A Submissive Sissy

Here you'll find my favorites Sissy & Femdom stories, the best one I've ever read over the net since many years and believe me, that's a lot ! I'm also a wool fetishist, so you may come accross this type of topic around here too... Hope you'll like it !


Structure in his Life

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Jim lay awake waiting for the pressure to subside. The chastity device he wore prevented even nocturnal swelling of his penis. He often awoke five or six times a night from the discomfort of his penis attempting to erect. He had learned not to toss and turn or express his displeasure in anyway. He knew that if I was awakened by his movements or complaints I would be angry and as he knew from past experience a swift and painful punishment might be administered along with a length of time added to his belting.

The device he wore was unique in that it completely hid his male organs and had a small cod plate that gave him a nice feminine look. I really enjoyed the look so much so that I in no time had him in panties and soon after that full feminine attire. He was so anxious to have his penis released for even a few minutes that he had readily agreed to being crossdressed. He would bargain away his dignity for the pleasure of a little freedom.

Tonight all he wanted was to have an erection. Just to feel it get hard, just to see it, just to feel like a man for a little while. He glanced at the clock and saw he had only about an hour before he had to get up. He was getting up early now that he had his new job. The job was the latest indignity he had agreed to suffer for my amusement and an ejaculation or two. I pretended to be asleep and lay there listening to my poor husband try to find some comfort in his situation.

He got up at six and started coffee then he took his shower. I came into the bathroom to see Jim applying body lotion to his freshly shaved legs. The pink polish on his toes and finger nails looked sweet. It was amazing how quickly he had learned the rituals of maintaining his feminine appearance. I had no illusions about the new girly Jim being happy about his "look" and I also knew that the smile and yes Mistress he so often had for me was anything but forced. Jim would lick my anus for the promise of two minutes without the belt; in fact he had done just that.

Jim was in the fifth week of a six-week belting. He still had nine days to go and didn’t know yet if he would have sex, masturbation or anything but a cleaning to go with a promised four hour release. The release of course didn’t mean complete freedom. From the start of his belting I had insisted on a form of bondage before I let the penis loose. Jim’s hands would be cuffed to a collar at his neck or behind his back, after his time was up the device would go back on and Jim’s manhood would go by by for a time specified by me.

I lay on the bed drinking my coffee and watching Jim as he prepared for work. He had on just a bra and panties as he gathered up the things he would be wearing today. Jim was working for my friend Mary Beth. Mary Beth had a small salon in an upscale area of town. She did hair, make up, skin care, nails and about any beauty and personal care service that the wealthy ladies of this Southern California beach town could want. Jim was the receptionist, gave foot rubs to tired career woman, fetched coffee and ran errands for the girls who worked there and did little personal things for select clients. Jim often polished shoes, dropped off dry cleaning served coffee or did little shopping trips for the wealthy women who frequented the shop. Jim only worked three days a week for Mary Beth so he had plenty of time for house keeping and things I needed done for me. Jim was a good worker and was eager to please the ladies at the shop. He knew full well that any news of a less than perfect attitude and job performance would result in a length of time being added to his sentence. The girls at the shop all knew of Jim’s situation and had all seen the device. They all thought it was cute and was just the thing to keep his thing out of trouble. The clients didn’t all know of the device, some did and enjoyed teasing him about how long it had been. The ones that didn’t know probably thought Jim was a homosexual or a submissive sissy.

Jim was required to wear feminine clothes at all times but was not always dressed as a woman. Often poor Jim wore ladies slacks, shoes and a cute top with his earrings but with out make up or hair for his "sissy boy" look. Or he wore one of his "boy outfits". He had three, just alike except for color one powder blue, one black and one in rose. They consisted of velvet short pants with a high waist, a short collarless jacket with a cute flair at the hem to give him a nice feminine figure. He wore this with a white blouse that had a nice little rounded collar that laid on the jacked nicely. Ankle socks and Mary Jane shoes and his purse completed the look. Jim had agreed to the fitting and purchase of these humiliating outfits after I offered him three nights of penile freedom. At first he said no way but by the time three weeks had rolled around Jim knelt at my feet and asked me to dress him as a sissy boy.

Mary Beth knew of a seamstress who would do the fitting and sew up the suits for the boy. Jim, properly belted of course had to go to her place of business and have his fittings and try on’s just like a girl getting a prom dress. Just before the suits were complete Jim was sent shoe shopping for Mary Janes in black patent and white kid or patent. I had seen a women’s flat styled almost like a child’s Mary Jane in one of the department stores and had ordered Jim to dress in women’s pants, a tee shirt, knee high stockings, his black ladies loafers and his purse. He did as told went to the department store and tried on the shoes bought both pairs. Later he told me the girl who waited on him told him he had pretty feet and should show some toe. I thought "how sweet" and put Jim in sandals for a week, well a pretty foot is something we can all enjoy, Jim didn’t seem to enjoy it too much but I know other people did, I saw them smiling.

I was having coffee on the rear deck when Jim showed up with the coffeepot and a toasted bagel for me. He was dressed for work. He had chosen a longish black skirt with a fuchsia and green print, dark hose, black low heeled pumps, a fuchsia top and gold jewelry. I said "my my aren’t we lovely today?" Jim blushed under his make up but I didn’t let him off the hook. "Why are you so pretty today, are you and the other girls going somewhere?" Jim said he and the girls were going out to lunch. "Well well my little sissy husband has bonded with the other girls, has he?" He shyly nodded yes. I sat my cup down and looked at him, he was really very pretty and had become used to acting and moving in a feminine manner. "You know sweetie this make me very happy, you’ll tell me all about it tonight won’t you?" We both knew the question was more a statement, he knew never to refuse to answer me. Jim poured me more coffee and turned to leave, when he got to the door he turned back as if to say something, thought for a minute and shyly said "thank you for giving me some structure in my life, I love you."

A Happy Wife