Sort by
Relevancy

Free Stories

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 8,474 Big Tits Cumshot Masturbation Uniform Frottage
100%
I fucked the hotel handy man and he had a monster cock
I was on vacation in a new town and decided to stay at this new hotel. I heard it was the best and the location was close to some sites I wanted to explore. I enjoyed my stay there, especially one evening when my air conditioner stopped working, and the hotel guy came to fix it. He looked so hot tha... Read full Story
Madison Heights 2023-09-05 6,762 anal ass Big Tits Cumshot Bareback Creampie Fetish Uniform piss Ass to Mouth cum in mouth monster cock watersports
100%
Bareback fuck by Lysa Shemale
Well I am devoted shemale lover and have met many shemales in my life. This incident is of probably December. I called my shemale escort Amy to meet and some how she was not picking call. Then around 4.30 pm she picked n told me that she is having hangover due to party so was sleeping, so I sh... Read full Story
Stud4Shemale 2021-02-20 7,230 Cumshot Bareback Creampie Shemale Fucks Guy Blowjob cum in mouth barebackedshemales shemale fucks male cum in ass Indian Shemale Pune
81%
My first time getting a big cock in my ass
I got talking with a relatively local guy, much older than us, but had a thick 8.5" uncut cock, which was perfect for what I wanted to watch enter my Mrs. Our messages went something like this... Me "Did you want to meet up first?" Him "If you want" Me "We'll chat about a plan, then I'll... Read full Story
BalkanLoco91Ri 2019-08-26 7,619 Amateur Cumshot Bareback Creampie Blowjob Big Cock Homemade pov Ass to Mouth
100%
Big cock heaven.
I live in Vancouver and saw a beautiful trans escort online and couldn’t resist setting up a meeting. I met her at a hotel and she was just as beautiful in person as online. She was Asian and had the most wonderful big tits and ass. Her cock was a solid 8 inches, uncut with a big mushroom head, whic... Read full Story
Eyecandy64 2024-02-06 6,291 anal Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Asian
100%
Philippines Vacation with a Dominant Big Cock Ladyboy
I am still in a state of unbelievable joy that I was lucky enough to experience this but I 100% did and I can’t stop thinking about it as I thought things like this only happen in porn or fantasies. Buckle up because this is a wild one and happened in Manila May 2024. I had the opportunity to vi... Read full Story
AllenB 2024-07-14 2,601 Bareback Creampie Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale cum in mouth domination act filipina ts filipina ladyboy
100%
The Big Mature Shemale Next Door
The Big Mature Shemale Next Door SugarandSalt "Please can I just wear my old swimming trunks?" Warren begged. "No!" his mom yelled back from the other room. "Barbara purchased that for you. It was expensive so you better remember to thank her." Warren looked at himself in the full length mir... Read full Story
Gwapo67 2022-05-03 7,954 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
First time with big surprise
My first story translated into English, I hope you like it. It was late at night, I had been drinking with friends and was on my way home. I am a man in his early 30s, smartly dressed and looking quite attractive. The night was beautiful, clear sky, warm and in the city were some people on the ... Read full Story
Marten1201 2023-01-06 6,794 Big Tits Bareback Creampie Shemale Fucks Guy blonde Big Cock
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 11,864 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
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 9,903 Teen (18+) Crossdresser Amateur Masturbation Bareback Creampie Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth cum in mouth
92%
MY Party Favor Fantasy
My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... Read full Story
pennypenny 2019-01-08 7,279 Stockings Crossdresser Group Sex Cumshot Masturbation Bareback Creampie Fetish threesome Blowjob Big Cock gangbang Lingerie redhead domination Guy Fucks Shemale Sex Toys Ass to Mouth cum in mouth double anal
100%
Taking Ricky's Cherry
My work has me traveling all over the US and if you have read any of my previous stuff then you might have figured out that I have a major cougar streak. I just love being the first T gurl to a sexually inexperienced young guy. I was bored and horny in the hotel room, so I logged into a gay dating s... Read full Story
pennypenny 2019-06-11 8,418 Stockings Teen (18+) Crossdresser Cumshot Bareback Creampie Fetish Blowjob redhead Guy Fucks Shemale Mature Ass to Mouth cum in mouth
100%
Masturbation fantasies 2: Looking for Amanda
Previously: William, a young lawyer who has no luck with women, decide he needs some relief from a live girl. Scared of going with a prostitute, he decides to try out a peep show first. Without knowing that the stripper he chose is kind of special, he ends up in a show with a shemale called Amanda w... Read full Story
ThatEroticWriter 2019-07-24 8,895 Big Tits Cumshot Masturbation threesome Frottage
76%
The Guy At The Pool
The Guy At The Pool Stepping out of my hotel room for a smoke I saw two young guys at the swimming pool which my room overlooked. One of them was standing outside the pool speaking to the other guy who was in the pool. The guy beside the pool immediately caught my attention, his shirtless bo... Read full Story
pennypenny 2019-10-21 6,729 Crossdresser Bareback Creampie Blowjob redhead Guy Fucks Shemale Ass to Mouth cum in mouth
84%
My weekend with Nicole
So I believe I last left off about how me and Nicole started dating and let me say it was some of the best sex I've ever had but there is one particular time I could share. So after about 2 months of dating I was basically staying almost exclusively at her place. So the first weekend I s... Read full Story
Duke04 2017-05-20 10,710 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock redhead Ass to Mouth cum in mouth
100%
Getting Fucked By Jeff
Getting Fucked By Jeff I was sitting at the bar one night having a drink and wanting some dick when a man sat next to me and said “Hi, I am Jeff.” Smiling at him, I said” Hi, I am Penny.” Jeff and I chatted and he bought me another drink. After a while, Jeff said” In all honesty, I only boug... Read full Story
pennypenny 2019-02-25 6,365 Crossdresser Amateur Cumshot Bareback Creampie Fetish Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth cum in mouth
88%
Tommy Tries to Make It Up
Tommy Tries to Make It Up I have written about Tommy before. He was the eighteen year old neighbor that always stared at me checking me out, basically eye fucking me and that made me so hot and horny I eventually took his virginity and trained up on being a great lover. Well he had moved out... Read full Story
pennypenny 2019-04-30 6,209 Crossdresser Group Sex Bareback Creampie threesome Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth
100%
Steve
So on AFF, I used to be gold but guys will just hit you up, sooo I got hit up by an 8in boy. Wasn't sure I'd want to prep up an 8 so I didn't get all ripped up, but nice profile and a fucks a fuck sometimes. What to wear to get cum in tonight? Still pretty warm, I'll go mini with tighter leotard (mo... Read full Story
smtmsbrianne 2020-09-16 3,537 Crossdresser Amateur Group Sex Cumshot Outdoor Bareback Creampie Big Cock gangbang redhead Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Regina’s Double threat.
Hello guys, I recently ran into a former hater who was no longer the hater I had met years earlier. In fact, he had only treated me so horribly because of his own inner dark desires. When we met a few years ago at one of the clubs, he had been very abusive to me. He went out of his way to say hurtfu... Read full Story
Regina10 2022-02-08 3,069 Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock redhead Guy Fucks Shemale Ass to Mouth double anal
100%
Blind Date
XtinaSmith2017 Anthony awoke to a piercing buzzing tune, a nice enough melody, but one he had come to despise shortly after he had made the mistake of making it his alarm. The culprit, his smart phone, was plugged in on the nightstand beside him and was in the process of making him gleefully aw... Read full Story
Gwapo67 2022-07-01 5,599 Bareback Creampie Shemale Fucks Guy Blowjob
100%
Liberty in Lisbon Part 2
So here I was walking down the Av da Liberdade feeling very pleased with myself. I had just thoroughly enjoyed an experience I thought would only ever be in my dreams and, the best part, there was more to come [cum]. In fact I found myself humming the 59th Street Bridge Song. Life I love you feeling... Read full Story
Rusty12 2019-07-31 4,934 Amateur Masturbation Bareback Creampie Shemale Fucks Guy cumming
80%
Getting Fucked by Sasquatch
Bill was about to show up, I had known him from a chat room for years now. I was in his town for work and we had set up this date so we could finally meet each other. I heard a hard knock at the door and when I swung it open, I just stood there in awe. It wasn’t the big beard or really long hair tha... Read full Story
pennypenny 2020-08-21 5,985 Crossdresser Bareback Creampie Fetish Blowjob Big Cock redhead domination Guy Fucks Shemale pov Ass to Mouth cum in mouth
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 5,166 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
100%
Castro - shemale goddes
Nobody would have believed the scene was true, her slender, smooth and tanned legs crossed in such a deliberately provocative way as to reveal a glimpse of crisp white panties. Her tightly fitting, classically styled little black dress cut to ensure firm large breasts were displayed to maximum effec... Read full Story
Law12 2018-03-04 5,065 Masturbation Bareback Creampie Ass to Mouth cum in mouth Supernatural
66%
a day in the life of Amber SissyZofen 264
And the days had passed one after the other and now it was the day of my date. He sent me a txt at 8.30 on Saturday morning to say he was coming And you remember he was leaving his phone at home in case his wife called You know I had sent him my address, parking advice and left the gate ajar. ... Read full Story
amberdoll 2020-09-15 2,695 Stockings Small Tits Crossdresser Amateur Masturbation Bareback Creampie blonde Lingerie Homemade cum in mouth
100%
The Experience of a Lifetime
My divorce was hitting me really hard. My wife outgrew our relationship and started living her own life and I had a front row seat to everything. My heart and life was upside down. I didn’t go out anymore. Friends and family both told me it was time to get my life back on track and start living ... Read full Story
therefill05 2020-11-30 20,101 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy threesome Blowjob blonde Big Cock Ebony Uniform domination cum in 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 2,517 Crossdresser Amateur Cumshot Masturbation Bareback Creampie Ladyboy Lingerie Ass to Mouth cum in mouth
100%
Horny Writing A Strange Habit
I enjoy watching videos which I can Vicariously live. This is nothing more than my horny hobby, an amalgamation of various thoughts. My form of hands free edging. Spell checked only, "No I haven't proof read a first draft, not trying to publish masterful works here." Hope to hear from those w... Read full Story
Araina 2021-03-08 2,740 Crossdresser Amateur Big Tits Cumshot Bareback Fetish Blowjob Big Cock Guy Fucks Shemale Frottage Homemade Ass to Mouth cum in mouth
100%
TG Girlfriend moves in
Monday morning 6:00 am and I am just awakening, and I realize a naked body beside me has her arm around me, we are both naked. My wife Lydia is out of town to a seminar, and this adorable brunette perky tits and lovely eyebrows, beautiful lips slightly pink, sleeping beside me. Joanne and I had spen... Read full Story
Jon Paul 2022-01-18 5,168 Amateur Cumshot Latina Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale cum in mouth
100%
The Next Level
Nitromethane It's been a couple of weeks now since I sucked my last shemale cock and swallowed her load, and with enough distractions, it hasn't been too difficult keeping myself preoccupied and my mind off of satiating my new fixation. Still though, I do have my moments when I sit back and imagi... Read full Story
Gwapo67 2022-02-01 5,774 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock gangbang domination cum in mouth
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 4,786 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
96%
A Night of Lust
I was out at a night club with a few friends, and we were there for for a while before I noticed this sexy, rather short girl across from me at the bar looking over. I could tell, even from this distance that there was something special about her, I wasn’t sure what that was quite yet though. The mo... Read full Story
JessicaEdwards 2018-08-07 18,264 Stockings Amateur Cumshot Masturbation Bareback Creampie Shemale Fucks Guy Blowjob blonde Big Cock Lingerie deepthroating Guy Fucks Shemale cum swallowing deep throat deep penetration cum swapping pov Ass to Mouth cum in mouth anal fuck sloppy virgin ass
80%
Transsexual Savage
John had walked for eleven days. He was headed towards Fort Winston at the Hiat River, and he still had about three days ahead of him. The Hiat River was the natural border that separated the civilized world, where he came from, and the savage and brutal wilderness, where the natives lived and pract... Read full Story
Anal Orgasm 2020-07-10 6,286 Big Tits Outdoor Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Guy Fucks Shemale
100%
TO BE OR NOT TO BE – PART 6
TO BE OR NOT TO BE – PART 6 by Spanky de Bautumn Part 5. Sunny and Antonio got frisky at the bar, Sunny moved in with Mel and Shari, and opening night was a success The only other dress that I brought was one that I hoped I would get a chance to wear but didn't think I would. It was a black ... Read full Story
SpankydeBautumn 2021-02-26 2,447 Crossdresser Cumshot Masturbation Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
Sweet Encore
I was alone tonight and feeling just a bit paranoid as I listened to the soft music. The soothing sounds put me in a seductive mood, but It seemed that all my lovers were too busy for me, or they had other plans. Uncle Barney and my detective were probably home being dutiful husbands. Bo was under h... Read full Story
Regina10 2024-05-09 3,032 Crossdresser Big Tits Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale big ass Ass to Mouth
100%
She Lied ......... Part 2
Looking back on that dat & being honest wit myself, I probably made sure I didn't swallow every drop. I think I wanted to finally lose my virginity. I wanted to be the bitch. I wanted to feel like the woman. I wanted to REALLY feel her she-cock expand deep inside me and feel the warmth of her nectar... Read full Story
Curious_billy 2024-07-06 1,352 Amateur Bareback Creampie Shemale Fucks Guy Big Cock cum in mouth seduction Sweet talk Virgin asspussy