Shemales Porn Stories
Page 81

First Night Out as a Sissy Pt 2 (By Crystal_ed)

So picking up where I had left off from my last published story…. I had just ventured out for the first time as sissy, determined to find a man. I went to a local sports bar dressed in in my tightest jeans and favorite panties and teased a group of guys. Was able to get one of them into my car for my first blow job ever and after swallowing his enormous load, his friends busted us before I could know the pleasure of him inside of me. After being busted (but feeling sweetly naughty) I was going to call it a night before I realized the bar tender still had my card because I hadn’t closed my tab.... Continue»
Posted by Crystal_ed 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
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Something about Tricia ..



I'm a straight white guy but recently have become curious about Tgirls.
Tgirls are wonderfully sexy and beautiful, but between their legs is a
cock. They say that they are women born into a man's body. I'm not sure
about that, but I keep hearing that they really know how to please a man.

I would never consider being with another guy, but lately I've been
wondering if I could be with a Tgirl and just enjoy their fem side. One
afternoon I browsed the t4m section on CraigsList, looking for a Tgirl I
might be comfortable with.

I saw an ad that caught my interest, "Tgirl seeking ... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  
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One of my true experiences...a unexpected opportun

So I had this wedding to go to, and at the time I was dating a Russian girl named Vicky...it wasn't serious, mostly just a sexual relationship. She was a sexy girl who knew it. At first she didn't want to be my date but after some convincing she agreed to go. The night of the wedding I picked her up at her house. She come out wearing a sexy tight blue roughed mini dress with shiney tan pantyhose, beige high heels...her makeup and hair were perfect, with her amazing tits just teasing you in the tight dress. She looked so amazingly hot.

The wedding was a great time with drinking and dancing.... Continue»
Posted by Sarahaspencd 1 month ago  |  Categories: Shemales  |  
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"The Leatheress", episode102 - The Full

"The Leatheress" - Episode 102
"The Full Monty"


Growing up, I had always been secretly in love with dressing up in women's clothes; the rule always was, the shinier and softer, the better. In my more formative years, this usually meant satin nighties and underwear that I'd "borrowed" from the female members of my f****y, but my lust was always most reserved for leather. Oh, how I used to search out and spend intimate hours with any pics of sexy women in leather that I could find. So naturally when I moved out of home, and had a little more privacy, I wanted to get myself a little collec... Continue»
Posted by SexyLeatheress 1 month ago  |  Categories: Anal, Fetish, Shemales  |  
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My First Threesome

My First Threesome

This is a story which happened to me a few years ago. I was living in London at the time.

I woke one Saturday morning and went through my usual routine - nice bath shave etc. Once I had done my makeup and got dressed (nice lingerie, natural coloured tights, denim skirt and a t-shirt), I sat at the computer to do some work which I had to finish – once the work was done, I had a little surf through the internet and suddenly became really horny. That was it I had to get some cock in me, I went through all the usual sites to get some action – but it wasn’t happening. So I ... Continue»
Posted by imogencole 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
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Dogging Orgy!

This is a little story about my antics when I go Dogging (which I do not do that often, but when I do – I love it).

My first experience of dogging (or cruising as it was then) was back in 1996. After having done all of the usual nonsense, in the bathroom. I picked up my bag of tranny bits, jumped in the car and made my way to a secluded spot to get changed and do my makeup.

Needless to say, I ended up looking like a whore – little black mini dress, black/red matching lingerie, black seamed stockings and black patent heels, with makeup to suit. It wasn’t the intention, but I had limited ... Continue»
Posted by imogencole 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  
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Kitty's cab ride!

I was coming back from a trip and I took a taxi from station to my home. The train was 5 hr late and what was supposed to be a 7 pm arrival was a late arrival at 1 am midnight. I got in the taxi as I noticed the city slowly going to sl**p with roads getting clearer and quieter every minute. I was in the taxi with a man; he was a nice man, maybe thirty years old by looking at him. We made small talk, he moved here with his f****y when he was three years old, he was single, and did not say much. He kept on looking at me and smiling in the rear view mirror, but what could I say? I'm an attractive... Continue»
Posted by CumLovingKitty 28 days ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Successfully squirting like a sissy

After getting home from a long day of work i realized i would be alone for a few hours. I haven't came in a week. An all time record for me! Then i thought about using my toys on my sissy hole. My cock stands up throbbing with agreement. I thought about trying to make my cock squirt just by use of toys sad that i don't have the real thing.

I showered, cleaned out with a douche and stripped naked i sat down in front of my computer my cock rock hard.

Looking on xhamster i found a few sissy trainer compilations and bare-backing vids. The thought of a hard thick cock cumming inside me set me... Continue»
Posted by sub_guy_Sissy 26 days ago  |  Categories: First Time, Masturbation, Shemales  |  
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Playing with myself dressed.

I lived by myself for a while so no problem there, so after showering and shaving my balls and butthole, I set up my dvd player, (yeah it was a while ago), to play Ladyboys in Latex. I retreated to my bedroom to choose an outfit.
Hmmm, I feel naughty and nice tonight, so white, definitely white. I chose a white silky bustier with spaghetti straps and garters, and some brand new thigh high sheer white stockings. After I attached the garters, I pulled the laces on the back as hard as I could and tied them tight. I tucked the laces up so they wouldn't get messed up in my ass.
I looked in the m... Continue»
Posted by badboy4320 25 days ago  |  Categories: Anal, Masturbation, Shemales  |  
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Cockatoo part 10

Cockatoo Part 10

Nikkie Silk

My heart skipped a beat as I heard Shane’s voice from behind me and felt his hand on my shoulder. It couldn't be, I thought, I must be so tired I was hallucinating. Alex said, ‘Hi Shane, glad you could join us.’ Nin looked as if she had seen a ghost, Areeya was smiling in welcome and I felt like I would pass out. The hand moved off my shoulder and Shane’s massive frame came into sight.
‘Hi Nin, Hi Areeya.’ he said, then paused and looked at me, ‘Hi Jamie, how are you? You look gorgeous babe.’
I looked at Shane and then Alex and back at Shane. It was clear ... Continue»
Posted by nikkiesilk 25 days ago  |  Categories: Gay Male, Shemales  |  
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Tits Have Benefits Ch. 03

Shemale - crossdressing – feminization - transfirmation - anal – strapon – oral

Thank you for everybody's support for this story. In this chapter the complex dynamics of a polyamorous relationship including 4 women and a shemale is explored. Andrea becomes gradually and lovingly integrated into this 'f****y' while having the time of her life ...........

After transforming myself into a shemale and returning to claim the love of my life Jane, I was accepted into Jane's loving f****y of lesbian lovers, this despite the initial protestations of Jenny a tall blond bombshell. In fact J... Continue»
Posted by naughty_bi_interest 25 days ago  |  Categories: Anal, Fetish, Shemales  |  
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The civillian

I shadow wrote this story for a friend. The two of us hope you enjoy it.

When I finished high school I spent a few months working, before being drafted. Aside from a short period of training, during the first half of my term I spent most of my time behind a desk. I did spend a day a week doing guard or drill duty, to keep in shape and keep my field skills fresh. When things escalated and another unit was in need of a new sergeant, I was promoted and got reassigned. Still behind a desk, but now assigned to a war zone, I did spend a lot more time in the field. I had to go often to an improvi... Continue»
Posted by GalFa 24 days ago  |  Categories: Anal, First Time, Shemales  |  
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My First Time as Sara... Pt. 01

crossdresser – sissy – virgin – sissy boi – anal – lingerie

I only knew Steve as my landlord. To be exact, Steve was the only son of the two people that owned the small apartment complex I am currently living in as of right now.

My reason for moving here was out of necessity than anything else. Three months prior to moving in the 20 unit complex I lived on the other side of town with my then fiancé Sara. We're both late 20 something k**s that moved in together after collage and while the first couple of years seemed grand, it was bad things that were under brewing in the relation... Continue»
Posted by naughty_bi_interest 24 days ago  |  Categories: Anal, First Time, Shemales  |  
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My First Time as Sara... Pt. 02

sissy boi – crossdresser – tranny – lingerie – virgin

I look up at Steve and give him a genuine smile. A smile that tells him I want and crave him. In a whirlwind day that started with me buying some girly stuff to enjoy on my day off from work, is now ending with another mans cock in my lipstick covered mouth.

I have his legs open and I'm on my knees. My hands are now running over his muscular and tight legs and my tongue licks his stomach. I have a naked man, average in every single way, except for his very thick, 8 inch cock sitting on my couch and I'm in my black stockings wit... Continue»
Posted by naughty_bi_interest 21 days ago  |  Categories: First Time, Gay Male, Shemales  |  
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Tits Have Benefits Ch. 04

bisexual – lesbian – anal - strapon – cock sucking - feminization – transformation

Thank you for everybody's support for this story. Andrea gets an invite to visit Trish and Sandy in California and the story takes an unexpected turn, although I am guessing that some of you may have figured out what direction things might go. Please note that in the first few paragraphs there is a lot of plot development with no erotic scenes but fear not when the erotic scenes do cum, nothing is held back...

*

After transforming myself into a shemale and returning to claim the love of my life J... Continue»
Posted by naughty_bi_interest 21 days ago  |  Categories: Anal, Fetish, Shemales  |  
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Baltimore glory hole HUUUUUGE black cock

I was in Baltimore on a business trip and, as always when I travel, I extend my trip through the weekend to go to gay bars and more importantly the porn shops with glory holes. I go there for one thing--to suck as many cocks as possible. My preference is almost ANY black man or white fems and TS's.

I took a cab after a gay bellboy at the hotel told me where to go for that reason. The cab dropped me off on a two block strip loaded with the bright lights of all-night porno shops. I talked to a few black teens that were hanging around and asked where I would find the most black men to go... Continue»
Posted by reesielover 21 days ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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1st time-VERY young black TS hooker

A few years ago I was driving to work just before 8:00 A.M. I was stopped at a light while crossing a small bridge and saw a beautiful young black woman (so I thought) in a sundress. I had my windows down and happened to make eye contact with her. She came right out and asked me for a ride about a mile in the opposite direction I was going. Even though I am about as gay as a man can get, as she was so young and innocent looking I said ok. She got in my car and I headed where she directed me. The ride took about 10 minutes as we hit several red lights. She was kind of elusive to my casual quest... Continue»
Posted by reesielover 20 days ago  |  Categories: First Time, Interracial Sex, Shemales  |  
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The Making of a Sissy (Part 6: Broken)

The sound of rain beads beating against my window like a drum filled my bedroom as I got up out of the bed to make my way into the bathroom. It was the beginning of another hot, wet, and steamy summer day. This summer had felt like it was continuing on forever and also forever changing my life, but we had reached July and I didn't have much more time before I would be starting college. I began to draw myself a warm bath then slid my shorts and panties off around my hips and down to my feet. My freshly painted toenails shined through the lacy bikini as I kicked them into my hamper. As I pu... Continue»
Posted by briantid8 20 days ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Jacki's Journey into Sissyhood Pt. 02

sissy – pussy – oral – strap on – anal – plug - cum – mistress

I awoke as sunlight began to creep into my bedroom. I might have thought last night was a dream if it wasn't for the large hairy arm d****d across my shoulders and the large cock poking at my backside. I tried to slowly slide out from under Steve's arm, only to have him pull me closer and kiss my shoulder. "Good morning Jacki," Steve said sl**pily as he yawned.

I took my free hand and grasped his erection, and laughed," It seems this guy has been up for a while now."

He chuckled back, "Yeah, well who can blame him h... Continue»
Posted by naughty_bi_interest 20 days ago  |  Categories: Anal, Fetish, Shemales  |  
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Gangbang at Ricks part 5

Gangbang at Ricks part5

All of us left when we got up, I counted Heads (cock heads lol) still 8 nice size, and Kim n Me us Sissy's woke up first, i told her meet me in the shower, we can have fun cleaning each other for the rest of the day. trying not to wake them all up, but i had a big problem Nicks big soft cock head was still in me all night, it's going to get messy, his and Don's loads in my belly, Kim grab that big butt plug try to pull nick out of me, she knew pulled it did a good job pluging back up. she giggled ... Continue»
Posted by mrheat22 19 days ago  |  Categories: Anal, Gay Male, Shemales  |  
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