How to Make a Sissy

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Look at you go, you dirty little slut! A dick in your ass and pussy at the same time! Question: Would you like one for your mouth, too? 

Instruct your boys that they are not to come until you say you're ready for them to and ride them both until you can't possibly go anymore. Let them both come in you and make your man clean up your pussy and ass as well as Mark's cock. Remind him to put his cock cage on.

Send Mark home, you need to have a chat with your man.

The chat you have will be the same here as the one above where your man was soft.

  1. Defining his new role.

Tell your man to wait for you at the dining room table and go shower and wash the remnants of your love making off, change into something comfortable but quite severe (as opposed to sexy. You're going to be very much Mistress (your name) for this). Take your time so he has to stew for a while.

When you come out sit opposite your hubby and remain quiet for a bit. He will, more than likely, make one last ditch effort to regain some of the control he has seemingly all given up to you. Let him whine for a time, then forcefully interrupt him. Say "Let's lay all the cards on the table here, Brian. You're nowhere near as 'straight' as you thought you were, are you?"

He will try to interject with a "Yes I am! I was only playing with Abby because you wanted me to!"

Override him hard. "Not this morning, or indeed, last night in our bed! It was 100% Mark you were sucking, fucking and getting sucked and fucked by! Argue last night all you want but today it was definitely Mark that you were having sex with! You can't argue this with me because I know, I was there! You sucked his dick and let him suck yours so let's cut the bullshit, ok?"

He will probably still try and argue so hold your hand up and say "The thing is I don't care! Before we started on this journey our sex life was boring! Now it's fucking awesome! We've done and experienced so many things that have been fantastic! And, we're going to continue. Actually, I'm going to continue, you can continue with me, or not, but, if you choose to stay, there's no more selfish, uncaring, only gets what he wants, Brian! There is only what you have been for the last (however long it's been) my caring, looking after me first, sometime 'Becky' husband who puts my needs before his 100% of the time!

This needs to be said, Brian so here goes. Before we started all of this I really wondered if you actually liked sex with me, or any woman. You just seemed to want to hurry up and shoot your load so you could get it over and done with. I wondered if you weren't, at the very least, bisexual, if not actually gay!"

He will definitely protest here.

Say "FFS Brian! How many times do I have to reassure you that you're obviously not gay? No gay guy could have done me as well and/or as often as you have over this journey! But it's time to admit to yourself, as well as to me, that the only way you can have a truly good orgasm is when someone is in your ass! How many 'straight' guys need a tongue or finger or cock in their ass to achieve a proper orgasm, Brian?"

He will whine "You did this to me! You made me a cock sucker!"

Reply "Did I Brian? You could have stepped out of this anytime you wanted to. Think back, my man, I offered to let you out of it any number of times! No, my love, you were a more than willing convert to all of this because you were finally getting what you needed to orgasm totally and exquisitely. Let's face the facts here... Know any of your married friends or workmates whose wife not only lets them have sex as often as I do you but loves it and joins in as wholeheartedly as I do?"

If he's honest he has to shake his head here.

Follow up with: "I need you to tell me you want to stay and that you want to continue with these games. I want you to say 'I accept that you're my Mistress and that I live only to serve you'. If you're not prepared to accept these demands, and make this promise, you can pack your bags and go! I'm not fucking around here, Brian. I need my man but I need to be 100% certain that you're never going to backslide into the 'old Brian' ever again!"

The previous hard pushes you have given him should have crushed him into a place where he can't refuse you.

As soon as he has made the vow walk around to him, sit on his lap, kiss him and say "Thank you, my love. Mama will look after you, I promise!"

Congratulations! You've taken a 'strong independent alpha male' and turned him into a cock sucking sissy!

  1. And last. Taking your first bull.

After he has made the vow say to him "To show you how much this means to me, babe. Follow me."

Tell him to grab a rubbish bag and follow you into the spare room. Start to dump all of his 'Becky' clothes into the bag (keep a couple of your, and his, favourite outfits including a pair of heels, just in case he'd like to dress up again for 'old times'' sake in the future) then go into your bedroom and remove all of his women's undergarments except for a collection of about 3 -- 5 of his sexiest and smallest thongs (these are what he'll wear when you're entertaining a bull) and get his old men's undies out.

Once everything is in the bag have him sit beside you on the bed, hold his hand and say forcefully "Two things, Brain: 1) you will remain clean shaven from the eyebrows down. 2) The cock cage stays on except for when we're having sex!"

Say it with absolute conviction you will be obeyed.

Make him repeat what his two ultimatums are and agree to them. Once he has, say "Good boy! Mama, and you, are going to have so much fun!"

Take him out for the day and do the usual mundane things, do a bit of shopping, get some lunch. There's going to be a small difference though. If you see a hot looking girl nudge him and say "There's one to perve on, babe, wonder if she's got knickers on?"

When you spot a guy that you think is hot also nudge your man and say "He's hot, don't you think? Wonder if he's gay or bisexual and would like to come and play with us? Do you think he has a big cock? Should we ask him?" And laugh.

This is confirming to him that things have changed. You're going to open about your sexuality and, if you find a man (or even a woman, if you enjoyed 'playing' with Ann) attractive, you're going to consider them potential sexual partners.

Throw all of his Becky clothing into good will while you're out.

When you get home take him straight to bed, let him remove his cock cage then make him service all of your sexual needs before putting the strapon on and fucking him to orgasm.

Yes, I know I said to 'never make him come' but you've won so the 'rules for conversion' no longer apply. You may even let him make love to you between bulls occasionally, but keep an eagle-eyed look out for any backsliding, and jump on it immediately.

Earlier I made mention of finding out which of his mates and work colleagues found you hot but you should be very wary of selecting someone from either of these categories as a lover. Cuckolds can very quickly become the object of ridicule and scorn if their predilections become common knowledge.

Note: Why do Australian men always come so quickly? They can't wait to get down the pub and tell all their mates. 

So unless you're sure of their discretion and/or you know for sure they're bisexual and will also use your man (so you have the threat of dropping them in it as well if they want to blab) avoid playing with anyone from either of these categories.

Give it a couple of weeks until he settles into his new role and accepts you in yours and then login to your 'kink site'. Instruct him to come and look with you. You're going to look for someone, with as big a cock as you think you can handle, to start the next part of your sexual journey.

There will be no shortage of guys with 'dick pics' as there profile pic on their shell profile (shell profile: little in the way of real information or content filled in) ignore all of these. They're going to be about 99% fakes who only want to wank to the fantasy and will never commit to a meet.

What you're looking for is someone with the confidence (and smarts) to put a face pic up. Somebody who has taken the time to write a decent introduction and has listed what they're looking for clearly. He needs to be 100% bisexual (no room for 'curious' or 'wanting to try') contact him and initiate a chat.

Trust me he'll be so shocked that a woman is contacting him that he'll probably doubt you exist. He'll be sure that there's a 'sissy' but will doubt there's a Mistress!

Use the same process as described above where you 'recruited' Ann into your scheme. Exchange some basic texts, Exchange phone numbers, and chat. If it feels right try some 'flirtatious chat' then, if that goes well, invite him over for nothing more than a drink and a chat. Emphasise it will be for nothing more than that the first time.

You want someone who is in control of themselves and their lusts and libido. If they're not, they may be fun later if you want to be well and truly 'fucked', but they're no use to you now.

For the meet you want to dress yourself as sexily as possible, full make up, etc. Your man is to be present when you meet (let's call him) Phil. Make sure there is a definite attraction between you and Phil.

In blunt terms, you not only want to fuck him but he wants to fuck you.

If the attraction is there arrange for Phil to get an STI check and email you the results.

You're going to bareback with him so you want to know he's clean. It's a bit blunt, I know, but this is 2022, babe, you can't be too careful!

As soon as you have the results arrange for Phil to come and see you to 'play' on a Saturday night.

In preparation for Phil's visit you'll need to purchase an 'O' ring for your man and a douche kit (also for him). On the Saturday afternoon, about an hour before Phil is to arrive, have your new sissyboi prep you to take Phil's bigger cock. Start by making him use his tongue and fingers to 'warm you up'. Once you're buzzing along have him lube the butt plug that approximates Phil's dick size then have him tongue your clit as he inserts one, two, and then three fingers into your pussy. Once you're ready have him slowly insert the plug into your pussy. Make sure he is tonguing your clit as he stretches you.

Repeat the process with your ass.

Once your sissy can slip the plug into both your ass and pussy without any discomfort send your sissy to the bathroom to shower, shave down and douche his anal passage. Have him lube and stretch his ass with the same plug that he used on you. Then instruct him to put on his thong (he should have put his cage on as soon as he got out of the shower) and to come wait with you for your bull to arrive.

Phil is going to have his dick in your man's ass and then in your pussy so you need to make sure your man's ass is clean (for obvious reasons).

When he comes out from the shower bind the 'O' ring into your sissy's mouth.

On Phil's arrival send you sissy to kneel toward the head of the bed, on your side, with his head up, eyes down and his hands clasped behind his back.

Greet Phil with a big hug and a kiss and set about using all of your finely honed skills to make him as turned on and desperate as you can as quickly as possible.

He's here to fuck you, not engage in small talk.

Tell Phil that your sissy is kneeling in the bedroom and that he is to use your sissy's mouth and/or ass to 'warm up' in because you want to feel his come splashing in you as soon as possible.

Lead him to the bedroom and climb up on the bed. Instruct Phil to "'Face fuck' this sissy slut! He's only new so feel free to gag him with your cock and make him choke. Use his ass if you want!"

Lie back and enjoy the show. Phil won't want to come in your sissy so he won't use him for very long.

When Phil climbs onto the bed spread your legs, encourage him to get between them, and guide him into you. Revel in the feeling of being even fuller than the strapon your man used to fuck you with. Give both Phil lots of verbal encouragement to fuck you as hard as he can. Try to have at least two extremely loud orgasms then, before Phil blows, get him to lie on his back, straddle him, take his cock in your hand, lean forward so you can watch and lower yourself onto his dick. Exult as you see and feel that big, ramrod stiff, dick slide into your nether regions. Ride him to another orgasm. Then encourage Phil to "Come inside this hot pussy, stud. Fill me full of your man juice!"

As soon as Phil has finished blowing climb of the bed, straddle your sissy's face and hiss at him "Clean Mama's pussy, you fucking slut!"

He'll have difficulty complying because the 'O' ring will be in the way. So, when your sissy has cleaned as much of Phil's come up as he can, get back on the bed and see if you can't get Phil hard again. If he can, tell your sissy to hand you the lube from off your dresser, grease Phil's pole up, lie on your stomach, with a pillow under your hips and tell him to fuck your ass. Instruct him to be gentle until he's all the way in and you tell him to go. Once you've gotten used to Phil's extra length and girth tell him to 'give it to you hard'. Ride his cock to another orgasm and get him to blow in your ass.

As soon as Phil has blown a second time send him home. Take the 'O' ring out of your sissy's mouth and release him from his cage. Make him use his tongue to clean Phil's come out of your pussy and ass. Once you're clean put your strapon on and fuck your man to an orgasm.

As he moulds to his new role releasing him from his cage long enough to have a wank will be is as far as you will go.

Epilogue: The obvious question is "Will the above work?"

The short answer is "No, probably not!"

Now don't get me wrong here the above is a very good starting point for you to use to sissify your man. But to follow it step by step and word for word? No, there's too many variables at play here and I've made too many nested assumptions that your man will react a certain way. I have no idea whether he will or not as I haven't met him! The excuse to get him to wear women's clothes is weak and the reason for making him become more and more feminine needs to be stronger, you'll need to work on and adjust these parts to something you think your man would buy into. A tactic that may work is to simply state that having him dressed enfemme turns you on and the more femme he gets the more turned on you become (hard not justify not taking a woman lover on this track though).

If you want to try to turn your man into a sissy, using this, or some other method, the key parts are getting him permanently locked into a cock cage and to then keep him perpetually horny and frustrated with the only relief he gets is when he's taken another step towards being your sissy (you must never let on this is your goal until the deed is done).

The longer answer is "Maybe."

I have helped a total of 6 women try to turn their man from a total selfish prick, who only thinks of his own needs, to a willing cock sucking sissy. Four of them are currently living the Mistress/sissy life style. In all of these four cases I was involved intimately in the turning and training of her man, having met them both and I stayed in constant contact with the female partner monitoring and adjusting as required. Once the conversion was complete and I was their first bull (my reward for services given ).

One is divorced and is currently looking for a trained sissy to own.

The other's husband is now her 'wife'. Her man has transitioned to female having had both top and bottom surgery. They enjoy an extremely varied and rewarding sex life together sharing both men and women as desire takes them.

The End.

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7 Comments
NicolaTgirlNicolaTgirl6 months ago

What a detailed plan. I would embrace this if a female partner were to follow a plan like this on me .

FranziskaSissyFranziskaSissyover 1 year ago

Unfortunately there is nothing like a simple straight path ...... Why women or woman want such changes, because they love the hubbies? Otherwise they would seperate or divorce them!? ...... If sexual attraction or love is still in the air, yeah the mistress submissive play can work it out ..... But it takes time patience nerves and much more ..... And absolutely sure a helping hand or online instructions or real time meeting will spark the fire and speed thinks tremendously ...... And it's extraordinary that You Master are using your experience to guide them, thank you for this

Curtsey

AnonymousAnonymousover 1 year ago

Had never read 14 pages of anything on literotica. Needless to say I'm not dissapointed

kellijane001kellijane001almost 2 years ago

Wow - awesome advice - thanks John.

I might try some of it :)

love

Kell

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