Robert Bernard was alone in his flat one day, his wife not being due home from work for a couple of hours, and he happened to notice a pair of his wifes stockings lying over the edge of her open panty drawer. He felt an urge to try them on.
It was unfortunate that he should have been tempted on that occasion for he was to be discovered half an hour later dressed in a garter-belt and stockings, as well as a pair of panties, when his wife came home earlier than expected. And this was to have far-reaching consequences for him.
Let us first picture the scene.
Robert, as soon as he got the idea of putting on the stockings, quickly realized that a garter-belt would be necessary to keep them up. He went to the drawer where his wife kept such things and rummaging among a plethora of panties, bras, and garter-belts found one that looked suitable.
He undressed and fastened the garter-belt round his waist and then sat on the bed to pull on the stockings. He felt an unusual kind of excitement as he fastened the stockings and almost at once he became erect. It was then that he remembered the panties 1n the drawer and he went back and selected a pair, pulling them up his legs, hiding his erection. He stood in front of the dressing-table mirror
and thought that apart from the bulge in his panties, the lower part of his body looked appealingly feminine.
He began to finger his prick and was about to masturbate when his wife came into the bedroom.
He swung round, covered with confusion and embarrassment, making a pathetic effort to hide the underwear he was wearing by reaching for his pants, but his wife had seen everything.
“No need to hide them,” she said calmly.
He was very surprised to hear her speak so calmly, expecting an outburst of ridicule and contempt from her at what she had seen. He dropped the pants and stood before her and began to undo the garter-belt.
“You can Keep them on,” she said. “No need to take them off. Tell me, why did you put them one” Her matter-of-fact manner surprised him, but he regained some of his composure and tried to think of a reason for having put on her stockings. Now that he was faced with trying to explain his action, he found it difficult.
“I, er, well, I just liked the idea of putting on a pair of your stockings. I don’t quite know why. And of course, I had to put on a garter-belt to keep then up. …”
Vera had never thought of her husband as a sissy but she had suspected a small streak of femininity in his psychological makeup, a characteristic
which in one way she despised but which she now knew she could turn to her own ad vantage. She wanted a man in her life to do what she wanted him to do, but she had never really dared to bully Robert. For one thing, he had married her a little reluctantly in the first place because he suspected she wanted him for his money. If she had taken too many liberties, he would probably have divorced her.
Now the situation had changed. She had caught him, so to speak, in flagrante delicto — in the very act. Not the very act of sex, or adultery, but that of putting on women’s undies! She knew that most men looked with loathing on transvestites, and especially the kind of men that Robert numbered among his friends. She now had him in her power and could easily threaten him with exposure. But more than that, the fact that he had put on her stockings and panties gave her a clue to a side of his character she could easily exploit. She could even insist that he wear women’s clothes.
“Well,” she said after a moment’s reflection, “you’d better do it properly. Put on a bra and a slip as well. You can borrow some of my things, then you’d really look like a woman.”
He felt grateful to her for taking it so understandingly and asked her if she really meant he could put on one of her bras and slips.
“Of course,” she said.
“And you don’t think any worse of me?” he asked her.
“No,” she said, “I’m not like all those friends of yours and the people on the board of your firm who would laugh at such a thing and be shocked by it. No, I’m not like that. I can understand why some men want to dress as women.”
He saw what she meant about his friends and fellow members of the board. He didn’t really want her to get the idea that he really wanted to dress as a woman. That would be dangerous.
“Oh, it was only a joke,” he laughed. “I don’t really want to dress as a woman.”
“I don’t think your friends would see it as a joke if they found out about you,” she said. “They’d ostracize you.”
“Well, you won’t say anything to anyone, will your” he asked in a voice that betrayed his fear for the first time.
“No, I won’t say anything, provided …,” she stopped mid-sentence.
“Provided what?” he asked her, now beginning to be alarmed.
“Well, provided you do as I tell you,” she said.
“Well, of course I’ll do as you tell me,” he said with relief, “I mean if you don’t tell me to do anything …. anything ….”
“I said provided you do as I tell you. I mean in every sense — not Just in this matter.”
“I don’t understand,” he said.
“Listen then. If you want me to go round telling everyone you’re a sissy, I will. If you want me to keep it to ourselves you’ll have to go along with me. You can’t have it both ways. You want to dress as a woman and I don’t mind. But there may be things I want to do. Now do you understand?”
He was baffled, not quite realizing where things were taking him. But he could see that he was in something of a dilemma. If he didn’t give her an undertaking to do as she told him, she might start talking.
“All right,” he said, “whatever you say.”
“To start with,” she said, “I don’t really want you to wear my best things. You’ll have to acquire your own. For the moment I’ll give you some from the clothes I don’t want.”
If that was the only condition she was making, he thought, then there was no need to worry. He smiled as she went to the dressing-table and began sifting out a few items of underwear. “I’m afraid the stocking situation is a bit grim. You’ll just have to wear these knee-length hose for the moment. I can’t spare expensive French nylons for dressing up in. Ah, here’s a pair of white panties you can have. Put those on for a start.”
He took off the elegant things he had had on when she returned and put on the flimsy cast-off panties and the rather uninspiring knee-length hose.
Looking at himself in the mirror he was disappointed
at the sight he presented, determining there and then to buy himself some expensive lingerie at the first opportunity.
“And here’s a pair of long gloves. Try them on,” she suggested.
He put on the gloves and waited for her to find some other things.
But she had only been playing for time. She came in and found him in her stockings. She really wanted to see him humiliated and degraded and now she had thought of a way of doing it. Before that evening she would never have dared do such a thing as she now contemplated, but she had been emboldened by the hold she now had over him. With each minute she felt a growing excitement at the way things had turned out for her and the enormous pleasure she was going to have 1n future demeaning him, degrading him, and reducing him to helplessness. He had used his money to keep her powerless: now the tables were turned.
She picked up the velvet tie and walked over to him. “Turn round,” she said.
He turned to face the other way and she asked him to put his hands behind him. When he did so she skillfully wound the thick tie round his wrists and then with a quickness that took him by surprise she Knotted it as tightly as she could.
“What are you doing?” he gasped.
“What am I doing?” she repeated, menace in her voice noticeable for the first time, “What am I doing? I’m tying you up. I have tied you up, that’s what.”
It wasn’t funny any longer for Robert and he turned round angrily to face his wife. “Untie me,” he said sharply.
“This has gone past a joke. I’m not going to tolerate this sort of thing.”
“Well, if you insist on being untied, I’ll have to untie you. But then we’ll spread the news about your hidden girishness,” laughed his wife. “You’d prefer that, wouldn’t you?”
He was trapped and he knew it. She had him just where she wanted him. She was obviously quite serious and for some reason wanted to take advantage of her discovery.
“What do you really want?” he asked her.
“Can’t you guess?” she asked him. “I want my revenge on you, and I’m going to take it. I’m going to humiliate you just as much as I like, inflict punishment on you if I want to, and debase you. That’s if you insist on being difficult. But if you want to have a peaceful life and dress as a woman, I’m willing to support that so long as I get what I want out of it. I want you to please me in any way I desire, and to deny yourself any physical pleasure from my body. You should be content that I am allowing you to dress as a woman. In fact, I insist that from now on you should dress as a woman, not only dress as one, but be one.”
He stood there amazed but now ready to listen to what she sald.
“First, I am going to cut your hair very short so that you can wear one of my wigs. Then we will shave your armpits and the hair off your chest, as well as your pubic hair, and the hair on your legs. You will then lather your body, soften your skin with oil, then powder yourself all over, and before you dress I shall make you up in such a way that you will really look quite feminine. After that, your clothes. I’ll relent on what I said about making you wear my cast-offs: you can have my best undies and dresses.
“Each day you will massage your breasts to help them to grow and I shall purchase hormone tablets that will escalate that process. One of these days I might decide that it would be better if you had a sex-change operation, but that will depend a lot on how you behave. Nevertheless, some sort of restriction on your sexual apparatus would seem desirable if you are really going to think of yourself as a woman. I think I could fit two rings on your penis that would prevent it swelling or becoming erect. And to get into the psychology of being a woman you will wear sanitary napkins each month. It might be a good idea if you wore the ones I would normally throw 1n the trash. Of course you will never stand up to urinate but always sit down on the toilet, just as a woman does. That’s just a beginning.”
He knew that he had no longer any choice and felt that he had better make the best of it. Perhaps it wouldn’t be so bad dressing, thinking, and living like a woman. Was it possible that he had always subconsciously wanted that? But what was his wife really getting out of it? Just the humiliation he would suffer?
No. She was soon to add further conditions for keeping his secret.
“Being an entitled male – playing a woman will humiliate you but you might eventually get used to it. Therefore, I shall degrade you further for my own pleasure by stimulating your male sexuality and then immediately denying any relief or satisfactory outcome. I want to punish you for the times you have taken my body for granted and then when you’d used me, the way you cast me to one side. Now it’s my turn. And that’s why I have tied your hands.”
With those ominous words she went up to him and began to manipulate his clitty. Despite the humiliation he felt at all she had said he soon found himself hardening, even though he tried to retard it. In the end she worked him back and forth with such skill that he was bone hard.
“Now,” she said, “here is the technique I intend to adopt to destroy your faith in your maleness.” She immediately began to slap his erect dinky with her hand, continuing to do so until he was small again. It was both painful and humiliating for him and he began to realize how deeply she had resented his male chauvinism
in the past.
But that was only a beginning for she then went on to rouse him again, delicately caressing the flaccid clitty until it jutted aggressively again. Then she repeated the slapping until once again he flagged and shrank.
“This is just a beginning,” she then told him. “I have numerous ways of conditioning you to give up your maleness. But you will learn about those later. Meanwhile I shall release you and you will start at once to live according to the routine I have outlined. Do not forget that I can at any time expose you for what you are and ruin your friendships and your career!”
And then, as a parting shot as she prepared to leave him to think over the evening’s developments, she added: “And from now on you will call yourself Roberta.”
The End
Discussion?
Sometimes sissy rubyjo dreams about this possibility of being in h.er feminine clothes and coming out so that s.he could serve the Mistress and be a sissy transformed and not just be in transition. One day sissy rubyjo will hopefully have h.er transition completed.
curtsy ,
sissy rubyjo
My life as a sissy began at a very young age. my mom and aunts knew because I was caught in panties and heels I was about 8 years old. They did not discipline me . My aunt and mom were sweet they actually helped me to feel more girly. At the age of 10 I had a full wardrobe of girl clothing that I could choose from it was not just frilly panties. Garter belts and fine hose I could wear makeup red lipstick and they kept me under thier control at all times .
A beautiful story.