Sort by
Relevancy

Free Stories

88%
Surprise Ending (Part Two)
My curiosity, unconscious urges, and my horniness pushed me into action. I gently cradled Karla's balls in my left hand while my right hand settled on her taut ass. I caressed both and then let my left hand move on to her now blood engorged shecock. I am a pretty big dude, but I could hardly get ... Read full Story
Chantel13 2022-08-23 4,165 Crossdresser Amateur Group Sex Outdoor Big Cock Shemale and Girl redhead cum in mouth
100%
Surprise Ending (Part Three)
I rolled my dick around her hole to spread the precum off it and lubricate it. The feeling was sensational and I couldn't spend much time easing my way in --I shoved right in the the hilt in one steady push. Karla practically jumped off the couch and screamed. I thought maybe I had hurt her (I am... Read full Story
Chantel13 2022-08-23 4,046 Crossdresser Amateur Group Sex Cumshot Outdoor Creampie Shemale Fucks Guy Big Cock Shemale and Girl redhead Guy Fucks Shemale Ass to Mouth
100%
Surprise Ending (The End)
Karla struggled a bit to get the huge, bulbous head of her cock inside of me. It was like my ass had licked a battery. A charge went through my body that while painful, was exhilarating and exciting. "Ahhh," from my lips was all the encouragement I could offer and Karla took it. She steadily push... Read full Story
Chantel13 2022-08-23 5,230 Amateur Outdoor Shemale Fucks Guy Big Cock Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Trans sucht Daddy
( Anonymität Diskretion ) Schreibe eher über mich Geschichte meine Sex Lebenslauf !!! kommt Später Da ich ja aus Erfahrung weiß da viele Herren auf Anonymität angewiesen sind und wert darauf legen dürfen mich sehr gerne was mir auch sehr Gefällt mit Maske im Hotelzimmer + Ferienwohnung besuche... Read full Story
Tranny ( Für den ) Herrn 2022-08-24 1,749 tranny crossdressing transgender tv crosssdresser cd solo daddy sissy crossdresser daddy fucks sissy grandpa DWT TV Transe BI
50%
Mein erstes Zofen Date mit Herrin und Master
Bei mir war es ein reiner Sex Abend, nach kurzer Begrüßung und auch 1 Std quatschen habe ich mein Zofen Outfit angezogen, dazu musste ich Armmanschetten und ein Halsband anlegen und die Clit habe ich in einen Käfig gesperrt. Den Schlüssel habe ich dann meinen Master gegeben. Danach ging es in Garte... Read full Story
Die_Susi_CD 2022-12-01 1,769 Crossdresser Amateur Bareback Blowjob domination cum in mouth
100%
The WearFemme
The times between his fantasies have begun to shorten and he knew it wouldn't be long now. One chance glance at an outline in gym shorts as a guys walking in the wind, or seeing a girl with similar features wearing revealing clothing. The thought of it is almost overwhelming now and he has to focus ... Read full Story
Jayde Love 2022-12-01 3,073 Small Tits Crossdresser solo Amateur Outdoor Masturbation Fetish Homemade pov
100%
Been a while and oops!!
Hi been a while since I let you know what’s going on with me. Well after spending the last couple of months getting on with stuff and trying to behave ( boring) I finally snapped and needed to go to the woods for some well deserved dick!! I got myself dressed up as normal, g string , stockings, ski... Read full Story
Samantha Jewels 2022-12-10 3,179 Crossdresser Outdoor Bareback cum in mouth
50%
SISSY AWAKENING
- Trou de gloire du sex-shop - "Hey bébé, quand est-ce que tu rentres à la maison?" le message texte bourdonnait doucement. Sortant discrètement le téléphone de ma poche, je tape "Même heure que d'habitude, juste après 5 heures, pourquoi... quoi de neuf ?" C'est mon amante Sarah, ma meilleu... Read full Story
Femboy 2021 2023-02-17 973 Stockings Crossdresser Outdoor Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth
100%
I met a guy in the nightclub and I didn't tell him I was Trans
I’d worn an absolutely killer dress just to make sure I got what I was looking for that night. Dancing under the lights I could feel eyes all over me, and as the evening progressed men became bolder and bolder about approaching. This one was athletic, sexy and had all the right dance moves, at least... Read full Story
Madison Heights 2023-03-25 6,338 Cumshot Outdoor Blowjob Big Cock cum in mouth club outfit Surprise Cock Partying surprised
80%
I got humiliated in a catfight
Im a crossdresser and I am very feminine and extremly dainty. I was attracted to a man at a park I went to. He knew I was a crossdresser. I would always say hi when I saw him, but that was it. One day he asked me(on a rainy day as I was getting in my car), do I have a boyfriend am I bi, he wanted to... Read full Story
Kaylamoore994 2023-03-26 5,458 Crossdresser Outdoor Masturbation Fetish Ebony Ladyboy Lingerie humiliation fight sissy crossdresser catfight
0%
Cruising for Cock!
Cruising for Cock. Not my Story But very hot for you all. A few years back now I took a drive to a dogging & cruising hot spot in the Haldon Hill Forest on the A38 in sunny Devon. I'd been once b4 with a trucker who picked me up hitchhiking. (That's another story) WOW his cock was huge 8.5" @ lea... Read full Story
Streethawk75 2023-04-18 4,046 Stockings Crossdresser Amateur Cumshot Outdoor Masturbation
100%
Caught Spying 👀
Caught spying to 1st time sucking. A few years back now I took a drive to a dogging & cruising hot spot in the Haldon Hill Forest on the A38 in sunny Devon. I'd been once b4 with a trucker who picked me up hitchhiking. (That's another story WOW his cock was huge 8.5" @ least. matched his muscular a... Read full Story
Streethawk75 2023-04-18 4,877 Crossdresser Outdoor Masturbation Shemale Fucks Guy Blowjob Big Cock
0%
Darkness Fantasies #2
Darkness The engine warning light was blinking rapidly, its red urgency causing a rising panic in Jack. Limited mechanical knowledge, an unknown area of the county, pitch blackness and hammering rain, none of these signs a good omen.He groaned inwardly as the engine coughed, spluttered and then jus... Read full Story
Streethawk75 2023-04-18 3,909 Amateur Cumshot Outdoor Masturbation Fetish Lingerie big ass
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 3,635 tranny Crossdresser Amateur Outdoor Fetish Homemade sissy femboy Traps story russian cd read
100%
Mein erster Blowjob
Nun hat es endlich mal geklappt. Ich schrieb längere Zeit mit einer anderen Sissy und lernten uns immer besser kennen. Nach mehreren vergeblichen Versuchen sich mal live zu treffen, hat es dann endlich geklappt. Wir trafen uns auf einem Parkplatz. Ich hatte bereits einen heißen String, Strapse und e... Read full Story
Maja 2023-07-04 1,315 Stockings Small Tits Crossdresser Amateur Outdoor Blowjob Big Cock Lingerie Homemade sissy
100%
Vanarama Pt1
I had a Monday off work,went shopping and on the way home it hit me. The urge. The urge for cock. I think we all know, when it gets us, there's no point fighting it. So I diverted slightly and headed for my local cruising spot. Normally, I just go cruising at weekends, the layby on this Monday was p... Read full Story
Streethawk75 2023-06-16 4,881 Stockings Crossdresser Cumshot Outdoor Masturbation Big Cock
100%
Vanarama Pt2
So we head to his van, and I slip over, try and act casual and now covered in mud, I suppose everyone else who's parked up in that layby see the two men who have been in the woods together emerging. I know in the past I'd have bottled it. "Too many people have seen us!" type of thing. Except...now, ... Read full Story
Streethawk75 2023-06-16 4,670 Cumshot Outdoor Big Cock domination
50%
Μια βολτα στη Λ.Καβαλας.
Γεια σας και παλυ. Σημερα θα σας πω μια ιστορια που εζησα.Ως συνηθως οπως σας εχω ξαναπει μεσα απο το τζην μου φοραω καλτσες ζαρτιερες στρινγκ κι ενοητε παντα κανω κλισμα ξυρισμενος μπρος και πισω γιατι ποτε δεν ξερεις τι μπορει να προκυψει οπως κι εγινε.Πηγαινα μια μερα βολτα καπου στην Λ.Καβαλας ... Read full Story
crossofia 2023-07-29 3,156 anal Crossdresser Amateur Outdoor Lingerie big ass
50%
Alles was wichtig sein könnte
❤ ❤ ❤ Ein paar Antworten zu meiner Person ❤ ❤ ❤ ❤ Name:Marcel ❤ ❤ Alter:32 ❤ ❤ Haarfarbe:blond ❤ ❤ Größe:174cm ❤ ❤ Schuhgröße:42,5 ❤ ❤ Familienstand:Ledig ❤ ❤ ❤ ❤ ❤ ❤ ❤ ❤ ❤ ❤ ❤ ❤ ❤ ❤ Bist Du devot: ja ❤ ❤ Bist Du rasiert:ja ❤ ❤ Wie rasierst du dich:nass ❤ ❤ Wie oft rasierst du dich:2 bis ... Read full Story
NrwMarcelBi 2023-09-06 955 Amateur
100%
3. ΣΥΝΕΧΕΙΑ ΝΟ 3
Πολλες φορες ειχαμε συναντηθει απο τοτε.Αφου μεχρι και τα ονοματα μας ειχαμε αλλαξει σε γυναικια.Εμενα μ' λεγε Σοφια κι εγω τον ελεγα Τζουλι.Ενα Σαββατο λοιπον ημασταν σπιτι του που ελειπαν οι δικοι του, μας ηρθε η ιδεα να κανουμε παρτουζα.Το προβλημα μας ηταν το τριτο ατομο.Ρε Τζουλι του λεω τι θα ... Read full Story
crossofia 2023-10-01 4,110 anal Stockings Crossdresser Amateur Cumshot Outdoor Masturbation Lingerie pantyhose Mature big ass sissy cum in mouth
50%
Meine sexy set card
Name: gaggedthonglover Geschlecht: männlich Haarfarbe: braun Haarlänge: lang Größe: 187 cm Gewicht: 81 kg Bist Du dominant: nein Bist Du sadistisch: nein Bist Du devot: ja, zu 100 % Bist Du masochistisch: nein Bist du rasiert: nein Bist du tätowiert: Ja Rauchst du: Nein Welche ist... Read full Story
gaggedthonglover 2024-01-11 374 Crossdresser Amateur
0%
Lara : γαμήσια στα τσοντάδικα
1. Μεγάλη πουστοπαρτούζα στον Αρίωνα Την πρώτη φορά που έφαγα πολλές, μα πάρα πολλές πούτσες μέσα σε μιά μέρα, ήταν τον Αύγουστο του 1999. Τότε που γνώρισα τον Τιμόθεο. Δευτέρα πρωΐ ήταν. Εκείνη την εποχή, το τσοντάδικο που σύχναζα πιο πολύ, ήταν ο Αρίων. Παρ’ όλο που μ’ είχε καταξεσκίσει ο Τιμό... Read full Story
hotmatureLara 2024-01-30 2,673 anal Group Sex Outdoor Bareback Creampie sissy
100%
A Series of Perverse Dreams, Part 1
My relationship with Hannah had always been mutual in the idea that neither one of us was ever truly the dominant one. It was an equal, balanced relationship of mutual fucking and sucking. However, I had REALLY enjoyed being made into a submissive sissy slut by Nikki. Something changed in me after o... Read full Story
KaceyKlarissa 2024-02-24 3,632 anal Small Tits Crossdresser Group Sex Big Tits Outdoor Big Cock gangbang domination sissy femboy Ass to Mouth cum in mouth
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 2,647 Stockings Crossdresser Outdoor Blowjob Big Cock Lingerie
100%
Beginnings
I always knew I was a bit different though due to social stigma I didn't fully accept it till later in life. I wish I knew then what I know now and had embraced it sooner. Puberty hit and gynecomastia (formation of women's breasts) hit harder (36C). I was teased, groped constantly and was even force... Read full Story
CD_Danielle_Doggy 2024-03-26 1,932 Crossdresser Outdoor cum in mouth
100%
Dogging in the Park
The last two nights have been great fun in our local park. There is a parking lot where guys gather after dark and I was one of them. Both nights I was dressed up as a slutty CD with a black bra, fake silicone tits, black pantyhose and a short miniskirt. First Night: After waiting about an hour a... Read full Story
Rocky8844 2024-04-02 1,958 Crossdresser Outdoor Blowjob
75%
Passion in the Rough
Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... Read full Story
Regina10 2024-04-27 1,167 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
85%
Fucking with Gina!
Hi! Here I am with my own story! I’m a young white guy, a good looking son of a bitch! When I was a college student, one of those numerous young people who always rush for something, then I was a focus of interest for lots of chicks around! But then something changed. Changed a lot. As I remem... Read full Story
shemale lover 2014-05-13 6,458 tranny asshole Blowjob
80%
Trance club
It was the worst day in my life. My girlfriend Ally and I had been quarreling and rowing for several weeks, we were on the verge of breaking up. I just wanted her to be happy. I lived my life for her. I guess I stood no chance to make her smile at me again. We broke up. Ally said everything was chan... Read full Story
shemale lover 2014-05-25 7,601 sucking shemale
57%
Morning Routine at the Mansion of My Misstress
My eyes open with the gentle humming of my small alarm clock. I quickly shut it off so as not to disturb anyone else in the room. Its 4:30am, well before light creeps into the day and the room is now pitch black. Very quietly I rise up on my hands and knees and crawl off of the small doggy bed on th... Read full Story
shemale lover 2014-06-05 4,185 shemales sucking Fetish
94%
Becoming the girl i really am part 2!
I smiled up at my best friend, dressed up in sexy lingerie and smiled, "Can i dress up too?" i asked in a hopeful tone of voice. "Oh, wow, really? Yea sure!" brian answered with excitement in his voice. "Go into the guest room, my sister keeps all her clothes in the dresser ... Read full Story
shemale lover 2014-06-11 5,333 first time shemales cum
86%
Miko and Mali; Thailand's finest teen sisters
Last August my friends and I went on a “lads holiday” to the beautiful country of Thailand. We had booked a fortnight, which was to consist of five nights in a city hotel in Bangkok, and the remainder in a stunning 5* resort in Phuket. It was my first time in the country, my friends hav... Read full Story
shemale lover 2014-06-25 7,955 shemales taboo lesbian sex
62%
Its about me
Hi Sweetie it's 6:30 Sat morning. Woke up early and feel like writing about me. Well lets see I am married now for 13 years happily I must say. Though the side in me you see exists in me always in different degrees and phases through out my life I am now 55. Early in life young childhood I discover... Read full Story
ZizaZee 2015-05-09 3,406 domination crossdressing
66%
Plant Food
Written by: Slayzer Rewritten by: Hobgoblin ~~~ “Where the hell are you, Terry!?” Rebecca snarled, tirelessly searching for her little brother. Rebecca, a pretty sweet sixteen dressed in casual in khakis and a pink T-shirt, was pissed off. It was Saturday night and she’... Read full Story
BoyVixen 2016-03-26 6,666 asshole cum incest
80%
You Never Forget Your First...
Every girl remembers her first taste of cock. I would guess most T-girls especially – after all, we’re women too, but we have a cock sitting between our legs – just out of reach of the lips but for the most flexible. Oh, how I wished I could wrap my tongue around myself and pleasur... Read full Story
shemale lover 2011-07-30 3,346 tranny suck cum
78%
The Hottest Of The Teen Transgender Stories
She was a cheerleader in college and I was…well. Me. I lived one of those transgender stories where I was still stuck in the middle of my transition and I wasn’t a girl anymore, but I wasn’t the guy she needed. She had every single guy in the campus she wanted and I had..well. ... Read full Story
shemale lover 2016-06-06 8,007 pussy fingering transgender
44%
Halloween Disguise
an original story by me. its not true more of a fantasy... this story starts october 14th. first of all i am a 23 year old boy, i just moved to a different state to go to college, i dont have many friends and have only been her a couple of months. today was like any other day, had to wake up e... Read full Story
shemale lover 2011-08-07 4,323 first time shemales gay male
66%
Buffy the Shemale Vampire Slayer Part 4
Damn! Wherever Willow was, she wasn't home. The witch still hadn't returned to her motel room. At least, this time, Buffy hadn't had to rely on Sunnydale's public transportation system. Xander had given her a ride across town. He'd offered to wait, to make sure that Willow was back, but Buffy, wa... Read full Story
shemale lover 2011-08-19 3,598 shemale orgasm nipples
100%
Buffy the Shemale Vampire Slayer Part 5
By the time that Buffy arrived at Rupert Giles' apartment, the former librarian, her ex-Watcher, had just finished reading a new volume of what Edgar Allan Poe, in The Raven, had referred to as a "curious and quaint volume of forgotten lore." He'd just settled the large, leather-bound volu... Read full Story
shemale lover 2011-08-19 3,429 hardcore celebrities shemale
50%
Weekend visitor
Well...my recalling of an experience dressed in a swimsuit didnt seem too popular so perhaps you may prefare the story of a weekend visitor I once had. It was 1981 and I had just got my own place, a nice modern 1 bed flat.Apart from bedsits as a teen this was my first real place of my own. In these... Read full Story
shemale lover 2011-08-22 2,217 anal shemales gay male
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 8,924 shemale transsexual porn star
100%
Seven Minutes in Heaven
This is purely a work of fiction about two 18/19 year olds... It is the summer before our first year of college and we are home alone at his house. My mom works from home, but his place will be empty until his sister gets home from her summer internship. We have been playing truth or dare since... Read full Story
shemale lover 2011-09-20 2,866 first time shemales taboo
100%
Bitch Maker Part 3
"Alex bring me some juice." Sammie said, rolling over in bed and hugging her pillow. "Yes mistress!" I replied, with enthusiasm. I crawled out of bed and walked down the hall, on the way past Tim's room I looked in on him. He lay there silent, his cock trapped in it's new c... Read full Story
shemale lover 2011-09-23 3,793 anal sex licking facial domination
75%
Tranny whore Samara Rosetti at a Trucker's jo
Last night I got a call from a client. He told me to meet him at a small bar close to Olga Street in Stuttgart. He ordered me to dress as follows: Short black leather mini skirt slit up the side, button down red silk blouse unbuttoned 3 buttons, 16cm spiked heels boots, fishnet body stocking, no br... Read full Story
shemale lover 2011-09-25 6,877 anal shemales hardcore
100%
Handjob Positions and Techniques
Hands handle. Usually, touch signifies acceptance, whereas the avoidance of touch signals rejection. Hands are involved in embrace, which implies fondness or even love. Hands welcome. Hands communicate. Hands work and play. Hands massage. Hands manipulate, shape, and form. Hands hold. Hands give. ... Read full Story
shemale lover 2011-10-28 3,715 shemale massage handjob
50%
Thongs
"If you like them, why don't you wear them - as underpants, I mean?" Stephanie asked. "They're not underpants," Brad said. "They can be, if you want them to be." "They're jockstraps." "They could also be used as underpants." Brad hesit... Read full Story
shemale lover 2011-11-16 2,721 anal hardcore Masturbation sucking shemale
100%
Random Thoughts on Tits
Tits. You have to love them! They bounce. They hang. They jiggle. They sway. They tremble. They wiggle. If you're a man (or a lesbian with a strap-on strapped on), you can even fuck them. They can be bound with cords so that, the blood flow to and from them restricted, they turn purple. Clothespins ... Read full Story
shemale lover 2011-11-17 2,486 shemales tits transsexuals
66%
Thongs of Innocence, Thongs of Experience
"If you like them, why don't you wear them as underpants, I mean?" Stephanie asked. "They're not underpants," Brad said. "They can be, if you want them to be." "They're jockstraps." "They could also be used as underpants." Brad hesitat... Read full Story
shemale lover 2011-11-22 2,481 Fetish crossdressing erotic encounters
85%
Black Master, white sissy Part 2
I was a romantic despite the cynicism I projected in my job. This tough black skinhead yob had abused me - he had shaved me, humiliated me and yet for the next week what I remembered most was the kiss. Sure, the abuse had touched something in me but until I had met him it was unacknowledged - someth... Read full Story
shemale lover 2011-11-23 10,178 shemales Fetish bdsm
100%
Alexis Season Part 2
But it wasn't her dick that was bothering her, really; it was the loneliness. Alexis and John had been going out for two months now, but they'd only gotten to first base and lingered there. No matter how many time he told her that he didn't mind that she had a penis, he simply refused to go any furt... Read full Story
shemale lover 2011-11-27 2,856 Masturbation massage softcore
71%
Headmistress' Favorite Sport Part 2
Over the next week the twins trained him further. He was taught how to apply make-up and how to behave in a properly feminine and submissive manner and they trained his movements to be properly feminine. So as not to wear the skin of his ass, the twins introduced a new punishment tool for these trai... Read full Story
shemale lover 2011-12-12 4,691 torture toys bondage and discipline heavy
50%
I am Baaack! Part 1
PROLOGUE: Ross Thorn, aka Nick Mitchell, paced back and forth in his office high up in the Hancock Building. He glanced out the corner windows. North you could see out over Chicago's North Side to almost as far as Wilmette, and east out over the lake almost to Michigan. It was a perfect spring da... Read full Story
shemale lover 2011-12-15 5,114 crossdressing erotic encounters
100%
Story for adults Part 7
Life settled into a routine for Mistress Catherine and her sissy-slave. Alice would mince around in skyscraper heels wearing hotpants and doing her best to look like an oversexed pre-teen with huge tits. Mistress Catherine took her out once in a while, always making sure that these excursions were i... Read full Story
shemale lover 2011-12-21 3,116 bondage and discipline heavy feet reluctant
0%
How I Learned To Love Drag Part 2
Coming from standup comedy, I was used to performing on stage in front of a live audience. ECSTASY didn't for a number of reasons. We could tape at various locations. We could do as many takes as needed. There was less time pressure. Costume and makeup changes with a small cast became manageable. ... Read full Story
shemale lover 2011-12-29 1,849 crossdressing erotic encounters erotic
50%
How I Learned To Love Drag Part 5
"How is it you get the glamorous drag role?" asked May. "Well, Ted Walters said he hired me based on my performance at the Montreal Comedy Festival. There I was doing some impressions. Vocal impressions. A little Jim Carrey, Tom Hanks as Forrest Gump, Austin Powers, and some musica... Read full Story
shemale lover 2011-12-30 1,684 crossdressing erotic encounters fantastic
58%
Preggo Scat Sex
Sara was horny. For any type of sex. She was stuck on a bus heading to her school. After 14 years of wasting her time She discovered her own sexual abilities.She had her first practice by fucking her brother's friend. She didn't come to school to learn. She came to screw anyone in sight. She had ... Read full Story
shemale lover 2012-01-07 11,831 Masturbation lesbian peeing