Better Than Video!

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Fantasizes about encounter; finds her on the internet.
2.8k words
4.51
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I held my cell in my hand just staring at the screen of my Mac. I had been searching for the past thirty minutes, reading the advertisements and trying to work up my nerve to call. Of course, I had been working on my nerve for the past month! I had decided she was the one I would call and now I only had to dial those 10 keys to speak to her.

I had been with the same girl for the past three years but things had been unraveling for about six months before we finally called it quits. It was a number of things that changed about both of us but it was also my increasing fascination with the beautiful transsexuals I had discovered in a hotel magazine rack. I saw an article about them in a Penthouse magazine and then I began to learn more on the internet. Soon I found myself renting a video while I was on a business trip. This led to buying magazines and videos, always featuring sexy transsexuals.

After a year of hiding the magazines and videos, I finally told my girlfriend about my fascination. At first she was understanding and even went so far as to use a strap-on with me a few times. But eventually she couldn't understand my growing interest and felt she was competing with my fantasy world. And she was probably right that she couldn't compete.

As I thought about it, the amazing part to me was that I have never even had a bi-experience or wanted one. I was never attracted so why could I not shake this unquenchable desire to be with a transsexual in a sexual way? I had been wrestling with this question for months and decided their was only one way for me to answer the question. I had to be with the object of my desire and find out if reality was as good as my fantasy.

I found a website that had local versions catering to escorts. The site was well-done and provided pictures that claimed to be authenticated. The girl I selected was "Cindy in San Diego". The site displayed three very sexy pictures of her. She looked very cute with a great smile and a petite build. Her ad stated, "I'm 23 years old, 5'7", 127 lbs., 34C-26-34, have long blond hair and brown eyes. I'm also 8" cut and functional."

Examining her pictures more closely, I noted her curly, shoulder-length blonde hair and a look that would immediately attract me to her if I saw her at the mall. My hands shook as I pressed the digits on the phone. On the third ring she answered in a soft, fun voice. Immediately her demeanor put me at ease and we chatted for a few minutes. We made an appointment for later that evening at her apartment.

I hung up the phone and felt a raging erection in my shorts. I have never been this turned on by merely speaking with someone in my life. I had three hours before I needed to leave to meet her. She lived about 45 minutes away from my place in Mission Valley. I grabbed a beer and walked out onto my patio, looking down on the pool below me. I could see a couple co-eds from SDSU sunning themselves in the warm spring afternoon. As I drank from my bottle, my left hand slid inside my shorts. I began to softly caress my erection, running my fingers up and down the tightly stretched skin. I could only imagine what I would be feeling later that evening. I teased myself through my beer but not to the breaking point. I wanted to be ready for Cindy when I met her.

Ninety minutes until meeting my fantasy, I began to get ready. I slipped out of my shorts in the bathroom as I turned on the hot water. I looked at my profile in the mirror wishing I hadn't gained the ten pounds the last few months but nothing I could do about it now. I let the hot water wash over my body as I soaped myself in every nook and cranny of my body. Picking up the razor, I felt the hair in my pits and lightly ran the razor through them. Making a few passes for each underarm, I soon had my armpit hair shortly cropped. It looked like just a couple days worth of dark stubble.

I had never had much of a hairy chest, but since I began living alone I had been shaving my chest and stomach. I lathered my skin and ran the razor over the short, dark hairs leaving my skin very smooth and hairless. There have been times while watching videos that I would slip into a stuffed bra to emulate the girls on the screen. A hairy chest would never do!

Saving my pubes for last, they too were in need of a touch-up with the razor. I was once again hard from my thoughts making the skin so much easier to shave. Lathering my ass cheeks, balls and penis, I took the razor to my skin. I made sure to shave my crack and that sensitive area between anus and sac. When I was done, the only pubic hairs that remained were a small patch above my penis. These hairs I had not shaved in months. They covered an area about two inches by two and the hairs were easily four inches long when pulled taught. I had seen a similar look on a particularly sexy transsexual months ago and decided to copy her look. I loved looking at myself with these hairs fluffed up away from my skin.

After washing my hair, I stepped from the shower and dried. I shaved my face until my skin was nice and smooth. I looked at my nude body in the mirror and felt confident in my appearance. It wasn't like it was a date, but I sure felt like I needed her approval. I opted for a bright orange thong under my Levi's. I'm quite tan from the San Diego sunshine and the orange always heightens the appearance of my tan. I pulled on a light blue dress shirt and loafers. Checking my watch, it was time to leave.

#

I followed her directions and found a parking space in her complex. I checked my watch and walked to her door, knocking promptly at eight o'clock. As she opened the door to let me in, I'm sure my jaw dropped as Cindy was even more attractive than she appeared on the website. I stepped inside and she closed the door behind me. Having never been with an escort, I was nervous and excited and not really sure what to do or say. Cindy offered me something to drink and I told her I'd have whatever she was drinking. I took in the decorations of her place as she moved us to the kitchen.

She poured drinks into two glasses, "I'm having a martini. Would you like an olive?" I merely smiled and she took that as a yes. Cindy handed one to me and we clinked glasses, "to an entertaining evening". "I'm going to get a little more comfortable. Let's get that silly stuff out of the way and then I'll help you relax."

Cindy disappeared down the hall for a couple minutes and I fumbled with my wallet. I pulled out the $250 we had agreed upon over the phone and laid it on the table where she had left her martini glass. When Cindy returned, she was truly a vision for my eyes. She was now wearing a yellow lace corset that accentuated her 34C breasts, pushing them up and out by design and matching boy shorts. She wore four-inch yellow heels with sexy cuffed socks that highlighted her thin ankles and shapely calves. "Oh my ... You are Beautiful!" I exclaimed.

Cindy walked up close to me and I could smell the lovely fragrance on her skin. The heels allowed us to look one another in the eyes. She slipped her hands around my waist and pressed her lips to mine. She parted her lips as my tongue slipped inside her warm mouth and our tongues rolled together as our bodies pressed tightly together. My fantasy was playing out as I stood here kissing the most sexy woman I had ever seen.

My hands wrapped around her waist but soon moved down to her ass cheeks. Slipping inside the boy shorts, my fingers moved over the thong she wore to caress her smooth skin. Cindy pressed her left thigh between mine, her pelvis rubbing against my erection through my Levi's. My right hand moved up her back and unfastened the four snaps holding her corset in place. As the last snap popped, Cindy's hand moved between our chests and held it in place against her breasts. She broke our kiss and moved back one step. With a smile, she let it fall to the floor between us. My eyes looked down to gaze at her beautifully tanned breasts.

I bent my neck and lowered my lips to her left nipple. Taking it in my mouth and rolling it with my tongue, Cindy pulled my head tightly against her. I moved to her right nipple, nibbling and suckling it. I was getting so worked up from her body and what I knew awaited. After a couple moments, Cindy pushed my head away from her breasts. She unbuttoned the top three buttons of my shirt and pulled it over my head. I could see her eyes open a bit wider when she noticed my sparse underarm hair and then she ran her fingers over my smooth chest. Smiling, "smooth skin ... I bet you get naughty when you are home alone." Her fingernails raked circles around my nipples causing goose bumps to rise on my flesh.

Cindy bent forward and I felt her moist tongue on my right nipple. Reaching down, she unbuttoned my 501's and pushed them over my hips. "Ooh ... very nice" she commented as she saw my bright orange thong and the incredible erection that it held. "You do get naughty at home ... a girl can tell these things." I could swear I saw the bulge in my thong jump when she said that.

Cindy turned away and pulled her boy shorts down slowly over her hips. Her incredibly shaped ass came fully into my view with only the thong slipping between her crack. Turning to face me now, I could see a hint of a bulge in her thong. She let me take in her body before saying, "Follow me sexy. I know what you want to see."

I followed her down the short hallway, the heels she still wore causing her ass to sway sexily. Stopping just before her large bed, she turned around to face me. She slipped her fingers inside the waistband of the thong and pulled it away from her hips. Bending at the hips, and herself from my view, she slid the thong down her thighs to the floor. Standing up straight now, my eyes were fixed to her pelvis. Cindy was a vision of sexiness. I took her whole body in my gaze. Blonde hair and great smile ... incredible breasts topped with pert nipples ... and this beautiful cock hanging between her thighs. She displayed just a hint of blonde pubes. Cindy took my hand and brought it to her cock. Tentatively I took it in my hand and began to slide my fingers around it.

I felt it grow in my hand as I continued to slide my fingers up and down it's length. Cindy leaned into me and we kissed once again. This time her tongue slipped past my lips as she pressed herself into me. I kissed her back but my mind was focused on the growing cock attached to this beautiful woman that I held in my hand. Without my realizing, she began to slide my thong over my erection exposing me to her touch. Her fingers began to work my length. Sliding up and down my smooth cock. Her other hand began to squeeze my smooth balls as she sat back on the edge of the bed.

"Interesting pubes ... I don't know if I've ever seen any this long." I was at my full seven inches and straining for more. Cindy looked up at me then leaned forward and wrapped her lips around my crown. I could hear myself moan as her lips opened wider as she slid down my shaft. Her left hand squeezed my balls and her mouth covered the entire length of my cock. She began to slide up and down on my length, sucking on me as she did. When she would pull back, alternately I could feel her tongue trace circles around the crown or dive into my pee hole. Subconsciously my fingers were pinching my nipples as Cindy drove me crazy with her mouth.

After a couple minutes, I knew I could hold out no longer no matter how hard I tried. I could feel myself getting ready to blow and Cindy took my entire length into her mouth pressing her nose to my body. I groaned out loud as my cum exploded down her throat. She took my stream and sucked on my cock to pull another load from body. My breathing was audible to both of us as she pulled her lips from my still hard cock.

Cindy pushed herself onto the bed, propping her head on her left elbow. Her body stretched down the bed, her right leg bent in the air at the knee. I watched, seemingly in a daze, as her right hand tweaked her nipple before gliding down to her cock. She playfully stroked it before my eyes. It was at it's full eight inches as she smiled at me. "The site says I'm fully functional. I think you need to see for yourself." I hesitated, my feet seemingly glued to the floor. "You really haven't been with a girl like me until you've been with a girl like me! I need you to take care of this 'big' problem you created!"

I took a step and then a second step and then I was on the bed. I crawled between her legs as she was now on her back, her head propped up by a couple fluffy pillows. Tentatively I lowered my lips to her cock. My tongue slipped past my lips and circled her crown. Cindy made soft sounds of encouragement as my hands rubbed her inner thighs. My lips opened wider and my mouth began to slide around her cock. I tried to remember everything that I've ever enjoyed from oral so I could do the same for Cindy. I quickly got into a rhythm, my mouth beginning to slide down and up the length of her hard cock.

The index finger of my left hand rubbed the skin between her cock and asshole. Feeling Cindy's movements, I got braver and pressed the tip of my finger to her asshole. I could feel her grinding on my finger. My mouth was sucking on her cock as I took the top six inches. I tried to take all of her but my lack of experience left me short. My finger popped inside her asshole to the first knuckle. I tried moving it in and out of her asshole as it seemed to stimulate her. "That's it ... that's it ..."

"I'm gonna cum ... I'm so close ..." The moment of truth for me. Cindy had warned me of her pending orgasm and had to decide what to do next. The thought of pulling free quickly crossed my mind but instead I plunged my mouth down onto her cock, taking in as much of her as I could. I felt her cum splashing in my mouth and against my throat. I gagged slightly but kept her cock buried between my lips. She thrust of her hips upward again and I felt her blast against my throat again.

Before I knew what was next, Cindy pulled me up over her body. She pressed her lips to mine and I could feel her tongue pulling her just ejaculated cum from my mouth. We played with the texture of the warm liquid between our tongues. I couldn't believe it, but this never before sensation caused my cock to shoot another load of cum. It smeared between our bodies as Cindy swallowed her own cum.

We lay there for a moment, both of us catching our breath. "I do hope I was everything you fantasized but our time is up, Sugar." I rolled off of her and walked to the bathroom to clean myself up from my last ejaculation. I picked up my thong and slipped them over my hips. Bending down, I kissed her one last time.

"You were amazing. Thank you. I can let myself out." I dressed myself as I walked to the door. Closing it behind me, I could already feel my cock growing hard as I reflected on the last sixty minutes. Videos are good, but nothing like the real thing ...

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9 Comments
ShortyMacShortyMac9 months ago

That was such a hot story. I remember my first time with a trans girl. While it wasn’t as good as the fantasy of Cindy it was still hot. Your story deserves at least 15 stars………🤤

⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️

AnonymousAnonymousover 6 years ago
Great story

That's how it all starts. Nervous apprehension leads to relaxation and your first mouthful of cum. Next thing you know you have big cocks spitting in both your mouth and ass simultaneously, hoping it will never end. Nothing better than taking cock in both ends at the same time. Everyone loves a she-male or two.

greenhawk46greenhawk46over 10 years ago
totally hot

tgirls are amazingly hot, so much fun to explore and have sex with thanks

BimboBambiBimboBambiover 12 years ago
apprehensive

Like the author this is something that I've wanted but been afraid of for years. The lust and desire than a TS inspires in me is something that is part of me. The fear of giving into my desire and actually succumbing to a TS much less a paid escort fills me with both lust and foreboding. What will I be like after? Will my lust from sucking and being fucked by a TS's cock change me and if so how? Will the obsession of taking a fantasy and making it a reality make my next obsession just cock? Cock in any way shape or form. Cock attached to men rather than just the TS fantasy I currently have. Will I begin glancing at men's crotches the way I currently notice woman's chests?

Very enjoyable story and both surprised and , a little, disappointed that our protagonist did not complete submit and receive anal from Cindy.

CACTUS462CACTUS462over 12 years ago
mmmmmm

WOW i dont think i can get any harder reading ur stories thx Dana xxx

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