Sissy Sessions Ch. 01 - Sex Stories

Sissy Sessions Ch. 01

Note to readers: This story is the first in an anthology-style short story series. I plan to write them so that each one is unique. I'll re-use characters in more than one entry from time to time. I'll also always do my best to write these so that you can read each story on its own. Read the series in whatever order you want. Enjoy, and thanks for reading!

"Your father works extremely hard to make sure we have a roof over our heads!"

The last words I heard my wife say as I walked out the door tonight.

Now the words I'm hearing are,"your mouth feels so good, bitch."

The words came from our landlord, Darrell.

I only earn about $40,000/yr from my work from home job as a Support Specialist. It's not enough to cover rent and all the necessities that come with supporting my family. My wife works part-time at the grocery store, and my son is now in his sophomore year of high school. It's a private school, and it gives him the best shot at getting into a top-tier university. The tuition is not cheap.

A few times per week, I have to take up shifts at my second job. Non-negotiable. There's no possible way our family can pay for all our expenses if I didn't take up this job. I go to work at this second job in the evenings only. I can't afford to lose my day job either, so my days are not open. Shifts can be anywhere from 1 to 3 hours long.

If I'm being honest, the pay for my part-time job is more than the pay from my day job. It pays more because the work is a lot ...

... harder. It's some of the most difficult work I've ever done in my life.

"Yeah, you've gotten so good at sucking my dick. You look so good. You're loving it."

Darrell's words rang loud in my ears as I looked up at him.

To make sure my son has the best opportunities in life, I debase myself at Darrell's feet. This evening, he has me in a lacy black thong, matching black stockings, a black crop top, and pink high heels. The stockings are fishnets, and the heels are open toe. Darrell likes to see my painted toenails peaking through. In bright pink lettering across the front of my top, read the words"Daddy's Bitch". Around my neck is dog collar. Tonight, it's the pink one. The name tag is the shape of a miniature dick. It's engraved with 173, my family's apartment number.

I always wonder how many more tags I would find if I searched his penthouse. I used to tell myself I can't be the only tenant he owns. I don't bother thinking about it anymore.

A few minutes ago, I finished getting dressed after doing my hair and makeup. About 40 minutes passed since I arrived. I don't get paid for these 40 minutes. I can't get ready to his satisfaction any faster. Darrell has specific desires. I lost count how many times I've done this now. It's been going on for over a year at least. I think it started a few months before my kid's freshman year. We needed the money for a down payment on his tuition. I spent most of my prep time on the makeup look tonight. For my shoulder-length ...