Shemales Porn Stories
Page 60

The Lion, The Bitch, and the fucking Wardrobe.

I guess I have always been a sissy. I started crossdressing at a young age and it gave me such a wonderful feeling that I struggle to form the correct words to describe the way it makes me feel. It just felt right, and ohh so sexy! Like I said, I have always been sort of a sissy, and my father couldn't have been less plesed. I think he had his suspicions that I might be, uhhh... different before he found my lingerie and stilleto shoes, but once he knew for sure thats the first time he hit me. He made me promise, at pain of... pain, that I would never do any of "that faggot shit" again.
... Continue»
Posted by redk1 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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The first encounter

I remember my first relationship with another man. Sixteen, still in high school in a small town and ready to go to anywhere but where i was. John was 30 and a high school teacher. We met at a summer camp. A group of us became friends and would meet on week-ends to party and generally hang out.
The first time that John and I were alone came that first fall; following the end of summer camp with both of us back to school. John called me and asked if I wanted to get together with some friends. So he picked me up and off we went on a Saturday morning adventure. We started the party fairl... Continue»
Posted by christoboy30 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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A Night to Remember pt 2

I had no idea where we were going and I couldn't ask because of the gag, I started to get worried.

It seemed like hours till we stopped but I guessed it wasn't that long. Then Mistress finally spoke.

"Now I have a special treat for you" she said. "You have been doing so well sucking my strap on that I thought I'd put it to good use.

"I have driven us to a local dogging site for you to suck cock like a true whore.

"Don't worry about your safety, your wrists and ankles will be tied together so you can't escape. All of your zips and buckles are locked so nobody can do anything other t... Continue»
Posted by sissy_paige 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  
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Long Time Crush

When I was twelve I met a new classmate named Dave, he and I became great friends hanging out, joining clubs and what ever else high school k**s do. His f****y was from the Phillipines and he and his s****r were the first generation born in this country. His s****r Mai is the focus of this story. She is two years younger than Dave. I had a crush on her from the moment I saw her. She was one of those girls that even at a young age people would say how beautiful she was. Long black hair, deep brown eyes and that great skin tone she was just stunning.
But as she was only ten at the time I ... Continue»
Posted by triphammer73 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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my transformation... 101

I was at a very tender age of 10 years when my story begins. I was born male. With all physical parts in tact. But there was something deeper which was unfathomable. I was a very lovable sweet k** just entering fourth grade. I studied in an all boys school. On the out set I knew I was a bit different from the others. I had to much love and care than what a similar aged young boy would do. People thought I was to mature for my s****r age. Least did they know how I felt within. Let alone others I too didn't know how I felt until I grew up.

An incident changed my life at this tender age. I sh... Continue»
Posted by tran4mate 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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A day of dreams - Part 3

The cocktail party...or is that a "tail of cocks at a party!"

“You'll be find darling. Just breathe, relax and enjoy it. Cocktail parties belong to us...to women. Me control the mood, the events. The men are just pawns in the game. Sure they think it's all about them, but it's not. It's about us. You'll see. As a woman you control and manipulate the men. They follow your every mood and direction.”

Michelle was giving me reassuring directions. Me? I was nervous as hell. I didn't enjoy cocktail parties to start with. And now I was in unfamiliar territory. A woman for the first time in my l... Continue»
Posted by didi_galtier 1 year ago  |  Categories: First Time, Shemales  |  
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A day of dreams - Part 2

Continued from Part 1

“Hi Cheryl, here's our girl. She's all yours. Do your magic and turn our girl into the belle of the ball!” Penny was talking to a pretty young woman who was clearly waiting for us in the hair salon. “Hi there Didi, so pleased and excited to meet you! I've been looking forward to meeting you and getting to work on you. When I heard about you and about our brief to turn you into a gorgeous girl, I came and had a peek while you we're in the spa. But you were fast asl**p while your facial was getting done.” I blushed and softly and demurely greeted her.

“Ok Cheryl, I'll... Continue»
Posted by didi_galtier 1 year ago  |  Categories: First Time, Shemales  |  
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A day of dreams - Part 1

A day of dreams

I just couldn't believe where I was and what was happening. My emotions were a whirlwind of nervousness, confusion and yet also excitement. To say that I felt totally unsettled and out of my depth would be an understatement. I was way out of my normally controlled comfort zone and couldn't think straight. This was so foreign and yet I couldn't stop it and truth be told, I didn't want to stop it. This wasn't me.
It was as if I was a different person...a completely different person with a different personality, emotions and identity. Would this end? Would I suddenly feel nor... Continue»
Posted by didi_galtier 1 year ago  |  Categories: First Time, Group Sex, Shemales  |  
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Weekend retreat

When I go to work, I am in 'boy' mode. I certainly am not the most masculine person, and I am pretty certain that everyone knows my sexual preference. I often get mistaken for a woman even when in 'boy' mode. Whatever. I am who I am... deal with it :)

A few years ago my former workplace had a nice mountain retreat weekend. I love these retreats, not because I become closer to those I work with, but because they are so peaceful.

I arrived at the lodge on a Friday night and spent the next day communing with nature. My fellow workers were doing other activities, and I spent most of my t... Continue»
Posted by zaria_ts 1 year ago  |  Categories: Anal, Shemales  |  
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MY FIRST SEX WITH SHEMALE

This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous during a flight, so I needed a drink to calm my nerves. I sat at the bar and ordered my meal and drink. After a few drinks were gone, I noticed this stunningly beautiful lady enter the bar. She sat a few stools away from me at the bar, and I couldn't take my eyes off of her. She was a raving beauty, with... Continue»
Posted by fukkerguy 1 year ago  |  Categories: First Time, Shemales  |  
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My first man!

My first, and last in some ways!

Here's the story! Bear with me (That doesn't mean you hairy guys need to do anything but read!).

When I was 20 I was living in North Florida (a “few” years ago) and met an fantastic man, Joe or Joseph by birth, he was 49 and a Cardiologist at a nearby hospital (I didn't know that right away maybe a couple weeks).

Joe was amazing, German/Austrian heritage with grayed blonde hair and blue eyes, a tennis players body and a fantastic 9 inch uncut cock (as I would find out one Friday evening).

I met Joe in the typical fashion at a bar (The Hyde P... Continue»
Posted by Handj0b 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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A Night to Remember pt 1

I turned up at my mistresses house and as usual I immediately undressed and got on my knees on the ground by her feet.

Mistress immediately stood me up, locked me in chastity and put a butt plug up my ass. It was a little firmer than normal but nothing horrific.

She then immediately took me up to her bedroom where I could see a bed covered in latex clothing, which I knew I would have to wear. Although I'd dressed in latex for Mistress many times something felt different, Mistress spoke less and was a bit rougher too.

It started off with the latex thong to hide all my bits nicely, you ... Continue»
Posted by sissy_paige 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  
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Sienna loves Cactus

"SIENNA LOVES CACTUS"

My flat mate is Cactus. No! that is his name. I have asked him in the past for an explanation but to no avail. The more I push him the more cactus he becomes...prickly! He has a tough and tiring job and at the end of each day he returns home exhausted. After the evening meal he'd just say "I'm cactus, I'm going to bed. See you in the morning."

My baby s****r, Sienna, from the US is staying over on a brief holiday. It was the end of a busy working week and last night Sienna tried to get a spark out him. The more she tried the pricklier he got, eventually going to bed... Continue»
Posted by Cactus36 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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Sienna loves Cactus

"SIENNA LOVES CACTUS"

My flat mate is Cactus. No! that is his name. I have asked him in the past for an explanation but to no avail. The more I push him the more cactus he becomes...prickly! He has a tough and tiring job and at the end of each day he returns home exhausted. After the evening meal he'd just say "I'm cactus, I'm going to bed. See you in the morning."

My baby s****r, Sienna, from the US is staying over on a brief holiday. It was the end of a busy working week and last night Sienna tried to get a spark out him. The more she tried the pricklier he got, eventually going to bed... Continue»
Posted by Cactus36 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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LORI AND MICHELLE IN HOT TRANNY LUST

[image]NY LUST[/image]

"Let's go get some cock, Baby" said Michelle, all painted and dressed as an absolutely flaming drag queen; she flipped up her short miniskirt as she wiggled her naked ass. "Check my pussy, Honey". She bent over, legs spread wide thrusting out her ass, parting her cheeks with long red nails as she pulsed her pussy open and closed, her smooth balls glistening with her dripping pussy juice, her sissy cock dangling. Lori was at the mirror putting on even more lipstick and gloss. "Ummmm, I love it Baby, you are such a nasty bitch... Continue»
Posted by tvsllutmichelle 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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Fantasy Cums True part 4

This story is written by tittie-baby for xhamster.com

Fantasy cums true part 4

Terri is my shemale wife. And I guess the proper word now would be intersexed. When she was born she had a penis so everyone thought her parents had a boy and a girl. But as the k**s grew, Terri and Kate were virtually identical and Terri never showed any signs of wanting to be a boy. By the time the girls were 12 years old they both had a natural set of 34D breasts. Their parents took them in to the DR.'s for some testing. After the tests it was discovered that Terri had a gene that mutated and caused her cl... Continue»
Posted by tittie-baby 1 year ago  |  Categories: Shemales  |  
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Fantasy Cums True part 3

This story is written by tittie-baby for xhamster.com

Fantasy cums true #3

Terri is my shemale wife. And yes we are legally married. We have been married about a month now and have started to get our sex routine down a little. I have found out that as much as we love fucking each other that our tight little asses can't take getting fucked 5 or 6 times a day. So we have compromised a little, we fuck each others ass every morning and every night. The rest of the time we 69 until we cum in each others mouth. Then we do our cum swapping kisses.

Anyway as I was heading out the door to wo... Continue»
Posted by tittie-baby 1 year ago  |  Categories: Shemales  |  
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My First Time as a Girl

I was hoping to hook up with a straight guy.

I have 2 b*****rs and a s****r I’m the youngest and a Freshman in high school. Always been fem preferred to play with my s****r and her dolls. My dad is an ex-marine. Tough guy. My b*****rs are following in dad’s footsteps, military orientated. I‘m a big disappointment. My dad accepts me for what I am now. My mom always stands up for me when my dad criticizes me for acting like a girl.

My b*****rs look on me more as a s****r than a b*****r. Weird as it sounds I am more fem in a way than my s****r. I like to dress up in my s****r’s clothes and... Continue»
Posted by kbking70 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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Shemale massage

It has been one of those long and stressful weeks. I’m in desperate need of relaxation and relief so I head over to an Asian massage parlor for a typical happy ending massage.
The girl who usually massages me isn’t available so another girl is suggested which I accept. I think to myself that she can’t be much different than my usual so I don’t care much. I just need a massage badly.
She comes out of the back from another massage and introduces herself as Jessica. I smirk a bit knowing there is no way her name is Jessica but I go with the bit and am happy as she is quite attractive and alread... Continue»
Posted by malesub01 1 year ago  |  Categories: Shemales  |  
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The Fam...CH 1

Key Players;

Father - Dave

Mother - Brenda

Male sibling- Stevie

Female sibling - Alicia

Neighbor mother - Lakeysha "candy"

Neighbor twins - Keke & Tricia






"Fuck daddy...that was fucking hot" Stevie said while scooping up his f@+=€r's cum from the side of his face with his finger. Stevie was kneeling by the side of the bed with Dave's quickly deflating 9 inch black cock only inches from his face. Stevie is a young tw€|>e year old b•y that has recently been diagnosed with gender identity disorder. He is the youngest product of an interracial marriage between Da... Continue»
Posted by TS_LoverBoy 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
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