Sort by
Relevancy

Free Stories

62%
Naples
I had been at sea about a month when my ship pulled into Naples, Italy. The only action I had seen had been slipping away to my hiding place on the ship to jack my dick on a regular basis. I was ready to find some Italian pussy. I was slim about 6' with blonde hair and a fat 7" cock that ... Read full Story
shemale lover 2011-12-16 6,654 Teen (18+) shemale gay
80%
Becoming Alanna Part 2
Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work wit... Read full Story
shemale lover 2012-07-12 4,040 sucking Fetish Ladyboy rimjob
80%
Alex pt. 3
After that b****** in the bathroom, me and Alex hung out a couple times. we went to a bar, and I ordered a beer, Alex had vodka and cranberry. I didn't want to get too drunk, because whenever I do I can't seem to get hard. Of course, I knew all along that somehow that night I would finally... Read full Story
Mike212 2018-07-02 6,292 Teen (18+) Blowjob Big Cock Ladyboy Guy Fucks Shemale Frottage Homemade
100%
Cum is a Cross-Dresser New Drink
Nikki looked up at me with her big, brown eyes as her head bobbed on my cock. Nothing was quite so sweet as one of her blow jobs. She had this way of dragging her tongue along the underside of my cock that made me want to cum in seconds. I always tried to hold it, but Nikki wouldn't let me. When she... Read full Story
ASSEaster5678 2018-09-14 6,731 Crossdresser Cumshot Ladyboy cum in mouth
100%
Casino Girl
I had been working as a casino dealer for several years and would occasionally meet some very attractive women and chat. Asian women have always been attractive to me, whether the exotic appearance or maybe because my Mom was Pacific Islander, and a lot of people thought I was Asian. Mia was a bit... Read full Story
Jon Paul 2022-01-03 3,125 Stockings Cumshot Bareback Blowjob Asian Ladyboy Guy Fucks Shemale
100%
Becoming addicted to her she-cock
"I'm going to make you a very happy woman tonight when I slowly but firmly slide my long, thick, hard she-cock all the way up your tight virgin ass tonight baby" Alma whispered in my ear as we left the bar I had ?mistakenly? stumbled into. I shuddered with both fear & a bit excitement. I don't why ... Read full Story
Curious_billy 2023-05-07 7,740 Teen (18+) Amateur Cumshot Asian Ladyboy domination Homemade cum in mouth
100%
Being a shemale's toy can be fun
Joliet called and asked if I would be interested in having some fun...I thought about the last time and how pissed off she got. I hesitated long enough for Joliet to whimper in the phone 'I promise to make up for my last theatrics, no bondage and I will reward you very handsomely if you attend to my... Read full Story
shemale lover 2012-02-10 4,022 anal sex Ladyboy facial
95%
How I became a cute femboy CD part 2
The game of husband and wife Kevin and I played went on for a little over 2 more weeks before we decided to go even further, I say we but it was Kevin who seduced me into it. We got together in our game as much as we could and it was a lot. I would always dress for him in various outfits and my ... Read full Story
Cute_Femboy 2016-04-05 12,597 first time oral sex nipples crossdressing cd sissy
90%
How I became a cute femboy CD part 4
My legs finally started to work again and I turned and was about to walk to my bedroom when Kevin’s voice stopped me. “Come on, Natalie, you know you want to. You have been crushing on David ever since he moved here.” “You’re an asshole, Kevin. You know that. You are a total asshole! I tho... Read full Story
Cute_Femboy 2016-04-05 12,705 first time cumming crossdressing cd sissy cumshot in mouth
100%
Sissie Slut's Windows of Womanhood
I flash back to my first time with a grownup adult at the tender age of16 . I was so nervous now that we were here in the motel room. I was nervous for so many reasons. I lied to my family and told them I was staying at a friend’s house. Instead, I'm here with Mr. Joey in a motel room and he was my... Read full Story
Regina10 2021-02-22 6,874 Crossdresser Bareback Creampie Fetish Blowjob blonde Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth double anal
100%
Becoming a Chrissy - Chapter 1
I always knew I was a little sissy slut. When I was ten, I took a pair of my mommy’s panties to try on. It was a hot pink G-string that my petite mother must have worn when she was ready to get fucked by my daddy. It was just the right size to cover my prepubescent clitty and also stretch through my... Read full Story
mindlessrobot45 2024-05-13 4,269 Crossdresser Blowjob blonde femboy cum in mouth
93%
Lakeside Awakening
If anyone had told the way I'd meet my soul mate a few years ago, I never would have believed it. It was my senior year of high school and I had recently gotten out of yet another bad relationship with a girl. Lina had been a pretty, chubby blonde with a nice personality but a nasty temper. We ... Read full Story
AlliV 2014-09-02 6,792 tranny ass Teen (18+) Big Cock jerking
73%
My night with my Black Master
I posted on this site i would like to be a blackmans sissy,i did get a response from a guy who said he was looking for a white sissy to use i told him i was 55 and never done this before but i would love to be his sissy for a night,we arranged to meet at a holiday inn on the M6, we meet in the bar h... Read full Story
bigtranslover 2013-12-29 7,796 first time shemales interracial sex
85%
Came to play
I spent my childhood at my grandmas house while I was growing up, there was several kids in the neighborhood... I basically grew up in the ghetto side of town. I knew more black people than white. I went to a school where there was always atleast a fight a day, so I kept to myself for the most part.... Read full Story
shemale lover 2011-11-29 3,331 first time shemales interracial sex
81%
Husband and wife used by Mr. Big Black Cock
We had decided to take a trip to Vegas and spend some alone time together.. We started off with dinner, then went to hit the tables.. My husband was on a winning streak. He was up at least $1500. I whispered into his ear have fun I'll be in that cute little shop. ok? Then his luck ran out.. and befo... Read full Story
shemale lover 2011-12-18 8,113 shemales gay male interracial sex
90%
Used Like A BBC Whore
About a year ago while living in a hotel and living there as a Transexual I was used by a young black man as his whore for the night. He moved in about two weeks ago with a couple friends. They where maybe 5 rooms away from me on 1st floor. As the week wore on I would be coimg and going and would... Read full Story
shemale lover 2012-10-19 4,580 anal Cumshot oral Interracial
96%
The Backdoor
It was only my first time in the club and my hands were shaking beyond control. I almost didn't make it through the front door I was so nervous. I felt so out of place. Everywhere I looked, it felt like people were staring at me, judging me. It was like they knew I had no clue what I was doing. ... Read full Story
shemale lover 2013-01-03 16,860 sucking Shemale Fucks Guy Blowjob Big Cock Interracial
84%
My Black Transsexual Goddess
Another day in the City of Ottawa, Ontario. Gosh I am bored. I walk through the corridors of the Carleton University library, yawning and stretching at the prospect of an all-nighter because my take-home midterm is due in the morning. As I make my way to my usual spot on the second floor, a wide-eye... Read full Story
shemale lover 2013-02-21 8,491 hardcore sucking Guy Fucks Shemale Interracial bbw
100%
TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
SpankydeBautumn 2021-02-22 3,890 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
80%
Amber
The summer after high school I moved into this cheap hotel downtown. I'd been working in the mailroom for a large company, and really needed to get my own place, but I didn't have much money. I also wanted to have more time to play dress up. It was an old building that had seen better days. I ha... Read full Story
ambersissy 2021-04-23 5,625 Crossdresser Amateur Big Cock Guy Fucks Shemale Interracial cum in mouth
50%
DATES NUITS
My wife, Denise, and I have been happily married for over 10 years. Over the years, we have enjoyed a vibrant and adventurous sex life. As we've grown in our marriage, we have become very open and honest about our sexual fantasies and desires. Through the years, we have come to realize that my w... Read full Story
Femboy 2021 2023-02-07 1,596 Stockings Lingerie Shemale and Girl Guy Fucks Shemale Interracial Sex Toys cum in mouth
100%
Fender Bender Chapter 2
The bright sun shining through the window woke me up, for a moment I was confused and disoriented. Then it all came back to me. I had sex with Mark and Susan James last night and I was still wearing a pink baby doll nighty and matching panties she had given me to put on before we went to bed. I w... Read full Story
shemale lover 2012-07-26 4,499 Teen (18+) Fetish crossdressing
100%
Pretty Woman
Tyler was as nervous as anyone could be. Hazel eyes darted for the door as silky black stockings slid up smooth white legs to meet garter straps attached near lacy white panties. Next came the bra, straps catching on skin slightly sticky with perspiration. Heart pounding as the black pencil skirt gl... Read full Story
shemale lover 2012-12-22 8,946 Stockings Teen (18+) Crossdresser sucking heels
95%
Proud To Be A Sissy Chapter 8
I woke up to hear daddy lightly snoring and in my sleep I had draped a leg over him so that my body was almost covering him. I giggled to myself realizing that even in my sleep the sissy slut in me reached to grasp his flaccid penis. Then I curled closer up against daddy and contemplated about how m... Read full Story
shemale lover 2012-12-24 9,463 Teen (18+) Crossdresser Uniform Lingerie domination
100%
Josephine's First Day
My life at school was fairly uneventful. I wasn't brilliant academically. I wasn't a talented sportsman, actor or musician. I wasn't one of the popular children. I wasn't in physical fear from bullying, although there was a lot of teasing, name calling and 'jokes' that were funny for everyone else. ... Read full Story
shemale lover 2013-01-04 8,999 Teen (18+) Crossdresser sucking Uniform handjob
83%
How i became a sissy/my first blowjob
I'm a 17 year old sissy now but i started crossdressing 4 years ago when i was 13 :).This is the story. One day my parents went to our lake house for the weekend with my s****r but i was feeling sick so they left me with my grandparents. They were taking care of me for a day or two and i got better ... Read full Story
shemale lover 2013-08-09 54,140 Teen (18+) Crossdresser suck oral cum swallowing cd
81%
Bimbo Barbiex
Ooh hiya boys, I'm Barbie Leigh, a naughty little bimbo tranny, 19 yr old, 5'7" tall, blond, blue eyes, slim and tanned with a hot curvy ass. I have been dressing as Barbie since I was probs about 16 and I'm very well versed when it comes to horny guys and how to please them.lolz... Read full Story
Barbie Leigh 2013-12-08 4,531 tranny ass Teen (18+) sucking rimming
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 19,475 first time suck fingering Lingerie ass fucking cd
84%
My Little Queen
I worked at a school in the northeast years ago and there was a longhaired emo boy, chubby and shy with a sweet ass. who was always giving me the eye in the halls. I made no mistakes or untoward moves but would catch him with his shirt up a little to show me he was wearing panties, or see him eyeing... Read full Story
Giantsquid 2016-10-05 12,825 Teen (18+) Blowjob cd
87%
Chicago TG Romance (part 2)
As you must read part one of this story, one of the most interesting and attractive T-girls I have met is sleeping beside me in my motel room after a wonderful evening of being together. Beth awakened around 4am and got up to go to the bathroom. She was brushing her teeth and heard me stirring, I di... Read full Story
Jon Paul 2018-06-04 6,187 Amateur Shemale Fucks Guy Blowjob Asian Ladyboy Ass to Mouth cum in mouth
100%
Florida TG Experience
I had known Jan from High School, we always had an attraction for each other but were dating someone else or married at the time. Jan had actually married a friend of mine and I was envious of course. She at that time had sandy blonde hair, and a body to die for. One evening we had them over for dr... Read full Story
Jon Paul 2018-08-13 11,333 Group Sex Big Tits Bareback Creampie Blowjob blonde Asian Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth double anal
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 10,127 Teen (18+) Crossdresser Amateur Masturbation Bareback Creampie Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth cum in mouth
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 5,132 Teen (18+) Amateur Cumshot Masturbation Bareback Blowjob Big Cock Uniform domination Homemade pov Ass to Mouth cum in mouth
100%
Sissy Slut Reunion
Rob had moved back to town and called me. He had just moved into his new place and he wanted me to come by and talk. I knew what he really wanted from the tone of his voice, because I wanted it too. He said he had been thinking and dreamed about me the whole time he was away. My spirits lifted and ... Read full Story
Regina10 2020-09-14 4,415 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Cheating Sissy Wife chapter2
My sweetheart Keith is back from his road trip and we were about to make up for lost time. He didn’t even want me to fix dinner. Instead he said that we would order pizza later. Meanwhile we started making out right there on the couch. We were both horny and anxious to get next to each other. I felt... Read full Story
Regina10 2020-10-26 5,027 Crossdresser Big Tits Cumshot Bareback Creampie Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth
100%
I need some advice
I’m so emotional today. I haven’t been able to spend quality time with my bf in weeks. Let me explain. Me and my girlfriend both work from home now so I haven’t been able to get away for long to see my side nigga. Today was supposed to be the day we actually got to spend the day together. My girlfri... Read full Story
Wet boy kitty 2021-02-01 2,677 Crossdresser Amateur Cumshot Masturbation Bareback Creampie Ladyboy Lingerie Ass to Mouth cum in mouth
75%
Aunt trip
In 2013, after almost three years of service in Afghanistan, George Madsen, a gay Royal Navy communications petty officer, retired. His experience in the distant deserts had left an indelible mark, the memories of friends lost and challenges faced still burned vividly in his mind. Coming home was n... Read full Story
Rebba 2024-04-25 3,651 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
100%
Sissy Boy’s Secret Desire || Part 6
The room was heavy with the scent of sweat and submission, his body still trembling in the aftermath of what felt like total surrender. She lay beside him now, her presence looming, both comforting and intimidating. He had given her everything—his control, his dignity—and yet, there was an odd sense... Read full Story
shemale_club 2024-10-04 993 Stockings Small Tits Crossdresser Masturbation Fetish domination Sex Toys small cock sissy femboy hentai teen (18+)
100%
Inmediatamente despues
Luego de que el termino en mi nalga, todavía con la sensación de placer que teníamos los dos, me beso tiernamente y me pregunto donde quedaba el baño. Yo todavía de rodillas en el sofá, pase mi mano izquierda sobre mi nalga y sentí el semen que mi macho había depositado sobre mi y lo trate de recoge... Read full Story
maritza_tv 2023-04-28 1,644 anal Crossdresser Amateur Creampie Big Cock Ladyboy Lingerie Guy Fucks Shemale Interracial Mature Homemade sissy femboy
100%
Lettera a Cristina (bocca di rosa)
Beh, e' bene che tu lo sappia. Ero io quel 40enne che hai incontrato in metro'. Avevo, per la precisione, 39 anni e 10 mesi. E, ti sbagli, non stavo scrivendo proprio a nessuno, cercavo solo l'applicazione della telecamera per riprenderti con un filmino o scattarti delle foto per averti anche dopo... Read full Story
Sexbit 2023-08-22 904 tranny Cumshot Outdoor Blowjob Ladyboy femboy Vintage cum in mouth teen (18+)
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 4,052 Teen (18+) Ladyboy redhead Guy Fucks Shemale Interracial Ass to Mouth cum in mouth
80%
How it started
What got me started off watching shemale porn was actually meeting a very beautiful shemale at a beach party. I already knew she was a guy but she was so beautiful. So at one point I asked her if she wanted to go for a walk and after a few minutes and let her know that I was down. Her response was ... Read full Story
PNPFUCKBOY 2019-02-12 12,191 Teen (18+) Small Tits Crossdresser Amateur Big Tits Outdoor Latina Bareback blonde Big Cock Ladyboy domination Guy Fucks Shemale Interracial Sex Toys Mature Homemade Ass to Mouth
96%
Family Frolic
FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... Read full Story
shemale lover 2012-01-14 31,323 strapon porn
75%
Sissify Your Boyfriend Manual - transation
original= manual-sissificar-a-tu-novio-4979 Used google translate, found some pronoun/object/context issues, and I believe ladybug = ladyboy Sissify Your Boyfriend Manual MANUAL FOR WIFE/GIRLFRIEND TO SISSIFY YOUR MAN, DISCOVER HIS SUBMISSIVE SIDE AND TURN HIM INTO ?HORNAND? AN... Read full Story
shelli_k18 2021-04-20 8,913 femdom sissyboy sissification sissy training FLR hotwife guidelines Modern Marriage Power exchange
50%
The Chronicles of Drodge Mallea
Drodge awoke feeling fuzzy headed and stiff. Actually, "awoke" wasn't quite right -- "came to was more like it. She sat up in the lavishly furnished boudoir, stretching her athletic 6-foot frame as she did. Running a hand though her short, thick copper locks, she slipped out of the... Read full Story
shemale lover 2011-10-24 3,200 Cumshot shemale Big Cock
50%
Transgender Art: A Sampler
It's not often that transgender art offers viewers a glimpse of a female-to-male transsexual. Usually, the transformation is in the other direction, with the loss of the vagina in favor of male genitals and the acquisition of female breasts. However, one image does reverse this trend, showing a fema... Read full Story
shemale lover 2011-09-06 3,756 shemale transsexual transgender
94%
Southern Hospitality Ch. 01
XtinaSmith2017 Ash gawped at his mother, incredulous as to what she had just said. He understood the basic premise of what had happened, but the reasoning she must have had absolutely baffled him. "Why?! Why would you do that?!" He pleaded, voice light and desperate. She shrugged, looking acr... Read full Story
Gwapo67 2022-05-16 7,424 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature
100%
Rachel and Chris
Part 1 : Rachel and the Ring Yesterday was clear with a light but chilling winter wind present to remind all that the bit of warmth in the sun would only last a couple of hours at best. I struggled between sweating and freezing as I worked to remove the winter street grime from my roadster. Top ... Read full Story
shemale lover 2012-04-10 4,774 Cumshot oral sex Sex Toys
80%
Too Much Hospitality
Ash looked himself over in his bedroom mirror critically, finding himself oddly self-conscious about his looks. He had been texting Laura all throughout the day and they had agreed that dressing pretty casual would draw the least suspicion, so he had. He wore a simple patterned t-shirt and some ... Read full Story
ASSEaster5678 2018-09-17 8,848 anal Blowjob transsexual oral sex cum swallowing romance transgendered Consensual Sex Older Female / Males
87%
Southern Hospitality Ch. 03
XtinaSmith2017 Ash looked himself over in his bedroom mirror critically, finding himself oddly self-conscious about his looks. He had been texting Laura all throughout the day and they had agreed that dressing pretty casual would draw the least suspicion, so he had. He wore a simple patterned ... Read full Story
Gwapo67 2022-05-16 4,999 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
65%
Marcia Goes Back to School
Marcia was painfully nervous. She hadn't been able to eat very much in days. The upside was she was even skinnier which would make Mistress and her husband very happy. She'd always been thin and on the diet Mistress Carol had her on she was already thinner than she dreamed possible. Her anxious stom... Read full Story
shemale lover 2012-12-19 10,824 Masturbation Blowjob blonde ass fucking big boobs
100%
Buying Heels
I have to know what it feels like to wear heels. I have the house to myself tonight and I'm going to play. I already have panties but want to buy some new ones. My wife bought me a black, frilly thong which I wore for her when we went out one night; I also have a cheap, supermarket pair of sheer ... Read full Story
shemale lover 2012-09-30 4,955 Stockings Cumshot oral sex crossdressing
50%
Sex with Shonda
I'm a workaholic by nature. I love my job but that's not why I work so much. I work long hours simply because when I get home I don't quite have anything productive to do. I just sit down in front of the television or I chat over the internet. Life at home is dull so the best solution seems to be en... Read full Story
shemale lover 2011-09-18 4,200 Blowjob fingering handjob
100%
Bagging a Bitch with Balls
Watching porn has given me a lot of ideas concerning what to do in bed--and elsewhere. Some of the guys and sluts in X-rated videos do it outdoors--in the woods, a park, poolside, or in a parked car. Some chicks flash their dicks--yeah, I watch shemale movies sometimes, too--in public places, and so... Read full Story
shemale lover 2011-09-27 5,625 transsexual ass fucking tit fucking
100%
ROBERTO’S SECRET by Spanky De Bautumn
Cody Daniels was only trying to help her country; she never dreamed things would come to this. She was patriotic and felt compelled to do whatever asked of her to aid in the capture of the terrorist known only as "Roberto". But lying in his bed, bound and gagged, Cody wondered why she let herself go... Read full Story
SpankydeBautumn 2021-01-22 5,118 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
50%
Clinton
"How many inches?" she asked. "Twelve," he said. "Really?" "Really." "If you're lying, you're just wasting your time." And mine, she thought. "I'm not." "Okay, then. It's a date." Tiffany hoped the jerk was te... Read full Story
shemale lover 2011-09-19 10,888 Big Cock cunt anus