Nate And His Tranny Neighbour free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)

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 with big tits, a pretty female face but a thick juicy cock to be pleased, not a pussy to be fucked. Countless nights spent finger fucking his tight hole to the thought of it being penetrated by a petite woman but powerful cock. Now would be a good time to describe Nathan. Nathan was 5 foot 7 inches, 140pounds and he was in good shape. He loved swimming and competed locally, hitting the pool was his favourite exercise and he shaved all over for a streamlined movement through the water. A 7 inch cock with a nice thickness would have made him a hit but his tight bubble butt was his best feature. Squats allowed a taut ass that begged for the hard fucking that he so wanted.

Nathan groaned, checking his clock he noted the luminous green 11:30AM staring at him. I sat up feeling horny, opening my laptop wiring it into life thinking of what might elicit images might tempt my desires today. I opened a site checking through the various babes on offer to my mind. There was a loud knock on the door. Half eleven? Who calls at that time? Sliding out of bed I reached for a small pair of workout shorts, I quickly checked myself in the mirror and fixed my medium length black hair into a swishy fringe. No need for a top today, 25Cº heat needs no top. Hurrying down the stairs, I opened the door. There stood my neighbour a forty two year old minx, Ms Jez, a curvy woman standing 5'10 with long slender legs and what had to be at least a set of D cup tits. She had piercing blue eyes, poker straight hair and a light touch of make-up except her usual dark red lipstick accentuating her sex goddess look. She stood in some running shorts and a small vest top. 'Hey Jez' I said, 'Hi Nate, was wondering would you be able to help with some moving?'. I'd helped her before, being a single woman some of her garden furniture was heavy for her to lift and besides I always loved a reason to go over. 'Sure Jez give me sec to get a top', ' Hardly necessary in this heat Nate, not like you wouldn't to show yourself off anyway'. I blushed like mad, she had always seemed to be flirty and playfully with me but maybe that's just me letting my hormones cloud my judgement. .

Half an hour later we had finished moving some patio chairs about, the sun had been beating down and I was quite hot, looking over Jez was fanning herself off. She offered me to come inside for a drink, she popped two beers, gladly I accepted the offer. We stood at her breakfast table, the kitchen being connected to the sitting room also. 'So many plans for the summer Nate?' 'No not much Jez, I have a few competitions some might lead to national level'. 'Wow impressive, you definitely look in shape for it anyway'. I blushed crimson again, 'well yeah... hopefully'. I'd realised she was staring me, was she checking me out? No way I thought, ' So I was...' I started 'Shhh' she whispered pressing a finger to my lips. I shuddered her touch was electric, I started deep into her eyes, however she only moved in slowly. I went in for those delicious inviting lips, she pushed me back towards her sofa. She pushed me down onto it, I could smell her perfume, it was spicy and intoxicating. I so wanted to have her, take that tight body for my young prick. She leaned in and kissed me lightly, I went to slide my tongue in, she pulled away and put a finger to my lips once again. 'Suck' she commanded, I took the finger in my mouth and she pushed deep along my tongue, trailing her nail along lightly. My mouth tingled, I hadn't expected this but loved it. She then stood back 'Strip' she commanded. I wasted no time in shredding my shorts off, I stood with my 6.5 inch uncut cock on display. She forced me back onto the sofa. I couldn't wait to feed that pussy my cock. She swiftly removed her vest top, showing a massive set of tits with large pink nipples. I went to reach up for them to suck and tease them but she pushed my hands away. 'Take your time boy' she purred. What a little I thought. She then slid her shorts off, I look at a dark purple thong, shapely fitted around her thin thighs. Staring back at me was a cock! I swallowed hard and looked into her eyes. How the fuck could this gorgeous woman have a cock? What looked to be a big one too. I stuttered 'Jez I don't kno...' ' Don't know what baby? Not ready to have a woman take your tight twink body to please herself.' At those words my cock bounced, admittedly I had always loved shemale porn, women like this so feminine but with a thick cock to play with. However being face to face like this was so different. I reached forward placing my hand on her thong, feeling the throbbing cock within. 'That's it sweetie, just go for it and you'll love it'

I pulled down her thong, her cock bounced out. It was large than mine, she was smooth also. She threw me back onto the sofa, 'I'm going to have so much fun with you honey,' she purred. She held my head and ran her fingers through my hair. 'Ohh such a cutie can't wait to cover that pretty face in hot sticky cum'. I wanted to taste her so badly, I moaned loudly and she responded placing her cock on the tip of my tongue. She slowly slid it in using my head to control me. 'Please me baby'. I didn't need telling twice, I start to suck, unsure of what to do. My mouth felt so full, and I had so little cock in already. I sucked long and tried getting it deeper, I gagged lightly pulling back. 'No sweetie' She forced more of her cock into me. I could feel my throat give and I was accepted more of this meaty cock in my mouth. 'Ohhh baby you're doing so well' Pre cum was running out of my mouth, she took it in her fingers and smeared it over my face. I loved it feeling like such a toy to her primal desires made me so fucking horny. She slipped her cock out of my mouth, still holding my head she bent down and kissed me deeply. I could feel her tongue diving into my mouth, she then bit my lip, I was in heaven, but my cock needed serious release. Sensing this she had me flip over with my ass exposed to her. 'Mmmmm that pink hole is just gorgeous' She playfully slapped my ass. 'Ohh' I gasped. She slowly ran her hands over my bubble butt, teasing my hole and then her hand reached down to my cock. 'Ohhh fuck yes Jez' I moaned as she teased my cock. She leant forward and planted a soft kiss on my boy hole. 'Ohh please' I begged. She knew I needed to get some relief. She started to lick my hole and probe it lightly with her tongue. I often fingered myself watching tranny porn however this was a new league, my cock felt ready to explode as this tranny MILF teased my ass and cock. 'Your hole looks tight, but you had some fun here before haven't you?' I grabbed the sofa hard 'Ohh maybe the odd bit' I rasped. 'Tell me baby what do like to have done?' 'Ohh god finger my ass, please Jez'. I just wanted her to use me so badly, she pushed a finger in and I slid my ass back into it, taking it knuckle deep. She removed her finger and brought it to my mouth, I sucked deep lubing it up, this time a second finger entered, from their she began to finger fuck my ass. ' Ohh yes baby take it like a good boy for me' I moaned loud and I couldn't take it anymore. I needed to feel her hot tranny cock in my ass. ' Please fuck me Jez' I asked, 'Do you really want my thick cock baby, do you need it baby?' 'Ohh god yes Jez, I need that hot tranny cock to fill my boy hole, I want to feel you spread my ass!' With that she lined up her cock to my entrance. She pushed forward and I grunted hard, it was slightly painful but I was so worked up I didn't care. She waited for me to settle then slowly withdrew her cock. She then slammed it back it me, this sent a bolt of pleasure through me and she really began to fuck me. I spread my legs further giving her better access to my hole. She slapped my ass 'take that shemale dick boy' 'I'm gonna fuck you everyday like now boy'. I was in ecstasy, she leaned forward and kissed my neck, dragging her lips to my ear, then back to my neck where she sucked hard. I knew I'd have a lovebite but didn't care, knowing she was marking me as hers was such a turn on. ' Ohh I'm gonna cum soon sweetie'. ' Me too Jez' I gasped, 'I cum first she stated, she grasped my cock and start to milk me. 'Ohh yes boy this hot tranny cum is going deep in that tight hole.' ' Fuck , fuck, fuck' I felt her cock spasm and her cum fill deep in my ass. She slid her cock out and quickly put two fingers in my hole, scooping out her cum. She put the cum over my cheeks, I stuck out a tongue and she grabbed my hair. ' Not yet baby' She pushed me back to the sofa. She slid down to her knees and quickly took my cock in her mouth. I moaned hard, she was an expert, she forced three fingers into my hole finger fucking me hard. My cum was building, 'Ohh Jez I'm cumming' she sucked the head and wanked my shaft. I exploded into her 'Ohhhhh Jez take my cum' I shot my cum into her mouth, she kept it in her mouth and opened to show me, she looked so good with it, she rose to her feet and placed her lips to mine. I hungrily accepted my own cum into my mouth and we swapped. One hand grabbed my hair and she pulled my head back and opened my mouth. I put my cum on display for her. Another wrapped lightly at my throat. 'Swallow' she commanded, I swallowed and she felt my cum glide down my throat. 'That's a good boy'

'Ohh and Nate, I ordered a table to match the chairs too'

Part 2 maybe, please let me know what you all think. :)

0
0

28.10.2022
26
0

Same as Nate and his tranny neighbour Videos

Nate and Ariana

Nate checked the address on the sheet of paper. This is where his GPS had led him, but this was not the computer store he was looking for. The name on the sign said Ariana’s. It looked like some fancy ladies store. College students can’t be choosey. He heard the computer store was hiring and he needed a job; badly. Maybe someone in the store could direct him where he needed to go. He felt uncomfortable walking into the store, but he didn’t feel like he had a choice. Ariana was in the back of...

First Time

Nate and Connie

Well, the week was a very busy one and I was looking forward to getting on my Harleyand getting a good ride in and then hit up a bikers joint for a beer and onion rings.Saturday morning I got up and dressed in bikers clothes and put a few bottles of ice water in my saddle bags. The ride was great, three hundred and fifty miles of hi-way and back roads, the bike ran like a charm and by the end of the ride my mind was thinking about beers and onion ringsSo I dropped into my favorite bikers bar as...

Fetish

Nate and Ariana Chapter 4

After their threesome at the frat house, Ariana saw a difference in Nate. His confidence increased. He began to become more aware of fashion and changed how he dressed. He even trimmed his hair and switched from glasses to contacts. Ariana missed the geeky young man that first walked into her store several months ago. Their romps in the store after hours became less frequent, stopping entirely when Nate found his first girl friend. Ariana continued fucking the young man from their threesome at...

Nate and Ariana Chapter 4

After their threesome at the frat house, Ariana saw a difference in Nate. His confidence increased. He began to become more aware of fashion and changed how he dressed. He even trimmed his hair and switched from glasses to contacts. Ariana missed the geeky young man that first walked into her store several months ago. Their romps in the store after hours became less frequent, stopping entirely when Nate found his first girl friend. Ariana continued fucking the young man from their threesome at...

Group Sex

Nate and Ariana Chapter 2

Nate loved his job at Ariana’s. OK, it wasn’t really the job it was Ariana and the “perks” she provided. Ever since he walked into the wrong place two months ago, Nate had lost his virginity to Ariana, and happily submitted to her teaching him about sex. Ariana was a sex fiend and was ready to go at any time. She quit wearing panties to work, leaving her pussy available at any time. During slow times she’d take Nate into one of the dressing rooms to give him an amazing blow job. Frequently Nate...

First Time

Nandita To Nandini

Hi, To all Iss reader this is my first story hope U all would like it a complete fiction.my self raj i live in Mumbai this story is about my aunty nandita,let me describe her she is in her 30s,lives with her husband and daughter.She is born beauty with an awesome fig of 36.28.40 ..her assets are her huge melons of 36 d and her ass that will give a hard on to any guy who looks at it So now my story starts this was like 5 years ago when I was appearing for my 12 th HSC examination at that time my...

Nate and Dancelle are cousins

Dancelle and Nate are cousins in mother's side. It was long ago when Dancelle loose her parents in car accident together with Nate's father, so Aunt Liza(Nate's mom) were obligated to take care of Dancelle. They only have small house with only two bedroom, one for Aunt Liza and one for Nate. Dancelle shared room with Nate. It was ok for Nate, they had been sharing room for 6yrs now but unfortunately he had to study abroad due to scholarship and he grab the chance. Aunt Liza at Dancelle are left...

Incest

We follow what happens when a petite bi guy that dresses as a tranny is regularly fucked by his neighbour

The best thing about living by yourself in the suburbs of a city, is that you have all the varied amenities of a city, with plenty of quiet roads, dark alleys, and gardens to melt into which serve my sexual leanings very well! If I explain to you a little about myself and exactly what my sexuality is, perhaps you’ll understand more fully? My name is Adrian Cooper, I’m 27, single, 5ft 6in tall, and weigh 10-stone (140lbs). Although I’m very slightly built, nature has been...

Nate and me

The following story is strictly fiction and for erotic fantasies . And the summer was there! It had been there for months. It was now July and I had gone north to see my cousins. there were three of them ages 7 ,9, and 11. The two youngest were girls and the oldest a boy. I had always enjoyed visiting my cousins up north, it let me get way from my parents and hang with my little cousin Nate. At the time I was 14 , and as stated earlier he was 11. I had been staying with them for a couple...

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,...

Tranny

What do you think “Sluts with Nuts 4,” “One Hung Bitch,” and “My Girlfriend is my Boyfriend” all have in common? If you guessed they all had tranny babes doing kinky shit, then you were right. All of those titles are from DVDs that you can view for absolutely free on the site I have for you this time around. What’s not to love about watching some thick dicked chick fuck some hot bitch in the ass? I get that it’s not everyone’s cup of tea, but damn you’re missing out on some good shit if you...

Premium Shemale Porn Sites

The Cabbie and The Tranny

The Cabbie and The Tranny By Michele Nylons Twas the middle of Manchester one winter night; and the only cab on the rank, The driver was reading a 'Score' magazine; whilst quietly enjoying a wank. He was dreaming that Venus was kissing his penis; and the shaking was making him tired, When a tranny called Lena, with false tits like Sabrina; came over and gently enquired. "How much to Oldham" she said; well the cab driver nearly dropped dead! He got such a shock he let go of his cock;...

Nate and Ariana Chapter 2

Nate loved his job at Ariana’s. OK, it wasn’t really the job it was Ariana and the “perks” she provided. Ever since he walked into the wrong place two months ago, Nate had lost his virginity to Ariana, and happily submitted to her teaching him about sex. Ariana was a sex fiend and was ready to go at any time. She quit wearing panties to work, leaving her pussy available at any time. During slow times she’d take Nate into one of the dressing rooms to give him an amazing blow job. Frequently...

Andy Has Dinner With His Neighbour

Andy had just moved into his first house. It was only a small house, but he liked it and it was his.The one thing he was not though was a good gardener. His efforts to make his garden look good were, to say the least, pathetic. He admired his next-door neighbour. Her garden was immaculate.One hot Saturday, Andy was out in his garden, trying to make it look semi-respectable. His neighbour, Carole, came out and lovingly attended to what he considered was already perfection. He also thought that...

Occupations

Tranny Boy Posse Tales of the Evil FagHag

This is just a story, okay? I don't advocate having sex with underage people and I realize that probably most cross-dressers aren't gay. Yeah, and most females who choose to hang around gay dudes aren't evil either. Most 'fag-hags' seem to be nice people and some may even resent that term of endearment. And it's never been my intention of slandering the Vegan lifestyle, Wicca, Druids, the rest of the occult and all the other great religions of the world. This is just a story, okay? It...

Tranny Motel

Tyrone and Kimberly Woods kissed as all of the guests at their house party cheered them on. It was their first anniversary and they were celebrating this night with family and friends. There were close to forty people in attendance – most of whom had brought some form of alcohol and all of whom had brought a gift. There was great music and excellent barbecue as Kimberly’s dad and Tyrone’s uncle manned the grill. Folks were laughing, dancing, and having a great time. In one corner of the yard,...

Slovene Tranny and Her American Men

Milena Dorin awakened from her slumber. She grabbed her iPhone and pressed the button to see the time. It was 6:14 a.m. She decided to get up and bathe. She walked into the master bathroom of her palatial two-bedroom, two-bath downtown condo. She pulled her douching apparatus from beneath the sink. She cleaned out her 40-inch ass. After completing that task, she hopped in the shower. The steamy, hot water felt good against her milky-white skin. She scrubbed her curvaceous figure with a purple...

SARAHS NINE INCH TRANNY

For the last week my man has been tempting me with images of hung trannys. They have an added dimension when it comes to sex - tits and a cock, preferably both in generous doses. By the end of the week I am hanging out to experience a new one. One of the images he showed me was a side on shot of a tranny in panty hose with her back to the wall flaunting a huge erection thrusting out of her panty hose that really piqued my already strong libido. Another was a pic of tall slim tranny sitting...

SARAHS NINE INCH TRANNY

For the last week my man has been tempting me with images of hung trannys. They have an added dimension when it comes to sex - tits and a cock, preferably both in generous doses. By the end of the week I am hanging out to experience a new one. One of the images he showed me was a side on shot of a tranny in panty hose with her back to the wall flaunting a huge erection thrusting out of her panty hose that really piqued my already strong libido. Another was a pic of tall, slim tranny sitting...

TRANNY THREESOME

“Ask me again baby,” he groans as he supports himself above me on his hands and toes and frantically slides his full eight-inches into me. “Would you like to blow a tranny while I watch?” “Yes, baby yes, so fucking good, yes,” he moans as we orgasm together. I had just the tranny, Rosie, in mind, I hadn’t told Roger but she propositioned me recently and hinted that she would enjoy me and Roger at the same time. We always go to some trouble to dress or undress to turn on our guest when they...

TRANNY THREESOME

“Ask me again baby,” he groans as he supports himself above me on his hands and toes and frantically slides his full eight-inches into me. “Would you like to blow a tranny while I watch?” “Yes, baby yes, so fucking good, yes,” he moans as we orgasm together. I had just the tranny, Rosie, in mind, I hadn’t told Roger but she propositioned me recently and hinted that she would enjoy me and Roger at the same time. We always go to some trouble to dress or undress to turn on our guest when they...

Tranny in Croatia

I started crossdressing as a teenager. I had a young mom, who always had some interesting and sexy clothes. I was 13 the first time I took her clothes (she was 31 at the time). I took a metallic silver jacket and some lacy thongs, and I put on her pink lipstick. I took a couple of photos, but they all came out blurry. But I liked how it felt, the only trouble was I did not know what to do... it felt wrong enough to hide it but right enough to get me interested. I dressed up quite often, but not...

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....

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...

Andersonville 12 The Day Linda Anderson Came To Town

I slid the report into the proper file just as he walked into the room. Dennis Butz stood there wearing his three-piece suit, looking as handsome and charming as any man could. But I was not to be tamed by his charm. "Hello, Linda," he said with a friendly grin. "Judge Herns isn't in today," I replied back in a frosty tone. "I'm not here to see her." "My plane leaves in less then an hour Dennis, what do you want?" I slammed the file drawer shut and walked past him to my desk...

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...

My meeting with tranny milf Sandy 54 part 1

Wanna tell you about my meeting with Trannymilf Sandy 54!I met Sandy through an add in a pornographic magazine I was 23 then so she was 31 years older than me. Wanting for long to meet a much older tranny beauty I got really excited when she agreed to meet me. We met in her apartment after I rang the doorbell a beautiful woman in her midfifties with a white dress long blond hair,white nylonstockings and white high heels opened the door. Her face had a heavy-makeup I was stunned by her looks....

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

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...

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

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...

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...

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...

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

Nate and Ariana Chapter 3

When Nate and Ariana were in the boutique together Nate let his shy, geeky exterior down. Ariana’s attention and their sexual exploits together gave him a confidence he had never experienced before. However, when he walked out the door, his shield went back up, his confidence gone. He was a computer geek, and he knew how people looked at him. He wasn’t one of the jocks or popular guys on campus. He was jealous of them. They were so confident with girls. He knew he’d never have a relationship...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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

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...

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...

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...

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...

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...

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...

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....

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...

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...

Porn Trends