My Visit To A Tranny Prostitute. TRUE STORY free porn video

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I had been 'talking' to Tina; as TV slut, for a few months on the Internet, and really got to know her quite well.
I am a married guy in my late 30's and always considered myself as being straight.
There was just something dynamic about Tina that always brought me back to chat to her.
I had joined her website and therefore enjoyed regular free web cam sessions with her, and each time I felt I got to know her better and better.
There are nicer looking transvestites about than Tina, and more convincing ones too - but there are very few who are as sexy.
When you look at Tina's pictures and videos, you can tell that she is a man dressed up, but my God! How she pulls it off is amazing!
Anyway, I digress, because I am here to tell you about my first actual meet with Tina, as I promised I would do such a report for her.
We arranged to meet at her place at 2pm on a Wednesday.
She gave me directions to a community centre in Gosport, and told me to park my car there and then telephone her.
I arrived early and called as instructed.
Tina's voice is like her persona! - you can tell its a man on the phone, but she talks extremely feminine, which in itself is a turn on!
I was shaking with excitement as I walked the 500 metres or so to her house.
As I walked down the path the front door opened in front of me as I was welcomed by the girl I had dreamed of meeting for so long.
Tina is very tall and this is the first thing (obviously) that you notice. Second thing I noticed was her fantastic cleavage and thirdly, her amazingly slender girls legs.
She had said that she would be dressed feminine but nothing too racy to start with. I would say she looked really sexy in her golden shiny satin blouse, black pencil skirt, black nylons and her patent shoes. Her make up was ultra sexy, with smokey blue and black eye shadow with lots of blusher and red glossy lips.
She sat opposite me and crossed her legs, which showed me a flash if stocking top.
She offered me coffee, which I declined (probably through nerves) but I said it was ok for her to have one if she wanted. She walked through to the kitchen and kept chatting as she made her coffee.
On returning to the front room she asked if it was ok if she smoked. I told her I had enjoyed watching her smoking on our cam sessions and I was looking forward to it very much!
She withdrew a menthol cigarette and lit it whilst looking at me in a very sultry way! Her bright red lips enveloping the white filter was a sight to behold. When she withdrew the cigarette from her mouth she held it in the last few centimetres of her rigid fingers - it was so feminine and slutty!
She asked me what outfit would I prefer her to wear. I laughed at this as honestly she looked so sexy there just sat smoking, in her very sexy secretary outfit, it was just amazing to think that very soon she would be in my arms.
As she sipped at her coffee, she asked me if I was sure I didn't want any, and to be honest I was now so much more relaxed I decided to say yes.
On getting up to go to the kitchen Tina said she would have a treat for me when she returned.
My God! Did I!
When she walked back in a few moments later with my coffee, she was wearing the most amazing black patent 6" high heeled court shoes.
The sound of the stilettos on her laminate floor alone was incredible, but the way these shoes emphasised her calfs was incredible.
After passing me my coffee she again sat opposite me and crossed her legs. This time she pulled her skirt down covering her stocking tops, but she knew I was watching and without looking down she knew she had given me an eye full of her stocking tops and suspender straps.
Over the next few minutes we discussed a lot. I brought up the subject of Tina's incredible cleavage, and she went on to tell me about her puberty age, when she knew things weren't normal. She went on to explain her late teens and early twenties, and although compelling, it isn't really necessary, or indeed my place, for me to explain it all here for you now. What I will say is Tina is very sociable and after a few minutes I was very at ease and not in the slightest bit nervous. She is extremely good with first timers, well, she certainly was with me.
After a while, it must of been ten or fifteen minutes Tina took out another cigarette and lit it and asked me if I had any deadlines for the day. It was only afterwards (after our physical meet) that she told me she was urging me to get the business side done!
I told her I had booked the afternoon off work, and so time was not an issue, but I had only booked for an hour of her time. She reassured me that she didn't clock watch, and that the hour I was paying for only started after she had been paid. She also at this point made it clear that although she loved the chat and enjoyed very much the chemistry building between us, that at some point she wanted me to join her, next to her, on her sofa.
I asked if it was ok if I joined her now, and she smiled and said 'of course".
As I got to my feet I pulled out my wallet and gave her my contribution before sitting down next to her.
She thanked my for her payment and placed the money in her black PVC purse, and placed this in her hand bag.
She then turned to me and leaned forward and gently kissed me on the lips.
This shocked me, because I had heard that e****ts do not kiss. Well this one does!
Slowly, our mouths opened and the kissing became very wet very quickly! Our tongues were lapping at each others as we French kissed for what seemed ages. (But in all honesty was probably a minute or two!)
Her left hand was now rubbing my (extremely hard) crotch area, and she took hold of my wrist and placed my hand on her boobs as the kissing continued.
Please let me tell you - Tina's boobs are big! She whispered in my ear telling me she loved having her boobs squeezed as we kissed and I can promise you I wasn't complaining!
Her hands moved to my chest and she started to undo my shirt buttons as the kissing continued. Her hand slipped into my shirt and smoothed my slightly hairy chest as I was in turn massaging her boobs in her lovely black satin bra.
The kissing stopped and she almost melted onto the floor - and was now between my legs on her knees rubbing my cock through my trousers.
"I can't wait to taste you" she said sexily as she began opening my trousers.
I helped her unbutton them as they are tight and I wanted to get my cock out so much!
As she released me from my boxers she pulled my trousers down a little before taking hold of my honestly now rock hard cock.
She looked me directly in the eye as her tongue started to lap at my bell end. In a circular motion she licked round and round the purple head, making it very wet. Then she enveloped the whole of my cock end in her red glossy lips. Looking down it was just tremendous to see a girl who really enjoyed what she did for a living.
I have heard so many horror stories about some working girls who just do stuff as they have to do to make a living, but with Tina, you know she is enjoying it. Every moment!
Her mouth was now sliding up and down my rock hard shaft. Her lipstick was smeared all over it, providing a lovely red sheen right down to the girth.
As she took me deep into her throat she let go with her hands and just
worked on me in a head bobbing style.
She closed her eyes as she gagged on me.
I held her head down on my cock and thrust myself into her open wanting mouth. This made her gag a little, and after two or three simultaneous gags she looked me in the eye and said "I like that".
This was heaven, as I have tried this kind of stuff so many times with my wife, and she will have none of it, and here I was with a girl telling me she likes to have her throat fucked! Unreal.
This went on for a few minutes: Me forcing her head down on my cock to the girth, and not releasing her until I was ready. She had tears streaming down her face, and her mascara was starting to run.
"Don't make me look silly!" She said as she bowed forward for more cock. Silly? She looked beautiful.
She asked me to take off my clothes, and this I did. At the same time she stripped out of her blouse and skirt, but remained in her black basque, stockings and hi heels. On closer inspection it appeared that her basque was in fact a waist clincher and black bra. All I can say is she looked absolutely amazing.
Once I was naked she beckoned me to get on the settee on all fours, with my bum pointing into the room.
She came up to my face and kissed me wet on the lips once, and asked if it was ok if she ran the camera. I told her it was fine as long as she didn't show my face.
"Close your eyes, please" she said in a quiet voice.
I heard her setting up the camera, it really didn't take long. The next thing I felt was her hot breath on my arse.
She held my buttocks apart, almost gaping me, and then I felt her delicious wet tongue circle the outer edges of my hole.
I have never ever had anyone go near near my arse. Not that I didn't want that, just that the wife would not do it, not under any circumstances. Anything slightly taboo was off limits in my wife's eyes and that is why I was here with Tina.
She held my hole open and I felt her we tongue enter me. I closed my eyes and just enjoyed the attention!
In between licks she told me how she loved to lick clients arses. "It shows how low I will go" she smiled.
She now asked me to turn around and sit low on the settee. As I moved into position, she did not move at all, deciding to remain on the floor.
I sat back and she was on the floor in between my legs. She lifted my legs up, and holding onto the backs of my thighs, she once again exposed my arse. Her mouth went to work straight away. This time it was long, full licks of my arsehole that she took, and this time I could see her.
Looking down at her at work was amazing. Her heavily made up face: Too much eye shadow and blusher, and again, too much red lipstick and gloss was such a lovely sight.
After a few minutes she started to insert her tongue in me again. She asked if I liked things in my arse, and I said I wasn't sure, but her tongue in there was nice.
"You taste lovely" she said "some guys taste of soap, but you have a lovely musky taste to your arse". I wasn't quite sure what she meant by that, as I had showered before I left, but perhaps there was still a lingering 'musk' as she put it, from my earlier toilet visit.
In any case, Tina certainly was not put off by it, in fact I think she loved the 'non soapy' taste and smell.
I watched as she put her finger in her mouth, and wetted it up. She looked at me as she sucked on her finger like some kind of small cock.
Her head then was bobbing once again on my cock. At the same time I felt her finger touching my arse bud.
"You like that, honey?" She said as she smiled at me, looking past my rock hard, lipstick smeared cock, which was rubbing her face.
The fact is, I wasn't liking it, I was loving it.
She expertly inserted just the tip of her finger inside me, and simultaneously started sucking my cock once more. My God! Can this girl multi task! In complete rhythm, she was gently finger fucking my arse and head bobbing on my cock.
My arse was so wet from all the earlier oral attention she had given it, and I think that it is this that helped me take her fingering so easily. It didn't really matter, what did matter was the fact I adored it, and was so loving my time with this superb, mature transvestite slut.
She lay me back on the settee, and I was now lay full length with my feet up. She wanked me slowly as she once again started to French kiss me. She was knelt down on the floor looking over me as we kissed. My hand slid into her blouse and I explored her fantastic tits.
They look and feel so full and round. She told me she loved it when I squeezed her tits as we kissed.
After some heavy petting and lots of groping she sat down and slowly removed her blouse and her bra. Wow! Her tits looked amazing! I couldn't take my eyes off them.
She leant over and started rummaging into her hand bag, and I watched as she lit a cigarette and then returned to me. She leant over me and cupped my head and literally started to breast feed me with her huge tits. Alternately, they were each offered to my hungry lips. I closed my eyes and concentrated on sucking and licking her hard nipples. She just carried on sexy smoking as I did this, and my God! Was it sexy!
A quick note here on Tina and her smoking. I know whenever she is on cam she loves to smoke and I personally think that it is extremely sexy to see her smoking, and to witness it during a meeting is fabulous, but I know it isn't everybody's cup of tea. She does say that it is not obligatory for her to smoke, but I really recommend it to those of you that do in fact enjoy seeing a tart smoke. Even the way she holds the cigarette, and all her feminine mannerisms is something so erotic.
After she had finished the cigarette and I had had my fill of her gorgeous tits, she said she needed some anal attention.
Swapping onto the smaller sofa opposite, she got herself on all fours, and invited me to 'watch the show'.
Soon she had a pink dildo in her arse. It was quite thin and Tina assured me that she uses this one purely to loosen up. It was fantastic to see her use a toy on her own arse. It wasn't very long at all before she was swapping the toy for another one, this time a bigger and fatter one, in a flesh colour.
What amazed me about her with this one was the fact that she did not give a hoot about the brown slime that was smearing the toy as she fucked herself with it. Slowly she withdrew and offered it up to her open red glossy lips "shall I?" She said as she smiled at me. "You know I will.... But only if you want me to?....... It is your show honey?"
I knew she would. I'm sure she would do anything I asked of her, but this was a bit too extreme for me, and I declined her offer on this occasion. I'm sure though that some people would use Tina's services for just exactly that...... Seeing how far or how low they could make her go. I'm not too sure about her limits of depravity, but I know she used to advertise herself as the 'girl who doesn't say no'.
My cock was now absolutely solid.
She got back on the small sofa facing away from me once more and offered her arse to me, opening her honey pot with one hand. "Come and fuck me honey" she said, "use me like the slag I am".
I hate that word, but Tina loves to use it in dialogue a lot. She once told me in one of our many prolonged chats that she felt that she was much more than just a slut and slag was a perfect description of her. In a lot of ways I'd say Tina is a wonderful and nice girl. But as soon as the sex starts.... yes! Slag is ideal!
She held her buttocks open for me as I put on my rubber. I watched as her bright red fingernails held open her little opening as I manoeuvred in position behind her. As I pushed my hard cock into her little hole she sighed as the hardness filled her up. "I love anal sex!" She exclaimed.
That is a good job, because I had paid my money for anal sex and I wanted a lot of it before leaving. Lucky for me I was not going to be let down by Tina.
I held her hips from behind as I bludgeoned her with my rock hard cock. She was talking dirty all the time, saying things like "just use me" and "use me for your sex pleasure". Tina is very forward about making sure the client gets what he wants, and not to hold back. I recall one on line conversation we had and it was based around her making sure that every client left with no thoughts of 'I wish I had tried this or that' or 'I wish I had got her to do that'.
After a few minutes Tina beckoned me to stop fucking her. I slowly withdrew my rubbered cock, and I have to say it was quite badly soiled in her smelly brown sex lube. As I stated earlier, I am normally put off by this, but with Tina everything is on the menu.
I stood back as she faced me, and started to rub and play with her heavy tits. She dragged the camera tripod across the floor and had the lens pointing at her upper torso.
What a fantastic show she put on as she slowly played with her gorgeous pert tits. She really explored them. Looking down at them, each in turn, and then looking up at me as if asking for some kind of approval. She sat back on the settee and flicked her hair before asking me if I liked her boobs.
Let me tell you, they are amazing! They are round, firm and very heavy. She advertises herself as a B/C cup. Please let me say here that she is definitely a C.
Leaning forward, she now offered her gorgeous tits to me once again. I sucked her nipples one by one and grabbed at both her tits as I did. At the same time Tina lit another cigarette and held my head as I went from one nipple to the next. She then lay back on the settee smoking, as I fondled her lovely cock. It was absolutely rock hard in her black satin thong.
She had told me that she likes to receive oral sex, but prefers it to be called a girl cock as opposed to a clitty
I have to say at this point that her cock is amazing. It looks so good encased in her black satin panties. And it is so wonderfully hard. Id say its about seven and a half inches long and is of normal thickness and girth.
As I took her in my mouth she placed her hands on my head and although not forcing me down on her hardness, she stroked my hair as I sucked her.
Tina really is quite intimate when she gets down to it.
She kicked off her panties and got back in position in the sofa, with her legs almost in the air.
When my hands were exploring her tits as I sucked her hardness, she held one of my hands. Its awkward to explain, other than saying it is very warming and very close. Odd, I think, for someone who has some quite vile tastes to persue a closeness and connectivity like this. Anyway, I liked the tenderness of her touch contrasting to the hard way I was forcing her cock into my mouth.
As she held my last hand, my right hand stroked her stocking tops and flicked at her basque suspender belt clips.
For some reason I find the straps such a turn on, and Tina's black satin suspenders were of the vintage type, with six deep tight straps and oversized metal clips holding her sexy black stocking tops in place.
Tina's cock was rigid hard in my mouth. It tasted so good and was very wet with my saliva.
I would not call myself bisexual but then again being with a good looking tranny is not in anyway like being with a man.
Tina had often said to me that she had been described as just a woman with a cock, and I think this is a very fitting description.
She sort of stopped me by edging up onto the sofa, and she was now back on all fours, facing away from me, with her arse pointing up in the air.
"Lick my girl arse" she said "please lick my girl arse!"
This is something I had never ever done in my life before. Her hands held her buttocks open and I could see her brown bud very clearly. With trepidation I edged my face with extended towards her.
I could not believe two things at this stage. 1. I was licking what in effect is a mans arse and 2. How much I was bloody loving it!
Tina did all the right things. She really stretched herself open for me to get in deep with my tongue and do the best I could.
There was a taste (for all you new to rimming folk!) but it wasn't a vile taste I had expected. I think Tina's early description of musky is very apt.
I licked at her hole, and she forced two fingers in there and opened up her love hole with like a scissor movement of her fingers. I managed to slide my tongue in between her two bright red coloured finger nails and please her as much as I possibly could. She was now riding on my tongue in a sexy rhythm, at which point I inserted my finger with her finger and she rode the two rigid digits as if it was one fat cock.
She removed her finger to concentrate on holding on the back of the sofa with both hands. She asked me to use two fingers on her arse and to "finger fuck my arse". It was just so intense.
Tina gets so carried away with everything sexual, and you can see her becoming more and more adventurous as the meeting envelopes.
There I was with two fingers hard up her arse as she rode them like a big cock. She was so turned on, her cock was absolutely rock solid. She moved off my fingers and asked me to put them in her mouth. I moved the glazed fingers to her face and she looked at me in the eye as she started to lick the ends of them and began teasing them with her hot wet mouth. It was just so sexy to see her looking at me intently as she did this.
Soon she was completely bobbing up and down on my fingers whilst my other hand she put onto her cock. Slowly I pulled her sexy foreskin back and forth as this oral show continued.
"I want some cock now!" she said. "Do you mind fucking my mouth?"
Did I mind? That was an understatement!
Just as I got up on my feet to force my hard cock into her mouth, she said she wanted it 'juicing' first.
"Juicing?" I asked.
"Give it some flavour" she said as she once more offered me her arse.
"You want me to give it to you bare back?" I asked her quietly.
She told me that was my choice, and that she didn't mind too much with clean men like myself.
I was unsure at first, but quickly thought I would not miss an opportunity like this, and she told me right at the very start that she wanted me to leave here with no stone unturned so to speak.
I began fucking her like a machine. I was really smashing her arse and Tina was obviously loving it by the moaning she was doing.
"I fucking love anal sex!" She exclaimed. "Use me! Hurt me!"
I leant forward and reached around her front and felt her gorgeous tits that were hanging and bouncing as I was pumping her full of my hard cock.
I began slowing down my thrusts, concentrating on deep penetration with gaps in between the pumps.
Then I started to withdraw my cock all together, and watched as her gorgeous smooth white arse hole gaped open for me in between fucks.
She asked if I'd get the camera shot of her gape which I did. Her hole was reddened at the edges and the cavity was wide and deep. It looked extremely good through the lens of the camera also.
I was now dying to shoot my load. It had all become a little too much for me! She was right when she had said earlier that she didn't want me to leave having wished I had done something. The only thing I hadn't done (what I was interested in) was some water sport action.
I love watching films of guys pissing in girls mouths, but to be quite honest, I just wanted to cum now. I was simply too excited.
I told Tina of my desire to spunk, and she looked at me with those tarty eyes, cupped her boobs and said 'where do you want it honey?'
I smiled as I replied 'in your mouth'.
She quickly applied another coat of thick red glossy lipstick to her over painted lips. She looked amazing as she took position underneath me, her mouth wide open.
It didn't take me more than ten or so wanks for the first spurt of hot fresh spunk to splash across her face. I completely missed her mouth as the jet went straight passed it and landed in a diaganol line from her cheek, across the corner of her eye and into her hair. The second jet however landed right where it was intended: into her mouth. She smiled with her mouth open, as the cum oozed out of me, filling her up to the brim.
Like a porn star she faced directly in front of the camera and opened her mouth wide, showing off her mouthful of cream.
Then she closed her lips and with one gulp, she swallowed the lot.
She then reopened her mouth to show that fact to the camera as well as me. She then started to pull the cum from her hair, and scoop it up with her fingers. As she got a full load of it she began lapping at her fingers and sucking them to savour every last drop.
I know some girls will do 'the cum thing' but I have never ever seen anyone do it with such genuine desire. You can tell Tina absolutely adores being a cum slut.
Well, that was about it really! Afterwards Tina offered me a drink and came back from the kitchen in a sexy very short black satin robe. She looked so good even after sex!
We chatted briefly over our drinks and she once again smoked sexily. She crossed her legs as she sat next to me and licked her hair!.. It was so sexy it's untrue!
I had to go and very soon she was at her doorstep kissing me, saying goodbye.
I will be honest and say that I have been back to see Tina on 4 occasions since this one I have described here. She asked me to write a few words to describe the feelings of a first timer, and this I have done.
As I say, I have visited a few times since, and I'm very pleased to say that I have ticked my 'water sports' box, and my! Tina did not let me down there. As expected, it was just amazing.
I have also had my arse fucked by her (only very briefly), but this again - is just incredible. The feeling of her soft stockinged legs and rock hard cock rubbing on me from behind was just unreal. Then the actual penetration was like nothing I have ever felt before.
So people, if you are like I was - thinking life is too short, then do it. Get on the phone now, and book your ultimate fantasy. You will not be disappointed!

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My real name’s Benny, and I’m a 32 year old very passable bi transvestite that has an insatiable craving for receiving another guy’s cum. I’m 5ft 7in tall, quite skinny (10 stone ‘ 140lbs to you Americans), and have perfected the mannerisms of a ‘real’ woman in every way, without going over the top by acting too effeminate like some ‘Nancy-boys’ tend to do. That means that when I’m fully dressed and wearing my wig and makeup, I walk,...

3 years ago
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First time with a Tranny

Stevie had always found it relatively easy to get girl friends. Not all had been good experiences. He always felt that after sex he just wasn’t satisfied. Maybe he wanted something different. Some people are perfectly fine about being gay or bisexual, but for others, it is a scary mine field. Stevie was one of those people. People had commented on him being gay for years and he always felt ashamed. He denied it, of course, but as time went by the thoughts about the whole subject haunted him. He...

Gay Male
1 year ago
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Young Tranny at Great Grandmas Funeral

“What’s going on,” inquired the 34 year-old construction and building inspector.“Nothing,” smiled the high school senior with the 22-inch dark brown wavy hair extensions and gray contacts. “What’s up with you.”“I want summa that.” he leaned forward trapping her between his heaving chest and the counter.“What?”“That sweet potato pie over there,” he winked.“Oh, okay! I’ll cut you a piece.”“You do that,” he said not moving an inch and running a forefinger down her weave.She darted her eyes away,...

3 years ago
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Threesome with a tranny and a woman

I have a friend with benefits that I have been with for a few months. Her name is Bree and she is a tranny. I figured out I was Bi a few years ago so I started looking around for guy's to have sex with. Like others, I found guys who seemed to want to get together but would not pan out for some reason or another. That's when I discovered tranny's and new I wanted to be with one. So I started to look around for one and that's when I met Bree. She was beautiful 5'3" tall, dark hair and a tight...

1 year ago
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Nate and his tranny neighbour

My first ever story. Depicting sex between a man and a transsexual.It is lengthy but personally I enjoy these best. Constructive feedback is greatly appreciated, so feel free to write to me. Enjoy ; )Nathan (Nate for short) was an average eighteen year old boy; liked girls, sports, partying, and being on his summer holidays he enjoyed the time off school. With some exceptions to the average rule, he loved his kinky dirty thoughts and porn. Frequently watching shemale porn, gorgeous busty women...

1 year ago
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My first but not last encounter with a tranny

My Wife and I have been married for about 3 years now and have since recently, been looking to have our first experience with a she male. I met a girl online name Judy and after chatting for a while and exchanging pictures we agreed to a meet and greet. Judy proved to be a very sexy transgender with feminine features. Her highlighted hair was long and she had size B cup breast with a thick firm ass and long pretty legs. She was very beautiful and had an awesome personality. We sat down and...

She Males
3 years ago
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Tranny Wife Me

I have always loved sex with trannies, even more than sex. Friendship and closeness that I would struggle to fin in a guy. My wife had no huge preference for Tgirls but she did have a ravenous appetite for sex and was curious enough to try everything. We decided to go to Manchester and their regular Saturday night Tranny evenings and from previous visits, we had a few drinks in Napoleon's Lounge. It was a popular meeting place for "girls." Trannies who liked other girls, trannies who preferred...

3 years ago
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My first tranny

I had never been with a tranny before and did not plan on being with one at all but you never know what will happen. I had a bad day, I had been in meetings all day with new clients in another city. I decided to stop for a drink or two before going back to my hotel room. I found this bar that look interesting so I went in. There were lots of beautiful women there so I thought that maybe I would get lucky and not have to be alone tonight. I went to the bar and ordered a drink and checked out the...

3 years ago
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My first time with a tranny

I always had a strong sex drive, and since I had been around 16 I had been turned on by gay porn. I must say that I am straight, well on second thought, better say that I am bisexual. And I always have and will like girls. But there is something about a cock that turns me on and I then discovered shemale porn. I think that a hot sexy shemale and a cock is the best combination there could be. I have a strange fascination with cocks and a hot sexy girly body tops it off.In August 2007 I was 24...

1 year ago
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Dream Tranny

Dreams can be strange, sexy things. Your wife may be a stunning knock-out, way the fuck out of your league, but I bet she ain’t your dream girl. No, your perfect fantasy angel has the big tits and pretty face you love so much, but she’s also got something extra: a big ol’ dick between her legs. Sorry, wifey, but tonight may be a good evening to spend with DreamTranny.DreamTranny.com is a site with history. They’ve been around since 2000, making them one of the older shemale porn operations on...

Premium Shemale Porn Sites
1 year ago
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Mature Extreme Tranny Prostitute Part 3

I heard someone unbuckling his belt and shuffling behind me. He was obviously getting into position. I felt a strong pair of hands on my buttocks opening me up before I felt a hardness inside me. His cock was quite thick and extremely hard although it wasn’t very long. He held my hips as he pumped into me. My eyes were closed tight as he pushed himself into me. He was gasping and groaning as he pumped me full of his meat. He only fucked me for a minute or so when I felt him withdraw. ‘Go on...

2 years ago
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Mature Extreme Tranny Prostitute Part 2

‘Yes, but I’m not messing about. If you would like to come then follow me now. I will explain what will happen when we get outside. ‘ The folder was quickly passed around the five of them, each of them looking at each other- silently asking – should we or shouldn’t we? Dave stood by his car knowing that at least some of them would come. Eventually, one by one they emerged and started to walk over to Daves car. I moved the sofa into the centre of the room. It was now facing directly away...

2 years ago
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Mature Extreme Tranny Prostitute Part 3

I heard someone unbuckling his belt and shuffling behind me. He was obviously getting into position. I felt a strong pair of hands on my buttocks opening me up before I felt a hardness inside me. His cock was quite thick and extremely hard although it wasn't very long. He held my hips as he pumped into me. My eyes were closed tight as he pushed himself into me. He was gasping and groaning as he pumped me full of his meat. He only fucked me for a minute or so when I felt him withdraw. "Go on...

3 years ago
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  • 8
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Mature Extreme Tranny Prostitute Part 2

"Yes, but I'm not messing about. If you would like to come then follow me now. I will explain what will happen when we get outside. " The folder was quickly passed around the five of them, each of them looking at each other- silently asking - should we or shouldn't we? Dave stood by his car knowing that at least some of them would come. Eventually, one by one they emerged and started to walk over to Daves car. I moved the sofa into the centre of the room. It was now facing directly away from...

2 years ago
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  • 18
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Stag Night Tranny Gang Bang

I really still don’t know why, to this day, i said i would go with Ross to the Stag night. It was probably one of my more stupid decisions in life!! I’d met Ross a couple of times before, mostly at the S Club in Merton. Ross was about twenty three, really good looking, and loved the whole cross dressing scene but didn’t dress himself and described himself as an ardent ‘admirer’. He’d approached me at the bar one night and we’d got talking. Although I was much much older than him it only seemed...

2 years ago
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Stag Night Tranny Gang Bang

I really still don't know why, to this day, i said i would go with Ross to the Stag night. It was probably one of my more stupid decisions in life!!I'd met Ross a couple of times before, mostly at the S Club in Merton. Ross was about twenty three, really good looking, and loved the whole cross dressing scene but didn't dress himself and described himself as an ardent 'admirer'. He'd approached me at the bar one night and we'd got talking. Although I was much much older than him it only seemed...

3 years ago
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Couple Finds Another Plus Tranny

While I was in the military, there were many opportunities to see some of the wild and crazy sites and people of the world. One time in Japan a bunch of us in a mixed group (men and women) went to a show that featured transsexuals. These were men who now dressed and acted like women. All of the men/women featured had breast implants to additionally make you believe they were real. The show was very exciting with each of the trannies on stage showing us they were as good looking without their...

2 years ago
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  • 27
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First Time with Tranny

So this is the story about how I got my first experience being a bottom, and why it was with a tranny.I was 18 and wanted to try being a bottom. For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc...) but I really wanted the real thing. I had the fantasy about sucking dick and getting fucked. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the...

4 years ago
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Im a Meat Packing Girl Tranny

I didn't go looking for a tranny, shemale, dickgirl, or whatever derogatory term a homophobic world has labeled women that happen to be packing a penis. In fact, while I had messed around a little with the man worm, back in college and with a drunken buddy a few times, I considered myself 100% a hetero male, in love with the female form and a total horn dog for a beautiful woman. I must admit, I've jerked off more than a few times to shemale porn on my computer at home, wondering what it would...

1 year ago
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My Tranny Schoolgirl Fantasy

As I sat on my couch, i was thinking, "Being alone doesn't have good perks. Maybe if I wanted to dream something naughty, it might be cool." So, I closed my eyes, and I dreamed of a very naughty tranny schoolgirl who would do what i like. All of a sudden, I heard a sexy female voice say to me, "Hey Brian, you bad boy, you big stud." I woke up, and there was this hot tranny girl who was dressed as a naughty tranny schoolgirl. She had nice lovely pigtails, a very sexy tied tight white top, in...

3 years ago
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My first time as a bottom and with a tranny

So this is the story about how i got my first experience being a bottom, and why it was with a trannyI was 18 and wanted to try being a bottom. For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc...) but I really wanted the real thing. I had the fantasy about sucking dick and getting fucked. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the...

4 years ago
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Nate and his tranny neighbour Part 3

Nate and his transsexual neighbour part three, as always hope you freaks enjoy and let me know what you think ; ) Nate woke up thinking about his last two encounters with his hot big-dicked neighbour. Having never had much experience with woman to having the hottest sex he could hope for was a dream come true. However as he slowly stroked his hard morning wood he realised he had yet to fuck Jez, her gorgeous tight ass in lycra was a vision to behold. Wanting nothing more to feel her pretty...

2 years ago
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Fun with a latina tranny

So I'm a big fan of a big tranny cock in my ass. Just throwing that out there early on here.So this past summer I decided that with my school being off I should get some tranny cock as fast as I could. I went on a site and set up a new account, hoping for the same luck I had a few months ago with a hot black tranny named Jade and her friend. I quickly found a very nice 20 something tranny names Maria who said I would do. We went through a few chat sessions, with our cams on and I convinced...

4 years ago
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Amy The Tranny Chapter 1

I met Amy at an adult theatre in town.She was dressed to nines in a mini skirt, tight halter top, and pumps leading up a pair of fishnet clad legs. I invited her into a private boothand once inside, went over her price for someadult fun. She told me I couldn't fuck her as shewas on her period but I knew something was up and asked her flat out if she was a tranny. She looked at me wearily and slowly nodded her head. I assured her I was into tranny sex and she relaxed and asked if I was into just...

4 years ago
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Tranny Delight

I had been feeling particularly horny one day and waiting for Joe to come home I got to thinking about having sex with a black woman and then watching as Joe took her and then thought even more that perhaps a black tranny might be a bit more fun. So when Joe came home I easily talked him into going down to the alternative nightclub we had visited once before and off we went. Upon entering the club I saw that it was as crowded as usual and Joe and I took up a small table and settled with our...

3 years ago
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The Perils of Pauline Tranny at the Truck Stop

Paul sat behind the wheel of his Mustang, the windscreen opaque with heavy rain. It had been raining hard for the last hour and he was hoping it would have stopped before he reached the truck stop. He looked through the windshield as the wipers lazily swept back and forth across the glass. The sodium vapour lamps bathed the parking lot in an orange hue. The blacktop was slick with rain and puddles had formed in the numerous potholes. The lot was quiet; as it usually was at 8:30pm on a Tuesday...

2 years ago
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Tranny walks around soho late at night true

After going to Trannyshack and dancing the night away i left the club at 2am. I was drunnk as guys had bought me drinks all night. A few guys had sat next to me and made me feel their cocks - all were nice and hung lads. The guys liked my long legs shaven with fishnets - black court shoes and and painted nails. I was wearing a short black skirt and low cut top. Long dangling earings and long dark hair. I was made up with smokey eyes - dark plum lipstick and lots of rouge. My lashes were thick...

2 years ago
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Revenge on a Tranny

Revenge on a Tranny My relationship with my partner Julie had been strained over the last twoof our ten years together. For a period of six months we?d stopped having sex.I thought she might leave me but I figured that if she was going to find anotherwoman then there was nothing I could do about it and besides, I had a womanor two I knew I could fall back on for affection if I ever found the need.I was a good lover, but there seemed to be something that Julie needed sexuallythat I couldn?t...

2 years ago
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Mary the PROSTITUTE WHORE her side of the story

     This is iIn response to my story named    How I got my wife to become a PROSTITUTE & A WHORE                           Today I received a nice note from   a friend.   Here is a copy of it. fantastic story you wrote, plaese give regards to mary, I hope one day she will tell her side off the story.       Well I thought that was a great idea so I asked Mary herself to let you know what she thought.       First of all before Mary gives you her side of the story I want to make a few...

2 years ago
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Mary the PROSTITUTE WHORE her side of the story

     This is iIn response to my story named    How I got my wife to become a PROSTITUTE & A WHORE                           Today I received a nice note from   a friend.   Here is a copy of it. fantastic story you wrote, plaese give regards to mary, I hope one day she will tell her side off the story.       Well I thought that was a great idea so I asked Mary herself to let you know what she thought.       First of all before Mary gives you her...

Voyeur
2 years ago
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Flat Mates Chapter 2 My first visit to a Tranny Club

FLAT MATES Chapter 2: My first visit to a Tranny Club Having told Gloria that everything was "cool" between us, she then proceeded to shock me with her next statement. "If you wouldn't be embarrassed to be seen out in public with me," Gloria continued, "why don't you come with me to the club tonight? The band you say you like so much are playing again and I am sure you would enjoy yourself." "I'm not sure," I answered. "I would really like to hear the band but I'm not confident...

1 year ago
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Truck Stop Tranny Sluts

My girlfriend and lover Candi and I were driving back to her place for some steamy tranny sex after a night of partying at a tranny/gay bar in town when we passed a truck stop on the highway. Buzzed and horny as we were, we laughed about stopping in the lot and doing so hookin’ as a means to get us some trucker cock. After a minute or two of silence, Candi said lets do it and before I could answer she was turning back for the truck stop! Candi and I are both bisexual crossdressers and we pass...

Crossdressing
2 years ago
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Mom Is A Prostitute ndash Part I

writing this story about my hot mom BHANUMATHI, usually called BHANU. In this story I tell you how she became a prostitute. BHANU mom has a fair complexion, her vital stats are 38-30-40. She is now 39 years old. She was the marketing manager in a MNC firm before she became a prostitute. She has taught me sex at a very young age of 8 and how I came through her pussy to this world.After finishing dinner at the restaurant at night 10 O’clock, mom and I were walking towards home. Mom looked very...

3 years ago
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Tranny in Toronto Chapter 2

Introduction: Read first two stories on my profile. I cant seem to find the conversation we had by e-mail. ~~~ Since I lost my virginity to a couple I met on Craigslist (read my past story) and I not only had a wonderful time, but got paid as well, I decided to post my own ad on Craigslist. It was a simple ad, a tranny in Toronto looking for fun time. He saw my ad on Craigslist and decided to message me to see whether or not we could get together or not. His name was Marc, a young black boy...

2 years ago
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My first time with a tranny

It happened on a Monday morning. After waking up with a throbbing hard-on. I called up my regular booty call. But she couldn't make it. Because her husband stayed home from work that day. So I decided to browse Craigslist, looking for someone local. After posting my ad, looking for NSA sex. I sat back and waited. Within minutes, I received over a dozen new messages. But none of them really appealed to me. Then after a few hours of receiving numerous messages, from both women and...

2 years ago
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Tranny in Toronto Chapter 2

~~~ Since I lost my virginity to a couple I met on Craigslist (read my past story) and I not only had a wonderful time, but got paid as well, I decided to post my own ad on Craigslist. It was a simple ad, a tranny in Toronto looking for fun time. He saw my ad on Craigslist and decided to message me to see whether or not we could get together or not. His name was Marc, a young black boy who lived in Scarborough. He said he was a shy guy, a virgin, and he watched a lot of tranny videos...

2 years ago
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Alan Gets A Tranny

-------------------------------------------------------------------------- I went to Alan's house after work one day to talk to him. His mom was single and she need a male figure to discuss masturbation since she had caught him doing it. I rang the bell. I heard footsteps on the stairs and then the door opened. "Hi Alan." "Oh, hi Mr. Jones." “Can i come in?” “Sure,” he said holding the door open. “Alan I have to be home soon, so let me just say this quickly: I know your mom caught...

2 years ago
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First Time With Tranny

I had fantasized for quite a while about hooking up with a hot chick with a nice cock. I gravitated towards shemale porn and couldn’t get enough of it. On this particular day I was having a few drinks and browsing the web for my favorite shemale movies. I discovered the gay.com chat forum. Soon I was chatting with this hot asian crossdresser. She was about my age (21 or so at the time) and lived just a few towns over from me. We shared some fantasies and seemed to have a good connection. She...

3 years ago
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My Tranny Teacher 4

This is a fantasy story. Every day left me feeling more horny and excited for our next tutoring session with Ms. Bennett (Becca). I was hard about 90% of the time just going thru all of my special clothing and deciding what I could get away with wearing to school that would light up my teacher and make her clitty into a full stiff dick that I could put to use. After looking at everything I decided that black lace top stockings would be exciting and could not be noticed under my school clothes....

3 years ago
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Threesome with a tranny and a woman part 2

I had just finished fucking and sucking with Bree ( the tranny) and Tammy ( the woman) and we all wanted more. If you did not read the first story please do that so you know what's going on. We were laying there getting our breath back and I looked at Tammy. Now that I knew she was a woman I really looked her over. She was about 5'3" with a fantastic body and shoulder length blonde hair. She had big tits with extra large nipples that looked like pencil erasers only longer. She had a little...

2 years ago
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Tranny Arschfick in der Jugendherberge

Fabianes ersten ErfahrungenFabiane, die ursprünglich einmal Fabian hieß, war eine Tranny und hatte gerade ihren 20. Geburtstag gefeiert. Sie war Berufsschülerin. Als solche übernachtete sie regelmäßig die Woche über in dem Hotel, in dem ich an der Rezeption arbeitete. Dieses Hotel war zwar an sich eine Jugendherberge, aber ganz im Stiele eines Hotels. Somit hatte ich mit vielen jungen, coolen Menschen zu tun. Mit einigen entwickelten sich manchmal Freundschaften, so auch mit Fabiane. Sie kannte...

3 years ago
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Trucker the Tranny

Jermaine Simpson drove his white 2010 Peterbilt raised-roof big rig into the truck stop just outside of the city. He called his friend, Mariah.“Hey, baby,” the dark-skinned transsexual answered.“What’s up boo? I’m at the truck stop,” Jermaine shared.“Okay, oool! I’m on my way.”“Awesome! Can I get a shower at your house?”“Of course!”“See you in a few.”“Bet!”Jermaine’s nine-and-a-half-incher was already hard. He loved fucking her whenever he was down this way. Once he had taken her on a six-day...

4 years ago
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BuildaTranny

Garvey Williams kissed the pretty, effeminate, white boy he had had been secretly fucking since they were high school sophomores. Back then, Garvey was a standout wide receiver with high prospects of moving on to Division One. He had progressed as everyone thought and Jamie Collier, the femboi, followed him to the large state university. Garvey and the Mustangs earned a national championship his junior year. The football prodigy decided that he should enter the NFL draft immediately following...

4 years ago
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My first tranny girl experience got me hooked

I have always wanted to have sex with a tranny. I find these women sexy. In my daily life I dont know any, so I look online find a tranny to fuck. As I look online I find a sexy Cuban t-girl advertising sex. I instantly give her a call and arrange a time to go meet. One thing that turned me on is that she just moved from Cuba and had an spanish accent that turned my dick rock hard. Once I get to her home she leads me to the bedroom. She is 5'5 about 125 pounds. My girlfriend is 5'9 160. So my...

1 year ago
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Fun Time With A Top Tranny

So since I got a good rating for my first sex story, I shall write another one about my first time with a tranny. This happened last year. She was 25, and I was 21. So I am Ash, I am 22, I pretty good and masculine looking. I am mostly a bottom though. I have always been a huge fan of shemales and ladyboys. Respect them and also lust for them :p anyway, so I was in dubai last year and I thought that there might be much more shemales and easier to meet since the place was quite forward with a...

Gay Male
4 years ago
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Tranny Night

Tranny Night: My name is Andrew and I had known Jane since we were very young. She was a precocious child and could play piano and read music from a very early age as well as reading complex novels when most children our age were struggling with reading Enid Blyton novels. I was the brightest boy in our class and would have liked to pretend I was the brightest pupil in the class but Jane's results were always better than mine, although I would not admit it as she was a girl. As...

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