• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Mass Sissy

Mass Sissy

Well my mistress wanted me to post this short story of my latest sissy humiliation for even more humiliation so here goes...

So it was a typical Saturday and I was on my way over to my mistresses' house, she wanted me there bright and early. I arrived at her house promptly at 4:00am and when I arrived I was informed that I would be spending the entire weekend with her. She gave me my first assignment of the day. I was to take a shower and shave my entire body from my neck down. Lucky for me I have a baby face and am always clean shaven on my face. When I got out of the shower my mistress informed me that I was going to be punished for my time taken in the shower. She took me by my hair and bent me over a stool within seconds my wrists were strapped in and I had no choice but submit again. Then came a butt plug it was only about half an inch larger than the one that I was used to but it felt much larger in side of my sissy pussy. I was instructed that I was to put my panties on and stockings with my pink toenail polish on and walk down the street to the beauty salon and tell them mistress Tassa sent me. I walked the 2 miles to the salon and when I walked in the lady behind the counter ended up being an old friend of mine from high school named Miranda she kindly asked if I was waiting for a friend and I told her the truth I was here for me. I informed her Tassa sent me and before I knew it they had me sitting in a chair and I received a manicure, pedicure, eyebrow shaping, facial and evening style makeup. I was then given a letter from Miranda.

Jessy,

You are to walk home in the clothes given to you by Miranda in the back room.

MT

Well with no other choice I walked into the back room and on the desk was a pink with black lace corset. There were the b cub breast forms that mistress had bought me, there were also a matching ping thong as well as dark black panty hose. As I closed the door there was a black V-neck evening gown with a slit up the thigh that came all the way up to my thong and next to that there was a long blond wig with natural highlights made from real hair. And finally there was a note.

Jessy,

Put these on and walk to the mall, before you can walk home you must get 5 phone numbers from guys. Then walk home and give them to me.

MT

After I got dressed I left the office and walked through the salon which was now packed with young women well my age but in their twenties. As I walked to the mall, (my first time being a sissy in public, But I dare not disobey my mistress) I tried hard not to show my embarrassment and then I started to think like a girl. The first number I got was a friend of mine whom didn't even realize it was me. Then I walked to the food court and found a table to sit at. I opened the purse to find my compact and lipstick that I was given and started to apply the light pink lipstick (I have gotten real god at this since I do it all the time at home) when a group of guys walked by. (Hmmm Idea) I informed them I was going to throw a party and wanted some people there to get to know as I was new to the area. I ended up with 8 phone numbers and decide to walk home. When I arrived at my mistresses' house I was rewarded for going over what was required to do, the butt plug was removed. My mistress then preceded to pound me with her 8in long strap-on and let me cum but I was to cum in my panties and put them back on. She left me there for a few minutes and went to her phone to call some people. When she returned she handed me my phone and said we were going to see a few of my friends and my new friends tonight. As 4:00pm came around I was blindfolded and told that we were going somewhere special and different.

We drove for what I thought was hours before we parked I was then led out of the car up a few steps. I heard some men inside talking. I was led into a small room with no lights and was told my next task. I was to suck off anything in mouths range but not to swallow. I was to let them cum on my face and dress. I was told not to worry and that they were all clean and plenty to get me drenched in cum. I felt around for a few minutes, after my mistress left and was introduced to the first cock coming in through the wall. Time slowed after that moment and it felt like hours before my jaw started to ache. I lost count after the 20th penis to come through the wall but my face was now covered in cum and my dress was completely ruined. What seemed like 100 cocks later my mistress came in and informed me that there was over 90 guys that showed up just to fill my mouth and that I was now leaving the small confines of the closet to show all of them what a little slut I was. I was not to inform them that I was a guy but let them relish in the fact that a stunning woman just gave them what they all wanted. As I was dragged out of the closet I saw them all I felt so embarrassed most of them were close friends from work and even more were from the college I went to. And even more embarrassing one was my best friend from when I was a kid. I was blushing from underneath the cum, and finally my mistress turned to me. I am taking you to dinner now, you are not allowed to change or wash up. It's a small restaurant and it is absolutely packed I had to do some things to get a table. Now walk to the car and get in I'll be right out just need to pay the guy for letting me use that glory hole for the three hours you were in there.

When she returned to the car we left driving back towards town we stopped at this sports bar and walked in she promptly sat me down at our table and we ate. I felt so embarrassed every guy in the place was soon staring at me. You look gorgeous to these guys mistress Tassa said. She will be at the glory hole at the book store tomorrow if you want your chance. She said so everyone heard. As we left I felt so good that the night was over but was informed that I was to sleep without cleaning up. I felt so slutty with all that cum crusted to my face...

Well I was only told to write this part but I was so horny when I got home that mistress Tassa let me cum while she fucked my ass with her dildo and sucked me off.

MISTRESS TASSA,

HEY EVERYONE, YES I DID MAKE HIM DO ALL THESE THINGS AND MORE. I HAVE THE PICTURES AND PLAN ON DOWNLOADING THEM TO MY LAPTOP AND POSTING THEM SOME WHERE. I WILL LET YOU KNOW SOON WHEN THEIR UP. JUST COMENT ON THIS AND GIVE ME SOME NEW IDEAS FOR HER SISSY TRAINING.

LOVE TASSA

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Mass Sissy

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 49 milliseconds