Free Shemale Stories

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 more

shemale lover October 29, 2011 0%

fuck by my best friend's family

= Part 1. Alice's father = My name is Onikky 28-year-old Shemale from ASIAN, this story only shares the first experience of making love. The story begins when I first moved to a big city, looking for a new atmosphere, I don't have a place to live that I know is only my friend's name Alice who ... read more

Onikky June 25, 2019 80%

Uncle sweet Lover

Uncle Barney called me this morning and wanted me to keep my evening free. He wanted to meet me at the motel with a surprise for me. I was so excited and could hardly wait. I had to decide on something to wear, but when I thought about it, I realized that I wanted to wear something special. He would... read more

Regina10 February 19, 2024 100%

A LadyBoy For My Wife

I have been happily married to my sexy Thai wife Lisa for three years now. My wife is Thai is petite (5'1") with a stunning figure, a tight ass and long waist length black hair. We had met in a bar in Thailand and subsequently we were married back here in the UK. She was very loving with m... read more

shemale lover June 23, 2012 81%

Thai Ladyboy Interview

An Afternoon With Some Thai Ladyboys I spent this afternoon with 6 Thai ladyboys. No, don't go thinking that I tried them out. I didn't. I spent a few hours chatting with them, finding about them, trying to understand what makes them tick and learning about their experiences and the guys who util... read more

shemale lover August 11, 2012 71%

intimate Cousins

My favorite cousin and first lover, Billy, was just released from prison and I was anxious to see him. I am ecstatic that he is out, and I am thinking about all the past fun we had as I prepare to revisit those good times. Tommy knows all about my relationship with Billy and he understands my need t... read more

Regina10 May 13, 2022 80%

Masturbation fantasies 2: Looking for Amanda

Previously: William, a young lawyer who has no luck with women, decide he needs some relief from a live girl. Scared of going with a prostitute, he decides to try out a peep show first. Without knowing that the stripper he chose is kind of special, he ends up in a show with a shemale called Amanda w... read more

ThatEroticWriter July 24, 2019 100%

Hung Trans Lesbians Fuck Two Ladyboys

Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... read more

darrell January 3, 2022 100%

Masturbation fantasies: Amanda, queen of the peep show

A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... read more

ThatEroticWriter July 24, 2019 91%

Ladyboy dominatrix

If you read my other stories you know I'm intersexed and I was a ladyboy prostitute when I was um, very young. I don't condone such activities. They were sick perverts who used me. True I got a lot of money and expensive gifts but that doesn't make it right. They should all be castrated. Th... read more

shemale lover October 15, 2012 66%

Catching up with the biggest cock

I have recently written with an account from my diary about the biggest cock that I’ve ever seen and someone saw the experience and wanted to know more as I had said that I met him a few times. So, I can bring that right up to date now because I have recently been to see him again. But let me go bac... read more

lkusex June 3, 2021 100%

Becoming Alanna Part 2

Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work wit... read more

shemale lover July 12, 2012 80%

K*dnapped & R*ped

"You're nothing but a tease, a flirt, you just like to play around and lead guys on," someone messaged me on the swinger site I'm on called AdultFriendFinder. "No," I replied, "I have actually hooked up with guys I met here, I am just very busy." And that is the truth. I work a full-time job and ... read more

Chrissy Tunnell February 2, 2022 100%

Caught in the act...

One summer, my cousin Nancy came to stay with us for a while, as her parents had gone away on a cruise trip. At 18 years old, she was a couple of years older than me and in the full bloom of her young womanhood, so to speak. She knew it, too, and it was obvious that she had no problem at all in pull... read more

caroletv31 April 23, 2018 92%

Shemale fucks guy - My gf fucks my slutty ass.

I have a shemale girlfriend & we both are in a relationship. One day, I decide to give her a visit. I'm 5'7 guy & she's 6 feet. That makes her tall & intimidating & whenever we meet, it's me who become her gf. I visit her, she takes me in. SHe pulls me towards her while giving me a deep kiss. I ... read more

glodobox December 4, 2020 97%

The Day I Went SheCock Crazy

I summed up courage to meet up with my old shemale flame Fransicca (she is a Malaysian but living in indonesia) ... messaged her, she sounded excited and asked if i minded her friend joining us. 'Why not' i said. It was settled. we booked a villa for the next day. I checked in early. cleaned up ... read more

Sara Banks April 26, 2021 100%

Hot Slutty Sissy

Hello, It’s me, and. I am about to make a big decision and right now I am dedicated to my fantasy. I got a call today from one of my ex boyfriends. I got so horny when I heard his voice that my nipples turn to steel. My titties seem to respond to the sound of his vibrating baritone. I couldn’t refu... read more

Regina10 August 14, 2020 91%

Sissy Slut Reunion

Rob had moved back to town and called me. He had just moved into his new place and he wanted me to come by and talk. I knew what he really wanted from the tone of his voice, because I wanted it too. He said he had been thinking and dreamed about me the whole time he was away. My spirits lifted and ... read more

Regina10 September 14, 2020 100%

MY Party Favor Fantasy

My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... read more

pennypenny January 8, 2019 92%

美娇酱幻想系列一

正常的青壮年男子,三天左右就可以排出高浓度的大量浊精,大部分人选择插入女人的毛穴肉洞达到排精,而我雌雄同体人妖享受肛门被插入高潮同时排精,双重享受,女人化妆,涂指甲是为了取悦男人,我浓妆艳抹,红艳艳的脚趾甲让男人流口水,而我比女人更浪,更知道怎么让男人舒服,男人喜欢玩妖艳女人,雪白的玉脚让他吸吮。淫荡的艳舞后舔弄骚臭的阳具,卵蛋,屁眼,龟头冠状沟系带用舌头敲击,舌尖挑弄,马眼流出汁水就吸吮干净,不时用舌尖顶马眼,双手拨弄男人的奶头,爽的上天。 我疯狂的变装持续了11年,从最初的偷母亲奶罩内裤穿身上自慰,到如今……听着嗨曲扭动,甩着没毛的小鸡巴,扭曲红色脚趾,戴着铁链,脚链手铐口枷一次次的灌肠... read more

Bluesyangiip May 6, 2019 100%