Sissy College Stories

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Sammi Starts Camming

by Sissy_Sammi_ on Dec 3, 2017
Transsexuals & Crossdressers

Sam had always been rather small and feminine. As a guy puberty seemed to have missed him which left him in the rather uncomfortable position of being very girly. He was only about 5'8" with a womanly rounded face, smaller waist, and slightly larger hips. He had brunette hair, which for a guy was on the longer end. His lightly tanned white skin pieced with...

Truth or Dare Takes a Turn Pt. 01

by Cutiepie183 on Sep 14, 2020
Transgender & Crossdressers

I'm sitting at home on summer break, just a few weeks after graduating high school. I hear my phone buzz and glance over to take a look. I can't believe what I'm reading! "Luke Elwood has invited you to his event: graduation celebration party tonight at 8pm." You see I was never really one of the cool kids in high school - I never really had any friends but...

If Women Ruled The World Ch. 01

by chronoxxx on Sep 15, 2017
Fetish

It was at age 18 my life began to change dramatically and, I guess, I didn't realise just how profound those changes were going to be. We'd all been horrified by tales about the great big world outside, but no one took them seriously. And besides, information is really hard to disseminate when you're a man. Nobody trusted the rumours from beyond the perimete...

How I Became a Sissy for BBC

by Caged4goddessd on Mar 12, 2019
Transgender & Crossdressers

It really all started in college. I was a fairly typical and somewhat popular guy. I was involved in a few different clubs and a member of a popular fraternity on campus. Of course, this led to me knowing quite a few of my classmates and at the time I had my share of success with the females in my classes. It was my junior year and at the time I was dating...

Sissy Pills Pt. 02

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

There's nothing like waking up like this. This being after being fucked. Not fucked but riding a dildo until you have a sissygasm. And yet that's not the first thing in my brain waking up. It's the cum. It's that eating my own cum. And really feeling this need sort of burned in my brain from the semen and the pills. I really, really want to suck a co...

Sammi Meets Teddy

by Sissy_Sammi_ on Dec 8, 2017
Transsexuals & Crossdressers

Ever since Sammi was born Sam had been working his ass off, both in pants and panties. His grades in school improved rapidly as his outlook on life improved, and before he knew it he had sent away college applications and received acceptance letters. He knew where he was going to college, and before he knew it he was graduating. The rest of the year coasted...

Blackmail by Choice

by Sissy_Sammi_ on Mar 6, 2018
Transsexuals & Crossdressers

Christopher was twenty six and had gotten his degree from a prestigious university in southern California. He had worked for the best grades possible all through high school, and all through college to get his degree. It worked out because in his field he was already getting job offerings before he had graduated even. So when he did graduate, he already had...

Falling into Being a Sissy

by Sissyhalo on Dec 12, 2018
Transgender & Crossdressers

My name's Sonny and well life's been pretty damned golden for me. I used to be a hockey jock in high school and was a defenseman so I was kinda big and tough and had all the usual good stuff going for me. Middle classed family, decent money for all of that, lots of high school pussy and even more in college. Being a jock in college doesn't prepare you for...

Neighbourhood Terror to Sissy Pt. 23

by Fibaro on Aug 24, 2020
Transgender & Crossdressers

Chapter 25 While Marcy was doing her best to reapply the many makeup products Stephanie had shown her to use, Stephanie was making quick work out of repairing her own makeup. It was very clear that she was very practiced at it since she only needed a few minutes to reapply the complex look. The rest of it was spent sternly supervising Marcy's job. When she...

From Brother to Bitch Ch. 01

by Mixedwritings1993 on Sep 13, 2017
Fetish

(This is my first erotic writing, so I would appreciate any comments or suggestions from any readers.) James was an ordinary college boy, around 18. He has quite a good look and athletic body, and does lots of extracurricular activities. But due to his extreme shyness, he is still a virgin, uncommon for a boy of 18 in the States. Well, one day after a har...