4 comments/ 329698 views/ 27 favorites Shemale First Time By: Canine51 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. Shemale First Time Ch. 01 I had just gotten home from the store when it hit me. I looked in the mirror and said to myself, girl you need to get out of the place for a while. I had 2 weeks off from work and decided I would take a trip to a bigger city. I got on the Internet and started doing some research on the gay and lesbian population for different cities. After digging deeper I decided I would take my vacation in Orlando, Florida. I called and made hotel reservations and loaded my stuff into my car. Finally, I thought, I am getting away from this small lifeless city. I figured it would be best to drive straight through instead of stopping. By the time I got to my hotel I was ready to take a nap. I slept the rest of the night and woke up early the next morning. I was ready to explore Orlando. I spotted a bar and decided to stop and check out the scene. I immediately noticed the bartender. She was tall and slim, long, curly brown hair, and dark brown eyes. She was a total knock out. I walked over to the bar and ordered a coke. She looked at me and said "Honey, we don't serve coke in this bar." I laughed and said " Ok, I'll have a Budweiser." She handed me my beer and I laid the money on the bar. As I was pulling my hand away, she laid her hand on top of mine and winked at me. I had a few more beers and was feeling pretty good when I felt someone lay their hand on my shoulder. I turned around to see who it was and it was the same bartender. She leaned down and asked me if I wanted to dance. I said " Sure, I'll dance with you." As we danced the songs slowed down and before I knew what was happening we were holding each other tight. She bent down and kissed me softly on the lips and started running her hands over my ass. I broke the kiss and stepped back so I could admire her beauty. Soon the song ended and we walked back over to the bar and had a seat. She sat beside me and said " By the way, my name is Adriana." I smiled and said " It's about time you told me your name, I'm Tina." Adriana put her hand on my knee and told me to turn around on the barstool and face her. I did and I felt her hand slide under my skirt. Her hand slid up my thigh and her finger ran across my clit. I jumped. I stopped her and told her we should go back to my hotel. She said she should drive since I had a good bit to drink. I told her where I was staying. On the way there she reach over and rubbed my nipples through my blouse. The sensations of her rubbing my nipples made my pussy tingle. I could feel my panties getting wet and had to open my legs a bit. She sensed my arousal and said " Let's wait until we get to the hotel or I am going to have to stop this car and take you right here." I looked at her and said " Well you may have to just take me right here baby." And I slid my hand across her thigh. She stopped me and said " Let's wait, I have something to tell you before we do anything." I worried all of the way back to the hotel about what she could have to tell me. I opened the door to my room and walked in, Adriana followed behind me. As soon as she got in the door she pinned me against the wall and I felt something push against my stomach. I looked down and saw the biggest cock ever. I pushed her away and said "Oh My God, you're a man." She looked me straight in the eye and said "I'm far from a man baby," and she took her shirt and bra off. Her tits were real and I told her to explain. She said " Fuck now, explain later." I didn't object and she started undressing me. When I was completely naked, she kissed down my neck and chest and took my nipple into her mouth. I was in heaven. I started begging for more. She picked me up, carried me to the bed and said " You want more baby, you're going to get more!" She licked down my stomach and I felt her tongue slide over my clit. I moaned and she took my clit into her mouth and started sucking it. She pushed her tongue into my virgin pussy and I went wild. I started pushing my pussy onto her tongue. My juice was running down her chin and down my ass. She couldn't lick it up fast enough. When she was satisfied with how wet I was, she took her jeans off and took something from the pocket. She walked over to me and laid her massive cock on the bed beside me and said " Would you like the pleasure of getting this monster nice and hard so I can shove it in that tight pussy?" I had never sucked a cock before but I gladly accepted and took her head into my mouth. I slowly pushed as much of it as I could into my mouth and began slowly sucking her cock. I knew I couldn't get all of that monster into my mouth so I licked down her shaft to her balls. She moaned and said " If you keep sucking me like that, I'm not even going to be able to get the head of this big cock inside of you before I explode." She pulled her cock from my mouth and I saw she had a condom in her hand. I looked up at her and said " I have never done this before." She smiled and said " Ohhh a virgin huh, yummy, looks like I got lucky tonight." She rolled the condom down her cock and laid down on the bed beside me. She checked to make sure I was still wet and pushed 2 fingers deep inside me. It hurt and I screamed. She kissed me and told me it would only hurt for a minute. She rolled over on top of me and pushed my legs up to my sides, giving her full access to my pussy. She took the head of her cock into her hand and rubbed it up and down my clit. Then I felt her slide the head inside me. I felt like I was being ripped in half, she was atleast 3 inches thick and 10 inches long. She grabbed my legs and pushed them up a little further and took my hand in hers and said " Are you ready?" All I could do was nod my head. I felt her push her cock in hard. That hurt like hell. I screamed and started crying. She let go of my leg and reach up to wipe the tears from my eyes and asked me if I was ok. I nodded my head. The pain finally subsided and she slowly started pumping in and out of me. I loved the feeling of her big cock stretching me to the maximum. I moaned and she started thrusting faster. I couldn't handle anymore, I had my first orgasm. She tightened her grip on my legs and pumped her cock into me harder and faster. She screamed and said " Ohhhhhh God this is so fucking good baby, mmmmm you are sooo tight, I am going to cum in your hot pussy," and with that she came, and so did I for my second time. She slowly withdrew her cock from me and laid on the bed beside me and kissed me. I rolled over and turned the light out. We fell asleep cuddling. The next morning I woke up and she was gone. I wondered if I'd ever see her again?