Shemales Porn Stories
Page 65

The GloryHole [true story]

one evening,I was feeling realy horny,so I got dressed to go to the local adult x store.wearing nothing than a strapless black lace corset,no panties,short mini skirt,and a pair of thigh high boots.and went with a short blonde wig.well walking thru the door,I turn to the left wear the door stood to the rooms,I could tell it was crowded,and there were alot of guys either standing around,or walking.well I found myself a cubicle,and went inside,slip a few bucks in to turn on video.a few seconds later I had a big cock sliding thru the hole as I reach down to pull it in my mouth licking it,and st... Continue»
Posted by blonde68 3 years ago  |  Categories: Shemales  |  
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a*****ed and Turned Out Ch. 1

a*****ed and Turned Out Ch. About four years ago, I decided to go out for the evening to a local club that tgurls hung out at. I was a regular there, and had been going there for some time with a regular circle of TG/CD girlfriends that I hang out with.

I was already excited when I started to prepare myself in the late afternoon. I picked out one of my favorite outfits, a short suede short skirt that came down just above mid thigh with a matching vest. I also picked out a tight long sleeve light pink stretch top and some calf high black suede boots with 2 inch heels. I am quite tall, and 3... Continue»
Posted by MacDaddy714 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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From manager to sub sissy

Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved to have an ongoing affair with Her. I know that I am not near man enough for Her and I have always know that from the first time I saw Her. Eventually after being friends for many years, I confessed to Her my desire to serve a Dominant Woman. She attempted being my Dominatrix, but could never g... Continue»
Posted by wannabesubformt 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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1st time-GAY BATH TS's and Black men

I was in Columbus on business a few years ago and happened to see an ad for a place called CLUB BATHE at a gay bar I was in. It was near closing time at the bar which was loaded with Transsexuals (mostly black) due to a drag show they were having. By the end of the night I was so horny I was dying to suck some black cock as I am hopelessly addicted to the wonderful taste of them that I decided to go to the bathhouse on the ad.

I drove the few blocks to the bath and went in. The guy at the front desk told me how much for a "membership" which gave me access for as long as I wanted to stay as... Continue»
Posted by reesielover 24 days ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Jacki's Journey into Sissyhood

crossdress – sissy – anal - plug – oral

I thought to myself could I really go through with it this time? I had to at least try it, didn't I? I took another swig of wine and then brushed the blonde strands of hair out of my face again as and I read through the message one more time. "Jacki, Id love to get together and treat you like the beautiful gurl that you are. Look over my pics and if you like what you see, send me your number and we can set up something, Steve." I sat there in a matching red lace bra and panties and black patent high heels, with my makeup, and my favorite blonde... Continue»
Posted by naughty_bi_interest 19 days ago  |  Categories: Anal, Fetish, Shemales  |  
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my shemale GF part 3

Christy and I are on the couch, we had just woke up, I have a butt plug in and slept with it in cause she was going to fuck me today. She has a Pink G-string on and a Pink bra with her G-string pushed to the side for her cock. Me I'm wearing Metal Mulisha boxers and a Tyler, the creator T-shirt on, and I'm down on my knees jerking her cock and sucking her balls, ironic huh. The butt plug was pink and big at the base. As I'm sucking her cock, her roommate and also my friend, Ashley, walks in, I believe this was no coincidence. Christy says to her "Hey sweety, why don't you join me?". I got a s... Continue»
Posted by germanface 4 years ago  |  Categories: Anal, BDSM, Shemales  |  
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Oh Joy Oh Joy

So its a Friday night and I'm ready to hit the town for a drink, I'm dressed to kill in a t-shirt and jeans not really looking for anything other than a drink. I walk to my local and order a beer knowing that some friends Will be here soon, well 3 beers later and still no-one is here i make a few texts and realise that they all are doing they re own thing tonight so I'm on my own till i spot a red haired girl at the bar, she seems to be on her own and she catches me looking at her and gives me a wink. I smile back and lift my drink and mouth to her over the loud bar would she like me to buy he... Continue»
Posted by mrspankytoyou 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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Weekend Office Sex

So I am the low man on the scale at work. My job is with the City I work in dispatch and am one of the people responsible for getting road crews, hydro and sewer crews out to fix problems wherever they occur. My boss is a very attractive woman named Jamie. She stands about 152 centimeters and dark chestnut hair that is short at the back but gets long at the front. It matches her deep espresso eyes. She dressed very professionally at work ankle length skirts, blouses and blazers that type of thing. She has perky c cup breasts that when she trots or runs through the office they have a nice... Continue»
Posted by triphammer73 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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How i became a sissy fuckslave pt2

Sometime later, i'm not really how much later since i seem to have dozed off, Sir came back in and woke me up by swatting my ass hard"Wake up slut".

Sir unlocked my cuffs, and my ankle restraints and said"Down the hall, second door on the right is the bathroom, go there, remove the corset, catsuit, boots and hood, remove the plug and clean it and yourself up.When your done I want you to put the corset on, and hood as well as the boots and then go to the room across from the bathroom.Don't worry about cinching up the corset, I'll do that when you get in the room.If you have to pee, your to... Continue»
Posted by analsubbieinmissouri 4 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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The woods

I met my sissy boy slut at the pathway to a secluded woods. Our eyes met as I walked past her and continued down the path, she followed without being asked and caught up And held my hand as we made our way to a hidden spot. My arousal was growing as she rubbed my arse through my trousers, I stopped by a large tree with a branch we could use to fuck on and over. I kissed her and ran my hands over her body the tight jeans allowing her bulge to been seen I un zipped her and put my hand in to feel silky panties and a hard cock! Then slowly pulling her jeans and panties down that rock hard little c... Continue»
Posted by kawa696969 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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How I became a GURL

So how did you become a gurl?

That's the question almost everyone I meet or chat with asks me... how did you become such a sexy transvestite, when did you figure it out, when did you learn you liked cock.

I actually love the question, because it turns me on to answer it.

When I was 15 or 16 I used to sneak into my parents room, find my dad's stash of Playboys and jack off to them. The girls were sooooo beauitful, I just couldn't believe it. I wanted to see and touch one, which led -- I guess this is common among us gurls -- to digging into my Mom's stuff.

When I was left alone I w... Continue»
Posted by jenn1 4 years ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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The Trannyformation

I headed back to the adult bookstore where I had my first taste of cock and cum. I needed more, and headed for the gloryholes in the back booths. It wasn't long before a man entered the next booth. He rubbed his crotch and slowly lowered his zipper. My heart was beating faster in anticipation of sucking his big cock. He pulled it out of his shorts, and it was about 3 inches long, and not very thick.

He moved toward the hole, his uncut cock being stroked slowly and tantalizingly, precum appearing at his piss hole. My face was at the hole as he pushed it through, the head and precum slipping... Continue»
Posted by keripinkpanty 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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Seducing Nelly, a TS erotic story

I first noticed Nellie on a Friday evening when my fraternity and her sorority got together to make a homecoming float. She had gorgeous blonde hair that flowed down to her shoulders, she knew exactly what she was doing with her eye makeup, lining them in black with a smoky finish. Once my gaze connected with hers I couldn’t look away.
I smiled, grabbed a couple beers from the ice trough, walked up to her and offered the drink. She smiled, accepted and introduced herself, “I’m Nellie” she said, I told her my name, we shook hands and both smiled. Her teeth were perfect, bright white surrounded... Continue»
Posted by Mskyeuploads 9 months ago  |  Categories: Anal, First Time, Shemales  |  
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My first real blow job

Over the years, I've become such a greedy whore for sex of almost every kind, and being blessed with a vivid imagination and curiosity I'm always ready to try just about anything....

I'm such a greedy bitch for pussy juice for example and I've always taken an enormous pleasure in offering a Ggirl many a long cunnilingus - Hearing her moan in ecstacy under the assaults of my feverish but sensitive tongue has always been an immense pleasure for me as well as for her and when she finally CUMs shooting great spurts of LUV juice all over my face as she screams in orgasmic yelling and swearing, i... Continue»
Posted by caroletv31 5 years ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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First meeting with Dom sissy mistress

I was a longtime secret panty sissy who played in private and only dared dream of finally meeting someone face to face when I met Miss Jamie on xhamster. We had an immediate rapport online and before long she suggested meeting. Of course, with her long experience as a sissy, and with me being an obviously natural submissive, she would take the role of teaching me my proper place as a submissive sissy. This is the account of that first meeting.

Miss Jamie's logistics were simple:
I was to park at a nearby shopping center and wait for her.
When she arrived, I was to get in her car.
She wou... Continue»
Posted by Shelleyisasissy 10 months ago  |  Categories: Fetish, First Time, Shemales  |  
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The morning I couldn’t control myself &helli

As I’ve mentioned previously in my little memoire, my Mother was very enlightened about me dressing but we had rules. One small problem is that Mother couldn’t get her very sexy arse out of her bed in the morning, one of the reasons that she worked for herself. So every morning, when I was at home, I had to take her coffee, try to wake her up and get her out at a reasonable time.

The morning I remember best was the morning I couldn’t control my urges any longer, she was just too sexy. She often slept naked but this morning she was a short, rather nice negligee type nightie and no panties... Continue»
Posted by antoniaf 4 years ago  |  Categories: Masturbation, Mature, Shemales  |  
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Mexican Boy Meets American Boy

My name is Enrique and I am from Chihuahua Mexico. Since a c***d I never really liked girls, but I didn’t seem to like boys either. That was true until I first went to visit the USA. I fell in love when I met a white American boy. His beautiful blue eyes, his pretty smile, his perfect body, and his tall frame attracted me to him. I never met a man like that in my life. I was 18 and he was about 23 years old. I didn’t know much English so it was hard to talk to him. But he knew I wanted him.

He lived in a Mexican neighborhood in San Antonio, Texas, and was dating my cousin Maria at the time... Continue»
Posted by wdl88 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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My Mistress

Last night my Mistress and I hit new heights (lows?) of debauchery.

The evening started simply enough with dinner, after which my Mistress asked me to fetch my collar and leash. I was told to get naked, and she put the collar on me. It was a little tight: not uncomfortably so, but just enough that if she pulled on the leash, the collar choked me and made my head swim. My Mistress sat cross-legged on the couch. She f***ed me to my knees and had me worship her boots, kissing them from bottom to top, as she yanked on the leash to guide me.

"Go and get your muzzle," she said, referring t... Continue»
Posted by malesub01 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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A walk in the woods.....

I was lounging around the house, like a lady of leisure, wearing an elegant robe in black lace with a pair of sensual seamed stockings held up by a six-strap suspender belt and of course a pair of my favourite spiky pointed hi-heels that are so comfortable to wear round the house. I'd put on one of my favourite bras and placed a nice pair of natural looking silicone titties inside - the whole ensemble topped of with some nice jewellery. The perfect femme fatale bourgeoise SLUT that I LUV to be. I'd just renewed my lipstick and was feeling very femme, VERY slutty and as HORNY as hell when the p... Continue»
Posted by caroletv31 4 years ago  |  Categories: BDSM, Group Sex, Shemales  |  
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Crossdresser gets Gangbanged

So one night i decided to be daring and go for a walk in my city dressed in my sexiest girls cloths (i'm just a 26y.o. italian 5'5" 125lbs body man). I had a skimpy pink top on the revealed my sexy pink bra and cut just above my belly button, for my piercing to show. I also had on a micro-skirt showing off my ass cheeks just enough to see standing straight up and showing off my tramp-stamp tattoo GET SOME right above my ass crack. Sexy pink thong underneath that plus knee high black leather high heel boots and sexy blonde wig. I did my make-up so perfect you would never tell i was a man w... Continue»
Posted by sexboi421 4 years ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
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