Flat Mates - Chapter 2 - My First Visit To A Tranny Club free porn video

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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 about going into a gay and tranny bar. I'd stand out like a sore thumb." Gloria hastened to reassure me that on live-band nights quite a few straight guys attended but I still was nervous about the whole thing. "Look," said Gloria. "I've got an idea. If you are nervous about going as yourself, why don't we dress you up a bit and you can pretend you are playing a part in a play?" I backed off sharply. "Sorry," I said, "but there is no way you are going to get me into a dress!" "That wasn't what I was thinking of," Gloria responded. "My idea is to go for a slightly androgynous metrosexual look. If we tidied up your hair a bit; applied a little discrete make-up to your eyes; and you wear some of your brighter coloured clothes, you will blend in the crowd but, at the same time, not be too outrageously over the top." I still wasn't certain, but Gloria pleaded with me to let her try and, as we still had most of the afternoon ahead of us, I finally agreed to let her see what she could achieve - with the proviso that if I wasn't happy with the result, I could veto the whole idea. Gloria agreed and immediately set about my transformation! "The first thing you need to do," she started, "is to give yourself a very close shave; take a shower and wash your hair. (I hadn't cut my hair since coming up to University as the perceived "cool" image was for longish hair held back in a small ponytail. My hair was coming along nicely although it was still a lot shorter than Gavin's). I did as I was instructed and 10 minutes later was back in "Gloria's room" with a towel wrapped round my waist. "I'll deal with your hair in a minute," said Gloria. "But first why don't you get out those clothes you bought at the Vintage Emporium the other day." ("Retro" was currently cool, so I had been busy building up my wardrobe through visits to charity and vintage clothing shops. Only a few days previously I had struck lucky and found a cache of wonderful garments.) I hurried to my bedroom where I got rid of the towel and pulled on a pair of underpants and my dressing gown. I took a number of hangers out of my wardrobe on which hung my new purchases. I took them in to Gloria. She held each hanger up to the light and gave the clothes on it a serious scrutiny. "I think the cream flared trousers and the blue velvet jacket," she said. "You don't have an appropriate shirt, but I can find something that will work with them." "I think we ought to start with your make-up," she continued. "I promise I won't do anything extreme, but a little "grooming" won't go amiss." She sat me down in front of her dressing table and proceeded to apply a little pale blue and white eye-shadow to my lids and to emphasise my eyes with a little mascara and liner. A very pale pink gloss was smoothed over my lips and my nails were trimmed, shaped, and painted with an almost neutral, semi-gloss, pink varnish. Whilst my nails were drying, Gloria got out her hair-dryer and brush and started blow-drying my hair. She teased away at it and, when she was finished, I saw that she had given it much more volume. It was still my basic hairstyle but now it fell gently in waves around my face. Together with the make-up, my image was softened and - yes - more feminine! "Now let's get you dressed," announced Gloria. "Try this on." She passed me a navy-blue shirt, decorated with a pattern of big red roses. At least I thought it was a shirt until I came to try it on when I discovered, to my horror, that it was actually a ladies' blouse! "I can't wear this," I protested. "Nonsense," Gloria replied, "it is a great shirt and will go really well with your jacket. It used to be a favourite of mine until I lost weight and it was too big for me. I couldn't bear to get rid of it so it has been hanging in the back of my closet for ages. I'm so glad to find another excuse to give it an outing." Grumbling I pulled it on. I had to admit it did fit well, if a little snugly across the shoulders. Obviously it buttoned on the wrong side, as far as I was concerned; and had a narrow frill running round the front and at the cuffs. I eventually managed to fasten the small, pearl buttons. Gloria looked at me critically. "I think you should leave the top two buttons undone," she mussed and, reaching across, did just that. "Now try your trousers," she continued and I hastily stepped into them and pulled them up. They were a genuine pair of 1970's trousers with narrow legs at the top, flaring below the knee into a turn-up that completely covered my feet. They were very snug fitting around my hips, with the belt-line being at "hipster" level. "No, no, no," Gloria shrieked, "that won't do at all. Ladies worry about showing a panty-line; but your boxers are a positive disgrace; they bulge out all over the place. They simply will not do with those trousers! Get them off and try these." She passed me a simple white thong. "I know it's a girl's garment," said Gloria, "but I know from experience it is wide enough in the crotch to hold you securely in place and it won't show lines all over your bum!" I turned my back on her and swapped over underwear. I pulled my trousers back into place and Gloria had me turn slowly round before expressing herself satisfied that nothing untoward was visible. "I think this will go well with the shirt," mussed Gloria, passing me a narrow red belt to thread through the loops on my trousers. When it place it did complement the shirt but, like that garment, was clearly feminine; the butterfly buckle was a bit of a give away for a start! Still I had agreed to let Gloria complete her work before exercising my veto, so I bit my tongue and let her continue. Next up, she fastened a heavy gold chain around my neck. On it hung a medallion, embossed with the Yin and Yang symbols of polar opposites. (In my case I guessed "male/female"). Gloria allowed me to buckle my gold coloured watch on my left wrist, before fastening a gold charm bracelet on my right. Only two charms hung from the bracelet; tiny figurines of Mars and Venus - once again an open comment on my androgynous state. Gloria then clipped a pair of pearl earrings to my lobes. "I'm glad to have found a use for these," she enthused. "I picked up a box of odds and ends of jewellery in a charity shop the other day and amongst the stuff were a few pairs of clip-on earrings. They are no use to me and I was about to sling them in the dustbin. They look good on you, however!" "Try the jacket," was Gloria's next command, so I shrugged my way into it. It was also a genuine 1970's item and, given its age, in surprisingly good condition. Single breasted, it was tightly waisted and fastened with a single button. "Mmm, gorgeous," Gloria murmured, fussing around until the frills at the neck and cuffs of my shirt were arranged to her liking. She undid a further button on the blouse. "I think the way your pendent nestles in your chest hair is very sexy," she announced. "At one and the same time it screams both masculine and feminine; just the effect I was trying to achieve!" This only left my feet unsorted. My toes just about protruded from under my flared turn-ups but I was still unshod. Gloria passed me a pair of tan, nylon, knee-high stockings. Well, "in for a penny, in for a pound" I thought resignedly and, sitting down, I pulled them on, taking care not to ladder them by snagging the material on my toe-nails. Gloria then knelt on the floor and slipped my feet into a pair of red leather, zip- sided, ankle-boots. They were quite obviously ladies' shoes, a fact which the two inch heel did nothing to disguise! "Stand up and let's take a look at you," commanded Gloria. I did as she said and stood there whilst she walked slowly round me. "Well if I do say it myself, I've achieved exactly the image I wanted," she announced. "What do you think?" I turned to the full-length mirror on the wall. The image of a very different person to the one I was used to gazed back at me. It was clearly still "me", but softer, more feminine. The make-up I was wearing wasn't immediately obvious to a casual glance but definitely enhanced the appearance of my eyes, whilst the gently waving hair softened the contours of my face. The blue and red-flowered blouse went surprisingly well with my navy-blue velvet jacket and the flares on my trousers effectively hid my heeled boots from sight until I started walking. I had to admit I rather liked what I saw; it wasn't what I was used to but I certainly didn't look ridiculous. "I can't believe what you have done," I stammered. "I thought I would look some sort of painted fool, but I don't; I really like what you have done." "Then you'll come out with me to the club tonight?" squealed Gloria in excitement. I had trapped myself. Because I hadn't been dismayed by my appearance, I had tacitly accepted that I would be willing to go out in public dressed as I was. "OK," I sighed, "I guess I can't argue with you. You have done what you said you would and I will stand by my side of the bargain." "Ooh you will make a scrumptious date," enthused Gloria, "the other girls will eat their hearts out!" Seeing a look of horror flit across my face, she laughed. "Don't worry," she said, "I'm not going to eat you; we are "mates." Remember, I'm just going to make sure we milk the opportunity for a bit of fun for all that its worth! Now, if you are ready, we had better call a cab. I don't think you are ready to get on a bus dressed like that just yet!" Gloria passed me a blue leather shoulder bag. "You aren't going to get anything in your pockets without totally ruining the line of your clothes," she informed me. "Tonight you are going to have to carry a purse like the rest of us girls!" Much as I hated the idea of carrying a handbag, I could see the logic of what she was saying, so quickly transferred my wallet, ID, phone, and keys into my new bag. We were ready for the "off"; what had I let myself in for? It didn't take long for our cab to turn up at our door. I was a bit worried about the reaction of the driver, but I needn't have bothered. "Evening girls," he greeted us. "Off to the Village are we?" "Yes," replied Gloria, "the Purple Python please. (For those who don't know, "The Village" in Manchester is an area noted for its warm welcome to gays, lesbians, and the transgendered.) There wasn't much traffic about and before long we were pulling up outside the Purple Python. Like many cities, Manchester had a lively club scene with new venues arising and others disappearing all the time. The "Purple Python" had proved to be an exception and had become a popular venue, noted for its live music and spectacular drag acts. Tonight, I was relieved to learn, was a music night; any drag would strictly be amongst the clientele! There was a queue of people at the door waiting to get in, but Gloria was obviously known as a regular visitor as we bypassed the line and gained immediate admittance. "Thanks George," said Gloria to the doorman, giving him a quick peck on the cheek. "Come and see me when it's your break and I'll buy you a beer." "Thanks Gloria," George responded, "see you later." Gloria checked her coat and we descended into the basement where the club was situated. It was really very smartly decorated and I could see why it would be popular. There was a large bandstand to one side of the room and a small stage on the other. Ranged between were a number of tables, not too closely packed for comfort; whilst round the walls alcoves provided areas of greater privacy. The place was already quite crowded and Gloria looked around to see if any of her friends were in. "There they are," she squealed and hurried me over to a large table near the stage where some four or five girls were already seated. Well I say "girls" and, looking at them I couldn't be absolutely sure, but I guess most, if not all were cross-dressed men. "Keriss, let me introduce Tessa, Tanya, Simone, Suzy, and Phyllis. Girls this is Kerris." Now Gavin/Gloria normally addressed me as "KT", as did all my other friends. For some reason, tonight she had decided it was necessary to use my "Sunday best" name; the one that I hated. "Oh no," I groaned. "Please don't call me "Kerris," make it "KT," like the rest of my friends." "Ooh I knew it," shrieked the girl called Suzy. "She may not be fully dressed yet but she is still a girl at heart. Welcome "Katy," come and sit beside me." I groaned inwardly; I'd made another mistake. By innocently giving them the name by which I was usually known, I had made them think I thought of myself as a female. I grinned weakly; "Well that's not how it is normally pronounced, but I guess I will have to live with it; "Katy," it is!" The girls all clapped as I sat down next to Suzy, who shuffled along the banquette to give me room. "So you are Gloria's mysterious flat mate," Suzy said, with a wicked grin. "She has told us all about you and we have been so eager to meet you. And here you are at last!" "Well I hope she hasn't told you anything awful about me," I said in reply. "Because if she has its all lies." "Not at all," responded Suzy "She says you are a great flat mate and that it was a lucky day for her when you turned up." "Then its all true," I laughed. Gloria's face turned red; "Honestly I haven't said much about you at all," she protested. "This lot are just so nosey!!" "Its OK," I reassured her. "I'm sure any friends of yours will be people I would like to get to know." This remark produced a ripple of applause and a few smiles around the table. Drinks were quickly ordered and in no time at all I found myself being quizzed about my background; reason for being in Manchester; and why I was only partially cross-dressed. I hastened to explain that I wasn't actually a transvestite and had only dressed in this way to please Gloria. "I don't believe you," asserted Suzy. "The fact that you were prepared to turn up here tonight dressed like that knowing you were going to meet new people means that, at heart, you are just like the rest of us; men with a strong feminine side which they enjoy displaying. Mark my words; one day you will come to accept that this is true." I decided I had protested enough and that further denials would be counterproductive. Fortunately, just then, it was announced that the band were about to play their first set and we all settled back to enjoy the music. They really were very good and I was please to find that all the things I liked them for were actually in their music and not the result of some electronic trickery in the recording studio. They played for three-quarters of an hour and then an intermission was announced. The girls all leapt up and hurried off to the ladies room. I called out I would get the next round of drinks in. Accordingly I strolled over to the bar. As I was waiting for the barman to pour my drinks, I became conscious that the man standing next to me was scrutinising me most carefully. When I realised I had noticed what he was up to, he looked me in the eye, smiled, and said; "Hallo gorgeous; are you on your own tonight?" I didn't know what to say; it was my worst nightmare coming true. Here I was in a gay bar; partially dressed in women's clothing; being chatted up by some predatory male! My tongue stuck to the roof of my mouth and I found I couldn't say anything in reply. "Cat caught your tongue?" he continued. "A lovely little thing like you shouldn't be out in the big bad world all on your own. Let me buy you a drink and we can get to know each other better." By now I was really panicking. Suddenly, to my profound relief, a friendly voice intervened. "Shove off Alec; this one's mine; I saw him first." It was Gloria, and I had never been so glad to see anyone in my life! "Oh Gloria, he's with you is he? Well in that case no hard feelings. I'm sorry I scared you." This last remark was addressed to me. "My name's Alec and, as Gloria will tell you, I'm really quite harmless. But you are a real turn on and I couldn't resist trying my luck with you." "Not at all," I stammered, "think nothing of it." Just then my tray of drinks arrived and picking it up I hurried back to the table with Gloria. "Thank goodness you turned up when you did," I said. "I just didn't know what to do," Gloria laughed. "Oh Alec is alright. As you must have realised he is a gay as they come but, for some reason, he can't resist trying it on with any new trannies who come in, even though he knows that the likelihood is that most of us are straight. "But I'm not a tranny," I protested. "Well strictly maybe not," Gloria replied, "But to the casual observer you do look pretty feminine. I'm sorry if my wanting you to join me tonight has caused you too much embarrassment. I promise I won't put pressure on you again." "It's OK," I replied. "I knew I was laying myself open to this sort of treatment when I agreed to dress this way and come to the club. It's just that when something actually happened, it came as a bit of a shock. Apart from anything else, no-one has ever told me I look gorgeous before!" We all broke into laughter and this served to dispel the tension. The band started its second set and, by the time they had finished playing, Gloria and I had decided it was time to call it a night. We both had early starts at Uni in the morning. We made our farewells to the rest of the party and I was touched by the genuine warmth shown me by the girls with their wishes that they hoped we might meet again soon. "Remember," Suzy whispered in my ear, "next time it's a dress for you young lady!" "In your dreams," I responded with a laugh and we all parted good friends. As Gloria was collecting her coat, Alec came up to me. "I'm really sorry about what happened earlier," he said quietly. "Suzy has told me how you come to be here and that it is your first time even partially dressed. I hope I haven't scared you off from coming again. Maybe next time we can have a drink together without any side agenda." I assured him I had recovered from my shock. "I'd be happy to have a drink with you," I told him, "but it is highly unlikely I'll be in here again; this has definitely been a "one-off," for me!" "Well you never know," Alec replied, "Look out for me if you do come in." We shook hands and Gloria and I left the club in search of a taxi. Fortunately we found one quite easily and within twenty minutes we were safely back inside our house in Gladwin Road. We collapsed into two chairs and kicked our heels off. (I had a bit of a struggle with the zips on mine!) "I never realised how tired your feet get in heels," I grumbled. "Well we women have to suffer for our beauty," smiled Gloria. "Did you enjoy yourself this evening?" Surprisingly, against all expectations, I did," I replied. The band was brilliant and your friends are great. I was afraid they would be all camp and gushy, but they are really very nice and normal. Tessa, Simone and I had a long chat about whether City or United are going to take the Championship this year. Gloria laughed out loud and it was some while before she could recover her composure. "Look, one thing you need to realise is that trannies and cross-dressers are men just like you. They enjoy the same things you do. It is just that from time to time they need to express their feminine side by dressing up. Don't confuse us with transsexuals, who are driven by a totally different agenda." I groaned that I was too tired tonight to get embroiled in the finer distinctions between different reasons why men might want to wear dresses. "OK," said Gloria. "Let's turn in. Do you want a hand with removing your make-up?" I thanked her but said no; she had explained the process earlier and had given me a couple of bottles of make-up remover and a roll of cotton wool. "Just get the face paint off tonight," advised Gloria; "Leave your nails to the morning and I'll give you a hand. We said our goodnights and Gloria leaned over and gave me a peck on the cheek. "I just want to say "thank you". You are very brave to have gone along with my suggestion and I'm really glad you had a good time. As you have never felt the drive to cross-dress it was quite something for you to do for me, and I appreciate that very much." We retired to our rooms and, after carefully cleaning my face; I collapsed into bed, conscious that I had had just a bit too much to drink!

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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...

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...

2 years ago
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Flat Mates Chapter 6 Coming Out the Other Side

FLAT MATES Chapter 6: Coming out the other side I slept very heavily and was only woken by Gavin bringing me in a cup of tea. "I thought you might need this," he said with a grin. I groaned; "I've got a hell of a head this morning and I can't blame it all on the booze." I then proceeded to enlighten Gavin as to what had happened the previous evening. "I could kick myself," I concluded. "Everything had gone fine; it was a brilliant evening; and Alec and I were starting to become...

4 years ago
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Riverbank Tranny Fucktoy

Hello to all of you that read my first true story about outdoor sex. This is another account of a meeting I had in the middle of a city near a river. It was late one summers evening when I met up with this sexy young Portugese stud I had been messaging on a gay dogging site. I had been chatting to Fillipe for a couple of hours, and we were both getting hornier and hornier with each new message that we sent. It was me that asked if he would like to meet that night, and he of course said yes....

1 year ago
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Sissy Tranny Annie Slutty Fantasy

I have been dressing since an early age, dressing in my mothers stockings, suspender belt, bra, panties and heels. I used to feel my smooth legs and my cock would get hard straight away. I love how my cock looks when im dressed as a sissy slut and from that early age all ive ever wanted is to have a horny guy in front of me, with his cock hard knowing that he wants to fuck me. My fantasy and dressing got a lot more sluttier when I first in with my first love. Her name was Claire and she loved...

3 years ago
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Flat Mates Chapter 4 Suzys Party

FLAT MATES Chapter 4: Suzy's Party I had thought that my purchase of a single dress for Suzy's party would complete our feminine business and that we would now head home and I could get back into sensible male clothes; but it was not to be! Whilst I had been preoccupied with Frankie and deciding which dress I was going to buy for Suzy's party, Gloria had become bored and had moved away to rummage through Frankie's sale rail. No sooner had I said I would take the black velvet dress...

3 years ago
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Flat Mates Chapter 7 Epilogue and Intermission

FLAT MATES Epilogue and Intermission! The evening at the Purple Python passed all too quickly and Gloria and I revelled in being the centre of attraction. I was so pleased Gloria had insisted we come. I knew now that I wouldn't stop cross-dressing. I loved the all the sensations associated with tight corsets; floaty dresses; the tug of suspenders; and the click of high heels on hard floors. Painting my face with make-up and becoming a different person for a few hours was now very...

1 year ago
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My black tranny wife part 3 final

Heather's dress or lack of was amazing. It was white and floor length in the back. It was open down far enough exposing half of her tight ass. The front was cut open down to her naval it was covered in very sheer lace, so the inside of her tits and her cleavage were easy to see. From her waist down, it was also open. She was wearing a sheer G-string. She must have been excited because you dick was semi hard and it really filled out her panties. If you looked close enough you could see her dick...

3 years ago
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Flat Mates Chapter 3 My Next Step

FLAT MATES Chapter 3: My next step. The next morning two wan, pale figures were to be discovered sitting at the kitchen table, drinking strong black coffee and not talking much; we had both had too much to drink the night before at the club and were now mightily hung over! A series of grunts served for "how are you feeling", "do you have any aspirin?" Eventually duty called and we had to drag ourselves upright and head into town for our lectures. By the time I walked into my lecture...

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...

2 years 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...

4 years ago
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Flat Mates Chapter 5 My First Date

FLATE MATES Chapter 5: My First date The next day was Sunday and, after I eventually dragged myself out of bed, I found I couldn't settle to anything. My "date," with Alec hung over me like a cloud. Now that I had sobered up I was very worried that I had agreed to go out with him and, if I could, I would have cancelled our outing. Foolishly though, whilst I had given Alec my address and phone number, I had neglected to ask him for his. There was no way I could get in touch with him;...

4 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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Tranny in Toronto Chapter 4 Valentines Day Threesome

Introduction: Message me on forums and tell me whether you like my story or not. Thanks. I wrote this story in an hour, let me know what you think about it. Have a happy Valentines Day. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Discreet Couple Lookn For Valentines Day Fun – mw4t (DownTown T.O) Wife and I want to fuck a lovely female tranny on Valentines Day. Must be bisexual, message me. ________________________________________ Hello, I hope...

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...

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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...

3 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...

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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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...

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...

4 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...

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...

2 years 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...

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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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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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...

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
3 years ago
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Flat Mates Part 2 Chapter 9 A New Term

FLAT MATES - Part 2 Chapter 9 - A New Term When I dropped off the bus at Gladwin Road and entered the house I shared with Gavin, the place was empty. Gavin was obviously "in residence" as demonstrated by a pile of unwashed dishes in the sink, but he was clearly out. I went upstairs to my room and unpacked my bag. Needless to say, Mum had washed all my dirty clothes, so I came back to Manchester with a bag of freshly laundered things. I had successfully managed to conceal Gloria's...

2 years ago
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Flat Mates Part 3 Chapter 11 Summer in Manchester

FLAT MATES Part 3 - Chapter 11 - Summer in Manchester It was summer and the end of my first year at the University of Manchester Institute of Science and Technology. All through my last year at school I had looked forward to getting away from home for the first time and going to University. Don't misunderstand me, there was nothing wrong with my family life; Mum, Dad, my two sisters - Madeleine and Fiona - and I enjoyed a close, loving relationship at our home in Scarborough. It...

1 year ago
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my first tranny pt 1

you always remember your first time. I remember my first blow job from an ex. (believe me, thats another story.) the first time I touched a pair of tits. the first time I ever ate pussy. the first time I fucked a woman in the ass. & I'll always remember the first time I was with a tranny.her name was brooke. I always wanted to be with a tranny because I was always curious. I mean, shes a chick right. but then she has a dick. you all know some trannies are drop dead beautiful. this one was....

3 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...

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...

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