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Sissy Training Tips: Essential Concepts for Beginners

Sissy Training Tips: Essential Concepts for Beginners







Ashley Grey






November 25, 2019






Sex Facts , Sex Tips





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If you are new to sissification, then you probably have a lot of questions, many of which will be answered as you delve into your research about the lifestyle. The most important thing is not to feel too overwhelmed in the beginning. Sure, there are a lot of things to learn, but learning is the fun part. You don’t have to know everything immediately.
Sissy men are one of the more exciting kinks to emerge in the S&M world in the past decade. It’s almost difficult to believe there was a time when men did everything possible not to be called a sissy. It just goes to show how much we have evolved, as toxic masculinity gives way to the blissful glee of the sissy life.
So, what exactly is a sissy? Wikipedia refers to it as “ feminization .” It is defined as: “ The practice of dressing a submissive partner as a woman and/or encouraging or training a submissive partner to act in a feminine or exaggeratedly feminine (“hyperfeminine”) manner.”
It goes on to say, “If assigned male at birth, the submissive partner may be called a “sissy.” Feminization is usually achieved via cross-dressing, where the male is dressed in female attire, ranging from just wearing female undergarments to being fully dressed in very feminine attire, including make-up, hairdress, and nail polish. Some males take on tasks, behaviours, and roles that are overtly feminine, and adopt female mannerisms and postures in tasks such as sitting, walking, and acting in a feminine manner.”
Becoming a sissy might just be the most natural state you have ever known. Perhaps you are someone who can easily adjust to this lifestyle, and the question of how to be a sissy will be easily answered.
As you can see, a lot of the process of becoming a sissy involves making a lot of big decisions. Ironically, you are in control of who it is you want to become. Your dom and those in the community will then likely honor the choices you make, while you let down your guard and allow them to choose how to best utilize you inside of those choices.
There are several important things to know when you are about to become a part of the “sissy” lifestyle. Preparing yourself with some simple training can make a huge difference in the type of experience you will have your first time around.
The following are some vital training tips to be aware of:
There are many things you are going to have to learn in order to become fully sissified. These include many non-sexual things, as well. Here are just a few of the things you should keep in mind as you prepare to become a sissy.
Maybe you have a support network in your life that will help guide you. Perhaps you don’t. Either way, there is a lot of research you can do on your own to prepare yourself for this unique lifestyle. It might be the “sissy” life, but it takes a lot of courage to allow yourself to be vulnerable with others.
You are dipping your toe in. Whether or not you decide to dive in is up to you. One thing is for sure, though. You should feel far more prepared now to decide if being a sissy is for you.
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Today’s wonderful article is written by one of my close friends, she is an amazing inspiration for anyone into sissy training and I had to have her share her story and training steps here. I hope you enjoy – Willow
BDSM roles and the BDSM lifestyle come in many different forms. They can be confined only to the bedroom and to sexual pleasure, but they can also spread wider into other areas of a couple’s life. The dom can continue being the dom even when the sex is over, and the sub may well love being a sub outside of sexual context as well. 
This is, in a way, the type of lifestyle my husband and I lead. I am a female dom, have always been, and he is a sub. Not only a sub, but my husband is also a fully-trained, fully broken-in sissy. 
If you’re new to the term and are curious to find out more, or you already know what it is and what to learn how to be a good sissy (or train a good sissy), read on for my detailed experiences on the matter. 
To put it in simple terms: sissy training is when a submissive man starts behaving more like a woman. Both during sex and in life, he can start taking on more traditionally female roles. This can be anything from wearing women’s clothing (including heels) and makeup, growing out his hair or wearing wigs, changing the pitch of his voice, the way he walks, gestures and similar. Sissy men also engage in typically female activities, such as cooking, cleaning, servicing their dominant partner sexually, etc.
The extent of the sissy training, how far a man is willing to go to become a sissy, depends from one person to the next. No two subs are the same, so no two sissies are the same. Before you decide to become one or to train one, these limits and boundaries need to be discussed extensively. 
I always knew I was a dom. Almost from the moment I lost my virginity, I realized I had a preference for a more controlling, power-wielding role in sex. None of my male partners ever had a problem with that. Maybe because I was always upfront about it.
This is how my husband and I fell into a good rhythm long before we got married. He never explored BDSM before but found that he would get particularly horny being dominated. Him being a sub was obviously perfect for our bedroom dynamics. 
It was only after marriage that we started talking about possibly training him as a sissy. He is bisexual, as he had told me a long time ago, and I entertained the idea of sharing him with more dominant men. I loved the thought of watching my husband getting manhandled by a stronger, better-looking guy than he was. 
It wasn’t long before we started the training and today, years into it, I can honestly say that it’s one of the best things I ever did in my life. 
I regularly find dominant men to take advantage of my husband and sometimes even to have sex with me after if I’m in the mood. It’s a win-win situation for everyone involved. 
The first thing you need to know about sissy training is that it is not easy and it takes a long time. 
It requires constant, and I mean constant, communication between you and your sissy, and you always need to check in with each other’s emotions and headspaces. While assuming roles and acting out fantasies, both sexual and not, is a lot of fun and a huge part of who we are, we never want to cross over into the realm of abuse and manipulation. 
This is why sissy training is a reflection of deep understanding and trust between the dom and their sissy. You can’t so completely give yourself to someone you don’t trust, and the fact that my husband lets me train him is one of the biggest compliments (and turn-ons) I’ve ever gotten. 
At the beginning of the training, we started out small. Bras, panties, perhaps a little bit of makeup during sex. The main thing here is that you and your sissy get a feel for it and find out where your comforts lie. If both of you are more than okay with what’s going on and wish to proceed, then you can get into more intense stuff. 
Ultimately, you will be able to get your sissy used to anal penetration and possibly getting dominated by another man. It took us a couple of years to get to that point, so don’t rush!
These are the steps we took in our sissy training. They may not work for everyone, so make sure to discuss them with your sissy before you try any of them out. You may wish to skip some steps or not go further than others – that is also fine. Each couple’s story is unique and what matters here is that both of you are excited and eager for more of it. There’s no point in doing it if it’s a chore or worse, if it makes anyone uncomfortable. 
That being said, here are some useful tips on how to go through sissy training:
The essence of a sissy is for him to adopt a feminine aesthetic and behaviors. The first thing that made my husband all giddy was the chance to wear female lingerie, makeup, and to dress up all nice and pretty. Check out a shortlist below of all the things you could have your sissy wear:
I like choosing these for him, but sometimes I let him pick the clothes and heels he likes. He is especially fond of gentle thigh-high stockings with lace around the edge and glittery pumps. 
Sometimes we play dress up. I order my sissy to dress like a slutty secretary, trashy whore, a young, innocent girl… It all depends on how I feel. It’s truly something else, watching your husband in a frilly skirt with his dick in lace panties already hard from just wearing a female outfit.
I sometimes even get some my used panties for him to wear, when I’m feeling extra kinky.
A traditionally female look is one that includes long hair, of course. It may not be practical (or feasible) for your sissy to grow his own hair out, so wigs are the next best thing. During our training, we have gathered a collection of wigs, from regular ones – just simple long, red hair wig , for example – to those bolder in both style and color. It is completely up to you what type of wig your sissy will wear, so try it all out! Choose something blue or pink or, my favorite is this ash blond and my other favorite is this beautiful pink wig . It’ll look hot and beautiful at the same time. 
Sissies aren’t hairy. They don’t grow beards and they have smooth, hairless bodies. If your sissy is up for it, get him thoroughly waxed. It can be a thing you arrange an appointment for, but it can also be a part of foreplay or a chance for you to play with his pain tolerance a bit. Waxing isn’t inherently pleasurable, but it can be if you want to make it so. 
For a more permanent solution of the hair conundrum, I suggest looking into laser hair removal. It’s not as cheap as waxing, obviously, but it gets rid of hair more permanently and without any stubbly traces afterward. 
Once you get the look down, it’s time to move on to the actual acting. Your sissy will be grateful to learn how to be more feminine, sensual, and overall, how to be the best girl he can ever be.
My husband and I always knew this was our ultimate goal: get him ready to be dominated by another man. However, this may not be everyone’s cup of tea, so consider cock training an optional part of sissy training. Only proceed with it if both of you are open to the idea. 
I was fortunate in this area because my bisexual husband already had experience with giving head. Nevertheless, I made sure he fine-tuned his technique and practiced a lot on a strap-on cock I wore. It was all about that tongue action and eye contact and, of course, can’t forget the balls! You should also learn my little trick to giving deep throat blowjobs .
This was my favorite part of the training. It took us months to get there, but when it was finally time, I couldn’t wait to get started. At this point, my husband hasn’t been penetrated anally in years, and I was excited to be the first one in a long time to slide something inside his pretty smooth ass. 
For this part of our training , we used suction cup dildos at first. He liked to ride them so much, bouncing in his lacy lingerie like a pro while I recorded him for our personal collection. 
Then, once he got used to the feel of a dildo, I dominated him with this pegging kit . Fucking my husband in the ass is still one of my all-time fav things to do in life and not much will ever come close to the feeling of him unraveling on my strap-on. Like a good little sissy that he is.
Even though I obviously can’t ejaculate into anyone, there are ways to prepare your sissy for the feeling. Use this ejaculation dildo or squirting dildos as they are sometimes known. They are much like regular dildos, only with a canal that goes through the shaft to the tip and a convenient syringe to squeeze cum-like liquids through that canal. You can also buy special lubes that look and feel like real semen to simulate the experience.
You can learn how to make your own cum to use in your ejaculating dildo here.
At last, my little sissy was ready for the real thing.
It was time to introduce a real man into the equation. I took some neat shots of my sissy, of his plump ass in a thong and his best seductive gaze, and then I posted them on sissy personals on Reddit . 
I was very upfront about what I wanted and what my sissy was like, saying he successfully completed his training, was a pretty little obedient pet (which was true), and that he was ready to be dominated by someone who knew how to make good use out of him.
To my surprise, more than one male dom said he was up for the task, and it wasn’t long before I chose the one I felt worked for us the best.  
Since then, we’ve met a number of different men who would sometimes only dominate my husband, and sometimes they would have sex with me after, with my husband watching. 
When it’s my turn to have some fun with the other guy, I lock my sissy up in a cock cage, this exact cock cage , and make him do clean-up after my lover and I are done. Some of his best orgasms come after I finally take off the cage. 
Here’s a full list of cock cages , so you can find the perfect one.
When we found the right guy to fulfill our fantasies, we knew there was no turning back. The meeting was arranged, the details have been hashed out. Our male dom was completely on board with everything we wanted, and he was actually excited to make my sissy submit, which in turn made us excited as well. 
I didn’t know whether or not the training would hold up. I was confident in my sissy, but I still hoped he wouldn’t let me down. 
Our first male dom was older than us, tall and handsome, and his commanding presence was undeniable. My sissy immediately knew how to act, how to shyly avert his gaze, how to let the male dom touch him and pull him closer and inspect his lingerie that we bought just for the occasion. 
It wasn’t long before the dom was pushing into my sissy’s ass, with the sissy moaning so beautifully. I had taught him well. 
That first time, I wasn’t interested in having sex with our partner. I wanted to take my sissy home, riding on the high of our encounter, and I wanted to break him completely. I wanted him sobbing as I rode him to my own orgasm, and that’s exactly what I got. 
Needless to say, we both couldn’t wait for next time.
When it comes to the necessary toys and tools to train your sissy, the selection can get a little overwhelming. There are thousands of products to choose from in any category, and it may take a while before you decide on the ones you like. 
To make matters easier, the toys I list here are the ones I used and the ones that worked for us. Check them out and see if some catch your eye. 
The best thing about this cute pink cage is that it can be worn all day long! You can play with your sissy as much as you want before he earns his release from the chastity, and the longest we’ve ever gone was 13 hours. Made from medical grade materials, this cage is safe and hypoallergenic, and I’m honestly a little bit in love with it. 
So we’ve tried dozens of strap-ons. Some of them were okay, some of them were not convenient at all, and through all of that, I somehow found that this one was the best. It’s simple and with an easily adjustable harness, and the dildo is perfectly shaped to hit my sissy’s P-spot until he can’t take it anymore. Don’t forget the lube, of course!
When you’re just starting the anal penetration part of your training, it is important to go slow. My sissy first started with this relatively small pegging dildo , 5 inches in insertable length and 5 inches in circumference. Great for beginners to get used to the stretch. 
Just before we were due to meet our first male dom, my sissy could take in all of this massive king-sized dildo that is 8.5 inches long and 7 inches in circumference. A true champion of anal penetration; once your sissy gets used to this, he’s ready for a real dick. 
I love a good innocent white on my sissy. He loves lace and garters, and so we decided that this would be ideal to wear around the house for hours on end. He gets in trouble if the white gets stained, which makes our days a lot more interesting. The stockings are comfortable and hug his thighs nicely, making for a great overall effect. 
I know it may not be common to use a metal plug, but hear me out: you can make it cooler or warmer, depending on if you keep it in the fridge or in warm water before you decide to use it. This temperature play makes my sissy crazy, and I know he loves it when I slide a cold, hard butt plug between his cheeks. I love it when he bends over and I see the cute sparkling jewel inside his ass. A great moment in my day.
It’s not often that my sissy wears fake breasts, but we have been known to use them on occasion. These are D size, meaning quite big. They’re made of medical-grade silicone, making them jiggly and soft to the touch (and also safe). They’re self-adhesive, so you don’t have to use any straps or tape to keep them up. 
Alongside everything I listed, here are some more options for you to consider. There’s a vibrating dildo, a pair of schoolgirl socks, a cute collar for your sissy to wear even outside, a hot lace thong, and a luscious wig.
I keep this list updated and when I get a new favorite I’ll add it here.
For more information on sissy training and how the lifestyle works – as well as to find people who are looking for a dom to train them – you can check out any of the subreddits below. Reddit, in general, is a great place to join communities of like-minded individuals who will welcome you with open arms. They’re great for exchanging stories, asking questions, and connecting with other fans who are practicing the lifestyle. 
Finally, to find doms or sissies in need of doms, try sites like the Adult Friend Finder and Fetlife . They are free for you to use and there are thousands of kinky people there. You can meet other sissy users and engage with them, and also arrange to chat over Skype or even meet in person! These online communities are great resources to have when you’re starting out, but also when you’re just keen on talking about your favorite fetish. 
I hope my experience with my sissy and our training process will help you figure out your own. Just remember that everyone’s journey is different; you don’t necessarily have to go through all of these steps to get the same results (if you want the same results in the first place). Maintain open and honest communication with your sissy, and everything should be fine. Have fun and stay kinky!
I’m Willow, I’m Brandon’s girlfriend and we run this blog together (with the help of some friends). We both have an open relationship and both love being kinky (I mean who doesn’t?). I love writing, music and my Womanizer. If you have any questions leave them in the comments.
my boyfriend and i have decided we want to do this…. my problem is…. i don’t know how to act as a Dom. i have always been the submissive type in the past. i don’t know how to be sexy and dominant at the same
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