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Robert, the drill instructor Part 2  

IvannaLaycocks 66T  
67 posts
10/13/2019 11:03 am
Robert, the drill instructor Part 2


Drill Instructor Robert

If you read my previous installment, you will understand without question that Robert ordered me to wear women's clothing when I am not at work daily. I had to get creative. I had a few items of women's clothing and that was all I had at the start of this process. Panties pilfered from an old girlfriend, a worn and ill fitting bra, a skirt and a blouse. I never wore hose or shaved. I was a guy in woman's clothing with 5 o'clock shadow. I took Robert's order seriously.

I was in an odd way determined to take this from a once in a blue moon fetish to possibly being passable in public. A can dream. I was . I was naive. Robert tripped a switch in my brain. Become a sissy, do as ordered and dress like a woman. I was determined to become a woman. I will follow orders. I will do as men tell me without question, to please and satisfy.

I started my shopping at Goodwill and the Salvation Army for bras, panties, skirts, blouses and sweaters. This consumed hours of my time. I shopped the cosmetics area, begging assistance from the clerk at my local pharmacy. My ploy was simple, I had a list from my girlfriend, could you assist me. They gladly obliged. No eyebrows raised at all.

Shoes were proving to be a challenge in my size. I found a pair of women's size wedges a garage . The women them was over 5'" and built solidly. I had a role model. To this , I try and mirror her proportions. Specifically, her contours and<b> curves. </font></b>She was slightly masculine and slightly feminine. She was an odd mixture of both sexes and I was left with the impression that her husband did as he was told. Her name was Ellen, she was from Germany. Ellen met Roger when he was in the military. I would like to have been a fly on the wall in that bedroom for one night. I suspect Roger did it the way told him. I could see Roger as a sissy and her wielding a strapon.

There is an art to applying makeup. It is not something that comes naturally or quickly. Your improves with time and practice and experience. Something as simple as lipstick can transform one's mouth into something clownish in nature to something a man wants to abuse. I prefer the latter. Eyebrows are the same way, they either frame your perfectly or like a facelift gone bad. I took a deep breath. I shaved completely. Smooth as the I was born. One more step to becoming a woman.

I was relaxing sipping on a bold beer and watching the television one evening, maybe a week or two after my outing with Robert. I hear knocks on the door. I went my bathroom window praying it was not a neighbor or a friend randomly stopping by.

It was Robert.

Walking in any type of platform shoe gracefully takes time and practice and balance. It takes ankle strength. I was slowly developing it, though not quite there yet! Wobbling from the bathroom to the kitchen door, I was in heaven. I opened the door, our eyes met and I felt him looking me over with a critical and admiring eye.

"Are you going to invite me in?" he asked. I stumbled and stammered "Yes, Sir do you like? I have been doing as ordered"

I opened and poured him a beer. He sat down on my couch. For some odd reason I remained standing. His eyes were critically looking over every inch of me.

The next words out of his mouth were "you will not sit next to me unless asked. You will be on your knees at all times when I am here. If we watch a movie, your place is on the floor, on your knees and next to me. You will learn your place."
I got on my knees on the floor as ordered and was as close to him as possible. He smelled good. I could see perfectly the outline of his cock in his pants from my vantage point. I could see that he was sem-hard as I sat next to him. The outline of his cock was very well defined. It probably always is, he is hung like a .

He looks in my eyes and said "You look good. I did not say fantastic. You need a new wig. You are wearing the same one that you wore the last time. I like you choice of clothing" My heart san It was a mixed review.

At the end of this, he takes his hand and rubs his cock through his pants. He paused and looked the ceiling and asks, "You really do want be a sissy, don't you? You want be a plaything for men?" My response was immediate and without hesitation. It did not go unnoticed. "I want be sa sissy. I want be your sissy."

He smiled and said "good answer. Have you chosen a girls name yet? Have you?" I had not even given a thought. I had been reading a magazine filled with lovely Russian women and one of them in particular was memorable, Ivana. Ivana, the female version of Ivan. It worked. I liked it. Robert looked at me and said, "Ivana I am going teach you obey a man and you shall enjoy the rewards of obedience."

Robert is not a large or imposing man and only about 5'6". He was in his mid-seventies at the time of our relationship. Rail thin, wiry, graying, slight with pattern baldness. He exudes authority and it is most likely due his years in the military and being in command. He works out and maintains a chiseled body. Robert unzipped his pants.

"Where is your bedroom?" he asks.

I get up off my knees and take his hand leading him up the stairs. Once he is in my bedroom he says "you need do something about your decor. I expect girl's bedding and pillows in here next time. A few stuffed animals on the bed would be a nice touch." All I can do is stare at his bulge and reply, "yes, Sir."

He drops his pants and is wearing a jock strap pair of underwear that barely can contain his coc The bulge is pretty. The bulge is intimidating. The bulge is huge. It is lovely and all I want do is drop my knees and open my mouth.

He walks over me and orders me kiss him. I give him a quick kiss. He grabs me by the back of my head and mutters "fucking tease." He begins force his tongue down my throat. I start to relax and begin to follow his lead. I kiss back and fell his hands go from my head to my skirt being lifted to my ass being rubbed.

I get a one word command "KNEES." I drop to my knees and he let's his cock free. It is a slab of meet. It is thic It is long. It is rock hard. It is bouncing up and down inches from my mouth. I ordered "SUC"

I learned flinch whenever I felt a hand at the back of my head. It was going be lesson time. I was going get schooled or not doing well enough. I felt the hand at the back of my head and my mouth and throat were going be abused. He forced his cock down my throat. I gagged, I could not get the entire length of his cock down my throat. It would take at least another months before I could do it. I still gagged even after months and my nose was buried in his pubes. He still laughed every time I gagged. He would not remove his hand until I licked his balls. He did have a sadistic streak in him.

I was ordered my bed "get on all fours." I feel my skirt being lifted. Robert is rubbing my ass. My undies were being peeled down. I feel a finger poking my pussy. I hear "you have and lube?" I feel cold lube running down my crack and he begins loosen my pussy, one finger, two fingers, fingers and four fingers.

I am ordered back up the edge of the bed. I feel his cock slowly entering. He is gentle. He is taking his time. He is working the head in like a pro and finally once I was able take him, he instinctively knew when slide in the entire shaft. I backed up and my pussy swallowed his coc

He slowly worked his cock in my pussy talking the entire time. "So, you want be my sissy? You want be a little bitch for men? Real men have cocks like mine. Do you want my cock? Do you?"

My response was match his rhythm, bury him deeper in me and reply "Yes, Sir." He started ride me. He started ride me harder. The sound of his ass smacking against my ass cheeks was hypnotic.

I feel his pace quicken. He had a death grip on my hips. I feel every spasm of his cock as he unloaded in me.

He continues pump as he softens. I was bred and happy. I was full of Robert. Robert had claimed me. I would gladly be Robert's slam piece or his dumpster. He then quietly says and kissed " "When I pull , do not let one drop of that come drip ." He pulled back the covers, told to crawl the covers and sleep. "I want my load in you all night long. I want to be dripping of you in the morning when you shower."

He kissed good night and let himself the door. I slept comforted with the knowledge that I was someone's. Someone liked this . Someone wanted this . Robert had claimed me as his own. Robert is responsible for the creampie pic in my profile.

Hellenwr 50T
75 posts
10/13/2019 7:10 pm

I Love it.


jr14009 65M  
19 posts
10/14/2019 1:00 am

Nicely written, luv the ending!


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