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...