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.

more on motel fucking

so i realize that this was a risky hook up.  just want to say that from the get.  my best friend was not happy i did this.  however i've been a little bored lately and that boredom has caused my judgement to decrease....

due to work it had been six days since i had been fucked.  there was one fuck session in those six days but i don't count it because it was just ok - one of my regulars who has gotten less hot and fun lately, definitely gonna downgrade him on my list.

i had made plans the night before with "racist guy".  yeah i know why am i fucking someone who i refer to as "racist guy" however he is a really hot fuck.  so racist guy cancelled on me and we rescheduled for tonite.  got a text from him midway through the day saying he needed to cancel again.  annoying.  i have one or two regulars that are flaky and i put up with it because a) they are hot, b)  they are hot fucks, c) i like them as people despite their flakiness.  racist guy is just a hot fuck and convenient and usually available so i'm not willing to put up with flakiness.  sorry, i digress, not the point of this post

so clearly i am horny as hell.  

i had posted an ad on craigslist a few weeks ago.   not something i usually do as craigslist can be a bit of work and i'm lazy.  however i was bored.  i got two interesting hits - neither of which could host.  i prefer to travel.  but this one dude and i had been texting pretty regularly for a few weeks trying to arrange something.  hot texts.  he's a dom top which for those who follow this blog know is one of my weaknesses.

so i text him to see if he's free.  he is but not till kind of late and its the middle of the week.  however as i said i'm horny as hell and i'm not feeling like any of my regulars. 

the other thing is if we are gonna fuck we are gonna have to get a motel room.  i've done a motel room fuck before and its not so much my thing.... however this dude has got me curious and as i said before i'm horny as hell. 

so i say ok.  lets do it.

i'm nervous about this hook up.  usually i don't get nervous anymore however the combination of late night, motel, part of town i'm unfamiliar with, and the fact that he's gonna pick me up in his car at the bus stop and drive us to the motel all are making me a little nervous - ok more than a little nervous. 

but i want it.  so i make sure i have enough cash for a cab if needed, text my safety bud the hook up info, and head out. 

he picks me up at the bus stop.  he's attractive, has that roughneck look and vibe.  we're chatting on the ride over to the motel.  the vibes cool.  he's never fucked a trans guy before but has fucked trans women.  he asks if i've hooked up in a motel before, i say yeah and i wasn't so into it.  he said well maybe after tonite you'll change your mind. 

we get to the motel.  its clearly a hook up motel.  he tells me to get a room and he'll give me cash for half and to text him the room number and he'll meet me in the room.  this dude is very dl

the last time i did a motel hook up the dude paid, but the motel owner made me show ID cuz he thought i looked too young....  so i'm nervous getting the room.  however i get a room for a few hours, no ID needed at this place.

i text him the room number.  he comes into the room and turns on the tube.  there is porn on the tube.  lol.  this place is clear about what's its used for.

we strip.  he's hard, smaller than i expected but that doesn't matter to me tonite.  he tells me to suck his cock.  i take him into my mouth, blow him for a while, he face fucks me hard and rough, but i need to get fucked and i tell him so.  he grabs a condom and plows into me.  fucks me hard - which is how i like it.  the room has a whole wall of mirrors so i watch as he fucks me.  he pounds me pushing my legs over my head, holding me down, slaps me around a bit.  hot. then pulls out and cums on my face.

there is an element of danger to this that keeps me a little on guard and not totally relaxed, like i don't know this dude and something about being in a motel makes me feel more nervous.

we both rinse off.  then he says ok, lets go.  i say, really?  Your only going to fuck me once?  He says ok, suck my cock.  i blow him for a bit, he's hard again.  I say fuck me.  He says no, suck my cock, do as i say.  Hot.  I suck him off some more then say again "fuck me".  He says no.  I suck his cock some more.  Then i ask again, "please fuck me".  He responds by slipping on a condom picking me up and slamming his cock into me. 

I ride him for a while then he turns me around and pushes into my ass.  He holds me down and pushes my head into the bed as he rides my ass, i'm moaning and grunting, rubbing my clit as he pounds me.  He's pushing my face into the bed, he's much stronger than i am, its hot, however there's a moment when i think what if i want him to stop and he doesn't, i realize my vulnerability in these moments, however when i push back he lets me up, I turn around, pull off the condom and grab a new one.

i say i want you in my cunt.  he slides into me, fucks me hard and rough, pushes my legs up over my head, pounding into me, i'm watching him fuck me in the mirror.  so hot.  he pulls out and cums all over me.

he gets up and hops in the shower.  when he's done i do the same.  now i'm starting to feel nervous again, what if he just takes off and leaves me in this random ass place.  however he doesn't.  i drop the key off and he picks me up outside.  we chat as he drives me to the bus stop.  he asks if i fuck alot of girls.  i say have in the past but now mostly dudes.  i ask if he does.  he says yeah with a grin.  he runs a bar so he says he gets alot of offers.  i feel like we are having some convoluded, sexist, male bonding type of moment.

he drops me at the bus stop, i have to ask him to give me half the money for the motel room, but he does without trouble.  i hop on the bus and trek home.

my first time

I had seen his ad on Craigslist something along the lines of bio guy looking for an ftm. I had just started exploring the world of anonymous play with non trans guys, but had yet to actually do a hookup. I had been surfing the net a lot – reading mystery fag and transfag blogs which are hot if you have not read them check them out. I also had read the safer sex for trans guys guide a ridiculous amount of times. Nerd that i am i had done my homework.

I had posted on Craigslist and gotten a lot of response, a few interesting, a few creepy, and a lot in between. I was on Manhunt and Adam4Adam but in a very tentative kind of way which for me looked like a clothed pic and blurry face pics and a profile that didn’t say much. I had chatted with some guys, but I had yet to set something up.

His ad said he’d been with trans guys before so I decided to message him. He responded right away and we exchanged pics. He was cute, late 20’s or so, black guy, skinny. We chatted for a while exchanging a lot of emails. So he said when you want to meet. I was pretty nervous about it all, but there really wasn’t anymore to say via email, I put it off for a bit, but then decided to just go for it and we set a date.

That night I put on a cute outfit, made sure I was bound up (i used to worry that because i have not had top surgery it would turns guys off but that has not been an issue so far), trying to look as 'guy' like as possible, I headed out. I was nervous but excited.

When I was a few blocks from his place I texted him, he said he would meet me outside. I got to his place. He looks different than I expected, extra skinny, very gay, not my kind of hot, but not unattractive, he just got off work so has on a button up and slacks. I say stupid nervous stuff as we head up to his apartment. He takes me to his room which is incredibly neat. We sit on his bed and chat about random stuff. Then he says you are way cuter than your pictures. I just smile.

He leans in and kisses me. We kiss for a while, he is a really good kisser. He's very confident which i like, he unbuttons my shirt and pulls of my top and binder and unbuttons my pants, I pull them off and help him with his. I’ve been pussy fucked before, but never with a live cock. I’m nervous.

As a result, I don’t remember a whole lot about the fucking except that it was good and not long but not short and that there were some hot moments. I also let him fuck me in the ass which was incredibly painful and a little messy which I felt embarrassed about but he didn’t care. The ass fucking wasn’t particularly enjoyable and I know that at the time I did it because I felt I needed to in order to fuck gay boys.

After we fucked, we chatted more about our lives, he kept saying how hot i was, how sexy I am, how he’s sure I can get any guy I want. It was a definite ego boost. As I’m getting up to go he asks if I want to see him again, he says be honest, I’m not sure but say yes.

Heading home, I stop at a coffee shop to use the bathroom and clean up. I don’t know yet to just ask to use the bathroom and rinse off before I leave a hookup. My ass is sore, I feel like I smell like sex, I clearly need a shower. To be honest while I would like to say I was totally happy and excited, I remember mostly feeling glad that I hadn’t been killed, robbed or made to do things I didn’t want – basically I remember feeling sticky, sore and relieved that I had finally done it.

I got home, showered, and made some food. Once I was feeling a little more together I remember smiling to myself – I felt good in my body – good that I had overcome my fear and nervousness, good that I had taken control of my sexuality in a way I had not before, good to be desired and considered hot and sexy, just good in all off my little transboy gayness.

The Craigslist Hook Up

One of the least enjoyable aspects of the anonymous sex scene is what I refer to as the "setting up" stage. The moment when you're horny as all hell and you've exhausted the million different ways to fuck yourself with your favorite dildo and you're way overdue for someone else to be wielding a cock in your general direction. So you hop onto one of the sites - craigslist, adam4adam, manhunt, etc. Some sites are more effective than others. I've tried all three of these with varying success.

Craigslist is a "you gotta work for it" kinda site. First there's the ad development phase. You have to decide how you want to describe your "trans-ness". Using terms like FTM, Trans Man, Trans Boy, has to be a deliberate choice, because each term draws a particular type of "gent". If you describe yourself as "FTM", you're more likely to draw a guy, for whom attraction for trans men has been tried, tested, and proven to be true. He can actually say "female to male" without tripping over words and looking seriously confused. This is my favorite kind of CL hook up because the sex is usually hot. If you describe yourself as a "Trans Boy", then expect the "daddy" types to hit you up. For some reason, the term "Trans Man" draws a lot more guys who are actually looking for trans women. Go figure.

Once the ad has been placed and the responses start trickling or rolling in, then the real work begins. Some men aren't scared to air their shit - they'll send cock pics right away, want to meet that day, and eagerly list all the many dirty things they'd like to do to you. Others are shy and hesitant. They're usually living a totally straight (and narrow) life with a girlfriend or wife, so every once in a while they gotta get a little kink in their life and that's where you come in. I generally steer clear of these guys, because, well...there's just too much potential for drama. Then there are the fools who, even after you've been clear about what being a trans guy means in your ad, you've emailed back and forth about this, they've seen your pictures (face and torso), they know about the facial hair, somehow after all this they're expecting (hoping and praying for) you to look more like a butch woman. I can tell you from experience, very rarely does meeting up with a guy like this result in sex (or even good sex). Once in a while, yes, a dude surprises the hell out of you and you walk away all glowing and shit, but most of the time, it results in nothing or nothing to write home about. You may have to wade through tons of responses from CL, a lot of them icky, and really only find one guy that you'd disrobe for, which is quite common, as well as time consuming! So, yeah, the CL hook up usually requires a lot of work.