Shemales Porn Stories
Page 75

A Reluctant CD Meets the Gang

I was at the office and I guess I must have been a little quiet because I scared my coworker, David in the next cubicle to death, almost. Sometimes I take off my shoes and work in my socks and when I stood behind him and cleared my throat, I wasn't sure if he was going to hit me, shout, sit dumbfounded, or be incredulous about it.

He was looking at some rather hardcore porn where a few guys were makin' a girl airtight while she was tied up. I guess I was looking a little too interested myself. This gave him an opportunity to save face about what he was looking at.

"You like?" he said c... Continue»
Posted by LeslieStone 2 years ago  |  Categories: BDSM, Group Sex, Shemales  |  
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TRANSEVOLUTION


People think I'm complicated

I'm not complicated as much as I am free of discrimination and others opinion over the true identity of who I am. See regardless whether one agrees or not I am not male, nor am I female either. I exist in a truth that is outside sociological normality. Our society got stained with the residue from over thousands of years of misleading. ONE small faction of mankind tried and semi temporarily successfully created a definition that has tried to eliminate the true existence of ALL people. (temp because: it is statistically logical that over that time technology an... Continue»
Posted by TSKristy 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
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Daddy's Popper Challenge

Since I've been enjoying the users’ stories here so much I thought I'd share one.
I'm a pretty good looking guy, love girls and pussy, but I am a closet tranny chasers. I love hooking up with crossdressers and transgender. I dressed a little in high school and college; I left behind the clothes but not the lust for the femme bois.

Last week when work was tough I needed a five minute distraction to clear my head so I called up Craigslist and browsed the Casual Encounters T4M. This was around 2:00 in the afternoon, a very hit and miss time. The ad that peaked my interest was "Mature Crossd... Continue»
Posted by gypsy61 2 years ago  |  Categories: Mature, Shemales  |  
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Preparing for master

Having stripped naked in the small windowless change room provided for me I admired my smooth, slim figure in the full-length mirror as I adjusted my CB6000 cock cage that I had been wearing under my jeans during the long train and bus ride from home. I briefly played with the padlock locking me in chastity as I a nervous tremor ran through my body with the thought that only he had the key to unlock my cage. My painted fingernails and toenails and navel ring were my only adornments so far, the bright red nail polish a vivid contrast against my even, lightly tanned skin. I turned side on to the... Continue»
Posted by jojosissy 1 month ago  |  Categories: Shemales  |  
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Trip to The Nashville Gloryholes

When I lived in Nashville, I never did totally “trannie” up, but I would just go"gay boy" with some white short shorts, maybe hot pink panties that show thru, some mascara, a little base and blush, flip flops with hot pink toe nails. I would visit every glory hole (when they were still there ). My shaved legs were tanned from the summer, the girls and guys were checking my ass out. Got a grin from the token sales lady and headed back. (the first one was the 5th Ave Bookstore everyone has a hard time finding). Saw a hot black guy in a booth, peeked in and pretended to not know how to operate th... Continue»
Posted by CuteGuy2Use 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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show me her cock

I hadn't done much partying .I was a mum all too young and a good one .But now theyve fled the nest and I am catching up on lost freedoms .
I am a single women we got on great except 10 years ago I lost them forever.A car crash.It took years too feel anything like horny.Id try sometimes really hard
spending good money on pumps pills and penis props .I was showing flesh to debt collectors and all in aid of getting turned on.
The only thing tat worked was a growing facsination with a new girl in opposite appartment.Why I felt hardend nipples and aclitoral buzzing as I had to... Continue»
Posted by looberry-Cunt 2 years ago  |  Categories: First Time, Shemales  |  
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Changing desires

Sat night 06/06/15

I had tried to open myself up all Fri night with no luck. I had a good enema, it took fucking ages to get clean. I did some poppers used my smallest toy to open up for the bigger ones. To no avail. My hole would not co-operate with my & my fellas attentions. I had closed up & my fellas tonguing had little effect, which totally got me pissed off as he is so good at it. Normally this always work if i'm a little uptight (happens sometimes).I had worn my hole out I pouted & pouted. I was beginning to get very forlorn as I felt I had let my fella down. Lots of pouting & sad fa... Continue»
Posted by lolawylde 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  
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first time public

My First Time In Crowded Place As Cross Dresser

about 2 months ago, i got up the courage to go to a crowded public place dressed for the first time
i put a post on craigslist saying where i was going and what i was wearing
then i drove to shopping center parking lot and dressed up in the car, make up, red lip stick, red finger and toe nail polish, blond wig, ear rings, necklace, rings, watch bracelets, thigh high stocking and gatrer belt, black 5" heels, black mid thigh dress
i drove to a closer parking spot and took a breath, put on sunglasses, grabbed my purse and stepped out into publ... Continue»
Posted by cdamanda 4 years ago  |  Categories: First Time, Shemales, Voyeur  |  
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Deep sexual fantasy part 2

I Know it been since last year since wrote about my bring up, and in that time space I have done a lot more.

So remember i was saying that in part 2 I would talk about my fantasy....well to my luck it came through :).

On a cold winter Sunday, coming from a business meeting i made my way onto the Tram from Roosevelt island to Manhattan, trying to find my way to the A Train to get to 181st in Washington heights. Being new to New York i had a difficult time finding the A/C Train which i eventually found, which is at Columbus Circle.

Reaching to my friends house, lets call her Nancy (whic... Continue»
Posted by Caribbean_Freak20 3 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  
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The High Bidder Gets Chrissie

High Bidder Gets Chrissie

My BFF Kelly belongs to an Alternative Lifestyles Club and her being a member always seems to affect me.
Several times a year the club hosts what they refer to as a "Slave Auction". The rules behind the auction state that
certain members who are selected by random draw are required to bring a date or guest to the auction. The members'
guest/date for the affair must agree to become participants in the evenings "slave auction." Agreeing to participate in the
auction means that at the close of the evening the newly acquired "slaves" are the property of the pers... Continue»
Posted by chrissieCD 3 years ago  |  Categories: Anal, Fetish, Shemales  |  
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Sissy boy and ... a shave

It’s a Saturday night. I’ve been talking with this guy online for a while now trying to determine if he and I are the right fit…. and also work up the balls to meet up (…so my balls and much more can be worked over). We’d spoken about a whole bunch of things whilst chatting, his fetishes, mine, and what both of us would like to do to the other / have done to us. From this it all seemed pretty enticing so we teed up a night we were both free to dedicate to debauchery. Thankfully for me my instincts were accurate when we meet, the guy hadn’t hyped it up, or just completely lied about what he loo... Continue»
Posted by littlebum85 4 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Soft and Sensual Release...

The Night Out

As I checked into the hotel I was tired but feeling very successful, the day had gone well, so a little celebration was in order tonight. Being away from home was painful but there was scope for a little chance to let my hair down and the locals had invited me for a drink and perhaps dinner later.

I walked into the room, it was comfortable, I knew this hotel well, I had stayed here before. I put my overnight bag down and then proceeded to check the room. I took off my coat and hung it up in the cupboard. Unpacked my clothes and hung them. As it was getting dark outsid... Continue»
Posted by paddy57 2 years ago  |  Categories: Fetish, Masturbation, Shemales  |  
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Tania

Tania was different! She looked and smelt so feminine. I'd been with other tgirls in the past but she was just different.

We'd been emailing and swapping sexy pics for some months now but now the day had finally arrived when we were at last going to meet. We'd arranged to meet in a lay-by just of the A46 just past a little village called Upton Crosby. I'd spent the last couple of days in a state of constant turmoil! What to wear? What would we talk about? What would we do? Would she like me? There were so many questions going through my mind. I so much wanted it all to be just right.

The... Continue»
Posted by joannacd1 4 years ago  |  Categories: Anal, Masturbation, Shemales  |  
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moms friend 2 - dressup slut

so I had been visiting Linda for about 8 weeks. Every oportunity I got. My mom was none the wiser. I'd invented a girlfriend that I was seeing. Linda had backed up this story by telling mom that she had seen me with her.

little did she know I was visiting her best friend to dress up as a whore every chance i got.

Linda had had to lay down some ground rules. I had to dress in the outfit she had picked out for me as soon as I entered her house. She would watch me dress.

Linda insisted I wear suspenders and stockings. I was fine with this as i just loved the look of my cock, framed by la... Continue»
Posted by hornyTVluvr 2 years ago  |  Categories: Fetish, Group Sex, Shemales  |  
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My Fantasy Meet

So what is my fantasy...well I suppose that being on this site is a bit of a fantasy in a way as I’m basically a straight guy who has become more and more turned on with the idea of wearing lingerie...then discovering this site accelerated the process and has made me more and more curious to actually meet another dresser like myself...I’ve also had plenty of hot times masturbating on c2c on here too and in doing so have graduated from wearing panties to stockings and now lipgloss, wigs, slips, pearls and heels...so I think that I am so ready to take the final step and actually arrange a meet.
... Continue»
Posted by Michelle62tv 8 months ago  |  Categories: Shemales  |  
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Chatroom trick

I couldn’t believe I was doing this, as I stood by her front door I struggle to find breath on a surprisingly clear day. It had started some months ago, and internet chatroom, boy those things can be dangerous. I had spoke to Mary almost every night, soon chats turned to sex then to fantasies. The difference was she only lived in the next town so when she asked to meet I jumped at the idea, she was so sexy in her pictures. Admittedly Mary was 41 and I was 26, but still. She stood at 5ft10, long straight red hair, a body most twenty one year old girls would be jealous of. Stunning was the word.... Continue»
Posted by stig1963 4 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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The Origin of Sgt. Steel Part 2: Iraq, Internet Po

For a long time I skated around the periphery with my attraction to shemales and fembois. After my initial exposure watching Jaye Davidson in "The Crying Game," I went back to living with my soon to be future ex-wife and my two stepdaughters.
I didn't really start considering shemales and fembois until my second deployment. In August 2007 I arrived in Iraq. Although I have been in the military for over thirty years, I’ve never been one of those gung ho types. To be honest I’m more of a cynic. Kind of like a character named the Comedian in a movie called Watchmen. He looked at all the serious... Continue»
Posted by sgtsteel 10 months ago  |  Categories: Anal, First Time, Shemales  |  
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Away From the Campfire, Part Deux

I never for a second believed he was actually going to show up next Saturday. But, it hardly mattered. That quick, trashy blowjob I'd given at the camp had awakened something in me: lust. I'd long repressed my bisexual tendencies, and buried my femme side. And now they were awake.

When I got back home from the cabin, Sunday, I dug out my old friend, Dildo Daggins, and went to work on my ass. I came three times that night.

It was hard to concentrate, and to sit, at work Monday, but I managed. That evening, I got my boxes of girly clothes and supplies out of storage, and went through... Continue»
Posted by TransContinental 10 months ago  |  Categories: Gay Male, Shemales  |  
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First fuck for Freda

I'm such a slut. It's not easy to know where to start. I suppose my routine - that's what got me into this, I guess.

Each morning, after my mother went to work, I had three or four hours before my shift at the factory started. I would get the box from under my bed and dress myself. The stockings, the suspender belt, the bra, the patent heels.

I would brush down my long hair and apply my make up, slip into a short mini-dress and admire myself in the mirror. I loved turning from Fred to Freda in the mornings. I'd always put my panties on last, for some reason; I just liked it that way. My ... Continue»
Posted by laceonlegs 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Plug fun in the video store.

I have been known to keep it in for multiple times also. I had put it in for a week moved up a size and kept that up for a month then went to bush river videos. I was just sucking some guys when a big cock plopped out from an aggressive guy. I could not fit all of him in my mouth and had had cum all over my face I wiggled up off my knees and stood up to him and put my hand on his cock lead him to the bathroom.he did not want to go but I leaned back to him and said I cannot fit you in my mouth but I can in my bubble butt, that is if you are up for it. He pulsed in my hand and got bigger. I flin... Continue»
Posted by deveon4u 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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