Sort by
Relevancy

Free Stories

50%
a diary piece - my next date
A diary piece - my next date I hadn't forgotten how to please a man and I had decided to be a little whore for him. Yes I enjoyed it very much and wanted to be fucked again the next day. When I start having sex I want it all the time. HiltonP had said he wanted a date again on 21st and 28th ... Read full Story
amberdoll 2020-09-16 2,491 Stockings Small Tits Crossdresser Amateur Bareback blonde Lingerie Homemade
75%
How it began (2/x)
(Part 1: https://www.ashemaletube.com/story/how-it-began-1-x-6645/) ... I felt more and more anxious and nervous the longer I was alone in that bed, unable to move, unable to see what was going on and unable to do anything but wait. After maybe an hour - it might have be... Read full Story
sissylennie 2022-10-03 3,364 Crossdresser threesome domination mistress bound tied up Cuckolding Cuckold Sissy
100%
Dress-Up-Girly Time!
"Let's go, 'Little-Missy,' it's our 'dress-up-girly time.'" Sandy knew better than to argue. Besides he really didn't mind being dressed up as a girl. It was kind of weird at first, when he first started playing 'dress-up-girly time.' His mom had brought home several boxes of clothes that no lo... Read full Story
ALEXEAMES 2024-01-27 5,139 Crossdresser Amateur Lingerie small cock Homemade sissy femboy teen (18+)
100%
The Meeting of Cortney and CiCi p1
Cortney could not keep herself from thinking about the upcoming date with CiCi as she sat in the luxuriant bath water and shaved her legs. She planned to fuck the glam slut whore long and hard. But first, the metamorphosis to turn her into the dome bitch - Cortney. She rose from the bath, patted... Read full Story
shemale lover 2013-04-15 3,468 suck shemale oral Lingerie make up
100%
My story, more or less pt.3
Earlier on, when I was scouring through various drawers and closets for feminine clothes in my home I have stumbled upon two old skipping ropes. "A fun time" I thought to myself, not giving them another look and continuing with my search. Little did I know they would become the backbone of my "sessi... Read full Story
Thigh_High_Boi 2023-01-06 3,437 Stockings Masturbation Fetish Ladyboy Lingerie Homemade pov
77%
Porn site meeting and fucking ;)
We started talking on a site. I knew you were for real when you sent me a message introducing yourself. We only spoke for 2 days before we decided to meet up and I was excited to play with a real little slut. You told me the only things off limit were anal and scat otherwise i could do what I wanted... Read full Story
BalkanLoco91Ri 2019-08-26 4,732 Teen (18+) Amateur Cumshot Masturbation Bareback Blowjob Big Cock Uniform domination Homemade pov Ass to Mouth cum in mouth
100%
The WearFemme
The times between his fantasies have begun to shorten and he knew it wouldn't be long now. One chance glance at an outline in gym shorts as a guys walking in the wind, or seeing a girl with similar features wearing revealing clothing. The thought of it is almost overwhelming now and he has to focus ... Read full Story
Jayde Love 2022-12-01 3,183 Small Tits Crossdresser solo Amateur Outdoor Masturbation Fetish Homemade pov
100%
My story, more or less Pt.1
I always knew I was different. I enjoyed playing with dolls and being around girls, I felt safe and in my place. When I got my first smartphone I have discovered porn, and boy was it an adventure! I have watched every type you can think of, but eventually I settled on shemales, the perfect cross ... Read full Story
Thigh_High_Boi 2022-12-22 4,592 Stockings Cumshot Masturbation Ladyboy Lingerie Homemade pov
81%
My first time getting a big cock in my ass
I got talking with a relatively local guy, much older than us, but had a thick 8.5" uncut cock, which was perfect for what I wanted to watch enter my Mrs. Our messages went something like this... Me "Did you want to meet up first?" Him "If you want" Me "We'll chat about a plan, then I'll... Read full Story
BalkanLoco91Ri 2019-08-26 7,423 Amateur Cumshot Bareback Creampie Blowjob Big Cock Homemade pov Ass to Mouth
100%
Booty call :)
Your cock pounds my ass harder, my cheeks rippling with every deep thrust you give. The sounds of our moans and your balls slapping as you fuck me hard is suddenly broken by the ringing of your phone........... And you wake up. It's 2:30am and I've just finished work. As arranged, I'm giving... Read full Story
BalkanLoco91Ri 2019-08-26 4,985 Teen (18+) Amateur Cumshot Masturbation Bareback Creampie Blowjob Big Cock domination Sex Toys Homemade pov Ass to Mouth cum in mouth
80%
One night Transtand ;)
One Night Transtand By BalkanMan990 Published on Lush Stories on 05 Oct 2019 I had no idea she was a trans.. I didn't stop kissing or fondling her when I found out. I went out for a drink at one of the many bars at Croatia,where my girlfriend Sabina and I were staying.Sabina and I had been drin... Read full Story
BalkanLoco91Ri 2019-10-24 8,671 Small Tits Amateur Cumshot Masturbation Creampie Shemale Fucks Guy Blowjob blonde Lingerie Guy Fucks Shemale Homemade pov cum in mouth
100%
How my date went
There I was on TV with the sound up jus barely enough for my date and I to hear. We had gotten past the introductions at the bar we had jus left & now it seems as if those 4 shots of tequila jus wasn't enough for me to overcome how scared I was. But Alma, my date had run into Nervous Nellies like m... Read full Story
Curious_billy 2022-10-21 5,409 Teen (18+) Amateur Cumshot Masturbation Blowjob Big Cock Lingerie Homemade pov cum in mouth webcams
66%
Awesome day at class =)
Sooo i'm in college. and one of my professors is really hot. he's older but looks like he's in his 30's. anyway, every single day in class i would notice his huge bulge under his pants and just couldn't help but wonder =P so i figured, hey maybe i should start flirting with ... Read full Story
Amanda Lips 2018-03-02 3,318 Teen (18+) Mature Homemade pov Ass to Mouth cum in mouth webcams
83%
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 full Story
shemale lover 2012-02-11 13,735 anal Blowjob black fiction
100%
Camming down the rabbit hole Ch4
It was the morning after the night before, and as I stretched under the bedsheets, a smile spread across my face. Remembering last night’s events, I felt myself stir a little and pressure from the panties I had on adding to the arousal. It has been a while since I had morning wood after a big show, ... Read full Story
Dani_does_Dallas 2021-09-06 3,535 Crossdresser solo Amateur Cumshot Lingerie Sex Toys Homemade pov webcams
100%
Camming down the rabbit hole Ch6
In the morning I decided to give the running a miss and do a long session with the DVD, my legs had become a little sore and tight so some extra stretches and yoga would really help. I once again surprised myself with how much more flexible I had become, the plug still in my ass giving me occasional... Read full Story
Dani_does_Dallas 2021-10-11 4,644 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade pov cum in mouth webcams
100%
Camming Down the Rabbit Hole Ch. 07
Opening my eyes I struggled a little as the residual cum on my face from last night’s show hadn’t been fully wiped off, I felt the dry and crusty leftovers crinkle on my skin, but couldn’t help but smile to myself as I remembered how it had got there. The intensity of that orgasm had been on another... Read full Story
Dani_does_Dallas 2021-10-22 6,100 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade self sucking pov cum in mouth
90%
Camming Down the Rabbit Hole Ch. 08
A familiar sensation greeted me as my eyes opened and a yawn escaped my mouth, that oh so delicious feeling of my morning wood straining against my silk night ware. It was becoming an ever occurring pattern that no matter how large the orgasm the night before I would wake with the hardest of cocks, ... Read full Story
Dani_does_Dallas 2021-11-15 3,672 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Uniform Lingerie Homemade self sucking pov cum in mouth
100%
Camming Down the Rabbit Hole Ch. 09
As per my previous mornings recently, I stirred and rubbed the sleep from my eyes, that delicious feeling of my silk night ware stretching over my taught nipples and my morning wood throbbing in its lace enclosure. The urge to touch myself was palpable, it seemed no matter how hard I came the night ... Read full Story
Dani_does_Dallas 2022-03-22 3,178 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking pov cum in mouth webcams
100%
Camming Down the Rabbit Hole Ch. 11
I sat there for some time, my phone still in hand. I couldn’t fully comprehend the situation and where I was. All this started when I was put on furlough and thought I would be losing my job, an idea born out of boredom, hornieness and desperation. What started as a regular cam show with a guy hopin... Read full Story
Dani_does_Dallas 2022-04-25 3,955 Crossdresser Amateur Cumshot Masturbation Blowjob Uniform Lingerie Shemale and Girl Sex Toys Homemade self sucking pov cum in mouth
94%
Penitentiary Pussy-Butt Boy
Hi: My name is Bobbie. Would you like me to tell you how I became a Penitentiary Pussy-Butt-Boy? Well, it all started with a robbery gone wrong. I wasn’t even in the bank when the guard got shot and I still got almost as much time as the others. So, not long after the trial I was sent to the sta... Read full Story
NaughtyBobbie 2014-04-11 14,831 hardcore suck Big Cock Interracial crossdressing
75%
Being Catfished By Bigoted Bullies?
Okay women, have you ever been in a situation where you're not able to live as your authentic self yet publicly but you also have people in your orbit that KNOW you want to transition and make jokes about you for that? I have people who know me from my life where I'm not out of the closet as MTF pub... Read full Story
NotYourBodyNotYourBusiness 2022-09-08 760 trans feminization pov new bullies inexperienced gay cd to trans woman bigots Thick skin Love Yourself Be Who You Are
71%
Mommies little sissy slut
I have been crossdressing for years now not known to my mother (or so I thought). she is the only person I live with at the moment. when she was going to be out for a few hours I went to her underwear drawer and inside was the most sexy, silky, feminine underwear set I had ever seen complete with ca... Read full Story
shemale lover 2014-09-09 41,840 Lingerie domination cd Homemade sissy
33%
sex
Hello I am mahan Very handsome and curious. The date goes back to last year. With our sister, Sepehr, from childhood, we were on the floor of Khalmun Arshida's daughter. One day we went out with the scene, Arshida called me and his parents went to Istanbul and that lone. And asked us to go over the... Read full Story
sima2000 2019-04-18 3,527 Amateur Big Tits Creampie gangbang Shemale and Girl pov double anal
100%
Sissy gets her Prezzie
Justina woke up on Monday morning and was already tired, she had been dogging till 3 and her little ass was a little bit sore. She made her way to the bathroom and had a pee, brushed her teeth then headed for the kitchen to make coffee. As she was walking her phone went off, she had a text from ... Read full Story
Samantha Jewels 2022-01-06 3,002 Stockings Crossdresser Cumshot Bareback Blowjob Big Cock gangbang domination Mature Homemade Ass to Mouth
100%
badbadboi's walk in the park
...My boi hole was freshly washed, shaved and lubed with a lovely hot shower, my wand is perfect for cleaning my pussy, flushing it clean very time, I luv to let the water spray my hole driving deep enough to tickle the bottom of my prostate. My cock cage locked in place, my white crotchless panties... Read full Story
badbadboi667 2021-04-06 3,439 Crossdresser Amateur Group Sex Outdoor Bareback Creampie Blowjob Interracial Homemade Ass to Mouth cum in mouth
90%
A Schoolgirl Fantasy
As I sat on the couch watching some boring show, I was thinking, "Being alone doesn't have good perks. Maybe if I wanted to dream something naughty, it might be cool." So, I closed my eyes, and I dreamed of a very naughty transexual schoolgirl who would do what I needed. All of a sudden, I heard a s... Read full Story
OldHungDude67 2019-03-04 5,449 Amateur Cumshot Blowjob Uniform Guy Fucks Shemale Homemade Ass to Mouth
80%
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 full Story
Onikky 2019-06-25 9,119 Amateur Masturbation Big Cock Asian Ladyboy gangbang Lingerie domination Guy Fucks Shemale Sex Toys Homemade Ass to Mouth cum in mouth
100%
Lola Chapter 4
We sat at the table. I had made the effort to cook a small three-course French-inspired dinner. I was in love, but Lola’s mind seemed elsewhere. - How nice… She was chewing absent-mindedly. - I have to ask you something. - Shoot baby. Ask away! Lola looked deep into my eyes: - Could you ima... Read full Story
BellaBeau 2023-10-30 5,418 anal Cumshot Latina Bareback Creampie Shemale Fucks Guy Frottage Homemade Lola
100%
Emily and Steve Part 5
Emily, my beautiful blonde transvestite girlfriend and I were on our first out of town weekend trip as a couple. Emily had taken me up to a friend's farm, where we were going to go horseback riding. While I am pretty much a city slicker, Emily grew up in the country and had missed getting out and ri... Read full Story
shemale lover 2012-04-06 2,748 anal sex cum fingering
100%
My Afternoon With Venus - Part II
My mind was still spinning from the out of this world cock sucking I'd just experienced at the expert lips of my exotic little doll as she led me by the hand into her bedroom. Her pink summer dress was draped down onto her waist so now it was only just covering her cute little derriere. As I wa... Read full Story
funpics 2018-03-23 13,172 Amateur Shemale Fucks Guy Asian Ladyboy Guy Fucks Shemale Homemade
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 4,777 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
77%
Glory Hole Whore
I’m a Glory Hole Whore. It started with a trip to a nature reserve, just north of town. I stopped at a large public campsite, to use the bathroom. It was between seasons and I was surprised how large the building was. It had four toilet stalls, two urinals and two sinks, on one side and two shower ... Read full Story
Topazsteve 2020-02-11 12,452 Blowjob Big Cock pov cum in mouth
93%
Virgin Slut Cravings.
There have been so many times that I have had to hide how I felt because I lived my life denying who I was. I was a closet queen who was pretending to be normal. Some might have guessed my secret if they were observant. I didn't do things that other boys my age did. I love hanging out at home like a... Read full Story
Regina10 2020-09-29 8,196 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Lingerie Guy Fucks Shemale pov
100%
Camming Down the Rabbit Hole Ch. 10
As the sun beamed in through a gap in the curtains my now familiar morning wood strained at the silk of my nightwear. How was it that no matter how hard I came the night before it would wake up eager and ready to go. As had become customary my mind would be filled with the events of the previous nig... Read full Story
Dani_does_Dallas 2022-04-12 3,212 Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking cum in mouth webcams
50%
She also conquered my soul...
Initiation in a new era... Almost three months since I offered my virginity to a wonderfull he-woman, Selmi... unfortunately I had to cancel the second day we planned to spend together with my LORDESS because I quitted the town where we met the day before. Since, only few summer fling messages...... Read full Story
hippocampus_171 2022-11-22 3,819 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
41%
My first date with a "shemale"
I met a guy whom i worked with and found out he was bisexual,it didn't bother me nor did i care because i know who i was.I realized he was trying to date me without asking me if i was that way.I flat out turned him down and told him i didn't go that way! I was still young and new to this. I was coo... Read full Story
bmogotti 2020-03-09 12,804 anal first time Small Tits Crossdresser Amateur Blowjob shemale Big Cock Ebony fuck Lingerie Guy Fucks Shemale Homemade motel
83%
First time pretty
This story might not be intresting to anyone, because its true, simple, and not some fancy fantasy. So it was the first time that i dressed in female clothes. I was alone at my home, though I had no idea when someone could come back. I was already shaved on all my body, because its much more comf... Read full Story
KarolinaViennaLeighton 2018-01-16 5,361 first time Homemade Solo Shemale auburn venetian mask brown hair
0%
Crossdreaming Thoughts
Last week I crossdressed for a while. Wore tight dark green jeggings, and two different shirts. I was barely able to squeeze these huge fucking J cup tits into a basically skin tight size XS stretchy nylon beige tshirt, and the other was an olive green turtleneck of the same tight fit. Wore both ins... Read full Story
Maika Arreola 2018-03-02 4,157 Crossdresser Amateur Big Tits Big Cock Mature Homemade
60%
My first gurly orgasm
My first gurly orgasm Me being taught to have my first girly orgasm... 'You cute little bitch, Amber, it is time to have your pussy introduced to your first orgasm. You loved my fingers, and this will be better, I promise. It may hurt a little at first, but, let that pass and you will be in ... Read full Story
amberdoll 2018-07-09 2,385 Crossdresser Amateur Homemade
88%
No hand cum,being pegged by girlfriend, wishing for real cock
I'm a vers guy and / your typical BI guy, but mostly I prefer being the top. I am crazy about gurls, with their thick hard cock ( or flopping dick) riding me . You could say this is a story about me. It describes me, since there's not alot of room in the description column. Like I was explaining ... Read full Story
NWI SLUT 💋 2018-07-12 7,237 Amateur Cumshot domination Homemade
76%
My first girly orgasm
Me being taught to have my first girly orgasm... 'You cute little bitch, Amber, it is time to have your pussy introduced to your first orgasm. You loved my fingers, and this will be better, I promise. It may hurt a little at first, but, let that pass and you will be in girly heaven. I felt s... Read full Story
amberdoll 2018-11-07 4,494 Crossdresser Amateur Homemade
71%
The story of how I became what I am now...
I was on a trip to Germany with some of my friends. I was 16 when this happened. We went to a club one night and I got really drunk. They challenged me to approach a cute girl and ask her for a drink with me. I was drunk so I didn't really care so I went there and bought her a drink. We talked and I... Read full Story
FeetQueen 2019-01-08 5,176 Stockings Teen (18+) Small Tits Amateur Shemale Fucks Guy Lingerie Homemade cum in mouth
38%
Am I gay?
Please help me. I'm confused and unsure if I am gay. I feel so ashamed of myself. I don't want to be gay but I was molested by my neighbors at 6 years old and from then on I would wear my mom's panties or sniff my sisters while masturbating. Cumming would always make me feel guilty for what I have d... Read full Story
Chinaysissyslut 2020-02-24 6,010 Stockings Teen (18+) Small Tits Crossdresser solo Amateur Masturbation Asian Ladyboy Lingerie Homemade webcams
81%
How I knew
Like a lot of you we all have our stories and how we arrived at being our unique selves. I was lucky to have girl cousins that saw me as one of them at a very early age and introduced me to my girly side! Sleepovers were great, I would end up wearing their pjs/nighties etc and never once thought i... Read full Story
Veronica Trapani 2019-12-06 6,656 Teen (18+) Amateur Cumshot Homemade cum in mouth
69%
February 2nd
February 2nd. My first time being fucked in my ass. It was unbelievably satisfying but I want more. I was on a dating app for guys looking for guys. I was just curious never thought that I'll be longing for a dick in me. My first was so-so.. the 2nd time just a few hours after my first was fantasti... Read full Story
Princess Raven 2020-02-06 4,268 Crossdresser Amateur Blowjob Big Cock Asian domination Homemade
82%
Best friend
Looking back, it seems my early teens were really a time for me sexually. Puberty had set in hard and fast and I was sexually charged. I was constantly touching myself and fantasizing about every sexual explicit act I could think of at the time. Lucky for me I had my best friend Jason. We wer... Read full Story
Veronica Trapani 2020-03-09 6,079 Teen (18+) Amateur Outdoor Blowjob Homemade cum in mouth
50%
a bride for a day
A letter from an admirer who will visit me in time. All girls want to be a bride for a day. I went down to see Amber now isolation is over and we spent two days just fucking, spanking, sucking, peeing, smearing, wanking and just about anything we could think of. Them Amber suggested we have a... Read full Story
amberdoll 2020-05-22 2,722 Small Tits Crossdresser Amateur blonde Homemade
0%
a conversation
A conversation .... OMG only just seen you're profile and f...k me you are so horny just love you're sexy legs they look so good in dark nylon and that heavy makeup is just great talk about a fuck me doll you sure are one hot fuck me doll xxx By the way love the garden vid there is nothing lik... Read full Story
amberdoll 2020-07-22 1,984 Stockings Small Tits Crossdresser Amateur blonde Lingerie Homemade
80%
Getting Fucked by Sasquatch
Bill was about to show up, I had known him from a chat room for years now. I was in his town for work and we had set up this date so we could finally meet each other. I heard a hard knock at the door and when I swung it open, I just stood there in awe. It wasn’t the big beard or really long hair tha... Read full Story
pennypenny 2020-08-21 5,763 Crossdresser Bareback Creampie Fetish Blowjob Big Cock redhead domination Guy Fucks Shemale pov Ass to Mouth cum in mouth
81%
First time with ladyboy / bottom
Hi everyone! now it is my turn to share my experience in Thailand. We were on a Christmas vacation on an island, and I didn’t even know ladyboy existed then. At a Christmas beach party I chatted and danced with a woman and we ended up in my bungalow. We kissed a lot and I knew that now I was g... Read full Story
FoxyLover'ts 2020-10-06 15,843 Cumshot Blowjob Big Cock domination Interracial Homemade cum in mouth ladyboy ts thailand ladyboy shemale fuck guys virgin ass bottom boy bottom virgin
75%
The journey down the Rabbit Hole...
Nearly 30 years, living a double life. Sneaking around on two Xwives, several girlfriends, all to play with men.Play,and play and play. Responding to personal adds in the paper at first, then I found the Bath House. Wow, to a closeted homophobic acting oilfield lifestyle kind of guy, who could hide ... Read full Story
badbadboi667 2020-11-24 3,085 Crossdresser Amateur Group Sex Cumshot Outdoor Bareback Blowjob Big Cock gangbang domination Homemade Ass to Mouth
100%
Slut /W Bad Boy
I was excited as always because I was about to go out in public and hopefully I will meet some horny man with some money and get laid. Now, to make sure that I am a picture of femininity, I double checked my makeup in several mirrors from many angles. My lips were perfect and I made sure my cheeks b... Read full Story
Regina10 2020-12-04 6,835 Stockings Crossdresser Big Tits Cumshot Bareback Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale pov Ass to Mouth
100%
a day in the life of Amber
Hi daddy, I hadn't paraded for a few days but I did just a minute ago. He just wanted to watch me really take my dress and panties off He didn't ask me to do anything else really I sucked my finger and fondled my tits for him I would have done anything he asked I have become used to that wit... Read full Story
amberdoll 2021-03-18 2,228 Stockings Small Tits Crossdresser Amateur blonde Lingerie Homemade
100%
Making Love Vs. Fucking
We all know the difference between making love and fucking, but for those that may not here is my take on the subject. When my partner makes love to me it is slow, gentle, sensual....he does it not only to make himself feel good, but to satisfy me as well. Making love is selfless and sacrificia... Read full Story
Chrissy Tunnell 2022-01-28 2,352 Crossdresser Amateur Masturbation Bareback Creampie Fetish Blowjob domination Guy Fucks Shemale Homemade
100%
The Opening of Villa Olivia
All Stories are 100% true. Names and Locations might be altered to protect the privacy of myself and others. In my last blog post I have given you an overview of what happend in the past months. In the beginning of January we have finished the works on my new "working environment". We call it "Vi... Read full Story
TV_Whore_Olivia 2022-02-21 2,372 Crossdresser Amateur Group Sex gangbang Guy Fucks Shemale Homemade escort sissy prostitute hooker slaves owned Hooker cd