Sort by
Relevancy

Free Stories

0%
Brother of the Bride
“What in the ‘Get Out’ hell is going on here,” quizzed the warm, brownish-red woman with the Bantu knots as soon as they were safe inside the gold 1970 Deuce and a Quarter. “I don’t even know,” chuckled the driver as he jerked his head to get his short dreadlocks out of his line of sight. “Wel... Read full Story
Faggyboi and Puzziboi 2023-07-15 5,124 anal Crossdresser Guy Fucks Shemale Interracial sissy femboy faggot sissy crossdresser BB jack of spades bblbuttcd bbl
50%
Baby Face Jack's Biggest Fight
The referee held his gloved hand high in the air. The crowd was hushed as the ring announcer spoke, "Ladies and Gentlemen, the winner of this World Featherweight Championship Boxing Match to unify the title, by technical knockout, and still undefeated; Baby-face Jack Mc Coy." The crowd scr... Read full Story
shemale lover 2012-02-08 7,087 fuck oral
100%
About Jack and Diane
Thanksgiving was over the college kids are returning to school and Las Vegas has slowed down from the busy restaurants and overcrowded casinos. It’s the best time of year to see a nice show for less. Jack’s friends had all taken off with families and he had time to think about how lonely he really w... Read full Story
Jon Paul 2023-12-20 6,575 anal Cumshot Bareback Fetish threesome Lingerie Guy Fucks Shemale small cock shemale fucks shemale cum in mouth shemale + shemale
96%
Making A Man Out Of Tommy
I have two good friends, Brad and Matt who are actually my fuck buddies. Both of them travel for work, so they tend to be gone a couple of months at a time. I have a key to their apartment, so I can let myself in for sex when they are home and to bring in the mail when they are not. I also get to us... Read full Story
pennypenny 2018-08-31 9,797 Teen (18+) Crossdresser Amateur Masturbation Bareback Creampie Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth cum in mouth
84%
Shool teen crossdresser first time sex
I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my new red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest f... Read full Story
shemale lover 2014-11-21 18,423 first time suck fingering Lingerie ass fucking cd
95%
Shocking shemale surprise
I had been out with friends partying after a professional basketball game and reached my hotel around 12:00 I wasn't yet tired and not needed anywhere the next day I decided to call for a massage. I had an adult newspaper and really didn't read the add. I basically called the first number I came ... Read full Story
shemale lover 2013-06-25 7,001 Cumshot suck shemale oral Lingerie cum swallowing
100%
My first time wearing sexy lingerie Part 2
I could not wait to get home from school the next day after wearing my moms sexy panties the night before. No one was home so i could have fun. As soon as i got into my room i took off all my clothes and went into my moms bed room to see what I could put on. With my mom working at Macy's in... Read full Story
shemale lover 2012-09-15 5,394 first time Cumshot Lingerie jacking off
100%
FÉMINISÉE PAR BBC MALE ⚧️
Après avoir abandonné l'université, je n'avais évidemment plus le droit de vivre dans les dortoirs. Mes parents ne me reprendraient pas. Je n'avais qu'un seul endroit où aller : l'appartement de mon ami Jack. Nous nous sommes rencontrés au collège en première année. Il a toujours été bon avec moi. ... Read full Story
Femboy 2021 2023-02-16 1,007 Stockings Crossdresser Fetish Blowjob Big Cock Lingerie domination Guy Fucks Shemale Interracial cum in mouth
100%
A Fairy Tale Part 2
=-=-Chapter Six-=-= I woke up sometime later and I was feeling better, even a little hungry actually, and I wanted a shower and I needed to pee and...I cocked my head as I heard the unmistakable sounds of Mistress Stacy's bed moving. She had a large one, king sized, with old springs or somethi... Read full Story
shemale lover 2011-12-06 6,643 Creampie Big Cock ass fucking
80%
A Fairy Tale Part 1
=-=-Chapter One-=-= "Heather?" My boyfriend was knocking on the bathroom door. "What's wrong, are you okay? Heather?" "Yeah..." I swallowed thickly and that was a mistake. I threw up some more, kneeling on the floor, feeling like I was dying. "Heather?&q... Read full Story
shemale lover 2011-12-06 11,360 Bareback cum ass fucking slave
100%
I Fooled Everyone But the Black Pimp Part 4
Fuck. I said I wasn’t going to do any drugs and I’m drinking this Gatorade that I know has something in it. Trish said it would help my nerves, and it has, I feel loose…and very horny. When I’m usually horny my cock is hard but right now, I’m putting lotion on my body and I’m going really slow over ... Read full Story
cdtampa4u 2023-05-17 4,929 Crossdresser Blowjob Interracial sissy bbc
71%
Birthday Present Part 1
Birthday Present or (I've Looked at Love from Both Sides Now) Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all abo... Read full Story
shemale lover 2013-01-18 11,213 hardcore sucking Blowjob Lingerie ass fucking
82%
Bikini Boy
I was the boy my father had hoped for after 3 daughters before me. Life in our suburban middle class two-story house was as normal as anyone else's. My dad was a loving father bringing me up and doing the things a father likes to do with his son – baseball, fishing, camping, working the garage... Read full Story
shemale lover 2012-06-12 15,286 Cumshot Fetish oral sex crossdressing
50%
Why Do Guys do this?
Why do guys on the porn, dating sites and social media sites I'm on want to chat live on video all the time? And if I don't agree they unfriend and even block me. Why? Aren't my videos and pixies good enough? They are of me...they ae real, and not photoshopped (except for sharpness and clarity.) I h... Read full Story
Chrissy Tunnell 2022-03-14 2,584 Crossdresser solo Amateur Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Frottage Homemade pov Compilation
69%
My aunt made me a transvestite
My aunt and uncle lived two doors down from me when I was growing up. They had a son one year younger than me. We played together all the time and I was at his house or him at mine all during the summer months. My aunt was a big woman, she was 6ft. tall and weighed around 165. She was even taller in... Read full Story
shemale lover 2013-08-09 29,204 Teen (18+) suck oral Lingerie make up
54%
My Job, For The Past Five Years
Hey, everyone! This is Eva Patricia Meglesch and I am really pleased to welcome you to my personal Sissy Social page! I am currently located in Bucharest, Romania and I have been employed for the past 5 years as a Front-Desk Receptionist for a women's fashion/clothing& accessories compan... Read full Story
EvaPatricia_OfficeLady 2018-05-22 3,268 Crossdresser redhead Sex Toys office sex secretary Eva Patricia Office Sissy
100%
Visiting Ella
Ella is a beautiful, slim Asian TS. She has long legs, pert breasts a cute face and a cock a bit smaller than mine. For me, her knockout feature is her knee length, coal black, sleek & silky hair. I am very turned on by girls with long hair. I have no idea why, I just am. When I got off the t... Read full Story
Jimmypopp 2024-05-05 2,198 Asian Ladyboy Guy Fucks Shemale Frottage long hair hairjob
85%
Unforgettable First Time
I am in my late thirties and have known for a while that I have a sexy body. I'm 5'11", slim and athletic with little cherry butt and shapely legs. A lot of women have told me my body is sexy. A few men have mentioned it too. Sometimes I get photo-snapped at the pool or the beach. I've been luc... Read full Story
shemale lover 2016-05-06 10,074 cum oral deepthroating
92%
Nicole and I the final chapter
So I haven’t written any stories in a while , so if you read mine before you should like this one I didn’t write it yet cause it’s about my last encounter with Nicole. Very sad day for me lol but a very good story. So here goes........ Nicole and I had been going over a year now and everythi... Read full Story
Duke04 2018-03-07 4,230 Stockings Blowjob Big Cock redhead Sex Toys Ass to Mouth cum in mouth
100%
MY First Time with a non-binary/cross-dresser
After I had graduated high school but before I had left for college: I was hanging out with a friend and a friend of theirs at their friend’s house. For the story let’s call my friend Dan and his friend Charles. We were watching some movie on Charle’s (parent’s) big TV. Charles gets up eventually an... Read full Story
ghostpeople 2019-03-12 6,961 first time Crossdresser Amateur Group Sex Cumshot Bareback threesome Frottage Homemade sissy blow job condomless
100%
Jack & Jill - his first time with a transexual
Jack and Jill meet It was when I went to the patio to enjoy a cigar after dinner that we met. On the road for business, I found a decent bar and grill near my hotel where I was welcome to enjoy a fine smoke. I had dinner and then moved outside for a relaxing smoke in the cool weather. I lighte... Read full Story
shemale lover 2012-04-09 5,184 anal sex oral sex cum swallowing deep throating
100%
Meeting Amanda
I’m a happily married man. My wife Tess and I have been together since we were teenagers. We were each other’s first real lovers and being in our mid-thirties by now, we still madly in love with each other. Tess and I always are very honest and open to each other. Both in normal life and sexual... Read full Story
rforasht 2022-07-20 7,271 Big Tits Cumshot Shemale Fucks Guy threesome blonde Big Cock Lingerie Shemale and Girl redhead Homemade Shemale fucks couple
100%
Two CD's the first time we meet.....
We are meeting for the first time since talking online. I want to dress for you gurl, I want to feel as you do, I want to be your slut, your slave of desire. My panties are a sheer white, my hard cock can be seen ever so pressing against them, I rub myself for you as you watch, drooling now. Hand... Read full Story
kelliecdgirl 2024-04-10 3,283 Stockings Crossdresser Cumshot Masturbation Fetish blonde Big Cock Lingerie pantyhose Frottage sissy femboy shemale + shemale
100%
Wife got suspicious...
Wife got suspicious... I ended up having a relationship with a married man I'll call Tom. I didn't know he was married until he told me we had to stop kind of like dating because his wife was getting suspicious. We met online, he was a guy who liked crossdressers like me. He was pretty cute... Read full Story
Kellygirl81 2024-06-18 390 Stockings Crossdresser Cumshot Lingerie Frottage cum in mounth
71%
A Ski Bunny is Born Chapter 4
Our next port of call was Copenhagen (Denmark!). We left London early one wet afternoon and flew across to Denmark's capital, which was also wet! The flight was relatively short and when we arrived we caught a taxi to our city center hotel. We had 5 full days here and were intending to enjoy each on... Read full Story
shemale lover 2012-06-22 7,016 butt fucking facial oral sex
64%
Big Cock Heaven
This story is written from the Shemale's point of view. "Jane" is based on a real Transgender woman from California & my friend. She gave me the outline of a meeting she had with "Janardhan." ***** My name is Jane and I am a natural red head blue eyed 34 year old T... Read full Story
sach 2015-11-16 7,222 Big Cock ass licking redhead rimming Shemale on Guy
100%
Horny Writing A Strange Habit
I enjoy watching videos which I can Vicariously live. This is nothing more than my horny hobby, an amalgamation of various thoughts. My form of hands free edging. Spell checked only, "No I haven't proof read a first draft, not trying to publish masterful works here." Hope to hear from those w... Read full Story
Araina 2021-03-08 2,663 Crossdresser Amateur Big Tits Cumshot Bareback Fetish Blowjob Big Cock Guy Fucks Shemale Frottage Homemade Ass to Mouth cum in mouth
50%
Need A New Keyholder/Daddy
I get an erotic thrill off of the thought of another man "owning" my body and having control over my sexual pleasure. I enjoy having my boyclitty, my cock, locked up in a chastity cage; it represses my erections, hides my cock so I rarely see it, and denies me any of that little sexual pleasure of t... Read full Story
Chrissy Tunnell 2022-02-14 2,201 Crossdresser solo Amateur Fetish Ladyboy Lingerie domination Guy Fucks Shemale Frottage
66%
A Christmiss Story
The weekend! With my first week as a secretary finally at an end, I knew exactly how I was going to spend it: sleeping till noon, then watching football on TV while binging on bratwurst and beer. When I woke up on Saturday at half past noon, I lolled in bed for another hour before I dragged mysel... Read full Story
shemale lover 2012-02-23 4,286 transformation orgasm fingering
100%
I fucked my personal trainers ass for the first time
I greeted him on my bed in my sheer black lingerie. I knew he’d be nervous, and truly I was as well. We’d spend so much time in the gym together and I knew he wanted me, but taking that next step was sometimes difficult, especially when our relationship was always professional. Posing for him, I r... Read full Story
Madison Heights 2023-05-18 6,834 anal Shemale Fucks Guy Big Cock Frottage
100%
TS Prostitute Urge
After college I began to explore the world. To that point I was the average male that happened to get a lot of tail. My sexual exploits with women were something I was proud of and always gave me a sense of being a real man. After years of watching straight porn and imagining myself in every possibl... Read full Story
shemale lover 2012-01-27 3,505 Group Sex sucking cum
100%
Sexretary
Sam Nichols had a comfortable, reasonably well paid job in a computing firm called Stewart Computing. He was twenty two and had recently graduated college and had been lucky to find such a good job in the firm on the edge of San Diego, just a couple of hours drive away from where his parents still l... Read full Story
shemale lover 2011-11-12 8,095 anal shemale oral
22%
Just me...
When I first started to get high, I was such a good freak. I started taking pictures of myself in panties and lingerie, taking pictures of my dick and showing the world, showing off my tight little asshole, just trying to become a porn star. I still want to be a porn star because I know that I would... Read full Story
AllOfMe 2018-06-01 3,755 Teen (18+) Ladyboy redhead Guy Fucks Shemale Interracial Ass to Mouth cum in mouth
100%
Beryl's birthday suit
I tried on my sister's panties when I was 12. They looked so cute, so sexy.. I couldn't help myself. I tucked my dick between my legs and pulled them over my hips, delicately positioning them just like a girl. They felt yummy! When I saw the shiny, lacy pink briefs in the mirror - snug, flat pu... Read full Story
Beryl 2023-12-12 6,960 first time Stockings Crossdresser Bareback Blowjob Big Cock Lingerie redhead sissy cum in mouth
100%
Angel & Victoria
Angel was a beautiful young girl living with two of her best friends, Monica and Amanda. All were transsexual, and the three shared everything together, from clothes, their sexy intimates, lovers, and each other's bodies. Angel was the youngest, at 23, a Japanese anime lover and the most... Read full Story
shemale lover 2011-09-23 5,689 anal Creampie Big Cock oral
100%
Discovering Amber Chapter 3
There have been very few times in my life I have been terrified and today was definitely the tops on that list. Ms drove us to the mall and as I watched she walked around the front of the car and opened the door for me. I looked up to see her hand extended toward me. "Practice getting out li... Read full Story
shemale lover 2012-09-28 4,039 sucking Fetish domination Sex Toys
80%
His Pretty Little Party Dress
Percy was so excited he could barely contain himself. His birthday wish was coming true! He was getting to celebrate his birthday like a real little girl. The frilly girl's party-dress he was now wearing was splendid! It was a soft pastel-yellow little girl's traditional fancy party dress. Very, ... Read full Story
ALEXEAMES 2024-01-13 4,148 Stockings Crossdresser Amateur Lingerie redhead Homemade sissy femboy
50%
Liberty meeting, chapter1
On a beautiful summer day, my phone rings. It's Steve, the boss of a transvestite company who calls me. - Hello Sandra, I have four new friends waiting for you at the club. - Thanks for thinking of me, I'll be right there, I said, hanging up. I am happy with his call because I always meet ... Read full Story
sandratvtg 2024-06-20 194 Stockings Shemale Fucks Guy Fetish Lingerie shemale + shemale
100%
Maxine and Pam's Love Story
Oh, that Dominant TV was so mean! She really did rape and humiliate both of us. I will never consent to having her over again. I am so so sorry I thought of having a Dom play with us. It seemed like it would a real turn-on for both of us when we picked her up at the CD bar. I thought it would be fun... Read full Story
PamBiTV 2012-12-10 3,506 sucking cum Lingerie
83%
Janine awaits
My story is not typical. Sure, it mirrors many of the others you’ve read except for one aspect, that is my age. I recently celebrated my sixtieth birthday. Yep, the big 60. And not that I am trying to brag but I am one of the sexiest bitches around. As recently as five years ago I looked like any ot... Read full Story
bunny cat 2019-02-04 3,728 Crossdresser Masturbation Blowjob Lingerie Mature cum in mouth
100%
Regina’s Double threat.
Hello guys, I recently ran into a former hater who was no longer the hater I had met years earlier. In fact, he had only treated me so horribly because of his own inner dark desires. When we met a few years ago at one of the clubs, he had been very abusive to me. He went out of his way to say hurtfu... Read full Story
Regina10 2022-02-08 2,976 Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock redhead Guy Fucks Shemale Ass to Mouth double anal
100%
Meeting Amanda Ch. 2 - The Next Day
After a hot evening together, the story continues https://www.ashemaletube.com/story/meeting-amanda-6595/ ------------------------------------------------------------------------------------------------------------- “I could really use a shower,” Amanda said while she... Read full Story
rforasht 2022-09-07 4,220 Masturbation Shemale and Girl redhead Guy Fucks Shemale cum eating anal creampie couple & shemale
100%
Dormitory Fire Drill
The bed in Beverly's dorm room was narrow. It forced their naked bodies close. That was fine with Les, it increased the intimacy. As they spooned together, Les's arm draped across her waist and fondled the bottom of her left breast. His face pressed into the hair at her neck and inhaled the wonderfu... Read full Story
shemale lover 2012-10-31 3,306 Fetish orgasm Lingerie
89%
Shocking shemale surprise
I had been out with friends partying after a professional basketball game and reached my hotel around 12:00 I wasn't yet tired and not needed anywhere the next day I decided to call for a massage. I had an adult newspaper and really didn't read the add. I basically called the first number I came ... Read full Story
shemale lover 2013-08-09 13,271 suck shemale Big Cock oral swallowing stroking
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 3,930 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
100%
Why I’m a Cock Whore!
Hello Love, The summer before my freshman year in high school. I found a VHS porno video right next to a dumpster behind our local video store. Brought it home. Couldn’t watch it until my family left to use the VHS player. It turned out to be a she male porno at first I felt weird but after watch... Read full Story
Samantha Cummins 2023-04-18 6,007 anal Stockings Cumshot Creampie Lingerie femboy Ass to Mouth cum in mouth
0%
Darkness Fantasies #2
Darkness The engine warning light was blinking rapidly, its red urgency causing a rising panic in Jack. Limited mechanical knowledge, an unknown area of the county, pitch blackness and hammering rain, none of these signs a good omen.He groaned inwardly as the engine coughed, spluttered and then jus... Read full Story
Streethawk75 2023-04-18 3,995 Amateur Cumshot Outdoor Masturbation Fetish Lingerie big ass
100%
Charisma Part 1
Tiffany De Vine wondered whether the ladies’ dressing room in which she was about to try on a brassiere was under surveillance by some fat, obese fucker with a day’s stubble of beard and a cum-stained crotch. Probably, she thought; it would be just her luck. Well, if some slob was drooli... Read full Story
shemale lover 2011-09-03 3,511 Big Tits shemale Lingerie
91%
Birth of a New Sissy Part 1 Encounter
I met Jeff one day at the nearby tennis courts. I could never have imagined what the result of that meeting would be. I suppose I should tell you a bit about me. I'm a happily married 34 year old. About average in most respects. A little spare tire trying to form around the middle but in decent ... Read full Story
shemale lover 2011-11-17 5,253 cum Sex Toys crossdressing
91%
Stepdaughters Pleasure Daddy
As I was showering, I was thinking about Anna coming. What would I say to her? How would I act? I felt very uncomfortable and I was getting extremely nervous. I finished washing, then shaved. As I was getting dressed, Dawn came in. "I know your hungry, Daddy, but let's go out for breakfast.&... Read full Story
shemale lover 2011-12-05 7,576 anal licking Creampie
96%
New Job, New Life as as Sissy Slut Chapter 2
I was left lying on the floor, my face completely covered in cum. I was wearing lingerie and a dog collar and I had just been fucked long and hard by my "boss." My virginity had been forcefully taken. The thing is that I loved it. I loved being manhandled by this muscular man and I really ... Read full Story
shemale lover 2012-12-23 7,348 Cumshot Uniform Lingerie ass fucking domination
95%
Ginger's First Gangbang
I had been enjoying regular meetings with my older lover, Mr Webster, for some time and the routine typically consisted of meeting up and heading off in his car for sex at some secluded spot in the countryside. He liked me to dress as femininely as possible, in pretty dresses, skirts and heels and a... Read full Story
Ginger__57 2018-03-26 8,502 Stockings gangbang redhead domination Guy Fucks Shemale Ass to Mouth cum in mouth
92%
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 full Story
pennypenny 2019-01-08 7,175 Stockings Crossdresser Group Sex Cumshot Masturbation Bareback Creampie Fetish threesome Blowjob Big Cock gangbang Lingerie redhead domination Guy Fucks Shemale Sex Toys Ass to Mouth cum in mouth double anal
100%
HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
CDDIXIE4U 2019-01-08 13,636 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
100%
Ride of My Life
As a student at college I wanted a bicycle for Christmas. I hadn't past my driving test and even if I had, I couldn't afford to run one with my Saturday job wages. My parents didn't have much money so I didn't ask for an expensive model by name, anything would do. I didn't think they could go far wr... Read full Story
shemale lover 2012-09-04 7,101 Crossdresser Big Tits Blowjob Big Cock heels
100%
A SLUT is born...
I've always had this magnetic attraction to slender pointy hi-heel stilettos for as long as I can remember. Even when I was just a kid of around five years old, I used to get these strange feelings between my thighs every time I saw a young teenage girl strutting and teetering around on these f... Read full Story
caroletv31 2018-04-23 6,845 Stockings Amateur Masturbation Ladyboy Lingerie cum in mouth