Shemales Porn Stories

School Days ( I didn't write this )




Christopher Reilly woke up early that morning and quickly showered
and dressed in his school uniform. He was a freshman at St. Mark's
Academy for Boys, and although his studies were progressing nicely, he was
still homesick. It was November and he had been away from home for over
two months. He had always been an excellent student in grammer school and
from his earliest years had been something of a teacher's pet to the nuns
at St. Stephan's. Boarding school was a new experience, however; he
missed his mom and s****rs and, although he never would ha... Continue»
Posted by whiteshadowz 13 hours ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 825  |  
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Paying rent

I’ve always enjoyed getting dolled up like a sexy girl ever since I hit puberty. Doing my hair, wearing frilly panties, skirts, painting my nails and doing my makeup. But being a boy that isn’t viewed as proper behavior. Which is why I’ve always had to dress in private. But luckily with the power of the Internet I’m able to express my inner girl. I run a blog where I post dirty pics of myself dressed up, erotic stories of young crossdressers being used by older men, captioning dirty pictures and I do webcam shows just about every night. I even get tipped for my webcam shows and can use the mo... Continue»
Posted by ScarlettMaeBottom 1 day ago  |  Categories: First Time, Shemales  |  Views: 3260  |  
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My girlie fantasy part 2

A few days passed since my heavenly Halloween night with the wondrous morning after & I was so excited at the possibility of meeting up with the stud that took me like a woman again. Since I knew Halloween wasn't for another year I invested in a new outfit so to meet him in. I returned to the bar one week afterwards but he never showed, though several men hit on me I never entertained them at all. The bartender wasn't the same so I never asked if they knew my hunk or not. Disappointed I went home but was motivated to keep trying. Realizing I only had one new outfit I went shopping the ne... Continue»
Posted by multiplierx 2 days ago  |  Categories: Anal, Fetish, Shemales  |  Views: 888  |  
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My CD / Sissy story and 1st meet humiliation

I recently met up with someone to be a sissy slut for them and wanted to share what happened on my first meet. This is the genuine true story. I use the username indoblu on websites, but my sissy name is Holly so I'll refer to myself from now on as such. I'll mention my history as a sissy before talking about the meet up, skip the first few paragraphs to get to that bit.

I have always known I love girls clothes, lingerie, miniskirts, colourful sheer blouses , anything satin or lace, since a very young age. When I was 18, I finally had a credit card, and bought my own lingerie. I bought clot... Continue»
Posted by indoblu 3 days ago  |  Categories: BDSM, First Time, Shemales  |  Views: 1489  |  
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ANGELICA BEGINS - MY FIRST MAN (ENGLISH)

If anyone has read my story about my c***dhood, when I was 12-13 years old and I liked to wear my mother’s stockings and heels, will understand that I always had a feminine soul. But as I wrote in that story, at that age there are not yet social life, moral, f****y, friends to influence you and for me it was perfectly normal ... then growing up, f****y, friends, school, civil life affect you and make you forget your true nature. After the c***dhood I lived as nice “normal” and straight boy; cute, loved by girls, beautiful body, let’s say a “normal” sexual life.
I was anyway found of shemales,... Continue»
Posted by AngelicaTrav 3 days ago  |  Categories: Anal, First Time, Shemales  |  Views: 822  |  
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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 3 days ago  |  Categories: Anal, Shemales, Voyeur  |  Views: 981  |  
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A used sissy

“This one right here” Bob said. “This little sissy is perfect!” Bob and his two friends had spent the last few weeks scouring Craigslist personal ads for a small transvestite that they could take advantage of. “I’ll email the cunt with a pic of my nine inch cock – see if she bites!” Bob said. Sure enough a day later, the TV named Debi contacted Bob with pictures of “her” own. Bob shared the pics with his friends. “Look!” Bob said, “The cunt could pass easily, and the sissy even has little sissy boobs! Oh, this is gonna be fun! ” They all agreed that Debi was to be the one.
Debi had said in... Continue»
Posted by tvdebi 3 days ago  |  Categories: Shemales  |  Views: 1023  |  
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Car Bonnet Cockriding Whore

Hi Guys,




This true story dates back about 4 1/2 months now, and takes place outdoors, well over a car bonnet to be exact.


I had been chatting to this lovely guy called Dave, we had been chatting on a different site and arranged for him to come over from where he lived to where I live in Droitwich. Well I had been getting my self ready most of the evening showering, shaving my self totally smooth including my pussy, made a real effort to look hot with my makup and clothes. The usual things, stockings suspenders, 1/4 cup bra with matching thong, and high heels, a loose fitting top ... Continue»
Posted by donnamarie09 6 days ago  |  Categories: Anal, Shemales  |  Views: 5918  |  
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My girlie fantasy part 1

On a Halloween night I dress up in my sexy devil costume with my wig & some makeup & go to a local bar sitting alone. A guy ends up sitting next to me & flirts a little before I ask if he wants to go to the restroom with me to which he eagerly agrees. After getting in a stall we makeout for a little as he fondles my small breasts before I go down on my knees & pull his average size snake out & get to work. Shortly after starting he rewards me with my first taste & runs out embarrassed at how quick he finished leaving me wanting more. I sit back down at the bar & eventually another guy takes a ... Continue»
Posted by multiplierx 6 days ago  |  Categories: Anal, First Time, Shemales  |  Views: 4330  |  
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My Fantasy Meet

So what is my fantasy...well I suppose that being on this site is a bit of a fantasy in a way as I’m basically a straight guy who has become more and more turned on with the idea of wearing lingerie...then discovering this site accelerated the process and has made me more and more curious to actually meet another dresser like myself...I’ve also had plenty of hot times masturbating on c2c on here too and in doing so have graduated from wearing panties to stockings and now lipgloss, wigs, slips, pearls and heels...so I think that I am so ready to take the final step and actually arrange a meet.
... Continue»
Posted by Michelle62tv 6 days ago  |  Categories: Shemales  |  Views: 788  |  
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Car Bonnet Fuck

Hi Guys,




This true story dates back about 4 1/2 months now, and takes place outdoors, well over a car bonnet to be exact.


I had been chatting to this lovely guy called Dave, we had been chatting on a different site and arranged for him to come over from where he lived to where i live in Droitwich. Well I had been getting my self ready most of the evening showering, shaving my self totally smooth including my pussy, made a real effort to look hot with my makup and clothes. The usual things, stockings suspenders, 1/4 cup bra with matching thong, and high heels, a loose fitting top ... Continue»
Posted by donnamarie09 6 days ago  |  Categories: Anal, Shemales  |  Views: 997  |  
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Becoming a Sissy Cocksucker (true story)

I always loved feminine things. I'd wear my s****rs panties as often as I could. I loved the way they felt, the soft fabric, the high cut legs, and especially the frilly lace edging! I graduated to bras and padding them and wondered what it'd be like to be a girl.

I always loved watching porn where a guy is sucked off by a
woman. I started to realize, what turned me on the most about it was watching his cock when it orgasmed! I LOVED watching the cum shoot out and on to her face and in her mouth! I used to watch it (and still do) dressed in panties. Well, fantasy eventually took over, I wo... Continue»
Posted by vickiebicd 7 days ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4438  |  
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Life Changing Encounter

My name is Tony and I want to relate my story about a recent change in my sexual attitudes and preferences. When I was small my parents were divorced and my father never came back to visit me or even write a letter so I grew up with my working single mom.
During most of my life I was heterosexual. When I was twelve I came by some Playboy magazines, given to me by a friend, that displayed impossibly beautiful women in various suggestive positions. I had not had an orgasm yet but during the last few months I would wake up with a stiff cock which, at first, was disconcerting as I had no idea w... Continue»
Posted by johnny49r 8 days ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 3494  |  
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Sissy Tranny Annie Slutty Fantasy

I have been dressing since an early age, dressing in my mothers stockings, suspender belt, bra, panties and heels. I used to feel my smooth legs and my cock would get hard straight away. I love how my cock looks when im dressed as a sissy slut and from that early age all ive ever wanted is to have a horny guy in front of me, with his cock hard knowing that he wants to fuck me.
My fantasy and dressing got a lot more sluttier when I first in with my first love. Her name was Claire and she loved wearing hold ups, thongs, and best of all she loved to wear really high heels and she was the same s... Continue»
Posted by danny241976 8 days ago  |  Categories: Anal, First Time, Shemales  |  Views: 1494  |  
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First time with Brooke.

A few years back I lived on the 2nd floor of a four-flat apartment. Downstairs from me lived Brooke. She was an attractive girl, about a year older than me. We were both divorced at the time and she knew I spent most of my nights alone. She would often invite me down for dinner and vise-versa. Other times we would hand out in each other’s apartment watching TV and talking. I liked her but I didn’t feel that she was interested in me. Plus, she had a boyfriend at the time. He was the athletic type that worked in the corporate world. She really didn’t talk about him too much and since he lived do... Continue»
Posted by ahsleymills 8 days ago  |  Categories: Fetish, Shemales  |  Views: 3000  |  
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My story

I learned sex from one we say it colloquially Mpsbs debut was his home and I am 17 drink with lawn and watched movies WRX and I Anal grandfather everything a chance to see before me sex if Astoyt touching Tiza sucking Ziyi and Hoenzel without Shi Sohratna lasted more than ten years and evenings to Matnads Evening with sex third in his drink and cannabis Ikhalik like yogurt insanely third sex sucks his uniform, which sucks Ziyi and finger Boukrgi stir with desire and I Ziyi related and Khrgi p*******es grabbing Me caught Ziyi and entered the third sex Mkute large and soft and is itching to Khrg... Continue»
Posted by sbiknet 9 days ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 945  |  
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Transgender dating advice

13 RULES FOR DATING A TRANSGENDER WOMAN
Greetings, Ariscestocrats!
How are your dating lives? Any single transgender women out there? Not too many, eh? Well, I’ll attest to that being the reason I keep running into the same type of guy. He’s Mr. Uninformed, Mr. Inexperienced, and he has a million questions, none of which have anything to do with who you are, but “what” you are. And it’s not that these men don’t mean well, it’s just that they’re hurting their chances by remaining ignorant to a person that they’re clearly attracted to.
So, if you’re attracted to transgender women, here are a ... Continue»
Posted by holdatduck 9 days ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 2128  |  
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Completely Fooled

I could not have expected the encounter I had the other night. Having recently separated from my wife a buddy and I went out to a local pub for a few beers. While we were sitting at the bar deciding what beer to try next a very hot redhead comes over and sits next to me. We exchange hellos introduce ourselves. Soon begin to talk about the different complexities of the beers we are tasting. She is so sexy with small b cups and a perfect mouth. After a few beers my buddy decides to take off leaving Veronica and I to get ourselves. She is just a darling; her smile, her laugh, her sensual demeanor... Continue»
Posted by IndieMe 10 days ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 4237  |  
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After School Dick-tention

I was late for class. Again. I slowly opened the door to my classroom, hoping Ms. Peterson was absent. Just as I managed to open the door enough to peer inside the class, I saw her. She had her back to me, as she was writing down notes for the students to copy, on the blackboard. I couldn't help but admire her form. This was her first year teaching high school history, and she had no shortage of teenage boy admirers. She was tall, I don't know how tall she was bare foot, but in heels (which she always wore) she was taller than most in the school; faculty or student. If I had to guess, I would... Continue»
Posted by SlaveX 10 days ago  |  Categories: Anal, First Time, Shemales  |  Views: 7074  |  
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school teen gay crossdresser first time sex

A young cross dresser's first gay experience
I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my new red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest for me......they were wrong.

It had been a great afternoon jacking off in my new bra and panties and watching my first porno when it happened, I saw the most beautiful thing ever, Peter north titty fucking a hot blonde and cuming all over her face. I w... Continue»
Posted by allisontranny 10 days ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3948  |  
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