Shemale First Time

byCanine51©

First time Sex with a shemale.

Intro.

I have read several stories of first time sex with Transexuals and none relate to my experience. So for those who are truly curious about how to go about it and what it is like this is my tale.

I have always been a straight guy as far as I know. Married for over 15 years and never strayed once. Early in my life I was close to touching another boys cock but parental intervention stopped this before it got started. Does that mean I'm a frustrated homosexual? I don't think so. However sometime during my life i began to wonder what it would be like to suck another guys cock and be penetrated. Guys don't turn me on, I tried fantasizing but the reality of hairy blokes just left me cold.

About 2 years ago I began looking at Transexual porn and realised that I was attracted to the male genitals when surrounded by the female form.

It was at that point that a seed of an idea formed.

Story.

There I was in a backlane somewhere in the suburban areas of a UK city looking down a path to the entrance to some slightly salubrious looking flats which fronted a tired row of commercial property.

Prior to this I had been considering how I might do this thing. How to keep it secret and what might go wrong.After extensive research i found a Transexual Escort that was far enough away that it was unlikely I would be seen, but close enough that any meeting could be fitted into a day.

I was very tense as I rang the number from my mobile, seated in my car prior to an early business meeting. My throat was dry and I was shaking. The phone was answered and the person on the other end sounded mature and very female. She gave me direction and we set a time for later that day. I even took cash out of my credit account so that it was all very untraceable.

The whole business meeting I felt like a nervous wreck, my mind rnning over the reality of what I was about to do and my concentration on the meeting at an all time low. Wow, sucking a cock and getting penetrated in my virgin arsehole for the first time. i really wonderd if I would go through with it, or simply bolt at the last minute.

I had struggled to find the address and when I did eventually park up, the row of shops looked very forbidding, seedy and slightly run down. it felt as if the world was watching me as I climbed out of the car and dispensed of all my identification and my phone ( I had a dread that somehow I would be contacted and black mailed such was my paranoia).

The path to the flats lead to a slightly open door and I was told to enter and go straight through to the door directly ahead of the enterance.

I knocked and was ushered in to a small apartment. My date was taller than me. She was slim, white with long blond hair and was wearing black knickers and a bra. I didn't dare stare at her so just asked if I could use the toilet first.

When I emerged she showed me into a small bedroom which was lit with a red light. She asked for the money first and I fumbled the cash from my pocket.

She told me to take my clothes off. I had expected this because it's a way to ensure that prostitutes are not going to get incriminated and prosecuted by the law.

I undressed without any formality and piled my clothes up on the chair next to the single bed. The room was very warm and felt quite secluded and intimate.

She asked me to get on the bed and lie face down while she gave me a massage to help me relax. never having had a massage this was an experience in itself. I felt her weight on my buttocks and the warmth of her thighs around my waist. There was a squeezing sound from a bottle and massage oil was dribbled onto my back. The oil was very heady and having her hands work over my body was incredibly sensual, really hot as her hands glided over my buttocks and moved close to my groin. I was happy just lying there and relaxing as she talked to me about what I wanted to do with her. I was half expecting her to say that she wouldn't let me suck her cock, or penetrate me, but she said it would be fine.

She lifted off me slightly and asked me to turn over and lie on my back. She sat back down and began to massage my chest. After a short while she stopped and asked me to put my hands on her. She laughed and said that it was what i had paid for after all.

I didn't waste any time and tugged her panties down and exposed her limp cock. She was shaved and that big purple cock head protruded from the wrinkly foreskin. This was the first time I had been so close to another cock and I filled my mouth full of that delicious fruit. My hand delved inside her skimpy black panties and cupped her soft, warm balls. God they were big, mine felt more like chestnuts and hers were big ripe plums.

Her cock began to grow in my mouth as I sucked and liked the head and shaft. She asked me to be careful with my teeth and I tried my best as her cock swelled to fill my mouth forcing my jaws wide.

At this point she got off me and took that amazing rod from my lips. She was fully erect and from my position her cock looked about nine inches long and I was wondering how the hell I was going to get that monster inside me.

She took off her panties and bra and lay down beside me. I couldn't keep my eyes off that giant between her legs. The head looked like it was about to explode, the skin was tight and smooth and the shaft slightly curved, milky white and veined. I started again. Engulfing that swollen head with my lips and letting my tongue run along the piss slit and along the back of the head. I wanted to take it all in, to savour every moment. I was suprised at just how slippery a cock head actually is, not at all like plain skin it is more of a membrane and it has a taste. In this case I knew it was the taste of a male, not unpleasant and quite arousing because I felt very submissive without being threatened in any way.

I licked her massive balls, I just couldn't get over the size of them and felt a kid of privilige that I was being allowed to hold another persons tender, vunerable parts in my hand. My tongue picked up the slight coarsness of her closely shaved scrotum, another turn on, and suprisingly I wished she had a full compliment of pubic hair for me to nuzzle into.

I really wanted her to cum in my mouth, but I worried about the possibility of picking something up (not so bad if you are single). She asked me if I wanted to be sucked by her. I nodded and she twisted her body until she could swallow me.

I wasn't really up for having my own cock sucked. it was nice in a way but really didn't turn me on. I kept semi hard as she continued to bob her head up and down my cock and I was aware that my cock looked a lot smaller than hers. Maybe it was the angle and the fact that I was only semi erect but I'm sure her cock was seven inches long compared to my six.

She pulled her mouth from my cock and asked if I had enjoyed it and politely I said yes. next she asked if I wanted to be fucked. I couldn't wait, the thought of a real cock filling me had been a long time fantasy.

She got me to kneel on the bed and push my bottom in the air, She pushed my back down flat like a frog and spead my legs further apart. When she had me in the right position she applied lube to exposed anus and I felt her finger penetrate me.

Wow, just that finger was heaven, it burned slightly as she worked the lube into the muscular ring of my anus and I contacted around her probing finger trying to grip the slippery intruder.

After a few seconds she pulled her finger out and wiped the remaining lube onto my scrotum. Bloody hell it was so damned hot being so exposed and awaiting the first touch of that huge cock that had so recently been filling my mouth to capacity. My mind was reeling from the sexiness of it all and the heady smell of massage oil that permeated the air.

I could hear her open up a condom and I made some daft quip about not getting me pregnant and she laughed which relieved some of the tension. She asked me to relax and to push back onto her when I was ready and to take it easy.

I felt the first touch of her cock as she positioned herself against my virgin hole. This was like jumping out of an aeroplane for the first time, totally immersive and slightly scary at the same time. I pushed back against her and felt my anus begin to stretch. Phew she was big, as I pushed back harder it felt like a log was being forced into me, but it was so sexy and dirty at the same time. I was determined to have her inside me even if it split me in two so I kept on pushing until my anus burned with the intensity of it and finally I knew the head was inside me. With one more push that huge, fat cock was lodged deep inside my bowels.

She began to work her cock backwards and forwards inside me. As she continued the strokes I felt the pain vanish and it was replaced with a simple longing to be fucked harder. With every stroke I could feel the prickle of her shaven balls against the soft flesh of my buttocks as she embedded herself to the hilt. I reached my hand between my legs and felt those twin spheres each time they came into reach.

"Oh" she said, "you really like being fucked by my big cock.". Wow I felt like a slut, being banged by a young, six foot blonde bombshell with the looks of a female and the strength of a male. She fucked me senseless, turned me on my back and fucked me like a girl with my legs in the air. Fucked me on my side while rubbing my cock. Fucked me all ways until my head was spinning with the effort and the physicalness of it.

Finally we returned back to the position where we started and she slid her cock into me deep and slow while using her hand to wank me off. My prostate was pounding from the pressure and I could feel I was ready to ejaculate. After a few more strokes I came into the palm of her hand. A big puddle of semen that she wiped onto the bed covers.

"quite intense isn't it" she said. "A stronger orgasm than plain sex". Phew she was definitely right about that, it felt like my balls had been drained completely and I could hardly stand.

She asked if I would visit again. I said probably not but she smiled wickedly and told me I would be back.

Up to now I haven't been back, but I do think about it from time to time and wonder what it would be like to have that big cock shoot semen onto my tongue.

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