This is my first attempt at writing a story so please bear with me and excuse my mistakes as I am sure there will be many. I hope that it is an enjoyable read, and please feel free to comment and or send feedback. Thank You.
This is unfortunately a work of fiction with the exception of the references to myself.
Please allow me to introduce myself, I am Ken a 42 year old straight man. I am told that I am fairly attractive, and I consider myself to be in decent shape for my age. I do not workout and have gotten a bit soft. I still smoke and have since my time in the Marine Corps. I stand 6 foot 2 and weigh in at 225 lbs. I am still strong as an ox due to a lifetime of physical labor.
I have never been married and have no children. I have not been in a relationship nor have I dated seriously for almost 10 years due to back to back heart crushing break-ups. I know men can be bad, but women can really destroy a guy.
I have some wonderful friends which keep life enjoyable, and I have found that internet assisted self gratification also gets me through. This is where the real story begins.
I not unlike many other guys use the internet primarily for the abundance of porn to aid in masturbatory stimuli. Over time the typical porn had become boring, so being the dedicated man that I am I started to explore various fetish sites.
A few years ago I came across a site involving shemales (a term I now know is not preferred). At first I was just curious but that quickly turned into fascinated. The women were incredibly beautiful and I was instantly hooked. I find myself now desiring to be submissive to a transsexual "top".
I have joined sites as well as found many free ones to spur on my fantasies. I joined a transsexual dating site about a year ago but have had no success in meeting anyone in Connecticut. It seems that every other state has many more "tops" than here( the grass is always greener). I have recently started looking into TS escorts and have found a few sites.
After several months of searching and working up the nerve I decided it was time to just go for it. Several sites show escorts that are visiting the area, but I was weary of them. I chose to contact a girl that lives locally as I figured it would be a safer bet.
I chose an ad for a woman named Tiffany and after several starts and stops called her. It was a Thursday afternoon leading into a four day weekend. She answered the phone and I was greeted to an extremely sexy feminine voice. I told her about myself and, I learned that she was 28 years old 5 foot 9 and having seen her picture in the ad I knew she was sexy. We talked for about 5 minutes and she asked me when I would like to meet her. We settled on the next day(Friday) at 11:30 am. I told her I was looking forward to it and we hung up. I spent Thursday night grooming myself like I hadn't in years. The night seemed to last forever as I was so excited about the next days prospects. I hardly slept at all.
Friday morning mercifully arrived. I got up showered, shaved, dressed in jeans and a polo shirt, and started clock watching. I left the house to meet Tiffany at a restaurant near her home. I arrived early as is usual for me. I got a table for two and awaited her arrival. It wasn't long before the hostess showed her to the table.
I was struck speechless. She was more beautiful than any photo could capture. She was wearing high heels, a black mini skirt that showed off incredible legs, and a white blouse that was loose fitting but could not hide her ample breasts. Her blond hair was just past her shoulders and, she has the most stunning blue eyes I have ever seen. I stood as she approached smacking my knee on the underside of the table and spilling our waters(I am so graceful). I managed not to get soaked as she and the hostess laughed.
We sat after I assisted in the clean up of our table. We ordered drinks that I hoped would calm my nerves down a bit. We chatted as we waited for our lunches but despite my best efforts my nerves were taking over. We ate and after I paid the check we went outside. Once in the parking lot she told me to follow her to her condo.
It was a short 10 minute drive but, it felt like hours. I parked and followed her into her house. She turned to me in the entry way and asked if I had her "gift". I handed her a white envelope containing the suggested donation. She took it and placed it on the counter along with my keys and lead me into the living room. She sat me on the sofa and went to put on some music before joining me.
She returned and sat next to me placing a hand on my thigh that sent shockwaves through me. I was already getting hard and she noticed tracing her fingernails across my jean clad cock. Then it happened. My nerves went into overdrive and I started freaking out. I tried to talk myself down but to no avail. I was shaking like a leaf. She tried to calm me down saying its okay, don't be nervous. I was too far gone. I apologized as I stood up and said I have to leave, I cant do this. I made my way to the counter and grabbed my keys. I stopped and apologized again and told her to please keep the "gift". I was reaching for the door handle when every thing went black.
I was startled awake to the odor of smelling salts. My head was pounding and for a moment I didn't know where I was. As my senses slowly returned I realized that I was bound to a sofa chair. My legs to the front chair legs, my arms down the sides to the rear chair legs. I started to struggle against my bindings to no avail, it was then I noticed I was naked and gagged. I looked around frantically but saw no one. Looking down to check my leg bindings I saw that my cock had been secured in a chastity device.
It was then I heard her voice say, don't worry you wont be needing to use that today. I could not see her. I tried to yell at her to ask what the hell she thought she was doing, but the ball gag allowed only mumbled sounds to escape. I was yanking on my tethers and wiggling side to side desperately trying to free myself when she came up behind me, yanking my head back. I looked into those amazing eyes that had now turned menacing. She showed me the stun gun and said you need to calm down or this will calm you down.
I immediately fell silent and went still.
She released my head shoving it forward. It was then I actually feared for my life for the first time in many years. The only thoughts I could muster were to tell myself to calm down, get a grip, do as she asks, and you just might make it out of here.
She slowly walked in front of me placing the stun gun on the coffee table. I looked to her with pleading eyes that suddenly went wide as I took in the sight before me. She seemed to tower over me now. I couldn't stop myself from looking at her. She was wearing black high heels, black stockings hitched to a garter belt, black leather boy shorts, and a black lace corset.
She turned back to the table to grab a cigarette and I was staring at the single most beautiful ass I have ever seen. As she turned back to me lighting her cigarette she said, you like what you see? I could only nod as she leaned forward exposing her incredible cleavage to my eyes. I must have made a face from the feeling I was having from my cock trying to get hard locked in its cage, because she giggled and reached down grabbing and squeezing my balls saying, awe poor baby, seems like your little man is trying to show his approval of me.
She released her grip on my testicles with an evil grin. She turned back to the table and picked up the white gift envelope I had given her earlier. She opened it, counted the bills, and said to me, you have paid for 3 hours. She went on saying, we lost one over lunch, another when you, umm blacked out, so what am I going to do with you for the last hour? Then her phone rang.
Picking up her cell and saying hello, she stood before me. Yes this is Tiffany she said to the caller. I thought about trying to scream, and she must have sensed it as she just looked to the stun gun then back to me. I sat in silence as she went back to her conversation. She told the caller, no honey I am sorry, I am not taking anymore appointments today, or for the rest of the long weekend. I have plans, but please feel free to call me Tuesday. Hanging up the phone, she looked at me smiling and saying, I guess you are all mine for the next four days. Whatever shall we do?