Sort by
Relevancy

Free Stories

100%
When Finally We Meet
Dear John: This is the last e-mail you will receive from me before we meet. You had read my previous story, "Visit to an adult store," in which I had my first gay experience with a much older and stronger man and was forced to wear a sexy, off-the-shoulder, bare-midriff harem outfit wh... Read full Story
shemale lover 2012-12-07 3,448 anal Crossdresser Cumshot Fetish
100%
Property To Be Pimped
It had been weeks since I'd brought to light my idea of my wife, Suzie, strapping on a big dildo and taking me dressed as Desiree, the Hot to Trot Transvestite. While at first she teased me with possible participation, it never came to be, despite me bringing it up on several occasions. She really d... Read full Story
shemale lover 2013-01-17 7,247 Stockings Crossdresser sucking dildo Interracial
97%
My First Time
This is my first ever story written about my first ever sexual encounter with a transgender woman. I really hope you enjoy and want to leave me some feedback… I have slept with many women in my life. I have been married, had more girlfriends than I can remember, several fuck buddies and far too m... Read full Story
tsJessie 2014-01-20 11,046 first time Crossdresser sex transgender hot
100%
Born to suck
I’m a straight guy who watches to much porn and when I hit my thirty’s regular porn was getting boring. while searching the web I stumbled across some tranny porn, now I always loved blowjob porn it was my favourite but now watching a big dicked tranny getting her cock sucked is my favourite and I ... Read full Story
Beesknees 2018-03-02 6,435 Blowjob blowing
100%
Camming down the rabbit hole Ch3
Slowly stirring from my sleep, I stretched under the covers and a pleasant sensation spread across my torso, remembering what I was wearing when I went to bed I smiled at the caress of the fabric on my skin. It was a strangely comforting feeling, the pressure from the bra, panties and nightie felt l... Read full Story
Dani_does_Dallas 2021-08-18 5,191 Stockings Crossdresser solo Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade
100%
A Win-Win
A Win-Win By Sabrina G. Langton *** Author's Note: Hi, just a quick, crazy story about a wife actively participating in her CrossDresser husbands sex life. Just a bit of fluff, hope YOU like it.) *** We were laying in bed, sex was done, my wife could now relax for the rest of the month ... Read full Story
Brina Giselle 2024-03-31 3,885 anal Stockings Crossdresser Blowjob pantyhose kissing salon
100%
What I dream about
I'm shortly to embark on a trip to amsterdam in the new year and am very excited for one thing in particular, the opportunity to come across a real life shemale! I've been a massive admirer of shemales for a long time now ever since I first saw one. I don't remember exactly how I came across them b... Read full Story
shemale lover 2011-08-11 3,216 asshole licking fingering
100%
Marilyn: Going Your Way
"Oh yes…eat me…ooh yeah…" Marilyn was laying on one side, watching her sister Sharilynn get gently eaten by Kat. Marilyn herself was bottomless, letting her limp dick hang down to recover from soreness. Yes, it was one of those weekend afternoons that stretched into... Read full Story
shemale lover 2011-11-08 3,494 sucking orgasm nipples
91%
Mark's Surprise
Mark had just broken up with his steady girl, Diana 2 weeks before. He was finding it really hard to get over her. They had been dating for almost 2 years, and he was devastated when he caught her in "The Act" with 2 guys from the football team. He saw her car at the hotel, and pulled in t... Read full Story
shemale lover 2011-11-25 3,873 anal Creampie oral
100%
I Call on Jill & Mary
When Jill was born the medical staff looked at the baby's genitals and told the parents "You have a baby boy." The baby was named Jack, after his uncle and spent the next several years as a boy. Jack never got involved in sports with other boys, partly because of his small stature and p... Read full Story
shemale lover 2012-01-17 2,704 shemales hardcore Group Sex
50%
A Night On The Town
The third Friday of every month is my day. This is the one day, or rather night of the month that I truly look forward to. Only twelve times a year, do I allow myself to totally, absolutely indulge myself. To be a slut! A total tramp! To luxuriate, and fulfill my desires that have been pent up insid... Read full Story
shemale lover 2012-02-06 2,773 Fetish nylons shaving
0%
A Long Friday Night
Labor Day weekend was coming up. It is the weekend that I let myself go. On this weekend I do something that I save for most of the year. I just do it for myself. This year I was going to try to get a date with a young lady called “Lee”. Let me tell you something’s about me first. ... Read full Story
shemale lover 2012-03-17 3,672 sucking Asian domination jacking off
100%
Emily and Steve Part 1
As I pulled my cock out of Emily's ass and shot my load onto her flat stomach, where my cum mixed with the load the beautiful blonde cross-dresser had just shot from her throbbing cock a moment before, I thought to myself that work was suddenly going to be a lot more fun. My name is Steve and I w... Read full Story
shemale lover 2012-04-06 3,720 Crossdresser anal sex blonde
72%
Black Man's White Sissy
I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my ... Read full Story
shemale lover 2012-07-03 9,413 Cumshot oral sex sissy
100%
My Dominate Spanish Mistress Parts two and three
I wasn't going to write anymore for this story but i posted the first part of the story on 99chan's elit board which a recommend going to. Maybe with the help of some of you people writing or encouraging more writers on their stories the board might return to its former glory. After all some guy sa... Read full Story
bruceclark 2012-08-24 4,737 anal Latina domination slut feet
80%
Brazilian Heat Chapter 2
The next morning as I awoke I could hear the shower running. I gingerly got up. Moving slowly because my ass felt like it was on fire. He had rutted me good last night. The thought of last nights debauchery brought a spark of hunger to my very core. I walked into the bathroom and watched as he/she w... Read full Story
shemale lover 2012-08-26 3,334 anal Cumshot kissing
100%
Always Be Closing Chapter 3
Hi, my name is Tom Jacobson but you can call me Marcy. I am 23 years old man. I'm 5'9" with light brown hair and a slim build. This is my third story about what happened on my first business trip after my luggage was lost. It all started when my coworker Tina convinced me to wear one of her spa... Read full Story
shemale lover 2012-10-17 3,690 anal sex Cumshot sucking
100%
Angel Chapter 5
On Monday morning, Angel Jones woke up smiling and with a feeling of well-being. She was still feeling the effects of the great sex that she enjoyed Friday night and Saturday morning, and the plaudits of the people at the Friday dance at the Gay, Lesbian, Bisexual and Transgendered Association. She ... Read full Story
shemale lover 2012-12-01 4,454 Cumshot sucking fingering
97%
First Time With A She-male
My First Time with A She-male At that time I was 28 yrs, single as always after my gf of 10 months left me for a better alternative (we are friends till now). One Friday evening i was returning from my work a little high on vodka n some joints. I saw this boutique kinda shop near my locality dis... Read full Story
Lisawantsu7 2014-02-25 9,961 tranny
69%
Motel Blackout
I always enjoy my sales trips. The trips fit into my crossdressing lifestyle and the thrill of being in a different town and different people. After a long day on the road, I had just checked into a motel just about 30-miles outside of Nashville, TN. For my overnight trips, I always bring my spe... Read full Story
browncherrygurl 2017-05-25 18,135 anal Crossdresser ass fucking sissy forced
88%
Popping Lisa's Cherry
The door slammed and Lisa's heart leapt. She was alone, finally alone with all the time in the world to pamper herself. She had hours and hours to look forward to, to be a real lady. It wasn't often that Lisa had such an opportunity, even if she did find herself alone occasionally there was alway... Read full Story
shemale lover 2011-11-04 5,278 asshole orgasm oral sex
100%
She's Not Hazel Part 2
I could not get out of my mind the sight of fucking Maria and she turns out to be a she-male. I was surprised that it didn't matter, I loved her perfect ass and the way my dick felt in it. The sight of her jacking herself off and then cumming on her stomach is etched in my mind and I can't wait to s... Read full Story
shemale lover 2011-11-30 2,726 Cumshot licking sucking
100%
Revenge is Sweet
Henry Stewart was thirty five years old, married to a very attractive woman who'd given him three kids, he owned and ran his own very successful computing company in San Diego, "Stewart Computing", meanwhile he owned a large house in the wealthy small town of River Falls. All in all, Henry... Read full Story
shemale lover 2012-09-01 7,724 Crossdresser Cumshot Masturbation Lingerie heels
83%
Francis Meets a Black Stud Part 4
After I got back to my camper, I packed a bowl and took a few quick hits. I then quickly straightened myself up. My dick was rock hard and I really needed release and desperately wanted to return to my man and worship his cock some more. I needed to cum so bad, but I did not want to until he said th... Read full Story
shemale lover 2012-11-20 3,114 sucking Ebony orgasm