Sort by
Relevancy

Free Stories

100%
A Slut is Born Chapter 2
The week went by slowly as I digested what Jim had done to me last Saturday. As I walked around school, I found myself looking at people differently, wondering if any of them had ever been treated the way I had. This would always bring the details of what Jim had done to my mind and my cock would im... Read full Story
shemale lover 2012-06-27 5,718 Group Sex Cumshot Blowjob
80%
Fifi's Long Wait
Around about 3 weeks ago, Sid had managed to acquire his very own maid; however, 'she' was not your normal run of the mill domestic worker. Oh no, Fifi liked to dress as a maid to fulfill her submissive cravings and the most notable difference was the fact that she had a penis. When working as a mai... Read full Story
shemale lover 2012-08-03 4,917 Cumshot oral sex Sex Toys
100%
One Special Night
Marilyn called me at the office with just three words. "It's on tonight." After a few moments of listening to the silence on the other end of the disconnected call, I realized what she was referring to. Immediately my cock began to swell, sliding slowly inside my satin panties unti... Read full Story
shemale lover 2012-09-02 4,534 Stockings Cumshot Masturbation Fetish Blowjob
100%
Simon
This is a true story that I need to share and has completely change my sex life. I've been married to my loving husband for 20yrs and have been totally faithful. we have a good sex life and are both in our mid forties, both in good shape we also have a fifteen year old daughter. I like dressing sex... Read full Story
shemale lover 2012-11-19 3,019 Cumshot orgasm oral sex
85%
Becoming a Shemale's Bitch
I just got into town and spent the whole day moving in and cleaning my new apartment. I didn't have much furniture but the place needed a lot of cleaning. I saw their was a bar a few blocks away from my apartment and decided to go out for something to eat. It was around five o'clock when I walk... Read full Story
metamafia 2012-12-21 119,410 hardcore Cumshot sucking bdsm domination
93%
I Am My Wife's Best Girlfriend
I was standing in our bedroom, my wife was on her way out the door. I was holding her slip up against my naked body. It felt very sensual. I pictured myself, for just a moment, as a real woman, with large breasts, big blonde hair, and smooth, hairless skin. I rubbed the fabric against me, sighing. S... Read full Story
shemale lover 2013-01-18 7,341 Crossdresser Cumshot Creampie Blowjob ass fucking
91%
My friends new roommate and her surprise
So my friend Rebecca and I were planning on going to this bar for the evening but she called me and said she was running a bit late and that I should wait at her place and that her new roommate Shawna should be there to open the door for me. Rather, than wait in my car I went upstairs to her apartme... Read full Story
shemale lover 2013-05-07 15,355 Cumshot suck cum oral Guy Fucks Shemale
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 4,588 Stockings anal sex suck threesome Interracial cum swallowing
92%
Crossdressers first time with a guy
Hi, im new to this. this happened about 3 years ago now. I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from th... Read full Story
shemale lover 2013-06-06 10,507 first time Teen (18+) hardcore anal sex fingering Interracial cd
100%
Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
shemale lover 2013-07-18 8,636 anal sex Ebony oral sex Interracial kissing
68%
I meet my new Mistress for the first time
I was feeling excited about and looking forward to Friday night. The reason for this was that I intended to dress up as my alter ego, Tania Harvey, and to go for a night out to a club nearby that is popular with TG’s, TV’s and other like minded people. I took a lot of care and attention over the way... Read full Story
Tania Harvey 2017-06-26 8,308 Amateur gangbang 3some shemale on shemale dominating
100%
Daddys Little Slut
I have been living with my dad for the last year after my mum who is Indian, found out that I was doing lots of drugs, and that I was bi and also a cross dresser. We never talked about it as for me, the cross dressing was on and off and usually when i was high. When i turned 25, I tried meth, and fo... Read full Story
aishacox 2023-01-31 5,580 Crossdresser Cumshot Fetish Blowjob Latex
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 7,258 anal Shemale Fucks Guy Big Cock Frottage
50%
Hard Decisions by Elaine © 2020
Hard Decisions by Elaine © 2020 No one in this story is based on anyone alive or dead. It is a work of fiction and should not be read by minors. I appreciate the kind efforts of many of my friends who cast a welcoming glance over the initial writings. I owe you all a big debt of thanks. Prolog... Read full Story
Elainetguk 2023-09-06 5,048 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
85%
My Cock Dream
My name is Iris Cal. A few weeks ago, I had a dream. This is an account of that dream, with some holes and details filled in by my own fantasies. From what I remembered as I tried to write down as much of the dream as I could, I had woken up in the house in which I lived when I went to high schoo... Read full Story
shemale lover 2016-04-14 5,087 shemales Masturbation Fetish
100%
I Knew Her Secret
I had a serious crush on the postal lady, I would wait on her until I saw that she was coming and then I would either make up some reason to go outside and exchange words with her or I would watch naked from inside of my house. I know it sounds perverted but I just couldn’t get enough of her. ... Read full Story
shemale lover 2011-09-20 6,651 Cumshot asshole fingering
55%
Teach me to love cock
I woke up from my soft bed and started watching tv then the door bell rang and it was the mail women she was black and she had big lips big huge tits a big nice round ass and a thin body she want to welcome me to the naberhood she also had sexy long green and red hairshe gave me her number and said ... Read full Story
shemale lover 2011-12-28 4,114 anal shemales hardcore
100%
Siisy Bride gets what she deserves
I had Ben on a contact site and we live surprisingly close together in Manchester. Ben is a 6’2” black man who has a large sex drive and likes women and girly trannys. I am a slim white guy who likes to dress like a smart woman, not a slut. I haven’t worn a wig for over 6 years ... Read full Story
shemale lover 2012-01-05 4,611 shemales interracial sex bdsm
100%
First Time With a Shemale
I was living in LA and pretty fresh out of school, not to mention pretty naive in the peripherals of human sexuality. I'd been with a few girls growing up, but nothing ridiculous. I liked going out with my buddies, and we'd drink and there was the occasional recreational use of ummm, how should we... Read full Story
shemale lover 2012-02-12 6,285 first time Cumshot sucking
100%
A New Experience
I had been sat in the hotel lobby for a couple of hours, bored, just watching people come and go. I hated these business trips. There I was in a strange city, knowing nobody, hanging around waiting for business meetings. Out of all the people I had seen there were such a variety of people. Pensioner... Read full Story
shemale lover 2012-04-01 2,691 Cumshot Creampie Big Cock
100%
I Knew Her Secret..
I had a serious crush on the postal lady, I would wait on her until I saw that she was coming and then I would either make up some reason to go outside and exchange words with her or I would watch naked from inside of my house. I know it sounds perverted but I just couldn’t get enough of her. ... Read full Story
shemale lover 2012-04-04 5,030 anal sex Cumshot fingering
100%
Sex in the Bar
Being a old Ex sailor it is no surprize to me that I am not shy. I live in Thailand and worked there a couple of time over the years. Down south near the Malay border there is a great little town where a lot of expats work and live. I am a sociable guy and love a few beers with the boys/girls/ an... Read full Story
shemale lover 2012-04-06 3,677 Cumshot Ladyboy oral sex cum swallowing
66%
A Night Out To Remember Part 2
Decisions... decisions... we all make decisions everyday and most of them are simple easy decisions. Some may take hours, some take seconds and some are made before we even know it. Some decisions carefully planned and some have planning at all. Some decisions are between several choices and some ar... Read full Story
shemale lover 2012-04-20 3,032 anal sex Cumshot Sex Toys
75%
Amy & Hope
My name is Amy but my real name Anthony and I turned 21 and started my first step on becoming a woman I decided to get some breasts for my birthday since I'm becoming a woman so after the surgery I felt more like a woman I was 5'9 weight120 and had long brown hair and some perfect size tits they was... Read full Story
shemale lover 2012-04-25 3,587 Big Tits cum transformation oral sex vaginal sex
50%
My Clipped Cock
Technically, right now I am an "It." A few weeks ago I was a "He." In another few weeks I will be a "She." The adventure is a celebration for me. I am doing everything right, and sensually documenting and sharing the adventure with my very-supportive and very-erotic fri... Read full Story
shemale lover 2012-04-27 4,770 transformation crossdressing
100%
Olderman and mature crossdresser Part 2
We left the park and drove to his house which was very nice.I knew he was wealth when he picked up due to his car was new jag. He fixed me drink and we sat on his couch and kissed and made out an heavy petting.He kissed my neck driveing me nuts as he did I rubbed his cock thru his pants which was ha... Read full Story
shemale lover 2012-05-26 4,126 Crossdresser anal sex Cumshot oral sex Mature cum swallowing
100%
A Reluctant Gang Bang
Hi all! I have been cross dressing and playing with men for many years now. One of My first experiences was being gang fucked by about 9 guys at an adult arcade. I was 18 at the time and it kind of traumatized me as it was pretty much a gang rape at an adult arcade. I was dressed up in a white flowe... Read full Story
shemale lover 2012-05-28 8,736 anal sex Creampie Fetish gangbang crossdressing
100%
Betrayed Chapter 4
I really wasn't surprised when Dianna directed me into the parking lot at Ringers. It was only a few blocks across town from my new home; a five-minute drive, if the traffic wasn't killing at the time. Consciously, it had not been a factor in my decision to take the new place. Sub-consciously... wel... Read full Story
shemale lover 2012-05-29 5,257 Cumshot orgasm condom sex
58%
My real story
I couldn't believe it. Here I was in bed with an older man – and one that I most wanted as he lay there sated by my ministrations to him. It had all started two weeks earlier when I had posted an ad on Craigslist. Up until this particular posting I had always been pretty bland..."Willi... Read full Story
shemale lover 2012-06-10 6,486 hardcore Cumshot bdsm oral sex
66%
A Ski Bunny is Born
AQToday I am a fully-fledged she-male, living with my girl friend Kim, who, to me, is the most beautiful girl in the world. We live as sisters to the outside world, but we are in fact passionate lovers. This whole true story started some 5 years ago, let us tell it to you. At that time I was a si... Read full Story
shemale lover 2012-06-21 11,594 anal sex Cumshot Lingerie oral sex Sex Toys
85%
A Summer Storm
The storm had caught us completely by surprise; we hadn't noticed the darkening clouds on the distant horizon as we lay in the late afternoon sun, talking about how our lives had changed since we last saw each other, nearly eight years ago. We had been best mates since primary school, doing everythi... Read full Story
shemale lover 2012-07-05 8,556 Cumshot Fetish oral sex cum swallowing
100%
Darling Nikki Part 2
Chapter 1 - The Morning After The next day, Nick awoke thinking it was just a really messed up dream. When he got out of bed and found that Samantha had unlocked and removed the dress, panties and shoes, but everything else was still on, he was pulled right back to reality. He looked in the mirro... Read full Story
shemale lover 2012-07-15 4,557 Cumshot oral sex sissy
0%
A Working Sissy Girl
I look up at my boots. Cute! Received delivery just day before yesterday, my boy friend hasn't even seen them yet. He'll like them, know he will. 3" spike heel ankle boots, very shiny patent leather, I look up at the one on my right foot. I run my hand down the thigh-high lace top seamed nylon ... Read full Story
shemale lover 2012-07-29 3,945 Cumshot oral sex sissy
100%
David to Dee
"Dave," she purred, "you know you can tell me anything. Surely you know you can trust me not to judge you by your fantasies." He was squirming under her touch, his eyes tightly shut, trying to avoid telling her his deepest secrets on the one hand, and on the other, hoping beyo... Read full Story
shemale lover 2012-07-29 12,791 Cumshot Masturbation oral sex
87%
Finishing School for Shemales
Mistress K looked at the school report and smiled. She wouldn't describe herself as an evil bitch, but plenty had. She was proud of her position. Headmistress of the Finishing School for TGirls. So many beautiful shemale girls had left her careful administration and gone on to happy lives, or ... Read full Story
shemale lover 2012-08-09 10,690 shemales Cumshot domination oral sex
100%
Brazilian Discovery Chapter 2
Chapter 02: First days in Brazil The tub was so large that it could have been a small swimming pool. Joan plunged into the water and started to lick Barbara's pussy underwater. When he rubbed the tip of his nose against Barbara's clit, she mightily climaxed several times in a row! Sometimes, inst... Read full Story
shemale lover 2012-08-25 3,823 Group Sex Cumshot oral sex rimjob
100%
Revenge is Sweet
Henry Stewart was thirty five years old, married to a very attractive woman who'd given him three kids, he owned and ran his own very successful computing company in San Diego, "Stewart Computing", meanwhile he owned a large house in the wealthy small town of River Falls. All in all, Henry... Read full Story
shemale lover 2012-09-01 7,917 Crossdresser Cumshot Masturbation Lingerie heels
100%
Transsexual Mistress
I had heard some intersting comments about this S and M club and so I decided to go by and check it out. I walked in about 9pm and things were just starting to get warmed up. I sat down with a beer and looked up at the main stage where a gorgeous raven haired dominatrix with an enormous set of ti... Read full Story
shemale lover 2012-09-08 4,765 Cumshot Blowjob domination ass fuck
100%
Wife Converts Husband Chapter 3
After about a month of being dressed up and acting as a female, trying out all the different outfits we had purchased and Shelley feeding her strap on cock to my willing mouth and ass every chance she got. My ass and mouth was now well and truly broken in. Shelley came home one arvo with a flyer ... Read full Story
shemale lover 2012-10-18 5,654 anal sex sucking cum swallowing
100%
Dottie's Back Chapter 5
I was woken from my afternoon slumber by a soft touch to my lips. Opening my eyes, I found I was still in the room where I had been toyed to orgasm twice while an audience of men watched from behind mirrors. The mirrors had returned to their reflective setting. Kim sat beside me, looking down smilin... Read full Story
shemale lover 2012-11-02 2,790 Cumshot oral sex jacking off
66%
An Ass to Die For
It's a very strange thing. We all have our personal quirks. The things that make us unique and stand out from the crowd. I've just never met anyone besides me who has mine before, and to tell you the truth I'm not sure if it's a gift or a curse. You see, I have a girl's ass and not just any old girl... Read full Story
shemale lover 2012-11-13 4,213 big dick sucking porn
100%
An Unexpected Birthday Gift
It was my best friends birthday and I was taking him out for a night on the town. We have been best friends since we were kids and I was going to give him a special present. We started the night out with dinner at a nice sit down restaurant where we had a few beers and some really good steaks. This ... Read full Story
shemale lover 2012-11-17 3,551 Cumshot oral sex cum swallowing
100%
When the Balls Drop; A New Years Tale Chapter 12
Chapter Twelve: The Show... "Mmm...God that was hot." Mason said. "I think someone needs to clean Candie up...it's your turn Mason..." Veronica instructed. Mason guided the dancer over to the bench and laid her down on in lengthwise. He rubbed his hands up the dancer's s... Read full Story
shemale lover 2012-12-06 2,121 anal Cumshot fuck
75%
Fucking Insatiable
* Draenei futanari, as many of us have become intimately aware, are fucking insatiable. For many of the same reasons, they also have a tendency towards entitlement and ego issues. This is hardly surprising, being a magically-fueled blue-skinned space-babe with positively porn-star T&A and a d... Read full Story
shemale lover 2012-12-07 5,880 sucking gangbang Futanari
100%
Watching too much porn
It’s another night at home alone. You get that aching again so you go to put on your favorite video. You just love big asses and big titties. The video starts and you see the gorgeous blond strutting in wearing her 5 inch heels, incredibly short skirt that is flashing her skinny red thong, ... Read full Story
shemale lover 2012-12-17 3,870 Masturbation interracial sex oral
60%
Tyra Takes Control
Tyra: "On your knees, whore," she ordered still fully clothed. Tyra: "A whore belongs on her knees, doesn't she?" Jim: "Yes, mistress." Whack, she smacked him across the face. Tyra: "That's master to you mother fucker. A mistress doesn't have a 10"... Read full Story
shemale lover 2013-01-11 5,449 hardcore sucking ass fucking ass licking Interracial
84%
Lesser of Two Evils
My name is Eric. At 21, I was working as the IT guy at a prominent Caribbean cruise company. My days were usually pretty boring. Fixing computer problems were usually a no brainer for me. People are so stupid when it comes to how they use their machines that I assume there will always be a need for ... Read full Story
shemale lover 2013-03-27 22,997 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
92%
Lucy's Change chapter 2
Chapter 2 Sunday was even darker and rainier than Saturday. We woke up still holding each other from the night before. We were spooning. Lucy’s warmth felt so nice against my back. Her legs only reached halfway down my calves, and I could feel her rubbing my legs with her toes. I could tell that sh... Read full Story
Alex1090 2015-03-31 6,510 anal big dick tranny shemale ass fucking
96%
A New TS Slut is born
There I was, one week before the end of high school. Going to college in the fall. Nice car, good f****y, friends. I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town, dressed as a cheerleader with a cock in each hand, one in my ass and one buried i... Read full Story
shemale lover 2014-01-29 9,288 Cumshot suck ass fucking oral sex Guy Fucks Shemale
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 6,770 tranny ass Teen (18+) Big Cock jerking
88%
Tgirl trained to be the town whore to serve ALL Black men
A few years back I spent time on and off with several shall we say more dominating types of gentlemen One of them, who for this I shall call Leroy, just loved when we got together to make me totally helpless. It was our 6th or 7th meeting. Leroy and i had been chatting on Yahoo and when he f... Read full Story
__tiffanylondontv__ 2014-09-30 6,233 suck shemale ass fucking Interracial big cocks
66%
My TS escort
I finally cracked and I had to know what it was like to be with a tgirl. After a quick google search I found a young and sexy tgirl in my area that was willing to play for pay. A short drive later I find myself parked outside her home, and I'm nervous as hell. I get out and walk over to her hou... Read full Story
DirtyMike69 2015-01-04 5,806 anal first time tranny Cumshot shemale oral
72%
The Weekend
The weekend A story inspired by the very sweet and sexy samantha satine and my beautiful wife Part 1 - The preparation samantha packed her suitcase with her usual attention to detail, makeup, lingerie, wigs, but no dresses. Her head was confused by this, Master D had given her instructions... Read full Story
MasterofSissies1 2018-12-04 8,989 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
91%
Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
ThatEroticWriter 2019-07-24 8,657 Big Tits Cumshot Masturbation Uniform Frottage
100%
TG Neighbor
With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... Read full Story
Jon Paul 2022-04-22 6,838 Big Tits Cumshot Latina Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale
100%
I Fooled Everyone But the Black Pimp Part 5
I had a few moments this night that will remain with me forever, and this was one of them. It was like I had an overhead view of myself. I could see my hands moving, one up and down Keiths cock, the other softly massaging his big balls. I see my hoop earrings, my red lips and my temporary tattoo. I ... Read full Story
cdtampa4u 2023-05-31 5,310 Crossdresser Interracial sissy bbc sissy