Shemales Porn Stories
Page 114

Ally...


I was at a customers' house doing some yard work as they had paid me
in advance for just minor clean up, pulling weeds, mowing, trimming the
hedges. I was finishing trimming the hedges in between the neighbors and
their house and as I finished up the neighbors' wife came out or so
I thought.

She politely smiled and waved to me and I nodded trying hard to act as
if I was not noticing her in a skintight bikini with a lacey French cut
bottoms. She could tell and began to tease me by dropping her towel and
turning her back to me showing her pear shaped bottom with the long legs
leadin... Continue»
Posted by NaughtyNshy 4 years ago  |  Categories: Gay Male, Shemales  |  
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First Times a Charm... My 1st love.

It was late August 2002. I was 21, and looking for a room to rent getting out of Baltimore to broaden my horizons. I wanted to start fresh with maybe some new friends, and seek new ambitions. My folks had split up, after a nasty divorce, so I had to get my head clear. I was an only c***d, and was very close to them except now I seemed to be estranged to the both of them. So, after picking up the Sun paper, I browsed the "shared housing" section. I called, and talked to a few people. Some for one reason or another didn't really fit my fancy. One woman I talked to had a whole laundry lis... Continue»
Posted by gurlinpumps 1 year ago  |  Categories: First Time, Mature, Shemales  |  
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Busted

I know you're married and you have k**s and stuff, but sometimes I wish you didn't so that you and I could be together." I was speechless and unable to respond. "Do you ever think about me that way? I mean, what it would be like to be with me?"

"Yes," I finally admitted. "I do sometimes."

Jenny closed her eyes and lifted her face closer to mine. I knew I should push her away, tell her no, take her home and forget all of this had ever happened. But feeling this nubile teenager so close to me, knowing how badly she wanted me, I was powerless to do anything except close my eyes and lower my... Continue»
Posted by koolstuff 3 years ago  |  Categories: First Time, Hardcore, Shemales  |  
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Amy The Tranny Chapter 2

I couldn't stop checking Amy out all through dinner. She was dressed in a skin tight mini skirt, her perky little tits standing out from her tiny frame, and long hairless legs cast in nylon fishnet stockings, and 6" stilettoe heels. I wasn't the only one gawking at her! Every guy and even some girls were checking her out as well. I was surprised a little when she excused herself and went to the restroom, and walked into the ladies! I mean, it did make sense, but my sore ass made me think she should do into the mens! Anyways, after a nice meal and some small talk, we headed back to my place fo... Continue»
Posted by panteeluvr 4 years ago  |  Categories: Fetish, 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 6 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Used by Taxi Driver and more ch.2

The taxi driver headed off down the road towards the town again but on the way there walking along the road was 2 young girls and the driver pulled up beside them and asked if they wanted a lift?
They both smiled and said yes that would be great...town centre please. As they got into the back of the cab they were stunned to find David tucked up in the far corner.
They looked at the driver and then carried on getting into the cab. As they all headed into town the girls asked why he was there and why he was dressed as a girl and again the driver told them what he had done and the girls had a s... Continue»
Posted by Acebottom 5 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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A Day at the Beach

A Day at the Beach
By Lorenqt

I lay face down on my towel, basking in the sun, almost falling asl**p. My boyfriend Jake, he would be my husband if it were legal where we live, walked up and sat next to me. He gently stroked my left arm, "The water is great, Loren. You should try it."

Without opening my eyes, I turned my head towards him, "I think I'd rather just lay here in the sun."

He started rubbing my shoulder a little harder, "Come on, sl**py head. Get up."

"Stop it Jake!"

He gave me a quick kiss on the cheek then he whispered in to my ear, "Or, would you like me to ma... Continue»
Posted by lorenqt 2 years ago  |  Categories: Anal, Shemales  |  
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My new ladyboy- LittleLi - Part 1

It was nice to meet my new freind littleLi. I met her at the library at college one day and was immedietly attracted to her. Her long dark hair and big brown eyes, with a lovely sweet smile. She was wairing a little cropped T shirt with a hello kitty picture on it, showing off her smooth honey coloured tummy, cut off denim shorts, white frilly ankle socks and black patent pumps. I thought to myself, only an asian girl could wair little frilly laced ankle socks and mary janes and get away with it! I had known for ages i was bi, so i was not suprised that this fanatastic girl standing in fron of... Continue»
Posted by igglepiggle 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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caught spying

i would love to re act this with someone ;) any offers?


A young man, 18, is caught spying on his girlfriends mother in her bedroom, and is taught a hard lesson. Characters: Tim, 18, Student; Susan, Tim's Girlfriend; and Julie, 44, Susan's Mother ;-).

Julie sat at her dressing table, preparing for bed; she brushed her long dark, which was one of the pride and joys. Normally, this would help her relax and unwind, but tonight, and on several other nights, she found that remained tense. She couldn't get over the feeling that somebody was watching her, for several days, perhaps a week; when... Continue»
Posted by leadpencil21 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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Employee Discount

“Tariq, you need to go get a suit for Uncle Mack’s funeral,” Jackie Woods instructed her twenty-four year old son.
“Okay, ma,” grunted the fast food worker who was on his day off playing Call of Duty: Advanced Warfare.
“I’m serious. Do it today. You can use JC Penney card.”
“Yes, ma’am.”
“Tariq! Have that suit before we leave for Cleveland tonight.”
“Okay,” the six-foot-one-inch slim dark-skinned guy huffed as he paused his game. “I’ma get ready and go now.”
“Thank you,” the exasperated woman sighed. “I’m gone to the beauty shop. See you later.”

Tariq rushed out of the bedroom he’d ha... Continue»
Posted by faggyboi 1 year ago  |  Categories: Gay Male, Shemales  |  
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My ts fuck

Patong beach thailand a few years ago, a few drinhs at a bar with some friends on going to toilet at public loo which was next door to ladyboy bar. Standing and relieving myself in runs two lovely ladyboys from next door. Who proceed to do there make up and have a good look at my cock for good measure! Now at this point I hadn't any feelings one way or another, but now I was very curious indeed!
So I made my way back to my friends at the bar finished my drink and with a lame excuse left in the direction of the ladyboy bar, feeling nervous as hell I entered. It was dark with loud music a... Continue»
Posted by kawa696969 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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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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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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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 4 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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My shemale boss part 3

I was woken by the vibrating noise of my mobile and looked over at the time, the bedside clock said 1am. The caller I'D on the phone simply showed Bitch, naimly my boss Miss Jones, would she never leave me alone.

I answered the phone and still being half asl**p simply said 'yes'.
'Don't answer me with that tone Rob' she said. 'Sorry, but its one in the morning' I replied.
'Be a darling Rob and pick me up from the club, text me when your outside'. Before I could say anything she hung up.

I pulled my arse out of bed, slipped on some tracky bottoms and a t-shirt, jumped in the car and dr... Continue»
Posted by big_rob49 3 years ago  |  Categories: Shemales  |  
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