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...

"get on your knees"

“I wanna see you, but it won’t be till late”
“How late?”

“If I can come through, it’ll be like 1am…”

Crap.

It was only 11pm and also a school night for that matter. I had work early the next day, yet I was horny for some dick and herein lay the predicament. And not just any dick, but that of my favorite dick-bearing black bear. Mr. gigantor. So big I could barely handle him. He towered over me too. Probably a good 6 ft and then some, built like a line-backer (I think. I don’t now jack shit about football beyond what I learned from Friday Night Lights.) I’d been steady fucking this guy for about 2 years now and during that time I’d become more dudely in appearance. Much more. I could tell, as he silently observed my physical transition during the 1^st year of our sexual relationship, he had this internal struggle going on - he couldn’t, didn’t want to admit to himself just how much he liked fucking a boy, especially a faggy boy less than half his size, that he could dominate, flip over into any position and just plough. The first time we met, he answered a craigslist ad of mine and came over a day or two later in the middle of the afternoon and sucked my clit/dick for…a long time, then slapped on a magnum and fucked me sweetly on my rickety, squeaky bed for…an equally long time.

 “You got that sweet shit,” he whispered throatily into my ear, sweat trickling down both our faces; his barrel-ly chest pressed against mine, pinning me down on that bed of mine, entering me deeply, moaning and biting my ear. God. That was one of the highlights of my highly promiscuous years. It was the vivid memory of this first moment between us that compelled myself to stay awake. More than anything I wanted to be forced on my knees, a hard dick thrust into my wet, eager, mouth.

A painful 2 hours of bad tv watching and equally bad porn- watching later, he’s knocking on my door and his burly self breezes into my apartment and settles comfortably into my lazy boy, his usual spot. That’s how familiar we are with each other, muthafucker has “his chair” in my own damn apartment. Funny, considering that I’m not even sure if his first name is actually C___. So he sits down and, still, he looks like a big ass mutherfucker. He pulls out a blunt, which he immediately starts to peel, and asks for a glass of water. I oblige. That’s the other thing about C___, he likes to order me around and I like to take it. While he rolls, he tells me about the latest piece he’s working on, some acrylic on canvas thing that his cats are going wild over. I ask if I can see it sometime, then he looks at me like he’s really giving this some serious thought. In all our two years of fucking I’ve never once seen his art, though he’s quite prolific and sells shit all the time, all over the damn place. To tell you the truth, the art and his art-making process was low down on my priority list when we first met. Though as we’ve played over the years I’ve become increasingly curious.

After taking a couple hits he hands me the blunt, which by now has stunk up my small apartment, and leaves without a word. I’m thinking that this dude is actually going to show me his work. On one hand, yours truly is quite ready for that cock to emerge. His khakis are baggy and all, but I can see the bulge okay. Apparently he’s ready too. This showing me his art thing must all be part of his foreplay, his way of making me wait. A wait to exert some sort of power, since he knows I’m always eager as fuck when he comes through. Or he just wants to show me his art. Either way, in 5 mins or less he’s back with a canvas depicting miniature black people on a giant chess board, surrounded by spirits of some kind. The colors are intense, while the images are rather abstract and complex. I’m suitably impressed, yet still terribly horny which hasn’t been helped by the blunt that I’ve been pulling on while taking all this in.

Sketches put away. Blunt smoked within an inch of its life. He’s talked my ear off about politics. I’m both hard and wet…and very eager.

He crushes the blunt in my ashtray.

 “Go take your clothes off and get on your knees,” he says while crushing said blunt and I hesitate because it’s so unceremonious. He looks askance at me. It’s a did you hear me look and I hop to. This is what I’ve been waiting for.

In the dark of my room, I’m on my knees, wearing only boxers because I want him to peel them off me like he was peeling that blunt earlier.

I wait patiently.

He comes in, already butt ass naked, dick hard as a rock and stands directly in front of me. Without a word I start to suck. But first I lick, moistening the bulbous head with my tongue. Around the pee hole first, then the head. My hands are on his hips, his hands are on my head and gently he pushes the head into my wet mouth, then withdraws. I’m so hungry for more, so I don’t let him pull out too much. He pushes back in and I take more of his cock in this time. It’s a tight fit. He steadies my head with his giant hands and rocks in and out of my mouth slowly. The suction sounds are loud. His breathing is louder. Then he starts to fuck my mouth, my tongue wrapping and unwrapping around him, the head hitting the entrance to my throat.

“Look at me,” he orders while his huge hands cradle my face.

Again I oblige, my eyes locking with his as his now wet dick slides in and out. I’m so turned on by this that I start rubbing my dick fast.

“Yeah, jerk that dick.” Him and his throaty sexy-as-fuck whispers. I swear I could come just like this. His dick buried in my mouth while I jerk mine like my life depends on it.

Suddenly he pulls out.

“I don’t want to come yet,” gesturing me to get up as he says this.

“Lie down.”
I obey. He bends over me and slowly pulls those boxers off me. This is what I’m taking about. He lifts me and positions me on the bed so he can lie down while he does what he does next, which is to run his hot tongue around my clit/dick. I jerk because the sensation is just too much, but it’s the delicious ultra-sensitivity I like. His big hands stead my hips, and  he lowers again onto my dick, flicks it gently with his tongue and each time I gasp. He’s enjoying torturing me and, yes, I consent to this. I want to be teased and tortured, toyed with while I beg for more. When I adjust to the flicking, when my squirming stops, he takes all of me into his mouth and it’s just this side of heaven. I’m sucked and licked and gently bitten. I can see my orgasm building and I have to fight it, because once I come it’s good night, which would be tragic because we have a t least an hour of hardcore fucking ahead of us.

Just when I can’t fight my orgasm any more, he gets up and the condom is slapped on lightening fast. He grabs me, flipping me into doggy. Oh a different starting position. Usually we start with  modified missionary (me on my back, legs pinned above my head). In doggy, he pins my upper body down on the bed, so my ass sticks up high. Hanging onto my waist, he impatiently rams into me without the usual slow n easy prelude. God he’s big or I’m tight or both. I can feel every single inch of his dick. It takes up every inch of space inside me. His grunting, my moaning, it’s some kind of distorted musical. He’s fucking me so fast, switching rhythms, doing figure 8s, alternating between shallow and deep fucking. And then he hits it. That spot.

 “I’m gonna come,” I barely get out.

“Good. I’m waiting for you.” That’s all the egging I need. I feel my pussy tighten around his dick.

“Shit…you got that good shit…” Damn that throaty whisper. I come right then and so does he. His pace quickens, then he groans and goes still or freezes.

Many moments later, he shakes me awake with a “I’m off." I must have passed out. I open an eye and peek at him. Yep, already showered and dressed, smelling faintly of my lavendar soap.

“What?” I was groggy as fuck, but still noticed that sly smile registering on his face.

“You were snoring.”

I gave an embarrassed laugh. “Sorry.”
“Don’t be. Go back to sleep. I’ll catch you later.”

And just like that, he let himself out while I fell into the most delicious slumber.

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.

on dating femmes: a faggy trans boy rants

I'd been locked out for hours. I was almost certain of it, even though time was starting to blur together. The sun was high up in the sky, but thankfully there was a cool breeze from time to time and some shade. Whenever I got tired of banging on the one window looking into the 5th floor hallway or sitting on the dilapidated plastic chair I'd strategically placed in front of the window, I'd pace around contemplating shit like my life and how I happened to be trapped on the rooftop of my building, the one roof in this entire city without a fire escape or any other way of getting out save for the door I was now pounding on…desperately.

I'd been seeing this beautiful femme woman of color for a couple weeks. We met on one of those dating sites us queers like the use. Y’know, the really crappy one that stubbornly refuses to broaden their gender or sexuality categories (despite the oodles of queers who populate that virtual space.) We met in person one evening. She took me to a film screening, some director I'd never heard of. While we waited for the film to start we chatted. The conversation was free flowing and somewhat relaxing. I mean as relaxing as a first date can be given all the unsaid things that weigh on your mind while you're in the midst of a 1st date. But for us the convo was great - films (we're both serious movie buffs), gender theory (what self respecting queer doesn't infuse this into ANY conversation), family history and trauma, exes, etc. By the time the movie started I was optimistic about this girl. She seemed smart, funny, artistic and hella cute. I felt ready for whatever "dating story" awaited us.

Little did I know.

But before I delve further into this story let me take a minute or two to (softly) rant on the woes of dating cis femme women when you’re a passable, albeit quite faggy, trans boy. Once upon a time, all I wanted was cock. It's true. Yes, I had sexual desires for other genders; that was always in the background. But my foreground became my lust and fascination for cis male fucking. I've written at length about my experiences and my co-blogger still writes at length about this. However, as my sexuality is wont to do, the pendulum swung and gradually space opened up in my life for other types of sex and expressions particularly with femme cis women. And the journey, folks, has been rich, hot, and affirming in a lot of ways. 

What I'm about to write will incense some and probably make you feel "some kind of way", but I'll risk it for the sake of more open dialogue on this. In almost every dating situation I've found myself in with cis femme women, I've been made to feel that only one role is available to me and that is the resident 'butch'. Don't get me wrong, I know how I look. I know that in every public space I move through, "the public" sees me as a dude. They may think I'm a particularly homo-rific dude, but a dude nonetheless. However, does being a dude automatically make me butch? Hell do I ever feel butch? With the femme women I've dated, 'butch' becomes my de factor identity. I tried hard to resist at first, but often times it’s hard to buck the trend and not fall easily into a hetereosexual-esque relationship. Also, in the same vein, in these relationships I'm also the Top. Again, I like topping, just as much as I like bottoming or fucking in any kind of "power-ed" context. However, it's the automatic and permanent relegation to this category that I find rather off-putting. And in every dating situation I find myself with cis femme women, even the ones who claim to not subscribe to such notions of relationship and sexual roles may say shit like:

"I like a guy who's chivalrous and will open doors for me and make me feel safe and protected."

or

"I forgot to go to the ATM, can you pay for this one?" (Meanwhile she's been 'forgetting' to go to the ATM every single time we've been out to eat, drink, etc.)

or

"Wait...you don't love me back?! You're such a guy!" (Meanwhile we've only been going out for a couple weeks.)

or

"What do you mean you need space?!" (I meant I can't spend 5 days a week with you.)

or

"I know we agreed to have a non-monogamous situation, but I don't want to share my man with other women...so change."

or

"I'm ready to be serious with you." (Even though we've been hanging out for a couple weeks and we agreed to keep things casual and light.)

Now, as a one-time cis femme woman and a now faggy trans guy, I understand through and through that we live in an extremely femme-phobic and misogynistic world. In fact I’ve written firsthand accounts on femme-phobia in the hook up scene. I know there's a particular way in which patriarchy plays out for women, queer folk, trans folk, etc. And even within that it looks different if you're femme, butch, gender nonconforming, androgynous, pre-op, post-op, no-ho, etc. I also remember what it was like when I dated masculine people or masculine cis men as a femme woman. I remember how easily I got attached if the masculine person satisfied the 'protector' role I'd set up for them. Sometimes I got attached if said masculine person fucked me the way I wanted to, i.e. mistaking intense sexual chemistry for a solid relationship/emotional connection. These were all behaviors or patterns I was socialized and encouraged to have or exhibit by virtue of being a 'girl'. Back then I resented being expected to act this way, and yet in relationships with masculine folks the same patterns would emerge. As I got older and my gendered experiences grew vaster and gained more depth, this 'easy attachment' or 'quest for a protector' eventually gave way to something a lot more nuanced. I realized that sexually I wanted to 'act out' the power inherent in a protector/protectee relationship, whereas emotionally, I wanted to tease out 'attachment' from 'ownership' and this is what I've found in my romantic dealings with cis femme women - there always seems to be a battle (subtle at first) for ownership, i.e. liking/caring for someone is often confused with owning someone and (indirectly) limiting that person's interaction with their communities. I know this plays out in many types of relationships, not just those involving trans guys and cis femme women. However, given how often trans male and cis women date each other, our overlapping communities and the depth of shared experiences around gender/forced gendering, there's a way in which gender/sexual roles, attachment and ownership plays out in these types of dating relationships that feels particularly problematic to me. I've had numerous conversations with other trans guys of color who are nervous dating cis femme women for fear of being forced to ALWAYS be: the butch, the top, the protector and all of that jazz. One trans guy I talked to, who dated femme women in the past, said "It looked differently in each relationship, but, yeah, I always had to be chivalrous or 'act like a guy' in some way."

I thought about all these things on that roof as time trickled by. I thought about the cis femme woman I was currently dating - the very same one that I'd had that fun 1st date with, who was now comfortably chilling in my one bedroom apartment 3 floors below. How long will it take before she notices that I've been gone for hours and starts looking for me? I was not optimistic. After our fateful fun 1st date a month ago and an equally fun 2 weeks together, things were quickly going downhill. During week 3, as the honeymoon phase gave way to reality, I realized I was in the midst of a full on heterosexual relationship where I was expected to essentially be "the man" - paying for everything, making her feel safe and protected in public, only talking about her life/problems/experiences (she liked to talk, but listening, not so much) among other things. By week 4, she wanted to spend almost day together, became obsessed with changing our poly status (even though we spent an extremely long time talking about this during our 1st week together) and altering my close relationships with friends. Early one morning at the end of week 4, I went up to the rooftop of my building to have a quick smoke and enjoy a few minutes of peace and solitude; It was just going to be me and the sunrise. She knew what time I'd left and where I was and approximately when I'd be back, so when the wind slammed the rooftop door shut, effectively trapping me there, I wasn't super worried because I figured surely after an hour, she'd wonder what was keeping me and come looking for me. I waited and waited, pounded on the door and window, yelled at the top of my lungs for someone to come unlock the door and let me back in. No one came. Not other residents. Not the girl I'd been seeing for a month, who was right now just hanging out in my apartment. Doesn’t she miss me, I wondered? Hasn't enough time gone by for her to worry that something is amiss?

After pacing the rooftop for a looonnnnggg time, I sat down on that plastic chair, my head in my hands, frustration and hopelessness crowding it. I stayed seated for a long time, until out of the corner of my eyes I saw her. She opened the door and I jumped out of that chair like it was on fire! I was so happy to see someone. She looked mildly puzzled, not concerned, just slightly puzzled. When I asked her what time it was, I was surprised to hear 4 hours had gone by. 4 fucking hours! She'd been chilling in my apartment, taking a nice leisurely shower, watching tv, playing on my laptop and doing all sorts of fun Sunday morning activities, while I'd been stuck and slowly losing my mind on the roof...for 4 miserable hours. 

"After 2 hours, weren't you worried? Didn't you think that perhaps something was wrong?"

"I guess I should have come check on you earlier," was her only response.

No "I'm sorry I didn't come up sooner" or "Are you okay? Do you need some water?" Nothing. I was shocked...especially because I'd been her Mr. Protector for weeks. The one chance she had to watch out for me, she sits back and lets me languish on the roof for 4 hours.

Needless to say, I'm no longer seeing this girl.

Can faggy trans boys date femme women and not be expected to play “the guy”? Are there any trans folk out there who’ve had similar or completely different experiences?

changes

folks who follow this blog know that i am very NSA (no strings attached).  i have been in a place for sometime now where i am not looking for a relationship or even to date.  there are many reasons for this.  and i've been really happy and content in this current place.  i've been reveling in being single.

for my entire adult life i've been in one relationship or another.  after i ended my last relationship i made a promise to myself that i would stay single for a while.  that i wouldn't just jump into another relationship.  for sometime now i've managed to keep this promise to myself and honestly i would have been content to continue reveling in my bachelor status.

but sometimes shit just happens.

i had been playing around with this guy for a couple months.  sexy non trans dude of color, stick thin (which is not usually my thing i like a little meat).  i like him, he likes me, we have amazing fucking sexual chemistry.  and sometimes we hang outside of the bedroom.  not often but once in a while.  i've met some of his friends on these outer bedroom excursions.  however throughout all this i was very clear that we're just playing around, that i'm not looking to date or anything like that, in fact the outside of the bedroom hang time felt like a bit of an adventure to me.

at different points he would say he was starting to have feelings for me.  to which i always responded that i was not looking for more than nsa play.  to which he always responded that he knew and was cool with it but just wanted to be honest with me.  this went on for sometime and we had alot of fun together.

then one night recently he came over and he didn't look happy.  i asked how he was doing and he said not ok.  i said 'what's going on'.  at which point he totally broke down, sobbing and said that he has really strong feelings for me and he can't just keep doing this NSA thing.  to which i said 'you know that i'm just not in a place right now to have a relationship' he said he knows. i felt like a major fucking ass.  it was very sad.  soon after he left and wished me the best.  

i have definitely had hookups who wanted more.  i was always clear with them that i only wanted to play.  i've had regular situations come to an end before i.e. favorite guy.  when it ended i did feel sad, but this felt different.  i realized despite all my 'nsa' stance i had started to develop feelings for this guy.  the thought of never seeing him again made me incredibly sad.

fuck me man.

i called him the next day and we talked it out.  so now we're dating - its an open kind of thing so my posts on this blog will continue, but with maybe a little different spin.

the skilled cock

dude used to be one of my regulars however we had not hooked up in over six months for multiple reasons mostly due to scheduling.  we had been hooking up pretty regularly at one point, light skin gay guy of color, slim, average build.  he'd been with trans guys before.  total dom top.  

he's the kind of hook up that i appreciate.  we would chit chat some but not alot, he prefers to get right to the fucking and then the post fuck chat is minimal.  it was not an in and out type of situation, we would fuck then cuddle some, maybe watch something on tv, he'd invited me to stay for dinner before (which i declined but thought was nice).  a good number of my regulars like to chat and i'm into that sometimes, but other times i just want to fuck and that's it.  so this dude i have an appreciation for. 

we finally arranged to meet up.  he looks a little more worn down than the last time i saw him.  hard times all around these days....  we don't chat much and get right to fucking.  we both strip immediately and we kiss and grind our bodies together.  his lips are really chapped which i'm not so into.  but he is hard immediately.  and he has a beautiful cock, it has a slight curve in it.  i quickly  wrap my lips around it and slide my mouth up and down its smoothness.  he moans. 

i grab a condom, slip it on and lube him up.  i put the tip of his cock to my cunt and slowly slide him in.  i moan as he enters me.  i ride him slowly at first getting used to the feel of his cock.  he feels so good, his cock deep inside me, i luv the way it feels as i slide up and down its smoothness.  i ride him with a silly grin on my face thinking why did we wait so long to do this again.   however now i want him on top.  i pull him over so he's fucking me missionary (missionary is my favorite position). 

he strokes me slowly our bodies tight against each other.  i grab his ass pushing him deep inside me.  i raise my hips to meet his strokes and clench my cunt around his dick in a way that also hits my clit hard.  its majorly hot.  then he starts fucking me hard and fast, pounding into me, rough fast strokes til he cums shooting inside me. 

he lies on top of me his cock still pretty hard inside me.  he keeps stroking me.  its very hot.  then he stops and starts doing this incredible thing with his cock that i've never experienced before.  i can feel his cock pulsate inside me.  its like his cock is expanding and contracting inside me over and over again it feels like he is cumming non stop.  i cum multiple times from this.  he keeps this up for a good while it feels like we are both cumming over and over again.  until he collapses on top of me his cock now soft and i slide him out.  

as we lie there catching our breath i say to him, that was incredible.  did you cum multiple times or what was happening.  he said he only came once but its something he learned to do with his cock even after cumming.  hot. 

we lie around a bit just resting, however i need to go so we clean up and part ways with a quick kiss. 

disappointing fuck

dude hits me up on one of the sites.  his profile says he is 45 years old.  however in his pics he looks barely into his 20's.  Japanese guy.  i message him back and say there is no way you are 45 years old.  though i'm also thinking there is no way those pics are current.  however, i know alot of people of color look way younger than their age...  case in point myself transness aside.  we bond over getting carded regularly at bars and even at times for cigarettes.  i'm still a little suspicious about the pics but we keep chatting.  he's interesting.  i've found that older guys often have lots of interesting stories and he seems interesting.  he has strong racial politics which is also a major plus.

he has never done a trans guy, in fact he has only been with non trans guys his entire life.  he states he is not sure about how he will react but thinks i'm majorly hot.  we get into a pattern of sending at least daily messages to each other discussing a wide range of topics from what we want to do sexually to gentrification.

after about a week or so of this he mentions getting together to explore my body i.e. fuck.  we decide to arrange a date however i'm feeling conflicted.  on one hand he seems like a real interesting guy and his pics are cute and he said he prefers a slow sensual fuck and right now i mostly have rough dom types.  on the other i have a feeling his pics are inaccurate and he is not gonna by attractive to me.  i also have this feeling that maybe his pics are very, very old and he will not look anything like his pics.  don't get me wrong i get majorly into a hot daddy but i'm unsure if this dude is that.  however, i decide to just go for it mostly cuz i find him interesting, i tell him to meet me at a coffee shop near my place so i can feel it out.

we meet up one week night evening.  he shows up and he doesn't look like his pics.  however he's cute in a round, brown boi kind of way that i find very attractive.  we chat some and then i ask if he wants to go back to my place.  he says sure.  we get back to my apartment and resume chatting on my couch.  now i'm realizing maybe he's not so attractive to me.  the coffee shop lighting was a bit dim....  he also is not really as interesting in person.  we chat for a while, random usual prefuck chat, nothing inspiring.  I'm feeling disappointed as he was so interesting via email....

he seems like he could keep on chatting all night so i realize i'm gonna have to make the first move.  i ask if he wants to go to the bedroom.  he says ok and we head to my room.  this is when things start going even more down hill.  we strip and i realize he really is even less attractive to me without his clothes on.  however, i hold out for that sensual fuck he described. 

we fuck.  its not short, but not long and just not that great.  the whole slow sensual fuck he described to me is no where near what happens.  basically i ride him til i cum then he cums soon after.  nothing sensual about that.  after we are done i decide i want him to leave though its clear he wouldn't mind staying and chatting.  i toss him a towel and ask if he wants to clean off.   he cleans up, i thank him for coming over and show him out. 

you can't make this stuff up...

sometimes what happens on a hook up is almost too much to be believed.  this guy and i had been messaging on and off for a while.  tall, white, dark featured guy.  older.  a runner. 

we finally arrange to meet up and i kid you not, this is what happened.  dude show's up. he's a little less toned than in his pics, but whatever doesn't matter all that much to me.  he's a talker.  kind of talk's non stop.  he's a magician by trade.  interesting.  he has been doing it for a really long time.  he says he wants to show me a clip from one of his shows.  we watch it for a bit.  he is pretty good.  this is all fine. 

we are sitting side by side on my bed continuing to chat.  then he tells me how he's learning hypnotism.  interesting.  he says the first thing you learn is self hypnotism.  i say are you serious - what's that.  he says let me show you.  then dude, i almost can't write this, seriously fucking closes his eyes, sits with his palms up on each knee like he's meditating and says "i am powerful" or some shit like that and then just sits there with his eyes closed.  after about a minute or so during which i am really questioning how i allowed this person into my bedroom, he says the same phrase he started with "i am powerful" or whatever and all of a sudden open's his eyes.  They he says "see, that's how it works".

at this point i'm really unsure about all this, i mean perhaps self hypnotism really does exist, but why would you choose to do it on a hook up, then he leans in and plays with my nipples.  this is an immediate turn on for me and the ridiculousness of the last few minutes somehow leaves my mind.  we fuck, its good, not amazing or worth going into too much detail about, but soon after we are done i show him to the door.

lessons learned - anal cleansing

i've been doing alot more anal these days.  just a mood i've been in.  i choose the dudes i do anal with carefully though.  i prefer a cock that is medium to long in length but not thick.  i mean i've been ass fucked by quite sizable and thick members before and had a lot of fun with it, but i can often only go so long.  

the rest of this post may be tmi for some so please skip it if needed.

the other thing about anal for me is that i have an issue with feces.  its just not my thing.  no judgement for those into it, its just not what turns me on.  even though all the guys who fuck my ass don't care how 'clean' i am and if there's some mess which there is apt to be with anal fucking it doesn't bother them.  however it bothers me, which means i can't relax and just have fun with it.  clearly my issue.  i know that some mess is par for the course with anal fucking and there is nothing wrong with it.  again all my issue.

but i like to get fucked in the ass now and again and i like it to be fun for me.  this had led me to get into anal cleansing/douching.  i understand that it increases risk of hiv/stds to douche before sex but except for with one special person (with whom I have an agreement and arrangement) I use condoms and lots of lube. 

this all led me to purchase my first anal douche.  i went for the low budget model as that is my current situation plus who knew if i would be into it or not.  the thing is it comes with very little instructions so i did some reading on the internet and generally got a sense of what needs to happen.  i just use warm water.  i know there are solutions and mixtures but those seem to come with more possible negative consequences.

the very first time i tried it i didn't use lube.  maybe its just the way my ass works but i could not get the nozzle in and quickly realized i needed to lube it up just a little and then it slid in just fine.

however then another challenge arose.

the first few times it was really hard for me to squeeze that water into my ass.  like i would have to really strain and squeeze the bulb of water really hard.  even then it could only get about half of it in.  however it generally seemed to do the trick.  though i noticed sometimes i would be totally clean and other times not.  after maybe the 3rd or 4th time i realized what i was doing wrong.  basically i think i was inserting the nozzle (for lack of a better word) so far that it was blocked by whatever part of my inner lining it stopped at.  if i pushed it in then pulled it out just a little i was able to get all of the water in with no problem with much better results.

great.  seemed like i was getting the hang of it.  however, in my effort to be clean one time i over did it.  lets just say i did one more bulb of water than i should have and didn't properly evacuate.  luckily when i felt a weird gurgling in my lower region i was alone at that point and able to make it to the bathroom just in time.   

after all this i think i've pretty much got it down now i.e. how to get the water in my ass and how to make sure it all comes out.  feel free to share tips if you'all have them : )

itchy

it had been a lazy day.  i had hung with a friend earlier and i was just at home drinking some wine, cooking some food, i was looking for a hook up but in a kind of lazy way.  not having any luck on any of the sites - slow day when i got a call on my cell.  i didn't know the number so i didn't pick up - as is my practice.  i listened to the message and it was some dude who said we'd been emailing, that we had met through CL and wanted to know if i was free to fuck.

i have no idea who the hell this guy is.  i had not posted on CL in a number of months.  so i went back through my email to try and figure it out cuz clearly we had been chatting since he had my number.  after some investigation i figured it out.  its this dude that had responded to an add almost six months ago.  we had emailed on and off but neither of us could host and i'm not into motels.  also he was ok looking in his pic like it could go either way. so i'm feeling indecisive, i'm not incredibly horny, can't decide what to do. 

i text him back and he calls.  i hate talking to hook ups on the phone, i would rather text, but whatever.  turns out he lives three blocks away.  for folks who follow this blog you know i have two major weaknesses:  1) anything local, 2)  dom tops.  so 3 blocks is fucking hot.  i think what the hell, lets do it.

he says he can host, but he'll have to sneak me in.  i'm not sure what that means, but whatever i'm game.  i say i'll be there in a few minutes.  i walk over to his place.  he comes to the door and does not at all look like his pics, not attractive to me, however i'm here and now horny and i've learned that physical hotness and sexual hotness do not always equate meaning i've fucked hot dudes who suck in bed and i've fucked unattractive dudes who are majorly hot in the sack and really i'm just here to fuck.

it turns out that sneaking me in just means tip toeing past his roomie.  he lives in his studio, he's an artist.  cool art.  no bed but i don't care there are lost of places to fuck.  we kiss, he showered right before i came which i appreciate however it means his long hair is damp which sometimes is hot but in his case is not.  he lays me down on some blankets on the floor.  he sucks my nipples, blows me, all good.  however i want to be fucked.  i suck his cock but he can't get hard.  he jerks himself off, i suck him some more but no go.  he apologizes says he did some coke earlier and has coke dick.  great.....

it turns into an oral session, he sucks me off, finger fucks me, i cum, but its not really doing it for me.  afterwards i get up to leave and he says 'no stay a little longer'.  i lie back down but realize something about this is making me feel itchie.  so i get up, grab my shit and bounce.

i was feeling bad about this hook up.  not so attractive dude, high on coke, limp dick.  my thoughts ran on these lines - what the hell is wrong with me.  if there is ever a time to walk away that was it.  why don't i have enough self respect.  why am i such a chicken shit. 

I have never shown up at a hook up and walked away.  While i feel confident that if a situation ever felt unsafe I would walk away I have been fortunate so far.  my best friend has no problem walking away from a hook up.  he does it with ease.  though the times he has had to walk away are mostly when its been a sketchy situation.  however, its hard for me to do and i know that i have a problem rejecting people - clearly my issue - that maternal, self sacrificing, put others over myself instinct that i can't seem to get rid of.

i was feeling really down on myself, went to bed feeling like shit.  however i woke up the next morning and decided to give myself a break.  while i acknowledge my areas of needed growth and the hookup did make me feel itchy....  at least i did take enough control over the situation to get what i wanted out of it - which was simply to get off...  the rest i'll keep working on

On Fucking Femmes

This is the 3^rd girl I’ve fucked in the last few weeks of my recent sexual transformation. 5 years ago I would never have even seen this coming, this strong sexual attraction for femme women. But this is where I find myself these days and I’m having to learn how, in my present fully passing black masculine self, how to approach and talk to women about casual sex, how to fuck women and be pervy and kinky, how to top and dominate a woman in a way that makes her feel sexy, horny and trusting enough to give over control. This particular woman actually approached me and, in my oftentimes-clueless state, I didn’t know or understand she wanted me to invite her over to my place and fuck the hell out of her. Not when she stepped to me and asked for a kiss at our 1^st hang out (see An Ode to Trans Guys.) Eventually she had to spell it out for me in our ensuing texts and, since then, I’ve jerked off many times thinking about her riding me wildly.

Well that 1^st hang out was several weeks ago. We’d been trying to hook up since then, but she lives out of town, is in seriously committed non-monogamous deal and quite busy. The odds of us actually meeting up started to look really slim. Eventually the odds were in our favor (shameless Hunger Games-phile here) and she happened to be in town one week when I actually had money in the bank. I invited her over for a home-cooked meal and thought that afterwards, if we were still feeling each other, we’d make-out and eventually fuck.

Later that night we chilled in my living room, drinking after dinner. A dinner I’d just whipped up that fell far short of what I’d hoped and dreamed it could be. She seemed to like it, or at least she said she did. The conversation was more relaxed now that wine had made an appearance. It made her smile and laugh more. It made her gestures more dramatic. As she talked I switched seats and sat right next to her. I put my hand on her thigh and felt the strongest urge to kiss her, but I was still new at this dating-and-fucking-femme-women thing, so I held back.  The sexual tension between us was thick in the air. We’d spent so long talking tonight, and still the tension was in the air. Eventually…

“I want to kiss you,” I stated once she paused for air.

“Okay.”

I kissed her while the smile was still on her lips. They were soft and wet and felt hot in my mouth. That I expected.

What I didn’t anticipate was the degree of sexual attraction that lay between us.

It took a few minutes to build.

Suddenly, as mouths parted and tongues collided, she climbed on my thighs and started grinding her hot crotch on mine. My dick was hard, so fucking hard. I grabbed her ass as she rubbed up against me.

 I slipped my warm hands underneath her blouse. One hand crept to her bra strap while the other cupped her big soft breasts. She moaned in my mouth, sucking on my tongue, twisting and grinding on my crotch as her hands wildly caress  my back. Eventually she wants more access and pulls my shirt up my back, reaching underneath the A-shirt, I wear to flatten my chest, to my bare-back.  By now I’ve unbuttoned that bra, my hand twisting and squeezing her bare nipples. She’s moaning, sighing, saying “shit”, “damn” and asking me to squeeze them harder.

“Wanna go into my room?” I ask as we’ve outgrown this couch. She nods and we kiss and grope and fondle our way into my bedroom. On the way I squeeze my hands down the back of jeans to her naked ass. I squeeze softly at first, then hard and bring her closer to me, kissing her mouth and playing with her tongue.

In my room she pulls away.

“Can we talk about safe sex?”

I’m in the process of taking my pants off. I nod and gesture for her to continue.

“Latex all the way. If you’re strapping on, if you’re fingering me, all of that is happening with latex. I brought condoms and,” she bends over and retrieves a box and some condoms from her bag, “gloves.”

After kissing and sucking and licking her tongue, after taking one erect nipple into my mouth, sucking softly then hard and repeating, after I put my thigh up against her pussy, grinding and feeling the hot wetness slide up and down my thigh, after she reminded me to put gloves on because my eager fingers started to part her wet and warm pussy lips, I slipped a couple gloved fingers into her pussy and played with her clit. Even through the glove I could feel the heat of her. She was so wet that sounds of my fingers playing with her pussy filled the room.

I have a huge, huge acoustic fetish. I love dirty talk, moans, grunts, curses, and most especially wet fucking sounds. I started finger fucking her, first it was shallow and slow, her hips moving in response. Then her hips moved faster and my fingers plunged in deeper, she arched. Her soft warm body undulated beneath me. I fucked and she moaned, bending her neck backwards, head pushing into my pillow. I finger fucked her harder, which deepened her sounds, mouth opening wider. I bent my head and pushed my tongue into her warm open mouth and twirled with hers. She greedily reciprocated, taking all of my tongue into her hungry mouth, sucking. I ground into her more vigorously, egged on by her sounds, the degree of wetness on my hands. Suddenly I pictured my dildo buried all the way in her warm tight snatch and it was an image I wanted to bring to reality. Quickly I got off her to retrieve my strap-on.

10 embarrassing and ultra dorky minutes later, we gave up on using the strap and just opted to use the dildo alone.

It turns out the harness was broken.

We still tried to use it. That’s how badly we wanted a strap-on to feature prominently in tonight’s activities. 

You would think all that fumbling around and tinkering with a broke harness would kill the mood, but as soon as she got on top of me, her full breasts dangling over my face, nipples poised on my lips, I got hard in seconds. Her nipples slipped into my mouth and I bit them, she ground her pussy on me, rubbing her clit on my thigh, until the intensity of that made me sit up and hold her naked body to my sweaty one, breasts in my mouth, sucking a little hard this time. It was time to use the dildo. I laid back down and positioned the 8-incher on my crotch. This was my fave one. It was thick as hell and I’d never used it on any one else before, but I was ready to try that.

She climbed on top of me and slowly slid down my dick.

Her mouth fell open.

“It’s huge.”

She moved slowly on my dick, coating it more and more each time. I loved watching my dick emerge from her pussy wet.

I loved the feel of her bare ass in my hands as she rode me.

She started moving faster, hungrier.

I grabbed her supple ass harder and moved my hips, thrusting up to meet her, feeling like this piece of silicone was actually my dick, disappearing in and out of her. We moved faster. I sat up again because I wanted to feel her body against mine, her breasts pressed against my chest. My dick slipped in deeper and I grabbed her ass hard and fucked her deep and rough for a long time. Eventually she grabbed my shoulders, squeezing, head tilting back and let out a loud loud moan. As she’s bent backwards like this, I can’t help but take a nipple into my mouth, which makes her gasp and gently push me away.

“Once I come they feel really sensitive,” she barely gets out in between pants, before practically collapsing on the bed beside me and nestling her bare ass against me.

I’m a panting and sweaty mess, so I get up to wipe off. Once I’m somewhat dry I get back into bed, my arms wrap tightly around her.

The last thing I remember thinking right before passing out is how much I love the smell of her pussy.

my first STD

we said we would write about the good and the bad.  we promised honesty and realness. here goes. 

i went to the doctor because i had a yeast infection.  i used the over the counter stuff which helped but it didn't feel like it was fully gone.  since i was at the doctor and it had been exactly three months since i was last tested i asked her to also test me for STDs.  she confirmed i had a yeast infection and gave me meds.  what's funny is this time i wasn't actually worried at all that i had an STD.  I was actually very confident that i was fine.  this i believe shows how i had been getting lax.

a few days later i get a call from my health clinic.  they let me know that i had tested positive for an STD.  that it was easily treatable and that i just needed to come down to the clinic for the meds.  the guy who called was very nice about it all.  he said my partner should get treated and tested as well and asked a question about my partners gender (i don't remember the exact question) to which i responded guys - plural.  he paused.  interesting assumption that i have one partner.

as he's telling me more about the std, i'm just half listening as my mind is racing through my last 3 months of hookups trying to figure out how this happened. 

i had recently, really just two weeks prior hooked up with two regulars, one who i've been seeing now for a long time and one who i've been seeing for a bit but is newer.  with both of them we had fucked without condoms for the first time.  with both i had really thought about it before we did so, though in retrospect i was most focused on hiv and didn't really think about other stds (clearly a mistake).  With one we had talked extensively about testing and safer sex practices with the other to be honest we didn't, we had been hooking up for a long time on a very regular basis and i just felt a level of comfort and trust with him that made me lax.  i hooked up with them just a few days apart. i'm sure many folks are shaking their heads reading this, i know it was not the best decision.  other than that in the last three months i had been safe. 

i said to the clinic guy, i am normally safe, but i had unprotected sex with someone two weeks ago, could it happen that fast?  he said yes and that's probably when you got it.  he said this std is common and alot of people have it and don't have any symptoms.  I didn't say unprotected sex with two people, i just felt stressed, embarrassed and was afraid of judgement. 

after hanging up the phone i just sat there for a minute feeling like shit.  i felt ashamed, embarrassed, stressed, and overall i just felt stupid. 

i called my best friend and told him.  i luv my best friend.  he said its nothing to be ashamed of, its just an infection, its common, if you had an ear infection you wouldn't be feeling like this.  its easily treatable.  however, he said, maybe you need to rethink this no condom thing.  to which i said i know.

all of what he said is true however i still felt like shit.  i told him that i was planning to text the two regulars to let them know so they could get tested.  he said are you sure you should do that?  what if one of them gets violent or something.  to which i said, one of them i have no worries about, the other i'm not sure but while we've been playing for a while we are very anonymous so there is little he could do if he was angry about it.

this all just sucks.  i text both of my regulars and let them know in a very non blaming way, non accusatory way, and tell them they should get tested.  the one i had no worries about sent a really nice response, which i knew he would, he said he was so sorry if it was him and that he didn't know if it was and said he hoped i was ok.  so nice, to which i responded that he didn't need to apologize and that i hoped he was ok too.  the other one at first was like, wtf, its not me.  to which i just said your probably right but i just wanted you to know so you could get tested just in case and i hope your ok.

i'm feeling really down and bad about myself.  i start to worry what if i got it from one then gave it to the other.  i start to feel all guilty and bad about it all.  again i'm talking to my best friend and he says it was as much their decision as it was yours.  you are both equally responsible. which i know is true but i still feel like shit.

later that day, i'm still feeling shitty, and all of a sudden i remember that there was one other.  this one was a total mistake.  just a total fuck up on my part.  yet somehow i had totally forgotten about it.  honestly it just slipped my mind entirely. 

i hooked up with this dude, i didn't know before we met up, but we run in the same social circles. for some reason the fact that we know alot of the same people made me feel very comfortable with him and i was lax.  we also both were very drunk, again not something i normally do with a first time hook up, but i was feeling very comfortable.  we fucked of course and we started out using condoms however there was a point where we fucked without a condom for a bit.  this was a mistake.  i made a promise to myself that while i might bareback sometimes that it would only be with regulars who i've know a while and after we've discussed testing and safer sex practices and that i would very rarely do this.  this incident was just a total fuck up. 

and i had really just forgotten about it.  now i'm starting to feel really shitty.  as i had told the newer regular, when we were discussing possibly going raw, that i used to bareback sometimes but it was too stressful and that i had been safe since.  what if i gave the std to him? (he texted me a few days later to say he'd tested negative)

i never heard from the other dude again.  we had been hooking up on a pretty regular basis for a long time, really good fucks, major hottie, we also got along as people - he's a really nice guy.   par for the course in the hook up world.  i actually would have hooked up with him again, safe only, if he had contacted me and let me know he got tested, even if he found out he had the std, yuh know shit happens.  i am very judgemental of myself less so of others, clearly my own shit. 

i know that i had been getting cocky (no pun intended) and over confident and lax.  having an std is bad enough and i know i'm just lucky its something curable, adding on worrying that i gave it to someone and having to notify my hook ups - all sucks

my first cross dresser

I did this hook up a while ago, but just have not gotten around to writing about it so apologies as the details may not be so clear. I am a very queer, pansexual type of guy. While i've mainly, well lets say exclusively, been into fucking non trans dudes lately, I am very open in regards to gender.

This person hit me up, I think through craigs list. Her picture is of a beautiful, sexy woman, long brown hair, sexy long legs. She/he identifies as a cross dresser. When in dress they go by she and when out of dress by he. I have never hooked up with a cross dresser before - well that i know of. She/he says she wants to dress for me and then fuck the hell out of me. Hot.

I know that cross dressers are not always welcome amongst us trans folks. And I get and understand where that comes from – trans folks struggle and deal with shit 24-7 for being trans or genderqueer and the idea of people being able to take gender on and off or to use it to get off brings up complicated feelings. I get that.

However, I want a world where all genders are celebrated, where gender can be fluid, where changing and playing with gender is sexy and hot and doesn't need to cause pain.

While I know we do not live in that world i wish we did.  And while i have made many missteps, i strive to create that world in how I interact with other folks who do not easily fit into main stream society's ideas of men and women.   However, I do admit I feel some kind of way about people who play with gender and make a ton of money off it yet don't ally with us trans and gender queers – to me that's not about them being cross dressers that's just about them being wrong and capitalists – which occurs regardless of gender.

That all said onto the hook up. I get to their place.  I remember dark colors, darks reds, some frill here and there.  I luv it. I'm a little nervous though. I've just been in such a masculine space lately and I'm just not sure how i'll feel in this situation. She lets me in. She is wearing a sexy red dress, long hair, heels. She pours me some wine. We exchange the usual pre-fuck chat – home towns, work, etc. I ask her what pronouns she prefers. She says either is fine but I can use she for now.

She says in an ideal world she would be able to go to work one day as woman and the next as a man and it would all be ok. I decide that she is wonderful.

Then we get to fucking. Again this happened a bit ago so I don't remember all the details but here are some highlights. We are sitting on her couch. I kneel between her legs, push up her skirt, pull out her sizable cock and take it down my throat. She pulls me up, turns me over and thrusts inside my cunt. We move to her bed. She raises her ass in the air and tells me to spank her. Which I do. She moans saying 'harder' until she can't take it anymore and pushes me onto my back. She climbs on top of me, spreads my legs and pushes inside me. She's fucking me hard and frantic and groans as she cums in me.

Hotness