Shemales Porn Stories
Page 82

My First TV Cottaging Fun

My first time (And this is Genuine, I assure you)

I dressed under my normal clothes and took a rucksack with other bit's & pieces in and went to a nearby "Cottage" that had 2 Glory Holes, when I got there, it was empty, so I went in the middle cubicle, finished dressing: Stockings & Suspenders, High Heeled Lace up PVC Boots, PVC Basque etc.

I didn't have to wait long, the cubicle's then got occupied either side, through the peep holes in the door, I could see at least 2 other guys at the urinals.

Then I saw fingers appearing at the hole to my left, I looked through the hole on my rig... Continue»
Posted by uktvmaid 1 year ago  |  Categories: Group Sex, Mature, Shemales  |  
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My first TS (Part 1)

I know most of these stories are often full of cliches and often I debate how true they actually are. So now that I have experienced one for myself, I thought I would give this a shot.

So, after spending the last few months planning and searching for ways to put my ultimate fantasy to the test: to meet and f*** a TS/ crossdresser, last week the dream finally became a reality. The person in question was a tall, pale TS called Chantelle and whilst she lived down in London, it was a trip I had to make. HAving shared pics and steamy chats, the time had finally come to meet up and act out what w... Continue»
Posted by geoff_lovemachine 3 years ago  |  Categories: Shemales  |  
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My first pair

More accurately I would have to say they were the first pair I did not have to steal and try on while hidden away in my room. I am speaking of pantyhose and other sexy feminine things like panties,high heeled shoes, stockings and the occasional dress. My s****r had known for a long time that I had developed a taste for these silky lingerie. I remember the the time she caught me, or at least the the first time she let me know that I had been found out. I still very young, only about ten, but I had been secretly trying on my mom's or my s****r's pantyhose for a few years already. I must have sta... Continue»
Posted by stedehans 8 months ago  |  Categories: Fetish, First Time, Shemales  |  
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A good friend

I have a friend whos name is Novak.We have known each other since we were little k**s.We have always done everything together and have no secrets.But he didnt know that i liked to wear womens clothes.He has blue eyes,is very handsome and is very developed and he also plays football.Since we were really good friends i saw his dick several times and it was nice and big. Sometimes i dreamed i sucked it and that he came on my face.
One day we came to my place after a night out in town and he was d***k,so i decided to try to seduce him. He sat on the sofa in the leaving room while i was changing i... Continue»
Posted by nikoletakurva 4 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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transvestite in trouble 4 - the internet porn quee

Bright light filled the room, waking me from my unconciousness.

so bright it took a while for my eyes to focus. When they did the first site i saw was myself, in the wall sized mirror opposite me, strapped to the chair. It was me only now i had masses of long blode hair, tied up in 2 pigtails, loads of black eye make up and long false eyelashes, and big bright red lips. A new ball gag in my mouth, I was wearing a pink latex basque, white stockings and red slutty shoes, 6" heel with a 2" platform. I had on no panties, my cock was now locked in a heavy, metal chrome device, and there was som... Continue»
Posted by hornyTVluvr 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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PantyBoy Gets A Reaming

I love to get really in touch with my feminine side. I get so turned on when I watch a man look my body up and down while I'm wearing some really sexy lingerie. I feel so naughty and slutty, knowing that I am going to let him do anything and everything he wants to me!! I was chatting in a room on one of the big websites when an IM from a guy in my area came across my screen. He wasted no time telling me how he liked my pictures that I had posted and how horny they had made him. I told him that flattery would get him everything, and he immediately invited me to his place. I don't usually meet i... Continue»
Posted by LRock4fun 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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The Making of A Sissy-Part Two

As Bella blossomed physically, Jane ensured the girls took control of her; she was made to know her place amongst females and was still subjected to their choosing her outfits. Bella was habitually made to pose before a full length mirror as Jane and the girls scrutinised her feminine shape; the girls were especially pleased on those occasions when Bella was held naked before the mirror as they stroked and admired her sweet white thighs and bottom, cupped her deliciously formed breasts; the smiling girls actions making Bella’s sissy hairless cock rise with excitement. This gave Tara licence ... Continue»
Posted by midsummerman 3 years ago  |  Categories: Fetish, Shemales, Voyeur  |  
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Night out

My wife knew that I liked to dress and would often help me. Usually it just consisted of dressing up and watching TV or maybe having hot sex. Once she had me dress and took me for a drive to the park where she made me walk around and pose for pictures. She’d also take me to the local thrift stores where we’d buy new things for Michelle. In bed we’d often talk about me dressing up and going someplace in public like a club or show. It seemed to make us both hot and the sex we had afterwards was fantastic.
One weekend we had to go to Providence for a friends wedding. My wife told me she w... Continue»
Posted by MichelleSEmass 3 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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She wanted to Watch!

Everyone knows I'm bi and a Transvestite. I don't dress as much as I wish but I do go out two or three times a week. When I'm not dressed up I tend to hang at a straight redneck bar thats about two blocks from my house. They all know both mark and Kristy there and most are nice to me and respect me because of the respect I give to them.

Well yesterday I was in after work for a couple beers and Cindy the bartender and Lisa wanted me to do some drinks with them. Orange Crushes, wow I didn't want to get d***k cause I had plans for Kristy to go out clubbing. But after encou... Continue»
Posted by kristygurl 4 years ago  |  Categories: Shemales  |  
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A Walk after a Busted Date part 2 OR My First Day

A Walk after a Busted Date part 2 OR My First Day as a Hooker part 2

Toot-toot!

Crap that scared me! I wasn't expecting anyone to try to pick me up again. I thought it would have been a fluke. A one-off earlier with the k** and the handjob. Really?

Again? I can't say that I'm not flattered. I was, really. Gathering my nerves before turning to see who my next suitor was, I slowly turned without my legs shaking so much this time. Whomever was in the car, they would see me as fairly confident hooker walking the street.

Leaning on the passenger door of the Lincoln gave me a vie... Continue»
Posted by LeslieStone 1 year ago  |  Categories: First Time, Hardcore, Shemales  |  
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Fantasy fuck

Sitting in the toilet cubicle I have been horny all day my cock is semi hard and I run my finger over the eye as pre cum oozes from the slit, I taste it's salty flavour as I strain the p*o out mmm wish there was something going in rather than out! There is activity in the next stall and I see some flesh through the gloryhole as someone sits down, with my cock stiffer than ever and my heart beating I look through to see a beautiful tranny pull her satin panties down and strOke her cock her fingers wiggle at the hole as a invitation, so I go for it and place my erectiOn through the hole , wow ho... Continue»
Posted by kawa696969 2 years ago  |  Categories: Anal, Shemales  |  
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nigger's white sissy boy


I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin' HARD! Because of that I was able to convince myself that I was normal, of course, in retrospect it is obvious that I was identifying with the women.

One day when my mom was at work, I was laying in her bed, masturbating. I got up and rummaged through her underwear drawer. The dr... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Interracial Sex, Shemales  |  
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Playtime Stories Ch 5 - Best Leather Sales Lady Ev

5.

Shopping is not one of my favorite things to do. I still want to get there, find the items, buy them, and leave for home or wherever and use the items. However, I am female enough that I always want to have instant gratification and see how the item really looks on me.
A couple of years ago I had just begun to buy good quality “stuff” for my little whore-adventures. I was always awkward doing this because it is kind of embarrassing to buy erotic women’s clothing as a guy when it is plainly obvious that it’s your size. I also noticed that sales people are usually aware of my tr... Continue»
Posted by 6988slutty_rbckyy 3 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
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#2 - Nikki Gets Satisfied

It was about a week later and I had heard very little from the guy I had met up with. I thought he wasnt interested and was actually thinking about deleting him from my phone when he txt one morning to tell me he was going to be free during that day if I was free and that this time he had condoms. I took a while to think about it and told him he could come over to mine and we could have fun from where we left off last time. He seemed very pleased by this and requested what he wanted me to wear if I had it so I teased a little and told him that he will find out when he gets here to what im wear... Continue»
Posted by Nikki_93 2 years ago  |  Categories: Anal, Shemales  |  
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Rendezvous with Cheryl

Pulling up to the motel my cock was already rock hard just thinking about Cheryl. It had been a few months since my last trip to Baltimore and I so wanted her. We had met on craigslist about a year ago and rendezvous a few times. Now it is kind of a regular thing whenever I am traveling through. Cheryl always grabs a room at this seedy super 8 and then text me the room number. Cheryl looked so sexy today she had dark brown shoulder length hair that curled at the end, nicely lined eyebrows, long and dark eyelashes, her cute cheeks glowed matching her light pink lips. Two long earrings dangled f... Continue»
Posted by iheartm2f 1 year ago  |  Categories: Fetish, Gay Male, 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 8 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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Deep throat Made Easy

Deep throat Made Easy -reposted fro menext


Here for the first time ever are simple and explicit instructions on how to deep throat a penis. Position is important; you'll want to in position where you can extend and straighten your neck by slightly tilting your head back. This helps line up your throat with your mouth allowing the penis to slide in deep. The best position for beginners is with the receiver lying on his back with the giver lying on the stomach along side. You can prop yourself up on your elbows.

The penis must be THOROUGHLY LUBRICATED! I can't stress this enough. An... Continue»
Posted by bigdaddycoolzz 2 days ago  |  Categories: First Time, Gay Male, Shemales  |  
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unnecessary roughness

Some years back, I was on an overnight business trip. I would often crossdress in my motel room to entertain myself and practice looking sexy. I could pass as a real woman from a distance but not so much up close. I'd been strutting around in a short a****l print dress and platform heels, admiring myself in the mirror and occasionally walking around outside my room in the motel parking lot. There was a convenience store/gas station next to the motel, and I kept walking over toward it, daring to be seen by people filling their tanks, etc. Late that night I decided that I just had to go over to ... Continue»
Posted by dana213 3 years ago  |  Categories: Gay Male, Shemales  |  
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Scenario from vegas777

We are sitting on bed, on a sofa or the floor.
You wear sexy Lingerie, a corsage and sockings ad a panty.
Maybe at first we would give us tongue kissess
while we caress and explore each others body with our hands,
i would touch your tits and pleasure your nipples with my mouth,
then touching your belly go with my hand down you sexy legs and up again on
your back side grapping your round butt and knead him, while your hand also
go over my body you lick my nipples and your hand works the direction
to my dick, you touch it softly throug my boxers, which you slowly pull down.

Now my hal... Continue»
Posted by msxxx321 4 months ago  |  Categories: Anal, First Time, 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 7 months ago  |  Categories: Gay Male, Shemales  |  
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