The first face to face meeting
Ok this is make or break!
If this goes well, then (s)he is yours! If this goes badly then all that hard work has been undone (probably by rushing this meeting, (or it was never to be)).
Remember it is a much bigger step for him to meet you than it is for you to meet him. The fact he is prepared to do this is a huge step for some transvestites - (particularly the shy type - and remember these are the most likely to become controllable 'girls').
Ideally the idea to meet should have come from him. If you have forced the matter, then it may seem like you have won the battle, but you could easily lose the war, as his mental stage at the time of the first meeting is very important. If he is scared, frightened, & wondering why he is there you will have a job on your hands.
This meeting should be spectacular and make him very willing to return (afterall that is the idea!).
This is a difficult question, some boys will be happier meeting you at their home, others will be willing to travel (maybe not in drag - at first!), or others still may prefer a neutral place to meet (A TV club or even at first a normal hotel room. Be sensitive about this, you are turning up as a presentable male - he is hoping to look as feminine as possible (and early on in their training this is not always very convincing!)
Plan the evening:
This is again very important, don't just chance it to luck (or expect that you will think of something on the evening) - you won't! and you will end up trying to fuck her (which you may well do, but don't expect it on the first meeting - this is an important time for you to build a bridge of trust & control with her - there will be plenty of time later to empty your balls into her willing & aching arse IF YOU GET THIS FIRST MEETING RIGHT.
Ok so back to the plan. My recommendation is to take control the moment he enters. You should already know a great deal about him - this is useful information & you should have milked it from him during phase 2.
(If he is visiting you):
Keep the lighting low - if you don't have dimmers use candles or side lamps. This will add a sense of occasion as well as making his inital poor attempts at makeup and look good. He will feel happier (bright light looks like an interrogation! and at this stage he will have much to hide!). Choose the music wisely (I tend to play classical music for this as there are no lyrics - again choose the music to help set the scene. Do not have the television on! (although you may watch a porn movie later leave this till then - it will distract you). Don't be drunk! (although a little alcohol can relax both of you). If you have a dog keep it away for him (locked in another room!) - and remember to be well groomed, clean & dressed appropiately.
Now the scene is set. He arrives. These first few minutes are vital. Make him feel relaxed, so don't make him do a twirl for you. He will probably be very nervious (likely to refuse a glass of wine - but offer anyway). Even if he looks horrendious don't say it (you can always never invite him back & make the meeting short!) Make a few comments about how glad you are he could make it, and how he looks great in a dress. maybe offer him the bathroom to freshen up in. (If he is not in drag invite him in, have a chat and tell him how much better he would look in a dress and invite him to change (in private).
Keep the conversation about him and his femininity: e.g.:-
<Master> "So tell me, do you wear panties all of the time now?"
<boy> "Oh yes sir, they are so much more comfortable than my old underwear, I have 13 pairs now."
<Master> "That is wonderful to hear. I can imagine that silks and laces must feel so nice down there."
<boy> giggle - "yes they do."
<Master> "And you you have 13 matching bras too?"
<boy> "yes - I love wearing a bra."
<Master> "I bet you do, its just a shame you don't yet have breasts to fill them - do you sometimes wish you had breasts?"
Remember he may never have been able to talk about his dressing before to another human face to face. Let it all flow - have many questions ready - do not let the conversation dry up. Let him relax. (This should take some time - hopefull time will fly but at leat half an hour of friendly discussion about his dressing is needed).
Now if he has relaxed you can move on to the next step.
This is where you tell him that you would like to help him:- e.g.
<Master> "Well boy, it is pretty clear to me that you were born the wrong sex. Just looking at you & chatting with you for the past half hours has shown me that you make a much better girl than you do boy, & I would like to help you go as far down that path as you want to go. Would you like my help?"
<boy> -pause- "yes"
<Master> "Yes Master"!
<boy> "Yes Master"
<Master> "Tell me in your own words what you want"
<boy> "I want my Master to help turn me into a girl"
<Master> "Well said - I want to hear you say that often".
Closing the Deal:
Once he has accepted your offer of help there is a number of things you could do. I like the idea of a contract between you. Take him through to a room with a contract written out - essentially it must be gushing lanugage about his rejection of his male life and willingness to accept a female one, with references to his expected behavior (supply no pen). Make him read it aloud, and then tell him that if he wishes he may take it away with him, but if he ever wants to return he must come back with it signed (that gives him a get out clause & time to think if he needs it). He may well wish to sign it then & there - this is a great!
Do not allow the signing to be a simple signature, I would make a big thing of it. I would record it (maybe on webcam or video or audio) possibly make him strip naked to sign it (or at least to his panties) the read it aloud and sign it before dressing as a woman.
Whatever else happens between you two this first evening - DO NOT LET HIM CUM! Being starved of orgasm will keep him keen and the post orgasm glow for many transvestites is a time of guilt & gloom! YOU HAVE BEEN WARNED!
Before he leaves give him a pair of panties, tell him that he must be wearing when he returns next time & that you will check for compliance.
Mind Games & Hypnosis
If you have already reached this position things are going well. This stage and the following two stages overlap considerably, and by the time they are finished he will (correction) she will be a beautiful, happy, obedient, adoring, homosexual, transgendered, fuck toy. - which is just what you want her to be.
This should basically start from the second or third meeting, there is a definite change of pace here. The first meeting was all about making sure that first impressions were right, and that you two are compatible. Now you can build on that meeting - and begin to mould him into what you want. Soon the boot will be on the other foot & (s)he will be very keen to please you!
How to Turn Him Gay
Ok this can be fun. As long as he is not completely heterosexual (and if he has reached this stage he isn't) you can have a lot of fun helping him expand his sexual horizons.
A Scoring System:
It is important that you are always aware of how turned on your boy is. I say this because during this stage (and to a lesser extent stage 4), you are going to get him to subconsciously associate certain behaviors & actions with sexual excitement. I suggest a scale between 1 & 10. So a number 1 is not turned on at all (e.g. on the phone to your grandfather), and a number 10 is that the boy is actually ejaculating or at the point of no return at that moment. You do not wish for you boy to actually achieve a number 10 very often as there is a distinct change in attitude & lack of concentration post-orgasm in most transvestites. This way you can tell him to call you and tell you if he ever reaches a 9, so you can keep him hot & horny (6-8) safe in the knowledge that he is not about to spray spunk everywhere.
The following is something that my Master did to me and it seemed to work very well. I would encourage you to try it.
People can have fetishes about almost anything, but one common denominator for all fetishes is that an action or object is linked with sexual arousal. The treatment I call "The Chair" is a very good way to start to introduce him to three important concepts:
· He finds men sexually attractive.
· He needs deep feminization.
· His anus is a source of sexual pleasure.
You will need a cheap chair which will support his weight, even when a hole has been added to the chair to allow access to his behind. I used a canvas chair for this with a hole cut out in the middle, which I then reinforced to prevent fraying or tearing. A foldable canvas chair is also easy to hide away when it is not in use.
He should sit on this chair dressed in lingerie, but without panties.
He should then be restrained in the chair, so he is comfortable, but unable to masturbate himself (I used to handcuff his hands behind his back).
Then insert a heavily lubricated vibrating butt plug into his behind:-
The important thing is that the plug should be securely in him, plugs with grooves to hold them in place are better for that in my experience, however a vibrating cock-ring may also be very useful to keep him aroused.
I would then put his cock into a condom. The purpose of this is to prevent any damage to the carpet if he should ejaculate during his treatment - although for the treatment to work best he should not be allowed to ejaculate. (Mine ejaculated in the chair on the 5th or 6th session and the stains are still visible - so remember that condom). A vibrating cock ring may also be useful at this stage to keep him erect throughout the treatment. A few gentle pumps on his cock from time to time should keep him excited.
Now comes the trick. I used to make my boy watch Gay porn while in this state, so he learned to associate constant sexual excitement with men sucking & fucking each other. This did work although not as quickly as I had hoped.
Another slight modification or option: In your wonderful chair training...the Master may wish to first insert his finger in the sissy's bottom before the buttplug. This serves as a sweet preview of the hole his cock will soon enjoy, but more importantly, the Master can play an interesting tactic. Upon some deliberate exploration of the sissy's anus, the Master can tell to the boy that his Prostate Gland seems to be ABNORMALLY enlarged, further explaining that he once read in a medical study, that a high percentage of gay men, and almost all transgendered had this similar condition. This is sure go get the little one thinking!
My suggestion is to choose a few gay / shemale videos. Watch them and then record your own message to him on a separate tape for each film. This way you can put the right thoughts into his head all the way through. It is best that he hears them through large head phones & quite loud, this way your voice is in his head.
e.g. So while watching a shemale porn movie:
Doesn't She look wonderful. Soon you will look that good too. That is something you want very dearly. Look how happy she is holding her friend's cock. It feels wonderful - hard cocks make her excited - just as they make you excited, you have so much in common with her. I bet you want her to suck that cock - thats what you would do.
And there she goes, and look how much she is enjoying sucking that cock. Its what girls like you do. Repeat after me "I love to suck cock"... keep saying it "I love to suck cock"...
Doesn't she look wonderful. What lovely breasts! You want to be like her. In fact you are dressed just like her now - all you need is a nice pair of breasts, and if you ask me nicely later we might be able to do something. I would love to hear you ask for breasts...you would look wonderful with them
OHHH YES! this is what you want. I bet that feels wonderful for her. She is so lucky. I bet you wish that was you...look how happy she is - I bet you wish you could be that happy too...and he is happy too, this is the best way to please a man when you are a girl like you or her
Look at the sheer pleasure on her face, that cock feels so good inside her. Your dildo feels good inside you doesn't it..but a cock feels so much better. Imagine that your dildo was actually a cock - how wonderful it would feel....
The vibrator should remain on throughout the session, if you are in the room with him and have a remote control, you could vary the speed at the correct time throughout the movie. I just left it on full, and popped back into the room every 15 minutes to change his batteries (I used rechargeables).
This will obviously not work on the first viewing, but eventually over a few months, and twinned with other treatments this will turn him into what you want.
Fill him with Female Hormones
This section is optional and is only for those masters who want their sissy boys to really become girls.
First of all learn a little about hormones, there is a very well researched article here http://www.sissify.com/juice/ it is all under the title of "Girl Juice", & that is what recommend you call it when you start him on it.
Two type of hormones:
Or more correctly two strengths of hormones. There are medical strength ones - these are really the ones which work! and there are ones which can be purchased over the counter (or by mail) usually from specialist stock. The OTC ones can be quite expensive so shop around if you intend to go for the slow approach.
I recommend looking at http://www.transformation.co.uk/transform.html for quick and easy purchase of OTC hormones. These are quite slow acting! but fulfilled my requirements for getting my boy used to the concept of taking them. He should definitely know what they are, so he can voice any objections, but there is a very good chance if you time the suggestion properly that he will agree that it is in his best interest to take them. The slow acting nature of the OTC ones here is useful as he knows that there will be no noticeable changes for some time, but this is the thin edge of the wedge, soon you will have him using more & eventually visiting his doctor and presenting himself as a transgendered person, where the proper treatment & medical monitoring can begin.
A quick glance through the Transformation web site will show you the dazzling array of feminizing products they stock. I suggest you purchase only one of these (he can purchase more later), you can then give it to him as a gift. Unless he is dead against taking them (which you must respect), the pressure of them being a gift should be enough to give him his first taste of 'girl juice'.