Shemales Porn Stories
Page 10

My First Night of Being a Sissy Cumdump

Well I first started dressing when I was about 14. One thing that I always noticed is that putting on slutty clothes makes me an absolute whore for cock and cum. Throughout High School I dressed in my alone time but never acted on my slutty urges from fear of being caught by my parents. When I moved to college that all changed though. As soon as I got settled into my private dorm room, I thought it would be nice to spend the evening dressed like a little slut. I decided to wear my schoolgirl outfit that night. So I took a nice hot shower and shaved myself smooth from the neck down. I went back... Continue»
Posted by cumslutchloe 6 months ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 3603  |  
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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 4 months ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 3600  |  
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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 1 year ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 3589  |  
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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 11 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 3591  |  
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The Bike Path

I've been wanting to submit a story for a long time. I have a ton of ideas for some fictional sex stories but very few real life stories to talk about since my sex life is fairly normal. this story was special because it happens out of the blue and with a dream girl.

My buddies and I had been planning to attend this festival downtown. To avoid the traffic and trying to find parking, which can always be a bitch and not to mention the parking tickets if the meter runs out, i decided to leave the car at home and public transport. This also left me the option to drink and not drive or even t... Continue»
Posted by mikmarkham 9 months ago  |  Categories: Anal, Shemales  |  Views: 3590  |  
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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: 3579  |  
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My Aunt Gave Me A New Life




My Aunt Gave Me A New Life

As i already wrote, my Mistress has threated to turn me into a gay
shemale slut -- and i'm terrified. Last night i began thinking about how
this whole thing began.

We've lived next door to one another for years, and i've always admired
Her from a distance. She is beautiful! She has a small frame, 5'2",
dark hair, beautiful eyes, a dynamite little body with good size breasts,
beautiful legs. i guess You can say that She was my fantasy. A number
of years ago, when they first moved in next door, She came over with her
daughter to introduce... Continue»
Posted by klammer 3 months ago  |  Categories: Anal, Fetish, Shemales  |  Views: 3579  |  
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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: 3573  |  
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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 1 year ago  |  Categories: Anal, Shemales, Taboo  |  Views: 3568  |  
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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 5 months ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 3563  |  
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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 1 month ago  |  Categories: Fetish, Mature, Shemales  |  Views: 3564  |  
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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 6 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 3554  |  
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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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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 9 months ago  |  Categories: BDSM, Interracial Sex, Shemales  |  Views: 3537  |  
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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: 3529  |  
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Finding Out My Best Friend Is A Shemale

My name is Kayla and I had just started college when I met who was soon to become my best friend Mandy. Mandy and I did almost everything together and it was borderline scary how much we had in common and how much we shared the same interests. We shared a dorm room which was nice and it almost felt like we more s****rs than friends. I brought her home when I visited to introduce her to my parents who liked her a lot. Once we started sharing a dorm room I began noticing little weird things about Mandy like she wouldn't sl**p without wearing her long pajama bottoms and a baggy top even though I ... Continue»
Posted by xXSecondCitySaintXx 8 months ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 3524  |  
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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 6 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3523  |  
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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: 3517  |  
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I gave a blowjob to the taxi driver -TRUE STORY-

It's a 100% true story like the rest of my stories (Although it took 2-3 hours to seduce the young repairman *see: Airconditioner repairman laid some pipe*)

I never really liked clubbing unlike my best friend B. but she was really into that and therefore, i did accompany her several times despite enjoying the scene myself.

I went to clubbing on a Saturday night as usual with my best mate B., it was almost 23.30 when we arrived due to heavy rain that hit the region. Although it was rainy, the club was very crowded and packed with every kind of people - drags, lesbians,gay couples and e
... Continue»
Posted by Slave4str8twinks 4 months ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 3512  |  
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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: 3515  |  
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