Shemales Porn Stories
Page 59

Last night I drank my own cum

Once upon a time...

There was a regular boy, who was always fascinated by women, but one day (casually) discovered the dirty and horny world of the "third way" of sex, the fantastic shemale-ladyboy-tranny universe, and it was like a shock for him, a very sweet shock, he never believed or thought in exciting himself by watching a girl with a cock, but instead that new world electrified him, and made himself very curious about these she-males, widening his love above women and becoming a real sex pig and an orgasm addict.


Well, that regular boy was me. I consider myself as ... Continue»
Posted by Porcellone 3 years ago  |  Categories: Masturbation, Shemales  |  Views: 1664  |  
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Wife was Away!

I hadn't been out for over a month and it was starting to bother me. Since I started dressing four years ago most of my excursions in public have been from fall till spring. Its easier to hide my shaved body in the cooler months, which makes me feel much more feminine. When I'm smooth all over I get to wear more revealing clothes and I can let the guys I meet run their hand anywere they like without them getting turned off by unwanted body hair.

My wife was about to leave town for ten days at a convention she attends every year and as soon as I dropped her off at the airport I ru... Continue»
Posted by kristygurl 4 years ago  |  Categories: Shemales  |  Views: 1659  |  
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IT WAS SO WRONG BUT SO NICE WE WAS JUST HAVEING FU

IT WAS WHEN I WAS 17 NEARLY 18 MY MOTHER AND FATHER SPLITT UP WHEN I WAS ABOUT 12--13 AND I LIVED WITH ME DAD IT WAS ALL GOOD WHEN I WAS 15 ME DAD MEET A NEW GIRL FRIEND CAFFE SHE WAS YOUNGER THEN DAD HE WAS IN HIS LATE 40,S SHE WAS IN HER ERLY 30,S THEY WAS WITH EACH OTHER FOR A WHILE THEN CAFF WAS MOVEING IN OWR HOUSE IT WAS COOL I WAS WITH A GIRL AT THIS I LOOK,T AT CAFF AS ME STEP MUM WE USE,T TO JOKE ABOUT HOW DAD WAS 17 YEARS OLDER THEN HER AN I,D SAY THERS THE SAME AGE GAP BETWEN U AND DAD AND ME AN U SHE WOULD SAY NO IM AN ADULT SO IS YOUR DAD U R STILL A TEENAGER WELL ATHTTER 2 OR 3 Y... Continue»
Posted by needyboy 4 years ago  |  Categories: Shemales  |  Views: 1659  |  
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Becoming Aphrodite Ch 01

My wife and I have been married for 10 years. She is a beautiful brunette of 5'8" and 120 pounds. With her long hair and her cute and innocent face, she looks a lot like the porn star Cheyenne Silver. I would dare to say she's even prettier: her extraordinary green eyes are totally unforgettable and even the famous porn star I mentioned could not compete with her.

We got married very young and we were very happy for many years but Jennifer was slowly changing, discovering parts of her which could not be ignored any more. In fact, she did not have enough sexual experience before getting marr... Continue»
Posted by slutyvanessa 2 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 1661  |  
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Becoming Alanna - Part 2

Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work with is there” she laughed looking at my small cock “but also not much to work with in the way of hair". She applied the preheated wax and then the strips to the areas around my cock and my asshole, the area connecting them and lastly my balls. She gently tugged them off and I cried with pain. “Oh shut up s... Continue»
Posted by KristyQuinn 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 1657  |  
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Walk his way

Just for the thrill of it all, I moisturized my freshly shaved body, combed out my long hair over my shoulders, and put on a pair of very short cut off denims, cuffed them even shorter, and a Betty Boop T shirt with the neck and sleeves cut out. I looked and felt very much on the fem side. Not really crossdressed, but without a doubt, sissified. I drove down the interstate to the nearest rest area and parked all the way at the end. I carried my little belly bag like a handbag, and walked to the rest rooms with a swish in my step and a grin on my face. Most people did a bit of a double take; a ... Continue»
Posted by dana213 4 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1657  |  
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About Me

I don't know where to start so I guess I will start where I first felt like I might like men. I was about 14 and walking to store for my grandmother. The neighborhood bully acosted me and when I was walking away he felt my ass. That was it. I don't know why but it felt good. I fought off those feelings for a while. Then when I was older I got an obsession with panties and lingerie. I started sniffing and wearing my s****r's. I fought that off. I went on to get married and then the urge came back. I started wearing and sniffing my wife's panties. I knew she was cheating on me and I would wait u... Continue»
Posted by pantyluver711 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 1656  |  
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Weekend with Kelly, my new lover, part 4

After we got out of the tub and ate dinner I asked her if she
was ready for dessert.


Her eyes sparkled and said "Of course my dear".



I told her I'll meet her in the living room.


She stood as I moved her chair back from the table. I kissed
her lightly on her lips.


Then, leaving the kitchen and going to the master bedroom
to get myself ready. I applied some lube to my favorite dildo
and slid down on it stretching my hole to ready myself for
her. Walking out into the living room and finding her relaxing
on the coach. She didn't hear me come into the room as
I snuck up... Continue»
Posted by Bigrodtaz 8 months ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1655  |  
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Riverbank Tranny Fucktoy

Hello to all of you that read my first true story about outdoor sex. This is another account of a meeting I had in the middle of a city near a river.

It was late one summers evening when I met up with this sexy young Portugese stud I had been messaging on a gay dogging site.

I had been chatting to Fillipe for a couple of hours, and we were both getting hornier and hornier with each new message that we sent. It was me that asked if he would like to meet that night, and he of course said yes. There are a few cruising areas near around the closest city to me and we arranged to meet at one... Continue»
Posted by donnamarie09 5 months ago  |  Categories: Anal, Shemales, Voyeur  |  Views: 1655  |  
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a naughty "girl" i was

Once again i had the house to myself, i got online and soon found myself an eager man ready to come plow me. I waited in my black tank and pladd mini skirt, running my hands up and down my thigh highs. Suddenly a knock at the door, i answered the door in a robe. After he came in i relized how big a boy he was. HE was easily 6'6" and round 250bls, i have to admit i was intimidated. I disrobed in front of him and a smile came aross his face. MY naughty little outfit had made a rather large buldge in his pants.
HE took his time with me, caressing my body and grinding ag... Continue»
Posted by witdacandy09 4 years ago  |  Categories: Shemales  |  Views: 1654  |  
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My First Meeting - A work of fiction

I had absolutely no idea what to expect as I rang the doorbell of Jane’s house. It was an extended bungalow on the outskirts of Edinburgh and it had taken me 30minutes to drive there, getting more nervous with each passing mile. Jane and I first contacted each other through as online transvestite networking site a couple of months previous. We had got on well, and often chatted in a private chatroom, and exchanged pictures of each other. While I was relatively new to being a tranny, Jane had been doing it for years, going on nights out and meeting people.

Jane answered the door, wearing... Continue»
Posted by misssuzywhyte 1 year ago  |  Categories: First Time, Shemales  |  Views: 1653  |  
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Island Fantasy

Part 1

My ship arrives off shore at about 10 in the morning local time. We drop anchor about a 1/4 mile out and busy ourselves with getting ready for some shore leave. I'm very excited because I've only been on the ship for about 3 weeks and I'm already getting to go to a new and exciting foreign country.
As I look over the sides of the ship I see a large crowd of small vessels starting to appear. They're locals, fishing boats, runabouts, and all of them loaded with people staring up at us.... at me.... I wave and they wave back. Friendly.

When its my time to depart the ... Continue»
Posted by SandyCrossdresser 25 days ago  |  Categories: First Time, Shemales  |  Views: 1650  |  
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T-Girl Rodeo

Howdy folks, we would like to welcome y'all to the finals for the 10th Annual T-girl Rodeo! Now this here being the tenth anniversary and all we're gonna put on one hellva show for ya! Commentating up here in the announcers box with me is the first ever T-girl Grand Champion, Lorna "Tail Buster" Johnson. Folks let's give the Tail Buster here a great big rodeo welcome! Say howdy to these good folks Lorna!

Howdy, good folks!

Hoo wee, Lorna those folks sure are glad to see you here with me!

I'd say they are! That's about the best applause I've gotten any where I've ever gone Slim!

Now... Continue»
Posted by germanboi4bbc 1 year ago  |  Categories: Fetish, Shemales  |  Views: 1648  |  
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Babysitter - Part 2

From: A K little s****r Alyssia

Babysitter - Part 2

I'm a mess in the mirror, well, I think I look sexy too with my hair all
tussled, a little cum rubbed over my cheeks and chin, and a grin like the
cat that ate the canary. The dress has some wet spots and a few small gobs
of his cum. I wash up as best I can and blot the spots on the dress, I
start thinking, Nicole is going to kill me! I might have ruined her dress
and I just gave her man a blowjob. That could be a problem. I still can't
believe it!. He kissed me and I sucked his dick! But I know I want to do it
again.. Did I real... Continue»
Posted by jayymie 11 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 1648  |  
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Sniff my Panty/Pantyhosed Crotch


Here's another story from my archives, updated slightly, friends...

Because my lover has such a big cock I can't refuse him anything, least of all his arousing fetish for sniffing my ass and crotch while I wear my shiny black full bottomed skintight panties under gleaming sheer to waist high gloss pantyhose!

It all started when I needed a wardrobe putting up in my new flat and my s****r recommended her boyfriend, Kev, to come round to do the job.
On this day when Kev came around to put the wardrobe together in my bedroom I decided to leave work early to relax after I got a lot of app... Continue»
Posted by leotardlust 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1647  |  
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The Cheaters

“God yes,” Lisette moaned as her husband flicked his tongue in and out of her hole. The five-foot-ten-inch brown-skinned beauty grabbed his head with both of her hands and pushed his face deeper into her ass crack. As he made love to her tranny pussy, her body, all one hundred and forty-five pounds of it, squirmed. She wiggled in every direction effectively working the fitted satin sheets off of their California king size bed. Her barely functional clit stiffened. “Fuck me,” she squealed.

Sensing his oral work was finished; Deitrick emerged from her anal cavity and stood on his knees. He ad... Continue»
Posted by faggyboi 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1644  |  
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Russian Shemales

(Translated from the Russian)

We lived in small village, no work, nothing to do but smoke all day. Friend Serge and I sitting by road one day, when black sedan, shiny from city stop near us. The man inside wearing a expensive suit, and ask if we want jobs as models.

Serge and I think must be joke. But man introduce himself as talent scout. He speaks Russian but with accent I don't not know where from. He says he is from modeling agency and is looking for new talent to model. Introduces himself as Mr. Aronoff, and asks us to stand and turn around. Looks closely at our faces. Serge... Continue»
Posted by TransContinental 7 months ago  |  Categories: Shemales  |  Views: 1643  |  
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a real cd explains what cd on cd sex is like

alot of "strait" guys love shemale porn.I was one of them.Pre-internet I discovered shemale porn but it was hard to find.I had girlfriends but the sex was never great.like many i was more concerned with cumming to soon than actually enjoying myself.Plus,as a porn watcher my fav was anal.My girlfriends fav...not so much.after 25 years i realized that i was most unhappy when i had a girlfriend.even then I had bought and worn nylons and enjoyed anal dildo play alone.then came the net.and i bought a wig,shoes, and some makeup.I had wanted to be with a cd.I didn't realize i could be an attractive ... Continue»
Posted by tran1001 2 years ago  |  Categories: Shemales  |  Views: 1641  |  
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My time with Maxine

About 7 years ago I use to chat often on one of the many chat messenger programs. I met a sweet and sexy Filipina named Carol and we became good friends and more. We would have cam sex when the urge would hit us but mostly we just chatted. She met an American in the Philippines and got engaged so that ended our chatting time together. She emailed me after we hadn’t talked in a few months and invited me to her wedding. She lived in Angeles City and from what I had heard it was quite a nice place, a lot of clubs and women.
Her soon to be husband was a lucky guy. Carol was 4’9, very cute wi... Continue»
Posted by crazy4filipinas 8 months ago  |  Categories: Anal, Shemales  |  Views: 1639  |  
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Amazing Birthday

Best birthday ever

Hello every one hopes all u doing great and enjoys my story

We all get d***k on our birthday and enjoy every second and get those feeling next day hangover or sore well I was sore from sex and not a big drinker but had few

Friends took me to movie I was wearing one piece shorts top jumpsuit in white no panties and lace bra in white high heel scandal we were group of tranny and black guys
Always fun. Anyway after movie we get to one of friend home we were drinking guys drinking beer few us girls drinking wine its was getting late 11pm I decided to get home few guy f... Continue»
Posted by shawn777 2 years ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  Views: 1638  |  
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