Shemales Porn Stories
Page 67

BeCumming Barb

I began dressing to attract my dad. My mom was a beautiful and classy woman. Her style of dress was impeccable. She always wore pencil skirts or dresses of modest lenght, 4" heels, and always sheer fitted nylons and either a 6 or 8 strap waist cincher. Pantyhose had become quite popular by then but she did not wear them.

I had witnessed my parent making love many times. They had a "date" night once a week and mom would look her best. The date always ended with them making love. I would peek through the bedroom door and watch with envy as they kissed and held each other. It was always missi... Continue»
Posted by Barb51 3 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 1441  |  
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Sometimes, mistakes do happen but they can be real

A few weeks ago I was wandering round some of the nice tv/gay sites for this area of France when I got a message from a guy asking me if I would like to meet. Well, I was very horny at the time, so nothing new there, was aching to do something to somebody or have them do something to me, you know the feeling, when you ache to feel something nice and long in your mouth or being slipped in your pussy.

I thought to myself why ever not, he seemed like a nice guy, he wanted to meet on his way home from work so we arranged to meet in a quite well known gay rest area between his destination and t... Continue»
Posted by antoniaf 2 years ago  |  Categories: Masturbation, Mature, Shemales  |  Views: 1445  |  
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The Trip

I’d been seeing Joe for most of the summer and in that time I had starred in maybe a dozen or so of his private home movies. My hair had grown maybe another inch, I’d had my ears pierced and my eyebrows shaped, as far as my parents were aware it was because of a drama club I’d joined, where a part dictated the sacrifice, it was a poor excuse but they chose not to question it further.

One Sunday night I got a telephone call from Joe telling me to come over right away, I dropped everything and did as I was told. When I arrived at Joe’s he ushered me straight up to his bedroom.

“Were going ... Continue»
Posted by kara_zor_el 2 years ago  |  Categories: Shemales  |  Views: 1441  |  
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Jesse's Dream Job

Jesse sat nervously in the waiting room of the opulent office. He was there for a job interview as a personal assistant. Now at six foot tall with 220 lbs of football hardened muscle he did not fit the description of a personal assistant, but the advertisement on line had been pretty specific about the qualifications for the position and they were looking for a guy with his build. It was even listed first in the qualifications and typing was considered a ‘bonus’ ability. Go figure.

When he had arrived the receptionist called his potential employer on the phone and told him that Ms. Angel w... Continue»
Posted by SCARFACE12 3 years ago  |  Categories: Shemales  |  Views: 1439  |  
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Pounded to submission

Chapter 1

“Oh shit, fuck my black ass with that thick white cock you fucking tranny.” He moaned.

“Harder, **** my tight fucking ass baby.” He screamed

“Quit screaming like a bitch and take it like a man cock-whore.” She exclaimed.

He could feel a growing sensation of pleasure in his taint, a feeling of unnatural pleasure building up inside his loins that has never been experienced before. He felt as if he were about to cum but his hands were handcuffed to the bedpost and his female/male r****t was not touching his member.

“Stop! Something is not right, I feel like I'm about to ... Continue»
Posted by james_jones_03 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 1440  |  
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You've Got Shemale.

This is my first story of this type, so please, be gentle ;) It's a semi-true story, but definitely more fiction than fact, and it will be at least two parts.



I moved to a smaller town when I was in college and found that I didn't fit in at all. I actually got so lonely that I took up a friends advice and joined a dating site.

I had gone through a large number of messaging women on that site to find most remotely near me wanted nothing to do with me. My age range of early twenties had little selection and those that were in that range were surprisingly stuc... Continue»
Posted by MysticDude 3 years ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 1438  |  
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She became He

The day started as normal, wake up get dressed, have breakfast,but today was going to be anything but any normal day.

I decided that i would take the day off work and visit a local sex cinema,i had never been to one before and was a bit aprehensive but i thought sod it let's just do it.

Upon reaching the cinema i stopped as my heart started to race,after a minute or so i carried on in and paid my money and went inside.

I took my seat about 3 rows from the back there were a few people inside but not too busy,anyway after about 15 minutes of the film and with my cock starting to throb i... Continue»
Posted by carlosos 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1436  |  
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my first tranny pt. 2

it hurt so bad but felt so damn good. I told her just to stay still so I can get use to it. get use to having a cock in my ass. that was a totally new feeling. it was something I always wanted to try. now I was.

she slowly started to move back & forth. not really pulling out, just enough to make me feel better about it. she was stroking my cock, which was rock hard. I could feel her balls on my ass. deep down i was freaking out. this is really happening. I knew that coming here I was going to fuck some ass. not get my ass fucked.

eventually, I got use to her cock in my ass & she was pu... Continue»
Posted by radec_24 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1442  |  
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My Shemale Girlfriend 8: My Mistresses

Sorry i haven't been writing stories, I've been a full time slave of multiple mistresses the past year. if you read any of my other stories, you'd know my beautiful girlfriend/mistress Christy, who is my main mistress, Brittany, her friend from Denmark, is my secondary mistress and has moved in with us. My third mistress is Jennifer. Jennifer is usually only my mistress when one them are gone, but still often there. Often, all three of my mistresses are present to use me as they please. They own me, i am nothing but a toy used for their pleasure and entertainment. They dress me up in whatever ... Continue»
Posted by germanface 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 1435  |  
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Drama queen part three

Drama queen part 3

The next day (Friday) I got up and dressed in clean lingerie and a mini skirt with top, I did my make up, I was getting better; especially after the tips Alice had given me. I took my dirty lingerie and loaded it into my washing machine. I did notice there were no male underwear, and did a smile to myself. I checked the skirts, top and dress I had worn and decided that they needed a wash too so they were set aside for the next load. I remembered I had some essays from Drama school to mark. The rest of my day was spent reading and marking with the occasional break for natu... Continue»
Posted by hottvcarole 1 month ago  |  Categories: Group Sex, Sex Humor, Shemales  |  Views: 1432  |  
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The Making of a Gloryhole Gurl Part 3

Making of a Gloryhole Gurl! Part 3
By Kristy

I look back on some of the Pictures from my early days, going to the Adult Bookstores and the Park and can’t believe how bad badly I was at putting my makeup on and some of the things I wore. Although I still like to dress slutty!
I could sneak away for only so long before I had to change back and make it home without a trace. I made a major breakthrough soon and began going into the bookstores completely dressed and I was going more and more to the ABS’s and sucking as many cocks as their were, and if I got real lucky I would fi... Continue»
Posted by kristygurl 4 years ago  |  Categories: Shemales  |  Views: 1432  |  
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The best s****r ever part 6

Yes this is all true and please start reading from the first story please.

The next morning again me and my s****r were the early rises and had a fun idea for revealing the f****y secret to my girlfriend. First we went to our parents room to tell them that we were about to tell her this morning everything so we went downstairs to the kitchen and started to cook some toast.

Just before all the toast had been made, my girlfriend came down and walked over to us. She came over to me and when she went aroud the counter she saw all of us had no bottom cloths on and all had hard cocks and she j... Continue»
Posted by horndogs 3 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 1431  |  
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Halloween Disguise: pre-story by DanaWu

an original story by me. its not true more of a fantasy...

this story starts october 14th. first of all i am a 23 year old boy, i just moved to a different state to go to college, i dont have many friends and have only been her a couple of months.

today was like any other day, had to wake up early and go to work for a couple hours before school. julia, one of the first people i met here, approached me today and told me about an "awesome" party tons of the students have every halloween. she tells me about the last years party and some of the crazy things people dressed up as. she mentions... Continue»
Posted by DanaWu 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1430  |  
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Girlfriend's Hairdresser

“Look, honey,” proclaimed Kamron as he held a mirror in front of his client.
“I like it,” she declared with a smile. “How much,” she asked.
“Fifty-five,” the five-foot-nine-inch big booty effeminate hairdresser replied.
“Alright,” she said digging through her purse. “Oh damn. I left my billfold in my other purse. Do you mind if I get Tavares to drop it off when he gets off work,” she inquired referring to her live-in boyfriend that worked at the auto parts factory in town.
“Yeah, chile. That’s fine. What time does he get off?”
“Seven.”

“That oughta be fine. Just text me when he’s on th... Continue»
Posted by faggyboi 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1430  |  
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Gift of a blowjob

Some years back when I was younger and occasionally crossdressed, I was staying in a motel out of state. My room was on the second floor and had a full floor to ceiling window overlooking the parking lot. I was dolled up very sexy, and drinking wine. It was early evening but already dark. I noticed a man walking around the next building several times, and as he'd come around his walk placed him walking straight towards me. I think he was just walking for exercise. I thought he might be a good candidate for me to tease a bit, so I watched until he came around again and stood in the window with... Continue»
Posted by dana213 2 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1426  |  
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He Got Used and Didn't Mind (Part Three)

Great responces so once again 10 comments or 1,000 views gets part 4. I hope the categories are listed correct this time. Part 4 may be the last to this series unless I get fed some ideas after it. If you like the series please comment.

The next morning Dave woke up at Lucy and Carla's feet at the foot of the bed. He went to wake them and they each smacked an ass cheek. "Dave come take a shower with me." Carla beckoned as she nibbled his ear. Lucy nodded in approval and off they went. Once in the shower, Dave started to wash Carla's soft, chocolate body from head to toe with a gentle massag... Continue»
Posted by mrman1982 1 year ago  |  Categories: Voyeur, Shemales  |  Views: 1426  |  
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transvestite in trouble

i pulled up on the pub's carpark. I was nervous, i'd been speaking with Andrew for about 2 months online and for 2 weeks on the phone, we'd always end up jerking off when we spoke. it was during these chats that i'd told him of my fantasy. The one where i'm overpowered and f***ed.

I was dressed as instructed, black lingerie, suspenders and black stockings, tight high wasted skirt, just above the knee, white blouse and black jacket, i had on 4" heels, Andrew liked the secretary look. there were only 3 cars on the carpark, Andrew had said this pub would be quiet at this time on a Thursday, it... Continue»
Posted by hornyTVluvr 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1423  |  
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Bad Habits CD Fantasy

Why did I keep making bets like that, was the only thing I could think of while in line. Why did I keep making bets I was destined to loose, and then have outcomes like...well, this. I was standing in line to go to a cosplay convention, and was in full costume, but of the wrong gender. I was dressed up as one of those Vocaloids, with knee length blue pigtails, A black skirt that was barely at my knees, a set of black and blue boots that went up to my thighs, a sleeveless vest like shirt, a weird belt thing, weird glove-like sleeves (that left my armpits and upper arms open for the whole world ... Continue»
Posted by RosalynLee3 9 months ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1423  |  
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A true story: me and a transvestite man - part 2

OK this is the second part of my true story. I was going to leave it at two parts, but I think there's enough to make it three parts, now!

I think I'd best point out that beyond the (I'm told) common early sexual experiences most straight men have as youngsters, with other men of their age, I'd not had any experience of men. You won't, of course, get many straight men who admit to this. But I'm not like most men.

However, this early experience was enough to leave me curious as to what it would be like to have fun with a cock. As you may have read in part one of this story, I was rapi... Continue»
Posted by LookingForSomething 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1422  |  
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Swimsuit summer 2010

This really happened and even now I got both excited and scared thinkig about it.
Near me there is a bay that's very quiet, even in the height of summer its rarely visited, and I took to driving there in my car and sunabathing in just my swimsuit and hairpiece...seeing as many females of my age ar'nt stunning beauties and rarely wear make up whilst sunbathing I knew I'd pass at a distance .
On the first occasion, a man came quite close and said 'hi' as he passed and I just raised my head and nodded as I lay on my tummy. A couple passing by also gave me a wave and I waved back , apart from th... Continue»
Posted by holaryhilary 3 years ago  |  Categories: Shemales  |  Views: 1421  |  
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