Sissy Blowjob Stories

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Ugly Duckling to Sissy Princess Ch. 05

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

Bernice held my hand and pulled me out of the bathroom to her living room where there were five very pretty girls, sissies, I will use the word "gurls" to distinguish them from girls that were born with a pussy. I recognized a few of these gurls from the party at the mansion. The gurls' names Deborah, Jill, Vanessa, Shirley and Anne. Each of them was very...

Allyson's First Blowjob

by sissymaidallyson on Sep 16, 2017
Transsexuals & Crossdressers

I have been a closet cross dresser for many years. A few people knew but it wasn't well known and that is how I liked it. I enjoyed dressing up and prancing around my flat in ladies clothing but I always had fantasies about going further. I kept stopping myself from doing anything further but there was that burning desire to be truly slutty inside of me. On...

Sissy Gets Outed

by nancyvasquez on Sep 16, 2017
Transsexuals & Crossdressers

I was married for 3 years before I finally got caught. It happened when my wife went through my notebooks and found all the gay fantasies I had been writing about. The story she found was one I had just written. It was about a young guy who applies for a modeling job at a gay magazine called TORO. In the story, The young guy goes to the modeling session, w...

Sissy's Decline into a Slut Pt. 05

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Seven: I've been taken, Made into a Maid, Turned out as a Slut. Two days have passed by, it's Thursday morning. Today Master Gage and Master Martin are to arrive by 10:00am. I awake by 8:00am and my stomach is turning. I get up sit on the edge of my bed wearing my sleeping lingerie today it's a white satin full slip, white lace bra and satiny panty....

Crystal: A Sissy Set Free Pt. 03

by InSpectrum on Sep 16, 2017
Transsexuals & Crossdressers

This is a direct continuation from Parts 1 and 2. You should probably read those first, if you haven't already. ***** Before he could think Ryan was gone, Crystal shut the toilet seat re-locked the door and sat down feeling a jolt from his plug, He suddenly felt very uncomfortable, his feet ached from dancing in ridiculous heels, his corset was way too ti...

Mindy's Moving Day - CFNM Ch. 01

by BuckyDuckman on Sep 25, 2017
Fetish

Author's Note: Humiliation, CFNM and pegging lie ahead! I've had this idea for a while about an adventurous married couple on the edge of opening a new chapter in their married life. I hope you enjoy reading it as much I enjoyed writing it! On her first day in town, Debbie and I were Mindy's only friends. The professional moving company hired by Mindy's...

Allyson the Sissy Whore Ch. 02

by sissymaidallyson on Sep 13, 2017
Transsexuals & Crossdressers

Kevin woke up with his head swimming. Kevin...or was he Kevin any more? Was he just Allyson? He looked down at himself and saw his name badge and decided that for now he should just think of himself as Allyson. Think of herself as Allyson. Oh it was just too confusing. As he started to come to terms with what was happening he saw the door of the jail buildin...

Nick and Sandi Meet for Lunch

by sandifeettv on Dec 3, 2017
Transsexuals & Crossdressers

This happened a few years ago, but I fondly remember the day. I'd been cross-dressing for years and had yet to meet someone that was a dominant type. Mostly I met men that only wanted me to get a room, tell them the number and they would stop by and I'd blow them. I passed on that. I met TV/CD's. This was more fun, as we modeled for each other, but every one...

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

The Locker Room Glory Hole

by Sissy_Sammi_ on May 30, 2018
Transsexuals & Crossdressers

*All characters are 18+ ***** The bell rang, rousing all of the students out of their seats. The students stuffed their books, binders, and pencils back into their bags before quickly rushing out the door to get to their next class. It was going into seventh period, the last period of the day for everyone without an after school class. Most students quickl...