How to Make a Sissy

Remind him again he must keep his hands off you but can lower them if they're getting uncomfortable.

Lower your pussy onto his mouth and ask 'her' to eat you out.

Explain to him he needs to pretend he's a woman and be gentler with his administrations, like a woman would be.

Sit on his face so he can't see what you're doing and reach into your night stand and bring out the massage oil and the smallest of your butt plugs. Lean forward into a classic 69 position and slide the thong strap out of his crack and apply a generous amount of oil to his ass and gently start to rub it into his rosebud. Start with your finger, as usual, and slip it into his ass. Mouth his cage through the thong and tell him you're giving her a little bit of finger while you're eating her 'pussy'. Slowly stretch his entrance until you can fit a second finger into him. Slowly insert the butt plug. He'll probably clench down and resist. Tell him to relax and enjoy as there's nothing like having your clit licked whilst there is a vibrator inside your pussy. Once you have the plug fully inserted, hopefully deep enough to be resting against his prostate, grab your vibrator and apply it to the base of the plug. This will send extremely pleasurable sensations across his prostate and colon, through the thin wall that separates his prostate from the base of his penis, and into his dick.

There's a pretty good chance, if you've done it right, he'll come, even though he is still soft in his cage. This is the start of training him to the point that the only way he can come is with a cock, preferably the cock of one of your bulls, in his ass and rubbing across his prostate.

Make him pleasure you until you are satiated. Let him take off his cage and remove the butt plug then reward him for being a 'really good boy' by letting him have vaginal sex with you. It won't take him long to come, properly, this time. Make sure he uses his tongue to clean you up.

Remember that you're going to make him clean your cum filled pussy after your bull has had you so get him used to it now.

Once you're clean, cuddle up with him and raise that fact that even though he tried really hard and you tried your best to imagine him as a woman it didn't really work as he is just too masculine dressed only in panties and stockings and wonder, out loud, if he would be prepared to go a few steps further to 'pretty' himself up so it would be more convincing? If he doesn't immediately say "yes" drop the subject. Make sure he is back in his cock cage and let him sleep.

About here you need to assess where your man is up to in his conversion from 'Alpha male' to 'subservient cocksucker'. You have him, at this point, exactly where you want him to be when your bull arrives. Basically naked, with nothing on but a tiny thong, is completely shaved down from head to toe, and is in a cock cage!

So let's look at some possibilities

He's raised little to no objections to this point. This would mean he's actually quite submissive and you can start to accelerate his transition.

He has willingly, or even better yet, enthusiastically gone along with all of the 'games' so far then you have a natural submissive and it will be quite easy to convert him to into a 'cocksucking submissive' as he, pretty much, already lives only to please you.

If your man is in the first category you can mix and match some of the below to get him more quickly to part 25 where he meets Abby. In this scenario (what you do is slightly different to the suggested actions below) you should ask him to dress in his thong, etc. before 'she' arrives but raise no objection if he doesn't want to.

If he is in the second category you can skip down to part (25l) where Abby comes over the second time.

Remember we're not trying to create a transgirl here (not sure if that's even possible). We're trying to create a cross, or more accurately, fetish dresser (n. One who dresses in the undergarments normally associated with the opposite sex to them for the purposes of sexual gratification).

There is a third category, of course, in which he resists you every step of the way. This means you're going to have to 'break him' into the role. The following instructs you how to go about breaking him down. It mainly involves stripping away his male persona and force feminising him completely so he will later be appreciative of the fact you've 'allowed' him to return to some semblance of masculinity.

1. More and more feminisation.

The next morning fuss over him and tell him how sexy he looks in his stockings and thong with his shaved legs. Rub your hands up and down his legs cooing over how smooth and wonderful they feel and look. Cup his cage as if you were cupping a woman's vagina and finger the entrance to his ass. Emphasise how womanly he looks from the waist down and how you wish he had a pussy so you could go down on it because you think you would be able to do it this morning as you're so horny.

Kneel down and mouth his cage to show you think you could.

Make him pleasure you with his hands and tongue. Explain to him the reason you have your eyes closed is because you're imagining that he is a woman servicing your pussy. Come hard and loud, even if you have to fake it. Get him into a 'scissor' position where your pussy is grinding against where his 'pussy' would be.

Remember you're actually grinding against his cock cage and his balls are in a fairly vulnerable position inside the cage so you need to be careful! Crushed balls is not a pleasurable feeling! You will want to push hard enough so that it causes him at least a little bit of discomfit occasionally, but not too much pain, just to remind him who's in charge!

Tell him you need to come again and start fingering yourself as you're scissoring with him. Have an orgasm (pretend if you need to).

Gasp to him that you had a sudden vision that he really was a woman and that he was fucking you with a large strapon and it popped you over the edge hard. Say "Fuck that vision was so fucking hot!" Bite your lip and look nervous. Start to say something and stop, blush if you can. Start again and stop then say, really softly, "I think it would be so hot if you bought a strapon, slightly bigger than your beautiful cock, dressed in your knickers, stockings and your cage, and then fucked me with it. I think I'd come so hard I'd have to give you a really good reward after. Would you do that for me? It might help me decide if I really can let a woman do that to me when she is making make love to me." Smile and say "Wouldn't that be a great show for you?" Look down and away as if embarrassed to be asking.

Silence is once again your best friend. Never beg and never berate him if he won't do it. Just use the withdrawal of affection and reward system we've discussed earlier in this post.

Give him time, if he hasn't bought one after a week, ask if he had thought anymore about getting a strapon as you really wanted to try it with him. That it makes your pussy throb every time you think about it, which is all the time. You need to make sure that you give him no relief during this time. Even if Saturday comes around, and he's all freshly shaved down there, tell him to put his cage back on and say that he may have a wank by himself before putting it back on if he wishes. Don't allow him access to the net though. Make him come up with his own fantasy to get off. If he does manage to come get him to tell you what he was fantasising about.

Hopefully it won't have been about your sister. 

There'll be a good chance it will be about you with another woman and him joining in. Tell him it's a possibility but that he needs to help you get over your fears first. And that having him shave off all hair below his eyebrows and dress like a woman then make love to you like he was one would certainly help ease some of your fears.

1. Teaching him his cock is not needed.

He will eventually buy the strapon and give it to you. Make sure you bring the fantasy to life as soon as possible after he has given the strapon to you. Get into the shower with him when it's time to for him to shave himself down and do it yourself. Use all of your skills to get him as excited as he can be without coming. It is, of course, impossible to get the cage on if he is fully hard so here's what you do: Tell him you want to raise the kink to a new level and take him into the bedroom. Using some of your pantyhose, tie him, spreadeagled, to the bed. Blindfold him with one of your scarves and stuff a recently worn pair of your knickers in his mouth

Recently worn is best, especially if you were aroused when you were wearing them, because the smell will drive him wild.

If you've made him horny enough in the shower he won't raise even one objection.

Go to the kitchen and get a damp cloth and a teaspoon. Wrap some ice inside the damp cloth and give it a few minutes so the cloth is really cold. Go to the bathroom and rinse your mouth with a little bit of toothpaste. By the time you get back to the bedroom he will have started to flag a little, but won't be soft. Take his cock in your hand and start to make him hard. As he reaches hardness take him in your mouth. Don't suck, just mouth him and gently breathe in an out with him in your mouth. The minty freshness of your breath will first cool and then warm his cock and bring him instantly close to orgasm.

Do not let him come!

As soon as you sense he is close hold the damp cold cloth against his balls and smack the eye of his penis with the teaspoon really hard! Unless he's a total sadist he will go soft immediately.

You want him horny but not hard.

Place the cock cage on him then proceed to make him as turned on as you possibly can again. Do the same as you did the night you first pretended he was a woman and made love to 'her'. Keep tormenting him until he is groaning in pain because his cock is throbbing against the limiting constraints of the cock cage. Ask him if he wants to come? Of course he will say yes. Then say "If you dress up as a woman again put the strapon on and gently make love to me until I'm satiated I'll take your cock cage off and let you fuck me for real, deal?"

He will instantly agree. Untie him, take the blindfold off and your knickers out of his mouth, and then hand him the stockings, thong and strap on. As he wrestles with the stockings, hand him a camisole top to wear as well.

Don't say anything just indicate he should put it on, too.

Once he has all of the gear on help him to put the strapon on and tighten up the straps. Position it so it's actually resting on his cock cage not his pelvic bone as it should be.

You'll want this to be a little uncomfortable for him so he won't want to do it too often. The goal is to get him used to the idea you're going to want a bigger cock than he has in you before too long and that he can't satisfy this urge by getting increasingly bigger strapons.

Once he is all done up lie back. You're going to do as little as possible so that everything is up to him. Tell him he needs to warm you up with lots of foreplay because 'that's what a woman would do and you want to experience that'.

He should be stroking and kissing and licking all of your erogenous zones before he's even going to go close to touching your breasts or pussy.

Once he has completed his tour of your erogenous zones get him to gently massage and stroke and lick your breasts until he can feel your arousal. Then use his tongue on your clitoris and vulva to drive you even higher and to dip his fingers inside your pussy, gently stretching your pussy with one, then two, then 3 fingers to prepare you for the larger sized 'cock' he's going to fuck you with.

When you're ready to be penetrated ask him to lube the 'cock' and to gently insert it into you.

You'll need to lube it as there is no precum to prepare the way and your own juices probably won't be enough.

Take your time, and make him take his, until you are used to the extra girth and length. When you're ready whisper huskily into his ear "Fuck me hard now you beautiful sexy girl!"

Make sure you push back at that 'cock' hard enough, from time to time, so that it hurts his balls.

Keep calling him by feminine pronouns. "Fuck me, darling girl. My god, you sexy bitch, you're making me so hot! Etc." so he believes you are fantasising about him being a woman. Come hard and loudly at least once, numerous times, if you can.

Once you're fully satisfied ask him to gently remove the strapon from your pussy and tell him to take it off. But ensure he remains in his female clothes including the thong and top.

Release him from his cage and get him hard as quickly as you can. Guide him inside of you then ask him to fuck you hard again. As he fucks you continue to call him by female pronouns. As soon as he comes, come too.

Time to pretend if you have to.

Drag him over so he's lying on his back and snuggle in as close as you can to him. Play gently with his cock. Stroke his stockinged legs and slide your hand inside his camisole and stroke his chest. Lavish praise on him. Tell him how good he was, how hard you came, how much you love him and how much you appreciate what he did for you. Call him your sex god and the best lover you've ever had.

It's called 'stroking his ego so he'll want to do you like this again.

Don't even make him clean you up or put on his cock cage. Tell him you want to fall asleep with his come running out of you to remind you how good a fuck he is.

1. Further feminisation.

In the morning he is going to be hard again and will want to fuck you because he will think things are returning to normal. Don't let him! Tell him you are too sore from last night (doesn't matter if you are or not) Send him off to get a warm wet facecloth. Wash yourself under the covers Say "because you don't want him to see he's hurt you by fucking you that hard and well," if he asks.

Then tell him you want him to come on your breasts.

Don't help him at all other than to let him straddle your torso as he wanks himself off. Once he has come, gather a little bit on your finger and make a real show of swallowing it. Then make him use his tongue to clean you off.

Make him clean his cock and groin area with the same washcloth you used and put his cage back on.

Tell him you feel like some Maccas for breakfast but don't let him take his female clothing off. Just allow him to put something on over the top so the fact he is wearing women's clothing is hidden and send him to get some.

When he returns with breakfast emphasise to him that you expect him to stay clean shaven from the eyebrows down now and that, except when he was wearing shorts where he could leave the stockings off, he was to wear the stockings, knickers and a camisole top all the time as it makes you so horny to think of him as your 'secret girl'.

Explain to him that if he did this he will get rewarded for making you happy.

Over the next few days you need to keep him in a constant state of arousal. As soon as he gets home make him strip off his male clothes and put them in the wash. Explain to him that you find him so sexy dressed 'enfemme' you want him to be like that all the time you're alone together. Give him time to get used to the idea that at home he is to openly be 'your girl' and when he is out of the home it makes you really horny thinking about how he is now 'your secret girl'.

1. Teaching him to appreciate others paying attention to you.

If he works in an office or in retail turn up at his work with the cage key, have him sneak you into the staff cubicles, undo your top and tell him you want him to come on your tits but only if he is still dressed enfemme. Make him show you he is. If he's stripped them off don't make a big fuss about it just let him know you're really disappointed and immediately leave. Give him the usual cold shoulder treatment until he promises to wear the clothes as you want.

If he's still wearing the items take off his cage and kneel down so he can shoot on your breasts. Guide his head down to clean you off but leave some and say you're going to leave your top undone enough so that people will notice his come on you as you leave his office and when you are walking around. Put his cage back on before you leave. If people you don't know notice give them a really big smile and lick your lips.

If he works in construction, or elsewhere outside, turn up at his work dressed as sexily as you can manage. Short skirt, tight see through top, black bra, make up just perfect and enough buttons undone so you're just about to pop out the top of your outfit. Swing your hips and toss your hair, smile and wave at all the boys, then march straight up to one.

Even if you've seen your husband pretend you haven't

Ask for your husband by name. Ask "Who's the boss?" And then ask that person (the boss) if your husband can take you to lunch. Smile wickedly and promise you won't keep him long. Of course your man will say that he can't get away so pout and lean in and ask quietly if he's still wearing his knickers and camisole top. Make him show you, but not obviously, probably when he walks you back to the car. Same as above, if he isn't wearing them just walk away. If he is tell him you're going to give him a reward when he gets home.

As you walk back to the car make sure you swing your hips and make eye contact with as many men as you can and flirt with your eyes and smile. If you catch them staring at your breasts or ass, smile and wet your lips with your tongue.

This is the start of getting him used to, and appreciative of, other men paying you attention.

When he gets home, if he has been a good boy, make sure you reward him by letting him come somewhere on you.

If he bitches about you turning up at work dressed like a slut look really hurt and say "I just wanted to do something nice for you and to show all your workmates you have a hot wife who really cares for you. Why wouldn't you want that?" If he fusses more say "Fine! I won't bother anymore, now do you want to come and have sex or do you just want to piss me off so I won't let you?"

Tell him that he can tell the boys what a hot fuck you are, if he wants, and that he can describe some of the things you have gotten up to. Tell him you think it would be hot to know some of his workmates and/or friends were lusting after her. Make him tell you which ones have said you were hot and remember their names.

1. Moving him more towards being your sissy is next.

Start to buy him some girlie outfits. Dresses, skirts, blouses, sexy nighties even matching bra and knicker sets. Make them as slutty as you can possibly find. Really short skirts a size or two too small so he will have to squeeze into them when he begins to wear them and his ass will hang out of the bottom. Tops that barely cover anything and will barely do up across his chest. Dresses that have a mile of cleavage and will leave the cheeks of his ass exposed.

Don't say anything just place them in his wardrobe. If he asks just shrug and say something like "Dunno, they looked sexy and I thought you might like them." Refuse to answer any more questions about them.

Start to expand on the amount of time you spend arousing and teasing him. Try to keep him right on the edge of coming for as long and as often as you can but make the times you allow him to service you then get some relief more and more sporadic. Other than insisting he wears his stockings, knickers and camisole all the time don't ask for anything more.