Sort by
Relevancy

Free Stories

100%
Digging for Home
Never Make the Last Out at Third After some minutes, Charlie broke the embrace. Backing away a step, she steered her moist brown eyes into Frank's damp grey ones. "What now?" The man tilted his head to one side and shrugged. "I'm not sure. It hasn't been a day yet since you went... Read full Story
shemale lover 2012-08-25 4,685 sucking cum facefucking
94%
Tortured by the T-Girl Tutor
Duncan didn't quite know how to handle it. He'd planned on a quiet Winter Break. Sleeping til noon, watching too much television and eating tons of junk food. That kind of stuff. He had a whole two weeks off from community college. At school, he was an outcast. They say life gets better after hi... Read full Story
shemale lover 2012-12-18 34,026 Big Tits shemale Big Cock Lingerie domination
100%
Double Anal With a shemale
....He answered the door and there she was beautiful as ever. He had just paid 500 dollars to have a transsexual e****t come directly to his door and greet him. She had on a long pea coat and thigh high boots. When she took the pea coat off all she had on was a one piece swimsuit. Her tits were a 36... Read full Story
shemale lover 2015-04-29 5,380 tranny suck Big Cock ass fucking dp precum
94%
Renting out a room
When my wife suggested that we rent out the guest rooms above the garage to a college student it sounded like a good idea. It was very much like a small apartment, with a bedroom, bathroom, and small living room. No kitchen of course, but we could share ours and it seemed like a good way to make a l... Read full Story
Alic91lovesporn 2015-07-29 21,349 suck shemale jerking orgasm domination
80%
Working Gurl
My name is Danielle and I’m a working gurl . I started working in 1991 at the age of 20, my first job as a hooker was working out of an Adult Book Store North of Ft. Worth, Texas on I-35W South of the airport My boss was an older tranny named Jannice she ran the book store. On nights when she would ... Read full Story
Danielle Dot 2015-11-27 5,394 anal licking sucking shemale swallowing
94%
Shemale Ride Along Part 1
I'm going go ahead and get this out of the way. During my freshman year of college, I was confused about my sexuality. It sounds strange saying this right after calling myself confused, but I loved girls. I really did. I loved all of their shapes and curves. I loved tits, pussy and ass. Now... Read full Story
qtball 2016-08-29 12,458 anal tranny Blowjob Big Cock bj asstomouth
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 8,675 anal Blowjob transsexual oral sex cum swallowing romance transgendered Consensual Sex Older Female / Males
100%
His Ultimate Fantasy
Jeff and I had been back together for a little over 5 years when I had decided to give him his ultimate fantasy. To everyone who meets him, Jeff is the all American boy. He is the quintessential small town boy. He always has impeccable manners, says his "ma'am's" and "thank you's"... Read full Story
shemale lover 2011-10-08 4,422 shemale orgasm pussy licking
87%
They Were Right
They were my friends, but I'd had sex with both of them. Not at the same time, but I had dated the one for a month and just started dating the other. So, although the thought had never crossed my mind before, I found myself dressed up as a girl for Halloween. After we had partied at a few clubs and ... Read full Story
shemale lover 2011-12-29 5,811 shemale Big Cock porn
100%
Barbie Jo Adventures Part 3
Saturday Afternoon The sound is ringing in my ears as I drag myself out of a deep sleep. I look over at my clock and realize it's not the right time for my alarm. As I come more to life, I pick up my phone. "Hey gorgeous, how you feeling?" Booms a voice through the receiver, making my h... Read full Story
shemale lover 2012-02-18 3,034 anal sex cum jerking off
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 4,890 anal sex Cumshot fingering
60%
Amy's Surprise 2: Enter Karissa
What did you think? Amy asked. Well, let's see, I started to answer, You gave me the best blowjob I've ever gotten, sucking your dick was about the best thing ever, and sharing your cum with you was incredible.all in all, I'd say it went well. Amy smiled and walked over to sit with me on the couc... Read full Story
shemale lover 2012-05-08 4,544 anal sex shemale Sex Toys
90%
Gali's Surprise Package
Chapter One Gali sat in the front row of John's class with her legs crossed, raising her skirt and revealing her garter. She had sat there since the start of a new school year, and it was her seat for the rest of the year. She'd taken Beginning English Literature from him last year, and she was a... Read full Story
shemale lover 2012-06-02 6,824 anal Big Tits Cumshot facefucking
100%
A Revenge Fuck Part 2
Frankie had been a great sport about the entire affair. She had taken me in, she'd showed me how to become and be the beautiful woman, Josie- she had completely made me who I was, even against her will. And then she was also there to shoulder support in my emotional crisis when things did not work o... Read full Story
shemale lover 2012-06-03 4,857 anal sex Creampie shemale oral sex
100%
Cathy's Friend, Transsexual Mary
I have told you about my daughter Cathy. She is a stripper at a nude club. She has sucked me and I have got to fuck her in her ass. All this in front of her friend Bill and Mary. Bill is Bi, like me and Mary is a transsexual. I'm also a cross dresser. Just two weeks ago I found out that my daught... Read full Story
shemale lover 2012-06-05 3,939 anal sex shemale facefucking jacking off
85%
A very hot encounter
I've had been feeling way too horny for days; masturbating every night to shemale porn. I've always loved transexuals. There's nothing better than a very hot body with a fairly large cock to be sucked and drained of hot cum. There's something even kinkier for me about a top shemale. I imagine that c... Read full Story
shemale lover 2012-07-08 4,643 anal Cumshot oral Sex Toys spanking
100%
Defend Each Other
San Francisco International Airport, San Francisco Ca. Main Terminal area 12:35 a.m. 16 September. Alex sat in the quiet airport terminal, fixing her lipstick in a small compact and checking her make-up, waiting for John to arrive from Japan. John had gone to Japan to convince his investor in ... Read full Story
shemale lover 2012-08-10 3,590 anal Cumshot shemale oral
100%
Your Best Damn Girlfriend Ever
There are times in a young man's life when it is so full of fun and sex that it's a wonder they survive. College is one of those times for many young men and it certainly was for me. I attended a small private collage in southwestern Ohio at a time when the world seemed to be totally focused on it's... Read full Story
shemale lover 2012-08-11 12,560 anal sex Cumshot shemale oral sex
100%
Young Sissy Chapter 1
I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a man, just to s... Read full Story
shemale lover 2013-01-04 10,176 sucking Fetish Uniform domination big boobs
50%
La pistola NEGRA del Tío, entre Las Bragas de Mi Tía LA PUTONA
Aaayyy.. Yo sabía que la Tía había sido Flor de PUTONA.. pero, jamás me imaginé que me iba a tocar a mí 'hacerme cargo de sus cosas'.. su 'herencia'.. la casa ya vieja, por reordenar destinar y.. LAS COSAS que una descubre ya con los años! Todo estaba igual, pero HORRIBLEMENTE ARRUINADO.. más, e... Read full Story
Ari Riè 2021-06-03 2,120 Teen (18+) Small Tits Crossdresser Latina Bareback Shemale Fucks Guy Fetish blonde Big Cock Uniform Lingerie domination Premium HD
100%
BBC DOMINATION SISSY BLANC
Mon nom est Tim. Je suis un homme blanc de 23 ans. Il y a environ 6 mois, j'ai déménagé à Los Angeles pour essayer de devenir acteur, mais comme vous vous en doutez, je n'ai pas eu beaucoup de chance dans ce département. C'était début novembre, quand je suis allé dans le bureau de mon... Read full Story
Femboy 2021 2023-02-04 1,160 Stockings Big Cock Lingerie domination Guy Fucks Shemale Interracial Sex Toys
50%
MARIAGE CLASSÉ ADULTE ⚧️ ⚧️
1. 'Alan à Alisha...' La salle de bain était embuée et le miroir s'embuait alors que je me dirigeais vers la baignoire. Là, dans toute sa gloire, était assise ma magnifique épouse Liz qui occupait déjà un coin de la baignoire, seul le haut de son torse était visible avec toute la mousse qui l'ent... Read full Story
Femboy 2021 2023-02-21 789 Crossdresser Cumshot Fetish Blowjob Big Cock gangbang Lingerie Guy Fucks Shemale Interracial
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 30,955 strapon porn
50%
How to Convince Your Wife to Try Black Cock
I didn't write this - but it's great info for all my sissy cuckold sisters out there desperate for their wives or girlfriends to go Black. I hope all your cuckold dreams come true! There are so many stories out there from white guys who admit that they want to see their wives and girlfriends,... Read full Story
Sissy Annabelle 2023-10-07 5,872 Interracial cuckold
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 8,417 femdom sissyboy sissification sissy training FLR hotwife guidelines Modern Marriage Power exchange
33%
A Certain Perception
Kyra was not the girl of my dreams. I never DARED dream a woman that good would just walk into my life. She was smart, sassy, vivacious, intuitive, resourceful, and a real 'people person'. We met in an Internet chat room called "Working Girls". We're not talking about the kind you find in ... Read full Story
shemale lover 2012-02-23 8,233 Fetish transformation dildo
90%
Why does cock look so good on a girl ?
Horny and looking for something to jerk off on, of started surfing porn sites looking for just the right hottie. Pornstar Christie Lee really gets my juices going so I clicked on her. I started watching the video I was familiar with and knew would get me off when I decided to check out all her video... Read full Story
Verdura08 2022-10-17 6,146 Crossdresser Amateur Cumshot Big Cock ts posing huge dildo
50%
His sexy flies catches my eye
Another routine day was passing as I carried my shopping bags back home. Turning up a side street the late afternoon sun shining I suddenly encountered the most sexy guy I had ever seen. He was so cool that I hadn't even seen guys on TV as cool and good looking as that. He was an Asian guy in his... Read full Story
shemale lover 2011-09-16 2,970 anal shemales interracial sex
40%
Kiara's Xtra large treat
I have developed an interest in t girls with the XXL tag, black and Latino girls especially seem gifted in that department, so when I seen this horney bunny on an escort page I knew I'd have to check her stats. A dark Latino Kiara boasted an impressive ten inches, I pondered on my way to meet her... Read full Story
Kinky Dee 2019-05-27 3,571 Small Tits Big Cock Lingerie domination Guy Fucks Shemale Interracial
90%
Sissy Slut and Stepdads
Frank was pumping me hard and his huge cock seemed to have grown and become extra hard. I am so thrilled that way he enjoys fucking my ass with such passion. I would almost think he was in love with me if this relationship wasn't so bizarrey. It’s ironic that as a male I always get total humiliation... Read full Story
Regina10 2020-11-30 9,238 Crossdresser Bareback Creampie Fetish Blowjob blonde Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth double anal
100%
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 5,977 anal Small Tits Crossdresser Amateur Bareback Blowjob Guy Fucks Shemale Interracial small cock big ass femboy
57%
Transsexual Actresses Part 1
The adult entertainment market includes thousands of videos and DVD's featuring transsexual actresses. Some of the more popular of these celebrities have their own web pages. Brief profiles of some of these actresses, including a list of their films, appears after the initial list. Adriana Ventur... Read full Story
shemale lover 2011-09-08 9,255 shemale transsexual porn star
100%
Lady and the Cop continued
The next night Regina got a visit from. Larry the cop who openly declared war on shemales and trannies. He was working a homicide where a trannie friend had been killed in her apartment. Larry was a known shemale hater and he never failed to express his opinions. Tonight he was in her apartment to ... Read full Story
Regina10 2018-03-06 4,671 Small Tits Big Cock Ebony Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
100%
Zoe procures a sissy..Chapter 1.
Zoe Viper sat back on her sofa extremely pleased with how her Friday night was shaping up. Wearing lace top stockings,a tight,black,latex miniskirt with a red satin corset and elbow length,black latex gloves,she took a drag on her blunt. Blowing out the smoke through perfectly painted red lips,she... Read full Story
satinpantyts 2024-06-28 1,134 Lingerie domination sissy
83%
Black Love: Transsexual Edition
My name is Steve Vincent. A big and tall young Black man living in the city of Brockton, Massachusetts. Currently, I'm a graduate student at the University of Massachusetts in downtown Boston. When I'm not in class, I work for the Department of Corrections. I'm openly bisexual, and love to have fun.... Read full Story
shemale lover 2012-06-27 4,074 anal sex Creampie Big Cock oral sex Interracial
93%
Miss Bernie
My name is Bernice McDonald and I am the very happy owner/ operator of a couple of children's day-care centers. I love my life and I love this work. I love children and since I have one of my own this helps satisfy my need to nurture. I have not always felt or recognized this need. I was born in... Read full Story
shemale lover 2013-02-22 14,086 hardcore sucking ass fucking Guy Fucks Shemale
85%
My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
the greatest liar 2019-06-14 11,857 Small Tits anal sex Latina Masturbation Bareback Creampie Blowjob Big Cock transformation gangbang Shemale and Girl Guy Fucks Shemale Sex Toys Ass to Mouth cosplay hormones high school real life situations
100%
Sultry Mistress,
Sultry Mistress, Natacha has now been living with me for over a year. It is a cerebral and perverse Domina who immediately wanted to submit me to her desires. She took power over me by making me discover my femininity during role-playing games. Like a spider, she imprisons me in her web a ... Read full Story
sandratvtg 2022-09-20 4,054 Stockings Amateur Lingerie domination Sex Toys
100%
Hits, Misses: G
Ok, what follows are some accounts of hookups and almost hookups I've had with transwomen in the late 2000s, early 2010s. Some I think about a lot. Others I've forgotten completely and am attempting to interrogate my memories. Things have changed a lot in the culture, mostly for the better. Visibili... Read full Story
bybaking 2024-02-06 4,818 anal Amateur Cumshot Bareback Big Cock Ebony Guy Fucks Shemale Interracial black Tgirl
100%
The formidable weapon of women
five ears of marriage, my desire for my wife having greatly diminished, she decided to take control of my sexuality. A female association transformed her in a few months into a perfect dominatrix both physically and cerebrally. Every night before bed, she approaches me, dressed in a latex comb... Read full Story
sandratvtg 2024-06-19 1,274 anal Lingerie femdom submissive femboy huge toys
100%
Christy's Fantasy Come True Chapter 6
The alarm went off and Christy rolled over and hit the off button. The clock face was starting back at her flashing 8:00. Since it was Friday she had slept in a bit. Jim had gotten up early and left for work after spending the night. They had gotten into a minor argument last night but came to a... Read full Story
shemale lover 2013-01-30 5,113 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
Fantasy 2
THE GANG BANG 02: I walk into an adult theater dressed in a black short dress with black high heels. Under my dress, I have on a black bra, black crotch less panties, a black baby doll, and a black Lace Garter with Stocking. I pay my fee into the theater and walk through the door to the seating ar... Read full Story
carriebangs 2024-07-23 373 anal Crossdresser Bareback Creampie gangbang Lingerie Interracial sissy double anal
50%
The Greatest Lie Part 6
In my rare moments of leisure in the weeks following my close encounter with death, I had had little opportunity to talk about it. Of course, the police had asked perfunctory questions, and I had testified at the coroner’s inquest, but until my next appointment with Dr. Erika Wright, I had not... Read full Story
shemale lover 2012-01-19 4,558 hardcore erotic encounters fantastic
100%
Becoming Paula
I work in an office with 15 coworkers about 11 of them are women. I get along well with my coworkers and go out of my way to be helpful. I find it is more fun to work with friends than to work with strangers. My name is Paul and I work in an insurance claims office processing claims and making recom... Read full Story
shemale lover 2012-04-05 6,475 anal sex orgasm fingering
44%
Fifteen Minutes or Less
Late night, middle of nowhere on a deserted back road. Todd is late on delivery with a pizza and getting really tired. It has been storming pretty bad for more than an hour. After driving a little longer, he finally sees a place and sure enough it looks like it. It's a pretty big place with three st... Read full Story
shemale lover 2012-04-21 2,521 hardcore anal sex Cumshot oral sex
100%
Steve to Stephanie Chapter 1
This is my first attempt at a longer story with deeper characters and a more evolved story line. Stay tuned for the next chapter. As always comments are welcome. * Steve was mild mannered guy with a big secret. Steve was an avid cross dresser, very bi actually leaning towards being gay. Steve... Read full Story
shemale lover 2013-01-29 3,844 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
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 8,430 anal sex Ebony oral sex Interracial kissing
87%
Alex
I'm a straight guy! a few years ago, I stubble the cross shemale p***. now I must say, it felt weird, I mean being used to watching females doing p*** on my life. but I have to admit, these shemales that I was watching were passable, and most of all looked very f*******. shemale p*** made my di... Read full Story
Mike212 2018-05-28 6,654 Teen (18+) Small Tits Amateur Blowjob Ladyboy Guy Fucks Shemale
80%
The Farm
“See you Sunday, baby,” said Marcus Jenkins to his wife, Tasha. “Alright! Have a good day at work,” the wireless phone company retail store manager smiled. “Love you, Kobe! Love you, Tiara,” the wastewater plant operator said to his offspring. “Love you, too, daddy,” the youngsters rang out in un... Read full Story
Faggyboi and Puzziboi 2021-12-08 5,516 Teen (18+) gangbang Guy Fucks Shemale sissy femboy Ass to Mouth
80%
Caught Watching Free Mobile Shemales
I was watching Free Mobile Shemales on my phone browser during my lunch break when the phone rang. Annoyed by the fact that someone is interrupting my free time, I answered angrily "Yes, who is it?". "Wrong number", said a female voice, "Sorry to interrupt you lunch!", ... Read full Story
shemale lover 2016-05-20 9,363 anal sex Cumshot asshole
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 5,442 transsexual ass fucking tit fucking
100%
Young Hercules: Versatile Stud by The Fan
Prometheus Academy. It sat atop a hill, dominating the vast region of Thessaly, Greece. It was the most prestigious school in the area. The most famous men and women of the world came there to get their education. The sons and daughters of kings and queens, ... Read full Story
shemale lover 2011-12-01 3,354 anal Creampie jacking off
83%
Tilted Kilt Chapter 4
Like most mornings after a late shift at the Tilted Kilt, I awake around 11 am and lay in bed as the day comes into focus. The sheets felt cool on my nude body and I realized my roommate, Shari, had left the air conditioner on before she left for work. It's Summer in San Diego and the days of late h... Read full Story
shemale lover 2012-01-25 3,629 Cumshot sucking transsexual fucking
50%
The Ultimate Cock Ball Torture
I miss my cock. Sometimes. I had one once - one of my very own, connected right to me - but now it's gone. Never thought I would miss it. I'm sure you've guessed by now that I am a full transexual. I had the boob job and started hormone treatment years ago and felt much better as a shemale th... Read full Story
shemale lover 2012-04-29 3,586 anal sex oral sex
90%
Wedding Night
It is the night of our wedding. Mayaand I had never had sex until this day. Many times I've tried to go for it, butshe always said I need to wait. And when I kept attempting to persuade her, shewould say I didn't love her. Maya is a very sexy Brazilian female that I metduring my vacation in Miami. S... Read full Story
shemale lover 2012-05-12 4,192 anal sex Blowjob shemale 69 position
100%
Francis Meets a Black Stud Part 3
As I washed myself in the women's bathhouse, I began to regret everything I had done. I had already cum and the sexual intoxication seemed to be gone. I could not believe that I had willingly submitted to what I had allowed that black man had done to me. I began to be very disgusted with myself. Fur... Read full Story
shemale lover 2012-11-20 3,692 sucking handjob black cock