How to Make a Sissy

Note: An awful lot of crossdressers still identify as 'straight' and won't want anything to do with a male cock. Another lot more are 'transbian' and only want to have sex with women and/or other crossdressers/transgirls. You're looking for one of the latter.

Another note: If you are female, and you're prepared to date and have sex with crossdressing males and transgirls, and especially if you want to be the dominant partner, you will have a queue of 'girls' a 1000 miles long to choose from!

See if 'she' would like to come over for a chat. Emphasise it will only be chat the first time. If you're fairly sure she's the right one send her for an STI test and email you the results once they're through.

For obvious reasons.

Preferably you want one who wants to 'get dressed up' at your place after he has got there.

Do this from your account without your trainee sissyboi's knowledge.

Once you're sure you've found someone that will actually turn up show him/her to your trainee and make him admit that he thinks 'she' is quite sexy... for a guy'. And say you've invited 'her' over for a chat so he can see that being a 'secret girl' is actually quite common. Reassure him that he can wear his 'boy's clothes' for the meet, if he would prefer, and that you're going to take his cock cage off for the night.

I refer you back to the bold text above. If he's in the first category this is where you join back in. But you're being a lot more insistent he's got his stockings, thong, bra and camisole on (underneath his boy's clothes, is fine, also).

Make sure he knows that 'she' is going to dress herself 'enfemme' after she gets here and that it is definitely only for a chat and absolutely nothing else!

When Abby arrives sit her down for a chat and get her to talk about 'dressing as a girl' and how good it makes her feel and how horny it makes her.

Once you are all comfortable send Abby off to your bedroom to get changed.

Tell your man "See? Lots of people do it! And I can already see you're a much sexier 'girl' than she is!"

When Abby comes out you'll need to reassure her she looks very feminine and sexy. Have her do a pirouette and tell her that her ass is hot and that her legs are divine! Turn to your trainee and say "I think you are much prettier than 'she' is when you're all dolled up." But leave it at that.

You'll need to loosen your man's inhibitions up so feed him liberal amounts of alcohol. Subtly touch and stroke him so he gets really turned on. Surreptitiously play with his nipples and squeeze his ass. Casually brush your hand across his bulge and try to make him as hard as a rock.

When Abby takes a toilet break whisper to him "Fuck I wish she was a real girl and you were totally dolled up as Becky so we could all play lesbian together! I'm so horny right now!" Take his hand and brush it across your nipples so he can feel you're turned on.

Ice them just before you do this if you're not actually horny.

Keep teasing and tormenting your man so he becomes desperately horny. Once you know he's loosened up, and he is a horny as you can make him, ask him if he would like to go and put on one of his bra and knicker sets as well as his stockings and heels and camisole (or just take his boy clothes off, if that's the case) and come out for you?

Assuming he hasn't already (as described above).

Tell him he can wear one of his dresses as well if he's embarrassed to be only in lingerie. Tell him you just want to compare the 2 of them. Do not make even the slightest of complaints if he refuses, just look disappointed.

When your man goes to get changed (hopefully) or when he goes to the loo (if he hasn't wanted to change) let him catch you squeezing the Abby's ass when he returns. Release it immediately and look embarrassed. Apologise profusely "I'm sorry, baby, it's just that I love the look of a man's sexy ass in a pair of knickers so much, and yours wasn't here for me to squeeze." And give him a really big smile.

Why? You're definitely pushing on some of his boundaries here and if he explodes at this point you're likely to be no chance of forcing him into the role of 'sissy' so you need to pack this project up and save your marriage right now!

Apologise to Abby and get her out of the house as soon as possible.

Grab your man and apologise to him profusely. Use tears and the likes of "I'm so sorry, baby. I just wanted you to have some fun" to placate him. Get your man into bed and fucking you as 'Brian' just as quickly as you can get his clothes off. If he won't make love to you you're really going to have to work on massaging his ego and getting him to desire you again if you want to keep your marriage alive.

Over the next few days lavish attention on him so he knows that you know you've 'fucked up' but leave his cock cage in an obvious place on his dresser and/or next to his side of the bed.

If he puts it away or throws it out, it's done. Enjoy your marriage and hope that some of the lessons he has learnt about how to warm you up and please you hold. If he continues to wear the knickers you purchased for him you're still in with a chance and if he puts the cage on himself, without any hint from you, it's still game on. You just pushed him too far too soon and you can circle back to this after a few more weeks of arousal and denial, interspersed with some fantastic orgasms, until you think he's ready for you to push him again.

1. You're going to have 2 scenarios here.

Let's look at scenario one: He does go and get changed.

If he didn't you can skim over most of what is happening below and go down to 26.

When he comes out and catches you feeling your guest's ass and you've apologised to him. Walk over and kiss him as passionately as you can, he's uncaged, so try to get him as hard as you can make him so that his dick is bulging out his dress, if he's put one on, or jutting out of his knickers, if he hasn't.

If he freaks about you obviously groping him in front of another 'man' I'm afraid your chances of turning him into your sissy are virtually none. Tell Abby to go home, take your man to bed, fuck him well and drop the whole thing.

This is why I've emphasised so strongly to this point that you must keep him caged and in a constant state of both arousal and desperate to come. It's so when you get to these key points they only thing he's really thinking about is his need to fuck, come and ease the pressure on his balls!

Ask your Abby if she thinks your 'girl' is sexy?

Instruct Abby that she must stay where she is sitting because this meeting is only for a chat.

Tell your man how goddamned sexy he is in his girlie clothes. Casually grope his cock and say, loudly enough for everyone to hear, "Fuck I'm horny right now!" and kiss your man again.

Tell him to walk a little way away from you and do the same pirouette as Abby did and tell him his ass is definitely sexier than 'hers' but maybe Abby's legs are a little better than his. Ask Abby to stand next to, but a little away, from your man.

It's way too early. If 'that man' touches him, or gets too close now, he's probably going to freak out!

Have them both do a slow turn around so you can compare. Casually give both of their asses a squeeze and say "Fuck you're both so very sexy! But I love my man best!"

Send them both to the bedroom to get changed but hold Abby back and whisper to her to try to casually brush your husband's cock with the back of her hand as they both strip down. Tell her that if he objects just apologise and explain that it was an accident and get out of there quickly. If he doesn't give it a bit of a stroke and tug but leave it at that and get out of the room.

You're pushing him again to test if he's going to let you to continue to take him down this path. If he freaks out at Abby's touch, you've got a long way to go. If he lets 'her' have a bit of a feel and a tug the below will go much quicker and easier, so let's hope he lets her grope him!

Send Abby home and then fuck your man's brains out. Make him service you with his hands and tongue first. Keep exclaiming how horny you are and how badly you need to come. Describe how the whole time 'she' was there you kept having visions that Abby was a real girl and that he was going to turn himself into 'Becky Cockslut' that, actually, he was going to be 'Becky Cuntslut' for the night.

I know, there's that word again but, trust me, he'll love how dirty it sounds in your mouth

And that they were all going to fuck each other. Tell him to talk to you as if he was Becky as he makes love to you. Once you are satiated let him slip inside your pussy and play with his ass until he comes, hard. See if you can get him up and have him go again. Don't act even a little disappointed if he can't. Once he is totally spent tell him that you once again want to feel his come leaking out of you as you sleep but you'd like him to put on the cock cage and his baby doll nightie and cuddle up to your back.

Tell him you want him to wear his cage because you "Know he is a naughty boy and will be hard in the morning and try to slip it in you! But you want to give him a special treat tomorrow so he needs to be patient."

25a. The 'dream'.

In the morning get your pantyhose out again and tie his hands and feet to the bed. Remove his cock cage and make him as hard as he can be. Use one of your scarves to blindfold him and stuff last night's knickers into his mouth. Lie beside him then stroke and touch him all over in random places, especially his nipples, but always go back to his cock. Oil it up and keep it well lubed so that you can give it an oily rub every few seconds.

Do not let him come!

Start to tell him about the 'dream' you had last night and how fucking hot it has made you this morning. Describe in lurid detail how you dreamed that the two of you and the 'girl' from last night, except she wasn't really the same girl because she was so gorgeous, that if she didn't have a cock, you wouldn't have any idea she wasn't a 'real girl'.

Describe her in lurid detail. Long blonde hair, full luscious lips, and a long neck, high firm boobs that had to be at least a full C cup and that they were so gorgeous you really wanted to feel and kiss them. Long shapely legs that any woman would die for and all men would drool over along with a firm round butt.

Explain how the three of you were sitting on the couch talking, you in the middle, and you had gotten so horny from looking at her breasts and seeing his cock jutting out that you just had to pull this (fondle his cock) out of his knickers and start playing with it. And, what was best was, that the girl didn't seem to mind at all! That she just started to play with herself through her dress as she watched you stroke your man's cock.

Tell him how you dreamt that, as he wasn't protesting, you leant over and took his cock in your mouth and all he did was lean back and groan. So you then proceeded to suck and deep throat his cock and that it felt so naughty and sexy to be doing that in front of someone as beautiful as our new friend.

Straddle his thigh so that he can feel how hot you are.

Make sure you are! Go to the toilet and play with yourself and fantasise first if you need to. Imagine you have the first of your bulls in there with you, perhaps. 

Start to dry hump his thigh as you describe the 'scene' to him. Tell him you lifted your head up so you could adjust your position and saw that the girl had taken her cock out of her knickers, and that it gave you a sharp throb in your pussy to suddenly remember that this gorgeous creature had a 'girlie dick' just like yours, just not so big.

Describe how she had lifted her dress up so she could play with the head of her dick and tell him that seeing her like that made you so horny you got on your knees, grabbed these (cup your man's balls) and, in one swift action, took all of him down your throat. Describe how, in your fantasy, you dreamt you had lifted your skirt up and pulled down your knickers so you could play with your clitoris and finger your pussy as you sucked him.

You'll need to be very careful here because you want to keep him on the edge and not over it into an orgasm. You're trying to give him the proverbial 'blue balls' until you are ready for him to come.

Tell him that as you were deep throating his cock you became aware that the girl had gotten on her knees right beside you and was watching avidly as you blew your man. That having that beautiful creature right there made you even hotter. Explain that she now had her cock right in the palm of her hand and she was furiously pulling on it. And fuck was that hot! And describe how her head kept getting closer and closer to the action and that her pulling got harder and faster as it did.

Say that you in your dream your jaw had started to ache so you pulled his cock out of your mouth and offered it to her and she immediately swallowed virtually all of it.

Ignore any protests he might be trying to make but increase the strength of the grip you have on his oily cock and stroke it a bit faster so he remembers he's horny and forgets everything else.

And then she rocked her whole body back so his cock slid slowly back out of her mouth. Describe how your mouth went dry and you almost came seeing her deep throat his beautiful girl dick. Tell him how she then swirled her tongue around the head before letting it slide back down her throat. Say you remember being amazed at her oral skills as she alternated between deep throating him and swirling her tongue around the head and you (give him a nudge in his ribs) didn't even seem to notice that someone else was now sucking his cock but, in your dream, you just didn't care because it looked so fucking hot all you could do was think about his mouth on your pussy and how badly you needed to come. Explain how, during all of this he just continued to squeeze his eyes shut and groan as he concentrated on not coming because it felt so good and didn't want it to end.

You should now be moaning loudly as if you're about to 'pop' and pinching his nipples as well as occasionally giving his cock a nice oily stroke. Make sure he can hear how aroused you are.

Tell him that, in your dream, because she was giving him such an awesome blow job, and that he was enjoying it so obviously, you felt free to sit up on the couch beside him and lift your skirt up, pull your knickers down and play with your clit, finger your pussy and masturbate as the sexy scene played out in front of you. But when you leant over and kissed him his eyes flew open and he looked at you, looked down to see who was blowing him, and then all he did was groan and grab her head with both hands and say "Fuck that feels so good!" And started to hump up into her mouth.

Say that, in your dream you remember being so angry that he didn't even care that someone other than you was blowing him that you wanted to punish him so you peeled your knickers off, stood up on the couch with your legs either side of him, pulled up your skirt, and sat down heavily right on his face. That you grabbed him by his hair (or back of his neck if blah blah ) pushed your pussy as hard into his face as you could and hissed "Eat my pussy you fucking whore!"

And you ground your pussy into his face. Hissing "Lick my clit and lap my pussy! Make me come you slut!"

And he did! Say that in your dream that as you came on his face, you heard him groan and shoot his load into the girl's eagerly sucking mouth. Then the dream ended and that now, remembering the dream, you are so fucking hot, you're going to need him to do what he had done in your dream to you for real.

Then immediately rise up, pull the gag out of his mouth and sit on his face. Hold the back of his head and hump his face, Grind your pussy as hard as you can onto his face and rub your clit across his nose. Hiss at him like you did in your 'dream' "Eat my pussy you fucking whore! Lick my clit and lap my pussy. Make me come, you dirty slut!"

Ride his face to as many orgasms as you can.

Try to actually smother him occasionally with your thighs and pussy, not for real, but for a few moments.

Once you are totally satiated push your knickers back into his mouth. Smack his balls and insist if he tries to resist. Then put your strapon on, loosen up his leg restraints so you can lift his legs up and get access to his man cunt and roughly fuck him until he comes from the 'cock' scraping across his prostate. Scrape up as much of his come on your fingers as you can, take your knickers out of his mouth, and feed it to him. Tell him how hot it makes you watching eat come.

Not 'his come' but just come.

Then play with him until he is hard again and ride him until you both come again.

You need to come at the same time as him, or, very soon after. So if you're not going to be able to you'll need to pretend again.

It remains vital, at this stage, that he still feels like he's is your fuck star, your sex god, and that no one else could possibly be as good as him.

Once you have both come, release him from the restraints, remind him he needs to clean you up and put the cage back on. Don't let him clean himself up, tell him it looks so slutty on him and that you love it! Cuddle up with him and take a hold of his cage and say "Fuck that was so good! I think we should get 'Abby' (the 'girl' from last night) back and make her sit on the couch, dressed all pretty, and actually do what I dreamt about, what do you think?" Explain that you know he won't really want 'her' to blow him, because, you know? She's actually a guy, but it would still be really hot to blow him in front of her and to sit on his face as he eats your pussy while Abby watches and maybe they could let Abby play with herself as you did? Would he be in it?

Keep bringing it up until he agrees to have her come back over and 'see what happens'. Use the "You know you're eventually going to let me do this because you know it will make me happy and you love making me happy" approach along with big smiles and kisses and strokes of his cock.

25b. Bringing the 'dream' to reality.

During this time you'll need to stay in contact with Abby and keep her up to date with what is happening. Tell her you're hoping to get her over again soon and that it will be for some limited play this time. Instruct her to always refer to you as Mistress and/or her Queen when she addresses you as you want your sissyboi to get used to calling you that too. Tell Abby that when she comes over next she is to go straight to the bedroom and get changed into the sexiest outfit she has. Choose her one from your husband's collection, or buy her one yourself, if she doesn't have one and lay it out for her.

Say that, once she has fully changed, she is then to sit on the stool at your dresser because you're going to do her make up for her this time.

Assuming she isn't already proficient at it. If she is proficient tell her to make herself up as prettily as she can then come out.

Because, this time, you want her to be as feminine as possible.

Once another visit has been made make sure your man knows he's to be already dressed as Becky, this time, when Abby arrives and that you expect him to go 'all out', heels, stockings, garter, knickers, the shortest of short skirts, bra, a skimpy top, wig and full make up because your dream was sucking off 'Becky' not 'Brian' in front of Abby. Remind him that he doesn't need the cage because you're going to be blowing him, probably, if it feels right.