Free Shemale Stories

Bi male and anal sex

Thru out my adult sex life I have always enjoyed having my ass teased and played with. Then I started dating a woman whom loved to tease a mans ass with her fingers, yes fingers where she quickly got me use to taking 2 of her fingers. Then one night things changed. After a hot night of wild sex,... read more

shemale lover October 10, 2012 100%

Anal Pleasure

Hi, I am nick i'm 21 and I lovee trannies. I have been jerking off to shemales for quite some time now, at least a couple years and I always get really turned on thinking about fucking them. However, for some time now I've been feeling a little curious of how it would feel like to get fuck... read more

nick tamer March 2, 2018 50%

My first anal

This was a couple years ago, but I still remember it very well. I was insanely horny one night so i signed up for a sex dating/chat site. I'm siting around, rejecting chat invites from guys, thinking I'd never want a cock. After a while, I decided to try chatting up a guy, see what kind of stuff ... read more

shemale lover February 24, 2012 100%

My first time with a guy

MY FIRST TIME WITH A GUY Another true story it’s kind of long but I think you will enjoy it I lived west of Lake Worth Florida. At that time we were surrounded by 1500 Acres of woods. There were 10 of us and we all had dirt bikes and would go out riding all the time.. On Saturdays we had a game ... read more

Stephanie101 April 26, 2024 77%

Freak House Superstar Come Fest

Kiki and Ty Blaze were doing their thing. They were living on their love and passion, literally. The couple had taken their love, passion and desire to please one another and turned it into their livelihood. They had become stars in the world of underground porn. Their production studio, Nasty Nigga... read more

shemale lover February 1, 2012 40%

Teacher Student Confidentiality

It was raining cats and dogs outside as Ms. Catherine Walker (Cat by her friends) graded her Accelerated Integrated Geometry test scores. Her was long and flowing and her sweater was purposely pulled low to embarrass the male teachers with her cleavage. Her cock twitched as she shifted her leg to a ... read more

shemale lover February 11, 2012 83%

My wife dressed me and used me like a slut

I think you are about ready my wife “Jen” exclaimed and she rotated me towards the mirror. My cock was already rock hard and sticky soaking the silky panties as I looked at my reflection. I gazed at my blonde shoulder length wig bounded into two braided pig tails, my face heavily coated ... read more

shemale lover February 14, 2012 75%

My First and Last Girlfriend

Zeta was my first girlfriend. Together we discovered how to make love and how to enjoy good sex! She was quite shy, and it took me 6 months before I managed to push my dick up her little virgin slit, and make her a woman. She was 16 at that time and I was 19. After her defloration, she became ... read more

shemale lover September 28, 2011 90%

Seduced Willingly

Finally, I moved to a city that was exciting, Miami. I moved to Miami looking for something new and adventurous. I grew up in very conservative town where nothing exciting went on. In Miami I found different languages, gay people, different ethnic persons, art, and culture. However, my job keeps me ... read more

shemale lover April 16, 2012 92%

Seduced Willingly Part 1

Finally, I moved to a city that was exciting, Miami. I moved to Miami looking for something new and adventurous. I grew up in very conservative town where nothing exciting went on. In Miami I found different languages, gay people, different ethnic persons, art, and culture. However, my job keeps me ... read more

shemale lover August 31, 2011 85%

Black Transsexuals Rock

Yvette Seraphim is the name. I'm a big and tall, dark-skinned and big-bottomed young Black woman of Haitian descent living in the City of Ottawa, Province of Ontario. People often say I resemble Tennis Champion Serena Williams, only taller and curvier, with more booty. I take that as a compliment. I... read more

shemale lover July 17, 2012 50%

My very first experience with my classmate

He was amused by the sight...of me in lingerie..standing on the porch,it was obvious he was in a shock (or state of extacy?) and couldn't take his sparkling blue eyes off my firm body inside the dress...he closed the door behind,like he was worrying if someone could see us ..I don't know why but i f... read more

shemale lover October 1, 2012 88%

Ad trap

I saw their ad at the site: “Couple looking for a bisexual guy.” I decided to call them I knew I had to hurry, there were always many people ready to try, I wanted to be the first. When I dialed the number I heard a nice voice, it was a man, he sounded like a beefy man. He turned out to ... read more

shemale lover May 19, 2014 59%

Neighborhood Restaurant Surprise - Kimi

I - The Meeting In the neighborhood restaurant I frequented weeknights after work, I had developed a friendly relationship with several of the college kids who worked as servers. Always having been attracted to the most feminine and petite of girls, dark, almond shaped eyes being a super plus, I ... read more

shemale lover April 11, 2012 100%

First time and what great fun

My name is Jakub, or Jake as my friends call me. At the time this little adventure took place, I was 20 years old and I guess I was a pretty lonely guy. Overall, I am a pretty average dude: 6 feet tall, slim body and average looks, the only thing about me that’s a bit different than most peopl... read more

shemale lover April 16, 2012 100%

Office Policy

“Ok ladies and gentleman, please put your hands together for the beautiful and talented Erika!” the DJ’s voice rang out over the thumping alternative beat as the object of my lust strutted to the stage. Erika’s saucy red curls bounced on her head and on her soft porcelain whi... read more

shemale lover August 30, 2012 80%

More Dirty Sex with Tania. Part One Hotel Sex

It took quite some planning, after our last meet in the lay-by, but at long last we had both been able to get away at the same time. We, well actually Tania, had arranged our meet to be at the Premier Inn at Witcombe, just south of Cheltenham and just of the A46. Tania was arriving just after lunch ... read more

shemale lover March 27, 2014 75%

Shock and Awe. Part 2

Carla lay back on the white sheets and said ‘I want you to lick me down there first’ I was a bit shocked to be honest. I mean every guy imagines what it must be like to suck a cock at some point in their lives (and I just had for the first time, it was lovely), but anus licking had ne... read more

shemale lover May 17, 2014 100%

New Leather

I have a super-sexy new coat! It’s black leather, has lacings and D-rings as detail all over it, a high collar, straps to close it in front, and a red lining. It’s very . . . well, it’s like something out of a vampire movie, so maybe it’s a bit much for everyday wear, but I t... read more

shemale lover November 7, 2015 87%

My Window Cleaner

My wife had gone away for a few days, so I decided to indulge in a favourite pastime, which I don't often get chance to do. First I took a long hot bath, and shaved very carefully, removing all my body hair, including my pubes and anal hair. I towelled myself dry, and began to dress. I'd been o... read more

shemale lover August 27, 2011 100%