Shemales Porn Stories
Page 16



I was just 18 when I went out whorin' for the first time. It was something I had an overwhelming urge to do after fantasising it countless times. I had been painting up and dressing since I was 13 and my 18 month older b*****r had been fucking me regularly since I was seven until he went away in the Army when I was 16, plus I had been shoving all types of objects in my pussy almost daily. My desire to have my pussy ravaged was insatiable. I used cucumbers and even a slender long Japanese eggplant about two inches in diameter, fantasizing it was a BBC. I reveled as I watc... Continue»
Posted by tvsllutmichelle 5 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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The Lindy Factor

When I walked in the first thing out of the ordinary was the cute little blonde sitting on the couch with all her books all spread out next to her and she was typing in her laptop. She stopped and moved an index card so that she could read it better and then noticed me.
"Hi", she said. "You must be Steve right? I'm Lindy and I'm in a couple of Julie's classes. She invited me over for dinner, I hope that's ok?"
I assured it was and I went through the small living room into the kitchen where I could hear Julie making supper. I walked quietly up behind her while she was washing something in ... Continue»
Posted by subjaye 5 months ago  |  Categories: Fetish, Shemales  |  
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The She Bitches part 1. or Trans Fu By wildrichie6

This is the first sex story I have written. I hope you all like.

Lora was 5'10 in her stockinged feet she loved stockings, & Killer heels. She had been getting hassle from a guy online for a few weeks now It had started off nicely enough, compliments a little heart gift. But there was something off. Lora had tried to let him down lightly, wanting to take time to know him she said. You know, no rush. But the guy just got abusive then threatening. Sending this message"got your ip address soon find you bitch then you'll get it" Fuck,,, this fucker was really getting to her. Ok she thought... Continue»
Posted by wildrichie68 5 months ago  |  Categories: Group Sex, Shemales, Taboo  |  
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Changing desires

Sat night 06/06/15

I had tried to open myself up all Fri night with no luck. I had a good enema, it took fucking ages to get clean. I did some poppers used my smallest toy to open up for the bigger ones. To no avail. My hole would not co-operate with my & my fellas attentions. I had closed up & my fellas tonguing had little effect, which totally got me pissed off as he is so good at it. Normally this always work if i'm a little uptight (happens sometimes).I had worn my hole out I pouted & pouted. I was beginning to get very forlorn as I felt I had let my fella down. Lots of pouting & sad fa... Continue»
Posted by lolawylde 5 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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i was in mistress jillian's home waiting for the guests to arrive.i was told by mistress jillian that tonight she will train me to be her slave for real.
it was 9 pm.
mistress was dressed in a beautiful white dress with no panties and bra underneath.
and i was kept naked with a leash tied to my neck as if i am a dog.i was hairy with hairy chests and hairy ass and also large bush over my cock and balls

at 9 15 pm the guests arrived.i found out mistress jillian accompanied with 2 beautiful ladies coming towards me.
she introduced me to the ladies and said that i am... Continue»
Posted by mistresspet26 5 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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A young man's summer [full story]


My name is Jason, and I am a typical teenaged young man; lean, horny all the time and really happy that I have reached the age where I can get a job that pays better than mowing lawns or delivering papers. My parents work all the time and me and my older b*****r John, have had the house to ourselves since I was 8 and he was 13, which meant no more getting up at 5:30 to go to a sitter who would either keep us all day or make sure we got on the bus for school.

I discovered the concept of sex early on; John would jerk off constantly if he thought no one was watching, this sta... Continue»
Posted by serious58 5 months ago  |  Categories: First Time, Masturbation, Shemales  |  
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A Night at the Metro

Before the inevitability of gentrification set in, Toronto's Metro Theatre stood for many years as the city's last full-screen porn cinema. And while more recent innovations in pornography (such as home video and later, the internet) had taken their toll, the Metro had things to offer which could not be had elsewhere. Living on the other side of town, I was an infrequent visitor to this one-time temple to sleazy entertainment, but on the occasions that I did, I'd usually have myself a good time. This story is about one such occasion.

Exiting the subway at Christie station, I could feel the ... Continue»
Posted by sissymaidjanine 5 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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Old man fantasy-Part 2

As i got home after i finished my job I got horny again,I have been thinking about the experience all the time since it has happened.I could not take off my chastity cage to masturbate..I did not know what to do I could not keep my mind off him so I called him and told him about this...i heard a lusty laughter for the first time and he sad "You will get addicted to me..I am gonna turn you into the best cum-dumpster,I will see you tomorrow".
I barely slept that night,he clearly succeeded in controlling was a big part of his plan,I was fingering myself without even noticing the reflex a... Continue»
Posted by cutecdkiss 5 months ago  |  Categories: Gay Male, Mature, Shemales  |  
  |  5

Becoming his girl (Sissy story by GirlyGay)

In the summer after my eighteenth birthday, I met Nick. He was a thirty-something who lived in our building. My parents had gone for their yearly European trip, and I had been left behind this year because I had college orientation during what would have been the last week of their trip.

Mooning and alone, with nothing to do for four whole weeks until my flight up west, I took to the pool to catch some sun. I had not bought new trunks in a while, and so my old ones were riding high on my legs.

Nick was already at pool, beer in hand, sitting back in a barca-lounger. His broad, smooth che... Continue»
Posted by sissyAlyna 5 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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The Rendezvous Pt1 (Sissy Story by CassidyCaine)

Nick looked at the email he'd received from his wife at lunch again as he got ready to leave work. It had been a month since he'd confessed to her his love of dressing up in women's clothing after he'd kept it hidden since they first met. But, Nikki was insistent so he had tried to share that part of him. She had worried he was gay or didn't want her anymore but he'd assured her that wasn't the case. Yet after all that worry, she had emailed him to tell him that tonight she wanted to play with his fantasy and role play a little to see if she could get into it. She had rented a motel room and w... Continue»
Posted by sissyAlyna 5 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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The Lady Inside by loyalsock

I looked at the sinuous curves of her body. The long legs, the curling hair. She was built like my fantasy, every inch of her in pale ivory and inky black. Her pumps hugged the delicate curve of her feet—the arch and the heel. Her dress matched in deep crimson and swung light and silky around her narrow hips and broad back. I stared, unsure if what I was seeing was real or just Hollywood smoke and mirrors. When she turned to me and smiled—lovely white teeth glistening behind her red, red lips—I almost fell backward. I was beginning to think she was a mirage brought on by the heat of the Mexica... Continue»
Posted by loyalsock 5 months ago  |  Categories: Anal, First Time, Shemales  |  

Nothing Else Matters 1 by loyalsock

About a week had passed since the incident with Casey coming by my work place, trying to blackmail me, by telling my friends I was dating a transsexual. I had talked with Christina about the whole situation, and she had been able to calm me down and help me relax. I had been so pissed off at first, that I couldn't even think clearly at the time. But with Christina's help, I was now seeing things a little more clearly than before, and I had even come to a decision of how I thought I could solve the problem without being f***ed to sl**p with Casey as she was demanding.

I would let everyone I... Continue»
Posted by loyalsock 5 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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summer vacation

hi my name is alex
and these is story is about, how i got my first taste of sperm.

it was the first week of summer holidays
i went to visit my grandmother, who lives in the north.
i took the train there, the cart was full first, but after several stops
i had it for myself.

i was really horny,so i looked around and saw i was really alone.
i took my dick out and started jerking it slowly.

as the time passed i got at my full size and i was pretty close to cumming.
the i heard a whisper behind me "hey boy, need any help"

i panicked and tried to hide my dick back into my pants .
... Continue»
Posted by readyCreampie 5 months ago  |  Categories: First Time, Shemales  |  
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Caught and made into a sissy slut

It was for real this time. No fantasy. Reality. I was dressed up in red: fishnet stockings, g-string, and a babydoll. I was wearing a metal chastity cage that was pulling my clit down, and it was a clit, it only half filled the cage. I had a new cock too - a black face dildo which was double-ended. In my new role, I had to jerk it as I was fucked in my pussy and I was being fucked. She had fucked me so hard that I was completely submissive to her, sucking on my gag with wild abandon, a true sissy slut.

It had started earlier that day when I had been caught jerking off to a mixture of cuck... Continue»
Posted by andygone 5 months ago  |  Categories: Anal, Fetish, Shemales  |  
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Dominant Sex Therapy

I had to go see a sex ther****t because I was addicted to jerking off. Little did I know she had a surprise waiting for me when i got there. I sat down and she got right to the questions. "So how long have you been jacking off" She asked. I said "about 20 years now" She nodded her head and asked " Do you watch porn when you jerk off?" I said "Yeah every time" She said "Good. How many times a day do you jack off" I said "all depends sometimes once, If i get a really good scene I try to break my mind from cumming too fast so it can be, 4-5 times a day." She said "Wow that's a lot of masturbat... Continue»
Posted by michneo 5 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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my date with jennycumslut part two

The second part of my story about my date with Jennycumslut. This memory will be burned in my mind forever and thinking about it drives me wild to know I did what I always fantasized about! Hopefully this will make you cum hard...

I left off that I had just made plans with Jenny to see her later that evening. I was out for a nice paced walk in the park close to my apartment at the time we had made plans so I hurried back home. After drenching of sweat from hurrying home since I was to meet her in less than a hour I quickly showered and didnt have time to shave my pubes down.

Me and her t... Continue»
Posted by redhotnailpolish 5 months ago  |  Categories: First Time, Shemales, Taboo  |  
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Gary's Dressup Sissy

When I was a teenager I lived next door to a guy named Gary. We were friends for years but drifted apart as he was 3 or 4 years older than me, so when he discovered girls I didn’t see him for a while. However, one summer he and his then girlfriend had a fight, so being at a loose end he would invite me over to watch movies and play video games.

One day we were watching a movie, when Gary suggested watching some of his dad’s pornos. I eagerly said yes. So for a few days we would watch porno from about 10 am till 4 pm when his mom came home. His dad seemed to have hundreds of movies. One mov... Continue»
Posted by palmorr 5 months ago  |  Categories: Anal, First Time, Shemales  |  
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The last time I was a slut for cock

This is an account from my diary about the last time that I was a total slut for cock, before I realised that there was power in being dominant.

Went over to see Peter yesterday, it was about 8pm when I left his house but I didn’t have to worry about rushing home.
It was nice being with Peter again, he’s taught me so much the past year and he loves me in feminine clothes but he wouldn’t let me take the dress that I’d worn for him home. He let me go home wearing the bra, pants, stockings and suspenders though, it felt lovely wearing them when riding my bike. I felt so happy having spent th... Continue»
Posted by angelatvdom 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Old man fantasy

I have always been aroused by horny old men,I always wanted to be exploited by a group of old horny men until one day when i got this job that required me to take care of a 66 y.o gentleman.
He seemed so nice and since it has been my passion to serve other men i accepted the job without thinking twice.Things went well and we got along just fine..he was really funny and we became close friends very fast.
One day he called me and told me that he must speak with me face to face so that he can share a problem that he had for years with me,I rushed over to his place worried that something may hav... Continue»
Posted by cutecdkiss 5 months ago  |  Categories: First Time, Mature, Shemales  |  
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Vicky's Pink Diary 04

My head is spinning now, and as my uncle slowly pulls my panties down, I close my eyes dreading my fate!

I watch as he pulls my case out from under the bed. He takes a key out of his trouser pocket and unlocks the padlock.

"My god, how long have you had a key?!"

"Vicky, surely you remember losing a key a little while ago. It fell out of your jeans when your stepmother pulled them out of the washing machine. She didn't notice, but I did. Now I don't want to bring the other you up, but I did wonder why you would have a key in your jeans."

I knew I'd lost one of the keys, but I ne... Continue»
Posted by sparkyking 5 months ago  |  Categories: Gay Male, Shemales, Taboo  |