Sissy Husband: Honeymoon

By Jans sissy sally


Matthew and Jan were on their way to the Airport to go on their expensive four weeks honeymoon to Hawaii. There was only one more thing to do before they could leave. Jan had insisted to pay a visit to her Mother to say goodbye before the trip.
When they arrived at Linda's home matthew was alarmed when he saw his Mother's car in the driveway. They found her having coffee with Linda in the living room. Jan excused herself to use the bathroom and left Matthew alone with his Mother Blanche and Mother in Law Linda.
"We need to have a little talk, matthew," his Mother began. "Jan has informed us about what happened during your wedding night and Linda is now justifiably concerned about your ability of being a suitable husband for her daughter at all. I however assured her that you have many of redeeming traits regardless of your shortcomings in bed."
Matthew was dumbfounded. Had Jan really told them everything that happened? Shortcomings in bed?
"I… I… don't understand…" he stammered, when he remembered he had a flight to catch. "Do we really need to discuss this right now?"
"You soiled your Wife's feet with your premature ejaculation boy, and while she took a shower to clean herself from your filth you masturbated alone in bed on your wedding night. Don't you think that is a reason for concern?" his Mother replied. "You should call yourself lucky Jan has not annulled the marriage right away. We absolutely need to discuss this now to give your Mother in law some peace of mind about what sort of things you can do right. You know how we do this sort of thing, undress!"
"Do I really have to…" Matthew attempted to protest, but when his Mother snapped her fingers and said, "NOW!" he immediately went silent and began to unbutton his shirt.
She turned to Linda to explain: "Every time we have to address some issues, I had him in the nude. It makes him much more agreeable, I hope you don't mind?"
"Absolutely not," Linda replied. "And I must say that thing you do with your fingers is quite impressive, Blanche. Is that some kind of hypnosis?"
Blanche laughed. "No, this has nothing to do with hypnosis. It is his trigger to avoid the consequences of not following my instructions. It was a hard piece of work to get him conditioned that way."
"That sounds so convenient. Does it only work if you do it?"
"Not at all. He instantly reacts with silence and obedience to any random finger snapping. It takes him a couple of seconds to snap out of it and comprehend if it was even directed at him. His younger Sister did it all the time just to tease him. You may want to try yourself any time."
In the meantime Matthew had finished undressing. He had been deliberately slow because he hoped Jan would return and make them realize that they had to leave for the airport. Now he was standing naked before the two Ladies with his hands over his privates trying to retain some dignity and to hide his chastity cage.
Blance had of course noticed it regardless and pointed at his crotch. "What is that, boy?"
The moment matthew opened his mouth to answer he was interrupted by the sound of a finger snap.
"On your toes! Hands on your back! Eyes on the floor!"
He had followed all the commands before his mind even realized they did not come from his Mother but his Mother in law.
"Oh my god, it really works." Linda clapped her hands in excitement and laughed out loud. "That is incredible!"
Blance was pleasantly surprised and praised Linda's execution of the snap. With hands behind his back matthew now openly displayed the metal device that was tightly fastened and locked around his testicles keeping his penis confined in a tiny curved tube that prevented any kind of expansion or touch.
He remained silent looking down at the ground and balancing on his toes, while Linda told Blanche the story about his vow of chastity in every embarrassing detail.
"Had I ever known about these, you would have been locked since puberty boy." His Mother laughed and beckoned him over to take a closer look and assure herself of the effectivity of the device. "This is perfect," she stated after some pulling and squeezing. "Just to think about the efforts I made. I kept him tucked away in tight girdles night and day to prevent masturbation and erections. He had special mittens for the night and he would have to ask permission to use the bathroom and was not allowed to lock any doors so I or his Sister could walk in on him at any time no matter where he was in the house. Grace was especially keen to keep him on his toes. Oh the stories I could tell…"
She paused and Matthew seized the opportunity to get a word in. "Mother, we really need to get going or Jan and I will miss our plane"
"Oh, don't you worry dear. I promise you nobody will miss the plane," Blanche replied. "We are not done here yet. Now go pick up your clothes and show Linda how neatly you can fold them."
"Yes, Ma'am," Matthew replied with a hint of a sigh and began the task.
"I really enjoy how respectfully he addresses you, Blanche. I like the sound of someone his age using 'Miss' and 'Ma'am'. Of course I don't mind that he is calling me Linda, even though he never asked permission as far as I remember."
"Did you hear that matthew? Linda just told you something about herself in a very subtle way. Isn't that wonderful? That is exactly why we are having this little talk. Let's see how you can use this clue to act in a way that will please your Mother in Law."
Matthew didn't think it was subtle at all, but he knew better than to object right now. All he wanted was to get this 'talk" over with.
"I think to show your appreciation and respect, you want to address Linda by her last name from now on. Every sentence directed to her you want to begin with 'Mrs. Rivers' or end in 'Ma'am'. Or both, regardless if in private or public."
"Oh that is so sweet of you Mandy, I really appreciate that," Linda said, without considering matthew's potential opinion in the matter. "…and you folded up all your clothes so neatly too. Your mother was right, you have excellent homemaker skills."
"Of course he also knows how to wash and iron them. When he still did our laundry at home, Grace and I had him do all the delicates by hand and hang them up to dry. I also taught him how to cook and clean the house, he gives excellent massages and pedicures and you can trust him to polish your most expensive heels to perfection," his Mother added.
"That sounds like our little Mandy here would make any housewife jealous," Linda concluded.
"Isn't it nice to hear your skills are being appreciated? Did you notice Linda feels comfortable enough now to call you by a affectionate little nickname? I think we came a long way in just a few minutes and created a firm foundation on which your relationship of Mother and son in law will be able to grow on. Now remember to thank Linda for her nice words, Mandy."
Matthew didn't like the fact that both of them were calling him mandy now, but he was happy that the 'Talk' was obviously over and he didn't want to stir any more debate, so he simply said, "Thank you Mrs. Rivers, Ma'am."
"You are welcome, dear. I feel so much better now that we established your place in the family, dear. Don't you think?" Linda replied.
matthew didn't like the insinuation about his place in the family and neither did he like how both of them looked at him in anticipation of his answer. He told himself that it was only for a few more minutes and he would be out of here and he didn't want to leave for his honeymoon with his Mother in Law mad at him. He swallowed his pride and answered,
"Yes, Mrs. Rivers"
Both Ladies smiled and gave each other a knowing look. "I believe this calls for a little celebration!" Linda suggested. "Drinks anyone?"
"That is a wonderful idea!" Blanche agreed. "Mandy makes excellent Margaritas from scratch."
"Come on then sweetie, i'll show you the kitchen," Linda said and walked off, obviously expecting him to follow.
Matthew his Mother a desperate look extending his hand at the the folded clothes on the table, hoping she would give him permission to get dressed again.
"You are the one who is in a hurry boy," she said instead. "You may get dressed while we are having the drinks, now don't make Linda wait."
But Linda was already waiting when he entered the kitchen. A pair of shoes in one hand and a apron in the other. "Here are some house shoes for you so you don't get cold feet on the tiled kitchen floor."
They were pink velvet ballerina flats with a hard sole and a big decorative bow across the toes. "Don't give me that look, I don't have any others," Linda said when he hesitated for a second.
They felt very small, but having his Mother in law towering over him, tapping her heels impatiently while he was crouching nude on the floor to slip into a pair of tiny girly shoes made him feel so intimidated that he didn't dare to complain about the size. He just struggled to squeeze his feet into them regardless.
"See? They will do just fine for you," Linda said and added, "What do we say?"
He instantly replied, "Thank you Mrs. Rivers, Ma'am."
"Better," she remarked with obvious resentment in her voice. As soon as he was done with the shoes she slipped the apron over his head. "We don't want you to mess yourself up, do we? Turn around."
It was an old fashioned pinafore style with wide ruffled shoulder straps and hem. It closed behind from his neck to his lower back, leaving his buttocks exposed and framed in ruffles as the sides extended down to the front of his knees. Linda zipped him up and tied several additional ribbons into pretty bows on his back. When Matthew thought she was finally done he felt something being slipped over his forehead. He was so surprised that he instinctively reached up, which earned him a slap on the fingers. "Don't touch it. I don't want any hair in my drink," she stated in a tone that allowed for no debate. Checking himself in the reflective surface of the glass cupboard it appeared to be a turban style headband, matching his shoes in color and style with the decorative bow twice as big on his forehead.
After Linda had shown him all the ingredients, she pointed at a silver tray and said, "When you are done stay as you are and serve the cocktails to us in the living room." Before she left him alone, she kept tapping her heels impatiently until he remembered to say, "Yes Mrs. Rivers," again, which she commented with, "We will need to work on that."
Matthew hurried to get the drinks ready. He heard some excited laughter coming from the living room and, to his relief, Jan's voice eventually joined in. That made him feel relieved and he prepared one more glass for her. Now they would be as as good as out of here.
Little later he carried the tray with the drinks out of the kitchen accompanied by the delicate sounds the shoes made on the hardwood floor. His feet were aching but he was happy to find everyone in high spirits. "It was fantastic, Mom," Jan just said with her back to him.
"The drinks are ready, Ladies," he declared and presented the tray. Jan turned around and burst into laughter "Oh my God, you look adorable!" she said when she finally caught herself, Blanche agreed wholeheartedly. They made him turn around a few times and he swallowed their humiliations quietly.
"You know, that these used to be my shoes and headband Blanche?" she revealed and turned back to matthew. "I can't believe they fit you! I had them when I was like sixteen!"
Blanche snapped her fingers indicating that he was supposed to serve the drinks and he walked up to each of the Women. They all took their cocktail with the words: "Thank you, mandy."
There was one margarita left, since matthew had made one for himself as well, but before he could set the tray down to take it someone snached it from behind. Matthew looked and his heart sank even lower when he saw Mark, Linda's young lover. Where did he suddenly come from? He was the last person matthew wanted to see him like that.
Mark sneered at him, raised his drink and said, "Thank you mandy."
"You remember Mark?" Linda said. "He was your best man and even took care of your bride most of the evening when you wouldn't dance with her. I don't think I ever heard you thanking him."
Matthew didn't say anything, he refused to thank Mark for the humiliations he had to endure at the wedding.
"Don't be like that sweetie," Jan said, "Mark really was a perfect gentlemen at the reception, pitching in while you spent most of the evening at the Bridesmaids table. You should show some gratitude."
Matthew clenched his teeth, and finally said, "Thank you, Mark."
Blanche remarked, "He is your Mother in Law's boyfriend. Address him properly like I taught you to address my boyfriends!"
One deep breath later Matthew uttered, "Thank you, Master Mark."
Mark pinched him in his cheek and sneered, "You're welcome, doll."
Everyone finished their drinks while having some pleasant conversation. Except matthew just stood there disregarded, trying not to break into tears.
"Well, I better be going now," Blanche suddenly said, "and our young lovers better hurry to catch their plane too I suppose."
"Be a dear, take these back to the kitchen and clean up the mess you made, while I say goodbye to your Mother and Jan," Linda said when everyone had put their glasses back on the tray.
Matthew didn't even have time to open his mouth as his Mother anticipated his answer. "You may as well remove the word "no" from your vocabulary son. If Linda asks you a favor you will smile and do whatever she wants you to. And I better never hear any of the contrary. I hope you understand? Now show us how it's done."
Matthew forced himself to smile and say, "Yes, Mrs. Rivers," before he headed for the kitchen.
"I'll be there in a minute," she stated as he walked out.
For the past few minutes since he had been made to thank Mark, matthew had felt like in a daze. Just now he started to regain his senses. Finally it was over. He placed the cocktail glasses in the dishwasher, put all the ingredients back in the cupboards and wiped the countertops. There would be nothing to complain about, nothing that would give anyone any reason to delay this any longer. He wouldn't wait for Linda to come in either. He was done and he would get dressed. It was time to leave.
As he walked back into the living room, it was empty. Everyone was gone and even his clothes had disappeared from the table. His shoes, his watch, his wallet, everything.
"Didn't I tell you to stay in the kitchen?" Linda said. She had just come back in through the front door.
"Where is everyone?" Matthew asked.
Linda raised her finger. "What do we say?"
"Where is everyone, Ma'am?" Matthew corrected himself.
"They are gone, of course. Your Mother went home, and Jan and Mark are off to Hawaii. It's only the two of us now."
"But…"
Linda snapped her fingers and matthew stopped talking. "It was really your Mother who suggested that you would be no fun for Jan during the honeymoon, when she heard how useless you turned out to be in bed. All of us agreed of course and I offered Mark as a stand in, because he is an excellent lover. They actually had sex upstairs just now, while you demonstrated your homemaking skills to us down here. Jan was completely blown away."
Matthew realized what Jan had been so excited about when he served the cocktails.
"She will have a wonderful time with sex any time of the day she wants to. I instructed Mark specifically to tend to her every whim. He carries your wallet, as we figured your Wife should be spoiled with your money since you are the husband after all."
"Which brings us to your part in the plan and why you will be going along with it. I promised Jan I would turn you into a perfect little housekeeper for her, so you will be staying with me for the whole time. Fortunately you already received a solid foundation of useful skills by your Mother's wonderful upbringing. We will take this further and I will personally train you to be a ladies maid. I will also teach other important techniques you will need to keep my daughter from divorcing you."
She walked over to sit in the big comfortable chair in the corner of the living room.
"You see mandy, you really have every reason to be grateful, don't you? And I will make sure you show me that gratitude every single day. You will remain locked up for the whole duration of your time here and you will learn ways to bring a Woman pleasure that don't require your useless little thing."
"Now Before you say anything, I want you to think carefully what your first words to me should be. Remember, you have nothing right now. Your clothes are gone, so is your money, your ID, the car, the keys to your home as well as the ones to your chastity device. You have no place to go and your own Wife, your Mother and even your Sister support this approach. Nobody will help you. You are under my complete control, and there is nothing you can do about it."
She pointed at the floor in front of her. "Now I want you to come over here and get on your knees. We are going find out about your foot massage skills," she said as she crossed her legs.
Matthew stared in disbelief, as he still tried to wrap his mind around everything he had just been told.
Linda snapped her fingers. "Now!"
Matthew walked over to her in his painfully small pink velvet shoes, dressed in a frilly pinafore and little girl's headband. He dropped to his knees before his Mother in law's feet.
"You may give my heels a little kiss on the toe before you take them off, Mandy," she said.
"Thank you, Mrs. Rivers," he answered.

Sissy Husband: Wedding

 By Jans sissy sally

It all began the morning of the ceremony when instead of a tuxedo a different kind of suit was delivered to the hotel by mistake.
The suit's black velvet jacket had slightly puffed sleeves, was taken in at the waist and had a single polished gold button holding it together. It came with a shiny silk blouse, a ribbon bowtie around a ruffled collar and a tiny velvet veil cap with a large black bow. The pants were velvet hiphugger leggings.
There was no time to change it and cancelling the wedding was not an option for Jan. She was not joking when she told him he would wear either that suit or her dress instead.
Matthew had never felt so very embarrassed in his life no matter how many times Jan and Linda assured him that nobody would notice while they helped him to get him into the ensemble.
To make his body match the contoured clothes, nis Bride and Mother in Law made a combined effort to lace him into the provided waist cincher as tightly as possible. The fact that he was hardly able to breathe was casually ignored by each of them.
While they dressed him in the blouse and jacket Matthews Mother and Sister entered to say hello before the ceremony. They were affectionately welcomed by Jan and Linda and did neither seem to be shocked nor surprised by Matthews outfit.
His Mother gave him a pitiful look as if she had expected nothing else anyway, while his Sister remarked, "The shoes don't match little brother," looking at the black wingtips next to him on the floor. She was three years younger than him, but she always called him little brother ever since she outgrew him.
"The heels that came with the suit don't fit," Jan joked, "we already tried."
"What a shame," his Mother snidely remarked, "you could have been as tall as your bride, if she was wearing flats."
Everyone was excited by the idea and Jan assured him she wouldn't mind wearing low heels. When matthew attempted to point out that it could be him minding to wear heels, he was muted by a single "hush" of his Mother snapping her fingers and pointing at the floor. He immediately stopped talking and lowered his head. Jan and Linda gave her an impressed look.
"He can wear mine," his sister suggested to break the sudden moment of silence. "My size will fit him in hose."
"Is that a fact?" Lindas asked, obviously curious.
"Yes, I used to dress him up all the time when we were little... I mean HE was little" She chuckled at the thought "ever since i discovered my old dresses would fit him, he was like my favorite little doll to play with."
She sat down to take off her heels. They were beautiful black Louboutins with ankle straps.
"We had them for years. They used to be Mom's until I begged her long enough to give them to me."
"But they look like new," Jan marveled.
"Oh yes, all our shoes are very well maintained, aren't they matthew? He must have buffed and polished them a million times. Mom was always very particular about shoe care. I remember coming home so many times to find him standing sobbing in the corner with sore buttocks and nothing but a pair of heels on his feet that had failed to meet Her standards. He may even have worn these before."

Jan and Linda were absolutely fascinated by these revelations and the Women decided they would all get together one day and talk about how matthew grew up.
"He can prepare snacks and serve drinks, it will just be like the sunday afternoons with my bridge club," his Mother suggested while wrapping garters around matthews waist for the stockings he would need to wear with his Sisters heels.
"It may be be the only time in your life she is not looking down on you," Linda teased once they stood next to each other fully dressed.
The tight leggings ending above his ankles did nothing to hide the heels and the red sole served as the perfect eyecatcher.

"Now that he is wearing something old and something new, he will need something borrowed," his Mother said, taking off her pearl brooch and pinning it to his lapel. "And something blue!" his Sister added while she was attaching the little veil cap to his hair.
"Don't worry," said Jan, "he is already wearing something very blue," playfully clutching his crotch with a knowing smile.
The Women in the room all burst into laughter at the gesture and Matthews bowed head turned beet red.

Just before the ceremony they decided to change tradition and Matthew felt even more ridiculous and embarrassed as he staggered down the aisle next to his Mother, while Jan was waiting ahead in her wonderful traditional dress.
The heels made distinctive sounds on the chapels stone floor and he could hear amused whispering from the crowd.
Matthew was glad that it was a rather private wedding. There were only his Mother and Sister from his side of the family and all of Jan's attending friends were Women, most of them bridesmaids. The only other male was Linda's new boyfriend Mark. He was a tall handsome man, able to look down at matthew despite the heels and he was of course wearing a proper tuxedo. Since matthew did not have a best man, Linda simply decided that Mark would be perfect to fill in.
Since matthew had agreed to give up his last name and take Jan's the registrar pronounced them "Mr. and Mrs. Janyne Rivers" to the amused giggles of the attending.

The humiliations continued during the reception. Since matthew was not able to dance in heels, Jan was mostly dancing with Mark while her newly wedded husband would stand at the side watching them. He had been given the brides bouquet and pearl clutch to hold so they would not burden his Wife while she was swept over the dancefloor by a complete stranger.
At one point little Maddy the flower girl discovered that matthew was basically wearing the same outfit as the bridesmaids. The only difference was that their suits were in pink and came with pencil skirts instead of leggings. Once she pointed this out to virtually everyone matthew was occupied by the bridesmaids. He was included in all their group pictures, still holding the bouquet and purse. They had him sit with them at their table and gradually transformed him to match their look even more. Everyone, including Maddy, constantly took pictures of every stage, posting them on Facebook and tweeting them to their friends.
Once Jan eventually decided it was late, she found her husband in full Bridesmaid makeup with pink lipstick, pearl earrings clipped to his lobes and several strands of pearls around his neck.
Since there had not been taken a photograph of the young couple side by side, this was how Matthew ended up on their official wedding picture. A newly wed husband in a feminine suit, heels, makeup and jewelry on the side of his beautiful Wife Jan, who had changed back into her own heels in the meantime, being considerably taller than him.

As much as he would love to forget about the ceremony and the reception the wedding night was an even bigger embarrassment to him.
Matthew had not climaxed for more than six months prior and he hardly even had any erections ever since his proposal.
It had been Linda, his Mother in Law, who convinced him that it would be so romantic to vow chastity until the wedding. Jan had loved the idea and it may have even been romantic if they both had made the same pledge, but his fiancee did not even address that issue when she accepted his offer and he had to follow through with it all by himself.
When Jan caught him stroking in bed in the first week, she discussed the matter with her Mother and they decided Matthew was too weak willed for the challenge and it would be best to take measures to support him with his vow.
The same day they took him to an adult shop where he was fitted with a stainless steel chastity tube that would prevent not only touching but also any kind of erection. The sales Lady recommended to add a little padlock, if they suspected he could not be trusted with the device on his own. Since that was obviously the case he was locked into the device right then and there and both his Fiancee and Mother in Law would keep a key for "emergencies."

On the wedding night Jan had a special surprise for matthew. Before they celebrated their matrimony in bed she would make a rubber cast of his penis to remember the occasion.
The kit was a plastic tube filled with some kind of paste. His member instantly sprung into action the moment the device was removed. Jan took some baby oil and gently rubbed it in for protection. These few seconds of her hand stroking him was enough to take him to the edge. When he was instructed to push his member into the tube to make a mold he almost came, and barely managed to restrain himself.
It took the paste 30 minutes to set and Jan made him bring her to climax three times with his tongue to "pass the time". He had a lot of experience with that method because it was the only kind of sex they have ever had and Jan was very fond of it.
Even before he was locked in the device he had never been allowed to penetrate her.
When it was time to remove the tube he was still completely erect and it took some effort to pull it off. Jan twisted and turned the tube and the moment it eventually came loose the stimulation became overwhelming and matthew could not help but spurt a massive load all over the floor and Jan's feet.
His penis shrivelled up quickly when she looked at him in disappointment. He did not dare to object when She told him to lick it off her toes. He went down on his knees and cleaned her as good as possible with his mouth, then she left him to clean up the rest of his mess to take a shower.
When she came back Matthew was lying in bed stroking himself to an erection in anticipation. Jan thought he was masturbating and was furious. Without allowing him a word of explanation he was placed back into the device and told to sleep on the couch.
And that was the wedding night.

For a week Jan hardly talked to him and since he didn't want to address the issue matthew kept wearing the device.
He was very relieved when she started packing their bags for the honeymoon the other day. Everything would be alright. Four weeks in a first class hotel on Hawaii would make everything right. It had cost him a fortune, but right now it seemed even more worth the investment.
Nothing could go wrong now...