Ultimate Humiliation (part 5)
I was on top of the world when my wife caught me in an affair and my life became one humiliation after another. I hope you enjoy this work of fiction.
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Throughout the week I found that nearly everyone replied to the emails Mary sent. Some declined but seven of the ten said they wanted more. While I had no choice in the matter, I felt really conflicted about all this. I was outraged at what I had been forced to do, but was really enjoying cocksucking. Now that I had been "outed" to so many people I knew, it could not be undone, so there was no point in denying it. My wife thought I hated the cocksucking – in a perverse way, my enjoyment of it was my way of getting back at her.
On Friday night I reported to Mary for my weekly humiliation event. She told me that it would be the last time I would be anonymously sucking off guys I knew, but it would be the most humiliating of all.
"You won't be naked tonight," said Mary, "I have something very sexy for you to wear."
By now I knew that was best to remain silent – nothing I could say would help me out, and I could make it worse for myself.
Mary guided me to put on a black garter belt and black hose. Then she put the bra on me. There were breast forms that gave me some shape.
Next she put a wig on me – it was brown and shoulder length. She told me I looked pretty and my shame grew as she brushed my hair. The final touch of my humiliation was red lipstick, after which she took me to a mirror and I looked in horror – I looked like a complete sissy!
"I would put panties on you, but I want everyone to see how aroused you are," she said, "so like last week you will stroke yourself and cum after your last blowjob."
My humiliation was at its maximum as I stood there, but I knew that the worst was yet to come.
Mary led me to the living room and placed me on my knees. She led tonight's men in and I heard a combination of responses – some laughter, some "oohs" and "ahhs". The first guy approached and said, "that's a pretty mouth, sissy bitch."
I sucked him as tears formed in my eyes. He came and I swallowed and pulled out. Mary stepped forward and said, "just a moment, a girl likes to look her very best." She told me to lick the cum off my lips and then wiped my lips with a tissue and refreshed my lipstick.
I continued sucking, getting my lipstick refreshed between each blowjob. Some guys seemed oddly affectionate, talking softly to me, "I didn't know you were like this – I want to be with you."
That was a bit much for me, and the tears in my eyes streamed down my cheeks. He said, "poor dear – I promise that I'll treat my girl with tenderness."
I couldn't really understand how I felt about this – in the brutality of Mary's humiliation of me was someone who expressed compassion for me – but as a woman!
I tried to do my very best in sucking this man, and felt especially good about pleasing him.
After refreshing my lipstick I sucked the next guy. This continued until the last guy. As I did last week, I held him in my mouth after he came, and stroked myself to climax. I swallowed his cum and released him, then swallowed my own cum.
Mary led the men out and returned to me. "Stand up," she commanded, which I did. She told me I really messed up my lipstick while sucking and wiped the smudged lipstick from my face and put new lipstick on me.
"There are two men who want to see you," she said. She led one in and he approached me, still naked and wearing the ski mask.
He took me into his arms and grabbed my ass as he kissed me, driving his tongue deep into my mouth. It was disgusting to kiss a man, but I endured. He ran his hands all over me, caressing my cock and balls. "Will you be my girlfriend?" he asked.
"I'll think about it," was all I could think to say. He said he would be in touch, and left.
Mary led the second guy in, who also embraced me and kissed me deeply. "You are the kind of girl I like," he said. As he caressed me he slipped a finger between my ass cheeks and pressed it into my hole. He wiggled it around as he worked it in and I was surprised at how good it felt!
He brought his mouth to my nipples and sucked. I had no idea a man's nipples could feel as good as he was making me feel. Suddenly he released me and I felt a bit of disappointment.
Mary led him out, and returned, asking, "How did you like that?"
I lied and said, "It makes me want to puke!"
"Maybe for now," she said, "but we'll see."
Brad had been watching the entire time, fully erect the entire time.
Brad took me into the bedroom and whispered to me, "You look really hot – if Mary wasn't here I'd be kissing you as well."
I wished he would, but had to pretend I didn't want it.
Mary came in and said, "Bend over onto the bed – Brad is going to claim your virginity and give you a fuck you won't forget!"
She ordered Brad to force himself into me roughly, and without lube.
As he positioned me he whispered in my ear, "pretend it really hurts."
He pressed his cock head to me and pushed gently. "It hurts – oh please don't do this to me!" I said.
Mary said, "good, I want you to remember this well."
"I can't get in without lube," said Brad.
"Ok, use just a little – I want my sissy husband to feel every bit of your entry."
Brad must have not let Mary see the amount of lube, because he used quite a bit, and gently pressed a couple of fingers into me before pulling them out. He pressed his cock head to my hole and gently eased into me – it really felt wonderful.
Putting on a good show for Mary, he said, "I'm going to rip you open, bitch!" and the pushed in all the way. Since he had the head already in me, the thrust caused me no pain, but was felt great, and I played along and yelled out, "damn! please, no more!"
"Keep that up and I'll show you some real pain," said Mary, "bury your face in that pillow and cry all you want, sissy, but I better not hear any more yelling."
I did bury my face in the pillow to put on a good show, but loved the fucking I was getting from Brad. He fucked me for only a few more minutes before cumming, and I pretended to endure while I actually enjoyed every moment of it!
Brad collapsed on me and I found that I liked the feeling of his body pressed against me. Mary left and told us to clean up. After she left I thanked Brad for his kindness and told him I really enjoyed the fucking.
He pressed his mouth to mine and I welcomed his kiss, sharing my tongue with him. I was surprised at how my feeling about kissing men had changed so quickly.
Brad and I cleaned up, and he said he wanted to see me as a girl, but didn't want Mary to know. I told him that we would find a way.
–––––––––––––––––––– To be continued ...
Feel free to contact me with your comments or requests. –Bill (oral_guy_2000@yahoo.com)
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