Shemales Porn Stories
Page 61

First time dressed as a woman

Ok, this is an absolutely true story.

I'm a married white guy, stocky, 6'1" with a 5-1/2" cut dick. I've been dressing up on and off since I was a p*****n, starting with my mother's lingerie and dresses. I love makeup, but especially lipstick. I used to masturbate by stroking my cock with a bl**d red lipstick while reading those old trashy porn novels you could pick up in the seedier luncheonettes.

I always denied my cock loving side, imagining myself as a lesbian for the most part, but I fantasized a lot about sucking cock and getting fucked. Once I'd cum I'd feel ashamed and try to... Continue»
Posted by kevinj631 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  
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My Sissy Fantasy

My wife has been dating around for years. She loves the feel of different cocks and I enjoy watching her with other men.
Recently, she decided it would be fun to put me in a chastity. She said it was only temporary and if I didn't like it, she'd take it off. After a couple of days, I decided, I'd had enough. She didn't. She said she liked having me locked up and know I couldn't get hard or jerk off. "I'll let you know when you can cum again." She wore the key around he neck like a trophy. Her boyfriends would come over and she would have sex with them in front of me, only I wasn't able to je... Continue»
Posted by ForcedSissyGurl 1 year ago  |  Categories: Shemales  |  
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Feminization Fantasy

My wife has been dating around for years. She loves the feel of different cocks and I enjoy watching her with other men.
Recently, she decided it would be fun to put me in a chastity. She said it was only temporary and if I didn't like it, she'd take it off. After a couple of days, I decided, I'd had enough. She didn't. She said she liked having me locked up and know I couldn't get hard or jerk off. "I'll let you know when you can cum again." She wore the key around he neck like a trophy. Her boyfriends would come over and she would have sex with them in front of me, only I wasn't able to je... Continue»
Posted by ForcedSissyGurl 1 year ago  |  Categories: Shemales  |  
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The neighborhood sex slaves Part 3

I looked at Kelly and then back to Jack and Mary and said, "what's up"?

Mary laughed and then said, "well it looks like you're up and I know that Jack here is. How would like another BJ from him"?

As Mary said this, Jack moved down to his knees on one of the cushions he removed from one of the other chairs. Kelly looked at me, gave me a light kiss on the lips and said "have fun" as she pushed herself up off of my chest and slowly removed her cock from my ass. Her cum was starting to leak from me when I felt Jack's lips and tongue down there licking and sucking up Kelly's cum.

Kelly an... Continue»
Posted by Bigrodtaz 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
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An On-line Sissy Lives Her Dream

(Dedicated to a hot little sissy here on xhamster, Sluttish, whose looks and fantasies inspired this story. Her fantasy name is April. That’s where this story starts.)

It started innocuously enough with what seemed like a harmless exchange of private messages on a friends-based porn site. A person identifying as a male sent a note to a young sissy whose profile expressed some fantasies about being made into a full-time sissy, perhaps involving some f***ed feminization and even surgical “enhancements.” The young sissy, April, responded openly and eagerly, and the conversation developed into ... Continue»
Posted by scatpetsmaster 1 year ago  |  Categories: Anal, BDSM, Shemales  |  
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Poker Night Part 5

I woke up later that night for dinner. "Aww how was your nap" Mistress asked. I yawned and said it was good. She tells me that because I slept past dinner, I wouldn't have any, but she did give me a bottle filled with formula and some 'extra protein' which to me was more than enough! Later she promised she would take me out for ice cream since there was a little shop near by. She sat next to me on the couch and turned on the tv. This was quite the unusual event for me since I was rarely allowed to watch tv and spent most of the day locked up in my room. "Enjoying yourself" Mistress asked. "Yes... Continue»
Posted by ConvertedGirl914 1 year ago  |  Categories: Gay Male, Shemales  |  
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Caught wanking in school

This was my first sexual experience as a shemale, I was still in school, I loved the girls in the school uniform, tight white shirts so thin it would show their bras through and tiny short skirts, some flared and some really tight too, I would always end up getting a cheeky view up some of their skirts and I couldn't help but stare as their tight bald pussies or their tight perfect little asses. I had to wear that uniform too and I always had to wear little panties to hide my big cock.

We had just finished a P.E (Physical Education) lesson and we had all come back to the changing rooms, as ... Continue»
Posted by shemalecharlotte 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
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Russian Shemales 4: This Time, It's Personal

Again, I am not understanding humor in the title. My translator says "go with it". Whatever.

Mr. Aronoff calls in the morning, and says to meet him at the factory. We will be building set again for Friday night photography session. He is pleased with us, and says after taking out what we owe him, there is still little money we earned from last night. But he also suggests we buy some of our own clothing and cosmetics. This seems fair to us, as we cannot wear costumes when not working, and our country boy clothing is shabby. He will have Ana take us shopping later in day.

He also sa... Continue»
Posted by TransContinental 1 year ago  |  Categories: Sex Humor, Shemales  |  
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A First Time Out

I'd always fantasized about going out to a bar or a club, dressed as a woman, and after a few drinks managed to find the courage to do so. By the end of the bottle of wine I was dressed up and ready to go, suspenders, stockings, a corset on so tight it was hard to breathe underneath a loose, knee length skirt and close fitting top. My make up was done, a touch up of lipstick after the long black wig had been smoothed down and the last of the wine polished off.

I'm always told I look gorgeous when I dress up, but I'd never been out before. Before it had just been for other people in private,... Continue»
Posted by amylee-jones 1 year ago  |  Categories: First Time, Shemales  |  
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A Flatmate's First Time

My name is John and it all started for me the same as most CDs; I was 13 and had stumbled upon my mother's underwear draw and for some reason I decided to try on my mum's pantyhose. The feeling was divine and I was immediately hooked. Over the next few days I experimented more and more with panties, bras, shoes, clothes and make-up. Ever since then I have had several unsuccessful attempts to quit my habits. I am now a 24 year old closet CD who lives in London with my flatmate Katy. She did not know about my dressing until that one wonderful afternoon.

It was a Friday afternoon and as of the... Continue»
Posted by amylee-jones 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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A Night Out



I was at the bar one Friday night after a long, long week at work. It was one of these weeks where at the end you tell yourself you need a drink. I was still new to this town and haven't been out that much so I went to a bar near where I live in case I decided to drink myself into a stupor. I got there about 7 and went right up to the bar to order my drink.

Once I got my drink I took the bar in. It was more of a club then a bar, the type that late at night would be filled with d***ken idiots dancing and grinding on the dance floor. The place was only a third full but surprisingly ther... Continue»
Posted by amylee-jones 1 year ago  |  Categories: Hardcore, Shemales  |  
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A Black Tranny Fantasy

It was only when she emerged from the bedroom in a purple silk nightie that not only clung to her full breasts, but also betrayed the hint of a bulge between her legs, that I realised that it was actually going to happen: my fantasy of sl**ping with a black shemale was about to come true. She paused at the bedroom door and smiled at me.

'You like what you see?'

I did indeed, but my mouth was too dry for me to say anything, so I just smiled back and nodded. Sasha looked as good as in the picture I'd seen online on the e****t site. Chocolate brown skin, soft, generous lips, a cute smile, b... Continue»
Posted by amylee-jones 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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A Drive in the Country

It had been a rare hot dry day and the evening promised to be hot as well. Toni the lovely CD I have met down here in Wales arrived as arranged just before dusk in his car to collect me and take me somewhere secluded he had found for some outdoor fun.

We drove about a mile before Toni pulled over and quickly removed his trousers before getting back in and driving off to the secluded place for us to play. I was pleased to see as she (Toni) slid back into the driving seat that she had on a slightly flared mini and black stockings, the top of one was just showing and was wetting my appetite.
... Continue»
Posted by amylee-jones 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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LittleMissLipService gets more than she bargained

LittleMissLipService Gets More Than She Bargained For...

So I was having a conversation with a friend on here and we started talking about how sexy our painted toenails and feet made us feel - I started to tell her about one adventure of mine.
This friend insisted she wanted to hear the rest and so I ended up having to take my time and type it up because i hadn't really shared all the details with anyone before - and it was very sexy - and I wanted to be able to remember everything years from now for my enjoyment.....
It ended up being way longer than I expected - but it was well ... Continue»
Posted by LittleMissLipService 1 year ago  |  Categories: Fetish, Group Sex, Shemales  |  
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Russian Shemales 3: The Revenge

I am asking the translator what that means: The Revenge. There is no revenge in my story! And she says it is a kind of joke. Like the Electric Boogaloo. I do not understand why that is funny, but she is telling me to trust her, and continue with my story.

When we grew awake in the morning, Svetlana wanted more sexy sexy time, but I said to not. Because Mr. Aronoff would be there soon to pick us up for the bus ride back to home. Svetlana, who looked more like Serge in the morning, said quietly, he did not want to go back home. I pushed him into the shower to wash off the cosmetics fro... Continue»
Posted by TransContinental 1 year ago  |  Categories: Gay Male, Sex Humor, Shemales  |  
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Not Your Average e****t pt2

“That was pretty good grilled cheese,” Holly said from her seat on my couch. She lifted a glass of sweet tea and took a sip. “Good tea, too.”
“Thanks,” I called out from the kitchen. I placed out plates in the sink and walked back over to the couch and sat down beside Holly. “What would you like to do next?”
“I dunno, we could just hang out a bit or we could go back to the bedroom...”
“Movie?”
“Sure.”
I walked over to my DVD rack and started going through my collection. We settled on one of my favorites and I popped it into the DVD player, grabbed the remote and moved back to the cou... Continue»
Posted by TheHumanoidTyphoon 1 year ago  |  Categories: Shemales  |  
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Russian Shemales 2: Electric Boogaloo

The next Friday, Serge and I take bus into the city again. He was very anxious to be there and to get pretty again. I am just anxious.

Friday night is much like the previous Friday night. We move furniture, and build set, and then smoke cigarettes and drink vodka. Saturday is again the same: We are showered, and painted into pretty ladies. We take turns posing for camera in bras and panties and slips and stockings and high heels. We are both getting better at walking in heels. (If you search "Russian Shemales" in photo gallery of XHamster, you may see some of our photographs.)

But... Continue»
Posted by TransContinental 1 year ago  |  Categories: First Time, Shemales  |  
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Mommy Has A Cock

I want to sing to the world about my beautiful wife
Perry. Fuck anyone who questions true love between men.
A wife with a cock is better than one with a cunt any
day. Perry is so sensitive and worships my cum filled
cock with his cock sucking mouth and his tight brown
ass hole.

He is so beautiful dressed in his short red party
dress, black thigh stockings, leather high heels and
make up. His hair is shoulder length and he is prettier
than most women. I demand that his soft body is shaved.
I am demanding and he loves me for taking charge.

The only thing needed to compl... Continue»
Posted by 1superhornyguy 1 year ago  |  Categories: Group Sex, Mature, Shemales  |  
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T-Girl Obsessed

You now know that I have a
thing for T-Girls. Ever since I experienced that first
mouthful of cock on a female Amazon body, I can't get
enough. I don't consider myself queer or even bi-
curious. The thought of all out sex with a man doesn't
interest me at all. I have had my cock sucked at the
local porn shop, but I never gave back.

Anyway back to the main story. My first encounter with
a shemale got me hooked. My next chance was about sex
months latter. The rest of the f****y went out of town,
so I was home alone for the weekend. I called my
shemale heart throb for an app... Continue»
Posted by 1superhornyguy 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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Joe, Chrissie and, Paula

) I don’t know why I need to get all dressed up, it’s you he’s coming to see.
I know, but I like to see you looking sexy and I’m sure Joe appreciates having a sexy woman watching.
Anyway, you finish off and I’ll make sure dinner is OK.
It would be the second time Paula had met Joe, the first time she was only there to take photos, not taking any part in proceedings.

How does that look Paula?
Yes, you look good, very tarty though, I can see your stocking tops
I know, but he likes me like this. Oh,Oh, that’s him now. Will you go?

Paula lets Joe in, greets him with a kiss and when he ... Continue»
Posted by chrissie28 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
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