Sissy Anal Guide

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Home - Cuckold Guides - My Step-By-Step Sissy Training Guide
I want this to be a resource list and an advice guide for all practicing and wannabe sissies. We have welcomed back a regular sharer on our blog who is going to walk you through the most vital steps in becoming a sissy and femme. She is an incredible woman with a soft spot for sissies, so whether you’re a sissy reading this looking for advice or a partner training up their slutty sissy, this is the place to be.
Before you read on don’t forget to check out our membership, it’s filled with advice, cuckold/hotwives hot stories, cuckold erotic videos, hotwife text conversations and you would be supporting us and our mission to empower cucks, sissies, hotwives and bulls across the globe. Have fun! Jack and Sarah <3
I’m Femdom Queen, I converted my completely straight husband and turned him into a real-life cum loving slutty sissy. He went from never sucking a dick, to having his first creampie within a few short months. He now has a new name, Cindy, and he has come along leaps and bounds since we first started our sissy training and he has surprised even himself.
I wanted to explain to you and guide you on exactly how I converted my husband into a sissy and the steps you can take yourself or on your partner too. If you have any questions leave them in the comment section down below and I will get back to you asap.
I am going to be showing you exactly how things are going to go down as you convert yourself or your partner into a sissy.
So, what does our sissification schedule look like
Gaining female traits – this is the art of convincing yourself and others that you are femme. These start pretty simple and can get harder as they go on.
Slutting up – Learn how to be slutty and become the ultimate cum-guzzling sissy. This isn’t just in the bedroom but learning how to ooze this type of trait at all times.
Getting comfy – Ideally, you need to learn how to get comfy around cocks, cum, and any sexual situation you find yourself in.
Anal training– Training your ass to cum, take cock, and be the ass pussy we all know that it is.
Sissy lock-up– Cock cages are so important, not only do they deny you pleasure but they show just what a submissive little femme that you are.
Cock training – This isn’t about you but about the cocks you are going to be taking. Learn how to take them, use them, and be the best sissy to ever touch them.
Following these guidelines, slowly and submissively will convert you into the sissy you want to become so without further ado let’s get started.
It’s time to start your sissy training, start slow, take notes and follow your cravings.
Warning: There is no going back, once you take these steps, you’ll start the sissy process and there’s no going back, make sure you’re ready for your transformation.
These femme traits can be acquired in any order, just make sure that you nail every single one before moving on.
Voice Training: Training your voice to sound more feminine is one of the key steps. You want to sound feminine without sounding like you are putting it on. Speaking in a higher pitch, copying female voices you like the sound of and getting into the habit of giggling, speaking and conversing like a woman are all key. This is a great video on making your voice sound more feminine.
Mannerisms: Men are more likely to chew more loudly and obnoxiously compared to women, likewise men will belch, yawn and laugh in a typical way and so getting female mannerisms down will aid you in your sissy transformation. Covering your mouth when you laugh, chewing and eating with more mindfulness, apologizing for belching, learning not to shout and scream like a man, etc. Generally being quite coy in your mannerisms will make you feel more relaxed as a sissy and will allow you to slip into your perfect character. Mannerisms you should also make a note of is:
Get A New Name: Your partner may want to decide this for you or if you’re alone, you may want to pick your own. Find a typically female name that you like, for my hubby it was Cindy and now refer to yourself as that whenever you can.
Learn How To Use Makeup: Learning how to use makeup is a very important tool for sissies, you can feminize your face and enhance your features with the power of makeup and it can make you feel even more beautiful. I found this video really helps as it’s quite detailed and explains the reasons behind each step.
Learn How To Shave: Shaving is very important for a sissy and learning how to do that properly will allow you to prevent razor burn and the dreaded itch. Some great tips sissy shaving tips can be found here but if you just want to know the basics. Use a new clean razor, shave after a few minutes IN a warm shower, use shaving gel or oil, shave against the grain, exfoliate afterward, moisturize afterward and wear loose clothing.
Your first wig: My sissy husband Cindy loves this wig. It’s fluffy, great-quality and it helps her to transform into the beautiful sissy that she is. Having a wig or even a girly haircut sets the transformation process into motion and allows you to become the sissy that you know you are.
Start doing Yoga/Pilates: Work out your ass and your legs, get them carved into a feminine shape with these sissy workouts. Start a daily booty workout routine, get that butt girl!
Sitting down to pee: You know longer stand-up to pee, you sit down like me. It might feel strange at first but you will get used to it and if you want to become a full-out sissy you have to do these things, even when you’re alone.
Wearing female lingerie: This is a gorgeous lingerie piece that my sissy husband looks divine in. He always feels so sexy in it and it makes him feel gorgeous. Also, be sure to start wearing female inspired clothing such as summer dresses, tank tops, bras, and skirts.
Painting your nails: Keep your hands and nails groomed, wearing clear varnish or color is up to you, just keep them in great shape and don’t forget your toes.
That’s it! You completed it. Now, it’s time for us to move onto step 2 of your sissy transformation and that’s slutting you up in a simple yet effective way.
Start Tucking: Learn how to tuck your penis correctly, this is for those types of female clothes that just call for tucking or for when you just choose to do so, as many sissies enjoy taking tucked pictures or just playing around with it. This video is great and it gives you some great advice on tucking:
Your First Slutty Panties: You have gotten used to lingerie and female clothing by now but you need to get yourself used to some slutty panties, wear these not just in the house but under your clothes when you’re going out and about. They’re also crotchless which makes them ideal for slutty sissies.
Your first stockings: Every sissy must wear stockings at some point in her life. These are my husband’s favorite stockings, you must wear them just to feel sexy or during sex, they feel so smooth and make you look so slutty and lady-like.
Your First High Heels: Finding heels for bigger feet can be tricky but I got my sissy husband these heels and they fit like a dream. You learned how to walk like a woman in the first step of this guide so now you need to master walking in heels like a woman.
Your first fake breasts: If you want to go up a cup or two, fill out your lingerie with some fake breasts. These are great and work well, they make my sissy husband feel really good about himself and they will make you feel like a little slut.
Your first Slutty outfit: Learning how to dress as a woman is important but learning how to dress and pull-off a slutty outfit is even more vital. This video will teach you those must-know facts about dressing as a sissy and allow you to pull off that sexy outfit even better.
Posing like a slutty sissy: You already learned how to walk, stand and sit like a sissy so now it’s time to learn how to use your body and your angles to look like the whore you are. Emulate your favorite poses from other sissies, take some inspiration from these sissy poses and get your camera and take some snaps of yourself, you will be surprised by how good you look.
Dick taking positions: Practice your favorite dick taking positions whilst posing in front of the mirror, do you like to be on all fours? on your back? standing? Learn your positions girl and learn what feels good by using a dildo (more on that below).
Bleaching your ass: To be a perfect sissy you’re going to want to not just shave or wax your ass but to also bleach it. This video gives some great facts about the whole process but I do recommend you head on over to a salon that specializes in this service.
Watch sissy porn and learn what kind of guys you find attractive: Get off on the porn you watch and learn not just what you like the look of in the bedroom but also the guys you like and how you want your anal pussy and clit to be treated.
Write down porn scenarios you want to try: You may find you want to be dominated or perhaps you have a threesome kink or you may just want to stick to sissy humiliation, whatever turns you on, make a note of it and master how you can bring it into your real life.
Learn your new body: Explore your smooth hairless body, play with your clit, your ass pussy, get to know what turns you on and what feels good. How can you expect anyone else to know if you don’t? Your ass is now your pussy and your cock is your clit and shall be referred to as such.
You did it! You successfully slutted yourself up in the easiest way possible, now it’s time for the next step of this guide.
Getting your first dildo: This dildo is great, it suction cups itself to anything hard and flat so you can practice on it in most positions and anywhere in your home. Learning how to ride a cock will make you an even better sissy and get your ass prepared for the real thing.
Getting some fake cum: You can buy this cum lube that looks and feels like real cum to practice taking cum with and to take some cute pictures with. Squirt it over your face, body, clit, or ass pussy for a realistic effect and get your sissy self ready for the real thing.
Learning to suck your dildo: Get used to what it feels like to have a nice big cock in your mouth, take it all the way back into your slut throat and gag on it. Feel it deep inside of you and practice your blowjob skills.
Learning to swallow cum from your dildo: Get ahold of this ejaculating dildo and swallow the cum that comes shooting your way, this will get you used to the sensation of cum and allow you to practice your swallowing skills.
Suck Men’s Cocks – Once you are comfortable with you dildos and your new slutty sissy persona, move onto sucking real male dick. Get on your knees and suck, arrange these meetings safely (more on that further on in your training below), and feel like a total slut as you suck off these men.
Find A Mistress – If your partner isn’t going to be your mistress, consider finding one. A mistress will keep you in check, will bring out even more of the sissy inside of you and she knows exactly how to tease and keep her sissy on her toes.
You’re done with this part of the training! well done you little whore. Now, it’s time to move on.
This is a really important step, you need to get your new pussy ready for cock, this is my sissy anal training program:
Cleaning your pussy: Enjoy this anal cleaning guide and make sure your pussy is nice and cleaned out before you engage in any play, you want to be a smooth, perfect princess, don’t forget that.
You need a cute butt plug: My hubby wears this pretty pink butt plug around the house and during play. It stretches him out a little and it looks so pretty and perfect. Plugging up your pussy with this plug and enjoying just how cute it looks is all part of being a sissy.
Your pussy needs to be stretched: Start small, you have to go slow 2 – 3 times per week, slowly work up to bigger. Once you can comfortably take the plug, try this dildo. Stretch it out until it fits in there all nice and comfy and revels in the fact that you’re a good little whore.
Try A Fake Creampie: Using the ejaculating dildo that I mentioned earlier on, try having it creampie inside of you, fill up your pussy with the fake cum, and enjoy the feeling of completion.
Having Your First Sissygasm: Work on your anal orgasms, read guides and follow steps on how to achieve it and learn how to stimulate your ass properly in order to come through your new pussy rather than using your clit.
Learn to use a magic wand on your clit, while you play with your ass: Remember your clit is your dick and so you need to learn how to stimulate your clit, just like a real woman. Use your wand on your clit and get yourself off, it’s such a pretty sight.
Well done! You have learned how to use your new ass pussy, now it’s time to move onto the next step!
Get yourself a cute cock cage: I make sure that I lock up my sissy husband mostly at all times, it’s a humiliation and a punishment thing for us and I know a lot of sissies and their mistresses feel the same. My hubby has this pink cage, I think it’s easy to use and it keeps him nice and secure.
You are caged till you have your first real cock: Once you have your cage you will be locked up until you take your first real male cock. How does that sound little sissy?
You can only cum using your butt: You can ejaculate, but not from touching your cock, keep yourself locked up and learn to get off only with your ass, like a good girl.
Finding a Keyholder: Find someone who is in charge of your cock cage, maybe it could be me? If you would like it to be me leave a comment down below, you can also have Sarah (the owner of this blog) hold your key for you, find out more by joining the membership.
Wear lingerie and a cock cage: It’s not the comfiest of outfits but it’s something you need to master to become the ultimate sissy. Wearing cute flattering girly lingerie all whilst your cock clit is locked away all tight and secure.
Becoming a slave: Becoming a slave for cock and other pleasures can be difficult but learn how to submit and get to your knees and spread your legs for cock.
Degradation/humiliation: Being humiliated and told what a worthless little whore you are is all part of the process, either you tell yourself that when you’re all dressed up or have your partner do it during sex. You need to learn your sissy place in this world and that is at the bottom of the pecking order, you need to be taught what a slut you are.
Understanding the names your new anatomy is given: It’s all well and good knowing that your cock is now called a clit and your ass a pussy but you need to believe it and call them that at all times.
Next, is your final part of this sissy training guide.
Finding the perfect guy: use dating sites like adult friend finder, FetLife or r/sissypersonals or r/sissykik, to find the right guy or date for you. Always be safe and be careful not to post pictures of your face onto any of these places.
You can also use these sissy dating sites to help find the right guy to share yourself with.
Sucking your first real cock (will you swallow?): All of your training has really lead you up to this moment, taking your first real cock. Will you spit or swallow? Where will it happen?
Having him inside you for the first time: Your ass should be ready now after all of your training and having him inside you for the first time is going to feel amazing. Well done little slut, you have done it.
Having him cum inside you for the first time: Your first real creampie will be incredible, having a man fill up your ass pussy for the first time is a moment you will always remember.
Share A Cock With Your Wife: If you’re married like us, then enjoy a cock together, it’s the best. If you’re not married, share a cock with your mistress, enjoy them being in charge, and feeling like a useless fuck toy, my hubby loves it.
Live out porn scenarios: Remember you were acting them out earlier on in my guide? Well, now it’s time for you to do it for real this time. Do you want to be the slutty sissy or the femme coy girl? Whatever you choose, have your fun girl.
Be the slut you know you are: You know you’re a slut or you wouldn’t be here. You are a sissy slave and you are now fully prepared to go out and live that life.
I want to see your updates in the comments below, let me in on how it goes for you or your partner and if you want any advice or if I have missed anything let me know in the comments down below. I can’t wait to hear about the sissies my guide has created.
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It's me again and I'm here another part of the journey of turning my husband into a cum loving man. It took time, but I'm still shocked at how easy it was to turn my straight husband into a sissy who can take a bigger cock than I can. I'm…
Jack and I used forums and chatrooms to gain the confidence to try out this lifestyle and we now use them to meet others and build relationships. Forums and chatrooms are a key part and help create this amazing community. So, we decided to create a constantly updating list of…
I love submitting our tales here, it has been eye-opening for us and I am forever grateful to Jack and Sarah for allowing us to share our lessons and stories.
My sissy husband is still in step 1 but we are getting there. She is a good girl trying her best.
I can’t wait to be a good sissy. Maybe some day i will have a keyholder of my own.
I’m having trouble accepting I’m a sissy. The more feminine I start to become the more I get scared and fight it. I don’t know what to do! Please help.
Hey I’m looking for a mistress to help me along, or a fellow sissy to keep me motivated
I’m trying to learn how to become a sissy boi. I would love to talk with you
Will you please be my key holder and transform me into a sissy slut slave
My sissy training will begin soon and I am excited about the journey. I have a Mistress who direct my training and be my keyholder.
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You're in the right place, princess.
A Beginner's Guide To Being a Sissy
Training is vital. I suggest four sex toys for your training regimen:
Set a goal of sucking your dildo every day. Fuck your ass as often as you can. You'll have a good time and be ready to be a filthy cock slut.
Eating right is vitally important. Watch this YouTube video to learn more:
Walking, jogging, yoga and women's fitness regimens are perfect for sissies. The goal is to have excellent posture, a flat stomach and a thick ass. 
Here's a playlist I put together, and will keep adding on to, of workout videos for sissies.
Shopping for your new sissy clothes is extremely fun!
Here's a few ways
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