As I finished my makeup I stared in the mirror at the woman now known as Danielle. Some would argue I wasn’t really a “woman” in the biological sense. However, years of HRT, breast augmentation, sissy training and self feminization had resulted in a very convincing facsimile of one, save for the male genitals I still retained. I was older, but I kept myself in shape, and I would consider myself pretty for an older woman if you didn’t look too close. Dim lights and candlelight did the rest.
After a few years of unsuccessful dating, I discovered many “straight” men harbored secret sexual desires for “girls” like me and were willing to pay handsomely to indulge in their fantasies. With guidance from a friend who was also transgender and had become an “escort” herself, I became an “escort” as well. Most of my clients were men but a few were women. Each had their own preferences and differences. Some clients wanted only companionship and cuddles, and others liked to act out their kinkiest fantasies. The rest fell somewhere in between. Tonight’s client was “Mr. M”, as he liked to be called.
Mr. M wasn’t unattractive, but I wouldn’t call him handsome. A local businessman, he was your typical fifty something male, married and a bit chubby but not too much. Like most of my male clients, his wife supposedly wasn’t very responsive to his romantic desires. That’s where I entered the picture. I participated in those fantasies (with some boundaries). We met by referral from another client, and Mr. M had been a regular.
One interesting attribute of Mr. M was his manhood. His package wasn’t particularly long, but it was incredibly thick, with a bulbous, perfectly formed head. He was a bit crude and rough in the way he liked to be pleasured, and liked to be demeaning. Again, not uncommon amongst my clientele. He was very generous when I showed enthusiasm while providing whatever pleasure he demanded. The last session we had surprised me, and honestly made me eager for the next.
It started as usual. He arrived early and demanded a drink. He had specifically asked to see me as a blond in a black lace teddy and high heels, and with the help of a long blond wig (I was a brunette naturally), I became a blond.
I made him a drink, a Jack and Coke, while he undressed and took a shower. When he came out of the bathroom and was toweling off, I could see his cock was already at full attention. He spread the towel on the couch and sat down, taking the drink from my hand.
“Well, what are you waiting for, bitch? My cock isn’t going to suck itself!”
I slowly kneeled and spread his knees apart, staring into his eyes because I knew that turned him on. I grabbed his hot throbbing cock and slowly ran my wet tongue around that huge head. I began stroking him as I made my way to his balls, licking and slowly sucking each into my mouth. After running my tongue up his shaft, I kissed the bottom of his cock before taking him into my mouth.
I covered his cock with saliva as I sucked enthusiastically. He was so thick I really had to force my mouth wide to suck him off.
Mr. M’s head fell back as I sucked his cock. His moans increased and his thighs quivered. When he was with me, he always called me “Sandy”. I learned that was his wife’s name. He kept saying her name as I sucked him off. Whatever.
As he approached orgasm, he growled, ”Deep throat me, you whore!” I began to take him down deep past my gag reflex as he forced my head down on his cock. I took him down to his balls just as his cock began to spasm and he yelled out, ”Take my cum, you bitch!”
I could feel his hot cum shooting down my esophagus as he unloaded. When his cock stopped spasming, he withdrew his cock from my throat. His cum dripped from the head of his cock onto my chin. He used his finger to wipe the cum from my chin. I eagerly licked off his finger. I also licked off the cum on the head of his dick.
Then he did something totally unexpected. He told me to get on all fours on the floor. I didn’t think he could fuck me so soon after ejaculating but I was his for the next hour and he could have whatever he wanted.
He positioned himself behind me on the floor and began kissing, then gently biting, my buttocks. “This is something new,” I thought to myself. He grabbed a tube of lube and dripped a gob between my cheeks. He began to finger my asshole as he continued biting me. Then, he began tonguing my asshole, first licking around the rim then slipping his tongue inside me.
I had anticipated him fucking me so I was clean and ready for him. I wasn’t ready to have someone eat my ass out. It was rare to have a client intentionally pleasuring me. I trembled from the sensation. He stroked my little dick with his well lubed fingers as he ate my ass.
As he continued to drive me wild tonguing my ass, he regained full erection at some point and grabbed me roughly by the hips. He pressed that huge cock against my lubed asshole and when he popped in, i cried out from the jolt of pain I felt taking such a thick cock inside me.
He paused to let my body adjust to him before slowly fucking me with that thick dick. I’d taken some large cocks before, but nothing as thick as Mr. M’s. As my body adjusted to him inside me, he would gently slide in me, then almost pull out before burying his meat again until I felt his thighs against my ass. He began fucking me with vigor as I stroked my own little dick. Finally, I couldn’t hold back and began to shoot my own cum onto the towel on the floor.
“That’s right, cum for me, Sandy,” he said.
Mr M. kept plowing my ass, grunting and sweating. He would occasionally slap my ass and say, ”You like that, don’t you, whore?” as I breathlessly said, “Yes daddy, fuck me good! Fuck me more!”
Mr M. groaned and filled my ass with another load of hot cum. He stayed inside me for a minute or so before pulling out, kissing my back and neck. I could feel his cum spurting out of my ass and down my balls as I stood up to clean myself.
Appearing totally satisfied, Mr M. showered and dressed and had another drink before he said he had to go home. I kissed him as he was leaving and he handed me the usual envelope as he stepped out of the door. I opened it and saw that he left me a very substantial tip.
I can’t wait to see what Mr M. has in mind for our next date.