Shemales Porn Stories
Page 113

The Transformation part II

I was in the closet dangling surrounded by mirrors for what felt like an eternity. Mistress Anna, my once friend now dominatrix, had helped me to the best orgasm of my life but my penance was to stay handcuffed in her closet seeing my sissified self in all the mirrors she had set up around me. I felt ashamed and aroused all at once. It was probably a few hours later that the plug finally slipped from my ass as I started to doze. The glass plug thudded on the carpet and woke me from my daze. I could hear footsteps.

She was gentle with me. She carefully lifted me and unlocked the handcu... Continue»
Posted by fictiong 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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My Early Crossdressing

I started cross dressing around 12. At first it was knickers or tights. As I got older I started to get more serious with it. Just after I turned 16, I'd often go out round the streets round town dressed in full girls clothes. I'd always prefer going out late in the evening in winter, as I'd not pass many people and id normally only pass a few cars, some would slow down as I walked along the side of the road.

One day I was home alone, my parents were away for the week and my s****r was staying with her boyfriend. I turned up the music and got dressed from head to toe. I was pretty much smoo... Continue»
Posted by VirginAsAGirl 3 years ago  |  Categories: Gay Male, Shemales  |  
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FUCKING UNCLE BOBBY

The title of this story isn't really accurate as I wasn't fucking Uncle Bobby see Uncle Bobby was fucking me! He wasn't really my uncle he was just my mother's boyfriend but he lived with us so it was kind of like he was my Dad I really like him a lot he gave me lots of attention and took me places and gave me money for doing chores for him he really was a good guy! He had a boat and it was a nice one too he kept it docked at the Marina and one weekend he asked me if I wanted to go fishing with him well I loved to fish and I loved boats so hell yes was my response and we set out to go fishi... Continue»
Posted by laceysgirl 2 years ago  |  Categories: BDSM, First Time, Shemales  |  
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My first time

I sat in the car outside the address and to say I was nervous is a understatement. This was the first time I had ever done anything like this and I was half thinking of just driving away.

I had got messaging to Sara a month ago after liking the pictures they had posted. I was really in to clothed sex and the pictures showing Sara in a selection of boots whether they be leather or pvc, knee high or thigh high I didn't care as long as they have a stiletto heel l love them.

As for clothes I get hard for the slutty secretary look, a nice tight pencil skirt with some stockings and high heel... Continue»
Posted by big_rob49 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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How Nick became Nicki. A sissy story

This is the story of Nick. Nick was straight.
It was Friday night and she was getting ready to go out, she had something special planned tonight. She had her favourite pair of red and black lace lingerie on, the panties cupping her round smooth cheeks, her light blue pencil dress that hugged her figure and gave her a passable cleavage, white heels that make her look sexy even though they squeezed her toes and rubbed her heels and she had barely got the hang of walking in them. She had done her make up too, as well as she could, a little eye shadow and a cherry red lipstick. Her stomach was af... Continue»
Posted by ilgreturns 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Becomming Alanna - Part 3

We went up stairs to the kitchen and she had me start to help her ice down beer and get bottles of booze out and open. There was a large bar but I noticed not much in the way of food. I helped tidy and set up cups and get ice and then with a sudden shock to my heart the doorbell rang. As it did I caught a glimpse of myself in the mirror. I looked like a girl and I looked like quite a slut, I was panicked, I had to hide I thought but as I looked around the only entrance to the room was blocked by Samantha. She turned with that evil smile and winked at me. Alanna, these are my… friends I told yo... Continue»
Posted by KristyQuinn 3 years ago  |  Categories: Hardcore, Shemales, Taboo  |  
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Office Fun - Part 2

Marcia was sitting in the car park of the office, about to leave having just finished work, when she saw Lee walk out of the building and head towards his car. It had been four days since they had fucked in the office, and she was eager for a second round. She checked herself in the rear view mirror before beeping the horn. Lee looked towards her and she beckoned him over, winding down the window as she did.

“Hey,” she said with a smile.

“Hi,” he replied, ducking his head in through the window. She caught him taking a quick glance at her cleavage.

“You wanna come to my place for some ... Continue»
Posted by gellid 4 years ago  |  Categories: Shemales  |  
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He or she? It did not matter to me!

I was sitting in my small apartment watching TV and having a few pipes when I heard a ruckus in the hallway. It was my room mate Joel and some of his friends retuning from the pub. When they knocked on the door I answered and there he was with some girls he knew but who were all strangers to me. As they entered I noticed Candy, a tall (obviously) male dressed in a bright yellow top and skirt, black stockings, high heels and the most outlandish purple eye shadow I have ever seen. As she passed me she smiled and asked where the bathroom was.

A short time later we were sharing some lines and ... Continue»
Posted by sydguy 3 years ago  |  Categories: Gay Male, Shemales  |  
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Summers In Mexico Can Be Trouble

It was the end of spring when Xavier got his job on the plantation. His prospects had really taken a hit after he'd finish high school a year earlier. Without the money for college, his search for employment had dragged him south of border into Mexico and onto a local plantation just outside of a border town with this seasonal job.

Spring gave way to the hottest summer anyone could remember in Mexico. High temperatures didn't stop the crops from needing to be harvesting. Xavier didn't have any real problems with the other workers except for a group of three women. Well, they weren't really ... Continue»
Posted by germanboi4bbc 2 years ago  |  Categories: Shemales  |  
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My night of first times!!!

I was sitting in the bar with my friends when she walked in. Black short dress, low cut neckline. I can see the garter straps holding her stockings. I think that is what caught my attention first. I had seen garters and stockings in movies but never in real life and her legs looked great. I couldn't keep my eye off her all night. I had to seem like a stalker with my eye's, I wasn't paying much attention to the conversation at the table with my friends she was lust at first sight. I had to make a restroom trip and when I walked out she was standing there. My heart skipped a beat and my stomach ... Continue»
Posted by Trudru 5 years ago  |  Categories: Shemales  |  
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The Apartment!!

I had been given notice to quit my flat and was having trouble finding one to suit. Rents were way to high and the flats were to small. In desperation I appealed on facebook if anyone knew of a flat for rent that was not to expensive. I was amazed to receive a reply from a friend of a friend! I knew him a little but had never had much to do with him. He was leaving his flat and needed to find someone to take it over. He told me that he thought it would suit me. As it was just a message I was not able to ask him what he meant. I applied to the address that he gave me and got an e-mail that eve... Continue»
Posted by dasilva1672 20 days ago  |  Categories: Anal, Group Sex, Shemales  |  
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First time fun

Been dressing for about ten years, started with few items now got full wardrober. Gone the extra mile by shaving all over and shedding some serious pounds to look good. Found a great site in US who sell made to measue mens CD TV Clothing so know I look good. Anyway, on a few websites and cam wanked a few times, but a while ahgo something caught my eys, or should I say someone!!!
Get loads of messages on AFF from loads of guys but its the CD ones that attracts me until had one from a guy who said was shaved ALL over. I adore shaved, I hate hairs, I wont 'play' with anyone in hair at all.
We e... Continue»
Posted by aroannecd4u 3 years ago  |  Categories: Anal, Shemales  |  
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A cum slut is born

There's little doubt about what turns me on most -- just check out my favorite videos and photos. Cum, Cum, and more cum. I'm a late bloomer as far as discovering my kinky side. After a long, dull marriage consisting of vanilla sex, I got divorced a few years back and decided to explore some fantasies. I love porn, and I've always been somewhat envious of the chicks in the xxx vids, they always seemed like they were having tons of fun getting their cunts, mouths and asses filled with hot cum. Multiple cum shots really turned me on. But I'd always identified as heterosexual -- so how could it b... Continue»
Posted by jizzlover123 4 years ago  |  Categories: Fetish, Group Sex, Shemales  |  
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paying to be used as a girl

i's been dressing up in girls clothes since i was 11. my mom's and my 2 elder s****rs suff. they'd caught me on several occassions when i was younger, but had thought it was a phase i'd grow out of. only now it turned me on too much to ever stop

Just recently i'd developed a new even more outrageous fantasy. now when i dressed i would fantasize about being used like a girl by a man....sometimes the fantasy would involve several men.this had come about ever since my mom had bought our first home computer. I'd spend hours when home alone watching tranny porn on the internet. i'd even posted p... Continue»
Posted by hornyTVluvr 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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mature crossdresser & 18 year old PART 2

After we sat on the couch a few minutes kissing he whispered in my ear he wanted try licking my boy pussy.I said yes an postion myself so he could, for a boy that never done anything sexual before he speard my cheecks and started to lick and kiss my hole.Then he buried his face and tongue deep in my hole as he did that I love and made finger me at the same time.After a good ten minutes of him eating me I told to lay down on the floor he had me so horny I wanted his cock in me.
He got on his back I put just a little lube on his hard cock he had my hole wet with his spit from eating didnt nee... Continue»
Posted by cdpaula 4 years ago  |  Categories: Gay Male, Mature, Shemales  |  
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The Slave and the Sissy Part Three

I was more frustrated than ever now; Ella laughed wickedly as I was led away on my leash, my cock pulsing and dribbling like mad in its cage, was there no end to this torture? We turned a corner and we were approached by a smiling harem girl who, giggling passed a sack to mistress. We stood by a door to another room. Mistress tickled my balls before handing me the sack.

“You have five minutes to complete a task for me; I want you to put all the black ones in the sack.” She smiled and lifted her chin dominantly as if to say ‘I mean it.’ I was puzzled as she opened the door but asked no q... Continue»
Posted by midsummerman 3 years ago  |  Categories: BDSM, First Time, Shemales  |  
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“Some first date, huh”

So I had just gotten this new job at a fast food/dine in kind of place for the summer trying to make some extra money before the fall semester started. And there was this boy named Danny that would come into the restaurant every so often. He was really cute and had nice lean looking body. He was pretty shy but I could tell he was in to me because quite frankly the food wasn’t that good and he would always stop by during my shift checking me out. So a few weeks past and he had yet to make a move. I was a little hesitant as well because I didn’t know how accepting he would be of my “situation”. ... Continue»
Posted by pleasurenfun 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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Made my hubby crossdress and get fucked by bbc!

Finally convinced me husband to stop watching me take big cocks and to put on a pair of heels and to get fucked while its my turn to watch him!

ive always loved being a cuckold wife, meeting new people, having fun wherever it happens to be at, it really improved our marriage, finally i took it to the next step.

i spend alot of time at nights checking out mostly pics on xhamster and few videos. ive always been turned on by crossdressers, cumshots, and a few others fetishes im into. this time i finally got to see a live crossdresser fucked, my cuckold husband!

so we arranged to meet a f... Continue»
Posted by discreet4rmlanc 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Adult Video Store #2

I got up and walked into the next room as she closed the door behind me.

I took a second to look around the room. First I noticed the desk she had been leaning against when she first appeared on the tv screen. Looking to my right, I saw a nice camera on a tripod. Behind it was another desk with more camera equipment and a computer with a large monitor. On the monitor, I could see the room I had just been in. The chair I had been sitting in was clearly visible in the center of the screen. I had a feeling, while I was in the other room, that she was able to see me somehow. Now I knew she had ... Continue»
Posted by naughty_bi_interest 6 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Koni & The Carpet Guys

Monday morning, my day off, and my wife just left for work. I just finished shaving my body and legs to a gay silky smoothness. Excitedly, I went to the closet in my den, pulled out my secret duffle bag and began to dress. Picking out red lacy thong panties, then the lazy red matching bra. The black fishnet stockings, which always made me so excited when I had them on; then the little black dress. I sat that neatly to the side and went upstairs to my wife's vanity cabinet. I sat and began to put on my makeup, concealer, eyeshadow, lipstick and blush, until I look so good I wanted to fuck mysel... Continue»
Posted by Konicum 10 months ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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