“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.”
“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.