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Becoming addicted to her she-cock
"I'm going to make you a very happy woman tonight when I slowly but firmly slide my long, thick, hard she-cock all the way up your tight virgin ass tonight baby" Alma whispered in my ear as we left the bar I had ?mistakenly? stumbled into. I shuddered with both fear & a bit excitement. I don't why ... Read full Story
Curious_billy 2023-05-07 7,615 Teen (18+) Amateur Cumshot Asian Ladyboy domination Homemade cum in mouth
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Meine erste Erfahrung Teil 2
Ich knüpfe hier direkt an meine andere Erfahrung an, da ich glaube ich kann vielen die Angst nehmen ihren ersten Schritt zu wagen ;) Ich war zu diesem Zeitpunkt 16 und habe einen Tag vorher meinen ersten richtigen Schwanz im Mund gehabt. Diese Erfahrung die mir ein Bekannter meiner Cousine besche... Read full Story
beginnertranny 2023-06-18 2,602 anal Stockings Teen (18+) Crossdresser Amateur Creampie Blowjob Lingerie sissy
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How could I forget my first time .......
"Ok, ok, ok stop. No more. It hurts a bit" I said. "Just relax your ass baby. Push out like you have to go poo", my date said. How did I end up like this? A straight A college student, a devout Christian with a nice gf like me ends up in bed with this sexy woman ...... Ok wait, I thought she wa... Read full Story
Curious_billy 2023-10-29 9,120 anal Amateur Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Big Cock domination Homemade cum in mouth teen (18+)
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Diary of a Sissy
Dear Diary, This time I fucked it up for good... I am completely lost in the viscous cycle of sissy hypnosis. My beta girl nature was starving to be controlled by superior men. The desire to be owned was so intense that made me do something I have never done before in my whole life.. this time I ... Read full Story
KittyHot 2023-12-21 7,708 Amateur Cumshot Fetish domination climax sissy chastity cage sissification master daddy teen (18+) mental domination
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Sweet Stephen Wears A Slip.
Stephen is a 'petite' boy, just a little smaller than his Aunt Melanie. Petite figures ran in the family in both the females and males. Stephen cut quite the girlish figure in his Aunt Melanie's pastel-pink full slip. 'Oh, my, don't you look just so simply darling, pretty missy!" Melanie cooed, ad... Read full Story
ALEXEAMES 2024-01-14 5,351 Stockings Crossdresser Amateur blonde Lingerie Shemale and Girl small cock sissy femboy teen (18+)
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Bobbie the Ballerina Boy!
Bobbie Lynn looked absolutely adorable in the pink ballet-leotard, shiny white tights, and teensy pink dance slippers his mommy had just bought him as an early surprise for his birthday. Fastening the fluffy, frilly pink tutu around his waist, she cooed smilingly, "Looks yummy like cotton-candy, doe... Read full Story
ALEXEAMES 2024-01-14 5,047 Stockings Crossdresser Amateur Lingerie pantyhose small cock Homemade sissy femboy teen (18+)
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Becoming Kacey
I indulged my crossdressing opportunities as often as I could, but as time went on, the chances grew further and further apart. Although I couldn't play dress up in my alone time, the fantasies never seemed to cease. When I entered high school, I dated girls and enjoyed the young passions that teena... Read full Story
KaceyKlarissa 2024-01-16 4,255 first time Crossdresser Amateur Homemade sissy femboy shemale + shemale romantic teen (18+)
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Edging lessons for Hannah
Hannah and I began spending our weekends together. She didn't have a job and I was always free those days so every Friday or Saturday night became sleep over night where we could be two 18 year old sissies, doing each others makeup, playing dress up and sharing our deepest desires. Now that our rela... Read full Story
KaceyKlarissa 2024-01-25 3,912 Crossdresser Amateur Cumshot Masturbation Fetish Big Cock kissing Homemade sissy romantic cum swap edging teen (18+)
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Andy In Pantyhose
He had the house to himself for a few hours. Andy slid his older sister Kelly's taupe nylon pantyhose slowly up his nice, smooth legs, wriggled them up around his narrow boyish waist the band snapping in place. His penis was so stiff against the wispy fabric! He sighed happily. Sitting down on ... Read full Story
ALEXEAMES 2024-01-18 5,517 Stockings Crossdresser solo Amateur Masturbation Fetish Lingerie pantyhose Homemade sissy femboy teen (18+)
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Dress-Up-Girly Time!
"Let's go, 'Little-Missy,' it's our 'dress-up-girly time.'" Sandy knew better than to argue. Besides he really didn't mind being dressed up as a girl. It was kind of weird at first, when he first started playing 'dress-up-girly time.' His mom had brought home several boxes of clothes that no lo... Read full Story
ALEXEAMES 2024-01-27 5,776 Crossdresser Amateur Lingerie small cock Homemade sissy femboy teen (18+)
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Sex With Not Just 1, But 3 Females
When I was 18 years old, I was still occasionally going to the Highbridge toilets in Lincoln on a Saturday and getting paid for having sex with guys be it sucking cocks or being sucked off, dirty chats, wanking them off or giving or taking anally. I never turned down any form of payment, money or... Read full Story
Linda Tiffany Vista 2024-05-07 2,416 Stockings Crossdresser Amateur Lingerie cum in mouth teen (18+)
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From boy to crossdresser episode 2
940 / 5.000 I had already learned to masturbate, I used to cum several times a day and it continued until I got older. I was still going to school and I was more lustful than before. I remember when we used to go to my aunt's house, my brother and I would sleep next to the cousin, when every... Read full Story
Nickinickharddick13 2024-09-02 883 Amateur Big Tits Masturbation Homemade teen (18+)
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"Sissy Ricky."
This is from an email I received from a sweet girl who recounts this true experience: "When I was 10 I had a friend, Ricky, who had four sisters. The two oldest had left home already, the younger two, a few years older than he was, lived still at home. As their parents had theater jobs that kep... Read full Story
ALEXEAMES 2024-09-03 1,144 Crossdresser Amateur Fetish Lingerie Homemade sissy femboy babysitter boyish teen (18+)
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A Girl For The Holiday!
(What a festive account of a boy at a Holiday Pageant from Sharon!) There were a few occasions in my childhood but this was one that I really enjoyed. I had been dressing in secret a lot at this time and there were a couple of times where mum had dressed me up, the earliest at about five years o... Read full Story
ALEXEAMES 2024-09-17 356 Crossdresser Amateur Lingerie sissyboy Homemade sissy femboy sissification young girlyboy youthful teen (18+)
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Go-Go Girlie!
Back in 1968, I was 9 years old. The style at the time amongst my third-grade classmates was mini-dresses, fishnet stockings and go-go boots. I became captivated by my female classmates and what they wore. Each day I wondered what pretty or cute outfit they would wear. So was it curiosity or envy th... Read full Story
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Tiny Tranny.
My name is Tina, and as early as 5, I remember my mom saying that she really wanted a girl when I was born she was kind of disappointed, but was so glad that I looked like a cute little girl. So, much to my amazement and total delight, she began dressing me up as one! We lived in a one room apart... Read full Story
ALEXEAMES 2024-09-19 114 Stockings Crossdresser Amateur Lingerie sissyboy Homemade sissy femboy sissification young youthful teen (18+)
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They Called Him "Anna."
Growing up, I had only a mother and sister who wore dresses every day back in the 50s and early 60s. I wore my sister's clothes every day and her pajamas to bed. I never wanted to wear pants because I wanted to be a girl just like my sister. One time I heard my mother tell her friend that she though... Read full Story
ALEXEAMES 2024-09-20 87 Crossdresser Amateur sissyboy feminization Homemade sissy femboy sissification young Boy youthful teen (18+)
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Early Yearnings
My name is Denise and this is a short account of my first discovery of the feminine side of my nature and my early yearnings to be a girl. Since the age of eleven, I have always been aware of a desire to be a girl, preferring to play with them rather than with the other boys. Not that I didn’t play... Read full Story
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:Like A Good Girl Should.
Now that I'm older I have come to realize that I'm more Bi-sexual than straight. Even though I'm a married man and have adored women all my life, I still have found myself thinking back to when I was seduced in my young teens by a much older man. Now, with the internet I can look at all kinds ... Read full Story
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A Trick and a Treat!
It was Halloween night and I was getting ready to go out "trick or treating". I was going to wear my pirate costume from last year but it didn't fit. The costume box said for boys ages 6 to 11, but I was only 12 yrs old and only about 5' 2" and no more than 95 lbs, so I thought I could wear it a... Read full Story
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