First Date with Mistress

It starts with this girl that I have been flirting with for the past few days and find myself on a first date. I arrive at the young ladies apartment and knock on the door. I am surprised to see her dressed to show off her amazing body. She is slinky dress with a plunging neckline, doing a very nice job of drawing my eye to her cleavage. I continue looking down to see her lovely tan legs sliding out from under a shockingly short skirt. She invites me in and struts towards the center of the room.

I am trying not to stare as she walks away. Then she quickly turns to find me awkwardly staring at her body. She smiles but I know that I was caught.

I quickly try to start small talk but I am nervous and it is obvious. She seems to take joy in this. She then walks up to me smiles and give me a big hug, making sure the hug last just a moment too long, and pressing her chest firmly against me.

She then bites my ear and whispers that she has a plan for tonight, but she has to know that I will play along. I am very curious and try to ask what the plan is. She explains that all I need to know is that she is in charge and that she will make sure that it is a memorable night. I was instantly nervous with the way she accented the words "charge" and "memorable".

I took a deep breath wondering just what I maybe getting myself into, but knew that there was no way that I could not go along with the plan. I nervously agree to go along with her plan for the night.

She smiles, then quickly tells me to remove my clothes. I am nervous, but slowly begin removing my shirt, shoes, then pants. She is pacing and closely watching me. Once I am completely naked she slowly walks around me as if taking inventory of my body. She then stands behind me slowly drawing her nails across my chest. She starts measuring my body with a tape and entering the measurements into a recorder. Height 61, waist 34, penis length 2 inches.

It gets bigger I stammer.

Thats OK she says, I just need to find a small enough tube. She proceeds to put on a pair of rubber gloves and instructs me to bend over and grab my ankles. She probes my backside and again into the recorder needs small probe at first. By now I have a raging hard on and she notices. More measurement 5 inches fully engorged. She then proceeds to stroke me a few times while mounting me from behind and I shoot in about 10 seconds. She starts laughing, not only 5 inches but also a pre-mature ejaculator.

Then whispers that it is time for me to get ready. She tells me to go trim all body hair, shower, and wait for her.

When I am done she calls me out, still nude and tells me that what she has planned for me to wear is in the other room. She then opens the door and explains that she will be back to check on me.

I see a bag setting on the bed, just a plain brown bag. I dump the contents out and am instantly surprised. There are shiny red high heals with ankle straps, a thick leather collar, a plain white tank top, and a short denim skirt. Also a chastity belt that appears to be a MySteel. That is all. My mind is running all over the place, what does she have in mind.

I put on the collar, then the belt, the tank top and skirt. I set down on the bed and begin putting on the shoes. No sooner that my foot is in these I realize that walking will be difficult if not impossible. I will be standing on my tiptoes.

I then stand in front of the mirror and am truly surprised to see myself in this situation. This is not how I had ever pictured myself.

The door quickly opens as she returns she sits on the bed and slowly crosses her legs making it a point for me to notice. Then asks me if I like my new outfit. I stutter nervously hoping to find words. She leans back on her arms, reclining on the bed. Then says, "The correct answer is Yes Mistress. I love what you have done with me." I then repeat. "yes mistress. I love what you have done with me." She replies "good boy".

She proceeds to put a lock on my chastity belt. She explains that since I am having such a hard time moving around in my shoes, I should kneel down and walk around on my knees. I oblige happy to get off my feet.

I then scoot towards her on my knees. She reaches out pressing the heel of her shoe against my shoulder. Then tells me to kiss her shoe like a good little slave. I begin kissing her shoe and continue for a few minutes. She then uncrosses and crosses her leg giving me the other shoe. I get a clear view of her sheer black panties the slow ways she did this. I continue kissing the other shoe.

Quickly she stands up and walks over the corner of the room. Slowly bends down to a bottom drawer getting a rope. Soon I realize that it is actually a leash as it is clipped to my collar. She begins walking out of the room, then with 2 soft tugs on the leash, I realize that I am to follow her.

I look for my clothes we go back into this room, but they are gone. She walks me around the room twice with me following close behind. Then she stops me in front of the couch then stands me up, then runs her hand up my leg. Then roughly grabs my belt and slides a finger under it. Then says good boy, still quite interested I see. Of course I am still trying to get hard in the belt.

Next, she gets a short rope and quickly ties my hands securely behind my back. She then tells me to turn the television on as she sits down, but makes sure to tell me not to use the remote. The cable box is just a few inches off the ground, so I have to walk over kneed down and press the button with my nose. I then change the channels until she finds something that interests her or maybe she just tires of my charade.

She now tells me that I can take off her panties. I am still teetering on my heels with my hands behind my back, but I will try. I kneel down and walk on my knees over to her seat. She stands up and smiles down at me as I nudge my head under her dress and press my face against her panties. I can see through the sheer fabric that she is shaven. Tugging at each side I finally work them down her legs. She makes it a point not to help. She sits back down and closes her legs, explaining that I must beg to see her pussy.

I start asking if my mistress would let me help her cum, explaining how anxious I am to learn how sweet her beautiful pussy will taste.

As she leans back putting each leg over the arms of the chair, I quickly lean in to kiss her. While slowly licking and happily realize that she is, wet, very wet. I loved knowing how much she was enjoying toying with me.

I begin to hear her softly moan faster. I feel her wiggle and shrill a couple of times, but I keep going. Finally she pulls my face away from her pussy and smiles as she wipes her juices from my face. She tells me that she is very happy we have become friends.

She unties me. Shows me to my clothes. What about the belt, can I have the key? While slowly rubbing my belt she explains how she wants me, but refuses to have sex on the first date. She couldn't have me thinking that she was easy.

I cannot believe how my first date with this young lady has literally lasted less than 2 hours, but somehow been one of the most eye opening experiences that I have had.

[ Back to chastity fiction page ]

Page last updated 2009-Sep-12 by: Altairboy@aol.com