A Maid Man

All characters are over eighteen and all references to past sex happened between consenting adults. Enjoy.

My name is Peter and I was a colossal disappointment to my father. Thats a profound understatement.

My father's name is Paul Vittore. Now that's Pauly to his friends and family but to everyone else it's Don Vittore.

Yeah, he's a mobster and head of the Vittore crime syndicate. Blackmail, online scams, drugs, extortion, muscle for hire, illegal gambling and even porn was the family business. I had no problem with that.

No, I was just fine with the family business, it's the family business and particularly my father that had a problem with me.

The trouble started on the day I graduated from highschool, or to be more precise, the evening I graduated. Me and a few friends were at my house just hanging out planning our future in dad's organization, college life, playing games on our phones, partaking of dad's liquor and just enjoying the fact that highschool was finally over when Vincent casually invited me to suck his cock.

Now this was no surprise as I had sucked his cock several times and even did so in front of my friends who all knew I liked cock and kept my secret cause it got them free blow jobs and because ratting on the boss's son could get them killed.

Ever since I turned eighteen I enjoyed every opportunity to suck cock. I loved the hardness of it in my mouth. I loved being on my knees in front of a man. I loved the salty gooey warm taste of cum. I loved doing something taboo.

When Vinny first invited me to blow him the day after I had turned eighteen, he was just joking but I got on my knees and promptly gave my first blow job and have been sucking cock ever since.

Now back to the evening of my graduation. I was on my knees sucking on Vinny's cock while three of my friends were watching and waiting for their turn when my bedroom door suddenly flung open and my dad, Don Vittore, walked in catching us in the act.

My life turned to shit after that. At least for a while anyway.

Dad made the other boys swear to secrecy on pain of death and forbid them from ever seeing me or coming in our house again. Then he took away my car and my iPhone.

But that wasn't the worst of it... or the best.

"I've made my decision, you're not going to college. No use wasting an education on some sort of faggot. No I have plans for you boy." My dad said in front of my mom and I at the dinner table three nights after I was busted sucking cock.

"Honey, go easy on him. He's just a teenager experimenting." Mom said in my defense.

"Go easy on him? GO EASY ON HIM!!! Have you gone soft woman? He was sucking cock on his knees. I'm the Don. What would happen if someone found out my kid, the presumptive air to my family and estate, the future head of the Vittore syndicate, was a filthy cocksucker? I put up with him being a short pathetic skinny kid and a pansy at sports telling myself he was just a brainy nerd or some shit but this? This?" My dad said in a fit of anger.

"It's not really a big deal these days. lots of people are into that." Mom said as she continued to come to my defense. I knew better than to say anything. I knew my dad's anger all too well.

"It's settled. After things settle down a bit I'm sending him, to Don Cantory in Frisco. His a pathetic waste just like Peter here. He can start working for him out there and if someone says my son turned queer I can blame Bruce since everyone knows what he is.

Bruce Cantory. I'd heard of him. He had a reputation of breaking his rivals and making them his personal bitches. Him and dad did some business but didn't like each other. He was said to be a hard boss to work for and a sadist.

The rest of the dinner passed in silence as I pondered my fate. At least I wasn't gonna be completely cut off but I would have to leave New York and live in San Francisco.

I spent a couple weeks practically trapped in my house as I had no car and no friends I could call to hang out with since dad scared them away.

Then the day finally came when I was to head out to S. F. to start working for the Cantory syndicate. I had hoped dad would give me my car back so I could drive cross country but no such luck. No, I was to fly. I did fly first class as I was still a Vittore.

When I arrived I took an Uber out to Don Cantory's estate which was much more lavish and bigger than dads place in New York. And it had an ocean view and plenty of acreage. The benefit of not living in NYC I guess.

"So, your little Peter. You dad said he was sending you as a sort of peace treaty between our two families and you would help me with my business out here and I would be more generous dealing with your father in New York. Well, I do have some work for you. In fact I have decided to give you your button kiddo. I'm gonna make you." Don Cantory explained.

Wow, usually they don't open the books for someone until they're at least thirty or did something really important.

I'm gonna be a made man. A full member of a crew. Fucking awesome.

"Thank you Don Cantory, I will serve your family with loyalty." I said hardly believing it was possible.

"I know you will. I know I'm rushing things a little here but I have need of you right away so I want the ceremony to take place later today. You ready?" He asked and I nodded my head just before something was shoved in front of my face and everything went black.

When I woke up I was laying flat on my back in a large bed in a bedroom that was all pink and there was a mirror on the ceiling that showed me I was wearing a dress. Not just a normal ladies dress but a full blown wedding gown. There was also a gopro cam on the headboard watching me.

I tried to move only to find my arms and legs were bound and secured to the bed.

"Well look who's awake." Don Cantory's said as he entered the room soon after I awoke. So here is the deal bitch. Your dad sent you here to get rid of you for being queer and sucking cock and I agreed because I want to humiliate him by making you my bride and then using you as my personal house maid. That's right kid, I own you and unless you want to find yourself on the run labeled as a snitch you'll do as I say." The Don explained.

"I thought you only broke your rivals, I swore to serve your family. You said I was getting my button?" I said staring at my frilly image in the mirror on the ceiling.

"Your family is my rival and I will break you and I promise you will serve me. Now as for your button, I already gave that to you." He said and then grabbed the flowing skirts of the wedding gown I was wearing and pulled them up revealing the pink chastity cage on my dick. The site of it outlined by a garterbelt and stockings would have made me hard as a rock if not for the cage.

"There's your button." He said.

I started to cry a little.

"Now the ceremony is in about an hour." He said then added, "Won't your dad be so pleased to find his son and air had given himself to be his rivals wife. I will make sure he get copies of all the wedding photos.

The Don left me to my crying until someone came in nearly a half hour later to fetch me for the ceremony. Several men who worked for Don Cantory roughly escorted me outside to a waiting limo which then drove us to some sort of banquet hall.

I was then forced to stand at the back of a crowded room waiting for the wedding march to begin. Several of what I could only assume were drag queens were provided to act as my bridesmaids and all wore disgustingly frilly pink gowns with full huge skirts. Two took hold of the train on my dress and walked behind me while the other two walked on either side of me and each carrying a bouquet of flowers which nominally concealed a small pistol.

The the wedding march began and having no choice whatsoever, I began to walk while my so called bridesmaids escorted me down the aisle. I found that walking in a dress, particularly one with skirts as huge and cumbersome as this one, was quite difficult and I had to take small steps which only prolonged the agony and made me seem more feminine.

Sucking my friends cock was one thing but this?

I got to the altar and the pastor, began the wedding ceremony.

"Dearly beloved, we are gathered here today to witness this man, Peter Anthony Vittore, surrender his manhood and give himself as a woman and servant to Don Bruce David Cantory and be his everlasting wife." The pastor began.

"Do you Don Bruce David Cantory take this failure of a man, Peter Anthony Vittore to be your lawfully wedded wife? To have and hold, to love honor and cherish for so long as you both shall live?

My soon to be husband said, "I do."

The pastor continued to me saying, "And do you Peter Anthony Vittore acknowledge your failure as a man and accept the role of a woman by taking the name of Marie Cantory. And do you accept your place on your knees before your husband Don Bruce David Cantory to have and to hold, to love honor and OBEY for so long as you both shall live?

And then I heard not one but two small pistols cock and I uttered my fate. "I do"

"And now the rings." The pastor said.

Another bridesmaid then presented a small pillow with three rings on it. Two wedding bands and what looked like a diamond engagement ring. Two rings, the diamond ring and one wedding band were placed on my left ring finger by the Don and I was made to place one wedding band on his finger.

"And by the power vested in me by the State of California, I now pronounce you husband and wife. You may now kiss the bride." The Don then grabbed me by the back of my head and pulled me to him, he then leaned down a bit as he was a good deal taller than I was and planted a passionate kiss on my lips.

I had never been kissed by a man before and if I weren't a slave I might have enjoyed his tongue in my mouth. As he kissed me I did note that the pastor never asked if anyone cared to object or forever hold their peace. Mob weddings?

"Now that the two of you are married, it's time to become one flesh. Take the bride to her bedchamber and consummate the marriage by deflowering her." The pastor said and he then indicated a small door behind the altar with is hand.

My new husband picked me up and carried me through the door with my bridesmaids in tow where a king size bed was waiting.

On the bed were bondage gear, a gag and an unopened box of tampons.

"Last choice you get to make. What position do you want to get deflowered in?" my husband asked me.

I thought about it for a minute thinking about how my dad had basically cast me out and how I needed to find a way to make my husband my friend and knowing his cock was going up my ass weather I wanted it or not so I answered, "Deflower me in the most degrading way possible so my father will be utterly humiliated. The more he suffers, the better wife I will be."

He looked at me with surprise and I knew that even though I was in for a bad ride, I had said the right thing for the long term.

And so I was bound on the bed on my hands and knees and silenced with a gag while first my husband and then each of the drag queen bridesmaids fucked my ass.

The first cock, my husbands, hurt like hell since I had never been fucked before but to my surprise he took it slow and easy with me even going so far as to let me get used to him inside me before giving my ass a real pounding.

There were cameras positioned to witness my deflowering and I made sure to look right at them with my gagged face and cry so my dad could see.

The tears were real, I was humiliated and being forced into matrimony as a woman against my will and my asshurt like hell but I found that being on my hands and knees in a wedding gown was more thrilling than when Vinny had me suck his cock on my knees.

My husbands cock was followed by four more. Each of the bridesmaids took their turn filling me with their sperm.

I was left bound and gagged for a couple hours only to be interrupted once by my husband who told me I was gonna clean up after the reception which I was not allowed to attend.

He made a point of telling me that I was more than just his wife. I was also his Maid and would be used as such.

I guess I am a MAID man after all.

The last humiliation I was made to endure before being allowed up from the bed was to have one of the bridesmaids shove a tampon up my ass to keep all the cum from leaking out. Then I went to the reception room to begin cleaning up like a maid.