How to Make a Sissy

Once he has them on you need to exclaim over them. Grab his ass and tell him how hot they make his ass look. Caress all over them. Push your finger up towards his rosebud through the material, pull them out of the crack of his ass and slip your fingers inside the leg opening and caress his ass and entrance to his anus. Mouth his caged cock through the material. Tell him how hot it's making you and that you're going to need him to make you come again. Guide him into a 69 and, as he services you with his mouth, play with his knicker covered ass. Slide your hands inside and caress his ass and his caged cock. Work a finger toward his anus, touch and stroke the entrance to his anus. If he protests just go "Shhh! It's turning me on, can't you feel it?" and keep going. Let him bring you really close to orgasm then push him off, pull his panties down far enough to take the cock cage off and immediately lie on your back with him between your legs. Say "Fuck this is so hot! I want you to masturbate yourself over the top of the waistband of your knickers, whilst I make myself come. I need to feel your come splash on my pussy as I pop! Can you come with me? Come on my pussy as I orgasm?"

He will, of course, be keen to come.

Once he's shot his load take him by the back of the head and guide his head down to clean you up again. If he still resists say "I think watching and feeling you clean me up will make me come again. Please, baby, make me come again? You make me so horny! I need to pop again, please, baby?"

If he does it you need to come! Fake it if you have to! Then tell him over and over again how fucking hot it was, how good it felt and how you hope like hell he'll do it again.

If he doesn't want to use his tongue to clean you still it's important that you don't make a big deal of it. Just keep trying every couple of times and tell him how hot the thought of him doing that makes you until he does.

Don't forget to hand him his cage so he remembers to put it on.

1. Starting to teach him his role.

Make this part of your weekly routine but remember, it's vitally important it's not you that makes him come. He needs to learn that having you give him an orgasm will only be allowed when he's been a very good boy.

When he gets used to wearing the knickers as part of your weekly play sessions, on a day when he is out, remove all of his boy underwear and replace them with a selection of women's knickers. Have some frilly ones, some thongs, some boy cut briefs he can wear for work and any others you think will suit him. When he complains simply say "Your ass is so sexy in your knickers I want you to wear them all the time. It'll make me so horny at work knowing you're wearing some sexy knickers I chose for you I'll probably need you to fuck me as soon as you get home! Please, baby? It will make me happy!"

Silence now, is again your best friend. If he tries to refuse say "What's the big deal? Only you and I will know and it looks sexy and it turns me on. Don't you like turning me on?"

If you quietly but stubbornly insist, using the same techniques as before he will soon give in and agree to wear them.

Every time he 'gives in' you need to thank him and reward him for acquiescing to your needs. Let him have an extra orgasm or make him a really nice meal, something.

1. Training him to like ass play.

Now is the time to introduce more and more ass play when he's servicing your needs. Play with his butt, slide your fingers into the crevice of his butt. Get him used to you stroking and playing with his taint. Keep sliding your finger toward his anus until he allows you to touch and play with his rosebud. Wet your finger and use it to rim his anus. Slip a little bit of your finger in. Every time he protests tell him "Shhh it's turning me, and you on. I can tell by how your cock throbs every time I do it."

But remove your finger for a bit before returning to it again. Start to play with his balls as he masturbates for you. Stroke his taint as you handle his balls. Wet your finger and reach toward his rosebud and make the area as moist as you can. Slowly get your man used to having your fingers around his taint and anus and a finger probed a little into his butt. Obviously you will need to sit up to do this. Let him rub his cock on your breasts if he's letting you play with his taint and/or ass, but lean back away, so he can't, if he resists your probing fingers. Push him away if he tries to follow you with a curt "no". Reward him with contact with your breasts once he lets you start playing with his ass again.

Once he allows you to slip a little bit of your finger inside his ass as he masturbates tell him how horny doing that is making you, how slutty it makes you feel and how much you love doing that for him. He will eventually relax and enjoy the sensation. Once you can tell he is enjoying having his ass fingered (it might take a few sessions) wait until he reaches that point of no return and is starting to come and push as much of your finger into his ass as you can and hook your finger back towards his balls. Hopefully your finger will scrape across his prostate, if it does then then, trust me, he'll want you to do it over and over again. Push the mounds of your breasts firmly around his cock and let him come on them. Come if you can, pretend if you can't, and say "Fuck! I came just from doing that! Fuck doing that is so hot! You have to let me do that again! Oh, baby I came so hard!"

As usual, make him use his tongue to clean you up but guide his head between your legs again because he's made you so horny. Again, pretend if you have to, he needs to know that what you're doing to him you're doing not only for him but because it turns you on. Trust me, he loves the fact he makes you horny enough to come.

Getting him to do what you want is really a simple matter of rewarding him when he obeys and ignoring him when he won't but continuing to fan his sexual arousal.

1. How to enjoy anal sex.

If you're thinking you're going to want to try anal, or you've already experienced it, but it wasn't done properly, so it hurt, and you want to try again, this is the time to teach him how to service your ass. Lift your hips up and throw your legs over his shoulders. Guide his head lower until his tongue is licking your taint.

Don't do this unless you are scrupulously clean in that area and around your 'starfish'!

Use verbal encouragement as well as constant pressure on his head to encourage him to keep licking there and/or to go further towards your rosebud. Tell him how good it feels and how hot it's making you.

Remember, eventually, you're going to want to get him to the stage he willingly does this for your bulls (prepares your ass to take their dicks).

Make him tongue your ass and lick your taint and rosebud. Roll over onto your stomach, put a pillow under your hips, so your ass is raised. Then he'll be able to tongue you from your clit, across your vulva and perineum, and all the way to your rosebud. Every time his tongue hits your rosebud groan in appreciation. He'll soon get the hint to concentrate on there. Instruct him to hold your ass cheeks apart and tongue your rosebud and to push his tongue as far into your ass as he can. Have him 'fuck you in the ass with his tongue' shoving his tongue as deep as he can, withdrawing it, then repeating. You need to be very verbal about how good it feels. Reach between your legs and start to masturbate yourself. Make sure you show by your moans and thrusting hips how much you're loving what he's doing.

At this time he is going to try and fuck you, probably in the ass, but definitely in somewhere (he'll ask you to take the cage off so he can). It's extremely important you don't let him! No matter how turned on and horny you are you must resist! Fucking you in the ass is going to be something he never gets to do, it will be reserved for your bulls. His job is going to be to make sure your ass is ready to receive the 9in monster you're hoping to score with.

Tell him you're too scared to let him fuck your ass because every time you've tried it it hurt but that you want to lie on your stomach and finger yourself to orgasm as he rubs his cock along the crack of your ass between the cheeks. Remove the cage and have him tongue your whole crack until it's sopping wet with saliva then have him lie on you with his cock between your cheeks and let him hump you. Every time he tries to slip it into your ass or pussy, and he will try, tell him "no" curtly and that you're going to make him get off and put the cage on if he continues to try.

Tell him you want to feel him come on your ass as you orgasm (to help him, regularly squeeze your ass cheeks together around his cock) so he needs to wait until he feels and hears you starting to come. Once you've come, and he's shot his load, make sure you have him clean you up, but now, as he has been a very good boy, you need to reward him. I'll leave that up to you. You can let him fuck you, or give him a blow job, you choose. Definitely one of those two, though. But, as soon as he has come and cleaned you up, back into the cage he goes.

He'll be even keener to please you now as he knows when he does he will get his prize of actually fucking you or being blown.

1. Teaching him more of his role.

He now needs to get used to preparing your ass to receive your bull's cock. Ask him to buy you a series of butt plugs ranging from really small to as big as you think you might like to take. Say to him "I want you to be able to fuck me in the ass."

Be crude in this situation because he loves to think you're a 'dirty' girl

"But you're too big. Will you help stretch me?"

Hand him some lube, your vibrator and the smallest of the plugs, lie on your stomach, spread your legs and slide your hands down to your pussy and start to play with yourself. Ask him to tongue your clit and vulva and to make your taint and ass all wet and slippery. Ask him for the butt plug and to watch for a moment. Lasciviously suck it and make it as wet as you can make it (he'll love the show) then hand it back to him and tell him to be gentle. Have him rub it around your rosebud and to gently apply pressure to the entrance. Your 'starfish' will get dry fairly quickly so keep getting him to tongue the area as it does tell him to lube up the plug as well. When you're ready tell him to gently push the plug in.

He needs to be in his cage for this because, if he isn't, he's going to try and substitute his dick for the plug and if you're as turned on as you should be by now you'll probably let him!

As the plug slides into your ass it will probably hurt some (even when you're stretched, and used to taking cocks up there, as the head pops through your knot there is usually a stab of pain). Ask him to stop and clench down on the plug with your ass sphincter.

Similar to those Kegel exercises you were meant to do after having your children, remember? 

Then relax your sphincter and give a gentle push, as if you're trying to push the plug out, then relax and tell him to continue (repeat as necessary). Once it has popped through the knot (it will feel similar to when a man's cock head pops through) the part of the plug after the widest bit is quite narrow and will sit inside you comfortably. Give yourself time to get used to being 'filled up' while continuing to play with your pussy and clit. Use your imagination, if you have to, and pick someone you'd really like to have in your ass and fantasise it's him. Once the plug feels comfortable get him to tongue the cleft of your ass and gently pull back and push in on the plug. Make sure it doesn't slip past the knot until you are used to that feeling (clench down on it with your sphincter if it feels like it's going to).

You'll probably come to love that sudden intense feeling as the plug, or your bull's cock, pops through the knot but probably not immediately.

As your excitement rises tell him to increase the speed of his pushes and pulls. As you get close ask him to use the vibrator on your clit and pussy. Use your fingers to guide him because he probably won't know what he's doing. As you get to almost 'that' point tell him to turn the vibrator all the way up and push it firmly against the plug and slide a couple of fingers as deep into your pussy as he can. Continue to play with your clit, and ride the intense feelings as you feel the plug vibrate through the thin wall between your ass and the inside of your pussy.

Once you're satiated he needs to be rewarded again use whatever method seems appropriate to you (except for your ass, of course). Be extravagant with your praise. Tell him how good he is to you and that you just love how well he has looked after you since he put the cage on.

Always make him think it was his idea to be caged.

What an awesome lover he is and how much you love him and how you feel so much closer to him now he takes care of you first and so well!

Hand him his cage.

Repeat with the other plugs until you can comfortably take one the size of the cock you think you might like to take up there.

1. Continuing his feminisation.

As soon as you feel that your man is no longer even really thinking about wearing women's knickers, except when you're grabbing his ass and exclaiming how hot he looks, you can add some 'stay up' stockings and a butt plug (for him) into the mix.

After he has finished in the shower, and has shaven his genital area all clean, hand him a really brief thong and a pair of 'stay up' stockings. Don't make any fuss about it simply say "Can you wear these for me as well please, baby?"

He will obviously protest. You should reply something like "You have really sexy legs and they will look even hotter in a pair of stockings!"

He'll want to know why you want him in 'this shit'. Just say "Because you've been so good to me, I've been considering raising the kink level so you can start to have some of your fantasies fulfilled! But I don't think I can do it. I'm too nervous. So I thought we could play some role play sex games where we 'switch roles'. I want you to pretend to be a 'woman' so I can see if I can make love to you like that and get more comfortable with these games we've been playing together. If it goes well I'd like to see about finding a female lover for us both to play with. Please help me?"

How can he refuse?

Help him put the stockings on because he'll try to put them on like a pair of socks (he won't roll them up first) so you'll have to show him. As soon as they are both on burst out laughing and say "They look ridiculous with your hairy legs! Come into the shower and I'll shave your legs for you." Start to walk towards the shower as if it's a given he will follow you.

He'll raise the usual protests "what if the guys at work, or my mates, see it?" Point out that he works in an office (if he does) and wears long trousers all day so who is going to see? If he works in shorts point out that manscaping is a really big thing now and you thought it would be a thrill if he 'gave it a go' because you think he will look hot! And say that after he's done it, he can tell everyone at work that you fucked him senseless all afternoon and night (because you're going to) and they will all consider doing it too!

If he continues to object fold your arms under your breasts and give a really disappointed sigh "Why do you keep resisting me when every time we do something together like this our sex life gets better and I learn to love you a little more?" Take his hand again and insist he follows you to the shower.

Shave his legs smooth. Keep exclaiming how sexy his legs feel and look now they're getting smoother. Once you've finished lean back and say something like "Fuck you have sexy legs I can't wait to see you in the stockings!" At this point ask if he wants you to just go ahead and shave the rest of him because "in for a penny, in for a pound, right?"

Hopefully he will acquiesce, but it doesn't matter if he doesn't, because you'll get him there eventually.

Take him back to the bedroom insist on rubbing some moisturiser into his legs and tease him mercilessly. Stroke his dick, play with his balls, finger his ass and constantly croon about how fucking sexy his legs are and how you can't keep your hands off them. Rub some into his stomach, chest and back if he's let you shave him all over.

The object is to bring him as close as you can to orgasm but not let him over the edge. This is called edging and it's something you need him to be able to do for long period of times, as you'll see, in the following passages.

Help him back into the stockings. On the pretence of 'helping him' stroke his now smooth legs and keep telling him how much his 'sexy legs' are turning you on. Let him feel your pussy so he can feel your arousal. Hand him the thong that you've chosen for him (the thong needs to be big enough to cover his bulge).

You'll want him in his cock cage, and given you've just spent 30 minutes winding him up, he's going to be as hard as algebra so tell him you're just so horny you have to come now and you want him to come on your tits as you finger yourself to orgasm like, right now!

This is a time to fake it again if you can't quite get there. What you want is him coming as soon as possible and to be soft enough to fit back into his cage.

1. More feminisation.

Once he has finished and has you clean again tell him you want him to look as much like a girl as possible so you can pretend that you're going to be making out with another woman and the cage will help smooth the bump (it will, but only because it won't let him get hard) and get him to put it back on.

Have him climb up on the bed and lie on his back, get him to raise his hands above his head and hold onto the headboard, if you've got one, or the back of the mattress if you don't. Instruct him that if he lets go and touches you the session is over. Tell him he is to close his eyes and keep them closed.

This is, once again, getting him used to obeying you, and only wanting to satisfy you not just getting himself off. And helps move him towards taking the more subservient role you have in mind for him.

Now make love to him like you would like to have someone make love to you. Kiss the nape of his neck, blow gently into his ear, and nibble on his lobes, kiss him gently then passionately, softly lick the corner of his mouth, trail kisses down the centre of his chest and slowly circle into his nipples. Tease and nip and gently pull them with your teeth. Swirl your tongue around them and softly suck on them.

Around now you will need to remind him he must stay still, keep his eyes closed, and not to touch you no matter what!

The next thing is to start to talk to him like he was a woman. Tell him how sexy 'she' is. How you love her tiny tits and rock hard nipples. Kiss slowly down his stomach stroking and gently tweaking his nipples as you go. Trail kisses down to his thong then kiss where a woman's pussy would be. Use your tongue to lap at the area as if you were licking a pussy through her knickers.

Make sure you are using the feminine pronouns whilst talking to him in these situations as you want him to get to the point where he knows his role is to service cocks, not use his.

Tell 'her' you can feel how hard her clit is and how wet she is and how you can feel the heat of her arousal.

Move him a little more towards the centre of the bed so you can get into a 69 position.