AskJolene - the ultimate porn search engine

Found 190 results on 23 sites by 23 authors for genderbending, page 1
Bright
A Good First Time (part 1)See all parts
2 years ago - 1,100 words -

First I would like to tell you Im years old and never had a gay experience, until now. It was a Saturday night, me and my brother were round the local town, after a few too many beers my brother met a bird so I decided to head home, as it was only pm I thought I would have one more beer before finally going home. I ordered my beer and stood at the bar and had a look around to see who was in, they were about people in, but one blond hair girl caught my eye, she was a slim and lithe object,

By: shemalefan
Tags: crossdressing, first time, gay, genderbending, shemale
A Slut Is Born
2 years ago - 1,100 words -

I cant believe it. Ive been Sarahs roommate for months and never, for one moment, suspected anything different about her. She is the prettiest, sexiest, well-built girl in our dorm. Some things were a little strange with her now that I think about it. Like she always wears skirts, never jeans or slacks. I just thought she liked to show off her long, tanned legs.

By: catcam69
Tags: cross dressing, genderbending, shemales, trannys, transexuals, transgender
Caught In My Girlfriends Lingerie By Her Friend And Gay Male Friend
6 months ago - 1,000 words -

My girlfriend lives alone so whenever im there alone while shes out clubbing or whatever i always take the opportunity to go through all her sexy clothes and lingerie and dress up like the slut that i crave to be. I undressed and put on a pair of white fishnet stockings, a black thong mini skirt, black and white see through top and a sexy pair of silver high heels. I set my camera up at the end of the bed and set it record myself in various poses. after about - mins of this i heard the front door unlock and someone

By: sissy_slut
Tags: anal, crossdressing, genderbending, humiliation, lingerie, slut
The Numbers Game (part 1)See all parts
1 year ago - 1,600 words -

This story could cost me my livelihood, my position in the community, my respect and my own sense of self worth but after many months of enjoying the stories published through Literotica I have decided, against my better judgment, to share a story with you. So here goes. My name is Jason Macquarie and Im . Up until my nineteenth birthday I seemed to have a bright academic future ahead of me for I was unusually gifted in Mathematics and Music. It wasnt to be. I had been dating this terrific girl known as Beverley whilst studying for my A-Levels and thought Id found

By: Dazman
Tags: genderbending, group sex, interracial
HOUSTON Street
1 year ago - 1,900 words -

Dont ever think cause he or she your family that he or she aint gonna trip on you... Bianca couldnt stop fantasizing about her large ass she was going to purchase. See in Houston Streets to be a hot girl, you had to have a large booty. The Ballers and big shots didnt want a women with a flat butt to walk around the streets with. Of course they would have sex with them, and pamper them with jewelry but never would they claim them as a girl friend, or wife. That was just kosher. Finally she had the money to get implants in her flat, muscular booty that would make all the guys

By: bobbyfriend2008
Tags: genderbending
An Unexpected Change TG
2 years ago - 1,600 words -

My Mother had always told me to take my vitamins, which I did. My father had run off and it had always been just me and my mother. I helped her with the laundry and during that chore noticed that her clothes were different than my blue jeans and T-shirts. For some reason I lingered over her clothes and marveled at the difference. They looked and felt so nice and were so soft.

By: catcam69
Tags: genderbending, shemale, tranny, transexual, transgender, transvestite
Dressed In Panties And A Skirt Not Jeans And A T-shirt
1 year ago - 1,400 words -

It seems to me that most guys that screw my bottom typically have me in a position that keeps my cock and balls out of sight. I am always at least at first wearing womans clothing. Bra, panties, hose, slip then a dress or a skirt with a blouse or a top. On my stomach and or on all fours they get to look at my bra strap and or my bra strap through my blouse and or dress.

By: nancecagleman
Tags: anal sex, cross dressing sex, gay sex, genderbending, oral sex, sumbissive bottom
Truck Stop
1 year ago - 1,900 words -

John left the truck after he fucked me. His friend Mike was coming to be with me. I put my clothes back on and I stuffed a cloth between my cheeks to catch semen that was going to leak out of my bottom. Just as I finished putting the cloth in place between my cheeks all of the semen came out right away. The next five minutes I spent cleaning myself. Then I took my time and squeezed lubrication into my bottom. The liquid felt soothing as the coolness shot deep inside me.

By: nancecagleman
Tags: cross dressing, genderbending, ladyboys, male anal, male oral, transvestite
The Training Of Julie
2 years ago - 1,700 words -

The story of the successul aiteration of a good looking youn man into a stunning, talented, ultra feminine boygirl John was about to learn obedience in the strietbatt sense of the word. his whole life style was about to be changed, The rather alightly built, pretty boy of was to become Julie, a boygirl, changed mentally and physically to perform as a girl, It all started when he was approached one day by a rather captivating young lady who having Introduced herself quickly won him over to her confidence. They subsequently had several dates and wasnt he falling in love with Carol? One

By: catcam69
Tags: cross dressing, genderbending, shemale, sissyboy, transformation, transgender
Switched Roles
9 months ago - 2,300 words -

As I entered the room, I was pleased to see my expectations unfold before me. My beautiful male sub, Marcus, on his knees with his head bowed. I walked over to him and laid my hand on his head. Did you accomplish all of your tasks? I asked. I knew he had but I wanted to hear his answer. You know I did madam. I did everything you asked of me. He said humbly. Since you have been well behaved, I have a treat for you.

By: darkheart69
Tags: anal, gay, genderbending, group sex
GirlFriend Videos
Meet the easiest sluts
on this planet, all fuckable!
rawgfs.com

SEEKBANG.COM
Find a Slut. Email her.
Fuck her now!
www.seekbang.com