My sissy plaything (closed for psyclone86)

I'd been watching him at the office for awhile. What began as just sort of a... sense about him quickly became more and more clear. When I spotted the top of a pink thong on him when he bent over to pick something up, I knew I had him. He was the moldable little bitch I'd been fantasizing about for years. Time to let loose my domme side and make him... or her mine.

I was two ranks above him in the company but I wanted to do it without something that would be workplace harassment. He had to come into this willingly as just two people. Maybe I would just invite him for a drink one Friday. I started to find ways to interact with him more, taking an interest in his projects, helping here and there where my influence could have an impact. He really seemed to appreciate it.

Can't say he also didn't appreciate the chance to be closer to me. I mean he wasn't exactly a macho man being rather slender, almost girlish and about 5'6". I'd always worn a bit of a sensual wardrobe at work in just the slightest ways, but ways he clearly picked up on. For example, I'm a stockings girl, thigh highs since high school. I also prefer the higher heels to ensure that I'm at least eye to eye if not looking down on my male coworkers. Always in skirts or dresses and if my 46D breasts happen to look good in my outfits, I don't think that's my fault.

So, when would I make my move...

I've begun to get more daring by wearing my thongs under my work clothes each day. It has kept me so on edge everyday that I have had to rub one out in the bathroom at least once a day.

It seems my boss has been feeling more daring too. She has noticeably been dressing more provocative and taking more interest in my work as well. It's almost making me wonder if she has found out my secret.

Friday rolls around and I haven't been able to take my eyes off her stocking legs and ass. I can only imagine what type of panties she has on under that tight skirt of hers. At the end of the work day I'm packing up my things to head home for a weekend spent in panties and my own stockings when she walks into my office and asks if I would like to join her for drinks

"Is this for the office?" you ask.

"No, just you and me. Let's leave the office out of it, if that's okay with you. It's just drinks," I play innocently. Already I can sense your submissive nature coming to the fore as you agree and pack up your things.

Your laptop bag tips over so you end up bending over to pick it up. The lines of your obvious bikini panties are clear against your slacks and I just smile.

I lead you to my car without entertaining small talk. You docilely follow and get in the passenger seat. I dare a glance and see you are obviously hard. I smile at you but don't ease the sexual tension.

We end up at a quiet bar near my townhouse. It is only after we enter and sit down that you notice that the clientele is a bit different. There are clearly lesbian and gay couples having drinks or a meal. There is a small dance floor and a three piece playing up tempo jazz.

"I'll have a scotch and he'll have a Cosmo," I order without consulting you. This may be a date but the ground rules are being set early.

I look around the room noticing all the same sex couples having drinks and eating.
while we wait for I drinks my eyes travel up your legs and the rest of you.

"So... umm... do you come here often then?" I ask as the waitress returns the drinks.

I gingerly pick up the cosmo and take a sip

"Only when I'm trying to get into a girls' panties," I smile and down my drink. "Is it working?"

I choke on my drink a I startle.

"But... um... I... ah... I'm not a girl"

I look down into my drink bashfully

Psyclone86 said:

I choke on my drink a I startle.

"But... um... I... ah... I'm not a girl"

I look down into my drink bashfully

Click to expand...

"Well, that's true but you're the next best thing, aren't you?"

I wave the waitress over again. "I'll have another and another cosmo for my girlfriend here." The waitress gives me a wink and grin and goes to fetch the drinks.

"Now is your chance. Stand up and show me your panties and I'll know I was right. Or prove me wrong. Better hurry. Cindy is coming back soon."

I hesitate as I think it through quickly. Do I get up and leave and never think of this again or do I do as I am told?

I blush deep as I reluctantly stand up and slip a finger into the side of my slacks and pull out the side of my lace frilly pink hipster panties.

I look around the bar hoping no one else has seen as I sit back down

"are you happy miss?"

"Delighted, sissy. I think we're going to have sooo much fun together. Here is my address. Be on my doorstep in 60 minutes. Coming to my house means you agree to obey my rules and play my games."

I down my drink when Cindy comes back and leave.

I sit there dumbfounded for a few minutes trying to make up my mind.

I slowly sip my drink trying to figure out if this is all just some joke. As I finish my drink my mind seems made up. I'm going to go home and try and forget about all of this and be more careful with when I wear my panties.

Somehow though, 60 minutes later I find myself standing at your door having just knocked

I open the door wearing a floor length sheer dressing gown over 4" heels, thigh high stockings, a corset with garters, and panties. I give you a big smile and welcome you in.

"We're going to have such fun, honey. Let's see, what should I call you when we play? Something feminine I assume? Would you like to call my Vickie or Mistress?"

I feel my cock start to stiffen as I look you up and down admiringly.

I follow you in obediently.

"well, umm, I, ah, may I call you mistress?" I ask blushing "and please call me anything you wish mistress"

"Mistress it is. Now I'll call you Jenny or Sissy or my little Bitch. You choose. While you're thinking, strip down to your panties so we can get started."

"Yes mistress" I say as I slowly start to pull my clothes off leaving me standing before you in nothing but my lace frilly pink hipster panties.

"Mistress I think I like both Jenny and your little bitch" I stand before you in your entryway with my hands behind my back

"Okay, Jenny when you're a good girl. My little bitch when you're bad," I grin. I lead you upstairs to a gorgeous bedroom. It looks like a teenage girls' fantasies exploded inside it: stuffed animals on a shelf, a pink bed, a chest of drawers overflowing with lingerie and a closet stuffed with hot, slutty outfits. There are high heels strewn about and a large bedside time with sex toys sitting on it.

"Take off your panties, Jenny," I say matter-of-factly. I start to look among the sex toys for something.

My eyes travel around the room taking it all in as I stand there. Slowly I reach down and peel my panties down my legs, stepping out of them to stand before you with my semi hard cock in full view and my hands behind my back.

As I wait patiently like the good little sissy slit I am, my eyes travel up and down your amazing body then along your selection of toys. I bite my lip and shiver in anticipation.