I would love to take comments at slutbttm4u@yahoo.com and this is a fictional story though I wouldn't mind it happening to me.
I can see you asking why would I allow this to happen? Well. Amber is one good looking woman and we experimented and I thought that is what it was.
It was about 2 weeks before Halloween and Amber and I were having another great night of sex or at least I thought it was.
As we were laying in bed she said," Joey, will you do me a favor?"
I said," Yes, sure babe."
She asked," Will you suck on a dildo and if you do you can do anal penetration on me."
Now me as a guy being able to fuck her in the ass well that was too much of a temptation what I didn't know and should have was she had plans with me starting on Halloween.
So I said," Yes, babe I will do that."
She brought out a thin 6" dildo and she said," Now, I want you to gradually work it down past your gag reflex."
So I did that for a week and then before I knew It she had me practicing on 7" dildo and while I am doing that I am fucking her ass with my 6" cock.
Now by 2 nights before Halloween, I can deep throat a 12" dildo with no gagging and so then she showed me my costume and well I was going to be dressed as a whore.
I asked," What are you going to be dressed as?"
She said," Your madam oh don't worry it is just for Halloween and it will be good for laughs."
You are saying you are believing her and yes she has been my girlfriend for 3 years and she never showed any interest of me cross-dressing before then and it was for Halloween.
So Halloween night came and she put on the breast forms on me and then helped me with the bra and then she tucked my cock with medical tape and I put on a pair of thongs. I finally got dressed and the makeup on and I looked at myself I looked like a cheap whore. During this time she had me learn to walk in heels and I was walking in 4" heels and of course my ass swayed.
After we backed out of the drive in her car she said," Here is the deal first your name tonight is Candy I think that is a good little whore name. Secondly, you will do as I tell you or I will send these pictures to all of your friends."
I looked at them and that was me sucking on all the dildos with what looked like pleasure on my face. Then there was me dancing in the different women's skirts.
So I sunk my head and I said," Yes, mam."
She smiled and said," Nice way to address me and I want you to entertain some of my co-workers."
I asked," Like how?"
She said," From sucking their cocks to letting them fuck you."
We pulled up to her office and she said," They are expecting to be able to feel your assets and you will let them." We walked in and my wife said," Hello boys, here is Candy the sissy whore I told you about now checking her assets are free but blowjobs are $80 and well the full service is $80 an hour and if you want her the whole night that will be $400."
A man stepped forward and asked," What if I want her for say for a week?"
My wife smiled and said," I think we can arrange that for $2000 now for that price you can do anything except any scarring you and your friends can gangbang her."
The man took out a small bundle of cash and handed it to my gf.
She smiled and said," Well, you can take her home with you after the party but you can also take her first."
The man smiled and started taking off his pants and underwear and I saw a stiffening 8" by 21/2" cock and he shoved me on my knees and ordered my mouth open and then I started sucking his cock. Now, while I am sucking his cock what I didn't know was digital video cameras were filming everything. After his cock was completely hard my skimpy mini-skirt pulled up on my hips and my wife pulled down my panties.
Behind me, I heard him say." My what sexy cheeks she has I hope her hole is tight."
I felt this intrusion and I screamed in pain because I felt like I was being ripped apart but he laughed and kept pushing the intrusion further and further and laughed at my screams.
Meanwhile, my wife said," We all know what kind of a sissy you are and it is time for you to live that life."
I finally felt his balls against my smooth cheeks and he whispered in my ear," What a nice sissy cunt you have."
My hole adjusted to his cock then he started to thrust in and out slowly at first and I started to moan I couldn't believe it it felt so good. He fucked me for about an hour and I felt his cock buck violently about 4 times and flooding my hole
Next thing I knew I had a cock shoved into my hole and another cock shoved into my and both men fucking me at the same time at first I gagged but my gag reflex opened out of the way.
I spent the remaining night being fucked and feeling my hole being bred over and over and I am moaning like a bitch in heat knowing I would never live my life as a man again.
The next thing I knew the man grabbed me naked and took me to his car and drove me to his place.
There at his house, he took me out of his car and brought me into the house.
He said," Well, you know your marriage with your wife is over. Get used to it you will be a good sissy and If I can talk your wife into it I might buy you."
He jerked my panties down and started playing with my hole and cheeks and I involuntarily moaned.
He laughed and said," You are a sissy no man would moan like that when having their asses played with like that. "
He bent me over his couch and I heard his zipper and then I felt his cock and this time I pushed my hips towards him.
He fucked me ruthlessly for 2 hours and then he shoved his cock deep into my ass and then he shoved his cock deep into my ass and I felt his cock buck violently about 4 times flooding my hole once more. He kept his cock inside my hole until it softened and popped out.
He took me to bed and put me in lingeree and we climbed into bed. I heard him fall asleep immediatly but I stayed awake for another 30 minutes wondering what my life held for me and crying myself to sleep.