Sort by
Relevancy

Free Stories

100%
Don/Dawn of the Dead
I did all of the 'normal' things first. Checked all the doors, checked all the stores, closets, back hallways, stockrooms and bathrooms for zombies. Made sure everything was sealed off. Established a base inside the mall to operate from. Made an escape plan. Hid some of my guns and ammo in a cache w... Read full Story
shemale lover 2012-10-25 3,500 first time oral jizz
95%
Jordan's First
My name is Jason, I am a 33 year old road worker. The pay is okay but I never had much more than what I needed to live comfortably. I was hoping to save up for a nice vacation and decided the best way to do that was to take on a roommate. I live in a decent sized two bedroom apartment and the seco... Read full Story
Hydra1979 2019-01-25 9,579 Stockings Crossdresser Masturbation Blowjob Lingerie
100%
Me and a transvestite man part 2
OK this is the second part of my true story. I was going to leave it at two parts, but I think there's enough to make it three parts, now! I think I'd best point out that beyond the (I'm told) common early sexual experiences most straight men have as youngsters, with other men of their age, I'd n... Read full Story
shemale lover 2011-08-15 2,415 first time shemales gay male
71%
Caught by my wife
I was stuck, I couldn't move, literally in headlights... I dress up okay? you caught me, I guess your the master now... I used to control my wives life and for good reason I pleased her, and she pleased me the best she could... well now that's changed.. she came home from work early last Tuesday and... Read full Story
shemale lover 2011-12-07 4,418 first time shemales Group Sex
100%
Planet Of Men
At 1600 Eastern Standard Time (EST) on September 27 in the year 2020 AD the UN announced that General Atomics Corporation (GAC) had saved the world. After years of panic in every country that the world was doomed due to the effects of global warming, GAC announced that, with funding provided by the ... Read full Story
shemale lover 2012-05-04 4,020 first time Stockings facial oral sex transvestite
100%
Bi Pantyhose Passion
I've had a Pantyhose Fetish for over 30 years now, and love wearing them on a daily basis. But back in the summer of 1995, I suffered a heat stroke, and almost died, when I recovered, I vowed I would stop fantasizing, and live out these dreams and fantasies. I had been masturbating while dress... Read full Story
shemale lover 2012-06-04 4,040 first time Cumshot Masturbation Fetish Blowjob pantyhose
100%
Fantasy Reversal Chapter 3
Gentle reminders of my first orgasm continued, until the shower water was no longer warm. It seemed like I had been there for an hour. As I looked down again, the female body I saw was not what I had hoped for. My cock was not there, I was in her body, the body of Katrina, my wife. What had she done... Read full Story
shemale lover 2012-06-29 2,501 first time Cumshot Fetish crossdressing heels
100%
First Time Drag Chapter 2
We'd been together for almost one full year, maybe the happiest year of my life. Michael had expanded his feminine side, dressing up and wearing makeup more often than not. His hair had grown too, now almost at shoulder-length. Though twenty-one, he was still really just a boy, or maybe just a girl.... Read full Story
shemale lover 2012-10-12 2,051 Cumshot sucking stroking
100%
My new feminine compulsion
Until I saw shemale porn on the web back around 1998, crossdressing had never occurred to me. But when I saw those doubly-sexy bodies, with both breasts and a cock, my sexual life really changed. I searched out every shemale porn site I could find, and found myself especially excited by hot shemales... Read full Story
shemale lover 2012-10-07 3,623 first time crossdressing shemale porn
75%
First time with CD when I wanted tranny
(True story)I got in touch with an asian tranny online (as most people do lol). I've always had an attraction towards trannys, especially really sexy black ones which appear in porn but i've never fulfilled my fascination. I'm straight and have slept with the sexiest women going but have a curious s... Read full Story
BLKfreakUK 2013-07-23 8,183 anal sex Cumshot Asian oral sex condom sex
100%
White Dress
It had been a busy week and come Sunday afternoon after a softball game I was craving a cold beer, a couple of my teammates decided to tag along and go to a bar. Once getting there the drinking started and by the time they closes down we still wanted to keep going. There a was a place that open a... Read full Story
PeterPiper8 2021-10-08 2,878 anal first time tranny Blowjob Lingerie dress throat
50%
My First Time Out Part 4
It was Sunday morning at eight o’clock when the phone rang. Shayna’s eyes felt like they were glued shut but managed to answer the phone on the third ring. “Morning,” said Shayna as she was still half-asleep. “Good morning Shayna. This is the Bell Captain calling.... Read full Story
shemale lover 2011-10-18 4,386 cum oral facial deep throat fucking
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 5,174 anal sex oral sex cum swallowing deep throating
87%
My one and only meeting with a very hot cd
Meating Samantha It had been almost two years since my first experience with Dave. That was the first time a man had sucked my cock. It was the first time I had touched another cock and the first time I had sucked a cock. That day was the birth of a new me. I no longer was a homophobe. Although, ... Read full Story
BushBuns 2014-05-07 3,919 first time Stockings suck Blowjob cd
97%
MY FIRST SEX WITH SHEMALE
This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous durin... Read full Story
shemale lover 2014-11-23 26,115 tranny suck shemale fingering Lingerie ass fucking
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 6,824 anal Shemale Fucks Guy Big Cock Frottage
100%
Bob and Carol and Gemma and Alice?
I sat there, in the kitchen, suddenly very nervous again. The previous half-hour had started out nerve-racking enough but I had settled, more quickly than I had imagined. Carol hadn't laughed, she had been kind, and interested, and considerate, and she had listened and asked intelligent questions. B... Read full Story
shemale lover 2012-07-22 3,605 first time Cumshot oral sex cum swallowing
83%
Double Take
Sandy Lane glanced at his Rip Curl watch as he paddled back towards the lineup. Less then twenty seconds remaining in his heat. Sandy had one good wave under his belt, but unless he nailed another one, there was no way he was going to make it into the finals. He glanced over his right shoulder, a... Read full Story
shemale lover 2012-11-03 3,316 first time crossdressing
84%
First Time Crossdressing with a mate part 1
It was the height of summer, and my girlfriend was out of town for 2 weeks. I'd had a handful of experiences with guys before, but ever since I dressed up like a slut for the first time, I couldn't stop thinking about meeting another crossdresser for some horny mutual fun. I had been faithful to my ... Read full Story
shemale lover 2014-07-21 6,045 Cumshot suck wanking swallowing 69 cd
70%
Sara by Sara
1000 – Sissy Story 29 – Sara by Sara Filed Under: Sara, Sissy Story by Anna Malice — 3 CommentsFebruary 26, 2012 4.00 avg. rating (81% score) - 3 votes Post number #1.000 I never thought to reach this moment.. in truth i always thought to cancel this blog.. a lot of time before of this.... Read full Story
saralovescd 2017-05-02 4,893 first time crossdressing college
100%
Junior's Department
Junior’s Department The long-haired young male browsing alone in the ladies’ junior’s department caught his eye and he stopped walking to the store exit. He stepped behind a display rack across the aisle, then watched him approach a mirror and scan the area before holding the skirt and blouse up ... Read full Story
AuthorJordanSkythe 2022-01-20 2,647 first time Stockings Crossdresser romance femboi
100%
But it's just two guys right?
CD's and TV's are not really chicks they are guys and they have guy sex drives! Unlike many online Cyber Queens as I call them. Years ago I did do some cross dressing. Unlike those AOL and Yahoo frauds I really did dress up and unlike them despite digital cameras being new things and ve... Read full Story
Jennifer4u727 2016-11-03 16,316 first time cd tv hotel Straight Guy
90%
Becoming a Drag Queen
I was thrilled when my boss told me he was sending me to San Francisco for a conference. It was a location on my "Top 10 places I wanted to go". I went online and Googled the major attractions and tourist "must sees in San Francisco. The conference was Wednesday to Friday and I figure... Read full Story
shemale lover 2012-03-01 13,812 first time sucking fuck domination
85%
Shemale Public Bondage Fantasy
It was a chilly evening, I had arranged to meet him in the city centre. I was wearing a rather skimpy black dress, black lingerie and red high heels. It was my first time dressed in public like this. He was an average looking man, he shook my hand and kissed my cheek, and asked if I was ready. I aff... Read full Story
shemale lover 2013-06-22 4,809 Cumshot Outdoor shemale Lingerie ass fucking domination public
50%
A Shock at the Adult Theatre
I am very often thursdays in the adult theatre, because stylde crossdresser have free entrance at this day. I used to go there by public transportations, because I have no car. In the rear area of the shop we are able to change our clothes and to style up and storing our bags in a locker. About a... Read full Story
SilkeTrav 2020-01-20 7,865 Crossdresser Amateur Outdoor Masturbation Lingerie Homemade
91%
My Seductive Secret (True Story)
During my childhood, me and my brother used to play with two other boys who were our neighbors every weekend. One day we decided to wrestle, and I took on the youngest one, (he was about 2 years younger than me, like my brother) and we wrestled in the shed while my bro and his bro (who was my age) w... Read full Story
Chickzdigmeyup 2019-06-18 13,942 Stockings Teen (18+) Small Tits Crossdresser Cumshot Outdoor Masturbation Bareback Fetish Blowjob Big Cock Lingerie domination Sex Toys Homemade cum in mouth
100%
Summer sun
Evening sunshine is lovely. For a start I can wear less, no coat, no warm clothes, in fact a skimpy skirt and strappy top that covers not much more than the tops of my hold ups and my bra. I like to walk in countryside and feel the warm breeze gently ruffle my clothes and visit those areas where you... Read full Story
shemale lover 2013-05-22 4,122 suck Outdoor wanking stroking public
100%
Dressing and driving
A little about me, I'm married, and wife doesn't have a clue I like to dress up. I would love to have her know and accept it, but I don't think she would. I do cam and love to get instructions from people that are watching on cam. Am I a sub? I think I am. I like to drive dressed. When I take a driv... Read full Story
SandyCrossdresser 2018-11-26 5,574 Amateur Outdoor crossdressing driving Reast area
100%
Steve
So on AFF, I used to be gold but guys will just hit you up, sooo I got hit up by an 8in boy. Wasn't sure I'd want to prep up an 8 so I didn't get all ripped up, but nice profile and a fucks a fuck sometimes. What to wear to get cum in tonight? Still pretty warm, I'll go mini with tighter leotard (mo... Read full Story
smtmsbrianne 2020-09-16 3,429 Crossdresser Amateur Group Sex Cumshot Outdoor Bareback Creampie Big Cock gangbang redhead Guy Fucks Shemale Ass to Mouth cum in mouth
100%
TO BE OR NOT TO BE - PART 4
TO BE OR NOT TO BE - PART 4 by Spanky de Bautumn Part 3. Everybody was working hard for opening night when tragedy strikes and Sunny has to make a decision. Walking back to the hotel, I was lost in thought. I was excited but at the same time scared to death, confused and clear of mind, think... Read full Story
SpankydeBautumn 2021-02-23 2,348 Small Tits Crossdresser Outdoor Fetish Lingerie Mature pov
100%
Dream Bride Tranny
My niece Avril and I rushed along the ground floor corridor of the hotel and made sure none of our relatives were watching us as we disappeared into the room. Inside, we were met by Miss Anne of the Kinky Brides Group, who immediately ordered Avril to strip me naked. "Please, not today,&q... Read full Story
shemale lover 2012-11-13 5,486 anal cum oral Lingerie
86%
How some guys found out I'am a slut
So there is this guy i sometimes meet. He loves to use me like a little slut and i love to be used too. This night i went over to his house stripped a little for him and asked him if he wants to cum deep inside my ass. This would be the first time for me to have cum inside my ass cause he normaly cu... Read full Story
cdvanessa88 2016-09-12 8,930 Outdoor Creampie cum fishnet slut high heels
100%
Getting caught naked in public.
I always have loved the risky nature of being fully naked in places where you aren't normally. i don't want to offend some unsuspecting person while out hiking or driving on very unused roads. BUT.. at the same time, the risk is exhilarating, and the thought of being caught and the one who caught me... Read full Story
Exhibitonist 2024-02-10 4,471 Outdoor Masturbation teen (18+)
100%
I Missed Myself
As soon as Dr. Griffin returned to the examination room, I knew that the news wasn’t good. I could tell by the way he avoided my eyes as he studied his clipboard and fidgeted with his pen that something was wrong, terribly wrong with me. The ache in my groin that I had been ignori... Read full Story
shemale lover 2013-03-20 7,886 Crossdresser Lingerie pantyhose cd softcore
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 13,603 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
81%
A pervy uncle invited me to his house at 10 PM..!
It's been 8-10 years now, I had this amazing experience. I was standing at the bus stop in my area/street(my daily routine), one uncle was watching me but I ignored eye contact as I feel awkward the way he was looking at me because I act straight in public and I felt that he's seen my girly ... Read full Story
Cindy Sky 2021-07-20 7,061 Teen (18+) Small Tits Amateur Cumshot Outdoor Bareback Creampie Fetish Blowjob Asian Ladyboy Mature
87%
Both Sides Of The Coin
Jessica and I were back at the scene of the crime, so to speak. Her work friend, Mike, hosted a costume party every year on the Saturday night 8 days before the Super Bowl, "Because there's never anything else going on that weekend." Last year, that tagline on the invite offered suffic... Read full Story
shemale lover 2013-01-28 5,424 Cumshot Outdoor sucking Blowjob deeptroat
100%
I met a guy in the nightclub and I didn't tell him I was Trans
I’d worn an absolutely killer dress just to make sure I got what I was looking for that night. Dancing under the lights I could feel eyes all over me, and as the evening progressed men became bolder and bolder about approaching. This one was athletic, sexy and had all the right dance moves, at least... Read full Story
Madison Heights 2023-03-25 6,554 Cumshot Outdoor Blowjob Big Cock cum in mouth club outfit Surprise Cock Partying surprised
57%
Cumming and peeing in public while driving.
As I have previously posted, when I have my cock ring on a weird sensation exists, I feel like I need to pee more often than normal, but about 90% of the time I feel like I am going too cum. Weird one today, on way back from checkup at the doc, driving home, I started thinking about taking my coc... Read full Story
shaper2000 2019-08-05 2,902 solo Amateur Outdoor Masturbation Fetish
100%
Caught Out In Lingerie
I had only just started my new job in a big new department store. I had forwarded my CV almost as soon as the foundations were poured, and I watched as the big new building took shape. It was to be the biggest and most modern store in the county where I lived, and I was determined that I was go... Read full Story
shemale lover 2011-08-25 5,307 Fetish Lingerie crossdressing
100%
Caught and liking it
Synopsis: after being caught by mum, then auntie, auntie takes over my exploration of my femininity. Aunt Teresa had a friend in psychology. She scheduled a meeting and this lady talked to me for several hours. In short, she informed auntie that I had gender confusion and seemed to relate more to... Read full Story
shemale lover 2012-07-04 2,382 first time Fetish crossdressing
90%
Waited long enough
I have always dressed in lingerie and women's clothes. I recently turned 38, and me and the wife have been experimenting in the bedroom. I talked her into letting wear lingerie, for starting this bedroom play. I have been wearing panties around her for a year now. Finally about 3 months ago I w... Read full Story
420jester 2014-09-23 4,347 Cumshot fingering Lingerie crossdressing cd
88%
caught with my pants off
CAUGHT WITH MY PANTS OFF When they walked in the unlocked door, I froze like a deer caught in headlights. Although Carol was my girlfriend and we had great sex, I still enjoyed my closet dressing. I love the feel of lingerie and the way lingerie makes feel like ... Read full Story
cdlishmis 2018-12-10 5,600 Crossdresser Amateur Lingerie CAUGHT!
90%
Angela's Panties
I am a 32 year old bi-curious guy married to Angela (27). Although I’ve never been with another guy I have had lots of gay fantasies. Most of these revolved around dressing up in women's underwear and making love to another similarly dressed guy. I spend a lot of time when Angela is out trying... Read full Story
shemale lover 2012-12-08 4,554 sucking Lingerie kissing
94%
Becoming the girl i really am part 2!
I smiled up at my best friend, dressed up in sexy lingerie and smiled, "Can i dress up too?" i asked in a hopeful tone of voice. "Oh, wow, really? Yea sure!" brian answered with excitement in his voice. "Go into the guest room, my sister keeps all her clothes in the dresser ... Read full Story
shemale lover 2014-06-11 5,467 first time shemales cum
87%
My first time with a shemale
My girlfriend had been out of town for a couple of weeks and i was so horny and wanted to get upto something kinky. I called a shemale site from la costa del sol called taiakshemales and arrange to meet one of the beauties. I was very nervous as i drove to her house as i never touched a dick befor... Read full Story
shemale lover 2011-11-07 3,997 anal shemales Fetish
87%
David Invites JoJo Over
Although I fucked Del that night, for the first time in our marriage I was thinking of someone else. I just couldn't erase the image of our sexy neighbor lying bound and helpless on our bed wearing the very same peignoir set that Del wore when I took her virginity on our wedding night. As I lie awak... Read full Story
shemale lover 2012-07-27 3,400 Cumshot Lingerie oral sex
100%
Slut bi cross dresser
Party Surprise - First sex as a Crossdresser. This is a work of Fantasy. I hope you enjoy. Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed ... Read full Story
shemale lover 2012-11-24 4,506 anal first time cd
80%
Crossdressing fun
I always love to crossdress when Im horny I love the feeling of being a woman and seducing a man. Older men have always attracted me here is my fantasy. I dress up one day with a red thong red bra black nylons short skirt and blouse and get online. I find a man who likes me and is ready to play. I c... Read full Story
shemale lover 2014-11-07 3,836 first time shemales Masturbation
85%
Home alone, at last
At last, home alone for a while ….. So, I managed to have a whole day home alone. My life is quite complex with people arriving and leaving regularly, then there’s me being away for short stays whilst I’m working so being home alone can be difficult. But the problem was that... Read full Story
shemale lover 2013-05-16 5,062 Stockings suck cum Lingerie Homemade
50%
Been dreaming this for a while...
Been imagining an encounter with a hairy tall man, Been masturbating while I crossdress. Still a virgin analy but it might not last for long, an encounter will soon be coming. My perfect night would be this... Tall man ebters my hotel room, we talk, I am fully dressed in lingerie, black! High ... Read full Story
shemale lover 2015-11-15 2,324 first time shemales gay male
62%
Fifi La Femme: A Pansy at Last
I was quivering and shimmying with excitement dressed in my wife Doreen's black satin 36DD long-line brassiere with a pair of heavy silicone false titties wobbling inside the cups; her gorgeous deep six strap waist clinching suspender belt and flimsy see through panties that I'd bought for her; or r... Read full Story
shemale lover 2012-07-28 5,320 first time cum oral sex
88%
Caught Crossdressing by a Real Man
This story is a continuation of night club cum slut. Ever since I first wore panties for a boyfriend, I had built up a collection of lingerie. I gradually worked up from panties to the most erotic lingerie I could find. My fascination with cross dressing went a little further with a new fetish f... Read full Story
shemale lover 2013-01-17 35,342 Crossdresser sucking Lingerie ass fucking ass fingering
50%
Punished for Cheating
How my life had changed in the two months since I had taken in Caroline as my lodger. The arrangement seemed ideal at first – I was a newly divorced male and she was a single girl. Of course, I should have foreseen that the 30 year age gap might present a problem but that is the wonder of hind... Read full Story
shemale lover 2013-03-05 6,084 Crossdresser Lingerie domination cd humilation
100%
Tranny Night Out
Tranny Night Out and One Kinky Session Guess I should start by explaining myself, as a young guy I always knew I was not the same as a lot of my friends and enemies for that matter, girls had no interest in me at all apart from ones who were long term friends. I knew something was wrong but neve... Read full Story
shemale lover 2013-05-01 7,651 Stockings suck Lingerie ass fucking stroking
55%
Lola Spais my story
Since childhood, feel girl, i scruple boys, i wanted to wear a skirt. at school wear women's panties and bras - it's very exciting. in 20 years I slept with a guy, I was hurt and did not like. I left the girl in her room, began to create his image, have fun,me wildly excited my body .... Read full Story
Lola Spais 2016-10-18 3,639 Crossdresser Ladyboy Lingerie sissy