I was just coming home from work when he called and I was just stepping out of the pickup. .
He said," This is Carey and we met at the lounge and you said you could help me."
I acted like I forgot and said," Yeah, that is right I can help you only on one condition."
He asked," What?"
I said," That in these sessions you are to do whatever I say and do that to completion. If you have a problem with that than I can't help you, I am only doing this for your benefit."
He hesitated for a minute and than said," Deal"
Now I knew I had him but to really seal it I will have him sign an agreement.
I had set it for Friday evening and that would give me time to set up the atmosphere of my place jus t right. I worked on my place after work every evening and by Thursday evening I had my place set up just right. I had scented candles set up in strategic areas of the living room and had lights that were just right not too bright and not too dim.
I went to work Friday and when I got home I saw him in front of my home and saw he was a little more desperate than I thought he doesn't have to sign the agreement.
I said," Well, hi Carey, why don't you come on in."
I showed him to the couch and I quickly lit the candles and sat down in a chair in front of him.
He asked," Can you make me more manly or masculine?"
I said," Well, I don't know about that but I think when we are done you will be happier. You see we don't know how this will go but you will have to accept it no matter what path your road takes because when you do than you will have a happier life."
He said," Like what path?"
I said," I am going to pretend how you will end up."
After that he started talking and he told me how his girlfriend was berating him about how unmanly he was. Than he told me how when he was in shorts men, men who seemingly were straight were attracted to him.
I said," That seems interesting and how long has this been happening?"
He said," It has just started happening recently."
Well I saw the hour was coming to an end and I told him.
I said," This seems to require that we make this weekly. Now I want you when come if you aren't wearing shorts at least bring them with you and oh yes bring the shirt that you wore with the shorts."
He asked," Why?"
I said," So maybe I can see why these men might be attracted to you. Remember I am doing this for your benefit."
Than I said," Wait a minute I think I might have some shorts that just might fit.
I went in and found some shorts that looked about that same size and a shirt that matches.
I said," Put these on and I will be back in 10 minutes."
I left the room and read a little bit and looked at my cellphone and saw 10 minutes had passed. I went in and told him to come out to the living-room. After he came out to the living room I walked around him and stepped back about 5'0" .
I said," Take off the shirt."
I looked at him I couldn't believe how much like a girl he looked from behind. His shoulders were soft like a woman's and he also had a little bit of a flair at his hips and he had a bubble butt like a girl.
I told him to sit down on the couch and I took a chair across from him.
I took a deep breath and said," I think I have a solution for your problem but I think you will find this difficult to handle at the moment. Now, if you heed my advice I know you will find you will be happier as a result."
He said," What?"
I said," Make the transistion, to stop living your life as a man."
He looked at me opened mouth and said," You mean being a cross-dresser?"
I said," No cross-dressers are men who dress as women. You are to transistion yourself to a woman. You will be put on estrogen and than you on your option save up money for surgary to fully change your sex. Now you can choose to not do what I suggest but I know you will be far more unhappier trying to live your life as a man."
He said," Do you know what you are asking of me? You are asking me to give up my whole identity."
I asked," How well has that identity worked for you? You trying to live your life as a man? Now you are to lower those shorts and underwear and I want you to get your penis hard for me."
He looked at me in shock but than did what I told him.
After he got his cock hard I took my tape measure and measured his cock. I looked at it and I was shocked it was thin I estimated maybe an inch thick and 4" long and I shook my head.
He asked," What?"
I said," My dick is about average at about 7" and 2 1/2" thick. Your dick is 4" and maybe 1" thick. That means your dick is about 3" below normal length wise and maybe 1 1/2" below normal in thickness. This is like a larger women's clit."
He hung his head in shame with tears in his eyes.
I said," This looks disastrious at this moment but if you step back than you can deal with it. That is you would make a better woman than a man."
That brought on louder cries from Carey. I sat back as he cried to let him bring himself back into composure.
After about 20 minutes he was able to bring himself back to composure.
He said," You are telling me that I could choose to not do this but that more than likely I will be unhappy but if I choose to totally change who I am I will likely be more happy. If I decide to go ahead and change my sex what then?"
I said," i have good news on that front. I will be there along with female friends who will help you through the step by step process."
He took a deep breath and asked," Can I take some time to think about it?"
I said," Sure, now if you want to talk to some of my female friends. Also, let me ask do you think like a man or a woman? Do you think with a little more emotion than a man? Don't answer me now I want you to think through those questions than those answers on what to do will come."
Oh no don't get this confused this is one way to guide your future sissy to the conclusion you want. It may just be over-night or it may take a month but you have already made the decision you are just letting him/her think that they came upon this conclusion on their own. Remember your guidance is done sublimimily almost. You want this sissy to be led without thinking they are being led.
He left my house with almost a confused look on his face and that is just what I wanted. If he had an expression that is not confused that means his mind is made up and more than likely you have lost him. This does not always works but that is part of what makes the hunt and " courtship" fun.
I closed the door and thought this is going quicker than I thought. I have already measured his cock which meant he had already had some doubt of who he was. Of course I knew one of the rewards was that I knew I was going to fuck her and yes I called him a her. I had my condoms ready for that. After fucking her I was going to suggest that she didn't get fucked again for at least 4 months so her boi-cunt could get tight again for her man. Oh yes, I am going to be with her when she finds her man because I want her to find that right man. If she has her surgary she can definetly have a straight man. This is all going according to plan now I will have my female friends "accidently" bump into her so they can talk. Yes women talking to a sissy can really gently coax him/her to the direction I want her to go.
I know she will go the way I want her to go now all it takes is patience. If this was fishing you don't want to reel in too fast or that fish will get away. All you want to do is set the hook.
You while I am waiting for her to go the direction I want her to go I will go back to the club to find my next potential sissy. Some of you are thinking the next victim. She would be my next victim if the happiness was all one way but she will be just as happy when she excepts who she really is.
Now it is time for me to go to bed and get ready to go hunting again tommorrow night.