The following day you drove Ashley to the airport, on the way not much was said about the previous evening until, "Are you mad at me Ross"?
"Yes I am, there was no need for you to do what you did, you totally humiliated me. Not to mention Pete walking in on us like that, I don't think he'll ever look me in the face again".
"But you got aroused when Jenny was looking at you and stroking you, so you couldn't have been too humiliated. I told her about your cross dressing a long time ago, however it wasn't until you accidentally left your laptop on your NBN site with your pics on display that I knew how deeply you were into it. Then I saw the emails to this Paula and I realized something has to be done. I often complained that I wanted the man I married, but I now accept you are still that man but you have other peculiarities, for want of a better word; and that I must learn to live with them, I do love you Ross and I do not want this to break us up. It was unfortunate that Pete found out the way he did. Jenny on the other hand finds it exciting and would love Pete to wear her underwear".
"So where do we go from here honey"?
"Once you see my plane depart, open that envelope I gave you, then you will have a choice to make, I hope that what I have outlined in it will ensure our happiness". She laid her hand on your thigh and leant over to kiss you on the cheek.
"Are you and Jenny lovers"?
Ashley looked at you, "No, we have had a couple of nights together and enjoyed making love but to be honest it is not something I could do full time with a woman. In all we have only done it four times in two years. When we discussed having a foursome, Jenny and I were considering doing each other then, just for your kinky pleasure. Would you like to watch us"?
You nodded, "It had occured to me".
She laughed, "Perhaps we can arrange that, I know Jenny would love to have you watch. To be honest I'd love to watch you and Jenny fucking. We need to get Pete on board for a foursome, I want to fuck him as well".
Later as you watched her plane disappear into the clouds, you opened the envelope. There was a simple note in it.
"Go to this address this afternoon and you will know what you have to do, you have my full support, this is why I have arranged this for you. oxoxoxoxoxo. I stress Jasmine you have my full support in everything that happens. I have packed a bag for you, it is in the trunk, take it in with you". The address was in Pacific Heights an upmarket suburb of San Francisco.
As it was close to midday you had a quick meal at the airport before driving to Pacific Heights, having checked to see if the bag was in the trunk, opening it to find some of your lingerie and dresses in it.
When you rang to bell you were met by a very attractive woman possibly in her early forties, extremely well dressed and made up.
"Hello I am Jasmine, I have a note from my wife to come here..".
"Jasmine I believe it is, you have your things", she said looking at the bag in your hand. "Come in Jasmine, has your wife told you what we do here"?
You shook your head, somewhat stunned that she was calling you Jasmine.
"Sit down darling while I explain. My name is Miranda. This house has a couple of functions. The first is that we feminize men. We take men who want to become or look like women and teach them how to do it properly. You will be taught how to do your make up, how to walk gracefully in heels, how to dress with class, how to talk like a woman, how to sit like a woman. This will take two weeks, you are to come here at 1:00 pm each day for the next fourteen days, for four hours each day. At the end of the fourteen days Jasmine I guarantee you will be able to pass as a woman in the streets".
"What is the second function"?
"Ah, we run an escort service. We supply "Ladies" to very high paying customers, customers who insist on discretion. We supply Transvestites, Transgenders and Pretty Boys to a growing demand of clientele. As well as girls with cocks we also supply girls without cocks, or women as they are called. They receive half of the payments from the client for their services, the other half come to me. Of course if you do not want to do that, sell yourself; then that is fine, however you must pay for the cost of your feminization which is ten thousand dollars. Your wife has signed a contract for your feminization, so how you pay me is up to yourself. You can pay me the money, or you can work it off as an escort".
She handed you a form that had your wife's signature at the bottom. Also on the form written and signed by your wife were the words, "Jasmine darling I know what you want to do at this point, you have my full support if you go down the path of prostitution".
You were stunned, not only had Ashley arranged for you to be feminized, but had also encouraged you to prostitute yourself. You looked at it for a couple of minutes, then Miranda handed you a pen. "It requires your signature if you want to join my escort service. I have to say looking at you, I can turn you into an incredibly attactive Transvestite. You will have no problems with customers".
You had often fantasized what it would be like to be on the streets selling yourself, but you knew that was never going to happen. You had often written with Paula how much you would love to suck cock and be fucked, preferably by other Trannies. Now you had the opportunity to make it a reality. And with your wife's blessing.
You signed the contract.
"Thank you Jasmine, now take your clothes off and put on some lingerie and this dress, I want to see what you have, and how much work I have ahead of me". Miranda watched you as you stripped naked in front of her, then you put on a matching satin panty/bra and garter belt set. Then she watched as you rolled on stockings and somewhat awkwardly clipped them to the garter straps. You pulled on the dress before stepping into the four inch heels. There was a wig in the bag and you put that on.
You stood self-conscious as Miranda looked at you, telling you to turn around, and then to walk around the room.
"Take the dress off Jasmine". You did so, she took it off you and ripped it up. "You may as well wear a sack than that thing. Now walk around the room again".
You did so.
"Take the bra and panties off and walk around again".
You hesitated.
"Jasmine if you are to become a whore, you must not hesitate when a customer tells you to do something, do you understand"?
You stripped off and walked around again, your cock swing freely.
"Come here, turn around and bend over".
You did so, went to her facing away and bent at the hips.
"Grab your ankles".
You reached down and grabbed hold of your ankles, knowing that your anus was fully exposed to her. Still she grabbed your buttocks and pulled them apart further, examining your anus. Your cock was now fully rigid at this humiliation.
Miranda put on a rubber glove, took some lubricant and applied it to your anus, probing it with one then two fingers.
"You have a nice cunt Jasmine, tight and not damaged. Customers will like that. You will always call it your cunt darling because from now on that is what it is. It will make a lot of money for you. Make sure it is always clean, and you are always ready for full penetration. Now get dressed".
You put on the clothes you came in, once dressed Miranda said, "Your training begins tomorrow. At the end of the training in two weeks I will be assigning you to clients. You probably will only have one per week as you have another life with your wife. Sometimes you will have two in a week, in each case you will be given 24 hours notice.
Don't be afraid Jasmine, my training will ensure you are totally feminized and capable of performing what is required of you, and my clientele are rich and sometimes famous. You will do very well darling, but we both have to work at it".
As you drove home you tried to absorb what had happened.
Your wife signed you up to be feminized.
Your wife signed you up to be a Transvestite prostitute.
It starts tomorrow.
You could not sleep that night as you lay in your nightie in bed. You were excited at the prospect of having a strange woman taking you and making you a woman, however the idea of having to have sex with God knows who was frightening. In the past you thought about what it would be like to be a whore, now that the reality of you becoming one and you would be used like a piece of meat for money suddenly became a bit overwhelming. You thought of going to Miranda tomorrow and pay her cash for the training, then it occurred to you that Ashley must have also thought this through and decided that this path was the best way for you to both go on in your relationship.
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