Training My Sissy Body

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I felt Benn move behind me and line up with my hole. He hadn't lubed up and I was expecting resistance and maybe a little pain as he pressed forwards. What actually happened was his cock slid in, all 8" in one go. My pussy offered no resistance at all thanks to the dildo training and I was still slick with lube.

"See? This is the real you. Just a happy slut with a dick deep inside her."

As he thrust slowly in and out, I could feel his whole cock and it was exquisite. Warm and soft and just the right length to make me feel it deep inside. This wasn't like one of those stories where the wrecked hole of a sissy felt nothing, my hole felt everything and had just been trained not to resist, to open up like a real pussy, to let a cock in easily. I could feel him pounding away. The pressure building on my prostate. I was loving this; it was who I wanted to be. I didn't need my cock to enjoy sex, I needed someone else's cock to enjoy sex. This was better than any time I'd fucked someone, this was the real me. As I thought these thoughts, my orgasm surprised me and I shook with pleasure as a tiny spurt ejected from the chastity cage. I didn't have much cum left so it was more a drip than anything. As I came, Benn must have felt it and started an orgasm of his own. He thrust as deeply as he could and held there, filling my insides with his lovely cum.

"You did well sissy, that felt great. I told you the training would pay off".

He untied me from the bench, and I shakily walked back to the bedroom. His cum leaking slightly from my ass. He removed my cage for me, and I pulled a tight satin thong up my legs. This held my cock even tighter than the cage but was more comfortable. The back of the thong also helped keep the gooey cum from leaking out. I felt so feminine with my man's cum inside me. I pulled a satin chemise over my head and got into bed. Benn left me to fall asleep and went to his own room, after all I was just a sex toy; he didn't need to sleep with me.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
MilllMilll4 months ago

i love the story. i love sissybois training takes years and sometimes harsh discipline like caning to uncontrollable tears

4yourpleasureiam4yourpleasureiamover 1 year ago

You are a sissies dream come true 💕 you

Nikkitv500Nikkitv500over 1 year ago

Loved this first part and would love to experience a fukin machine, always been a wish of mine, looking forward to next part

SailingforfunSailingforfunover 1 year ago

Hello,

I loved your story and writing style. You also create very exciting word pictures.

Thank You!!

Scott

sissymark79sissymark79over 1 year ago

Fantastic start! I can't wait to read more. This was very sexy!

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Down the Sissy Rabbit Hole A reluctant sissy gets forced to be the slut she wants to be.in Transgender & Crossdressers
Made Into His Girl Luke is tricked into chastity by Sissy and her brother Jake.in Transgender & Crossdressers
Feminized by BBC Friend Ch. 01 My BBC friend slowly feminize me.in Transgender & Crossdressers
White Dom Turned Sissy for BBC Alpha white man learns his inferiority to BBC.in Transgender & Crossdressers
Hypnosissy 01: Becoming a Cocksucker Straight guy watches porn tapes that are not what they seem.in Fetish
More Stories