A Week End with Mistress Pt. 02

Story Info
Sissy gets ready for Mistress' evening out.
2.1k words
4.4
19.4k
5

Part 2 of the 4 part series

Updated 06/09/2023
Created 10/12/2018
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

Dear readers this is my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive.

This story is based in part on facts and part on fiction. I will leave it to the reader to decide which is which.

*****

I arrive at Mistress Nikki''s a couple of minutes before 2:00 and grabbing my bag of clothes and the lunch I had picked up from Jeanie's Deli run up to Mistress' door. Getting on my knees I ring the door bell and wait for Mistress to answer. After waiting a few minutes the door opens and I am greeted by a Mistress standing there in high heels and a long black silk dressing gown.

"Crawl in sissy and great me properly."

I crawl in and start kissing the tops of Mistress' shoes.

"OK, sissy, you may stand up and take off your shirt and pants and hang them in the hall closet. Inside you will find an apron and slippers for you to wear. When you are done bring the lunch and meet me in the kitchen."

"Yes Mistress," I reply.

Getting to my feet, Mistress sees my face for the first time. She quickly slaps me across the face and says, "What is the meaning of arriving with your lipstick a mess and smelling like an unwashed cunt?"

"I am sorry Mistress, but when I had finished paying Jeanie for lunch there was not time to clean-up and be here on time."

"Well sissy, we will have to figure out some way for you to pay for this. Now get changed and into the kitchen."

Quickly remove my shoes, slacks and shirt and hang them neatly in the closet. The apron was a sheer pink with plenty of ruffles around the edges and the slippers were also pink with modest heels. I get these on and grabbing the lunch hurry into the kitchen.

Mistress is seated at the table with her computer doing some work. There were two bowls on the counter. Mistress looked up from her work and said, "Split the salad into the two bowls and give the dressing to me. Get us some forks, napkins and ice water to drink."

I set about my tasks and shortly had the lunch set-up at the other end of the table and I stand back waiting for Mistress. Shortly she finished what she was working on and moves to where the salads were waiting. She picked up one of the bowls and set it on the floor. Opening her dressing gown Mistress squats over the bowl and the floor and pees on the salad saying, "I hope you like your dressing, sissy."

"I am sure I will love it," I replied.

Taking one of the napkins Mistress wiped her beautiful pussy clean and sat the bowl and napkin on the table and indicated for me to take the chair before them. Mistress sat at the other place, putting the dressing from Jeanie's on her salad she started to eat. Looking at me she said, "You better start sissy, I expected it to be all gone by the time I am done."

As we eat Mistress tells me a little about her plans. "We will be going out to a club for dinner and some fun this evening. We will get dressed before we go and there are a few rules for you to remember.

• As usual you will not question any of my decisions.

• You will not speak unless given permission to respond.

• I will order our food and drinks and you will eat what I decide you should.

• You will walk behind me and to the left at all time unless something blocks your path.

• You will keep your hands on the table at all times.

Do you have any questions?"

"No Mistress and thank you for the wonderful salad dressing."

"Thank you sissy, clean up the lunch dishes and then come kneel beside me."

I get up and start cleaning up from lunch, washing the dishes and putting everything away. When I am finished I kneel beside Mistress while she works on answering emails and whatever else she is doing. Mistress completely ignores me for quite some time before she turns to me and says, "Sissy all of this work and thinking about tonight is turning me on. I think we better put that talented tongue of yours to work. Go get the service mat and get under this table and get to work, start slowly."

The service mat is about 4 feet by 5 feet and three inches thick with a plastic covering covered by cloth. I get the mat and a blanket and place these under the table and then crawl under the table. From experience I know what Mistress Nikki wants and carefully remove her high heels and stand these out of the way. Mistress loves to have her feet worshipped and massaged and I get to work. I pick up Mistress' right foot and start to massage the instep while at the same time taking her large toe into my mouth. I slowly kiss, suck and lick the toe and the area between it and the next toe. Over the next 20 minutes or so I make oral love to the toes on her right foot. Then I move to the left foot and repeat the process. I can tell from the way Mistress' breathing has changed my ministrations are having the affect she desired.

As I finish with the left foot, Mistress opens her robe and parts her thighs, indicating she wishes me to continue. Complying with her wish I start to slowly kiss and worship each of her beautiful legs, a little way on one leg and then switching to the other until I have reached that beautiful soft inner thing just below her wonderful womanhood. As I am gently kissing her inner thighs the phone rings and Mistress answers, "Hello this is Nikki."

"Oh, hi Jeanie, let me take care that sissy here can't hear what we are talking about", Mistress says to the caller.

Turning her attention to me Mistress says, "Sissy start kissing and licking my pussy, now. Do it slowly and lightly, I do not want to cum until I tell you I am ready"

I reply, "Yes Mistress." I then move to start lightly kissing and licking her wonderfully smelling, beautiful and wet pussy. As I do this Mistress clamps her thighs against my ears blocking out all sound. I don't know how long I kiss and lick her pussy lips and insert my tongue in her wetness without touching her clitoris. I am busy and with her thighs pressed against my ears I have no idea what Mistress and Jeanie are cooking up.

After some time Mistress relaxes her thighs and says, "OK, nora I am ready, you may finish your task."

I now start to give Mistress' clitoris the attention it deserves and desires. When Mistress is aroused as she is now, her clitoris swells to about 3/8" in diameter and ¾" long, her own little dick. I kiss it, lick it and finally suck it into my mouth and lightly flick the tip with my tongue. At the same time I gently and slowly insert two fingers into her pussy and rub her g-spot. I continue to make love to her pussy with my fingers and tongue and Mistress becomes more and more aroused.

A short time later Mistress gasps and then explodes into a wonderful orgasm grabbing my head and forcing it into her pussy as she comes, drenching my face in her wonderful female juices. As Mistress recovers she relaxes her grip on my head and says, "Sissy you are such a wonderful pussy eater, I wonder if you will do as well with cocks? I am going upstairs now and you need to clean up down here and then join me."

Mistress gets up and heads upstairs and I start to clean-up putting the mat away and the blanket that is wet in the laundry. After straightening up Mistress' items on the table I go upstairs to see what Mistress needs next.

I find Mistress in a bubble bath and she says, "Get naked sissy and help me bath."

I quickly remove my clothing and kneel beside the tube. Mistress hands me a razor and instructs me to shave her lags and underarms. When this task is done she gives me her wash cloth and I start to carefully and gently wash her beautiful body; the smooth white back, strong arms, flat stomach and long legs. She then stands and turns her back to me for me to wash her sexy round butt. When I have finished washing and rinsing her beautiful bottom she says, "You may now worship my ass, sissy."

I start gently kissing each globe of her ass and work my way to the hidden surprise in the lovely valley of here bottom. I slowly and gently spread the two globes revealing the target of my worship. I start by kissing and then licking her puckered ass, before probing it with my tongue. As my tongue probes her anus, Mistress pushes back trying to get me in deeper. As I probe Mistress pushes back as if I am fucking her puckered hole with my tongue. After a few minutes Mistress pulls away and say, "Sissy that is wonderful, but if we are going to make our reservation we have to stop and get ready. Go get a shower and douche making sure that pussy yours is clean. Then report back here to me and bring a pair of your white stockings with you."

Off I go to do as instructed. After using four bottle so douche on my pussy, showering and applying fragrant lotion I return to Mistress' room.

As I enter the room I am stunned as Mistress is dress as any sissy could only dream of in their wildest fantasy. On her legs she has black leather over-the-knee spiked heeled boots and black hose. She has a black calf skin mid-thigh skirt with a black see-through nylon blouse. Under the blouse she has a thin transparent bra through which her dark areoles and nipples are visible. I can only imagine what she has on under the skirt.

As I drop to my knees I think this is going to be a fun night. I quickly crawl to Mistress and start to kiss her boots. After a few minutes Mistress says. "Stand up sissy and put on the white stockings and this pink garter belt." I follow her instructions and notice that although the garter belt appears normal there is a small pocket on the outside of the belt. She then takes me to her bed and has me lay on my back. First she glues some false c-cup silicone breasts on to my chest and has me hold them while the glue sets. While I am doing that she inserts a plug into my anus. Although I cannot see the plug it has two cords attached to it. The first is a loop that Mistress loops around my balls. The other cord is plugged into a small box that is secured in the pocket on the garter belt.

Mistress then has me stand up and she gives me a sheer pink bra and a pair of sheer pink panties with ruffles on the seat to put on. Mistress then sets me down at her make-up table facing away from the mirror and does my make-up and stylizes my hair as femininely as possible. As she finishes she adds a very sexy perfume. When she turns me around I am shocked by how feminine my face looks, if I had a wig on I would have sworn I was a women, but with my hair I am just a male made up to be a sissy.

Mistress, "We need to finish getting your dressed so we can leave and not be late." With this she hands me a pair of white stretch fabric pants to put on. When I get them on several things are obvious. First the pants are short about six inches above my ankles so the stockings are obvious. The pants are so tight my chastity cage in the front and the ruffles covering my ass are visible. To this she adds a sheer hot pink blouse, hot pink high heeled sandals and a matching purse. She says "We need to go. I will drive, but your billfold is in the purse."

With me following as a good sissy we go down to the garage and get in the car and leave for dinner. I am wondering where we are going with me dressed like this?

To be continued

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
Claudia69Claudia69over 4 years ago
Good Chapter 2

Looking foreward to the next chapter....

dacoach44dacoach44over 5 years ago
Bitch getting ready...

Lucky faggot; she femmed you up so well.. You are such a nice obedient slut.

Share this Story

Similar Stories

Social Media Star Boy becomes an unwilling lingerie model for online viewers.in Transgender & Crossdressers
Jimmy's Dilemma Tough choices for a soon to be cocksucker...in NonConsent/Reluctance
Sissy Sidney and Sister He joins a pajama party as an honorary girl.in Transgender & Crossdressers
Grieving Boy and his Step Mother A submissive young man humiliates himself for his stepmother.in Fetish
"Sissified": 12 Days of Sissy-mas Straight man is turned into a submissive sissy by...in Transgender & Crossdressers
More Stories