, then i can decide if, when and how to fulfill this desire without putting myself at such high risk, without just giving into this desire at random moments when i can rationalize it in my head.

I'm owning this desire because i need to take care of myself and its the only way i know how.

NOTE: My thinking on the topic of fucking without a condom has been greatly influenced by blogger Brandon Lacy Campos' writing on the subject, particularly this piece,

bareback sex human needs vs condoms

Check out his blog, his analysis, honesty, realness and beauty are inspiring.

Caramel: My "Blue Balls" Story

We were supposed to have coffee, but opted for beers instead. It was a crowded bar and I wanted privacy; I had some questions to ask. Questions about the mechanics of what we were maybe going to do if this first "meeting" went well. See, I think it's important to clarify just how you're going to fuck before the actual event takes place. This is crucial.

Homeboy and I, after we were seated, started talking about the trivial shit we could care less about. He's a student, math major. Okay, that's kinda hot. As a proud, card-carrying nerd, I'm quite into fucking other nerds. Eventually, I just blurted out "so what do you think?" His hazel colored eyes traveled down my face, lingered for a second on my beard, moved down to my chest. "You're a dude" He looked at me then like I was supposed to feel complimented by his assessment.
"I know this. I mean, what are you into sexually?"
"Not dudes," he said and took another swig of his corona.
I grinned then. I don't know why, but there are certain nontrans guys I just love fucking with. The type who'll flirt yet still insist that I'm a girl. The type who'll message me incessantly, anxiously wanting to meet, yet when they encounter the realness of me, and the reality of their attraction to masculine bodies, will throw up some front. Alright. I decided to play along.
"Cool," I responded noncommittally, "then we're just 2 dudes having a beer." That's when he started sharing his "women troubles" with me. Women just don't get him. He was married for 10 years and she did him dirty. He's really into trans women, but responded to my ad out of curiosity.

"Tell me," he segued, "how can you be living as a guy and still be attracted to dudes?"
"I like dick," I responded, making sure to over-enunciate the K. My lightweight ass was beginning to feel the effects of the beer and I'm raunchy as hell when buzzed. "Do you like to perform oral?" he asked without missing a beat. Obviously, the beer was working on him too. "Do you?" I asked back. "Very much so. I'd like to see you without your clothes." I asked him if he was more interested in proving or disproving something else about my gender. "Maybe, but I also just want to see you." He flashed the same seductive smile he'd sported in his pic. The same pic where he'd been shirtless, a doo rag on, and his smooth, caramel-toned torso inspiring thoughts of the X-rated variety.

"Are you into rough stuff?" he continued. The negotiation had started and I was trying my damnest not to let my excitement show; negotiating sex acts is one of my favorite types of conversation. I wanted him to clarify what he meant by "rough". "I'm an aggressive top," he added with a sly grin. Oh yeah, I'm familiar with the type. For nontrans men it may mean they have to make the first move. They have to flip you around, contort you into various positions. They may talk dirty in your ear, pinning you down as they plunge into you. In other words, power - expressing it - turns them on. (I know this may sound scary to some, but power play during sex can be hot. You just have to talk honestly about what you will and won't do.) I'm not into pain and I mentioned this to him. Neither was he.

"You realize that you'll be doing all of this with a dude, right?" I reminded him, after we'd spent a few more minutes listing a few other activities we wanted to try together. He shook his head. "I can't see you that way while we're doing this." What the fuck?! "I see a dude in front of me now, but when we're fucking, in my head you'll be a..." He trailed off then and I knew what he was afraid to say. Shit. That caramel hue, smooth skin, and "fuck me" smile really had me wanting things to go down. But could I do it with a dude who refuses to see me for who and what I am?

I tried to tune out the rest of his rambling and quickly finished my beer. Snatches of his monologue, like "I can host" and "my place isn't far", inadvertently caught my attention. I had to get the hell out of there before my libido continued making decisions for me. I caught the waiter's attention and asked for the bill. "You're ready to go?" He asked. "Yeah, I'm going home, but this has been...nice." He looked surprised then. I said I couldn't sleep with someone who pretended I was someone else. I got up to go and he asked if I was sure about wanting to leave. I looked at him and, god, the lookist in me wanted to sit my ass back down. But I just couldn't let myself go there, so with that I wished him a good night and left.

Mr. Thick

So I was supposed to meet up with one of my favs, a regular, but he is very flaky, I put up with it cuz I really like him, so of course around 7pm he texts me to say that an emergency came up and he probably can’t do it. In the mean time I’ve received three texts one from a new fav, one from a new potential that I’ve been trying to schedule, and another from a recent hook up that I’ve been trying to do again cuz he is unbelievably thick.

So I debate, do i do the new hookup which could suck or Mr Thick who I know will be good (not gonna hook up with the new fav as I just hooked up with him yesterday). I go with my third text – Mr Thick.

So I’ve hooked up with this guy before, I call him Mr. Thick because he is unbelievably thick. OK looking guy, Italian, short but very built, clearly used to be very muscular now more stocky, only thing is he’s very hairy, which is not so much my thing. However, as I said before he is very, very thick.

He lives alone, very fancy apartment in a very fancy apartment building, the first time we hooked up he fucked me three, maybe four times. Very hot. So its around 9pm and I head over. Get to his place and we exchange how are you’s and then get to fucking. He’s a good kisser, we kiss for a while and he plays with my nipples through my shirt which always gets me hard. We strip down and kiss and grind some more. I start sucking him off, he is very big and hard, so its difficult for me, i mean to give you an idea of his size imagine a soda can - he is at least that thick maybe more - and a good length as well.

then he puts me on my back, I ask him if he has condoms, he grabs one and slips it over his dick. I grab my lube and lather us both up. He starts to push inside me, I ask him to go slow at first, which he does, it hurts due to his size but in a good way.

He fucks me for a while, stroking me missionary style slowly letting my cunt get used to his cock, until i want more and start to fuck him back slamming my cunt against his cock, then he starts to fuck me hard flipping me onto my hands and knees and fucking me from behind pounding me - quick hard strokes that seem to go on forever. He stops to catch his breath and i push him onto his back, i slide back onto his cock and ride him slowly just enjoying the feeling then faster until i can't take it anymore and i feel myself starting to cum, but he keeps pushing into me stroking his hips up into my cunt as i clutch his chest and cum hard. then he pushes me onto my back, throws my legs over his shoulders and fucks me hard and fast until he shoots into me.

Afterwards as we’re sprawled across his bed he starts stroking his cock again, based on last time I figure we are gonna fuck some more, so I help him out and suck him off some, its takes him sometime to get hard again which I don’t care about, i ask him to put on a condom and we fuck again for a bit, but he can’t stay hard. This is when it starts to be less hot. I would say for the next hour he trys to get hard again but can’t stay hard, we try to fuck again but he can’t keep it up – I of course get fleeting thoughts of is it me…. But I know enough to squelch that ridiculousness...

I keep saying that its cool, we don’t have to fuck again, once is cool, etc. especially cuz it really was the first fuck was incredibly hot and I’m very good. however he is determined….. so an hour later, I’m a little sexually frustrated, really I don’t care if we don’t fuck again, really, but him jerking off, even unsuccessfully has me going again. Anyways, he apologizes profusely and I keep saying not to worry about it. I ask him if he minds if I jerk off, he kisses me and strokes my nipples while I jerk off.

Then I rinse off, grab my shit and head out the door. He keeps apologizing. I feel bad for him so I send him a text thanking him again and saying not to worry about it. Of course he doesn’t text back and I never hear from him again.... non trans guys can be so ridiculous about their dicks.