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