Shemales Porn Stories
Page 67

my first gay fuck

I've slways crossdressed, from when I was 12 years old. I started by wearing my Mum's knickers and bra, tights, knee high boots and a dress or skirt and top. it felt fantastic wlaking around on high heels, in the back garden, knowing that all the neighbours had to do was look over the fence and see me all dressed up! My cock got so hard and I'd wank myself dry!
I carried on all through my teenage years, using girlfriends underwear. At the swimming pool, where I used to work, I'd have a shower wearing the girls high cut swimming cossies! The feel of the wet lucra around my ass and cock was rea... Continue»
Posted by Nikki_xd 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3127  |  
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Hooky

"You're not seriously gonna leave me like this are you?" Daddy Mike said as he waved his now hard (again) cock back and forth. I stood on wobbly legs as I had still not gotten used to walking in the heels daddy bought for me.

"Daddy I gotta go to class, you already fucked me twice. You can fuck me again after class, now I gotta find my clothes and get out of these stockings and thong." I looked around for my pants but couldn't seem to find them which seemed to make Daddy Mike harder as he watched me bend over a lot to look for them, the heels he bought for me to wear during our play enhanci... Continue»
Posted by sublimeguy 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1500  |  
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Shopping

As I walked through the shop my heart raced. I was here for one reason. To buy women’s lingerie. I had always chickened out at the last second and was determined to go through with it today. I slowly made my way into the small shop browsing over nothing in particular when a older good looking guy came up to me.

"Is there anything I can help you with" he asked with a grin.

"Uh...yeah....I was uh, looking for something for my girlfriend." I asked nervously.

"What exactly are you looking for?"

"Uh, something sexy."

I just knew he could see right through the lie but he didn't let ... Continue»
Posted by welshcd 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 2312  |  
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Cast party

Cast Party


My name is Dan, and I have always considered myself an adventurous and open minded person, but my experience was taken to a whole new level in my junior year of college when I got involved in an amateur theatre group. We all got along astoundingly well and I found myself becoming friends with several of my cast-mates. We often went out for drinks and to parties together and after a very successful production of Romeo and Juliet, we decided to have a cast party at an international sorority house where several of the girls in the cast lived. During the long months of rehearsals ... Continue»
Posted by valeriuscatullus 3 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 1005  |  
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my girlfriend Allison has got a cock

MY GIRLFRIEND ALLISON HAS A COCK
I met Allison at a club she was by herself at the bar and when I looked at her I was smitten I knows that sounds cliche but it was like that for me! I sat down a few seats down and ordered a drink a whiskey sour I believe it was took a few pulls to get up my courage then I offered to buy her a drink and she looked over at me with these incredible sea green eyes and actually smiled at me "Ok " she said and ordered white wine which she sipped so sexily I asked her if I could sit beside her and she patted the seat next to her I couldn't believe my good luck to ... Continue»
Posted by pesty 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 5020  |  
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SOMETHING ABOUT DANNY

What was it about my daughter's boyfriend that turned me on so much? No one characteristic comes to mind. I suppose it was a combination of things. And perhaps a certain time in my life also. I was 52, divorced, alone and quite bored.

I had been divorced from my husband Jerry for 12 years and didn't really have a steady boyfriend. Jerry and I remained friends but he seemed to be turning into an old man. I was still young at heart, or so I felt. But the more men I met the more disappointed I became. It had been getting to the point where I would rather stay in my apartment and read than go o... Continue»
Posted by couple_kinky 1 year ago  |  Categories: Fetish, First Time, Shemales  |  Views: 4009  |  
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The Trip part 2

I awoke suddenly feeling dazed and with my head pounding.

"Kara, baby...you okay?" asked Chris

Chris roused from his slumber and reached for me. I was sitting up, breathing hard.

"It was nothing. Just a dream, I guess."



"Okay. If you say so." He rolled over to look at the clock. "It's about time to get up anyway. Must have been more tired than I thought."



As I gathered the covers around me, I noticed, I was wearing a Japanese schoolgirls uniform, there were red marks on my wrists that looked like rope burns and I could feel fresh cum leaking from my ass. Chris saw me squirm... Continue»
Posted by kara_zor_el 2 years ago  |  Categories: Shemales  |  Views: 707  |  
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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 3 years ago  |  Categories: First Time, Shemales, Voyeur  |  Views: 1353  |  
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Unexpected Secret

My neighbor and I get together almost every day after my husband goes to work. We have become very good friends. We go shopping, watch soaps, play cards, and cook together, all kinds of stuff. Her name is Linda. She recently revealed to me that she has a secret and isn't all that she appears to be.

Linda said she is a man who has been living full time as a woman for ten years now. She said she had breast implants and electrolysis. I couldn't believe it! She is feminine in every way. Her looks, mannerisms, clothes, make-up, body language, voice, everything, is always a woman.

So, I asked ... Continue»
Posted by nova169 2 years ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 2783  |  
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2 men using my mouth

Imagine your expecting a salesman to drop by at noon to show you some samples of wallpaper-You start your shower at 8 AM-you finsh up by shaving your legs real smooth-you go and put on a pair of full cut thin strechy full cut skimp skamp white panties-next you pick out a lovely open girdle and pull it on and attach your suntan colored stockings-the ones with the shiney look-you pull them up real tight-then your thin see thru bra and your size dd silicon titties the ones with the big nipples that stick strat out-then a thin strechy spandex-lycra slip dress-a long brown wig and a pair of... Continue»
Posted by tvdomm 3 years ago  |  Categories: Masturbation, Mature, Shemales  |  Views: 2496  |  
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Friends

Another story off the web. Enjoy

i have been friends with my next door neighbor for about 5 years now. he recently divorced his wife, but somehow managed to keep the house. So, we have been doing the bachelor thing together for the last few months... beer and cookouts on sundays while watching football, getting d***k, fixing cars, etc. my wife complains a little about this, but all in all, she puts up with it. she uses the weekends to visit her s****r (who is ill) and go out with the girls. i definitely make it up to her, above and beyond.

yesterday, our typical group of friends was una... Continue»
Posted by BeeJay69 1 year ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 1315  |  
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16 ladyboys jerked off in front of me! live!

Just got back from Thailand and had a very special birthday present. A big party had been arranged for me at my favorite ladyboy bar and a “competition” had been secretly arranged for me.

Had a nice party with balloons, food, drinks etc then a midnight I was told that it was now time for my birthday present. The door to the bar was closed a chair was bought out and put against the closed door and I was told to go sit on it. Then I was blindfolded and a bib put on me. I could hear all the ladyboys giggling and moving about.

The blindfold was removed and I was greeted with the site of ... Continue»
Posted by toniparr 2 years ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  Views: 1495  |  
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Delilah and the Deep Blue Sea. (part four)



The skipper of my boat was a man of few words it seemed for he maintained a taciturn silence as we sailed away from the island. I didn’t mind the lack of communication. I huddled miserably in the stern of the fishing boat, lost in my own thoughts and hardly in a mood to talk. My tear blurred eyes were fixed upon the dwindling view of the island as we left it far astern. Soon it was nothing but a pinprick on the horizon and shortly afterwards I lost it in the afternoon haze. It felt as if something had been torn from my soul.
I blinked away my tears and glanced ahead. A sliver of land had ... Continue»
Posted by Mikebasil 2 years ago  |  Categories: Shemales  |  Views: 1278  |  
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Xdresser Housewife Roxys daily chores while wife i

Well the best fuck I've ever had and continue to have all started when we intalled a pool in our back yard .Once the pool was in the pool shop sent over a young guy to set up the pump and show us how to use it ,as it was a Saturday my wife was home and she was in a bikini looking very hot. Well in walks this 6"5 very toned very sexy black guy ,when I say sexy he is the sexiest guy I've laid my eyes on and the body his arms were huge ,not one ounce of fat ,man the thoughts going through my head were insane but the one thing I knew is I had to have him 100% I would do everything I could to get t... Continue»
Posted by foxxiroxxi 1 year ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 1330  |  
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Caught by a neighbour in my s****rs clothes.

It was 10 o'clock on a Friday in late June of 1997. My parents were away visiting relatives for a few weeks. My s****r Kate had gone out partying with her friends for the night and wouldn’t be back till Saturday morning. Which left me all alone in the house.

For as long as I could remember I always loved dressing up in my s****r's clothes. When I was lucky enough to have a whole night with them out of the house, I usually went all out in my s****r's room. ??
I had been shaving what little body hair I had for years. I used to lie and tell anyone who noticed that a lot of swimmers and athlet... Continue»
Posted by kara_zor_el 3 years ago  |  Categories: Shemales  |  Views: 3734  |  
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Leila's Secret

I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most.

It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before.

I'd stayed over at a friend's house and after a nice leisurely breakfast I headed home so that I would be back home before dark. I had to be at work the next day and wanted plenty of rest.

I was driving along Highway 1 when I first saw her. And boy, was she a vision. It had been raining all morning and the woman who stood there beside the road w... Continue»
Posted by nova169 2 years ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 1381  |  
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She was a he

Few years back I was in a bar in London getting a round in for the lads before we hit Fabric.
I will be the first to say I'm not the fittest of guys and rely a lot on my charm. I took the drinks back to the table and returned to the bar to grab mine when a stunning Asian girl caught my eye and smiled at me. She glided when she walked, a smile that made your heart melt and a body to die for, why was she heading over to me....?

We chatted for a while and I agreed to meet my friends in the club a little later so I could get to know this amazing angel. We chatted, flirted and laughed until th... Continue»
Posted by dirtydisco99 2 months ago  |  Categories: First Time, Shemales  |  Views: 4871  |  
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Two trannys dominate me

I never thought of a day that I would be involved in a threesome. Especially a threesome with two trannies. It was lonely bar night for me, nothing special. I sat drinking all of my problems away. The rum and cokes were strong that night. I sat thinking about my life and wondering if life could actually be enjoyed. See, I was always that person who thought living a mild manner, do goody, life was the correct choice. But then why was I here drinking my life away? Something was missing. I was lonely at the time, no one to drink with, no one to call, no one to talk too. The bartender saw... Continue»
Posted by bigwangcum 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 2475  |  
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I was Used








I Last night I went to an adult book and video store to mainly buy a new dildo to fuck my ass with.I found a nice 8" real looking one that had multiple vibrator settings and picked up a bottle of lube as well.I of course got sidetracked looking at gay videos and magazines as I held on to my new toy and lube.As I browsed the videos a buff looking obviously gay couple walked in.They were looking at videos and the different lubes.I would peek at them from time to time and smile....very hot....one was 6', blond, 30ish, without an ounce of fat on him...acted like the bott... Continue»
Posted by LSancho 2 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 2024  |  
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The night I stayed in Nashville ( as a sissy )

I was traveling to Florida from Missouri to see my k**s. I new always stay the night in Nashville, and sense I would be alone in the hotel I thought I would pack a few of my sissy things. The thought had me hot the whole trip so I had to pull over early and slip into a rest room in a truck stop to put on some things for the drive. I put on some pink panties and stay up stockings, also a little camisole under my shirt. Wearing these under my cloths had me excited the whole trip. By the time I got to Nashville I was fit to be tied. ( literally )I checked into my hotel and started to get dressed ... Continue»
Posted by firstknightd 3 years ago  |  Categories: Shemales  |  Views: 1304  |  
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