Sort by
Relevancy

Free Stories

100%
Aunt Susie's Training Part 4
My Aunt Susie grabbed my hand as I stood in my towel and made me sit down at her 💄 makeup table. I basically had no facial hair so the foundation was applied all over very easily. Next she started doing my eyes with a purple mauve shade of eyeshadow. She put on eyeliner and then mascara, then blus... Read full Story
BITCHGURLvr 2024-06-30 6,120 Lingerie sissy Cigarettes
87%
LADY SUKI
It was my best friend who dragged to this little club downtown promising something I had never seen before. It turned out to be a little strip club. We found a seat right in front of the stage and we watched strippers of various shapes, sizes, and ages perform with a bored mechincalness. "And ... Read full Story
bigtranslover 2013-12-13 8,895 first time shemales taboo
100%
A New Me...
Flash back 10 years when I had just turned 18 years old and had just been accepted into the University of Vermont. I was ecstatic because this was my reach school (I wasn't all that smart book wise) and it was the school that my sister Elizabeth (20, a junior) was already attending. My sister and... Read full Story
shemale lover 2012-04-14 5,437 Masturbation Fetish crossdressing
60%
Brotherly Love, Sisterly Love Chapter 2
"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... Read full Story
shemale lover 2012-09-28 6,757 Cumshot Fetish oral sex cum swallowing
92%
My Dream pt 3
Our first invitation arrived at the end of September. Sydney spotted it first and tossed it into the trash with out looking at it. She didn't tell me what it was and I didn't bother asking. The next invitation arrived two weeks later. This one Sydney opened and after reading it she passed ... Read full Story
Sydney Sun Min 2018-01-04 16,709 Group Sex Shemale Fucks Guy Shemale and Girl Sex Toys
100%
MISTRESS'S TERROR
The night had ended EXTREMELY PLEASUREABLE with BILLY, RYAN & PETER in a literal BANG and I was HAPPY. Now that BITCH I were married with our diamond 2 carat engagement rings and diamond wedding bands we were LESBIAN LOVERS. We were perfect together, Aunt Susie had groomed me into a SHEMALE DOMINATR... Read full Story
BITCHGURLvr 2024-07-01 5,590 cock transsexuals smoking cigarette
100%
Rachel and Chris
Part 1 : Rachel and the Ring Yesterday was clear with a light but chilling winter wind present to remind all that the bit of warmth in the sun would only last a couple of hours at best. I struggled between sweating and freezing as I worked to remove the winter street grime from my roadster. Top ... Read full Story
shemale lover 2012-04-10 4,742 Cumshot oral sex Sex Toys
100%
Bend That Gender
Shannon's Shocking Discovery Shannon leaned against Marilyn. She was definitely light-headed from her last drink. Marilyn's hand resting on her left hip pulled her closer, a move at once comforting and unsettling. She slid her arm around her new friend's waist, resting her head on the silk covere... Read full Story
shemale lover 2012-04-27 7,119 orgasm oral sex cum swallowing
58%
My real story
I couldn't believe it. Here I was in bed with an older man – and one that I most wanted as he lay there sated by my ministrations to him. It had all started two weeks earlier when I had posted an ad on Craigslist. Up until this particular posting I had always been pretty bland..."Willi... Read full Story
shemale lover 2012-06-10 6,486 hardcore Cumshot bdsm oral sex
100%
Angel Chapter 6
This is an entry in the Literotica Winter Holiday Contest, and is part of an ongoing series on the life of Angel Jones, a beautiful young T-girl in London. For more detailed information on her and on the other characters who appear in this story, please see previous episodes. Angel Jones was uns... Read full Story
shemale lover 2012-12-01 4,393 Cumshot oral tgirl
45%
Shemale Prostate Orgasmic Bliss!!!!
if she wanted breasts." "Oh no. That's the amazing part. The more I dressed him the more feminine he became. By now I'd moved him her and her clothes into the other bedroom. She wasn't happy with that but we came to an agreement; I'd milk her once a week and she... Read full Story
ProstateMilker 2015-05-01 14,047 Masturbation cum orgasm cumshots prostate
100%
A Tranny Whores Tale
Ok, so I love tgirls. Absolutely adore them. I've had many experiences at this point, but want to share one. I looked around in the local paper and found this one TS escort. It was early morning (about 5am) and I went to see her. Even though I have had experiences, I get enthralled with nerves and e... Read full Story
shemale lover 2011-10-19 3,982 first time asshole oral tgirl
50%
The Greatest Lie Part 1
The greatest lie that they tell you is that what happens in high school doesn't really matter: that life begins in college. I pretended to agree, though I never believed it. For as you will see, I am the world's greatest liar. "Take Sadie Hawkins Day, for example," I said to my buddy Qu... Read full Story
shemale lover 2012-01-18 7,077 taboo hardcore crossdressing
100%
Carla
I lay on the bed naked. My cock was hard and my hand was down at my ass and my fingers were teasing with my asshole. "I want you in here" I purred And I slid my first finger into my lubricated ass. I gasped and savored the sensation as it slid all the way into me smoothly. My cock tw... Read full Story
shemale lover 2012-03-07 6,964 Blowjob fuck
100%
Carla Chapter 3
So, I reflected, I had quite a day ahead of me. Initially excitement coursed through me as I contemplated the evening to come, and the scope to explore the new extensions to my sexuality. I vividly recalled some moments of the time I had already spent with Carla, particularly it seemed, when I felt ... Read full Story
shemale lover 2012-03-07 3,964 Creampie deepthroating stroking
100%
Fender Bender Chapter 6
My name is Robert, but when I am dressed I call myself Vicki. I am 5'9" 160 pounds, blonde hair and blue eyes. I had just turned 18. Mom and Curt had been home form their vacation for almost a week and I hated it. Sure I was glad to see my Mom but with them around I had to revert back to bei... Read full Story
shemale lover 2012-07-26 3,481 Cumshot oral sex cum swallowing sissy
50%
Feeling Womanhood Deeply
It seems somehow that my desire for womanhood is the one thing that everyone says I can’t have, but who are they to say why I should feel a certain way or want certain things? I want the very thing that their closed minds crusade against. It seems that the thing that brings me the most joy is the th... Read full Story
Regina10 2021-08-26 2,399
66%
Plant Food
Written by: Slayzer Rewritten by: Hobgoblin ~~~ “Where the hell are you, Terry!?” Rebecca snarled, tirelessly searching for her little brother. Rebecca, a pretty sweet sixteen dressed in casual in khakis and a pink T-shirt, was pissed off. It was Saturday night and she’... Read full Story
BoyVixen 2016-03-26 7,183 asshole cum incest
0%
Looking-Glass Ladyboy
I was taking a walk to stay--all right; I'll admit it--to get in shape, when I saw the "Going Out of Business" sign in the second-hand furniture store a block north of my condo. I wasn't in the market for anything, new or used, but I can't resist a bargain, and what was better for finding ... Read full Story
shemale lover 2011-10-29 7,833 asshole Fetish Ladyboy
100%
Interstate Reas Area Whore
Driving down the interstate the sign said Rest Area one mile. My heart skipped a beat and there was slight stiffing of my male meat in anticipation of events to unfold. This interstate rest area was always packed full of eighteen wheelers as many as forty. Surely one or two of these truck drivers wo... Read full Story
shemale lover 2011-12-27 3,823 shemales oral whore
0%
Black Transsexual Nation
Big black transsexual women are truly beautiful. And the big and sexy bisexual and heterosexual men who love us are truly wonderful. I ought to know, I'm one of these magnificent black transsexual ladies. My name is Amanda Joan Baxter, friends call me A.J. I'm a big and tall, big-breasted, wide-hipp... Read full Story
shemale lover 2012-07-06 4,622 tranny Group Sex cum Ebony oral sex
70%
Sara by Sara
1000 – Sissy Story 29 – Sara by Sara Filed Under: Sara, Sissy Story by Anna Malice — 3 CommentsFebruary 26, 2012 4.00 avg. rating (81% score) - 3 votes Post number #1.000 I never thought to reach this moment.. in truth i always thought to cancel this blog.. a lot of time before of this.... Read full Story
saralovescd 2017-05-02 5,128 first time crossdressing college