Shemales Porn Stories
Page 12

Vicky's Pink Diary 01

There he is sat on my bed, my Uncle, Uncle Creep, well that's what I call him. I'm just staring in shock as he flicks through it.

"Put that down, it's private," I manage to blurt out.

"Don't worry, you poor little thing. I've read it right through a few times. I won't tell anyone, Vicky, isn't it?"

I'm shaking in horror, my diary, my pink diary with all my secret thoughts and wishes, my fantasies, and things I've done, embarrassing things. Well how many 18 year old boys get a kick out of wearing their and their stepmother's underwear and dresses? How many boys write things like tha... Continue»
Posted by sparkyking 8 months ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 3612  |  
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My day with Maggie

I kissed my wife jumped in the car. As I turned out of the driveway I dialed in work and called in sick for the day. As I drove to Maggie's I could feel my rock hard cock beg for relief. I tried not to think about it but my cock stayed hard the entire drive. As I pulled into the hotel and walked to the room number she had text me I felt nervous, excited and so horny all at the same time. No matter how many times we have sneak off together I always feel the same. Maggie opened the door and I quickly slid into the room put my arms around her as our lips touched. The kissing turned to passion as ... Continue»
Posted by iheartm2f 29 days ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 3614  |  
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An amazing true story

okay never done this before but here goes =) So i had just broken up with a girlfriend a couple months ago, and had been feeling pretty down and unhappy. I had a friend of my f****y invite me over to hang out and play some video games and eat some dinner. When i got to their house Jan and Ted, they have been married as long as i can remember about my parents age, were glad to see me and felt some relaxing fun would take my mind off things and everyone could have a good time. So we started playing some video games and drinking some wine when ted had to get up to do a little work and left Jan an... Continue»
Posted by xnotclspamx 1 year ago  |  Categories: Fetish, First Time, Shemales  |  Views: 3609  |  
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My New Girlfriend Turns Out to Be a Shemale.

Where do I start?
How about at the beginning. My name is Cal I am divorced and living alone. I am not a bad catch I am five foot eleven, short black hair, green eyes and no visible scars. I am a regular at the gym so I am in shape but not ripped. A seven inch uncut cock that I can use well. I dress nicely and have a good job.
My friends Don and Lisa were feeling sorry for me they knew how ugly my divorce was and how lonely I was so they invited me to their pool party last weekend. They said there would be some single women there and I might find someone I like.
Okay, I thought at... Continue»
Posted by triphammer73 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 3602  |  
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First Date

My urges to be with a man had been growing every day, so I decided to start an online dating account, to see if any guys were interested in me. In a matter of hours, I received hundreds of messages from interested men. One in particular stood out to me. He was 6'5" and muscular and a former marine. He sent me flirty e-mails and I flirted back and sent him a few pictures. After about the 10th email he told me that he had re-read my profile and he didn't realize that I was transgender. He told me he had never been with a t-girl but that I was so sexy that he didn't even care, he needed to take m... Continue»
Posted by xjessica88x 14 days ago  |  Categories: First Time, Shemales  |  Views: 3607  |  
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throat fucked by two black photographers

Well for a very long time i would go to a hotel room to dress up in my sexy outfits and set my camera on auto and take my own pics .After a while i got bored with that and wanted to do a photoshoot with a photographer so i rang around and found a guy who would take my pics .I went out and brought this sexy nurse outfit the day of the shoot this was the first outfit i wanted to wear .The night finally was here i am all dressed up make up on feeling very nervous but excited i reakon you could see my heart pounding out of my chest.There is the knock on the door when i opened it there was two very... Continue»
Posted by foxxiroxxi 2 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 3592  |  
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First time glory hole part2

...... I woke up and the lights were now on so I was guessing it was night and they close this place at 12 so was hoping that the man who closes it down let's me go so I looked at my watch it was 11 so was hoping someone would come soon.

Someone came in I guessed it was the cleaner cos he went into the other stall and sounded like he was cleaning so I was hoping he will let me go he had finished cleaning the other stall and then open the door to the stall I was in he looked in shock to see me sat there with no trousers on after being shocked he looked round went to the main door and shut it... Continue»
Posted by briggs123 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3593  |  
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Little MIss Sissywhore




Little Miss Sissy Whore


Chapter 1 -- The Pick-up

Every year I waited eagerly for the three days when PC-Expo was back in town. In the past, I was always able to find some willing and naive out-of-town female to pick up, "do the nasty," and say my hasty good-byes. Most of them were from some small hick town and were entranced with the Big Apple. In fact, that was both the nickname for the city, and for me. Most women just couldn't wait to sink their teeth into me. So there I was, looking for some love, on the last day of the three-day convention. I walked up and down the ... Continue»
Posted by klammer 4 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 3588  |  
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My first time

I sat in the car outside the address and to say I was nervous is a understatement. This was the first time I had ever done anything like this and I was half thinking of just driving away.

I had got messaging to Sara a month ago after liking the pictures they had posted. I was really in to clothed sex and the pictures showing Sara in a selection of boots whether they be leather or pvc, knee high or thigh high I didn't care as long as they have a stiletto heel l love them.

As for clothes I get hard for the slutty secretary look, a nice tight pencil skirt with some stockings and high heel... Continue»
Posted by big_rob49 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3584  |  
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Caught by my wife

I was stuck, I couldn't move, literally in headlights... I dress up okay? you caught me, I guess your the master now... I used to control my wives life and for good reason I pleased her, and she pleased me the best she could... well now that's changed.. she came home from work early last Tuesday and came in the side door of the garage, I use the garage to film my escapades. And all this time I've never been caught, now I'm caught and can not go back... I am passable. I'm always dieting, I work out but I work out to slim and femme myself.. My wife has the most beautiful body ever, and thats why... Continue»
Posted by reefermcrevolver 2 years ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 3584  |  
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Sissy Serving Poker Night

I was terrified when I was actually invited to serve at the usual Friday night poker game with 5 guys I had been talking with online. Three of them are black and 2 are white. I arrived at the house to find a nice setup in a basement rec room with a card table and a pool table.

I was nervous as I approached the front door and knocked having never done this before. The party host answered and immediately I was told to get dressed in something sexy and start serving drinks. Well since the only thing I brought with me was my thong and high heels, I put those on and came out, trembling with nerv... Continue»
Posted by johndavies4321817 9 months ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 3567  |  
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married my young son

Hi, am Zizi, am 35, am not what you'd call a natural woman, am quite fake, by that I mean am a very fake bimbo, blonde, blue eyes, high cheekbones, incredibly busty "fake 38DDD" and I always wear ultra padded bra, unless am fucking someone.

I always wear shiny or glittery short dresses and super shiny pantyhose, I never wear heels less than 6"...and nothing of this is painful as I take steroids and had this lifestyle since I can remember along with my friends; we used to compete who can get the most boys, I used to come either second or third because of that bitch Marissa...oh look at me, I... Continue»
Posted by starlight8998 5 months ago  |  Categories: Fetish, Mature, Shemales  |  Views: 3562  |  
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Black Mamba - pt 2

As I entered the bedroom, Jennifer indicated that I should stand and
approach her. I rose to my feet and stood before her feeling intimidated by
her size and demeanor. Jen reached out and yanked my precum soaked panties
down to mid thigh, roughly f***ed my now withered member between my legs
toward my ass, then pushed my aching balls up into my body cavity. She then
drew up my panties tightly so that my cock was effectively trapped.
"When you are in my presence, your worthless clit is to remain tucked away
as it is now, unless I order you to do otherwise. Do I make myself perfectly
... Continue»
Posted by germanboi4bbc 10 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 3555  |  
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Flying High



The plane landed as scheduled. Luckily it had been a very smooth flight. I made my way through the busy airport. While I was waiting for my luggage my eyes went everywhere looking for beautiful girls. I saw my luggage come around and went for it. At the same time a voluptuous brunette reached for the same bag.

“Excuse me,” I said. “I’m pretty sure this one is mine.”

“Oh I’m so sorry, the look like mines.” Her voice was soft and sounds a little hoarsed. I looked her up and down. She had a very latin style, which my cock i... Continue»
Posted by Pedeco 2 years ago  |  Categories: Shemales  |  Views: 3553  |  
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turned into a slut by my dad

I opened my eyes, blinked, yawned, closed them again.

I felt confused, disoriented in a way that was... strange. It wasn't like waking up was supposed to be, I wasn't half asl**p. I can't remember getting in the bed, in fact I can't remember the last thing I remember. Where did consciousness end last? I was clueless.

I tired to move my body and I found it difficult. I could move though, I rolled over onto my stomach and opened my eyes, I was on the guest bed in the basement. Blinking didn't clear the fuzz from the world, so I went ahead and tried to get out of bed. As I stood I felt an i... Continue»
Posted by crossD93 2 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 3545  |  
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His sissy sex slave

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 draw... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: BDSM, Interracial Sex, Shemales  |  Views: 3543  |  
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He caught me in his wife's cloths

I do odd job's and I was about to do one for my wife's best friend Tina and her Husband Phillip. I went over and looked at the job. I told her it would take several days and that I could do the work while her and her husband were at work. That way I wouldn't be in anyones way. Well the first day of the job I showed up just before Tina left for work. Pillip was already gone. We chatted a while the she left for work. Tina is really very hot and I have wanted to fuck her for a long time. Sense i knew that was not going to happen I thought I would do the next best thing. I went stra... Continue»
Posted by firstknightd 3 years ago  |  Categories: Shemales  |  Views: 3539  |  
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A cum slut is born

There's little doubt about what turns me on most -- just check out my favorite videos and photos. Cum, Cum, and more cum. I'm a late bloomer as far as discovering my kinky side. After a long, dull marriage consisting of vanilla sex, I got divorced a few years back and decided to explore some fantasies. I love porn, and I've always been somewhat envious of the chicks in the xxx vids, they always seemed like they were having tons of fun getting their cunts, mouths and asses filled with hot cum. Multiple cum shots really turned me on. But I'd always identified as heterosexual -- so how could it b... Continue»
Posted by jizzlover123 2 years ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 3531  |  
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The first encounter

I remember my first relationship with another man. Sixteen, still in high school in a small town and ready to go to anywhere but where i was. John was 30 and a high school teacher. We met at a summer camp. A group of us became friends and would meet on week-ends to party and generally hang out.
The first time that John and I were alone came that first fall; following the end of summer camp with both of us back to school. John called me and asked if I wanted to get together with some friends. So he picked me up and off we went on a Saturday morning adventure. We started the party fairl... Continue»
Posted by christoboy30 11 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3526  |  
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My first time with a shemale (true story)

My girlfriend had been out of town for a couple of weeks and i was so horny and wanted to get upto something kinky.
I called a shemale site from la costa del sol called taiakshemales and arrange to meet one of the beauties.
I was very nervous as i drove to her house as i never touched a dick before.
Once i was in her room waiting for her to come out she was wearing this sexy lingerie very slutty and a bead panties that just went around her tool.
She asked me if i had any experience and what i liked most, i told her i had never touched a dick and was very passive and shy.
The next thing sh... Continue»
Posted by allurs85 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 3520  |  
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