Junior Summer – 1 – Is Summer Great or Maybe Not

Bill had just finished his third year of College, was in a real partying fraternity and had been dating a drop dead gorgeous girl (Marilyn) for two years and who had just graduated. She had been in a Sorority that socialized often with his fraternity. He knew everyone in her Sorority including Marilyn’s cousin (Rosemarie) who was in his classes and who had become his best friend besides Marilyn. The three of them had become inseparable during the past two years.

Good Times and things were going to get better. Bill was going to go home with Marilyn and stay at her house for the Summer. Marilyn’s Mother owned a large Women’s Clothing Fabrication Company and was wealthy. He would work there, make good money, continue dating Marilyn and live high on the hog in a gorgeous house.

Nothing could possibly go wrong unless he screwed it up with Marilyn. Well Guess What? Bill screwed it up big time. Bill had a fetish all of his life which he had carefully kept a deep dark secret. He liked to dress up in Ladies frilly feminine negligees. He had always been discrete and very careful and certainly intended on continuing this way. Marilyn’s Mother, being wealthy, had the prettiest and most expensive Peignoir Sets that he had ever seen. He couldn’t wait for the opportunity to try them on and it quickly presented itself.

Patricia, Marilyn’s Mom, traveled often as the head of the company which left Bill alone with Marilyn. How perfect was that? Marilyn and he could do what they wanted. There love life was fantastic. Marilyn, now that she had graduated, was going to work for her mom and would start in the Accounting division so as to learn from the bottom up. Bill was also assigned to that division which was perfect and he liked being close to Marilyn. Rosemarie was also working in this division as she would also the following year go to work for her Aunt.

Marilyn was working hard to learn everything she could and would often work late while Bill would go home to the estate, swim in the pool and sit at the bar at the pool drinking and waiting for Marilyn. Marilyn had told him she would be late and the opportunity presented itself. He went directly to Patricia’s room when he got home, took off his clothes and started trying on her prettiest Peignoir Sets. He lay on her bed and jerked off into the panties that were part of the set. He was in Heaven Until….


A camera clicking startled him out of his fantasies and he noticed Marilyn snapping picture after picture. He jumped up, snapped the camera from her and ran back to his bedroom. He was naturally trembling, but felt relieved that at least he had the pictures and somehow would talk his way out of this. Marilyn walked by his now locked door and yelled, “I will be waiting in the Den for you”.

It took Bill quite a while to get up the courage, but finally he dressed and went downstairs. Marilyn was sitting there with a stern look, but a smile on her face. Bill then thought that he had a chance to explain, but as he started to speak, Marilyn sternly told him to shut up, listen and not speak if he knew what was good for him.

She then told him she had suspected him of wearing nightgowns and now she had proof. Bill stupidly blurted out that he had the camera, but was quickly shut up when she smiled and said not so. She calmly got up, went to the TV / VCR, put in a tape and he watched everything he had just done including masturbating into the panties and Negligee. Bill was speechless as she told him she had put cameras in her mother’s bedroom while she was gone because she suspected that was were Bill would perform his Cross-Dressing Act.

Bill sat speechless for the longest time as Marilyn just sat smiling and staring at him.

Finally the Ultimatum.

Marilyn said that she had been getting tired of him (to demoralize him more), but she loved the sex. For no other reason than Bill was convenient She had decided that he could stay and keep working for the Summer, but only on her terms. If she was satisfied, then she would not reveal the tape, but would always keep a copy for future control. The alternative – she would supply it for free to the College Book store for all to see. It was her way or the Highway and she would have ultimate power and control.

She was quiet for another 10 minutes as Bill thought of his options knowing there were none.

Take it or Leave it. Bill took it. (What choice did he have?)

Marilyn then said: You are a Cross-Dressing Sissy and Sissies like you deserve to be punished and treated as Sissies. Bill would become her sissy play toy and She would become his completely dominant Mistress.

Bill would be known from this point forward as sissy billy

Bill choked, looked down at the floor and did not say a word. All that Mistress Marilyn said was Good.

Training and obedience was to start immediately as she took his hand and led him to the bathroom. sissy billy was forced to undress and as he stood in the middle of the floor Mistress Marilyn sprayed some foul smelling foam all over her (sissy billy was to be spoken to and referred to in the feminine gender) body. As she stood there she started to jump around and cry as the foam started to get hot and burn her skin. It was a strong depilatory cream for removing hair. Finally she allowed sissy billy to jump into the shower to wash off the foam and as the cream came off and to the surprise and embarrassment of sissy billy, all her hair also came off. Her skin was now smooth and clear of hair like a girl. Just like a sissy girl as she was told by Mistress Marilyn. She was given a feminine smelling lotion to apply which she did trying to sooth the burning. She was then given a lacy thong to put on and tuck in her disgusting male privates and told to put back on the peignoir set which she had just soiled.

sissy billy did it slowly feeling humiliated and just beginning to understand how bad this was going to me.

Rule # 1 and for starters, sissy billy was to wear only feminine clothing as picked by Mistress Marilyn when she was in the house. sissy billy started to whine and then asked if she could wear boy’s clothing when Mistress Marilyn’s Mother was home. Mistress Marilyn just smiled and said: “Not necessary sissy billy, I have already called mother and told her and Mother understood and backed me 100%”. Sissy billy was mortified that already someone else knew and she blushed, but shut up.

Mistress Marilyn then took sissy billy’s hand, led her down the stairs and then told her to go into the living room again. She obeyed and walked three steps into the living room and came to an abrupt stop. There sitting on the couch and smiling was Mistress Marilyn’s two sisters, Jacqueline and Jane. Then she saw her best friend and Mistress Marilyn’s cousin sitting in the chair. It was Rosemarie. She quickly tried to back out of the room, but Mistress Marilyn forced her in and told her to stand in the middle of the room in her pretty feminine frilly Peignoir Set. She was absolutely humiliated.

sissy billy turned to Mistress Marilyn and told her she did not want to do this anymore and that she was leaving and she couldn’t stop her.

Mistress Marilyn glared and shouted: “YOUR CHOICE. I can forward the video now if you want”. It was a phrase sissy billy would hear many times in the future when she protested. sissy billy stood still looking at the floor and was very quiet as the Ladies giggled at her discomfit. The amount of people that now knew had just more than doubled.


Mistress Marilyn then said: “Ladies, our cross-dressing sissy’s punishment needs to be started to instill instant obedience and I think a good sorority spanking is in order” The other ladies clapped and giggled as I blushed. Mistress Rosemarie felt a little sorry for sissy billy as sissy billy had no idea of how bad a sorority punishment spanking could be. Mistress Rosemarie, as had Mistress Marilyn, had pledged their sorority as freshman and had on several occasions been punished in this manner. Mistress Rosemarie remembered how she had cried and that she could not sit down for a day. Mistress Marilyn brought out her very large Sorority Paddle and also an ankle restraint with spreading bar and wrist restraints attached. She explained to sissy billy that this was a sorority punishment administered for misbehavior’s and sorority girls took their punishments like ladies. She hoped that I would. sissy billy would have the ankle restraints and bar attached and then bent over with her wrists attached. She would be given 5 spankings by each lady, but if she fell over, the spankings would start from the beginning. She would also have to wear 3” heels (the 5” heels would be much too difficult for her start with).


sissy billy was bent over and her hands attached to the restraints between her legs. Her Peignoir was pulled up and over her head exposing her bottom with the thong pulled tightly up her crack. She almost fell over then. The paddle was laid on her back for each Lady to use in turn. The spankings started and she fell over on the third whack. They started again and sissy billy got to 8 whacks this time. After an hour of spanking sissy billy had not got to 12 strokes of the paddle. The Ladies decided to rest and the restraints were removed and wrist and ankle cuffs were put on.
The 5” heels were put on and sissy billy was put in the corner to stare at the wall. She was assured that she would have to repeat the punishment until she could do as well as a freshman sorority pledge. She was told no girl had ever failed so miserably. sissy billy stood in the corner for hours as the Ladies talked. Her ass must have hurt terribly as she wriggled in pain trying to stand still as directed. She heard the Ladies say goodbye and heard them leave the room. sissy billy had absolutely no idea what was happening, only that her life had changed drastically in the last few hours.


Mistress Marilyn brought her back to the center of the room and then stared at her for several more minutes.

She then said: “We have decided that you need intensive training and the four of us will assist in you obedience Training. You are to refer to each of us as Mistress and obey without question. Every third day we will pass you to the next Mistress, but we will vary, not be consistent and you will accept this without question. Each work day you will still go to my mother’s factory to work and perform a full day’s work at whatever you are assigned, which will also vary. My mother and I will instruct you in all aspects of sissy training and punishment, one of the ladies will handle severe punishments as necessary and dictated by you performance, another Lady will instruct you in sissy service and the fourth lady will instruct you in social training and interacting with others in a social setting which I am sure will be humiliating. The Ladies are in the other room deciding how and who will perform what training. You are to stand still and erect until someone knocks on the door and then you will follow their orders without question. Training starts Now”.

sissy billy looked at Mistress Marilyn, about to protest and before she could speak Mistress Marilyn shouted again: “YOUR CHOICE”

She stood in the middle of the room for an hour. sissy billy hoped the first Mistress would be Mistress Rosemarie because she had been her best friend and she hoped Mistress Rosemarie would be the most lenient.

Knock – Knock – Knock and sissy billy approached the door with trepidation and fear not knowing what was next for her.


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Great story! Would love to be the sissy receiving the training!

Love the story! Would love to be the sissy receiving the training!

Sure in fantasy it sounds great,, however not having the pictures shown requires obedience.. I know. I am now the property (#737-820-633) of a Domonant Mistress who holds my future.. My choice was to tribute.

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