Sort by
Relevancy

Free Stories

100%
2nd date with Latina Sissy Destiny
So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... Read full Story
AllenB 2022-04-05 4,555 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
50%
FONDANT À LA VANILLE ⚧️ ⚧️
Je vois ma cible assise au bar, en quelque sorte à la limite d'un des groupes de commerciaux. Il prend une bière mais il ne boit pas aussi vite que les autres et il regarde nerveusement autour de lui de temps en temps. J'ai une préférence pour l'homme plus légèrement construit. Il doit être plus ... Read full Story
Femboy 2021 2023-02-21 1,129 Stockings Crossdresser Shemale Fucks Guy Fetish Blowjob Big Cock Lingerie domination cum in mouth
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 5,046 Small Tits Big Cock Ebony Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
100%
Late Night Snack (Touch me in the morning)
I was awakened abruptly by someone banging on my door at 1am. At first, I thought it might be Harry, the man who replaced Mr. Cobb in my bed a few nights ago. He had been persistent and horny constantly. I think it was because fucking trans women like me was new to him and he hadn’t got enough of th... Read full Story
Regina10 2024-03-28 4,472 anal Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Ebony Ladyboy Lingerie
91%
Thai Ladyboy
One year ago, when I was 19 I went back to Thailand. The year before was to see the sights and explore the country, the second was more exploring and more fun, the third and final time was to get with as many ladyboys as possible. I had always been curious about trans women. Im not attracted to ... Read full Story
BEN437 2018-11-19 13,986 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
100%
Thai Ladyboy
One year ago, when I was 19 I went back to Thailand. The year before was to see the sights and explore the country, the second was more exploring and more fun, the third and final time was to get with as many ladyboys as possible. I had always been curious about trans women. Im not attracted to ... Read full Story
BEN437 2018-11-19 5,623 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
100%
Santa & Mrs. Claus
In my story called "Santa Likes Fembois" here I explained that I discovered that last Christmas when Santa Claus visited my house then made me suck on his cock before fucking my boypussy. He also gave me an actual present: a winning lottery ticket. Well, with that multi-million dollar winning ticket... Read full Story
Chrissy Tunnell 2022-12-01 4,103 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
86%
How I became a ladyboy convert
Our friend Brian went to Thailand 3 years ago and had his first experience with a ladyboy details of which he would like to bring to Your attention now. He proudly tells he became a ladyboy convert after his first time and we have no doubt he did! On a trip to Thailand about 3 years ago I had my ... Read full Story
shemale lover 2015-02-07 9,270 Cumshot Asian Guy Fucks Shemale
56%
Big cock shemale from Pune, India
I just saw her profile on Planet Romeo, her name is ID is Kaynat / Muskan. I saw her photos and got attracted to her. I am always a big fan and lover of Shemales or TS. I called her and fixed appointment by negotiating with her for 2500 INR. I went to meet her, she stays in a condominium in ... Read full Story
Stud4Shemale 2017-05-22 97,150 Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
100%
New Orleans TS dream come true..
In was on New Orleans running water for the victims of Katrina in 2005. I went down to Bourbon St several times an one night I walked into adult fetish store and as I was looking around there was what appeared to be a very beautiful black woman bending over with a very short skirt on. I was admirin... Read full Story
jim3801 2018-09-11 11,214 Group Sex Bareback Shemale Fucks Guy threesome Big Cock Ebony Guy Fucks Shemale Interracial 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 4,029 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
41%
My first date with a "shemale"
I met a guy whom i worked with and found out he was bisexual,it didn't bother me nor did i care because i know who i was.I realized he was trying to date me without asking me if i was that way.I flat out turned him down and told him i didn't go that way! I was still young and new to this. I was coo... Read full Story
bmogotti 2020-03-09 13,808 anal first time Small Tits Crossdresser Amateur Blowjob shemale Big Cock Ebony fuck Lingerie Guy Fucks Shemale Homemade motel
77%
Slut indiscretion
At 17, I had reputation among the people in my world. I had sucked more dicks than the average hooker. I had slept with men of every race creed and color. You can even throw in a mentally challenged lad or and autistic child as well. All because I loved getting sex. I think that a penis is the sexi... Read full Story
Regina10 2020-09-16 5,860 Crossdresser Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Ass to Mouth
75%
So good fuck with me and my klients.
Hello, I am Francesca, and I offer company to couples and women. A few days ago, a couple hired me for two hours.The woman was fucking me with her strapon while I was stroking the man's cock. She was pushing her hard cock deeper and inside me, I could feel my ass dissolving more and more. I turn my ... Read full Story
Francheskahotass 2021-08-11 3,763 Crossdresser Amateur Group Sex Cumshot Shemale Fucks Guy threesome Ladyboy Lingerie Guy Fucks Shemale Sex Toys 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 5,734 Amateur Cumshot Latina Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale cum in mouth
100%
My Sugar Daddy Fucked My Girlfriend...And I Joined In
I am a shaved-smooth, boyish bisexual male slut. At 43, I still look and feel young, and I enjoy the feel of and attention from older men, the older the better, 55 and up, with gray hair, wrinkles, and very hairy chests and bods. My Daddy, a 70-year-old White man that fits this description, "owns" m... Read full Story
Chrissy Tunnell 2022-04-12 3,223 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
100%
My Sugar Daddy Spanked Me & My Girlfriend (I screwed up again)
In my last fantasy article I explained how my Sugar Daddy allows me to date girls since I am bisexual and attracted to them too, but they, and in fact anyone, are not allowed to touch me intimately without explicit permission from my Daddy. Anytime a girl wants to touch me: kiss, hold hands, put her... Read full Story
Chrissy Tunnell 2022-04-12 2,633 Crossdresser Amateur Big Tits Shemale Fucks Guy Fetish threesome Blowjob Big Cock Ladyboy Shemale and Girl Guy Fucks Shemale cum in mouth
88%
Alex and Jon
Alex was not beautiful, but had a sexy attractiveness that most could not help but take a second look. This was the case with Jon as he searched adult Friend-Finder ads for someone that would satisfy his desires and dreams of a companion. Alex, a transgendered Filipina girl, had the bronze skin colo... Read full Story
Jon Paul 2022-09-21 5,802 Group Sex Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale cum in mouth
100%
How A straight tatted white guy turned me out to a femboy
So I met this straight white guy on an app (wont say) hes tatted a bit thuggish and likes black femboys I noticed. At that time in my life I really didnt embrace being femme I was kinda in the middle doing the cute gay twink boy thing. He didnt mind me presenting male he did like black guys or femme... Read full Story
Ezra_Kyle25 2024-07-18 5,268 Crossdresser Amateur Ebony domination Guy Fucks Shemale Interracial big ass Homemade sissy femboy interracial fuck
92%
My First Time
****This is not my story but i am uploading on behalf of my friend. Hope you enjoy it.**** My story is 100% true, I have been wanting to touch a big penis for a long time, im addicted to looking and watching guys play with there’s on web cam. One day I decided to search for a nice big cock on Fac... Read full Story
SachinJoy 2018-10-04 10,315 Shemale Fucks Guy Big Cock Ebony
90%
Saving My Marriage
I love to write Erotica. For story requests please send me a private message or email noirenoire10@gmail.com It was our anniversary. Today made five years that my wife and I have been married and we were taking a road trip to celebrate. I chose our destination but I let her choose all of our a... Read full Story
therefill05 2021-02-16 6,623 Cumshot Bareback Creampie Shemale Fucks Guy threesome Blowjob Big Cock Ebony domination Sex Toys cum in mouth
50%
arrombado no cine santana
fiquei um bom tempo sem aparecer no cine santana mas em um domingo qualquer resolvi ir la pra dar meu cu pras bonekas ... ao chegar perguntei pro cara da bilheteria se ele podia indicar alguma travesti bem ativa e que gostasse de comer um viado enrustido que nem eu rs ...ele riu e disse que la dentr... Read full Story
Dave_itaflex 2021-07-30 1,348 Shemale Fucks Guy Big Cock Ebony
80%
Fucked by Priscilla Gaucha
This black woman always drove me crazy, I always liked her photos and videos on the internet. Unfortunately, when I had the courage to face it, she moved out of state and ended up being left in the lurch. However, one night driving by, I came across her. She was beautiful, strong thighs, well made-... Read full Story
mauricioportoalegre 2024-05-09 3,936 anal Amateur Shemale Fucks Guy Big Cock Ebony
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 11,703 Group Sex Big Tits Bareback Creampie Blowjob blonde Asian Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth double anal
36%
Nice guys finish last!!!
Wish I didn’t get rejected from so many females in my life and having more as friends!!! It makes me wanting to give up male pieces and wanting to be more female then male. All the time the thoughts flooding my mind about cutting my penis off and starting over!!!... Read full Story
matjohn 2019-08-20 3,967 Crossdresser Big Tits Bareback Creampie Shemale Fucks Guy Fetish threesome Ladyboy redhead shemale + shemale
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 5,545 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
100%
Couple and a Tranny
There is a saying that a single man looking for companionship and good fortune will seek someone for marriage. Lydia and I met several months ago on an online dating site. We agreed to meet at a bar restaurant for drinks and initial meeting. She was at the bar wearing a yellow sundress, white painte... Read full Story
Jon Paul 2022-09-20 5,879 Cumshot Outdoor Latina Bareback threesome Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth double anal
69%
Pune crossdresser Night Girl
Hi friends, I hope you liked my earlier stories. This is my new story about a lady boy / crossdresser / sissy boy. Around 2 years back I came across a profile on Planet Romeo with name Nightgirl. I sent her message that i found her sexy and attracted to her and wanna meet her. I am alway... Read full Story
Stud4Shemale 2017-05-22 8,003 Crossdresser Asian Ladyboy Lingerie domination Guy Fucks Shemale cum in mouth
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 6,461 Amateur Shemale Fucks Guy Blowjob Asian Ladyboy Ass to Mouth cum in mouth
83%
Wife Left Me so I Could be a Girl
I Am The Girl My Wife Did Not Want As the only child of a single mother I grew up around all things feminine. Having lingerie and stockings drying in the bathroom was normal for me and I always loved how pretty the full cut nylon panties and slips with tons of lace looked. I lived at home with... Read full Story
ASSEaster5678 2018-07-09 10,969 Shemale Fucks Guy Ladyboy Mature
66%
Be My Bitch
After a long day at work, I get in my car, and look forward to the long drive home. It gives me time to unwind and relax. I try to forget about the hectic office and concentrate on my beautiful girlfriend waiting at home with that warm smile that she greets me with when I get there. However, tod... Read full Story
Go Balls Deep or Go Home 2018-08-06 32,043 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
37%
Wedding Night Surprise
its my big dream to marry one women in our night wedding in the bed when i start to make her naked a discover i big dick between her legs wow she demand me to hide this secret and i accept ans she abuse to take me and more...... Read full Story
BIG DICK HUSBAND 2018-12-06 15,972 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy Blowjob blonde shemale Big Cock Asian Ladyboy Lingerie domination Mature Homemade Ass to Mouth Surprise Weddings night husband
100%
HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
CDDIXIE4U 2019-01-08 14,641 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
30%
Versklavte TabuTv
Hi. Ich bin die Petra, 37 Jahre alt und seit ca 3 Jahren fühle ich mich in DW wohl. In den letzten Jahren habe ich mich mit dem einem oder anderem Kerl getroffen und bin mit ihm in Kontakt geblieben. WAS ER BIETEN MÜSSTE. 1 Er sollte nicht unter 45 Jahre sein 2 aus LK clp vec dh os ol del hb whv ... Read full Story
Petradwtclpoloshbvec 2019-08-15 3,550 Group Sex Shemale Fucks Guy Fetish Ladyboy domination Sex Toys
69%
TS Fiorella in Frankfurt
Recently I was visiting Germany for a conference. I was staying in the city close to the train station and checked out the red light district nearby. Walking through the red light district is an experience, on every corner and many places in between there are multi storey brothels where you can wan... Read full Story
xanykeyx 2019-10-24 11,790 Shemale Fucks Guy Ladyboy tgirls frankfurt crazy sexy
45%
Threesome with random muslim men from Dubai -
As you all know, most of the meetings with my clients happen in good 3-star or 4-star hotels. Clients normally visit my hotel room and have fun. This exciting session happened during my stay in a 3-star hotel room in Bangalore on March 1st and 2nd. I had bookings for both the days and was prepare... Read full Story
Manusha Tranny 2021-10-14 9,450 Crossdresser Cumshot Outdoor threesome Blowjob Big Cock Asian Ladyboy gangbang domination Guy Fucks Shemale Ass to Mouth cum in mouth