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.