Sissy Train

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If you’ve been following our stories and guides, you’ll know by now that Tim and I aren’t your ordinary married couple. We are one of the most creative, fun, and open-minded individuals you’ll ever find online and offline.
We’ve done so many pleasurable and exciting things inside and outside our bedroom. We like doing something different and extreme now and then. But do you know what we love the most? It’s the fact that we can share our stories and teach you some tips and tricks based on our experiences!
We’ve done a lot of kinky things but if there’s one thing I will never forget it has to be when I taught Tim how to be a sissy husband. It was something I’ve been longing to try for a very long time so when he finally said yes, I felt like I won the lottery. Tim isn’t gay at all though I’m bisexual. He just can’t say no to me especially when he knows it’s something we will both enjoy doing.
I’ve read a lot of sissify husband stories before opening it up with Tim. And I wanted to make sure I have all the facts so that he couldn’t say no. To my surprise, he was excited about doing it. He said he’d heard about it and he was waiting for me to bring it up. It didn’t take long before we got into sissy husband training and here we are sharing our experience with all of you.
‘Sissy’ is no longer just an expression or a type of subtle insult. ‘Sissy’ is a phenomenon- a practice, and a very unconventional one at some point. This Sissy phenomenon is where adult men willingly put themselves into a process of tedious and persuasive transformation where they are feminized (mostly by women) through various methods, as they gradually let go of their masculine traits and behaviors. Plus, it gets very kinky given that some participants only do it because they find erotic pleasure and satisfaction in the dynamic.
There are lots of grey areas in this field given that this particular exercise can both be personal and political- depending on one’s angle. In hindsight, it may give a female-empowering impression (since most of the dominants are females), however, it can also be very misogynistic. It’s a paradox, and like most paradoxes, it’s interesting.
In some way, I see Sissy Training as a kinky dynamic mixed with an erotic power play, although Sissy Training doesn’t necessarily have to be erotic. Some even consider this as another form of BDSM but I think this is a whole other entity. Sissy Training is when a biologically male individual decides to undergo this tedious and systematic method of transformation into someone feminine.
Sissy Training or sissification is the process of feminizing a masculine individual and though there are certain people and sources that may refer to this as a forced feminization, take note that like any other dynamics, Sissy Training can only be established with consent and only consenting individuals are allowed to undergo such process which tends to put physical, mental, and emotional strain and pressure on the Sissy (the submissive male who willingly puts himself in the process), all of which are essential in achieving the goal of the dynamic.
During the process of sissification, the Sissy or the submissive male partner is bound to follow all the exercises and training that the dom has set. There will be cross-dressing, makeup application, domestic chores, and all other hyper-feminine things under the sun. There are also times where mannerisms and manner of talking are being altered for the Sissy to adopt female traits and actions. Some even go to the extent of shaving off their hairs, changing their posture, playing with sex toys (dildos, cock rings, and butt plugs), and engaging in a-levels (most of the time, sissies are only allowed to have a-level orgasms).
The whole thing works similarly like BDSM and other role-playing and power-play related dynamics. There are punishments and rewards although I prefer ‘rewarding’ or bringing positive reinforcements to have a better and faster output. Yes, there are punishments in here too and mostly consists of humiliation and some sissies are only motivated by the erotic pleasure and satisfaction they find in humiliation (as I said, it’s partly a kink) and that is where things become misogynistic in the implication that something is humiliating and pitiful in being a woman or in being feminine.
Also, some may find overlapping or similar aspects among sissies and transgender. Well, in hindsight, we can say that they do but an in-depth look will tell us otherwise. Transgenders undergo a transformation process where the output is going to be more permanent than that of the Sissy Training. Transformations in Sissy Training are far more temporary and can always be reversed whenever the Sissy wants to. Unlike trans, sissies do not necessarily try to find their true identity or orientation. Some sissies do the transformation due to personal and political reasons due to repulsion to one’s masculinity, and the desire of redemption.
So I talked Tim into undergoing Sissy hubby Training. We like role-playing sex but he never experienced being a Sissy. For his first “training session”, we decided to hit several birds with one stone. First, I asked him to change his physical appearance. We started by shaving off his chest hair and legs. Then, we took a shower together so I could rub him clean.
When he was done, he put on the sexy red lace underwear I got him. He looked funny at first but when I took in the sight of him from head to foot, I got a little horny especially looking at his crotch. His cock and balls are very visible underneath the thin lace fabric. Then, he wore this very short, skin-tight little black dress that hugged his body like a second skin. He also wore black sandals to match his outfit. Finally, he wore the cotton candy-colored wig I bought for him.
I’m bisexual so when I saw him dressed as a woman, I felt my pussy getting wet with my vaginal juices. Tim has that effect on me even if he’s dressed like a woman. He got into being feminine with the way he walked and sung his hips as he did his chores. I also gave him a sexy name, “Tamara”, which he also loved. So “Tamara” swept the floor and did our dishes. She also did our laundry.
“I think I deserve a treat after doing the chores,” Tamara said, twirling a few strands of hair around her fingers. “Why don’t we go rest in the bedroom for a while?” She winked at me and didn’t wait for my response. She carried me to our bedroom and dropped me on the bed. I knew exactly what she wanted. So said and done, I got up and took out my strap-on dildo.
I took off Tamara’s clothes and she helped me get rid of mine, too. We started kissing each other hungrily and when we were both ready, I put on my strap-on and positioned myself behind her. I made sure to put a lot of lube on my sex toy before slowly putting the dildo inside her tight ass.
Tamara was moaning and groaning as I pushed and pulled inside her ass. I felt hot myself but I could wait later. Right now I just want my partner to feel like a real woman being dominated over by a “man”.
I pushed harder and harder while my other hand caressed her cock. She told me she’s coming and I felt her body shuddered as her rectal muscles tightened around the dildo. I slowly took it out of her a few seconds later.
Afterward, I looked at Tamara and noticed there was semen on her belly. I wiped some off with my finger and brought it to her lips. She didn’t hesitate at all and started licking my finger.
“Did you like it?” I asked playfully.
“Of course, honey. It was amazing. Let’s do this regularly.”
I couldn’t have been more proud of him.
If you think it’s hard to turn your husband into a Sissy, think again. It’s easier than you thought. Nowadays, men are very resourceful and imaginative when it comes to sex especially in pleasing women. They’re willing to do whatever they want to ensure that they keep their partner happy and satisfied.
Tim and I started Sissy Training a while back. Just like many couples, we were hesitant at first, I in particular. I wondered if my husband would like to be feminine for a chance to have a feel of what it’s like to be in my shoes. Luckily for me, Tim is very a cooperative man who loves her wife to bits. If you and your partner want to try Sissy Training yourselves, here are some tips on how to turn your husband into a sissy:
Whenever we want to try something different, Tim and I discuss everything with each other first. That’s exactly what we did when we started Sissy Training. I can still remember what happened at that time. We were lying on our bed after steamy lovemaking when the idea popped into my head. I asked him what he thinks about Sissy Training and being feminine. He said he has nothing against it and as if reading my mind, even asked if I wanted to give Sissy husband play a try.
I was surprised because I’ve known Tim my whole life and he’s far from being feminine while I’m a confessed bisexual. We discussed it for a while and we both agreed to do it on a part-time basis or only when we feel like it which is fine by me. We also set boundaries especially on what he can do and what he doesn’t want to do. I love that we have mutual respect and consideration towards each other. I don’t like forcing him to do something he doesn’t want to so it’s best to set the rules once and for all before doing Sissy Training.
For me, the most exciting part about Sissy Training is buying my man sexy lingerie. Though it would be nice seeing Tim in my bra and panty, they’re too small for his size. Since I’m not very sure about his size, I decided to buy him lingerie from a physical store in a mall near our home. I know the size of his waistline and chest but it was still a challenge for me to find the right sizes for him. It was so much fun!
To start, I bought him a pair of sexy lace lingerie, just in case, they don’t suit him well. Fortunately, they were perfect for his frame and soon I started buying him some sexy pieces online. I like to buy those made from different materials like lace, cotton, latex, and leather for those hardcore nights.
We want Tim to look as girly as possible and the best way to do so was to get him a wig. I think someone as handsome as he is will look gorgeous in a wig. I was searching online for one when I came across the Leg Avenue Pink Bombshell Long Curly Wig in the shade of cotton candy pink. Eventually, we bought other wigs to mix and match with “her” underwear.
You know how it is with women. We want to look as flawless as possible and that means shaving or waxing those unwanted hairs on our legs, armpits, and private parts. Tim has lots of chest hair but when we started Sissy Training, he let me shave them off.
He also has hairy legs so we made sure he shaved those, too. I didn’t have to worry about giving him a bikini wax because he always made sure his cock area is clean and hairless.
One of the most important elements of Sissy role play is to make sure that your husband acts like a real woman. To do this, you need to train him to be more feminine. Letting him wear a bra and panty and a wig is a good start but Sissy Training goes beyond the outward appearance. He also needs to act the part.
There are many ways to do this and my favorite is to let Tim wear dresses. This helps him get into the part. Once he has his dress on, I also let him wear sandals or ladies’ shoes. I don’t let him wear high heels, though, because he’s a big man and the heels might snap.
Once he’s all dressed up, I teach him how to do his makeup. First, I let him try my skincare routine. He starts by washing his face using my facial cleanser, applying toner and moisturizer, and then makeup. It’s nice watching him use my cosmetics especially with the way he crosses his legs as he gently applies some eye shadow with an applicator. Lastly, I let him use my perfume to make him smell feminine.
Did you know that having a Sissy man has many benefits? One of the perks is that I get to rest from all the work inside the house. During his “training”, I let my Sissy husband do some household chores.
In addition to wearing his wig, underwear, dress, and sandals, I also let him wear an apron while sweeping and mopping the floor, washing dishes, cooking, and doing the laundry. Looking at him doing these things like a pro makes me horny!
I love giving my husband a blowjob because it makes me feel superior. Just imagine having your man’s cock in your hand and mouth and the pleasure he receives depends on you.
This is why I insisted on giving Tim a short Training on how to give a blowjob. I used my dildo to show him how I do it with his cock. He’s an attentive learner and when it was his turn to demonstrate, I felt so horny I begged him to take me right there and then.
This came as a breeze for Tim and me because we’ve done pegging for years. If your man isn’t into it, it’s time to let him take on anal Training. This is easy to do as you’ll only need a strap-on dildo and a good lube.
In our case, we like using Lovehoney Advanced Unisex Strap-On Harness Kit with 7 Inch G-Spot Dildo. This harness and dildo set is easy and safe to use.
What’s all that Training on how to give a blowjob when you can’t make your partner eat his cum? I like eating Tim’s cum but he never tried eating it himself. Well, I told him that if he wants to go all the way with this Sissy play, he might as well learn to eat his cum.
I gave him a good old blowjob and after that, I told him not to cum in my mouth. Instead, I let his juice spill all over his tummy and told him to use his fingers and lick his semen. It was very weird yet sexually pleasurable at the same time.
Sex and penetration are just as important as the rest of the exercises in Sissy Training, and though this field is optional to others, I find this very vital in the process of emasculation. Plus, some Sissy husbands wanted this.
As I said, it’s a kink and like any other unconventional and sexy stuff, we need the aid of props and in this case, strap-ons, dildos, and cock-rings, as well as butt-plugs are going to be our go-to sex toys. However, one can still utilize BDSM toys, just as long as both parties are okay with the idea.
Also, the CB-600 Male Chastity Cage Kit can be very useful in trapping your, or the sissy’s manhood to keep them out of action. It’s made with medical-grade polycarbonate that’s hypoallergenic and designed to be ergonomic for prolonged wear. It’s transparent, breathable, and customizable. Also, it comes with plastic padlocks, storage, and lube samples. Perfect for chastity plays.
When it comes to cock rings, the Pure Silicone Stretchy Weighted Cock Ring is going to be perfect for any ball plays during your kinky sessions. It’s easy to use, comfortable, and very versatile. You can use to your cock or your balls. Not to mention that it’s lightweight.
Silicone Urethral Sound Set can also be considered although it does get the penis involved. There are about six thicknesses to choose from and is suitable for any gender. Just don’t forget to sterilize the sounds before and after use.
Somehow, it doesn’t matter who, as long as they are willing to do it. Although, some cuckolds and bulls (individuals who get aroused in knowing that their partner is sleeping with someone else) do engage in this dynamics sometimes. It’s a bit twisted, but all fetishes are.
With the aid of the internet, it’s not that hard to find one even when you want to do it discreetly. For one, there are loads of communities and forums out there that can help you in your search and Reddit is one of the perfect places to find them. There are Reddit communities (sissypersonals, Sissies) that provide those aspiring sissies to search for their domme. They post raw and sexy pictures here.
Visiting adult websites and watching Sissy porn videos are also good choices. I’m pretty sure that Adult Friend Finder and FetLife is going to help you in many ways. One can find their match or those who share the same interests with them. Plus, all these places are judgment-free zones. These are perfect for those with unconventional interests.
My husband is a sissy! And we never expected to have so much fun. In fact, we enjoyed it so much that every time we do it, Tim gets more excited than I am. We have learned so much from doing it ourselves, especially him. He said he learned to be more respectful, understanding, and caring towards me. In return, he becomes more attractive in my eyes.


This post first appeared on My Sex Toy Guide, please read the originial post: here
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If you’ve been following our stories and guides, you’ll know by now that Tim and I aren’t your ordinary married couple. We are one of the most creative, fun, and open-minded individuals you’ll ever find online and offline.
We’ve done so many pleasurable and exciting things inside and outside our bedroom. We like doing something different and extreme now and then. But do you know what we love the most? It’s the fact that we can share our stories and teach you some tips and tricks based on our experiences!
We’ve done a lot of kinky things but if there’s one thing I will never forget it has to be when I taught Tim how to be a sissy husband. It was something I’ve been longing to try for a very long time so when he finally said yes, I felt like I won the lottery. Tim isn’t gay at all though I’m bisexual. He just can’t say no to me especially when he knows it’s something we will both enjoy doing.
I’ve read a lot of sissify husband stories before opening it up with Tim. And I wanted to make sure I have all the facts so that he couldn’t say no. To my surprise, he was excited about doing it. He said he’d heard about it and he was waiting for me to bring it up. It didn’t take long before we got into sissy husband training and here we are sharing our experience with all of you.
‘Sissy’ is no longer just an expression or a type of subtle insult. ‘Sissy’ is a phenomenon- a practice, and a very unconventional one at some point. This Sissy phenomenon is where adult men willingly put themselves into a process of tedious and persuasive transformation where they are feminized (mostly by women) through various methods, as they gradually let go
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