Sort by
Relevancy

Free Stories

0%
Tranny sex
I dressed in her bathroom. Comfortable nylon stockings and my black body with suspenders, black thong, my beautiful silicone breasts in C-cup and between blond wig with ponytail up on my left shoulder. High heels had to wait this time. Then I pulled on my red short dress in jersey. He who runs away ... Read full Story
shemale lover 2012-05-19 3,059 tranny Stockings fingering oral sex deepthroating
100%
My meeting with tranny milf Sandy 54
Wanna tell you about my meeting with Trannymilf Sandy 54! I met Sandy through an add in a pornographic magazine I was 23 then so she was 31 years older than me. Wanting for long to meet a much older tranny beauty I got really excited when she agreed to meet me. We met in her apartment after I ran... Read full Story
shemale lover 2012-10-13 3,843 tranny Stockings milf
80%
Outdoor Tranny Sluts Lust
I wake up really early one morning with my cock throbbing hard under the sheets. I got a white camisole on. Out of bed i go with a desire to vouyer and masturbate somewhere around my home. I'm home alone so i head out to my garden with my cock bouncing up, down & dripping cum. It's about 5am... Read full Story
Tracy Bel 2023-02-14 6,079 Crossdresser Outdoor Fetish Homemade cum in mouth shemale + shemale
90%
First Outdoor Fuck
Sat in my office with nothing to do was making me tired there was no customers to serve which was slowly driving me mad, what was worse was the hot weather outside which always makes me horny, knowing I had all my girly clothes in the boot of my car was making my cock twitch in my cheap nylon work t... Read full Story
shemale lover 2012-12-19 6,794 Crossdresser Outdoor ass fucking pantyhose heels
50%
Manusha Tranny at an adult cinema
Rajeshwari Theater in Bangalore!! An adult cinema which plays B grade sex movies, but more popularly known as a gay paradise for having open fun at the theater. I have been hearing about this from my top friends and CD sisters for quite a long time. Some of them had visited this place and had dif... Read full Story
Manusha Tranny 2021-05-06 12,577 Crossdresser Group Sex Cumshot Outdoor Blowjob Lingerie
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 5,935 Cumshot Outdoor Latina Bareback threesome Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth double anal
90%
Riverbank Tranny Fucktoy
Hello to all of you that read my first true story about outdoor sex. This is another account of a meeting I had in the middle of a city near a river. It was late one summers evening when I met up with this sexy young Portugese stud I had been messaging on a gay dogging site. I had been chattin... Read full Story
shemale lover 2014-12-03 5,147 tranny hardcore suck Big Cock cum ass fucking deep throat
50%
KING OF TRANNY CHASERS ENTRY 1
IT WAS AROUND 1AM AND MY GIRL FRIEND GINA AND I ARE GOING AT IT.HER NAKED BODY WAS HANGING OFF THE BED IN DOGGY.HER BIG CARAMEL ASS CHEEKS JIGGLED AS A POUNDED FROM BEHIND. SHE WAS SCREAMING "YES BABY" AND MOANING NON STOP..AS BEAUTIFUL AS SHE LOOKED AND HOW AMAZING HER BACK SHOTS WERE LOOKING..W... Read full Story
Ghostface drillah 2024-07-02 3,139 Amateur Big Tits Masturbation Big Cock Ebony Guy Fucks Shemale big ass Homemade Ass to Mouth cum in mouth
100%
KING OF TRANNY CHASERS ENTRY 2
LAST YEAR TO CELEBRATE MY BIRTHDAY I DECIDED TO FULFILL ONE OF MY SEXUAL FANTASITES. I HAD BEEN WITH 2 CIS WOMEN SEVERAL TIMES BUT NEVER HAD I BEEN WITH 2 TRANNIES. MY BIRTHDAY WAS ON A FRIDAY SO I SPENT THAT DAY AND THE NEXT CELEBRATING WITH MY FAMILY AND GINA..THAT SUNDAY I SET UP AND PLANNE... Read full Story
Ghostface drillah 2024-07-04 3,659 anal Amateur Group Sex Big Tits Cumshot Shemale Fucks Guy Fetish Big Cock Guy Fucks Shemale big ass Homemade Ass to Mouth shemale fucks shemale
100%
My wife turned me into her tranny
It all started after our marriage. We have been together for 12 months when she asked me if I would be willing to have her dress me up like a female as this was one of her fantasies. Little did I know where this would lead us to. She was very secretive about her job and I did not bother to ask, I fi... Read full Story
TRTRAIN 2024-01-15 9,920 Stockings Crossdresser Amateur Shemale and Girl domination pantyhose Homemade sissy shemale fucks female
100%
Dirty Tranny Bitch
I was feeling really horny, massive nervous anticipation. I was all dressed up, looking for my first taste of cock. My name's Nikki, I was aged about 25 or 26 at the time, only 2/3 years ago, but I was fed up being the `closet' tranny tart, I wanted to try out some cock; in short, I wanted dirty ... Read full Story
shemale lover 2012-05-01 3,970 Stockings anal sex Cumshot oral sex finger fucking
78%
A night out with Tamanna
We had been chatting online for a few weeks , when Tamanna said she would love to come it with me. The doorbell rang at my flat and I wobbled on my stripper shoes to the door. The butt plug Imwas wearing made me squeeze my ass cheeks together and gave me a wiggle in my black latex dress to die for... Read full Story
shemale lover 2014-07-21 5,525 tranny Stockings Cumshot Lingerie Latex
83%
Tranny gang bang
It was pretty dingy in here, the sunlight came through a old dirty high window and a single fluorescent tube did little to lift the overall gloom. An oppressive smell of stale piss also hung over the whole place. What was I doing in here? In truth I did not know but I was 16, horny and wanted to ... Read full Story
shemale lover 2015-02-27 6,915 tranny Cumshot suck gangbang facial oral sex bukkake
100%
Glory Hole Memories
The Glory Hole Fun Begins Locking the car I look towards the building. The entrance is open, but from my position it isn’t possible to see inside, the bright sunshine making the entrance look black. My heels click on the tarmac as I approach, my legs beginning to tremble with fear and excitement.... Read full Story
Sexy Michelle 2024-03-13 4,927 Stockings Crossdresser Outdoor Blowjob Big Cock Lingerie
100%
Tranny Night Out
Tranny Night Out and One Kinky Session Guess I should start by explaining myself, as a young guy I always knew I was not the same as a lot of my friends and enemies for that matter, girls had no interest in me at all apart from ones who were long term friends. I knew something was wrong but neve... Read full Story
shemale lover 2013-05-01 8,203 Stockings suck Lingerie ass fucking stroking
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 9,335 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
82%
Tranny Gas Station Attendant
This happened about ten years ago and I thought I'd share it with you all for your enjoyment and mine! Like I've said before, although I'm bi-sexual, I don't walk around checking out other guys, nor do I like to be intimate with one. Sure, some might consider taking a cock in the mouth or ass intima... Read full Story
shemale lover 2014-06-29 8,471 Stockings shemale cumming
100%
Claudia Coming out adventure part 1
*Author's Note: This story starts off being told in First person and after awhile the story shifts to third person* Hello everyone, my name is Claudia I am a Cross dresser who one day hopes to be transgendered, although I do not want the surgery, I am looking to eventually live my life full... Read full Story
MissClaudia 2015-01-04 6,389 tranny Stockings suck Creampie ass fucking doggy style Latex
95%
Never Wanted To Be Your Girlfriend Ch. 04
8:20am Monday Morning --------------------------------- "...You can't be serious, Mike. There is no way anyone is gonna believe me," I whispered intensely. I was sitting in the school office dressed in the patently ridiculous outfit Michael had picked out for me that morning, waiting to see... Read full Story
shemale lover 2014-07-21 6,083 tranny Stockings asshole Lingerie girlfriend
100%
Joanna the Tranny Prostitute
Joanna stood on the street corner and casually shifted her posture from one leg to the other. So far it had been a quiet evening for her with few punters around. Not many girls were plying the streets either. She’d had one customer earlier. He had been an Asian guy in a Toyota who’d stop... Read full Story
Joannacd1 2011-11-07 4,746 tranny Crossdresser Ebony
80%
Tranny's First BBC
Sitting on the lounge at my local sex club I was watching the guys go by. You get to notice certain guys going past trying not to look like they are checking you out on the sly (and vice versa) thinking how they can approach me. Normally it’s just the usual crowd of guys but several weeks a... Read full Story
shemale lover 2012-03-28 4,554 tranny cum deepthroating Interracial handjob
100%
Sally another adventure
After the excitement of the past few weeks Sally was planning on a quiet few days with Sue. Trying to live a sensible life as Sam and trying to get his life sorted out. He returned home and took Sue out for dinner and a show and they started to talk about things for the first time in a few days. Whe... Read full Story
shemale lover 2016-05-12 5,486 tranny Stockings nipples
57%
That girl with long cock
She opens the door and says hello and as I walked in this dim lit room with smells of candles and perfume in the air. It put my body at ease. She closes the door and immeditaley she says your mine now. She stood tall 6ft1 long dark tan legs wrapped in sexy pink fishnet stockings that ran from th... Read full Story
blkmale83 2014-10-06 7,969 tranny Stockings suck Blowjob Big Cock oral
85%
Boys to girls transformation with a surprise part I
Boys to Girls with surprise For the first time I scheduled an appointment at a studio that will transfer me into a sexy women. I packed my sexiest outfits and high heels and drove to the next city where the studio is. I told everybody I had to go to a business meeting over the weekend. I arrive... Read full Story
TRTRAIN 2024-09-01 3,004 anal Crossdresser Amateur Group Sex Sex Toys Mature Homemade sissy shemale fucks shemale
50%
Hello!^^
Ciao! this story was created with the help of google translator, so do not judge strictly. I'm trying. I try every day to be better and more confident, but for now I'm still afraid. it seems to me that I can disappoint or not live up to expectations that they will ridicule and mock me, I’m afraid th... Read full Story
kateleto 2023-06-12 4,205 tranny Crossdresser Amateur Outdoor Fetish Homemade sissy femboy Traps story russian cd read
100%
Feriengruss 16.07.24
Heute habe ich endlich jemanden gefunden, der mir einen langersehnten Wunsch erfüllen wollte. Ich wollte, nackig unter dem Mantel und nur bekleidet mit eingeschnürten Titten, durch die Stadt geführt werden, während ich gefilmt wurde. Wir machten ab, als es in Weinfelden gerade einzudunkeln begann. B... Read full Story
Cheryl_F 2024-09-03 888 anal Amateur Cumshot Outdoor Bareback Fetish blonde Big Cock Ladyboy domination Guy Fucks Shemale Homemade pov
92%
My Seductive Secret (True Story)
During my childhood, me and my brother used to play with two other boys who were our neighbors every weekend. One day we decided to wrestle, and I took on the youngest one, (he was about 2 years younger than me, like my brother) and we wrestled in the shed while my bro and his bro (who was my age) w... Read full Story
LovelyLeo97 2019-06-18 14,720 Stockings Teen (18+) Small Tits Crossdresser Cumshot Outdoor Masturbation Bareback Fetish Blowjob Big Cock Lingerie domination Sex Toys Homemade cum in mouth
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 14,684 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
100%
Ho incontrato una Dea
Era una tiepida sera di primavera, erano da poco passate le 8 di sera ed io avevo già cenato, era tutto il giorno che mi sentivo eccitata e la voglia aumentava dentro di me, volevo divertirmi un po' con i miei giocattoli anali, però era troppo presto, la serata era troppo bella ed invitante per rima... Read full Story
Sissy Mari 2022-03-17 2,888 tranny Stockings Crossdresser Amateur Cumshot Creampie blonde Lingerie Homemade shemale + shemale sexy shemale sexy tranny
62%
Crossdressed Lana - Hannover, Germany
Crossdressed Lana - Hannover, Germany Very Sexy & Compliant Sub-Slut Is Searching For Kinky BDSM Live-Dates At Hannover, Germany!!! I Am Bisexual And Want Men, Woman, Couples And Trans For Outdoor, Swingerclub, Porncinema And Public Sex. I Love To Wear Very Hot & Sexy Clothes Like Lingerie, Stoc... Read full Story
Crossdressed Lana 2020-02-06 4,804 Stockings Crossdresser Group Sex Outdoor Bareback Fetish Blowjob gangbang Lingerie domination Latex Sex Toys double anal
50%
She also conquered my soul...
Initiation in a new era... Almost three months since I offered my virginity to a wonderfull he-woman, Selmi... unfortunately I had to cancel the second day we planned to spend together with my LORDESS because I quitted the town where we met the day before. Since, only few summer fling messages...... Read full Story
hippocampus_171 2022-11-22 4,539 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
100%
Dream Bride Tranny
My niece Avril and I rushed along the ground floor corridor of the hotel and made sure none of our relatives were watching us as we disappeared into the room. Inside, we were met by Miss Anne of the Kinky Brides Group, who immediately ordered Avril to strip me naked. "Please, not today,&q... Read full Story
shemale lover 2012-11-13 5,976 anal cum oral Lingerie
100%
Carla goes out
As a cross dresser who loves to dress as a dirty slutty girl I was sat at home thinking about what it would feel like to go out dreesed in public. I had often thought about it but never had the courage to do so. I was so fucking horny and wished I had a reason to go out and do something rather than... Read full Story
Carla Kitten 2018-01-16 8,715 Crossdresser Amateur gangbang Homemade
50%
The BIG COCK that I will eat.
ENGLISH: Hello friends. In the link below, you can see the tranny cock that will fuck me in the days to come. I saw her advertised on the internet, I picked up the phone and called, I will see her when her clinical tests are negative for sexually transmitted diseases, because I will surely swallow... Read full Story
cuchillo 2020-09-18 8,288 Amateur Cumshot Latina Shemale Fucks Guy Blowjob Big Cock Homemade cum in mouth brunette ts swallow cum
100%
My lusty landlord
Gopal Reddy has been my landlord for about 7 years now. I rented his flat back in 2015 at Whitefield, Bangalore and have been staying there with my mom. Gopal Reddy and his wife Manjula are from Anantapur, Andhra Pradesh and they keep visiting us whenever they come down to Bangalore. Both of them... Read full Story
Manusha Tranny 2022-12-12 4,906 Crossdresser Amateur Bareback Homemade Ass to Mouth cum in mouth
100%
Crossdresser 1st time!
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 2013-05-30 8,473 Outdoor Big Cock fingering ass licking virgin public cd piss