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My first time crossdressing with a man
It was Christmas night 2016 and I had gone out to the bar with a few friends. Came home a little tipsy and very horny! I rushed to my room, took off all my clothes and put on a very sexy, slutty outfit (black lace thong with matching bra, a blue sweater, black mini-skirt, and black knee high boots) ... Read full Story
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A pervy uncle invited me to his house at 10 PM..!
It's been 8-10 years now, I had this amazing experience. I was standing at the bus stop in my area/street(my daily routine), one uncle was watching me but I ignored eye contact as I feel awkward the way he was looking at me because I act straight in public and I felt that he's seen my girly ... Read full Story
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A Boy and Laura
Jonas was in a hotel enjoying the last days of his vacation in Cabo Frio, Rio de Janeiro. Sitting at the bar drinking an orange juice and watching the landscape, he saw a woman approaching, wearing a purple bikini that made up her breasts well, but kept her waist covered by a flowered thong that als... Read full Story
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Um Garoto e Laura
Jonas estava em um hotel aproveitando os últimos dias de suas férias em Cabo Frio, Rio de Janeiro. Sentado no bar bebendo um suco de laranja e observando a paisagem, ele viu uma mulher se aproximar, usava um biquíni roxo que lhe compunha bem os seios, mas mantinha a cintura coberta por uma tanga flo... Read full Story
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Premiere pipe sans capote
Je dois aller revoir mon amant, qu est un homme qui a pas loin de la soixantaine d'années. Je l'ai déjà vu deux fois et sucer à chaque fois avec capote. La prochaine fois je dois le sucer au mois de janvier (oui planning compliqué) mais cette fois sans capote ! Il a fait le test HIV, no souci. I... Read full Story
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Hello!
Hello, I am posting this as a story because I couldn't couldn't  say everything I wanted to in me profile. I have just joined AShemale, I am a mature chap who had been on XHamster for nearly two years,  I love crossdressing and gurls, I have been dressing regularly for many years and before that... Read full Story
LanaLouissa 2021-11-22 2,431 Crossdresser
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Ein Wochenende zu Gast
Wo sind diese schöne Zeiten hin, alles ist vergänglich. Ich habe mir überlegt dass man seine Erlebnisse mal aufschreiben sollte, um sie für die Nachwelt zu erhalten. Mein aufregendstes Erlebnis war auf jeden Fall als mich eine Männergruppe von 6 Männern nach Hannover auf ein Wochenende, (von Freita... Read full Story
Undinerose 2021-12-02 1,676 Amateur Group Sex Creampie Blowjob gangbang Mature
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Hung Trans Lesbians Fuck Two Ladyboys
Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... Read full Story
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First time doing that!!
So I love to dress like a girl and have done since I was about 15, but being married and all it’s a bit hard to do it very often,. I’m a local tradesman so am out all day in my van and have a good knowledge of the area I live in, or so I thought. About 2 miles from my house is a crushing site tha... Read full Story
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think about cock all the time
i find myself looking at chicks with dicks all the time. i love them. they turn me on so much. i cant stop thinking about being with one and im going to be with one very soon. i cant wait to swallow all of her shaft. every inch of it. and when she starts to cum i will suck it in deeper. fuck that tu... Read full Story
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Sissy gets her Prezzie
Justina woke up on Monday morning and was already tired, she had been dogging till 3 and her little ass was a little bit sore. She made her way to the bathroom and had a pee, brushed her teeth then headed for the kitchen to make coffee. As she was walking her phone went off, she had a text from ... Read full Story
Samantha Jewels 2022-01-06 3,022 Stockings Crossdresser Cumshot Bareback Blowjob Big Cock gangbang domination Mature Homemade Ass to Mouth
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Quick trip to the park
Monday Morning again, I hate Mondays, why can’t the week start on Tuesday! Thought Justina ,while she stood semi naked in the kitchen drinking her coffee with a semi. I finished my coffee and made my way to my bedroom to get dressed. As I entered my bedroom i spotted my new dress i’d bought on S... Read full Story
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Not your usual birthday present
So here we go again “Happy Birthday” to me, at 51 it’s not that great really it’s just a reminder your getting older!! Anyway here I am 51 having an absolute ball and fulfilling my wildest dreams, Justina likes being out of the closest and loooooves cock.. So for her birthday she hopes someone has ... Read full Story
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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 2,519 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
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my mornings are so difficult
I really should go to work. but i am obsessed with being a sissy. i spend the morning in chastity, skimpy clothes, makeup, and dildos. what should i do?... Read full Story
Sissy Slut Lorielle 2022-10-26 3,158 Small Tits Amateur Masturbation Blowjob Sex Toys Mature
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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 3,840 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
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Mommy, can I be your fuck-toy?
I saw my step-mom taking a shower by accident or so I thought. It was not until I saw her pretty big she-cock jus hanging there between her sexy well defined legs. It was even hard & it was already as big as my cock when its hard. It looked so big that it was a bit scary yet some muscle in my anus s... Read full Story
Curious_billy 2022-11-22 6,935 Amateur Cumshot Masturbation Bareback Shemale Fucks Guy Blowjob Big Cock Lingerie Mature Homemade Ass to Mouth cum in mouth seduction
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Alessia and I shock our guest!
Alessia was sat on the couch and I was sitting on the soft fur rug between her legs. We were relaxing and recovering watching an old movie. My ass was still feeling hot and wet after Alessia had earlier fucked me hard and long and I had returned the favour to her. But that is another dream! So back... Read full Story
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Kelly's First Encounter With Alessia
I jumped nervously with a start, as the doorbell rang. It was Alessia – I had been waiting for her all morning, and was gradually getting more nervous as time passed. This was to be our first encounter, and I’d been looking forward to it all week. Opening the door, I saw that she was taller tha... Read full Story
Alessia Travestita 2023-01-31 4,176 Crossdresser Blowjob blonde Big Cock Mature
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Captain John’s Playmate
Alessia Travestita’s Adventures – Episode 1 – Captain John’s Playmate. It was forecast to be a gloriously warm and sunny day, clear blue skies with a gentle warm breeze from the South. So I decided to leave the town behind and head out into the countryside for the day, get some fresh air, toning ex... Read full Story
Alessia Travestita 2023-07-13 4,461 anal Crossdresser Bareback Blowjob blonde Big Cock Lingerie Guy Fucks Shemale Mature Ass to Mouth cum in mouth
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MILF Alessia Travestita finds a bottom boy pt 2
Several days ago, Alessia a beautiful Transsexual with a huge cock seduced Stan on their cruise ship. He willingly and enthusiastically sucked her cock and gave her his ass. She brutally throat fucked his mouth before pounding his ass. They spent over two hours together until they were interrupted b... Read full Story
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What I like
I like cum from cocks, a copious creampie dripping from a pussy, or licked off a warm body. I'm an older guy but I'm still fit, active and horny all the time. I like to masturbate while looking at porn with a prostate stimulator up my ass, wearing nipple clamps and a cock ring after smoking some pot... Read full Story
SylvesterLeChat 2023-08-15 4,389 Masturbation Creampie Blowjob Big Cock Ladyboy Mature small cock sissy cum in mouth
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my new life with my sister-in-law
Yesterday, I went to visit my brother's newly-divorced ex-sister-in-law in her brand-new apartment. It was meant to be a friendly visit and an opportunity to discuss her new start in life. To describe her to you, she's a slightly chubby woman in her forties, blonde hair, blue eyes, very charming wit... Read full Story
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My story
Please don't hurt me, I whimpered softly. Oh no my Lil slut, mommy has no intention of hurting you but making your fantasy become real, she said. But your thing, its kinda big. I'm a bit scared, I said. Mmmmmm, don't worry baby. Mommy wants this to be so good that you become my steady, she said... Read full Story
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