Mistress Psyche's Feminization Fantasies


Sissy Girl Stories



By a Happy Wife

He wore an 8 in a woman’s shoe. Very few men know their size in a woman’s shoe but he did. To make matters worse his wife knew, his mother in law knew, his sister in law knew his mother and his sister all knew.

The day he learned his woman’s shoe size is a day he shan’t forget. One day in his life that changed so much. The simple act of having his foot measured, just a bit of fun for the ladies, just a joke really, the next thing you know your life is completely different.

His mother, mother in law, sister in law and wife were playing cards one sunny Sunday afternoon. His sister would join them later but for now he was pressed into service as the forth hand. There was more girl talk than card play and he was often brought into the conversation, for a “man’s perspective”. The ladies talked about clothes, shoes, hair and makeup. They also talked about who wore what, how they looked and how the various men in their lives reacted to it. He had been in these conversations many times and knew from the way the ladies talked to him he was considered just a bit less than the men they chatted about. He was often referred to as the extra girl.

He usually served them their tea and made the little sandwiches they dined on. Today was no exception and he wore the dainty tea apron his mother in law had given him on his birthday. “I know you hate the apron.” His wife said, “But mummy loves to see you in it.” “ And I love you for being man enough to be a little feminine.” He was afraid the apron made him a little more than a little feminine in appearance.

His sister didn’t bother with the doorbell, the card players all heard her cheerful “I’m here girls” shouted from the hallway. He blushed as she kissed his cheek girl style and asked, “How are you gals today?” He noticed his mother in law smile at the girl and gal reference that included him. His sister was carrying three shoeboxes from one of the more up scale stores in town. “Missy’s is having the best sale ever, I bought the cutest shoes.” She said. His wife wanted to have a look right now and his sister wanted to show off her new shoes. Soon the women were voicing their approval and were looking at the shoes as only a woman can look at a shoe. When it happened. His sister said to everyone, “Jimmy and I wore the same size shoe for years.” His wife smiled and said, “and did he wear yours?” Never breaking stride his sister said, “Oh yes I used to make him dress up for me all the time. Mommy and I thought for a while I would wind up with a little sister instead of a little brother.” The women looked at him and his mother in law said, “Jimmy why don’t you try on a pair?” Then they all were urging him to “try on a pair”. His sister said “there are some knee highs in one of the shoe boxes, go on Jimmy you always liked to wear my clothes.” Both his wife and mother in law were looking at him as though they were both cats and he was a trapped mouse. His sister was holding a pair of chunky heeled loafers out to him. He managed to say, “I am sure my feet have grown sis.” His wife said, “Try anyway”. He slipped of his own shoes as his sister gave him the stockings. “I know you know how to put them on” and he knew it too. With one stocking on His sister in law said “His feet are so pretty.” “Look at how tiny his feet are, with a coat of polish on his toes he could wear open toes.” The women had moved in to take a look at these pretty feet. His sister said, “I know he will look smart in some nice pumps.” His mother in law said, “his feet are really petite.”

Then his wife said, “I just wish I had paid more attention to how small his feet were before we were married.” His mother in law nodded and said “oh dear is he small in that area too?” His mother didn’t help things by saying “he was always little down there” “I always felt sorry for him and thought it was probably best that he was girlish.” “Shit” he thought what the hell are these women trying to do to him. He knew he was OK in “that area” he got no complaints from his wife Cathy. His sister had slipped the loafers on his feet and had him standing. She rolled up his pant legs a couple of turns and the women were gushing about how nice he looked in “those shoes”. “See 81/2 just like your sister and me” his mother said. Before the afternoon was over he had modeled all three pairs of shoes and was unceremoniously dismissed by his wife with the instructions to “pick a nice color and do those toes, Miss pretty foot!”

The gals finished their card game while he sat dejectedly in the corner and gave himself his first pedicure. His wife instructed him to go upstairs and fetch her red canvas sandals, “they are a nine but they tie at the ankle and should fit you alright.” Before he could protest his ever-cheerful sister was dragging him up to the Mistresses shoe closet for his next humiliation. The sandals were in the words of the women “absolutely adorable”. He never thought he would hear his shoes described as adorable. They were red canvass; a wide band went across the vamp of his foot. There were two straps that wrapped around his ankle and tied in the back with a bow. The shoes had a jute covered high wedge sole. Because the shoes and his feet were “so pretty” his sister thought he should be wearing a skirt or Capri’s. She yelled down to his wife who answered back with a disinterested “whatever”.

An embarrassed young husband descended the stairway to the applause of the assembled ladies. His red print skirt swirled prettily as he walked. His wife and mother in law stood a little bit off to one side and didn’t seem to be enjoying the scene as much as the other girls. He finished the day still in the skirt. When the girls left he was hugged and air kissed just like all the “other girls”, he fixed a light supper for his wife and himself, they watched a little television and went up to bed early. He was still in the skirt and sandals when his wife said; “I have never been so embarrassed in my life.” “I thought I was marrying a man, but look at you traipsing around in a skirt and sandals, with your toenails painted yet!” “And now I find out you have been playing dress up with your mother and sister for your whole childhood.” “To embarrass me further your small penis size is open for discussion.” “Your mother seems to be willing to talk about it in front of all our friends.” “Maybe we should have all had a look at the little darling.” “I’ll bet the girls would have thought it was pretty and petite just like your feet!” “It’s bad enough I have to pretend that you are big enough to satisfy me now the whole world knows that your mother and big sister though it best that you are girlish!” He was crushed, he was humiliated, he couldn’t look at her and when he looked down past the hem of his red skirt he saw the painted toenails peeking prettily from the sandals on his girly feet. “Honey” he said, “It was all in fun, you and the girls were urging me to try on sis’s shoes and one thing led to another.” “How could I have stopped it?” she asked. “You were into it and, and you were a girl!!” “Lift that skirt I want to see your disgusting little penis.” Blushing with shame he complied. She slid his shorts down and said, “These won’t do, its panties for you from now on girl.” “Oh God it is little,” she said. “I never really looked at it.” “It is tiny, almost like a model of a real man’s penis.”

As disgusted with him as she was she used him that night as though he was her bride. When he tried to enter her she guided his head to where she wanted it, placed his pillow beneath her buttocks and kept him at it for hours. He brought her to several powerful shuddering orgasms and even more softer ones. As she was about to peak once more he would move to mount her only to have his head slapped by her or his ears grabbed and his mouth placed right back where she wanted it. When she was finally through she said, “oh that was good, here I have a treat for you” And she took his penis in her hand and quickly brought him off. “Well that was quick, it’s a good thing I didn’t count on that for satisfaction.” “Now clean your self off and go to sleep. Big day tomorrow missy.” “Missy indeed,” he thought as he drifted off to sleep. “I will get this whole thing straightened out in the morning”.

He felt pretty good when sleep finally overtook him. She was already up when he awoke. He heard voices in the kitchen. He recognized his wife’s voice and his sisters. Slipping on his robe over the panties he was placed in the night before he went down for coffee. His wife and sister were looking through a pile of clothing and shoes, his sister was saying, “I don’t wear these anymore, and I know they will fit him, so rather than just give them to the Good Will I thought he could use them.” “ Oh thank you so much, I think he will be so cute in them.” His wife was saying. He asked, “What’s going on girls?” Cathy said, “Cheryl has brought over some things that she says will fit you” “Yeah thanks sis, this is all ladies stuff” he said. His ever-helpful wife replied; “after yesterday I think this stuff as you call it suits you just fine.” Cheryl said, “I have to run girls, have fun”.

After he had fixed a light breakfast for Cathy and himself she ordered him upstairs for a bath and some serious hair removal. “If you plan on wearing this stuff I am going to make sure you look your best.” The fact that he hadn’t planned on wearing it seemed to be lost on her. In the bath his wife assisted him with his shaving she even took the razor and trimmed his sparse pubic hair to a neat feminine triangle then with a slightly wicked smile she took the razor and sculpted the top of the triangle and turned it into a pretty heart. He saw what she had done and watched as his manhood shriveled in his embarrassment. She had him get out and dry off and powder himself with sweet smelling powder. Then she took a small pink box and said, “I’ll bet you haven’t seen one of these” and he hadn’t. It looked like a small piece of lace with strings attached “Watch” she said. She took his penis between her fingers and shook her head, and then she laid it on the cloth. When he started to erect she flipped the small head with her fingernail and it softened right up, “that’s better,” she said to herself. Then she folded the cloth up and began to tighten up the laces. She tightened the little device just as she would tighten a small corset. Soon she had his already not too large penis reduced to about the diameter of his index finger. A small silver lock went through the laces and his small but once proud vestige of manhood was now quite feminine and in her control. She bent down and took the only exposed portion, the head between her lips and sucked. His body tried to respond, blood rushed to the penis, it tried with all it’s little mite but alas no erection was forth coming, he was as soft as a baby, “soft like a girl” she said. With his shaved legs, heart shaped pubic hair and delicately dressed penis he certainly didn’t resemble a man. She patted the sheathed penis and said, “don’t get any ideas about removing it, you’re my girl now little one, and I do mean little.”  Jimmy wore white jeans a pink tee and white flat sandals his still painted toe nails were like little sissy calling cards the latest indignity was the B cup bra that clearly showed through the tee top. The small white clutch bag tucked up beneath his arm reduced any chance of masculine identity to just about nothing. He lifted his head as his wife applied a touch of color to his lips she clipped a pair of silver earrings to his ear lobes and clapped her hands with unconcealed happiness. His misery was obvious he had never been so humiliated in his life. His wife had dressed him in this horrid manner and his mother and mother in law were about to arrive at any minute for a “fun day of lunch and shopping with the girls”. It would be fun for them but he had a feeling that any laughter would be pointed at him.

“The girls” arrived with shouts of “Oh my God, he is adorable” and from his own mother “that little purse is just divine”. In a few minutes they had reduced him to near tears then turned their conversation to where they would go, what they would, where they would eat he was drawn into the conversation with questions like; “do you have lipstick in your bag sweetie?” “Those sandals are really cute and they look comfortable, you made a smart choice hon”. He hadn’t chosen anything is beaming wife had set him up and his sister was playing her hand in the whole thing to perfection. His mother in law noticed how well his white jeans fit him in the crotch area and commented on it. She said, “why it’s as if he has no, male package at all.” “Isn’t that sweet, I guess being tiny down there has its rewards.” Then she turned to his wife and said “Oh dear I am sorry I can only imagine how difficult it is for you.” “You poor thing you must be starving for real size.” “Oh well maybe someday soon you will.

The girls were relatively kind to him there were surprisingly few insults directed at him. It was as though he had become one of them, they were treating him as if he was another woman. Somehow this was even more humiliating than the teasing had been. And his ability to resist this journey into femininity had become impossible for him to resist. Much to his utter humiliation he was becoming a girl of his own free will.

It was decided that some shopping was in order as the new girl was woefully low on lingerie. The Feminine Underworld was a very upscale intimate apparel store. It was not the place any man would feel comfortable in. This store exuded femininity and sex appeal, he was out of his league for sure. The staff turned to greet the new arrivals with warm feminine greetings. He was not spared the humiliation air kissing, shoe compliments and being included in everything by the use of feminine pronouns. Right off the bat he was “just a girl” and it was soon noted that he was the designated customer. As a customer he was quickly assigned a changing room, given a cup of tea in a dainty cup and introduced to a young girl who would assist him in his intimate fitting. This was all done with undisguised joy at his descent into the world of feminine underwear.

Claudia was his assistant and she lost no time in figuring out the order of control here, even though he was the customer, these women would call the shots and the sissy was here for their amusement. Well that worked for her and she would make sure this little sissy was properly pantied and padded before he walked out of here with a dented credit card. Claudia had Jim strip “Oh my God, that’s adorable” she said when she saw the delicate little sheath that effectively feminized his penis. She held it in her hand and felt it attempt to erect. She knew the tight lacing restricted it but she was smart enough to play her hand farther “Oh my it is so tiny and it doesn’t work.” “Well it’s good you’re more girl than boy, isn’t it?” she asked with a smile. So after a few hundred of his dollars were spent and he was humiliated further the girls and Claudia sat down for tea Jim was asked about boyfriends, makeup, shoes and if he was comfortable in his new bra and tummy slimmer. All he could do was mumble in the affirmative. Jim noticed his mother in-law slip Claudia a one hundred-dollar bill and whisper “thank you” as the ladies left the shop. Jim’s new bra held a size larger form; he was now a proud C cup girl there was no way his bust could be concealed. And he reasoned “so what” with his sandals, painted toe nails, feminine pants and tee top the tits didn’t really matter much now he was totally debased and just wanted out.

Jim seemed to come to when he felt the waiter hold his hand as he slid into his seat at the restaurant. It was as though he just now noticed the yellow sundress and white high-heeled strappy sandals he wore. He touched his styled hair noticed his “done” nails and realized he had crossed a line he hadn’t known existed.

Two weeks later the girls had gathered for cards Jim wore a simple white skirt rose sweater and tan pumps with nude hose. His jewelry was simple, his makeup minimal he took their wraps and handbags and put them on a spare bed. He went into his wife’s bedroom after a discreet knock and announced the arrival of the guests. She smiled sweetly at him and said, “you look very nice today dear” he murmured a small thank you. He tried not to look at the man next to her. She was aware of his embarrassment and his discomfort. She said “Did you press Dan’s trousers and polish his shoes like you were asked?” “Yes dear” he replied. “Good, after you assist him with his toilet you can help him dress.” Jim heard the girl’s laughter and heard the occasional comment. He heard his wife say “Oh my God Dan is huge I can hardly walk after he stays over.” Jim’s cheeks burned with embarrassment as he knelt to tie Dan’s black wing tip shoes. Jim had looked inside when he polished them, Dan wore a size 13 wide in a man’ shoe.

A Happy Wife


Sissy Girl Stories