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

My House Boy

“I'm a simple transboy with simple needs. I like my apartment clean and my dinner waiting on the table for me when I get home from work. I also like my dick sucked as soon as I walk through the door. You on your knees welcoming me, that's all. No words exchanged. If this excites you and you're interested in doing this once a week (on a week day) say around 5 to 7pm, then send a pic, a few sentences about your service work experience and your love for trans cock, and dates/times you're available for an interview. We'll take it from there. This is not an offer for a paid position.”

The responses to my craigslist ad are many, varied and oh so fascinating. Some guys want me to slap them around and call them slut, etc. Others want to be ‘forced’ to lick dirty floors. And there were the ones who want to be ‘forced’ into certain clothes, like lingerie. There were quite a few of these guys actually, which really got me thinking about how I don’t weave enough sexy underwear and clothing fuckeries into my sex life. I plan on changing this.

When I find the right guy, I know by his ass pic. It’s so deliciously round. He’s a cute white boy, mid-twenties, average build.

“You’re to call me Sir,” I text him soon after he makes the horrible mistake of referring to me as “mistress”. I nearly lose my shit. I very nearly call the whole thing off. But I choose to proceed. The sadist in me wants this silly white boy to scrub the hell out of my bathroom floor for such an infarction.

For our first time playing I want to keep things really simple: strip down to jockeys, clean the apartment thoroughly, and save the bathroom for last where, after scrubbing the tiled floor, I’d peel off his underwear and fuck his ass.  

“I like the American Apparel jockeys,” I told him on the phone. Those white bands, the dick hole…hot.

When he eventually came over later that night, I’m on my couch, pretending to be engrossed in a book, barely acknowledging his presence. Out of the corner of my eye I see him strip. Broad shoulders and a cute little belly. The round ass comes into view, encased in tight black jockeys. Yeah I couldn’t wait to play with that…

All the cleaning supplies were laid on the dining table. As soon as he was sans clothing, he donned on the yellow rubber gloves and got to work. And it pretty much was work, cleaning my tiny ass kitchen, mopping the floors of the living room, vacuuming, dusting. At some point things got too loud, so I yelled at him for that.

“I’m sorry sir. I will try to keep it down.”

I asked him if he wanted me to fuck his ass tonight.

“Oh yes sir,” he said with relish.
“Then you’ll do more than just try.”

“Yes sir,” he went back to his task, which at that moment was swiffering my bedroom. After that he’d ask permission when he had to do something loud like run the vacuum cleaner. At some point I started getting hornier and impatient, so I ordered him to hurry up.

Eventually he was in the bathroom, scrubbing away at the tiles, his cute ass bobbing in the air. I go put on my strap and grab the lube. I’m so excited it takes a couple tries to get the strap on right. This has been a fantasy of mine for ages. One I always pondered the roots of and interrogated and came to realize, as well as accept, that my kink will always be informed by the myriad complicated experiences that have made me me. The truth is I’ve always liked to involve power play in fucking. There is something about being dominated that drove me wild. Of late, as I’ve been fucking people of other genders, not just cis men, I’m discovering the dominant me.  And this part of me likes to fuck hard and rough. This part of me likes to restrain, spank, bite, and say the most perverse things (consensually of course.) When I’m in this frame of mind, I love a worshipful lover – one who has no qualms being on their knees before me and letting me do all sorts of pervy things to them.

He’s still on his knees, when I enter the bathroom, hanging onto ledge of my tub. I lower and get behind him. His dick is hard and he does this gaspy sound when I first touch it. I guess the lube on my hand is cold, but things quickly warm up as I start jerking his dick hard and fast, pre-cum seeping on my hand, so much so that his dick is coated in seconds. Wet jerking-off sounds fill the air and I get really wet because wet jerking-off sounds are the most erotic thing ever.

“You dirty boy. Look at how much you’re dripping.” I’m bent over his back, whispering in his ear. His moan is deeper this time.

My other hand is rubbing his ass, slipping in the crack. After lub-ing, I start to play with his asshole. My forefinger slips in.

He’s squirming around, twirling his ass in enjoyment.

“You want me to fuck this ass?” I ask while slowly finger fucking him and he groans deep.

“Yessir…” is all he can manage. He displaces my hand on his cock and starts jerking it furiously.

“You want my cock to open up this ass?” I slip out my finger and slide my 7.5 incher in and he moans “fuck” really loudly in response.

I love a responsive bottom.

I go slow and shallow at first, not wanting to cause any unnecessary pain. Head only. Then head and a little bit of shaft. I watch my dick go in and out of his ass. The sight is intensely hot and I just want to pound. I so want to, but we fuck nice and slow for a short bit, while I rub his ass, lick and bite his smooth back. Eventually, he’s ready and what ensues is nothing short of primal fucking. I grab his ass hard and just pound, letting loose this thing that I didn’t even know was in me.

“Oh…yes…sir,” he’d whisper every once in a while in between weird and erotic moan-y emissions I couldn’t even begin to describe.

After I shift and slip deeper into his ass, he makes another weird moan-y sound, followed by a “I’m gonna cum sir…” and shoots cum all over the outside of my tub and the tiled floor beneath. 

Afterwards, we lean on each other, panting, for what seems like forever.

Eventually when I can manage it I get up, shed the strap, and order him to finish cleaning up the bathroom and let himself out when he’s done.

“Yes sir,” he says, still trying to catch his breath.

And that’s exactly what he did.

fighting to get tested

it had been six months since my last hiv test.  i like to get tested every 3 months as i am very sexually active (as most prevention folks will reccomend to gay men who are very sexually active).  I am almost always safe but there have been exceptions. 

3 months ago while at the doctor for other matters of the gynecological variety i asked the nurse if i could get an hiv test as i was there and it had been almost 3 months.  i keep track of these things so i know that it was basically like 3 days before it would be 3 months.  the nurse acted very put out from the moment i asked (this is a LGBT clinic by the way) and looked at my chart and said it hasn't been 3 months yet and before i could say anything else walked out the door.   i gave in and just did not push it.

i have written about this dynamic before (transfags of color are not at risk) where i assume that the nurse considers me low risk because she considers me a woman or at best to have 'female' genitals, probably assumes i fuck only women i.e. i'm a lesbian... whatever.... transphobic bullshit not to mention that non trans women who fuck non trans women also should be encouraged to get tested too...  sexist bullshit...

at this point it has been over six months and as always i'm nervous and anxious about being tested but i know its been six months and i need to do it.  i'm again already at the clinic so i ask for an hiv test.  the nurse is nice and says ok but she has to get someone else to do it as she is not certified yet.  cool.  i see my doctor and my appointment is over.  the nurse is no where to be seen.  i have to leave my exam room go find her and ask again for a test again.  she says, oh, sorry and says she will get someone to test me.

i wait for about another half an hour before finally someone comes to test me.  again this is a LGBT clinic that i know does tons of testing, its not a busy day, the floor i'm on is actually really empty of patients.  the nurse comes and she is someone i've seen before.  she tests me and i sit to wait out the 20 minutes - which of course is stressful and anxiety ridden.  20 minutes pass and i can hear the timer go off.  again no one comes for another 20 minutes which is not long but when you have already been agonizing for 20 feels like forever....  also in the past they have been really good about it and give the results right after the 20 minute period so my mind starts spinning into paranoid thoughts of maybe its taking so long to tell me because its positive....

finally the nurse walks in and says flippantly, "you knew your were negative John (not my real name)" and hands me the print out.  of course i'm relieved about the results but am annoyed by her attitude.  unless she didn't even bother to look at my screening paper work  which is possible i clearly marked that i had unprotected sex (it was one person and a particular situation) but she didnt ask so for all she knows i could have been having unprotected sex with hundreds of people.

i have never heard a gay man of color who lives in the big city that i live in say he had to fight to get an hiv test.  just feeling a bit tired of it all.

cravings

this post includes discussion of piss play in case you wanna skip it

i've been in a strange mood lately. i have not been pursuing many hookups nor my regs that often.   i've been feeling a little bored i believe.

i was feeling like i wanted something different. something i haven't done before. i don't know exactly what though

so i got on the sites and changed my profile a little

this led me to consider doing some things i've never done before....

i started chatting with this guy who is very into bdsm.  never been with a trans guy before though.  we are talking about what he is into and what i am willing to do.  then we start talking about water sports (pee play).  i have never done this before and do not want to, to each their own yuh know, its just not my thing.  a good number of guys have asked before and i've always said no.

to this dude i say no i'm not interested.  he say's too bad it could be really hot to pee on you.  he says i would pick you up and put you on your knees in my tub.  have you look up at me as my piss streams down your body.  then let you suck my cock while ur still covered in my piss.  in that moment, i think that actually does sound kind of hot and i tell him that.  we move to arranging a time to meet.  it doesn't work out on his end and later on as i'm thinking about it i wonder if i really want to.  as of writing this i'm still unsure. 

later that day, i've had a small number of offers but not what i'm craving though i'm not even sure what it is i'm craving.  I figure i will know it when i see it.  I have kind of given up on anything interesting coming through when i get hit up by this guy, guy of color, his profile pic is a humongous cock, like seriously huge, frightenly so.

he says he's in town visiting with 3 friends and if i'm into group. ok cool. this is exactly what i was looking for.

i do my usual trans 101. he says cool and emails me pics of the other dudes. they are all equally huge guys, muscular, big guys with huge cocks.

so i'm a little scared but also interested and also a little skeptical. like is this real? so i consider it. the idea is very hot. however i've never done 4 dudes at once. and these guys are huge.

also these guys are big and muscular, they look like they were all former linebackers, clearly if the situation became unsafe there would be little i could do against 4 strong dudes.

however, maybe i just need to push past my fear, this is exactly what i've been looking for. so i consult my best friend.

who's first words are "what is wrong with you. have you lost your mind." he says "the answer is no. don't do it".  

and clearly he was right. i have never chatted with these dudes before. this was a very short exchange. so many things could have gone wrong.

i gotta figure out what this craving

fucking and attraction

For folks who are following this blog, you know i have this thing where for me at least, physical attraction and hot fucking are not always the same. this has often times gotten me in trouble as it means if i show up at a hook up and the person looks less attractive then their pics I often still go for it, this is because i've had some of the most amazing hot sex and fun hook ups with people who are low on my hotness scale and i've had some real shitty sex with folks i view as hotties.

Lately though i've been having a string of not fun hook ups. I show up, the person looks way less attractive then their pics and the sex sucks. I was beginning to think that i need to let go of my theory on attraction. 

However tonight I felt vindicated - well mostly.

This guy and i had been messaging periodically on Adam4Adam for at least a couple of months. His pics were attractive, not hot, but cute in an older gay nerd kind of way (don't get me wrong i've met some majorly hot gay nerds but this guy was just ok). For some reason we had not been able to make it happen.

Finally we arranged to meet. I head over to his place which is not far but in a part of town i've never been. He meets me outside and he is less attractive than his pics and i'm thinking oh no, not again, i follow him inside. His place is small and cluttered but relatively clean (i have a thing against dirty apartments). He offers me a beer. He is a real nerd, lots of high tech stuff all over the place, a huge telescope in one corner.

He seems really nervous. He's talking non stop. We sit down on his couch and I'm kind of vibing with him, maybe its the beer, but he is starting to look less unattractive, we chat about random stuff or more like he prattles on and i insert a question or comment every once in a while.

I start stroking his arm as we talk, wanting to speed things up some, he's still chatting about random shit, admits he's nervous and i tell him don't be nervous. to be honest i can't really remember much about our email exchanges, his nervousness makes me assume i'm his first transguy.

finally we start kissing and making out. I can feel his hard on through his jeans. i unzip his pants and pull out his cock.  nice size - thick - not humongous, not small.  i slip his hard dick into my mouth and begin sucking him off.  he's the perfect size for me to take him down my throat so i do.  he groans.  after a while i stand up and take off my clothes.  he strips as i lie down on his bed.  he climbs on top of me rubbing his hard cock against my body.  we both moan.  i hand him a condom and lube him up.  he is on top of me missionary style.  i guide him into me.  'oh god' he moans as his cock slips into my cunt.  he starts stroking me, his cock thrusting.  i grab his ass pushing him as deep into me as i can.  he grabs my legs and pushes them over my head pounding into me.  i can feel myself starting to cum as he fucks me hard and fast. 

he fucks me two more times, long hot wild fucks, multiple positions - missionary, seated, doggy style, etc., i cum repeatedly, after the third he asks if i can go another round, normally i can, but tonite i'm tired and just can't.  the whole time he keeps saying how hot and sexy i am, complements my body, says he loves my masculine smell. 

hotness

'its like you're just any guy i invited over to fuck'

i did this new fuck the other day.   dark skinned guy of color, late 20's, stereotypical gay boy hot.  he only fucks boys, i am his first trans guy.

i get to his place we chat some, usual pointless prefuck chat then we get to fucking.  he is also a dom top - which for those who follow this blog know is a love of mine.  he is sitting back on his couch shirtless, toned chest, just a pair of shorts.  we start making out.  i'm rubbing his sizable cock through his shorts.  he pulls back and says 'you want this' looking towards his cock.  i nod.  he unzips and pulls out his dick.  he is already hard.  'suck it' he says.  i kneel between his legs and take him into my mouth.  he groans.  i slide my lips up and down his cock then take him down my throat.  after a bit he stops me he reaches down and pulls of my shirt then pushes my head back towards his cock.  he plays with my nipples as i suck him off.

'can i fuck that' he asks.  i nod.  stand up.  drop my shorts and grab a condom.  'sit on it' he says.  i slip on the condom lube him up and straddle him.  i slowly slide my cunt down his cock.  he moans as i take him in.  then i ride him.  sliding up and down his hard dick.  taking him in fully.  riding him hard.  'lets go to the bed' he says.  i nod.  slide off him and lie back on his bed.  he kneels between my legs and pushes his cock into me.  fucks me hard, our bodies pressed tightly together, his hips slamming between my legs, i'm gonna cum he groans, 'cum man' i say.  he fucks me faster and harder til he groans and shoots.

this was a good hot fuck.  however there are two things about this hook up that i loved and they both occurred after the fucking.

after he fucked the hell out of me we are lying back in bed chatting.  during this usual post fuck chat he only asked me one question related to me being trans, he asked when i started to transition, then he never mentioned it again.  i think this struck me as interesting because most gay (not bi or 'straight' or queer) dudes that i've hooked up with who have never done a trans dude before at least ask a few more questions or refer to me being trans in someway.  i say this to him.  he says, 'well, i thought the trans thing would be really different, but its not', he says it almost with a bit of disappointment, he says, 'its like you're just any guy that i invited over to fuck'.  i kind of luv it. 

the second thing was that after we fucked we hung out and chatted for a while over a drink on his balcony.  it was a warm summer nite.  we were not really vibing in that way that sometimes i vibe with my hook ups, where you both find each other interesting, yuh know where there is just that connect.  however he's a nice guy and neither of us have anywhere else we need to be.  we don't really have much to chat about as we have almost nothing in common.  so we start swapping hook up stories.  i majorly luv swapping hook up stories.  we chat for a good hour or so sharing tales.  worst hook up, weirdest hook up, hook up that he wanted more out of, hook ups that want more out of me.  he gave me advice about this hook up that i've been wanting to let go of.

for me often hook ups are pure fucking, usually there is some general chat, but its really just about fucking.  sometimes we vibe and connect more strongly though its still about fucking.  and sometimes a hook up is really just about two people making a connection and enjoying each others company in that moment, and not asking anything more of each other.

transphobic rejection

i had to go to this book launch for my job.  gay event.  lots of queers around but mostly of the lesbian variety.  i'm hanging by the appetizer table pondering the scattering of mini carrots and cheese that make up the snack table when a sexy dark skinned dude walks up to me.  compact build, muscular, tight fade - cute.  he reaches out his hand and introduces himself.  we chat for a good hour or so.  just random chit chat about our lives etc.  neither of us seem to know a ton of people at the event so its nice to have someone to chat with. 

at some point during this chat i realize dude's totally hitting on me.  cool, he's nice and cute and i'm always up for some fun.  i normally arrange my hookups online but what the hell.  we talk about where were from, family, what we like to do for fun, etc.  every now and then he makes a comment about how sexy he finds me which makes me blush.  he asks for my digits so we exchange contact info.

later that nite i get a pretty lengthy text from dude about how into me he is and that he really wants to hang out and get to know me more, am i free the next night to go to an event with him, that kind of thing.  cool.  a little excessive but whatever.   this could be fun. 

however, somehow i kind of forgot about the trans bit. 

i don't know why, but when we were chatting and flirting at the event it was just fun and i really seriously forgot that dude doesn't know me, he didn't really know many people at the event so wouldn't have been able to ask about me, as a result its very likely he doesn't know i'm trans and thinks he's talking to a bio dude.  when i got his long text i realized i wanted to make sure dude knew the deal so i texted him back that i'm a trans guy and just wanted to make sure he knew. 

i never heard from him again. 

this really bothered me.  my best friend was like, whatever man, he's just a transphobic ass.  which is true.  i mean rejection always sucks but its not like i was all hot and bothered for dude or overly interested, i'm not desperate for a hook up right now, i thought he was cute and we could have a little fun together.  that's it.  its also not like i have not been rejected by guys before for being trans - i cannot count the number of times dudes have cut off communication or sent a polite rejection on learning my ftm status. 

so why did this particular incident bother me so much?  i think what it was about this interaction is that dude was really into me on a level of physical attraction and mental/emotional connection.  it was clear from our hour long chat at the event and his text after.  in that moment of flirting we were just two gay guys hitting it off and it was fun and sexy. 

in that moment i really just forgot that while i am a guy and gay as all hell that to some people i will never be a 'real guy' in their eyes.  one they can flirt with, date and/or fuck.

i really just forgot.  and that forgetfulness was kind of great.  

on the day to day i pass pretty easily.  and i work to hold the privilege in that.  however i'm always thinking about my transness whether its at the line at the store wondering what pronoun the teller will use or at the gym trying to shower or just walking down the street.

at this event though i was in a queer space that i knew to be pretty trans friendly.  thus i felt pretty comfortable and relaxed.  i also have met, chatted, fucked enough non trans gay dudes who have no issues with the fact that i'm trans that i've perhaps become over confident.   

when i'm online looking for someone to fuck its feel different.  i think its because its really all about fucking, its about a physical/sexual attraction based on looks, its about bodies and body parts.  if there is a connection beyond that all the better, but i don't and most people on those sites don't expect more.  so if a dude doesn't wanna play around with my particular anatomy as long as they are respectful it almost, not entirely, but almost feels like what i imagine it feels like when people choose who they are gonna fuck based on the type of cock they prefer.  fucked up but par for the course i believe in the world of online hook up sites.  

this rejection felt different and it pissed me off.   

when it comes down to it what really bothered me was that we were having a real person to person connection and it was a just an unwanted reminder of how quickly what happens to be between my legs can always change that