My First Session with Her

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

When I got there, Jane was waiting for me at the door. At first, she didn't know how to react. The look on her face was a mixture of shock and amusement. I can tell you the look on her boyfriend's face was a little different! Anyway, I walked in and gave her a hug, and noticed they had kindly packed up all my stuff! "Aw, thanks Jane," I squealed as I squeezed. The boxes were even in one spot, and I walked over and bent down to pick one up.

"Nice tat," Jane said. "I never thought you were the type. Although, I guess I was wrong about a lot of things!"

"What?" I replied.

"On your back, nice tattoo," she repeated. "A nice little tramp stamp, it seems fitting. You didn't know about it? What kind of arrangement do you have with this woman?"

In all my primping and preening and staring at myself, I guess I'd never really taken a good look at my lower back. I went into the bathroom and took a look. It was a nice tribal design, with some chains subtly worked in. There was a butterfly as well, and it looked very well done. On closer inspection, though, the body of the butterfly was really a cock, and on either side was a woman's head and neck, bent at an angle to look like wings! I took a few steps from the mirror, and decided one would have to be very, very close to me to see that, but still! Ms. Andrea had truly marked me as her own.

I went back out and tried to pick up another box, but it was too heavy. I called the butler at Ms. Andrea's, and he said he would send a few guys to pick up the rest of my stuff. Ms. Andrea told me to get home, because she had an important meeting in a few hours, and required my services. Jane and I hugged goodbye, and I gave her boyfriend an awkward "ass out" hug, and he tried to cling too long! Then I got in my car and drove away.

When I got home, I rushed into my room and put on the lacy black push up bra, "BITCH" thong, heels, and short blouse, skirt and jacket I had worn to the office on my first day. I felt bad that I had nothing else, but my specially ordered suits had not been delivered yet. Ms. Andrea wanted to wait until after the surgery to ensure that the new ones would be a proper fit. My new tits actually were bigger than my inserts, somehow, and stuck out even further in the suit. My ass and legs looked stunning in the little skirt! I put some large dangling hoop earrings in my newly pierced ears. There was a shiny piece of metal that said, "SLAVE," which I quickly figured out was a dangling navel ring. I put it on and tugged my blouse down as well as I could. Then I swept my hair up into a bun and right as I was about to leave, I remembered something I though Ms. Andrea would like. The pink jeweled butt plug would be a great addition to my outfit! I bent over, slid the cool metal plug into place, tugged down my skirt, and tottered into Ms. Andrea's office. My hips swayed and my tits bounced with each step!

Ms. Andrea was happy to see me, but also very stern. "Listen, Ashleigh. This meeting is very important. Ms. Gilbert is a tough negotiator, and I'm going to need you to be on top of your game, do you understand? I need her to know that I am in control around here."

"Yes Ms. Andrea," I replied.

Just then, there was a knock at the door. I bounced over and answered it. The woman at the door was about thirty, medium height, medium build. She was wearing a power suit and sensible heels. "Hello, Ma'am, my name is Ashleigh. Let me show you to Ms. Andrea," I said politely. The two women went to the conference room, and sat down at the big table. I let them talk for about five minutes, and then came in with some coffee for each. Ten minutes later, I went in to check on them, and see if they needed anything else. While I was picking up Ms. Andrea's empty cup, she told me it was time. I went over to pick up Ms. Gilbert's cup, bending down to reach it.

My short jacket and blouse rode up, exposing my tattoo. I reached back to cover it, but Ms. Andrea stopped me. "Take a closer look," she said to Ms. Gilbert. Ms. Gilbert craned her neck over to examine my tattoo, and gasped. "That's right," Ms. Andrea said. "Those are chains, and that butterfly is really two women sucking a cock. I made her get that. Check out her navel ring!" I obediently showed her the "SLAVE" jewelry that adorned my belly button. "Actually, I made many changes to 'her.'" 'She' used to be a man. I lured him to me, and then took over his life." "Raise your skirt bitch," she growled at me. I did as I was told, and rolled up my skirt enough to show a little bulge in my thong, and the plug in my ass.

Ms. Gilbert gasped again, as I took off my blouse and jacket, and pulled down my bra, to bare my tits, per Ms. Andrea's command. "She's totally mine now," she laughed. "I own her, and I control what goes on around here. Make no mistake about my abilities. Now, I am willing to make this deal with you, but it is going to be a fair deal. What does she need to do to convince you?"

Ms. Gilbert started to get her bearings back, and a smile crossed her face. "You know I'm a sucker for slutty blondes with big tits. Congratulations, you did your homework. I think she can convince me to make this deal," she said, as she eyed me up and down.

I dropped to my knees, and looked up at her. "How may I convince you, Ma'am," I whispered sexily, as I rubbed her nylon covered thighs. She simply rolled up her skirt the rest of the way, pushed her thong to the side, and pushed my head into her pussy. In no time, I had her moaning, and she came all over my face. Not satisfied with my own efforts, I went back in for round two.

Ms. Andrea laughed behind me. Very close behind me. In fact, as I was licking, I felt her hands tweaking my nipples. I moaned into Ms. Gilbert's pussy, and then I screamed as something bit into my nipples! Looking down, I saw that Ms. Andrea had attached clamps to each of my nipples! Ms. Gilbert laughed and smiled, and started tugging on them, to encourage me to eat her faster or slower. Just as I got used to that, I felt the sting of the paddle, and Ms. Andrea was back there paddling my ass, as Ms. Gilbert continued to torture my nipples! They kept it up until Ms. Gilbert came again, and said she needed a moment to recover.

For a few minutes, I just knelt there, in heels, a skirt, thong, and tits pushed over the top of my bra and clamped, face plastered with cum. I looked over and saw Ms. Andrea coming toward me with two strapons. "Let's seal this deal by double teaming the bitch," she said to Ms. Gilbert. Ms. Gilbert nodded, and I dutifully fitted them both with the cocks that would soon be destroying me. Ms. Andrea grabbed me and told me, "Do your duty, bitch." I stood up and bent over the table, reaching back to roll up my skirt, pull my thong to the side and spread my ass cheeks. Ms. Andrea took her place behind me, laughed, and slid her cock into my ass. No matter how many times I'd taken it, it still felt amazing, and I moaned as she fucked me. Ms. Gilbert got up on the table and as soon as her cock was at the right level, I moved forward and took it gently into my mouth.

Ms. Andrea must have felt that she wasn't demonstrating enough control over me, so she gave the nipple clamp chain a sharp tug, which caused me to cry out, but I did manage to keep Ms. Gilbert's cock in my mouth. "You have such a well trained slave," Ms. Gilbert commented. "It's best we keep her in her place, though," she continued; as she started to really skull fuck me. I gagged a little, and she pulled out and slapped me in the face with her cock and then jammed it back down my throat. I felt the two women really got into a good back and forth motion and I rocked with them, trying to maximize their pleasure, as I knew was my duty. Ms. Andrea had taken off my bra. The chain of the nipple clamps, as well as my tits, brushed against the table as they bounced beneath me. My "SLAVE" chain also scraped along the table, and my hoop earrings hit my face and shoulders as they slammed me back and forth.

"I really do think the terms of the deal are fair," Ms. Gilbert stated. "I would love to do business with your company. This deal will benefit both of us greatly, now, and into the future."

"I agree," Ms. Andrea said. "Our companies compliment each other very well, and together we can really make some moves in this market." "Let's switch."

I enjoyed a moment of emptiness in my mouth and ass, before they switched, and Ms. Gilbert took my ass, and Ms. Andrea filled my mouth.

"She even does ass to mouth. What a depraved anal slut," Ms. Gilbert commented, before they went back to their business talk.

They were using me, and talking like I wasn't even there! As odd as it may sound, it turned me on even more. This is the life I chose, this is the life I wanted, and now I had it. How many other people can say they enjoy their job like I do?

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
humbleslavehumbleslaveover 12 years agoAuthor
Thanks!

Thanks for the positive feedback. I do have a follow up in the works. The problem is, it's already 10 pages, and I'm stuck. So, it will be posted, but I want to make sure it's ready first. Stay tuned;)

AnonymousAnonymousover 12 years ago

I definitely want to work for Ms. Andrea. Do you know if she is still hiring ? I would accept any job, even "janitress", as long as I get to be transformed into a sissy slave. And in fact working as a "janitress" would be great, more humiliation.

freemic3040freemic3040over 12 years ago
LUCKY GUY!!!

Loved this story and am veryyyyyy jealous of this lucky "man"!

Would love for a woman to make me her secretary and rule my life!!

Hope that add to this story!!!! It was fantastic!

Share this Story

Similar Stories

Tamed by Meg Megan introduces me to the pleasures of being penetrated.in Anal
Her Presents She had a number of surprises for him.in Fetish
Making The Perfect Husband Before his wedding, submissive desires overcome Mark.in Mind Control
My New Life with Her Former man, now secretary, continues her journey.in Transgender & Crossdressers
Mercy Rent Theo makes a deal with his attractive landlord.in NonConsent/Reluctance
More Stories