The Wild November Night


The outcome of my meeting with the board was successful, we were to proceed with the multi-million dollar project, and all the work was worth it. Now all that was on my mind was my date with the escort, the tranny escort. As I drove home, I couldn’t help but feel the chill in the air, it was one of those November nights when autumn was morphing into winter, and I loved nights like this, they only made the wildness more memorable.

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I weaved past the front gate and settled the Porsche to rest in front of my mansion. As a young millionaire, I had done well for myself. The CEO of a grand real estate group surely had to live in a mansion.

I opened my front door where a family of giraffes could pass through and stepped into the house. High ceilings, marble floors, expensive gadgets, a mini-pool, state-of-the-art decorations and furniture were just simple ways to describe the components that made up my home.

I saw myself in my bedroom where I got out of the expensive Hugo Boss suit I had on and saw myself in the bathroom. It was around 9 pm and the tranny would be arriving in one hour. I put the house in order, heated the pool a bit and ordered Chinese, I had a bottle of Cristal to go with it.


She arrived about forty minutes later, earlier than I expected. She was a beauty in every sense.

About 5’6, red-head, a slim body that screamed gym freak, big boobs and a perfect ass, the most gorgeous tranny I had ever seen. She flashed a smile at me and told me to direct her to the bathroom so she could prepare.

She came down a while later in a bathrobe, the same as I was and we headed to the pool where a mini table was set with Chinese food, fruits, a bottle of red wine and my favourite, Cristal.

We made small talk as we ate and it was there I got to know she went to college but loved her work as an escort. We talked for a while before we made our way to the pool. At the edge of the pool, she placed her lips on mine almost surprisingly, tugging at my lower lip for entrance into my mouth, our tongues working together as a small moan of pleasure escaped her lips.

She moved back and undid her robe slowly. From her beautiful slender neck to her perfect tits with pink nipples, down to her flat tummy and to her semi-erect cock, she was perfect, her cock would have been about 6 inches if I were to guess.

I stood there staring at her amazing body. “Take your robe off..”, she said with a smile plastered across her face. I happily obliged, letting the robe lose in one swift movement. Now I was handsome in every sense, 6’2 with a well-groomed beard, a ripped torso and an 8-inch cock, her eyes were glued to me.


I laughed gently, I had created an impression. We stepped into the pool slowly as we continued our kissing, hands roaming bodies as our mouths kept working. I kissed her all over, her neck, boobs, and nipples and I reached down to stroke her cock.

I was rock-hard and needed to bury my meat in her ass. I turned her and bent her over, holding the edge of the pool. I parted her ass cheeks and slowly stuffed my 8-inch cock into her asshole. She moaned in pleasure as my length settled into her. I fucked her slowly before she suggested we head back into the house.

This was so much better than watching a tranny on webcam the reality was better than I had ever imagined. The thought of her self-sucking was going to be a real treat and a huge turn-on for me I was just waiting on my moment, after all, she did mention on her online profile that she was a self-sucking tranny so she needed to live up to that reputation.

We went back and up to my bedroom, our robes abandoned beside the pool. We continued kissing before I whispered in her ear,

“I want you to suck yourself”.

She smiled at me as she made her way for the bed. She scooted down the bed about halfway then raised her legs up and over her head. She bent a little and her cock was right there dangling in her face.

I just sat there with my cock in my hand as her lips parted way for her stiff cock. She sucked gently at first, going slowly as the veins around her cock glistened with saliva. Gradually she increased her tempo and sucked harder, she was moaning but the cock stuffed in her mouth couldn’t let her moan with free will, it was obvious, she was turned on as hell.

I just sat therebeating my own cock, masturbating to the delight before my eyes. She was now sucking hard, the luxurious sensation that must have caused would be delightful. I was feeling the churning deep within me, the pressure was building, and I was going to cum soon.


And then time slowed down, a loud moan escaped her lips somehow, she was cumming. I could see part of the cum dripping down the edge of her mouth, spurt after spurt, sucking and cumming in perfect synchronization, it was the most beautiful sight. My balls tightened almost immediately and I shot my load of cum right in front of her, groaning as the last drop of semen made its way out.

We gave ourselves a moment to catch ours breathes before she descended on my cock, devouring and sucking with raw passion. I could feel the tip of my cock hit the back of her throat as saliva dripped down my cock to my balls.

Her head game was strong, that I admit. She then whispered to my ear,

“…I want you to fuck me like our last night on earth”.

I put her on her back and spread her legs as my cock made way for her asshole. I entered with ease as she was already prepared. I pounded her ass as I had done to no one. She was wilding, throwing her arms everywhere and moaning in ecstasy. I bent her over on all fours as I continued pounding her ass,

‘kpack, kpack, kpack!’

were the noises audible as our bodies slammed against each other. My whole length was going on, full penetration, balls deep. I wasn’t going to last long, my balls tightened as I shot load upon loads of cum into her ass.

We collapsed on the bed and I could see she was covered in sweat. She reached for my cock, stroking as she spoke, “I don’t even know your name”, she said while laughing.

“Its Phil, Phil Macklemore”,

I replied smiling.

“Mine’s Jane, Jane Peters”,

she replied still laughing. We continued laughing and it was there I knew we were going to do this often. Being able to watch a sexy shemale sucking her own dick was a massive turn on to me and one I would like to repeat, watching her legs behind her head as she sucks up and down and looks me in the eye at the same time. She asks me

” have you ever seen a shemale suck their own cock”

I replied

” No i have not”

Jane laughed and stared at me and said she would be happy to let me sit back and watch her close up, she even said I could take some pictures of her and learn from her. I was hooked, I was fascinated, I had never experienced anything quite like this before. I have seen movies or videos on the tube sites but never have I ever been up close and personal and being able to hear her saliva dripping down that cock, the slipping hand as it runs up and down, and watching her cum in her own mouth was a massive turn on to me and one I will be back to repeat time and again

She’s The Boss – Sexy Transsexual Story

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