Shemales Porn Stories
Page 59

My Life as a Shemale Part8

It was on my way home when I decided not to tell Tim about Sin. This was very private and it was already bad enough that I knew, also, I had no idea what Tim might say or do. I did want to stay friends with her, now more than ever.
It was friday morning, the day after Sin was ****d and I was eager to get to school and talk to her, but she didn't show up, even after lunch I still could not find her. I asked our teacher if he knew but he just shook his head. I offered to take her homework and he gladly handed it to me, remarking that he was happy to see to become friends with Cynthia. I just sm... Continue»
Posted by gigi750 1 month ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 226  |  
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A big side effect (Sissy Story) by YKN4949 Part 2

Chapter 4: Not Alone Anymore

It only took me a few minutes to make it to the doctor's office. I parked and walked in but I already knew that the doctor wasn't there yet. Her car wasn't into the parking lot and neither was the nurse's. When I made it inside I saw that the only person there was the receptionist. She was a 90 year old woman who thought she was everyone's grandmother.

"Oh Mina!" she said smiling widely, "The doctor said you were going to be coming by today."

"Hi Mrs. Napier," I said.

"I'm sorry dear, the doctor isn't back yet. She told me she would be in by five," she... Continue»
Posted by sissyAlyna 1 month ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 2683  |  
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Wanting to go farther...

So now I had taken the final step... I had been fucked and dominated by a old man and loved it for some reason, which I would later discover after self-reflection. He had only made one little comment about the hair on my butt, but that was enough and I started to shave my butt and thighs. Just this act was and is in itself was exciting and sensual, whenever I shave my butt and thighs my heart starts to beat faster and I start breathing heavier. I look at my handy work in the mirror. I stare at my round smooth bottom and thighs. I wonder, "I bet he would like this." The act of shaving my butt a... Continue»
Posted by sissyboiforbully 1 month ago  |  Categories: BDSM, Gay Male, Shemales  |  Views: 2903  |  
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My Life as a Shemale Part9

It is now almost a year later and I am a year older, my hormone treatment has been going on for some time. The short version of the past few months seems some of the most poignant in my life but not conducive to this readership. My skin was getting softer, my body hair lighter and most important to me, I started to grow breasts. Sam was watching the whole process and thought that I would, some day, have nicer breasts than her. My oversized penis was still that but at this point I didn't mind. Cynthia, or Sin, lives with her mom in California now. The next night after I broke her Hymen she went... Continue»
Posted by gigi750 1 month ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 1385  |  
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The entertainment room ...

I looked around me and and i realised that the cellar did in fact consist of more than one room, each leading on from the one before it. I turned to the maid and asked how many rooms there were. Six in the cellar,was the reply, but of course there are many more rooms throughout Masters house plus the large gardens which contained i was told several outbuildings that i would if accepted find out about in due course. I asked if i was allowed to go and look at the the other rooms in the cellar and was told that that would not be possible without the Masters permission. I looked at Jane and asked ... Continue»
Posted by oldognewtrix 1 month ago  |  Categories: First Time, Shemales  |  Views: 1305  |  
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My Life as a Shemale Part10

Suzi and I started spending more time together as the weeks past by. I think she might have fallen in love with me but I knew little of these things. My focus was on my studies, I found that I excelled in school and it pleased me to do good. She had heard about me possibly liking sexual arousal through pain and made a plan for that. Tim was not happy but it was something I wanted to discover before I turned my back on it, even Sam had concerns but could see benefits in mental health coming from it, so she didn't complain too much. She might have thought that she would lose me as a friend as we... Continue»
Posted by gigi750 1 month ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 1013  |  
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LittleMissLipService offers Doug an Apology

Hi all....I have been so bad about posting stories here,
I actually enjoy writing when I have the time and have many, many great true stories that I want to share with all of you naughty perverts ;)

So watch this space for several new stories shortly.....
This is an entry that I wanted to share with you about something that happened earlier this evening when I offered to take a fellow Xhamster writer's fantasy and flesh it out into a story...... They had no interest in doing it and I and several other readers thought it started out very sexily and then just died off - we wanted our Happ... Continue»
Posted by LittleMissLipService 1 month ago  |  Categories: Hardcore, Sex Humor, Shemales  |  Views: 695  |  
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Life is full of little surprises (part 2)

(continued from part 1)

The door swung open, I saw a petite pretty woman looking quizzically at me. “This lady has had a nasty fall and it was my fault” - I could hardly believe what Scott was saying - “so Emily, can you please help her clean herself up and look at the nasty wound on her hand”. Emily smiled at me and replied “Yes Daddy”. She held her hand out, took mine, led me indoors and upstairs to a bedroom. “I'm a nurse” she said “now let me sort you out”. In twenty minutes or so I was clean and my grazed hand covered with a soothing cream. Emily let me repair my make-up and hel... Continue»
Posted by spankbuoy 1 month ago  |  Categories: Anal, Fetish, Shemales  |  Views: 430  |  
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Bondaged and fucked at a hospital: pt1

I was watching a baseball game with my cousin Jackie who was 15 and it was an unusually hot day for which I hadn't fully prepared for since I was young and head strong to say the least. It was half way through the game and I had run out of water but I didn't want to take my cousin's water or miss the game so I stayed in the intense heat without any water as Jackie continued to sip from her bottle of water. I didn't want to alarm her or miss the game but I was starting to feel dizzy. Sure enough, as I touched her shoulder to tell her I wasn't feeling so good I fainted and fell out of my seat la... Continue»
Posted by adblman 1 month ago  |  Categories: BDSM, First Time, Shemales  |  Views: 6485  |  
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The "Home Gurl"

An attempt to write a Cross Dresser/Trans story requested by a friend.

They called him "STONE". Steve Adams. High School athletic hero,Combat proven Military man, homeless and in jail. He had only one person who might help him since he had burned the help of f****y and most friends. He remembered a friend he turned his back once finding out he was gay, Cary Bishop. He called the only number he knew and got his old home. Cary had moved states away, but they said they would tell him. Four days later, Cary called the jail. They talked and Stone ate crow, desperately begged for help. Cary rele... Continue»
Posted by dickblackman 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 686  |  
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A surprise at a wedding

Me and my friend attended the wedding of one of his old mates and I was pretty much invited along just to keep him company, and it was beautiful, a big fancy wedding, delicious food, and lots, I repeat, lots of great looking women.

It seemed pointless me being there because it wasn't long before my friend hooked up with one of the bridesmaids and just left me alone at the bar, sipping on my drink, until low and behold, I caught a cute, petite woman staring at me with a smile on her face, I decided to make a move.

We got to chatting and I quickly realised that this girl had an amazing per... Continue»
Posted by wherethewhitewomenat 1 month ago  |  Categories: First Time, Shemales  |  Views: 46007  |  
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MY GAY PRISON SISSY ****


I'm sure many of you have seen a number of movies or television programs based on prison life behind bars. Having recently spent some 29 months in an undisclosed New England State Pen, I'll now share with you first hand, some of the wildest and most unbelievable sexual experiences one could ever imagine.

While still on parole now, I will change my name here and not mention the state facility involved. Other than to substitute a few names for some of the real ones involved, all of what I'm disclosing here actually happened between late July of 2007 and Dec. of 2009. My work... Continue»
Posted by cddixie 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5826  |  
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Last Weekend's Flake Becomes This Saturday�

This was the second date I'd arranged with this young gentleman. The first had, unhappily, fallen to pieces even before the evening of - and while I'm not usually given to providing flakes second chances, I was in enough of a charitable mood (and let's face it, I was definitely in need of some action) to arrange a meetup for Saturday.

When he arrived it was already dark out, and cold. I'd left my door unlocked for him,so the first I knew of his arrival was the tinkling of the chimes as he opened the door. I was waiting for him in the livingroom upstairs, dressed as he'd requested, all in ho... Continue»
Posted by sissymaidjanine 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1024  |  
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Times I almost got caught cross dressing

I might more appropriately have named this 'times I got caught'. One day, after MANY when I used to dress and walk my driveway, two of my neighbors actually caught me. One was my nextdoor neighbor. I used to be defiant of cars driving by....my driveway is 400 feet in the woods, so unless you were specifically looking up the driveway, you wouldn't have noticed me. Well, he did. He drove by, and I didn't notice that the car started driving so short a distance from me. He drove by and saw me, slammed on his brakes and backed up. I ran like hell into the woods and hid behind a tree. He yelled out,... Continue»
Posted by IAmDanCieri 1 month ago  |  Categories: Sex Humor, Shemales  |  Views: 2108  |  
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Clare


I shouldn't have tested her. Or, maybe I should have. I'm not sure anymore. I'm not sure which emotions are mine. I'm in a happy relationship. I think. My name is Clare. Now... Anyway. Sorry, I realize how confusing this is. Let me attempt to make sense out of it. My name is John. Or, my name used to be John. My best friend is named Hunter. We did everything together. Now we do everything to each other. You see, Clare was dating Hunter. I didn't know her last name, whether or not she had a f****y, or anything like that. The strange thing is, neither did Hunter. He assumed she was shy or emba... Continue»
Posted by klammer 1 month ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1790  |  
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Irresistible



Irresistible



My wedding day... I suppose all brides cry on the day of their wedding. But maybe not for the same reason my bride was crying...

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Becca and I had been engaged for nearly a year. Being that we both came from prominent families we had a huge wedding planned. All of New York society would be in attendance. Her father tried not to show it but he was incredibly perturbed at how much he had to shell out for this huge wedding.

"I don't know where this stupid tradition of the father paying for the wedding ca... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 3196  |  
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Thougt i could fool the staff

Realized this day would go on so decided to go buy lightbeers an two packs of ciggarettes..

Uppon arival i smoothly asked two female store attendants where i could find makeup.. yeah sure over here, they where holding back giggles i swear and as suave as james bond i just flat out lied someone is gonna look really pretty for his birthday! (u know im just getting supplies) then i asked them about what i thoght was foundation and they wher like yeah u use it to blabla and i said yeah just wanna make sure i got this note with me im not al so sure of what everything is...
So far so good..
... Continue»
Posted by tinyswede 1 month ago  |  Categories: Sex Humor, Shemales, Taboo  |  Views: 2115  |  
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Bi MMF, FemDom, Cross Dressing, Cuckold

I have these friends, a husband and wife. For the longest time, I've wanted badly to have sex with both of them. First I wanted just him, but I thought it would be even better if I involved both of them.

I'm bi, but they don't know that. Anyway, after years of hanging out with them, I see how domineering she is over her husband - my friend. She really puts him down, bitches at him constantly and belittles him, in front of anybody. She's really tough, but she's mostly been nice to me. She's got a couple of extra pounds and she's pretty and blonde. My friend is not very handsome, more "pretty... Continue»
Posted by chrissylegs 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 2277  |  
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Brandi Cums After MNF

This guy calls the e****t services and it seems like he is going to have the best sex in his life…

So, I come home from watching Monday Night Football with some guys at the local pub. I turn on the TV and some infomercial for an exercise machine comes on. The model working the machine has a great body and seeing her workout is really working me up. My cock even gets a bit hard.

Feeling a bit on the adventurous side, I open the phonebook and look for an e****t service that has shemales. I find one. Just talking to the dispatcher and describing what I want makes my cock hard again.

The ... Continue»
Posted by princessamyov 1 month ago  |  Categories: Anal, Fetish, Shemales  |  Views: 599  |  
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Shock and Awe Part 2

Have you ever been with a shemale before? This guy experienced what it’s like to be ass-fucked by a half-man, half-woman and it seems that he really enjoyed it…


Carla lay back on the white sheets and said ‘I want you to lick me down there first’

I was a bit shocked to be honest. I mean every guy imagines what it must be like to suck a cock at some point in their lives (and I just had for the first time, it was lovely), but anus licking had never entered my mind and I was hesitant.

Carla noticed my reticence and sat upright again. ‘Let me show you’ she said ‘ turn round and bend over... Continue»
Posted by princessamyov 1 month ago  |  Categories: Anal, Fetish, Shemales  |  Views: 681  |  
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