As a sissy, whats the biggest size you take in your ass and it can be anything like dildo, strapon (pegging), man's cock, shemale cock etc. Let's start with me I take 10 inches strapon during pegging and 8 inches shemale cock in my ass. what about you.

This guide is primarily focused on those of us that are secret sissies. Whether that means no one knows or perhaps you have an accepting significant other but don't want it running into your "normal" life or anything in between. Because of this, I think a lot of us are in the position where we can't make any permanent changes to our appearance because of the need to return to "normal".

I love to search out sissy tasks and guides but I have always been vexed by them starting out with something like shave your body or grow out your hair. While I would love to be able to do these things (temporarily), it simply is not possible.

So I started to think about all the various things we can do to feminize our appearance and rank them into different categories of how noticeable they are, specifically in public.

I recognize some things may be dependent on where you live (cultural norms), on the climate you live in and your personal build. This list is based on being in public but needing to return to "normal." It also assumes a certain level of discretion, obviously you can get yourself caught with even the simplest of items if you aren't being aware.

Please chime in with any disagreements or additional things to add.

Low Risk (shouldn't be noticeable in public and/or back in "normal" mode)

• Panties (be mindful of what pants you are wearing)
• Bra (specifically certain types of cami, sport, bralette and balconette which are pullover type bras and do not feature a back clasp. They also need wider straps over your shoulder that do not feature slider adjustments. Finally, you should remove any padding or forms so it sits flat.)
• Stockings / tights
• Body stocking/ body suit / leotard / teddy with other clothing on top (No sleeves, no collar, no around the neck straps and should look for one with wider shoulder strap)
• Socks (short socks, long socks but be mindful of where the bottom of your pants fall)
• Yoga pants/leggings (under other pants)
• Majority of tops (with hoodie or coat)
• Butt Plug (non vibrating)
• Chastity Cage
• Body Writing
• Bridal garter
• Toe rings
• Fake belly button ring (dependent on outwear)
• Anklet (with long pants)
• Fake tattoos (be careful not to get really good ones that are difficult to wash)
• Camisole (look for ones with wider shoulder straps)
• Shapewear (without pads, most styles are designed to be discrete)

Medium Risk (shouldn't be noticeable from a distance but could be noticeable up close but wouldn't be noticeable back in "normal" mode)

• Bra (other types of bras not already listed in the low risk category but must be combined with larger hoodies or coats)
• Corset/Bustier (same advice as for the bras)
• Garter Belt (because of the adjustment straps and clips, thicker pants should be worn)
• Jeans (hugely dependent on fit and style - could easily be high risk if not careful)
• Shoes without a heel and androgynous style
• Body stocking / bodysuit / leotard / teddy with other clothing on top (other types not listed in the low risk category, depending on style this could also move into high risk)
• Nude lipstick
• Vibrating Butt Plug
• Fake nipple rings (dependent on outwear)
• Necklace (this can range from low to high risk, hugely dependent on style of clothes)
• Body Chain (similar to necklace, this can range from low to high risk)

High Risk (noticeable from a distance and/or noticeable back in boy mode)

• Shaving your entire body
• Growing out hair / wearing a wig
• Breast forms
• Lingerie gloves
• Dress
• Yoga pants/leggings (without other pants on top)
• Skirt
• Shorts
• Majority of tops (without hoodie or coat)
• Choker
• Perfume
• Painted nails (difficult to remove all residue and can stain)
• Any shoe with a heel and/or clearly feminine style
• Colored lip stick/majority of makeup
• Fake nails
• Purse
• Full body harness
• Rings on hands
• Bracelet
• Real piercings (anywhere)
• Fake earrings
• Nipple clamps
• Shapewear with pads
• Real tattoo
• Fake Nose Ring
• Babydoll / Chemise (these typically stretch below the waist and would need to transition your shirt and pants)

Final pro tip, this may vary depending on your personal body - but I find it can take up to 2 hours for strap lines, like from bras on your skin to dissipate. Give yourself enough time for these marks to go away before you might be showing skin.

I am pretty new to this, so I would appreciate some advice. The first few items were easy and obvious.

Panties ✅ Panty hose ✅ High heels ✅

After those, I dont know what to get anymore and I am kind of overwhelmed by all the options. What would be the next key items to buy to continue my journey?

Can anyone prepare me mentally for a sissygasm please,,, I am desperate.. Please someone melt my mind.

I want to know should i use body trimmer or razor which will be a better option for cleaning the body hair.

On day 6/10 self locked and getting very frustrated today 😩 I have a nice 8in bbc dildo, some plugs, nipple suckers, and obviously my little cage. I need some ideas and instructions for what to do to myself tonight, send tasks and degrading routines for me to follow your commands!

Hello there) I just wanted to ask. When I do anal with myself or with my girl (in chastity of course), I was squirted (and I use poppers). But I think it was urina, probably I know it was urina. In sissygasm videos girls in chastity really cum with sperm from doing anal. So the question is, it should be urina or semen? And if it's should be semen, how do I goal it? Hope for your advices or tips

P.S.: Not so regular sessions of mine (maybe 3-4 times for month), but imho it's not so important. And sorry for bad English, I don't use it often)

Hey everyone,

I've been going to the gym for a while now, but I'm not sure which equipment and exercises I should focus on. I'm a male between 25 and 35 years old, weighing between 110-120 kg, and my height is between 180-185 cm. My goal is to slim down to 70-85 kg to make it easier for me to buy female clothes.

Here's what I'm aiming for:

Medium-thick thighs and glutes
Visible breast development
A moderately small waist

I usually spend only one hour at the gym. I’ve included Imgur links with all the machines available at my gym:

https://imgur.com/a/bvJT4iC

https://imgur.com/a/images-of-machines-gym-part-2-mxffh6R

Could anyone suggest:

Which machines to use?
How many sets and reps for each machine?
How long I should use each machine?
Which exercises to do?
How many sets and reps for each exercise?
How long each exercise session should be?

Additionally, could I maybe get video instructions on how to use the machines and perform the exercises?

Any advice on structuring my workouts to achieve these goals would be greatly appreciated. Thanks in advance!

Edit note: The Imgur links were causing some issues, which is why I had to edit the post multiple times. I apologize for any inconvenience caused.

I'm really new into sissification, but being feminized is an old, returning fantasy for me.

The problem is, I don't know how to get the true sissy mentality. Most of the time I do a small purging when the post-nut clarity hits, which prevents me from really getting to explore this side of myself.

I kinda want to become immune to purging to be able to become more sissified.

What can you suggest?

23M

Hi there I'm a sissy very much in the closet....still experimenting (alone). I'll have a all week for myself alone starting the 22. I'll be open to tasks and challenges if want me to do. Guide me through my sexuality to expand my sissyness. Optimally I would love to have someone that could manage my day hour to hour with tasks to improve my slutiness. I won't share irl data ...but aside from that....Wana try me? Kiss kiss Mat hai

I love being my sissy self but whenever I end up coming whether it be from edging or ruined orgasms I immediately get disgusted with my self and usually end up purging. Any other tips or tricks I can use to stay in my sissy mood

i just want a girls night out talking about cages and makeup and guyssssss. a place we can whore out together and train and encourage each other to be better and better girly sluts. its my dream. i have like no girl friends to talk about this stuff with and i need some. so why not a server full of em? we can all be slutty together! those identifying as guys can come too but we'll have some girl only channels <3
if there is interest i will make the server.

Quick background: Bisexual dude who feminized myself in the context of the two most recent relationships with men I've had. The second of which ended about a month ago, and I've casually been seeing a woman lately. We have not really talked about sexuality, in my mind I think I could come across as just an androgynous looking guy.

And I may have shattered that illusion by accident tonight.

She had come over to watch a show/cuddle + spend the night. As we were on my couch and the show ended I was trying to show her something online, mis-typed and my browser went to a hentai site. (Not the most embarrassing part of the night)

I blushed, she laughed, and then asked me if this was the kind of thing I looked at when she wasn't around. I admitted to occasionally browsing it, and she asked to see what kind I like. I pulled up a fairly inoffensive/discreet one and we started scrolling through it.

As we're reading she starts rubbing me over my shorts and once I'm hard pulls them down and starts giving me a handjob. I kissed her a bit then she pulled away and told me to keep reading. I warned her I was getting close, she said 'good' and I came kind of fast. (Still not the embarrassing part)

I had been kinda laying down and pulled up my shirt+hoodie and finished on my stomach and avoided getting any on my clothes. But, in the process of cleaning up, some of my cum dripped on to the bottom of my hoodie. In a moment of absent-mindedness and what I'm considering a "Sissy Instinct" I pulled my hoodie up to my mouth and was about to lick the cum off of it.

It was like an inch away from my mouth when her and I made eye contact, and I just awkwardly lowered my hand and cleaned it up with a tissue. My face is practically blazing scarlet when she asks, "Were you about to?... Nevermind." We sat there in like dead quiet until she got up to the bathroom to wash her face.

She's still staying over but the vibes were horrendous after that. I have no idea how to proceed/what if anything to say.

amateur sissy, wants to meet other sissy sisters,I want to be feminized and transformed into a good sissy, I WILL NOT PAY

Hiii ladies:) It’s been a while since I’ve had a good girly routine and want to find a good inexpensive facial cleanser at Walmart. Do y’all have any recommendations?

I am a boy and I would like you to help me feminize myself

I had wonderful success with some affordable silicone breasts from Shein. Champagne / American skin tone is a near perfect match for me.

I wanted some hip enhancement too and took a risk with lower cost. Unfortunately not as satisfied as with the breasts. Poor skin color match and much more butt than hip enhancement. Roanyer do strong hips but they are 4-5x the price. Any recommendations at the lower end and still silicone?

Hi all, I'm sure the best option is to go to the store to try things on but that's not an option at the moment.

How would I go about finding my women's size for things like high heels, pants, skirts, tops, and dresses?

So far I've found stuff like this:

What size of women’s high heels do I need if I wear a size 10 men’s shoe?

How do you convert men’s shoe size to womens?

MEN’S VS. WOMEN’S SHOE SIZE: HOW DOES IT ALL TRANSLATE?

But any advice or tips will do. Thanks.

Hi! I am here to ask for some advice from y'all. This won't be long, so any help is appreciated.

I have observed that I'm fairly submissive in my daily interactions with people and deep down I like this feeling a lot. Recently, I have begun to notice that at times in a social event, whenever I encounter a girl around my age or elder to me, in my head I start to imagine how I would look while serving them or how I am meant to pleasure them by obeying/supporting (for ex: them commanding to kneel or to worship their feet or them getting fucked while holding my hand or even a normal scolding). The same thing happens to me when I look at hung men (but only while watching porn).

The problem is that at this point of my life, I cannot explore this interest of mine very seriously (i.e. physically with someone) but what I want to do currently is to fixate this feeling internally so much that I can manifest it when it will be suitable for me after 7 months or so. I need your help in crafting different routes/rules I can follow while interacting socially with say a girl and I seriously WANT myself to have a strong feeling of serving someone superior without any hesitation whenever I encounter them. I request ideas that can help me delve deeper into this feeling (for ex, in porn I follow that I will look ONLY at the girl's eyes or feet) but this time more in real life.

PS: I would request that please refrain from commenting that this is not a healthy habit or a wrong state of mind or wait for 7 months (I have patiently waited a looong time). Sometimes you very consciously decide to follow a path, which is what I am trying to do here.

Ashley Adamson has an excellent video about Denial

https://youtu.be/UDJ4vmiT3Eo?si=E7dCheF_roYoQExC

So I recently started shaving my complete body even though I haven't all my life.

Legs and belly seem to be fine, however I have severe problems in my genital / ass area and have shaving bumps and spots all over. (See my last post)

Is there any way I can avoid that? I've tried shaving with the grain, moisturising and the likes but I'm unsure. Is there anybody that could give me some pointers in the right direction?

Thank you so much.

New to crossdressing I bought some 7" stiletto heels (2" platform under the toes). I had never walked in heels but with a little practice and calf strength exercises the walk is becoming better.

On hard floors I am making progress but the bedroom has a deep pile carpet. I can walk but it's hardly elegant.

Is it possible to walk in stilettos on carpet? Will it ruin the carpet? Walking on toes is easier but it looks bad. Please help!

So I want to finally get a full Brazilian laser treatment. So tired of shaving and I’ll be smooth all the time. Forever 🥰

What other area should I consider? I was thinking upper legs as the back of legs is prone to razor bumps. Any suggestions or any feedback from someone who’s done laser hair removal?

When I discovered the whole Sissy kink it bursted into my life like a tornado. By now it's probably my 2nd biggest fetish and I really enjoy masturbating to sissy content (as of now I myself am not a sissy and I don't intend to become one).

Right now I'm kind of reflecting on my whole sexual life and also think about why I'm into what I like. Not that it would matter but I'd just like to know for myself. Therefore I was thinking a lot about this kink and would love to know: what do you think is it that turns "straight men" into sissies?

For a few years now I embraced the fact that I'm not only into cis women, but also into trans women. I had a lot of fun exploring this side of my sexuality. With discovering femboys and sissies it got a bit complicated though. Now I identify as gynesexual, but I still wonder: how could it come this far?

On this sub and the entirety of reddit, I read so many posts about how "100% straight men with zero interest in men" got turned into "cock loving sissies who only desire men now".

I think for me, I'm pretty sure that I just had it always in me. I like dicks and I had always a fascination for femininity. But what about those other men? What about you? Do you think you also just always had this side in you and you just had to open the door? Or do you think this kink and it's content is simply so powerful that it can turn you 180?

Or do you think it's something entirely different? Is it a way of living out other kinks (like submission, humiliation, etc) or expressing oneself's inner femininity? But then, why does it continue in your everyday life aside from your sexual life? For some of you it's a whole lifestyle (at least at home). Maybe you just wanted something new and refreshing in your life. I don't know, but if it makes you happy I think it's great

And did it change the sexuality you identify yourself with? Do you think you were straight and now you're bi, maybe even gay? Do you think the sissy content actively changed your sexuality (if that is even possible? i genuinely don't know) or do you think that has always been you?

Maybe there are no real answers to those questions, there certainly isn't just one. But I'd love to hear it from you :)

Hey everyone,

I have always been curious about something - how does using a strap-on compare to having sex with a real penis?

I've wondered if it can truly replicate the feeling of a real cock. I know there are various types of strap-ons, some with more realistic textures and others that are more firm and sturdy. But I wanted to hear from those who have experienced both - what are your thoughts?

If yes, what triggers it? How long before you come back to being a girl?

I noticed this is wayy to common.

I achieved the ability to "Ejaculate and orgasm" from anal only, 2 years ago. However, that orgasm and even the stimulation feels like a penile stimulation and a penile ejaculation and orgasm.

Whenever i finish ( anal only ), i have the same refractory period and it would also give me a compelling urge to purge, not to mention i can't go another round, EXACTLY like a penile orgasm.

I keep hearing about people being able to achieve the dry multiple shaking orgasms via anal only, and that it's exactly like females. But i seem to can't reach it.

I have been searching for posts talking about this in detail, even asked several people, but nobody seems to talk about it other than the ejaculating anal orgasm.

How do i reach this multiple long period full body orgasm ? How do i also keep going multiple times without refractory period or PNC?

Heyyyyy girlies!! I just needed to share my excitement! Im extremely new to the sissy world, but I'm so excited to explore my feminine side :3 I think it's something I'm going to do in private for a bit, until I get the courage to go all out, but baby steps, right? But Im shaved (everywhere ;)), I have a playlist of songs put together, and I'm so excited to put makeup on while I wear them. I even got a cute skirt and sweater... And maybe some cute leggings...

I hope you know that you're all amazing and beautiful, and just lurking in this sub has helped get me started ❤️❤️❤️ if anyone wants to chat, hmu! I'm excited to connect with this community and get to know some of you 😜