Pimped Out Sissy Bitch

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.

I glanced at the phone.

"Someone in the room knows exactly what you're wearing..."

It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the woman to whom I'd entrusted some of my deepest secrets as part of a well-paid relationship. She'd been discreet up to now but it was her message that literally caught my breath.

I felt my face burn and I reached for a glass of water to cover my embarrassment. Glancing around the room there were several women and more men. All were good looking and some were truly handsome or beautiful. No one seems to be staring at me... yet.

"You know last night when I said I couldn't see the bulge of your bustier cups through your shirt? I lied."

I was going to faint.

"But you're a good little sissy, aren't you. You're all shaved everywhere, sissy smooth."

My cock started to get hard.

"You're wearing my satin panties I gave you and the satin bustier we bought together to match them."

It was true. It had been an order from Sabine that I crossdress under my suit at my "big meeting". I shifted slightly in my chair and I could feel her tight satin panties on my bottom and the tighter satin bustier around my body. I cursed that I'd already taken my jacket off like everyone else. It would look awkward to put it back on just to speak to the group and now I was going to stand up with boobs in my shirt.

"Silky thigh high stockings gartered up nice and tight..."

Right again as I felt my pants slide across my stockinged leg deliciously. The shock and humiliation of my situation had my cock so hard. I was lucky that the panties channeled it to the side and it hadn't escaped them.

"Just imagine if I had made you wear my special high heels... the ones I strapped you into with locks last night..."

A small groan escaped my mouth at this and a couple people glanced over at me.

"Your turn... give 'em a sexy show, sissy!"

At that moment, I was introduced to speak. I'm sure I looked awkward, trying to keep my erection in the panties and trying to keep my shirt from showing bumps where the filled cups of the bustier were.

Strangely enough, all this distraction allowed me to speak without worrying about what I was going to say. All my practice kicked in and my fifteen minutes of fame went great. I was completely stunned when Mrs. Yakota moved for an immediate vote on my proposal and she cast the deciding yes vote.

I sat back down and wondered if my lingerie and sissy play had actually been key to getting over nerves and pulling off the deal. I accepted congratulations from the people sitting next to me. I waited for another text from Sabine but the meeting ended without anything more from her.

The room began to empty and my phone buzzed again.

"Do whatever she says. You're her sissy bitch tonight..."

Mrs. Yakota, a slender and very pretty woman of Japanese descent, stopped next to me long enough to press something into my hand. As soon as I had a little privacy, I looked at it.

It was her home address with "6pm" written on it. I would have no time to go back to the hotel and change. Something led me to believe that being late was not an option. I collected my things and did the necessary amount of post-meeting debrief with my colleagues but my mind was racing.

"Was Mrs. Yakota a Mistress too? Or a client of Mistress Sabine? Why would she want me when she knew I was a slutty little sissy bitch wearing satin lingerie like a girl? The possibilities flittered around my head unformed, not daring to picture my perverted sissy fantasies.

Arriving at the Yakota estate, I was met by a servant who ushered me into the impressive house as my BMW was valeted away somewhere.

"Madame will join you shortly." With that, I was left alone in a drawing room. To calm my nerves I poured myself a healthy scotch and looked around. There was quite a bit of artwork: small sculptures, paintings, sketches. I took a closer look and was entranced by a full body figure sculpture of a naked, beautiful, slender woman.

"I was a bit younger when I posed for that," came Mrs. Yakota's voice. I blushed, realizing who I was looking at and turned around. "She did a wonderful job I think. She certainly was good with her hands..."

Mrs. Yakota had her long black hair pinned up in a sexy mess behind her head. Gone was the forgettable corporate costume and in its place was a deep red satin robe. The robe was sashed closed but I could tell she was wearing lingerie underneath including red silk stockings down to matching high heels.

"Uh, thank you for your support in the board room today, Mrs. Yakota," I began before a sharp look cut me off. It softened quickly.

"Your proposal might pan out but it was more of a payment. We're here now to see what I paid for. Take off your coat, shirt, shoes, and pants."

I paused but was not totally surprised. I mechanically obeyed her, my fingers nervous at showing my depraved secret identity. When I was done I was standing before her in thigh highs, garter belt, panties and bustier. She came up to me and walked around me as if she was inspecting livestock. Her hands groped my ass and checked for body hair _everywhere_. By the time she was done with her inspection, I was rock hard in Sabine's panties.

"Well, we can't have that," she commented, seeing my erection. "Jerk off into your hand as fast as you can." This made me pause even longer, shame burning my cheeks.

"I'm only going to say this once. You'll do everything I tell you to tonight whether you want to or not. As long as you obey eagerly and without all this hesitation, this evening will not be known outside this house. I can record excellent video anywhere in the house and I will if I need to send evidence back to Sabine or your work colleagues. So I suggest you trust me and show me what kind of sissy you really are."

I slid my hand in my panties, grasped my cock and began to pull it out. "No, leave it in your panties, girl." I jerked my cock firmly and fast inside the satin and it wasn't even a minute before I felt my orgasm begin to rush forward.

"Into your hand, sissy."

"Oh god," I moaned, masturbating in my sissy lingerie in front of this beautiful woman. My cock erupted and poured cum all over the cupped palm of my hand. I pumped and stroked to get every drop out.

"Now, sissy, I hear you're a cum-gobbler. Swallow that big load of spunk."

I rushed to pull my hands out of my panties and poured the cum into my mouth. I swallowed and licked and swallowed until my hand was clean. My cock softened to about half-erect as being a cum slut before this woman was already re-stimulating me.

She walked up to me and fished out some pink, sparkly object from a pocket of her robe. She yanked my panties down to expose my cock and I felt her putting something on my cock and balls. My stomach sank as I felt what it was and heard the click of a lock.

When she stepped back, I could see she'd put a sissy pink cock restraint on me with a padlock clearly on top. The restraint was in the shape of a small, soft penis. The sides of the plastic were adorned with little sparkly unicorn stickers. The attention and this humiliation were getting me excited but I quickly felt the discomfort of not being able to get erect.

She pulled my panties back up over this and it made a contained bulge in them. "You aren't here to serve your clit, sissy. You're here to serve me."

With that I was led upstairs and to a bedroom that looked like it had been decorated from a sissy fever dream. There was a huge four post bed dressed in satin sheets and bedding. A vanity table had mirror, lights, and lots of makeup. Three dressers were partially open, overflowing with all kinds of lingerie. There was a walk-in closet full of women's clothes and sissy fetish-wear. There was also a chest on a side table.

Mrs. Yakota made quick work of giving me some makeup and fitting me for a blonde short wig. She strapped on a pair of 5" high heels and locked them on me. My cock strained every moment to get hard but being caged just left my body with a diffuse arousal which was very intoxicating.

She walked over to me with a big red rubber ball gag in her hand.

"Sissies should not use their mouths until told to." With that, she eased the ball into my mouth and buckled the leather strap around my head over the wig. "Now kneel by the bed."

I complied, holding my hands together behind my back in a submissive move that felt natural. She walked over to the chest and I couldn't see what she was doing. I really couldn't figure it out until she turned back around.

Her robe was open revealing a red satin corset, red satin panties, garters from the corset to her thigh high stockings. It also revealed a hardness around her groin and a large, extremely realistic looking dildo jutting out from between her legs.

"Sabine let me know you were a bit of a size queen so I thought we'd have some real fun." From my kneeling position, the cock looked huge. I watched as she stroked it just like a guy would. I could see the base of the cock was grinding against her pussy and she was enjoying it immensely. She pulled out lube and began to slather it all over the cock, her fingers teasing it like it was real.

"Grab the posts of the bed and bend over to be fucked, sissy," she growled in excitement. My cock throbbed as well inside its pink prison. I obeyed quickly and ended up face down on the satin bedding, arms stretched wide to grasp the posts and ass jutting out behind me. She calmly proceeded to handcuff me to each post with real metal handcuffs covered in pink fur. My vulnerability increased hundred-fold and so did my excitement.

Feeling her behind me, touching my pantied ass, probing, and then peeling the satin down made me moan in the ball gag.

"Mmmm, yes, sissy wants her Mommy's cock, doesn't she?" cooed Mrs. Yakota. Part of my brain realized how much of this scenario wasn't out of my own head of fantasies but straight out of Mrs. Yakota's. Wanting to please, I played into it, moaning yes.

I felt the tip of her cock sliding up and down the crack of my ass and then she had me spread my legs wider, lowering my ass to just the right height for her. Her fingers took some lube and began to probe my ass. I'd fucked myself with dildos often in my own private play and Mistress Sabine had begun my "cock training" with our first session so I was ready. I wanted that cock so much I relaxed and opened quickly.

"Mmm, Mommy's little girl is such an eager sissy girl, aching for Mommy's big, fat cock." I wiggled my ass to try to seduce the cock to me faster. I felt the head against my hole and even though it felt huge, I stayed relaxed. She gave steady, gentle pressure and my hole had to relax and widen more than I could imagine before the big shaft began to slide into me.

I was stunned at its size. It felt like a log was sliding into my pussy but I'd never felt so filled, so penetrated, so taken before. I was moaning loudly and continuously through the ball gag without thinking.

She grabbed my hips and pushed until her body pressed firmly against my ass. I could swear her cock was up in my stomach by now. I felt her fingernails in the skin of my hips as she drew back almost all the way out and then thrust in faster. She worked me up to it like an expert and before I knew it, she was pounding my ass with that monster hard, fast, and deep.

Each thrust sent a jolt of arousal and pleasure throughout my body. It felt so glorious to be fucked like the total sissy I was, with such a beautiful, huge cock and by a beautiful, powerful woman. Even though I couldn't get erect, I felt like something was happening with my cock and balls.

Mrs. Yakota was working herself up good and fast, moaning and babbling about being Mommy and fucking her sissy girl with her huge cock. Our fantasy worlds ran in a happy parallel as she fucked me and I was gloriously fucked. When she cried out in orgasm, I felt my balls clench in a sort of strangled orgasm and felt cum flow in the pink restraint around my cock. It felt so good to cum from getting royally fucked.

I was sent home with the wig, the heels, and still locked in the pink sissy cage, assured that Mistress Sabine was the only one with the key for the heels and the cage. I was made to walk out to the car and drive away in just my sissy lingerie as my clothes were not returned to me.

Before I left, Mrs. Yakota shared that I had done well and she would report as such to Mistress Sabine. Mistress Sabine would contact me when it was time to see her next. When I dared to express my worries about being locked in high heels and the sissy cage, not knowing when I would be released, Mrs. Yakota told me to just stay sissied up and call in sick until Mistress contacted me.

Driving home on my sore bottom in Mistress Sabine's panties, I felt an inner delight even as I felt terrified about being seen like this. I hoped Mistress would pimp me out again soon.