Sort by
Relevancy

Free Stories

70%
His first anal!
Andrew was a very simple guy. He was not aggressive, very quiet and nice. Actually he was not quarrelsome, just a man of peace. But we all know that still waters run deep. Over the past few years, Andrew had longed for being penetrated. Vehemently. He needed to be bent over something and fucked thor... Read full Story
shemale lover 2014-05-09 8,566 anal shemale jerking off
50%
sine qua non: anal/vaginal pleasure
One thing's for sure, my desire is to be fucked and to fuck... And it's in this order of things that I've been wanting to fulfil my fantasies for the last two years. I'm not too fussy about choosing my partners, but luck has always smiled on me when it comes to finding the right one. However, over t... Read full Story
hippocampus_171 2024-04-05 1,508 anal solo Amateur Mature big ass sissy femboy
91%
How I learned the pleasures of anal
This narrative is the journey that lead up to my first experience with anal sex. The details I have here are as accurate as I can recall and any dialog is essentially the best of what I can remember now. It of course gets more sexually explicit and graphic towards the end... I was born and grew u... Read full Story
Dressed2Thrill 2015-07-29 9,793 anal first time Amateur virgin cd
100%
First Cross-dressings Loosing Anal Virginity
It happened after a month of me blowing that guy twice...I mean I was so damn excited and was craving for his cock....I was blowing him every weekend in his car after the school...his cock was almost 7 inches and was so thick and that I like so so much the gagging he was giving everytime, that chock... Read full Story
Trapbomb1 2022-07-29 6,421 Teen (18+) Crossdresser Bareback Creampie Blowjob Big Cock virgin virginity sissy cum in mouth double anal sissy slut virgin ass
50%
Towel Boi: You're Hired
Kasey Stevens woke up in his new studio apartment. The five-foot-nine, blue-eyed sissy with ash brown hair yawned and stretched before heading into the bathroom. He showered, taking good care to lather his rosy skin with strawberry scented body wash. He shaved his legs and rinsed off. Then, he appli... Read full Story
Faggyboi and Puzziboi 2023-11-14 5,504 anal Small Tits Crossdresser Amateur Bareback Blowjob Guy Fucks Shemale Interracial small cock big ass femboy
66%
Anal Queen
Amanda fell to her knees in the darkened theater and slowly unzipped my pants. My cock throbbed. As she pulled down my underwear, I felt my manhood spring forth. Amanda took the whole sausage into her warm, soft mouth. I could barely see her face in the darkness, but I could feel her between my l... Read full Story
shemale lover 2012-11-24 5,930 tranny anal sex Cumshot cum swallowing
100%
1st time anal
JOURNAL ENTRY 2 MIN READ My 1st anal As with most of adventures in the early days its starts with fun night at the bars. Getting a good buzz on and putting an ad on Craigslist. (Rip🙁). I was especially worked up and really wanted some cock. I had been having some fun over the last Few months since... Read full Story
Rachelcdfun 2024-05-08 453 anal cumming crossdressing cd crossdressed
100%
My first anal
This was a couple years ago, but I still remember it very well. I was insanely horny one night so i signed up for a sex dating/chat site. I'm siting around, rejecting chat invites from guys, thinking I'd never want a cock. After a while, I decided to try chatting up a guy, see what kind of stuff ... Read full Story
shemale lover 2012-02-24 4,503 first time anal sex doggy style
100%
Bi male and anal sex
Thru out my adult sex life I have always enjoyed having my ass teased and played with. Then I started dating a woman whom loved to tease a mans ass with her fingers, yes fingers where she quickly got me use to taking 2 of her fingers. Then one night things changed. After a hot night of wild sex,... Read full Story
shemale lover 2012-10-10 5,118 anal sex cum jerking fingering
80%
Bisexual Black Man's Paradise
The name is T.J. Brown. I'm an engineer working at Walpole, the toughest correctional facility in the state of Massachusetts. My days are spent reading books, exercising and occasionally tussling with other workers. The facility is undergoing some expansion and I'm the lead engineer on this gig, wor... Read full Story
shemale lover 2012-06-24 5,132 big dick tranny anal sex Cumshot orgy facial oral sex
100%
A Perfect Pandemic: A Transsexual Transition in a Troubled Time
A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... Read full Story
the greatest liar 2021-11-16 4,706 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
66%
Dance Bar Bathroom Slut
Dressed in extremely short cut off blue jeans shorts that showed my ass cheeks, 4-inch red heels, a red tank top, a sports bra, way too much make up and a blonde wig, I set off for Atlanta. "Black guys love trashy blondes don't they?" I thought to myself. I checked into an Atlanta hotel... Read full Story
shemale lover 2012-06-06 2,818 anal oral facial glory hole
78%
Anal Therapy
My new psychiatrist wasn't at all what I expected. When I saw her name in the phone book, I pictured a dowdy old lady wearing a long, gray skirt and flat-soled shoes. What else could Dr. Edith Doss look like? I got my answer when a tall, leggy redhead stepped into the waiting room. A tight, black... Read full Story
shemale lover 2012-11-24 7,498 anal Fetish cum crossdressing
100%
Hung Alessia Travestita meets MILF
Hung Alessia meets MILF with Giant Clit Several days ago, Alessia a beautiful English Transvestite met a tall slim sexy Canadian woman named Sandra on the internet. They were captivated with each other's nude bodies and genitals. They immediately engaged in a video sex session together. Sandra fu... Read full Story
darrell 2023-08-13 3,788 anal Big Cock deep throat cock sucking milf fisting pierced cum shot muscular big clit Swallowing Cum Hard Body
76%
Sissy Mailee's first black cock
As long as I could remember I have always had a craving for black cocks. My first time was a few years ago after partying with a friend of a friend. I had called up one of my CD friends, Suzy, to attend a Halloween party at a local warehouse. We had agreed that we’re both going to the party... Read full Story
shemale lover 2011-11-06 6,990 anal first time shemales
100%
Shemale on wheels tour
Being a sexy naughty city girl like myself…I get allot of attention from the boys. I always enjoy getting the attention of the small town boys that are not used to seeing a sexy bitch like me roll though town. They jerk off to girls like me online all the time. But having me right in front of... Read full Story
shemale lover 2012-05-17 3,362 anal sex fingering domination oral sex facefucking
100%
First Time With My Best Friend
My friend John is really sexy. He is tall and blond with a lean strong body. I have often imagined what it would be like to have his sweet cock between my lips, or between my virgin buns. He’s too good a friend though, and I’ve never had him give me any hint that he might like to be with... Read full Story
shemale lover 2012-10-30 6,557 anal first time Fetish crossdressing
100%
A Win-Win
A Win-Win By Sabrina G. Langton *** Author's Note: Hi, just a quick, crazy story about a wife actively participating in her CrossDresser husbands sex life. Just a bit of fluff, hope YOU like it.) *** We were laying in bed, sex was done, my wife could now relax for the rest of the month ... Read full Story
Brina Giselle 2024-03-31 2,009 anal Stockings Crossdresser Blowjob pantyhose kissing salon
100%
Jesse’s First Day
Jesse didn’t want to be late on his first day so he got to the office about 20 minutes early. He was looking sharp in a black suit pinstriped in light blue. The shirt matched the pinstripes and the tie was made up of reds, purples and a little of the light blue to bring it all together. Jesse ... Read full Story
shemale lover 2012-05-16 5,219 hardcore anal sex Cumshot
100%
The switch
HI have been married for 12 years now. Trim and dapper, this 35-year-old's marriage was satisfactory enough and I played the role of husband well. Sex with the wife was still good, with both making out at least once a week or on rare occasions, once monthly. Twelve years on in this heterosexual rela... Read full Story
shemale lover 2014-10-11 8,054 anal shemale jerk off
100%
One experience with two black men
Hello again this is EvA…I am a 40 year old tranny. I do not consider myself a cross dresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine lady boy. I have been taking also hormones for 4 years, on and off and I already saw many changes&h... Read full Story
shemale lover 2013-05-16 4,255 Stockings anal sex suck threesome Interracial cum swallowing
80%
Chastity and its effects
I actually thought of writing this for some time now, this quasi-scientific testimonial and reflection about chastity. Now, I finally had some time to reflect, gather and compare info and experimentation from personal experience about the topic. More specifically, the effects it has on the mind and ... Read full Story
DoraTV 2023-02-09 5,527 Crossdresser anal play chastity sissygasm Sissyfication story chastity orgasm
50%
Next Phase - sequel to Continuing to love the feeling
Now I would like to have both of you engage in some light bondage, how do you feel about that? Maggie quickly replied, I'm up for anything and since Sheri's my Bitch she'll do as I say. Ok then, let's get started, Linda , please come over here and let me strap you into my special sex lounge.... Read full Story
shemale lover 2011-12-08 2,600 anal oral domination
34%
my female spouse cought me on bed taking a black cock
I cross dressing & son of my landlord loves me specially on bad. he dosent like to talk to me , he needs me only to satisfy his lust. I m ok about that as he is tall, dark n handsome & he has huge thick cock mmmmmm.I love him so mad for that.one day he called me to see if I m available for h... Read full Story
shemale lover 2014-03-09 5,173 anal shemales Group Sex
100%
Showroom Part 3
While driving from the park back to the car dealership we expressed relief that the park maintenance folks hadn't arrived a few minutes earlier. What a sight they would have had seeing a beautiful woman massaging her breasts while the guy in the car with her sucked her cock. Laughing, I said, "... Read full Story
shemale lover 2011-09-14 2,061 anal cum nipples
50%
Taping a Train
Ever since I took the leap and became and transformed my body into the one I was supposed to have I have never been happier. I love my soft skin, long dark hair. When ever I can I will look in my mirrors at home while naked and rub my hands up and down my body, feeling my big D cup breasts then runn... Read full Story
shemale lover 2012-04-12 2,883 anal Cumshot Uniform gangbang oral
75%
It started w/the neighbors wife then her husband
About 5 yrs. ago on new years I was invited over by the neighbors to party, they had some friends over; we were getting plastered and eating food celebrating the New Year. When out of the blue in front of her husband and friends the wife starts kissing me, I gently pushed her away not knowing how th... Read full Story
shemale lover 2012-06-02 3,803 anal sex Fetish oral fingering crossdressing
88%
My very first experience with my classmate
He was amused by the sight...of me in lingerie..standing on the porch,it was obvious he was in a shock (or state of extacy?) and couldn't take his sparkling blue eyes off my firm body inside the dress...he closed the door behind,like he was worrying if someone could see us ..I don't know why but i f... Read full Story
shemale lover 2012-10-01 3,788 anal first time Creampie
100%
Fixing The Car Chapter 2
As I had mentioned in the first story about my adventures with my friend Ross and his wife Barbara, that the rest of that first story would be continued and so here it is. After I had cleaned all of the fuck juices from Ross's shrinking cock we all laid back on the bed to rest and I started to th... Read full Story
shemale lover 2012-11-08 2,335 anal sex cum oral sex
50%
Magician's Assistant - Friends & Lovers Part 10
Magician's Assistant - Friends & Lovers takes place in the Magatrix the Magnificent Universe, which was first introduced in my serialized seven-part story, Magician's Assistant. The premise upon which both that story and this story are based revolves around the fact that Magatrix the Magnificent... Read full Story
shemale lover 2011-12-26 3,820 anal erotic encounters erotic
83%
My new life
It started 3 yrs ago when I was 19. I had just graduated HS and was off to college to study arts. At first college was great but I wasn’t making many new friends and felt kind of lonely away from home. Then I met Charles, he worked at the local coffee shop and we began gaming and hanging out. He ... Read full Story
Sissy Vikki 2022-11-08 5,986 anal Cumshot bdsm cum gangbang bondage black cock fantasy slut sissy chastity Sissy story
100%
delicious virile male flesh
Tasted delicious virile male flesh… The breeze caressed my swollen nipples giving me pleasant shivers. The two glasses of Riesling had also contributed to my excitement. My crotch was burning as if the disappearing sun had blown all its thermal energy into me. Under my fine lace panties, purple o... Read full Story
hippocampus_171 2023-04-23 4,706 anal Small Tits Amateur Creampie Blowjob Mature small cock big ass feminisation cum in mouth gaycd virile
33%
Duel With the Devil, Chapter 20 of The Greatest Liar
Duel With The Devil This is a work of fiction. All characters (including the narrator), celebrities, places, residences, neighborhoods, restaurants, legal agreements and proceedings, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any r... Read full Story
the greatest liar 2023-07-19 3,856 anal Bareback Creampie Ebony Guy Fucks Shemale post-op celebrity post op sex
80%
My First Time with a Transexual
I was in a large city about 100 miles from my home for a week on business. I had been hitting the bars for a few days with out a lot of luck. On the way back to my hotel afer work one day I picked up a few of the alternative newspapers/sex ads. Checking the ads out later I saw women, men and transex... Read full Story
shemale lover 2014-03-15 9,167 anal shemales
67%
The New Boss
My name is Jacklyn. I am 27 years old and was just promoted to Vice President of BB last week. I'm not a stunner but I have an okay body with a nice shape to it. I begin working here when I turned 20 and found it to be relaxing. However what everyone called the "Upstairs Crew" were very qu... Read full Story
shemale lover 2014-03-19 6,917 anal threesome trans
85%
Perfect combination
Mary had always preferred to go out with girls rather than men. She found girls were more gentle and kind and loving which is what she liked from a relationship. She found that men tended to treat her badly and did not satisfy her in bed either. She was not in a relationship at the moment though, ha... Read full Story
shemale lover 2015-11-23 3,742 anal licking oral
90%
My Shemale Webcam Tube Date With A Sexy Shemale
I was rushing back home from work because I was suppose to have a date via shemale webcam tube with the sexiest shemale I had ever seen. We met few nights ago and I could just feel the chemistry between us getting stronger. I entered my place, dropped my things on the sofa and turned on the lap-top.... Read full Story
shemale lover 2015-12-29 3,843 anal suck Masturbation
72%
Sexy She Male Pic And One Passionate Night With Hot Jeff
I am stunning, but I had some difficulties so I was determined to keep my secret. However, I have found a way to express myself, and that's how I met Jeff. I posted my naked she male pic online and started having date invites almost instantly. They were all pretty perverse, and I didn't mind, but I ... Read full Story
shemale lover 2016-02-08 3,374 tranny anal sex Creampie
42%
Shemale Free Chat And Sex Adventures
It was another day at work at the mall. Being a security guard wasn't exactly the most exciting job in the world: I'd sit all and maybe get a few calls about some punk kids trying to steal DVDs. I felt like my talents were wasted there - I used to be a competitive bodybuilder, evening getting into f... Read full Story
shemale lover 2016-04-24 3,679 anal transsexual ass licking
66%
My Shemale Cams Extravaganza With The Boys
It was a beautiful late night and I decided to take a stroll home after work. Home was literally about 10 minutes away and I loved the feeling of the late night breeze in my hair. The day was long and daunting. All I could think about was the shemale cams videos I viewed while at work. While most... Read full Story
shemale lover 2011-08-11 2,717 anal sex Creampie shemale
100%
Wish cum true
My wife and I have had a strong and open relationship from the start. We have accepted each other and all our wild passions, and we have always been open about our sexual desires. Having said this I will try to express what happened the other night with the same intensity I experienced. I came ho... Read full Story
shemale lover 2011-09-26 6,127 anal first time shemales
90%
Taken to be a Shemale Lover
I had went to work at the burger joint, when the manager informed me that 'I have too many people on payroll today, I need you to clock out and leave.' This is what happens when you work for a fast food joint, all the kids that go to school and can get a permit flock to the fast food places. At leas... Read full Story
shemale lover 2011-10-25 3,785 anal shemales asshole
83%
Night With A HOT Sissy!
June 28th, 2009. End of senior year of high school. I, Angus Corleon, actualy graduated. I wasn't a model student. I've been a leather jacket wearing, rebel rousin, beer drinkin, hell raisin son of a bitch since middle school. My parents didnt care about me, after all my brother is a cop and my sist... Read full Story
shemale lover 2011-11-23 2,686 anal shemales gay male
88%
My tranny slave
My biggest wish is to own a tranny slut a cheap worthless little cumwhore. Is make wear stocking suspenders a short skirt and black lace panties. I would rule her with an iron fist. First I'd make her crawl on all fours like my lil pet I may even keep her on a leash. She would be forced to obbey my ... Read full Story
shemale lover 2011-12-09 2,454 anal shemales bdsm
57%
My Neighbor Took My Cherry
I had a neighbor who was a beautiful lady at my apartment I lived at in town. Her name was Sally Williams. She was 25 and she was 5'9" weighed 128 lbs had 30 c cup breasts i would guess she had dark brunette hair down to her back and amber eyes. She called me over and asked,... Read full Story
shemale lover 2012-01-15 27,721 anal shemale cum
100%
X-dresser Turns Housewife
A friend of mine that I have been seeing for a while shocked me one day. He called me up wanting to know if I was free throughout the day. I told him I could make time and he invited me over to his place. He told me to wear something a housewife would wear and bring an apron. I didn't know why, but ... Read full Story
shemale lover 2012-02-04 2,496 anal sex crossdressing
50%
Carol, The Saga Continues
It's very late Monday night as Carol returns from the date that J C had forced her to keep, she places her purse on the hall table, throws her jacket over a chair and walks toward her bedroom. She can't wait to shed this clothing that J C demanded she wear. As she walks, her feet, clad in the five i... Read full Story
shemale lover 2012-03-09 2,560 anal sex shemale deepthroating
83%
My Lady Boy Lover
I met Joliet through a mutual friend, I was the featured receptacle for the evenings generous donations of tyranny spunk. The evening was one to remember and where I met Joliet, Joliet is about five feet eight and one hundred sixty pounds well built like a sculptures dream. Light skinned and toned... Read full Story
d4david 2012-03-29 3,007 anal sex Creampie shemale
100%
I slept with Joanne, who had a dark secret
What is the weirdest sex I have had, I thought about is for all of thirty seconds, the night Joanne slipped inside me, on a fucked stopover. Now before you cry Lesbian or Bi-Sexual, you would be wrong, because Joanne was neither, she was a transsexual, something I did not know at the time, nor was ... Read full Story
shemale lover 2012-04-11 2,554 anal sex orgasm oral sex
100%
T*Girl at the Bus Stop
That was when I made my decision. I turned the wheel sharply and drove into the gas station just behindher. I turned off the engine and hopped out of my Mustang. I walked upbehind her and leaned down. She still hadn't noticed me ,I guess,so I whispered into her ear, "Need a ride?" Sh... Read full Story
shemale lover 2012-05-05 2,762 anal sex Big Tits deepthroating handjob
100%
A Crossdressers Tale
Hi, my name is Ron. This is a story about the first time I dressed for a guy. I was off work that day. My wife was at work & my daughter was in school. I was bored and got online for for something to do. I have a yahoo screen name letting people know I'm a CD and bi. Well, this guy I've been tal... Read full Story
shemale lover 2012-05-12 2,124 first time anal sex Fetish crossdressing
100%
Through The Studio Window
November had arrived once again. The long days of summer were now firmly in the past. I contemplated such situation as I walked home from work. I changed my route recently to walk passed a ballet studio. There was a vision of beauty training on her own in that studio. Long legs, supple body and blon... Read full Story
shemale lover 2012-05-19 2,162 anal sex Blowjob
100%
My first stranger
I practiced dressing hundreds of times before I went out in public. I went out in public dozens of times before I tried to pick up someone. I wasn't attracted to gay men - I liked men who appreciated me for my feminine side, so because of that I only wanted to be with a straight guy. Obviously this ... Read full Story
shemale lover 2012-06-15 2,019 anal Cumshot oral sex deepthroating crossdressing
100%
Black Transsexual Power Play
The name is Christopher Jean-Bertrand. I'm a young Black man of Haitian descent living in York, a town located right outside the City of Toronto, Province of Ontario. I currently attend York University, where I major in Civil Engineering. Yes, I'm a deeply intellectual kind of guy. We have those in ... Read full Story
shemale lover 2012-07-11 2,968 anal tranny Creampie Ebony
100%
Chrissie and the Professor
Possibly the after hours engagement with an English Literature professor at college may have been the thing that convinced me that older men might be more to my liking. It was during my Junior year at the university when we were discussing the poetry of Arthur Rimbaud, the French poet, that I beca... Read full Story
shemale lover 2012-07-25 2,835 anal oral facial
33%
Bottom Kim
Kim was tied down and helpless. She was stretched out on her back on the bed, with her hands tied over her head to the headboard, and her legs secured with a spreader bar. She was blindfolded, and had a phallic ball gag in place in her mouth. The lights were low in the room, not that she could re... Read full Story
shemale lover 2012-08-13 3,281 anal sex Masturbation fingering