Shemales Porn Stories
Page 6

Crossdresser gets more than she bargained for

My story is like many I have read on here and which I only fantasised about, till now. This story is all true, I thought about embellishing it to make it sexier but thought I’d let you know what happened just as it did. A short history of me and dressing up first.
I have been crossdressing for as long as I can remember, from sneaking a pair of my s****rs panties, to even sneaking into the gardens of my parents neighbours and pinching underwear from washing lines. In my late teens when I found girls (and sex) I purged any clothing that I had and managed to put the ’urge’ behind me. I settled d... Continue»
Posted by CD_Danni 1 month ago  |  Categories: Fetish, First Time, Shemales  |  
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Becoming a Slut.

Over time, my mistress had trained me in her dungeon. Every time James entered I opened my mouth and began to suck.
I was chilling at home one day when there was knock at the door. I opened the door and found a UPS delivery driver on the step. He was holding a box which he thrust ito my hands, he turned and walked down the drive.
My phone chimed, announcing a text message.
'Meet me at the Regal Hotel in 20 minutes and bring the contents of the box'. I opened the box and found a suitcase inside. I attemptrd to open the case but It was locked.
I Looked at my watch and realised I was goi... Continue»
Posted by drews71 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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Béa was sexy femboy when she found a wild runaway boy. She decided to take care of him and raise him like her little b*****r. Together they discovered and revealed their feminine side and grew up into beautiful transvestites girls. Tthey soon became lovers, living perfect life together until zombies attack the city. Béa was transformed into zombie but Lilly changed her back by having sex with her. Then their neighbour Martin was saved. But people are killing zombies to defend themselves when they could be saved and cured with anal sex. Now the girls need to inform the news star announcer Jim J... Continue»
Posted by Baachan 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  
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Bianca Fucks A Mermaid (A Futanari Story)

Bianca sat on the beach, lounging in a folding chair and enjoying the shade of an umbrella. She owned a beach house right on the oceanfront, and had the whole section of beach all to herself. She wore a neon pink top that barely contained her rather large breasts, and a pink thong that did little to contain her futa cock. From the side of her bathing suit bottom, her thick, long girl cock d****d across her upper thigh and onto the beach chair, glistening lightly with sweat. Her pussy was just barely visible as the bathing suit bottom was pushed to the side to accommodate her anaconda of a cock... Continue»
Posted by BiancaBigTits 1 month ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
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My first time dressed as a girl Part 4 ( Spitroast

The next morning I awoke with a raging hardon, Gunther was already up and
wasn't in the room so I masturbated myself to a rather satisfying orgasm
using the visual in my mind from the past two days as inspiration. After I
cleaned up I found my panties at the foot of the bed and put them on and
then went into the closet. I fixed up my makeup and selected a Red wig that
was fashioned into a steeply angled bob. I found a thin Ivory cashmere
v-neck sweater-dress that was a decent fit and put that on after taking off
the corset which was becoming a bit uncomfortable. The cashmere felt
hea... Continue»
Posted by sbobbi66 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  
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The Reparations Act 56

The Reparations Act
by yutubeslut

A56 had a massive black cock up her asscunt as others
took turns pulling on her enormous and hypersensitive
nipples. The Master pounded away at her with a ferocity
that would have killed anyone else from centuries past.
A56 screamed in pain and pleasure, cumming over and over,
a small pool of semen collecting on the floor beneath her,
oozing from her tiny erect penis. Her little balls were equally
A56 loved it, of course. She was literally made for this purpose.
She now had no idea why she'd felt so scared this morning.

... Continue»
Posted by yutubeslut 1 month ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Avery's Temptations

My name is Jim. I love fucking white femboys and crossdressers with my black dick. I first saw porn when I was way too young, thanks to a step b*****r. I grew up watching girls scream and moan from hard anal. Soon anal was all I wanted to watch. When I was a teen, we got the internet. I first saw transsexual porn then. I loved to see their big tits and nipples, their made up faces and long hair, their asses and sexy legs, their high heels, and their big cocks. When I was young, I challenged myself to enjoy every type of porn there was. So I sought out every kind and jerked off to it.... Continue»
Posted by deflickrd 1 month ago  |  Categories: First Time, Shemales, Taboo  |  

Blind Date for a Sissy

Your alone in the motel room. You've spent all day preparing. You have removed all the hair from your body. Your skin is smooth as silk. The scented lotion you applied all over has your skin soft. You smell so sexy. You gave yourself several enemas. Your boi pussy is so clean. Your nails are manicured and painted bright red. Your makeup is perfect. Your lips glisten with the bright red lipstick. You pull the silky seamed black stockings up your legs. They make you feel so sexy. The waist cincher has given you such a feminine shape. Your tiny man clit is barely noticeable and is hidden easily ... Continue»
Posted by proudman2 2 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Meeting an Old Buddy After Becoming a Gurl

When I arrived at his house, he was waiting for me in the front yard. I was nice seeing Victor after all these years. His once huge afro is now gone, replaced with a glistening shaved head. His 6’6” frame is still in excellent shape plus a few pounds. Then I remembered how much I used to tease him because his was so dark, I called him “blue-black” but he looked good. Vic welcomed me in the house, and told me how embracing being a gurl suits me.

Victor complimented me on my dress, my new feminine figure and how I was “thick” in all the right places. After a couple of drinks, he leads me fu... Continue»
Posted by MatureBrownMan 2 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Help from IT pt 8

Chapter 8

Saturday was such an odd experience, Charlie couldn't remember the last time he slept so well, and when he woke he was full of ideas an inspiration. The morning flew by as he worked through designs, occasionally stopping to refine or adjust his work, but it felt like every idea he had was coming out fully finished. This kind of inspiration was amazing, he thought to himself during a short lunch break before jumping right back to his projects.

A few hours later his phone chirped. It was a message from Dani. A picture. His pulse quickened before he even opened it up and wh... Continue»
Posted by silklust 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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By CD_lishmis

Ever since I could remember I loved to fantasize about becoming a beautiful woman. I love their looks, their sensual movements, and the sexy lingerie and clothing they wear. I liked it so much, as I played with my s****rs paper dolls, I would put my face on their picture. I had to put makeup on so I would look more like a girl. I wanted the picture to look as realistic as possible; I loved looking at myself as a woman.. I pretended that was me with that beautiful body. Later on I started playing dress-up with my s****rs and their girlfriends. I was only ... Continue»
Posted by dlishmis 2 months ago  |  Categories: First Time, Shemales  |  

The Night I Lost My Anal Virginity

You may remember J from when I discovered I was the girl next door. The tall and handsome guy living next door to my apartment. Well, after Halloween night, and getting a taste for his perfect cock, I couldn't help but want more.

After Halloween I didn't see him much - I guess he was busy with school and work. I would go about my day trying to focus on things around the apartment, but every so often I'd have a moment where I would stop what I was doing and think about how horny I was from the whole experience. I decided I was going to get more of J, and that I needed to make it happen. So I... Continue»
Posted by revmyengine 2 months ago  |  Categories: Anal, First Time, Shemales  |  
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My Sexual Odyssey Part V: A Real Whore

A continuation of the journey described in part 4:

The next morning as I awoke, I realized that in just a few hours I was to re-experience the previous day’s activities. This seemed too much too soon, but I had agreed. Of course I could always cancel, but then if I did so I would wonder how much I’d miss it and whether I would have acclimated to the frequency and intensity. I decided to just forge ahead and so I got dressed and left for work, girly clothes under my street clothes and wig in hand.
I thought to myself, “This is ridiculous.” Still, I went ahead, determined to see it through. ... Continue»
Posted by LeicaCD 2 months ago  |  Categories: Gay Male, Shemales  |  
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My Son's Gurlfriend

My 22yr old son called and invited me to dinner to meet his girlfriend. She was a very cute young lady. I was sure she was a transexual right away. Not sure what gave her away but I could tell. I later asked him if she was and he admitted as such. I told him I was totally fine with her and not to be ashamed.

Several months later he told me they had broke up and I could tell he was heart broken and invited him out to my place for dinner. We set a date for the next evening. I starting preparing right away...I hoped he would approve of my plans.

I grew up making love with my parents as I h... Continue»
Posted by Barb51 2 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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A night out

like a
complete slut as my lips curled over his purple knob-
end and felt the cool night air on my twitching cock,
knowing that he could see everything I had as he looked
down and watched me.

"Christ, that feels fucking good." he rasped as he
looked down and saw my head bobbing back and forth,
"You suck just like a real woman."

"That’s because I feel like a real woman." I smiled as
I pulled off him and continued to slide my fist up and
down his rigid shaft, "And just like any other woman, I
love to be fucked by a gorgeous cock like this one...
So, d’you wanna try me? W... Continue»
Posted by dog9335 2 months ago  |  Categories: Shemales  |  
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Just One Day Of Your Life

Chapter One:

I had been moved out of my mother's house for two weeks now, and I still
couldn't believe it. I had made it! I was Dale Simmons, college man! No
more high school, no more curfew, no more cleaning my room or Saturday was like I was living in a dream world.

I looked out my apartment window over to campus. It was so big, so
exciting. I began to fantasize about all the football games I would
attend, all the parties I would throw, all the lovely women I would
date. God, the next four years would be ecstasy.

True, college life wouldn't be all fun and games... Continue»
Posted by lana100 2 months ago  |  Categories: First Time, Taboo, Shemales  |  

Vanessa and Rachel come to stay (revised)

Jess and I had been cleaning up the spare room, which had become a store for anything we couldn’t be bothered to put away like books, clothes, empty and full boxes, cleaned washing etcetera. The reason being, we had Jess’s good friends coming to stay from down south for a week. But we had been half way through tidying when we both got horny and ended up having some impromptu sex on the newly made bed making it sweaty and sticky with only a few hours before our guests were due to arrive. Laying there in that calm glow you get after sex, my arm around Jess with her head on my chest I suggested ... Continue»
Posted by Davey76 2 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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My new assistant - her story.

The year after high school I started taking estrogen. I had been wanting to transition to being a girl for as long as I can remember. After a year I started community college to become an administrative assistant. I turned 21 and graduated from the program on the same day. I was competing with numerous other girls for the top jobs in the job fair after graduation. Luck for me, I got the job I wanted, assistant to the CEO of a small company. Today is the first day on the job. I hope all goes well; I now dress as a woman full time and, due to my narrow shoulders and small features, I easily pa... Continue»
Posted by MassMan669 2 months ago  |  Categories: Fetish, First Time, Shemales  |  
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My Sexual Odyssey Part IV: From Slut to Whore

The next day as I went to work, I wondered what adventures lay before me. In a sense, it was up to me, in that I just had to put myself out there, not to mention put out. Still, the outcomes are unpredictable: I had no way of knowing ahead of time that a coffee date would turn into such a wild experience. When I arrived home I called Tom, and told him everything that happened the previous day. He seemed pleased for me, and encouraged me to continue with my adventures.
I resolved to call another of my admirers from the club, and see what would come of it. As I scanned the remaining scraps of p... Continue»
Posted by LeicaCD 2 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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I had given myself six full bag enema's to clean myself out completely I had shaved my body hairless and had gotten a mani-pedi...
I put scented lotion all over my body to make it smooth and soft then I dabbed some of my best perfume behind my ears and between my legs...
I put my sexiest nightgown on and waited for him to arrive...Do you think he noticed how amazing I looked or how much time I had put into getting this way I couldn't say as he just grabbed me kissed my lips so hard they felt bruised his rough working hands grabbed my tits and pinched my nipples hard I moaned loudly and when... Continue»
Posted by laceysgirl 2 months ago  |  Categories: Anal, Shemales  |  
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