the italian

due to work i went two weeks without being fucked.  for me this is a very, very long time.  so finally things in my life calmed down.  during this two week period tons of new guys had hit me up of course this always happens when i can't hook up.  there were a number of interesting guys.

one was very persistent.  i've decided to call him the italian. hot in his pics.

we finally arrange to meet.  he's ok looking, not as cute as his pics, but ok.  one of those ultra masculine types.  he's bi, mostly fucks women but likes a guy now and then.  usual prefuck chat. he say's i'm not sure what to do,  should i turn down the lights?  cute.  i ask if he's nervous.  he say's no its just always hard for him to transition into sex.   i'm sitting on the bed so i motion for him to come over.

he starts kissing me.  we undress and he begins sucking my nipples (which i love) then he spreads my legs and begins tongueing my hole, stroking my clit with the tip of his tongue.  he's good.  not the best i've ever had but good.  he goes at me for a while til i decide i've had enough.  i push him off.  he lies back and i take his cock into my mouth.  i blow him for a while then grab a condom.  i guide him into me and ride him for a while.  he flips me over and strokes me missionary style.  then he pulls back and goes down on me again.  clearly this is something he loves.  we fuck like this for a while.  he fucks me then goes down on me.  fucks me then goes down on me.  its good.  not the best but good.  he says i could eat you all day.  nice

afterwards we're chatting some.  this is when i decide i like him as he's a really interesting guy.  hasn't been in the US for that long, he's an actor, performs often.  he is that stereotypical romantic italian.  which i realize i luv (who knew?).   we are talking tattoos and he tells me this story about how one of his tats represents his one true luv, this women who he has never been in a relationship with as the timing is never right, he's in a relationship, she's in a relationship, etc.  however they both know they are each others true love.  so i'm not much of a romantic but with stories like that i can't help but like the guy.

i get up to go and he asks if i want to stay for dinner, i decline as i need to head home and plus that's not something i normally do.

and then it gets even better.  he messages me afterwards to say he really enjoyed it and hopes we meet again and everyone once in a while in his messages he'll throw in a word in italian.  'bello' - handsome.  'bacio' - kiss.  

god who knew that i'm such a sucker for that kind of thing....

trusting my instincts

when i first wrote this piece it started out like this - "my coblogger wrote a piece titled 'surprising good fuck'.  i just did this hook up and really, that's the only title that works to describe it so in order to not entirely copy his title i added the words 'more on'. "

however since then i decided to change the title from 'more on surprisingly good fucks' to 'trusting my instincts'   

this is how it started. i had the afternoon off.  i was very horny and really wanted a hook up.  however, i was feeling very tired and lazy and either wanted someone to come over or i did not want to travel more than 10 minutes on my bike.  i only have a few hookups that i would consider inviting over.  i don't like to host, just not my thing.  so i hit three of them up but no bites. i then hit up two nearby regulars and one somewhat nearby new guy.  none were free.  i'm starting to feel frustrated.  i'm surfing the sites and i'm not getting any hits.  this sucks.  so much rejection in one day sucks and its starting to get me down (though i know better...)

its about 6pm or so and i've given up on getting fucked today without leaving my 10 minute or so radius (i even expanded it to 20 mins) and i am not up to travel so it means i'm not getting fucked.  when i notice a message from this dude who i have chatted with before telling me to come over.  the reason i haven't hook up with him yet is he's not so attractive to me in his pics, i mean he's ok but there is something about him that has held me back.  however as i said i'm horny as hell, i'm having no luck today, and he is local, definitely within my ten minute biking radius. 

letting all of that get the better of me i tell him i can be over soon.  i hop on my bike and it really is just a ten minute ride despite getting a little lost.  i get to his place and he is actually really attractive, my kind of sexy, he looks like he is in his late 30's, thin, tall, brown skin, long black hair, some tats, jewelry, very hot.  nice, clean place (i have a major appreciation for cleanliness).  he takes me to his room.  we don't chat much as i realize I only speak english and he mostly speaks spanish.

he starts kissing me from behind.  i turn around and we kiss long and hard.  he is a really good kisser.  he lays back on the bed and we kiss and grind.  its very hot.  i pull of my shirt and he says 'wow'.  he places his lips around one of my nipples.  plays with my nipples for a while - i luv it.  then he pulls back for a moment and says, 'can i ask - you are man to woman or woman to man?'.  clearly our language barriers may have confused the situation, so normally this would be a very unsafe moment however he's really nice and clearly into me so i say "woman to man".  he says, "oh, nice" and proceeds to suck my nipples more.

i reach down and pull off his pants.  he has a huge thick cock.  i pull off my shorts, i have a second of nervousness, worried that maybe our inability to communicate verbally might mean what i have in my pants is not what he's expecting, however its fine.  as soon as i pull them off he reaches for me and pulls me on top of him.  we kiss and grind.  i kneel down and take his cock into my mouth.  he moans as my lips wrap around his thick cock.  i go at him for a while.  then he leans down and pulls me up, turns me onto my back and sucks my clit.  he is very good.  i'm very turned on and he's hard as a rock so i grab a condom and slip it on him.  i mount him slowly as he's big.  then i ride him grinding against him til i cum hard.  he flips me over onto my back and pushes into me, he's gone a little soft so he pulls out and strokes himself while he sucks my clit.  hot.  we fuck like this for a while.  he fucks me for a bit, i suck him off, he sucks me off while stroking himself.  he seems to be having trouble staying hard, but i don't care, the fucking is really good.  we fuck like this for about an hour.

afterwards i don't even bother to clean up, i mean i'm ten minutes from home, as i am leaving we make out at his door - very hot.  i bike home with his cum still drying on my chest.  

i could kick myself.  i can't believe i waited so long to hook up with this dude, clearly i let my lookism get the better of me, and i don't know why i never learn that people rarely look like their pics.  i could have been fucking this guy for months.  really my ideal is a hot fuck bud who lives a block away but i'll settle for a ten minute bike ride.

this dude and i hooked up a few more times, maybe 2 or 3 don't remember.  but then he started to get weird.  when i would say i couldn't swing by that day he would send angry messages.  now there is really no need for all that.  so i decided that i needed to let him go.  now i've let a few repeat hookups/regulars go in the past.  one dude it was because he just stopped being fun to play with (for reasons i'll save for another piece), one dude started to get very clingy and clearly wanted more than nsa, another dude was extra flaky.  

with this dude i felt worried that an outright i'm not interested anymore will escalate him.  i mean he doesn't know where i live and he has my cell (but he only uses it when i'm coming by i think he forgets he has it and i could always change my number if needed) so there is not a whole lot he can do but still. 

so i just keep telling him i can't come over.  however this does not work and he keeps trying and one day just says 'look if you don't want to see me again just tell me'.  i decide to do just that.  i send him a message just saying, i had fun and you're a good guy but i'm not interested anymore.  he sends me a series of angry messages back which i ignore.

the next day he messages me again like nothing happened asking me to come over.  ok this is too much.  so i block him.  a minute later i get a message from a different user name on the site - i open it and its an angry message from him.  wtf.  i block that user name too.

luckily he does not have a third user name and my blocking of him succeeds in cutting off contact.  however he still checks me out on the site now and again.  creepy.  gotta trust my instincts more.

queens

lately i've been hooking up with a lot of queens.  in all of the gay boy sense of the word.  to be clear that is how these guys self identify, well most of them.  

so i've fucked a good number of dudes.  bi guys, 'straight guys', a few queer guys, closeted guys, heteroflexible guys and of course gay guys, however queens are a particular type of gay that i do luv.   I would even go so far as to say that queen is another gender, but that is not for me to say as i am very far from a queen, and i am a strong believer in self determination. 

after a particularly long play session i woke up one morning not in my own room (for those who follow this blog you know that its rare that i stay the nite).  However this was a long late hook up involving public make out/groping sessions, balcony sex, and lots and lots of vodka or rum (to be honest i'm not quite sure), so it was easier to just crash.  i'm slowly coming to full consciousness and i start to gaze around the room which i didn't really see last nite as the lights were out and i was also focused elsewhere...

the first thing i see is a huge poster that says "queen" with a gorgeous person on it in full regalia, next to it on top of the dresser is a huge fuchsia feather headdress sitting on one of those mannequin heads and next to that is a Bette Midler doll still in its box on display.  As my eyes drift around i realize my hook up has a collection of Bette Midler dolls.  I almost laugh out loud however the hookup is right next to me and i don't want to disturb his beauty sleep, i believe i may be in one of the gayest rooms i've ever been in.  

the fact that i've been playing with alot of queens lately was not intentional, it just happened, actually it just recently dawned on me this queen trend i have going. 
 
so this may seem ridiculous to some but how i realized my queen trend is because i have very little fashion sense.  its not something i follow and i was not one of those people born with inherent style.  i put little thought into the clothes i wear on a daily basis.  what i've come to realize is that this is pretty unacceptable when in the company of a serious queen. 

this one queen i've been fucking pretty regularly.  as a result, i'm even more relaxed.  you like me, i like you, eventually all the clothes are gonna come off, what does it really matter what i have on.  so one nite we meet up and i'm extra extra casual, tank top and old ripped stained sweatshorts, he show's up in polished leather boots, a white button up, suit jacket with a silk red handkerchief folded carefully in its pocket.    now he's a brand of queen that actually would not say anything about what i'm wearing however, i think note to self, next time at least wear shorts that don't have a big stain on them....

this other queen that i've been playing with is the kind of queen who will let you know right away what's wrong with what you're wearing.  the last time we hooked up he said, 'honey, you are dressed like either a lesbian or a fat trucker' - in addition to the sizeism and sexism, some would take offense to having their outfits critiqued.  i however totally acknowledge my lack of fashion sense thus highly appreciate any feedback i receive.   

i'm not saying that i'm gonna change how i dress to suit my hookups, however being in the presence of high queens so often these days i do feel the need to at least up my sense of fashion, at least a bit, well or at least wear clothes without stains.

the giant cock

i don't really know where to start about this hookup.  this guy and i had messaged some earlier that day.  it was friday night and i was just relaxing at home kind of looking for a hook up but also very content to just stay at home and chill after a long week.  i was chatting with a couple of guys on line and also a regular or two via text.

dude is ok looking in his pics.  like it could go either way.  however this is how he gets me.  i'm the kind of guy who likes variety.  sometimes i like a rough dom/sub fuck other times i like a slow sensual screw.  lately i have a good number of rough types and i don't have any sensual (i used to have a sensual fav but no longer...).  dude says he's a sensual kind of guy.  so this gets me.  its kind of late and i could easily stay home but i decide to go for it. 

i get to his place. nice place, but messy, bordering on needing to be cleaned (as folks who follow this blog know i have a thing for clean apartments).  he's ok looking, to be really honest i can't remember what he looks like, kind of hippyish white guy, can't remember his face at all for reasons you are soon to find out.  we chat a bit then start to kiss and make out.  its very slow and sensual... perfect.

we both strip and that's when i see his cock.  its gigantic.  i luv a thick cock - however this dude is gigantic no other word to describe it.  he didn't have a cock pic in his profile nor did his profile mention his size so i'm a bit shocked.  i bend down to blow him and i can barely get my mouth around it (no joke or exaggeration).  i try to suck him off but really i'm just sucking the head, its all i can do.

i know that my cunt will be able to do better (at least i hope it will) i reach for my condom supply and pull out a magnum XL.  he smiles and says great i have some of those too.  however when he puts it on it is clearly too small, like the magnum XL is squeezing his poor cock.  i say this to him and he says yeah, the only condom that fits him actually is this pricey japanese brand so he makes do with these.

i push him onto his back cuz i'm clear i'm gonna need to take my time.  i guide him into me a bit at a time, taking it slow, it hurts he's so big.  then he's all the way up in me.  and it hurts but i really want it.  then my cunt opens up to him and he's stroking me, its pain and pleasure at the same time, my cunt expands more to take his cock and now he's stroking me hard and i'm loving it.  we fuck for a while no where near how long i can usually go but now its really just starting to be painful.  i stop him and he pulls out and begins sucking me off.  he blows me for a bit, i blow him the best i can.  he asks if we can fuck again i say i just can't i'm sorry he's cool with it.  he lies me on my back and spreads my legs.  he begins fingering my cunt, i move his finger up so he's stroking my clit.  then he begins jerking me off.  he watches as his fingers stroke my clit, he seems fascinated, just gazes intently as i moan.  he strokes me until i cum hard, one of those eyes in the back of the head kind of cummings.

then we lay back and rest.  i believe at some point we both dozed off.  i woke up to feel his fingers tweaking my nipples and his hard cock rubbing against my ass.  i moan and grind back.  he still has not cum so i grab some lube and jerk him off.  he's hard as a rock and i wish i could fuck him more but i know that i'm already sore as hell.  i hand job him for a while, my hand looks so tiny around his cock.  then i kneel between his legs and suck his balls.  he reaches down and replaces my hand on his cock with his.  strokes himself while i lick at his hairy sacks til he cums - shooting all over.

we both lie back to rest.   we start chatting.  i'm his first trans guy.  he talk about how it doesn't matter, girls or guys, its all the same problem very few people can take his cock.  i feel bad for him.  i mean i'm not surprised, i don't think i've ever even seen a dildo that thick. again i am not at all exaggerating.  we cuddle and chat a bit more and i realize its 4am.  folks who follow this blog know i don't like to stay the nite so i tell him i gotta go, clean myself up and bid him farewell. 

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.