Sissy Boy Stories

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Mommy's Boy? Ch. 02

by yr_sissy_toy on Sep 13, 2017
Transsexuals & Crossdressers

I skipped home from school, an expression of the giddy joy I'd felt for the last week. I'd gone from a pansy boy who got teased after school to my mommy's special sissy, who was swathed in the finest femininity the moment I got home. It was delicious, intoxicating even, and I was almost bursting with joy. I'd learned so much in the last week! I could slip i...

The Prostate Exam Pt. 02

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. She then persuaded him to...

Lady's Sissy Bitch Ch. 01

by HorroticaWriterJCarter on Sep 16, 2017
BDSM

It was an exciting day. Lady was coming to visit and I knew I was in for a weekend of extreme pleasure mixed with extreme pain. It had only been ten months since we had met at a play party but it felt like she had known me my entire life. The minutes passed like hours and I could feel the desire growing inside of me like a wildfire. Lady was beautiful. Her...

Black Licorice

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

My name is Jamie. I am 19 years old. This is the story of what happened to me Halloween one year ago. It was the last week of October and the leaves had turned brilliant shades of orange, red and yellow. The nights were getting cooler. Everything you could imagine was pumpkin flavored. Usually I get psyched for this time of year but things were different f...

Mikey becomes Melodie Ch. 02

by tiffanyfoxe on Jul 14, 2020
Transgender & Crossdressers

I lay there under this incredibly beautiful fully transformed girly-boy, her lipstick covered lips still softly and tenderly kissing me, kissing my lipstick covered lips, my rouge covered cheeks, my eye shadow covered eyelids and my mascara coated lashes, showing how much she loved having me under her, her huge still hard cock buried deep inside my pussy/bot...

Escapade

by Da_Vida on Sep 13, 2017
Transsexuals & Crossdressers

I'll never forget Homecoming this year. My boyfriend, Blake, came by my dorm to pick me up around 6 pm. He was in a very excited state and I could tell something was in the works. I asked him why he was so hyper and he told me that he was about to win the sex escapades, which was an annual challenge his fraternity put up each year to its members. There was a...

Sissy Pool Wager Pt. 01

by maxy007 on Sep 14, 2017
Transsexuals & Crossdressers

My name is Max, and I'm your typical high school graduate. White, short brown hair, blue eyes, skinny, and 6'4. I never had muscles or any masculine traits other than my lanky height. I had just finished high school, and had 4 months off before university to myself! As you could imagine, an 18-year-old horny boy like myself really got into my porn, which f...

Feminizing First Step Ch. 03

by antares34 on Oct 21, 2019
Transgender & Crossdressers

(All characters are age 18+) *** I felt like I was losing control. My body and mind were becoming less and less masculine with every passing day. And I was secretly ENJOYING it. I couldn't help myself. Every time I looked in the mirror, I found myself loving the ever-changing reflection. First, my dyed pixie haircut. Then, my bikinis. Then, my nose, ear, a...

The Dominatrix Order Pt. 04 Ch. 01 - Med

by Jwwsmith on Apr 10, 2019
Fetish

THE DOMINATRIX ORDER: FEMDOM EROTICA 4 AFTER CARE BY J.W. SMITH Early one morning, roughly three miles outside the Femininus walls, Nadia's Slave boy veered from his usual path on his morning walk, and his ocean blue eyes fixed upon the Ladorian Harbor docks where the medicines and other exports were shipped out on the boats. A unique, intimidating vessel...

The Slave and the Sissy Ch. 05

by Sputnik57 on Sep 12, 2017
Transsexuals & Crossdressers

Ayesha was not to be denied; slave was rampant after witnessing the erotic antics of the maids, and was anxious to please Ayesha quickly, so that he may watch over Pepper; she was so soft and vulnerable. Slave's cock rose quickly as he sniffed at the gloriously rich scent of the dusky beauty's thong. She smiled with a sense of admiration as he licked and lap...