Ultimate Humiliation (part 6)
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 gave over a dozen blowjobs by appointments – the result of my humiliation events and Mary's emails. I had kind of settled into doing them and some of them were really nice.
What especially disturbed me was two anonymous emails that told me how hot I was dressed as a girl, and asking if I would be their girlfriend. A man sucking cock is humiliating enough, but to dress in women's clothing is even worse. I was terrified at having to dress again, especially to arouse men and bring them to climax.
Brad came by twice for blowjobs and repeatedly asked me if I would dress for him. He said that when he fucked me last Friday it was the hottest fuck he had ever had – much better than Mary. Mary would really be pissed at me if she knew I was a better fuck than she was, and who knows what she would do to me?
The part that troubled me the most was that I really WANTED to dress for Brad! When he kissed me I actually liked it. When he had finished on Friday I nearly promised him that we would find a way to make it happen. Now he has been pressing me to actually do it.
I wondered if I could do it just for Brad and nobody else – I didn't know if the guys who sent me the anonymous emails would make trouble for me if I resisted – so far I have given in to all demands, which has kept me out of further trouble, but it also got me deeper into the net of perversion that Mary has cast over me.
Mary wasn't done weaving the web she had trapped me in – she told me to arrange to take Friday off because she had something special in mind for me. She had a diabolical mind, and I really feared what she had in mind for me.
When Friday finally arrived Mary and Brad drove me to an upscale house across town. A pretty blond woman greeted us and invited us in. She was introduced as Linda and said she would be working with me today. Mary told me that I was to cooperate in every way or else.
I didn't need to know what "else" meant, so I just nodded. Linda led me into a bedroom and told me to undress, which I did. "What are you going to do to me?" I asked Linda.
Linda smiled and revealed, "I am going to make you into a woman every man will want."
My heart sank – it was getting worse and worse.
"Look," said Linda, "I know you are being punished and you don't want any part of this – but fighting me wont' help."
"Besides," she continued, "a lot of guys who are involuntarily feminized really grow to like it – many actually come back and thank me."
That is what scared me the most – already I was liking some aspects of just wearing women's clothing – would this be the end of my being a man?"
"Are you going to do anything surgical?" I asked, with trepidation.
"Don't worry!" Linda said, "you will still have all your parts – but you will look amazing hot!"
I was relieved to hear that as Linda led me into a pink bathroom and told me to get into a bubble bath. "Just soak and enjoy being a girl," Linda said, "afterward we'll shave you."
I soaked for awhile, not feeling the least bit femme. Linda came in and told me to get out of the tub and she helped dry me off. She led me into the bedroom where she had me lay face down on a massage table. Three people joined her and they rubbed cream on my skin and proceeded to shave me.
They didn't miss a spot. Linda spread my ass cheeks and told one of her helpers to be thorough – men didn't like a girl with a hairy crack!
Linda told me to roll onto my back and shaved the front of me – when they got to my pubic area they used an electric beard trimmer and cut my pubic hair short, and then shaved the hair into the shape of a heart.
Linda led me back into the bathroom and told me to rinse off. I did so, and then dried off. She led me to a full length mirror and was surprised at how nice my body looked – if not for the cock and flat chest, it could have been a woman's body.
"Tuck your cock between your legs," directed Linda, which I did.
Without the cock, I just saw a heart shaped patch that could easily be a pussy!
Linda's helpers approached me with several seamstress tapes and measured all parts of me. Soon they brought items of lingerie to me and I slipped them on. The black hose and a lacey black garter belt looked a lot like what I wore last Friday. They put a matching bra on me, with breast forms.
"For your body size, C size is just right," commented Linda.
They slipped black lace panties on me, which fit, except for my bulge. Linda led me back to the mirror. "Ignore the bulge," Linda said, "I'll show you how to hide it later."
I was amazed to see a woman's body in the mirror. My bulge grew just from looking at myself! I realized that every week Mary had changed my life in a way I could not go back, and this was simply more of the same.
Linda led me to a chair like they have in beauty shops and they worked on my face. They plucked my eyebrows and trimmed my nose hairs. Linda commented, "a guy can get by with some unruly nose hairs, but no girl would!"
"Now pay attention," Linda continued, "we are going to teach you how to make up your face – you won't remember all of it, but do your best. You will be back for a refresher, so after a couple of visits you'll have this down pat."
It began to dawn on me that this wasn't just a humiliation – it was a change in my life! I seemed to not have any option, so I just went with it. I thought of Brad, and realized that deep down I found being femme to be fascinating. Linda and most of her helpers stepped out, leaving me with only one – a young man. "I think you are warming up to this," he said, "aren't you?"
"No," I blurted out, "No way!"
He put his hand on my bulge, now straining at my panties. He massaged my bulge and I groaned. Next his mouth was on mine, tongue probing me. I relaxed and kissed him back.
"I thought so," he said, "there are a lot of men who love girls like you!"
He broke away as Linda and the others returned. They put shaving cream on my face and brought a mirror near and told me to pay attention. She explained that I needed to learn to do a 4-way shave: one pass each with the grain, one against the grain, and across in both directons. That would remove as much of the whiskers as possible. She explained that while most men shave in the morning, I should start shaving a few hours before my date in order to get the most time from the shave.
After drying my face, they showed me how to apply a good foundation that would help hide a five o'clock shadow as long as possible. Then a bit of color – nothing very heavy so I wouldn't look like a painted lady.
That was just great – I was going to BE a whore, but didn't want to LOOK like one!
Linda said my eyelashes were large for a man, so I wouldn't need to use artificial ones, but showed me how to put on mascara, eyeliner and eye shadow.
"You are already naturally pretty," said Linda, "so you want to put on just a hint of makeup – just enough to accept your features."
As I looked at the mirror I couldn't believe how my face had changed. Linda led me to another room where there were a variety of wigs on stands. She chose several and asked me which I liked the best. I chose a black shoulder length wig and Linda took me back into the other room. She showed me how to put the wig on, and how to brush it as I wore it.
One of her assistants brought in a rack of dresses and shoes. We chose a dress, which I slipped on. Linda chose a pair of shoes with two inch heels. "Eventually you will want higher and thinner heels," she said, " but for now you need to learn how to walk in these."
I put the shoes on and we spent the next hour practicing walking, sitting and learning a variety of feminine mannerisms. It was a lot for me to learn, but I was doing the best I could. They even instructed me in how to eat like a woman.
"You are nearly ready," Linda announced, "we just need to show you how to hide your bulge."
One of her assistants lifted my dress to the waist while another pulled my black panties down. Released from the panties my erection sprung loose.
"We have to start with you soft," said Linda, and asked one of her assistants to help out.
In full view of the mirror I saw the man who had kissed me take my balls into one hand while stroking me with the other hand. It was an incredible hot image in the mirror and soon I was cumming. The guy held a tissue to catch my cum and threw it out.
He told me to step out of the panties now at my ankles, and told me to spread my feet apart. I was now soft, and he wiped the last droplette of my cum off me. He tore off about eight inches of duct tape and taped my soft cock under me. He explained that I had to make sure to avoid my pubic hair because it would hurt upon removal.
I put the panties back on and the guy held my dress up while I looked in the mirror – there was no bulge at all!
Linda said I was now ready, and led me out to another room where Mary and Brad were kissing on the couch. They stood up and looked me over, smiling at the result of Linda's work.
"I've given Brad an assignment for tonight," Mary said, "he was reluctant, but now has agreed to be your dinner date tonight. Your name is Jennifer, and you will treat Brad as an appreciative lady should."
–––––––––––––––––––– To be continued ...
Feel free to contact me with your comments or requests. –Bill (oral_guy_2000@yahoo.com)
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