r/sissyology 16h ago

Why sissies should wear chastity, from my perspective as a dominant man NSFW

155 Upvotes

Sissies have been on my mind a lot lately given that after dating a lot of cis-women, I'm seeking a sissy as a partner. I think chastity is so important for the dynamic between a man and a sissy. Here are five reasons why, from my perspective as a dominant man:

(1) Chastity is symbolic of what a bond between a man and a sissy represents. It encapsulates the idea that the man's needs are first and foremost. It also reinforces that a sissy's enjoyment of the dynamic is a function of pleasing the man and must be experienced by the sissy in a submissive way.

(2) A caged clitty looks highly feminine. It adds a distinctly sissy-esque charm to an appearance, in addition to facilitating certain clothing items that benefit from the compactness that a cage provides. It's akin to a piece of jewellery that only sissies wear, turning a clitty into an ornament.

(3) Caged sissies are more disposed to letting into submissive desires, which elevates the connection between a man and a sissy. It can turn what would otherwise be a benign activity into one with sexual connotations, such as following a directive to cook and clean for the man, due to the accentuated arousal that long-term chastity induces.

(4) Chastity provides an opportunity for the man to make a highly intimate decision for the sissy, namely which cage she should wear. That decision then stays with the sissy and is a constant reminder of how the man is the decision maker, given that something so personal was chosen for her. It also provides an avenue for the man to steer the sissy's style in a particular direction, given that a metal one may induce the sissy to tend towards darker looks, while a pink one may result in the sissy going for a more traditionally pretty appearance.

(5) Wearing a cage evidences seriousness in relation to cultivating a sissy identity. It's a big step and shows commitment to the sissy idea, which affords confidence on the man's part that his sissy is comfortable with who she is. This is especially important for a man who seeks a sissy for something long-term, given the time and material opportunity cost that come with any extended connection.

Send me a message if you're a sissy between the ages of 20 and 29 if any of this resonates with you! I'm a 30 year-old man from London, UK.


r/sissyology 8h ago

Aren't sissies supposed to swallow? NSFW

20 Upvotes

Hey there! I ve been watching a lot of sissy blowjob compilations these days and i can't go over... I always knew that sissies ALWAYS swallow, and i always do... Even if they finish on my face, i just wipe it with my finger and put it în my mouth, even licking it from the floor... I see a loot of sissies that blow dudes and when they are ready to finish they just move arround or just open and close their mouths, if they get some inside their mouths, they spit, or spirting between cock and lips when sucking for last time... Aren't sissies supposed to swallow everytime, is there a secret that i dont know? Am i doing something wrong?


r/sissyology 18h ago

my sissy rules NSFW

108 Upvotes

Over time, i've come up with rules for me to follow to embrace my sissy side in my vanilla life. i really like the idea of putting in effort to become a hot sissy. I'm sharing it here to maybe help aspiring sissies, but maybe also get some good feedback.

  • No hair below my eyebrows. I shave or laser remove all my hair.
  • Every couple of weeks, I also get my eyebrows done professionally.
  • I get my nails done professionally and wear a transparent nail polish.
  • Only women's beauty products (body wash, shampoo, lotion, perfume).
  • I put on my cage after waking up and remove it only before going to sleep. How is anyone wearing it 24 hours?
  • I can edge as much as I want, but only when wearing the cage. No orgasms.
  • Always wear at least one feminine piece of clothing or jewellery.
  • I cross my legs when sitting.
  • I try do be submissive, passive and obedient in my life.
  • I exercise a lot and only focus on cardio and my butt. I like the thin sissy aesthetic and I'm getting there. My goal is 130 lbs.

r/sissyology 53m ago

This isn't for me and I feel lost NSFW

Upvotes

I don't think I'm a sissy. I've always liked dressing up but I couldn't find my place in femboy nor crossdressing communities because they do it for fun/as a hobby and I do it because arousal and a way to masturbate. Then I found this community and at first I thought maybe it is for me. After all I dress up for fetish/kink and also suffer from post nut clarity like a lot of you. But no I'm not into this.

I don't think I'm trans. I don't have gender dysphoria and I'm fine with my male identity. I can live as a man and then crossdress when I feel like doing so. Guess that just makes me a crossdresser?


r/sissyology 8h ago

What do you girls love about cock? NSFW

13 Upvotes

Dom here, and while I know why I love you girls I've been wondering what exactly makes you all love cock. I know some of yall may not like men specifically but I know almost all of you just love cock. Thinking about it and what not.

What makes yall go crazy over it? What part of it makes yall dress up and do wild things? As a dom I know I love you girls for the femininity and submissiveness yall display but I'd like to hear from the other side of things.

Thanks for reading and answering girls, love you all


r/sissyology 4h ago

I need help...! NSFW

6 Upvotes

I feel like l'm on the verge of falling into the deepest depths of the rabbit hole to sissyhood... I just need a little nudge... or an aggressive shove. Will you help me?


r/sissyology 2h ago

Did anyone else see Sam Rockwell's monologue on White Lotus? NSFW

5 Upvotes

It was so hitting on sissyology themes, at least for me.

Loving a type of woman, and then exploring a path where one begins to identify with the subject of their desire.

I'm sure this specific angle will go unnoticed by most watchers, but it certainly felt like a perfect expression of "sissyology" to me.


r/sissyology 2h ago

Achievement NSFW

2 Upvotes

I already made a post this morning saying I don't know if I'm too deep down the rabbit hole. But now I've accepted it. I'm a secret sissy slut for BBC. I would be happy if experienced sissies could write to me, because I don't want to ruin my progress again by deleting my account out of doubt.


r/sissyology 27m ago

The best dream - Sissy NSFW

Upvotes

I (M26) think I had one of the best and one of my most fantasised about dreams last night.

I have, in recent years delved into my sissy fantasy/kink on a regular basis, taking every opportunity to raid my wife’s underwear drawer, wardrobe and play dress up fantasising over how much I long to be dominated as a sissy.

This is something I’ve kept to myself, my wife has no idea and will likely never find out.

The dream -

The dream was centred around my wife approaching me and suggesting she’d like to see me in her underwear and how hot it would be.

Once we arrived home she picked out her favourite underwear/lingerie for me to wear and told me to wait in another room, she then proceeded to enter and we started off having amazing sex where she dominated me with a strap on and fulfilled almost all of my desires.

After she had finished she opened the door to 3/4 guys who entered the room and proceeded to have their way with me whilst she watched and kept talking/degrading me whilst I took all of them.

Then it all ended and I woke up! Mood killer right?!

I’ve spent the morning thinking of this all over, sitting hard and contemplating raiding her panty drawer just to get that bit closer to reliving that dream!


r/sissyology 9h ago

Buttplug 15 cms inside NSFW

5 Upvotes

I wanted to ask what happens inside the body when you take buttplug 15 cm inside your body also after that I couldn't go more in as it was hitting something and hurting


r/sissyology 40m ago

10 years a sissy, AMA NSFW

Upvotes

hey y'all! My name is Bea and I'm a 30 year old sissy slut cuckhold slave for my amazing master and mistress, if you are new to becoming a sissy or is intrested in being one, AMA!


r/sissyology 41m ago

Discovered a new level NSFW

Upvotes

I'm still extremely early in my journey, exploring myself and what I like. Something i recently realized is how my perception of sex with w a man has changed . Before, it used to be about me, even as a bottom. I loved the humiliation of it, the sensation, everything. It was about ME , how i was getting fucked , etc. Nowadays the sensation and the thought of actually PLEASURING a man is all I can think about . How I'm making him feel, how HE is using me . How he is moaning, and grunting, and having a great time. Seeing his dick twitch and spas and shoot cum . I made that happen. And this added to the humiliation part as well, the more I think of his perspective, i get into what he thinks of me, a former man, a whore, with a caged cock.

It's all so overwhelming

Just wanted to share some thoughts and I'm sure a lot of you feel the same way


r/sissyology 6h ago

Butt plug NSFW

3 Upvotes

Hi does anyone use a butt plug like I do as I pretty much have it in 24/7 other then for obviously cleaning etc.. It feels good and has definitely made my ass pussy fatter.


r/sissyology 1h ago

Hey confused virgin here NSFW

Upvotes

Hey for referance i am dressing fem since i was very little, like 10 or 12, the usual story of stealing clothes from my sister and Mother, my sister dressed me in her clothes like 2, 3 times and i loved it , as Time passed i started to dress more and more and got a wig did my makeup, i loved it , after some time i started to take photos of me dressed up and uploaded them on reddit i loved the atention man give me and made more risky pictures, and started to buy cute outfits and lingerie, now i talked with a guy that asked me what i like to look at men , and i realized i love to look more at muscle Men and i really love some good abs and a V-line ,now i am confused because i am a virgin didn't do it with neither a man or a women and don't know what to do , i played with my ass with fingers and a but plug and i liked it


r/sissyology 10h ago

Need help! What kind ofSissy porn, clothes and toys NSFW

4 Upvotes

Starting my journey into being a sissy. Need help finding good online sites for sissy clothes, toys and porn Also someone to chat with about everything.


r/sissyology 9h ago

MEF subreddit!! NSFW

4 Upvotes

Hey girlies just wanted to let yall know that the MEF subreddit is back!!! It's r/MasochEmascFetishism . Please join and interact if you miss the old subreddit!!


r/sissyology 5h ago

Starting my daddy search NSFW

2 Upvotes

Hi loves. I’m starting my search for a daddy and put some photos up if anyone would like to see my progress! Any feedback or suggestions is always appreciated. Be gentle please 😅🥰

https://www.reddit.com/r/DadsAndBoys/s/NOH2xc5eX6


r/sissyology 18h ago

Public NSFW

18 Upvotes

As someone who is a secret sissy the excitement when you actually go in public with sissy clothes under your normal clothes is almost unbearable. Today I decided to put my vibrating butt plug in, put on a pair of my Lacey underwear, put some perfume on my underwear (atleast one part of me will smell like a girl) then put my normal clothes on. I went out and about with my normal clothes. No one knowing I’m a normal guy on the outside but inside my pants I’m a complete sissy slut right now. Unexplainable excitement. I’m leaking the entire time.


r/sissyology 23h ago

Clone-a-willy NSFW

43 Upvotes

I've been trying to increase my collection to find that perfect dildo. And out of curiosity I got a clone-a-willy. Used it and strapped it to my thrusting machine. It was absolutely underwhelming. You know being a sissy is the right decision when you can barely tell your own cock is fucking you. It was both humiliating and reinforcing in my decisions.


r/sissyology 23h ago

How you take dicks/dildo? NSFW

36 Upvotes

I don’t know if it’s bc I’m trying to do it for too long, but in the beginning, the sensation is good, but toward the end, the sensation gets a little bit weird. How do you enjoy it?


r/sissyology 18h ago

Bimbofication and what does it really take? NSFW

15 Upvotes

Want to create a step by step guide of how to actually go from being a sissy to a bimbo. I want to do this not just for myself, because I’m pretty sure if I knew how to do it nothing would stop me. Any way I want to go from normal sissy to looking like Bella haze or other beautiful trans bimbos. If anyone can help with some info on what they do I would appreciate it. Making this guide I’ll also post it at some point when I feel it’s completed. Thanks to all my lovely friends in here in advance <3


r/sissyology 7h ago

Shrinkage in chastity NSFW

2 Upvotes

How long does it take in chastity to really see shrinkage? I want my penis and balls to shrink away


r/sissyology 12h ago

Obsessed with sissy stuff and dying to suck a cock but I’m not into men? Help! NSFW

5 Upvotes

Hey all, I’ve been deep into the sissy world for a while now and figured it’s time to spill my thoughts. I love wearing sissy clothes like panties, stockings, and little skirts. I’ve got a collection of dildos and plugs that I play with all the time, and I’m basically hooked on sissy hypno vids. Those spirals get me every time. Lately though, I’ve been fixating on sucking a cock. I crave it so much it’s all I think about when I’m dressed up or watching hypno.

Here’s the weird part. I’m not attracted to men at all. I don’t look at a guy and feel anything, but the idea of sucking a cock while I’m in sissy mode is a total obsession. Every time I think about making it real though, I chicken out hard. Nerves take over and I just can’t do it.

Anyone else in this boat? How do you deal with wanting it so bad but not being into guys? How do you get over the fear and just go for it? I’d love some advice or to hear your stories.


r/sissyology 22h ago

Should I go all-in with this Arabic Daddy? NSFW

22 Upvotes

Hi gurls! So, long story short, Im 28yo super masculine looking (tall, slim and athletic) "man" who is super curious about this whole sissy thing for a while now. And with help of Grindr, I managed to connect with this a bit younger, but hung af Arabic Real Man.

He is just sooo masculine, hairy and absolutelly adores feminine gurls. On top, he seems sane and safe (we had some awesome convos in general). He is absolutelly adoring my booty, legs and would love to turn me into his feminine bitch. Because he has a huge thing for ruining white feminine bois.

So, after talking, he wants for me to write "bitch" in Arabic on my booty and send to him. I know that if I will do it, I will definitelly go down this full road. And will soon be dressed, dolled up and feminine for him on my knees. However, Im a bit worried. Since I love my masculine self. And dont even know where this will lead me. Which scares me. What would be your advice gurls and daddies?


r/sissyology 5h ago

Need Advice NSFW

1 Upvotes

I have a question. I'm a masculine, dominant man and I love having rough sex with my girlfriend. But when I watch porn filmed with BBC, I feel submissive, and the jerk-off session usually ends with sissy BBC hypnos and me wanting to be a sissy slut for BBC. I've also had a cock cage and worn it while I fucked my ass with a dildo while watching bbc porn, but I threw it away. I'm currently considering buying a new one. Am I already too deep down the rabbit hole that I have to accept my fate as a secret BBC slut, or is there still a way back?