1. My wife introduces me to submission and cuckoldry.

    5/23/2018: It took me a while to come clean to my wife about my time before we met. In that time i had been a submissive to a Professional Mistress in the Midlands and it was from her that i developed an interest in both servitude and crossdressing. Mistress/Madam had always insisted that i should be dressed as a woman whenever i was in her presence. After Mistress/Madam and i had gone our separate ways after many years of being together i had to admit to feeling a little alone and deserted and with no direction in my life. i had several relationships and none of them had any idea about what i had been read Sex Story
    Categories: BDSM, Mature, Trans, Author: oldognewtrix, Source: xHamster
  2. My First Time!

    5/21/2018: “Hey are you on your way?” “Yeah ill be there in 20” “Nice just message me when you get here.” I’m 17 years old in high school and I had no idea what I was doing. I had matched this hot nerdy sexy guy on tinder and we hit it off and he invited me over to his place. But before I begin this sexy scene let me give you all some descriptions. I call myself Elaina and I am a cross dresser and I am read Sex Story
    Categories: True Story, Anal, Asian, Oral Sex / Blowjob, Teen, Consensual Sex, First Time, Gay, Teen, Trans, Trans, Trans, Author: Eonasha, Source: sexstories.com
  3. The Adventures of Georgina part 1 - First Time

    5/19/2018: These are the real life stories of a straight guy who becomes a sissy slut. Names and places have been changed to protect the not-so innocent! Enjoy! Ok, who am I? My name's George and I am a man in his early forties, living in a large town in rural England. I'm pretty normal really. Physically I am slim and naturally thin-boned, 5'8" tall and 140 Lbs. My cock is what you would call a "grower" rather than a "shower". When cold it almost disappears due to shrinkage and when fully aroused, might make five and a half inches. I'm told that's average, but I think I'm on the small side! I read Sex Story
    Categories: Fetish, First Time, Trans, Author: 5155y, Source: xHamster
  4. Long Tongues

    5/18/2018: Long Tongues Hank moves in: I was being transferred by my company from state to state on the average of once every two years. When I moved into a rental home in Southern California, everything seemed normal at first. My neighbors, the Smiths, had a buffet lunch poolside as a “welcome to the neighborhood” party for me. That was when I met their twin daughters. Average girls, I remember thinking. Boy was I wrong. Paige and Phoebe were both young slender teens with almost non-existent curves. They both wore braces and glasses. They were blondes with lovely tans. Their bright blue ey read Sex Story
    Categories: First Time, Trans, Taboo, Author: tankengine123, Source: xHamster
  5. Cum with Big Momma

    5/17/2018: I was having a hard time fulfilling my favorite fantasy. I wanted to be fucked by a shemale. I'm not a total bottom but I definitely liked cock in my ass. I cruised through craigslist but had disappointing results. Most of the hottest gurls in the t4m section were hookers, and crossdressers in the m4m section were all bottom. I finally found an add for a chubby black shemale who called herself Big Momma. The pics in the add showed a huge fat bbw with big tits, big ass, and the last pic showed a big hard black cock. I was a little intimidated by the picture but she looked like exactly what I w read Sex Story
    Categories: Anal, Interracial Sex, Trans, Author: badboy4320, Source: xHamster
  6. Norman and Anastasia Part 2.

    5/14/2018: Luke and I follow Anastasia up the stairs. Her wrap round dress is tight across her big firm arse. Luke looks over his shoulder at me and grins. His eyes are level with that big swaying arse. She reaches the landing and opens the door to the bedroom. She hesitates a moment before walking in. She climbs onto the bed on all fours and Luke climbs up behind her. Her grabs the material of her dress and throws it over her back, exposing her arse God!! Where did Norman find her. On all fours behind her he buries his face into her crack and licks all the way up it. Reaching between her thighs he grabs read Sex Story
    Categories: Anal, Gay, Trans, Author: dasilva1672, Source: xHamster
  7. I came so hard with a Sissy

    5/12/2018: The day that I would meet Dominique had finally come. My God I was so nervous but yet so excited what a strange mix of feelings. I finally arrived at her house and barely found the courage to push the door bell. I pushed the button, I then almost immediately I heard here delightful southern accented voice "Just a Minute" Dominique answered the door with a large sweet smile, "Finally Michael we get to meet" She was wearing a beautiful black silk rope and her hot black high heels. Before I could say a word , she gave me a warm friendly hug and a gentle kiss on my cheek as she ushered me inside read Sex Story
    Categories: Fetish, Trans, Author: Lossst, Source: xHamster
  8. Tranny orgy

    5/11/2018: You can live with someone and never really know them. I was running a car wash in West Palm beach and every day I would take lunch at a cafe down the Blvd. The food was good, and cheap and I had the hots for Debbie, this built to the hilt redhead chick working there. She wasn't any great beauty but she had a body to die for. 36 DD tits. big hips and thick legs. Just my type. After a couple weeks I got the nerve to invite her to TGI Fridays for some drinks. After a few, she started talking about her past. She was on parole from Ohio for cocaine trafficking. I found that interesting because a read Sex Story
    Categories: Group Sex, Interracial Sex, Trans, Author: kwhagie, Source: xHamster
  9. Kolkata Business Trip Part I

    5/9/2018: As you all know and those who dont i am from somewhere in north india i am tall fair smooth and i love to crossdress when alone. I am bisexual and when alone ( usually on my work trips) i dress in female lingerie and make love to a male as a woman. So as it happened last monday i was called for some meetings over the next 3 days in kolkata(kol) and i took a flight and reached there around noon. I took a cab and reached my hotel in park Salt Lake city area. It was a nice hotel with cozy rooms. I had a shower and ordered food. I had my food and dozed off. I woke up around 4 pm and was browsi read Sex Story
    Categories: Anal, First Time, Trans, Author: hornyboyind, Source: xHamster
  10. A Very New Year

    5/7/2018: Sometimes things happen unexpectedly. Those words describe my entire New Year's Eve. My night started with me downtown. Now ordinarily I wouldn't step foot downtown on New Year's Eve if I could at all avoid it. The place becomes a zoo of d***ken bafoons and desperate revelers. But through an unfortunate series of events I found myself behind virtual enemies lines too late into the day this New Year's Eve. Many of the roads had already been blocked off and those that weren't were highly congested with the other like minded people that would give anything to be out of here before things got too read Sex Story
    Categories: First Time, Trans, Author: rhyze, Source: xHamster
  11. 1994 New Year's (Keela)

    5/7/2018: This a story, and no more than that! I could not go home for the winter break due to tons of things to do about my college thesis, so I stayed in my adopted town in the Pacific North west, so Keela my running teammate. She had the same problem, she was writing her thesis as well. Christmas went by and I spent it in my apartment by myself and tons of papers everywhere, I had chinesse take out. New Year's eve came along and I decided to call my friend to see what she was planing to do. It was a lot of snow on the ground and I really did not want to go downtown to cele read Sex Story
    Categories: First Time, Lesbian Sex, Trans, Author: ilialenyc, Source: xHamster
  12. The Knight and the Acolyte Book 3, Chapter 3: Stolen Virginity

    5/4/2018: The Knight and the Acolyte Book Three: Barbaric Passion Chapter Three: Stolen Virginity By mypenname3000 Copyright 2016 Acolyte Sophia – The Village of Asheth, The Magery of Thosi Angela's cock entered my pussy. I gasped as the intense pleasure rushed through my body. The purity that connected me to my Goddess severed. But I didn't care. The cock felt so good as Angela rammed her hips forward read Sex Story
    Categories: Fantasy, Anal, Exhibitionism, Female exhibitionist, Female solo, Lesbian, Group Sex, Lactation, Straight Sex, Oral Sex / Blowjob, Toys, Trans, First Time, Author: mypenname3000, Source: sexstories.com