limp dick

I've been meaning to write about this encounter for a while so apologies as i don't remember all the details.   i don't remember how this dude and i connected - Manhunt, Adam4Adam, craigslist - who knows.  Gay guy, never fucked a pussy before, really wants to hook up with a transguy, very cute.  We had been corresponding for a while but unable to hook up due to both our living situations.  we finally set a date.  I head over one friday night, he lives in the gay section of town.  he is also very discreet, won't exchange numbers only email.

get to his place, nice place, small, turns out he's a med student crashing with his brother who just happens to be out of town.  he is as cute in person as his pics, skinny, tall white guy.  we sit on his couch chatting for a bit.  he admits he is very nervous.

he says i look kind of like demi moore in GI Jane.  OK this is a bad sign and that comparison is far from reality....  however after saying that he leans over and kisses me.  we start making out.  its very hot.  i'm horny.

i forgive him the demi moore comment.  i can feel his hard on through his jeans.  we take off our shirts and continue kissing and grinding.  i unbutton his pants, pull out his cock and suck him off.

he says lets go to the bedroom so i follow him in.  i suck him off some more.  then i hand him a condom.  he slips it on and pushes into me however soon after he goes soft.  he pulls out and i suck him off some more however he is still soft.  he apologizes says he's just so nervous.

so for the next seems like hour but i think it was more like half an hour he and i try to get him hard.

i'm patient but this is not fun and i'm starting to have feelings of insecurity i.e. is it me, type of feelings.  at some point i'm thinking should i just leave.  this is ridiculous.  after what seems like forever he finally gets it up.  he fucks me from behind - lasts about ten minutes...  i get up, put my clothes back on and bid him good bye. 

this perhaps was not a good use of my time

"more"

so folks who follow this blog know that i don't like to write about my regulars. just a thing i have.  however last nights fuck session was so hot i have to write about it.

so this dude and i used to hook up pretty regularly, we like each other as people and have hot, fun together.  he's white, a tall, meaty guy.  not muscular, not a bear.  just a big tall dude.  and he's very cute, in that nice, smiling guy kind of way and he is a bit of a queen - all of which i luv.  he's a well off guy, in finance or something.  he's familiar with trans folks.

so for one reason or another we had not hooked up for i would say nearly six months.  we finally arranged to meet at his 'summer place' - no one in my life has a 'summer place'.  i wanted a hook up but wasn't expecting anything mind blowing.

i get to his 'summer place', he pours me a drink.  we chat for a few minutes then get straight to it.  i straddle him as we kiss and make out.  we're both moaning as we grind and kiss.  i pull off his shirt and take off mine.  he immediately starts sucking my nipples, which we have mutual luv for.  he has humongous hands and wraps them around my torso as we kiss - he can almost wrap his hands around my entire body  - i feel so small in comparison - which turns me on

i reach down and feel that he's already hard.  i stroke his cock through his shorts.  i bend down and take him into my mouth.  i had forgotten how big he is.  i blow him for a while, he groans as i stroke him, then he picks me up and turns me onto my back.  he lies on top of me and kisses me as he rubs his cock against my clit.   i really wanna fuck so i push him off and reach for a condom, but he spreads my legs and wraps his lips around my clit.  i moan as he goes at me.  now i really wanna fuck so i stop him and push him onto his back.  i grab a condom and slowly guide his cock into me.  i haven't been fucked in a bit so i'm tight and he's big so i take my time, taking him in slowly.  then he's all the way in me and i ride him.

i remember that he can last a long time so i take my time with him.  i ride him slow, i like to feel every inch, and he feels incredible, stretching me and taking me deep until i cum clutching him tightly to me.  oh yeah, he says.  then he simply says 'more'.  i remember now how he likes to make me cum multiple times.   its a real turn on for him.  and i never turn that down.  so i keep riding him until i cum again.

'more' he says and turns me onto my back.  fucks me missionary style til i cum its warm in the room and we are both drenched in sweat however he's dripping sweat all over me (which i don't like) so i push him back onto his back and mount him.  i lose track of how many times i cum, he keeps saying 'more' in this sexy voice but i know i can't do much more so i begin stroking him to make him cum, slow at first, clenching my walls around his cock on each upward stroke, milking him as i ride him, he moans, i fuck him harder and faster, clenching myself around his cock, he's moaning yes, oh yeah, and his body arches up as he cums, but i keep riding him, sucking out every bit.

then we lie back and rest and chat.  he starts talking lgbt politics.  he's a liberal guy, not progressive but liberal.  however i want him to stop talking.  i have very strong, leftist leaning political views and have lots of thoughts about the current state of lgbt politics, much of it based in my understanding of the inherent racism, sexism, classism, transphobia, ableism, xenophobia, and ageism of the lgbt political world.  and i'm here to fuck and chat some - i'm not here to get in a political debate.  so while he clearly wants to talk politics i change the subject.

we start talking gender and attraction and he say's 'i like a little change now and then' with a smile and begins kissing me and stroking my clit with his fingers.  i wrap my hand around his cock and he's starting to get hard again.  we fuck some more til i start to get sore.  he tells me to sit on his face and sucks me off as he jerks himself off.

then we both must have fallen asleep.  i wake up and realize its 230 am and i need to work the next day. i've been there over for five hours.  i get up and clean off a bit.  he's asleep so i lean over and kiss him good bye, he says sleepily 'i guess your leaving' - cute, i say yeah babe, gotta work tomorrow, he kisses me again and i slip out the door.

human connection

I was thinking about this interesting hook up I did yesterday. It was one of those spur of the moment kind of things. I had been logging into my sites on and off all day between errands, etc. it had been a slow unproductive day. I had just finished making some food and decided to log in again. All of a sudden a bunch of guys hit me up. One in particular was interesting. He was local (folks following this blog know my issue) and definitely had that typical gay boy hotness going - white boy, tall, cut but not beefy, very cute - he also had some nice tats and a few piercings - all of which are favs of mine. So I sent my usual response. He said all good to me, never done it before, but into it. I said, cool what yuh looking for? He said just looking to have some fun. I said fun is always cool. We arranged to meet in half an hour.

So normally I go into more detail i.e. what i do and don't do, but sometimes for quick things and this seemed like a quick thing i don't

So I head over, he's as cute in person, incredibly hot actually. We chat for about 5 minutes then we start kissing. We kiss and make out for a while then he leads me to his room. We kiss and make out and grind for a really long time, this amount of making out is cool with me but after a while I start to wonder what’s going on, he doesn't seem nervous or anything like that, so i just take the lead and reach down and unbutton his pants, he reaches for mine and we strip. 

I kneel in front of him and take his cock into my mouth. i suck him off for a while, then he reaches down and pulls me up on top of him. we kiss and make out and grind against each other. then he flips me on my back and sucks my nipples. he asks if anything is off limits. nice guy. I say i just don't usually do anal anything else is fair game. then he reaches down and begins playing with my clit and sucking my nipples at the same time. i luv nipple play. then he moves down and tongues the inside of my thighs before moving in to suck my clit. he is really, really good. he plunges his fingers into me and sucks my clit. hot.

however, i want his cock. i push him onto his back and we kiss and grind, i rub my head against his, he moans, he's very hard. i ask if he has a condom. he grabs one and slips it on. i mount him, but realize he's gone soft. i ask him if he wants me to suck him off some more he says yeah. then he pulls me up and we kiss and grind, he says i should cum if i want, i say ok and get myself off grinding my clit against him. then he lays back and jerks himself off while we kiss.

at this point i'm feeling unsure about this hook up and wondering how long i should stay before i leave when he drapes his leg over mine and starts to chat. we chat about our lives, where we are from, what we like to do, the gay scene, he asks me questions about my transition which i'm fine with - he also asks first if its ok to ask. we chat for at least an hour. at one point he pulls me closer to him and we cuddle as we chat. the chat is good, but there are definitely a few awkward silences. I like him, but its not the immediate vibe i've gotten with some of my hookups where we just hit it off from the get.

i tell him i should probably head out, then he says 'oh, i was wondering if you want to do it again'. i debate and decide to go for it. we kiss, make out, he sucks me off, and he's really hard so i ask again if he has a condom, he says yeah, he says its embarassing but i get real nervous with condoms, he says don't get me wrong i really want to... i say no worries man. he says and i'm not going to ask you to do that (meaning fuck raw). so i cum again from grinding against him and he jerks off while we make out.

then i say ok, i really gotta go this time. i clean up and head out.

i was thinking about this hook up afterwards. i mean this guy is incredibly stereotypically gay boy hot - i am sure he can walk into any gay bar and gets immediate attention, i am sure he has no problem hooking up with people whether it is online or at the local gay bar. he seemed like he had his shit together - yuh know you can pretty much tell when someone is in a good or at least ok place in their life and when they are at a pretty bad one (no judgement - we all have hard times in our lives).

what i realized is that i think he really just wanted some human contact, to have some real conversation and cuddle and kiss and feel each others bodies. getting off was secondary.

i've been trying to figure out why this was so suprising to me.

i've hooked up or chatted with other guys like that before but it was always guys who i could see how they have a hard time dating or hooking up or whatever because they don't meet society's fucked up standards of beauty or they just seem like they are not in a good place in their life. but this guy was the epitome of gay boy beauty in society's eyes and really seemed to have his shit together.

i guess it just made me pause and reflect some on the need we all have for meaningful human connection and how rare and difficult it is to find. So difficult in fact that we find it where ever we can get it even in the world of online fucking and anonymous play.