Hi Everyone,

So I am starting out as a new sissy. I want to document and post some of my journey as I go along from being a pretty masc and dirty looking poi to a pretty sissy.

What are some of the things I should do early on that would really help me becoming a sissy?
What was best for you, what do you regret? how do I make the most of getting started.

Literally just wondering if I can post here yet.

I have played with men and it just feels like it’s tugging to hard when they play with me, is there any product I can do or massage I can do that will make my foreskin longer?

Hey gurls! I (23 sissy) recently told my gf about my sissy side (do didn't call it that yet but described everything it involves) and my gf wants to be supportive cause she saw how excited it made me to fantasise about. She wants to have a "girl's night" with me but she's not really experienced with sissies or with being dominant in general. Would you girl have any tips or ideas of how we can make our girl's night extra exciting? It doesn't all have to be sexual, it can just be stuff that really connects a sissy to her femininity or that shows her the power she has over me. Personally I thought of letting her paint my nails and do my make-up and watching legally blonde or mean girls together but I haven't gotten further in my head so far.

What’s the best substance to use for solo play?

Once never, now considering it as I experience more sissy-gasms and multiples

I was scared to during locktober but I was just feeling really comfy in it and didn't want to take it off so I put on a cute bra and panties and left it on...then again the next day....and again the day after that.. 🙈

I walk around a lot at work so I was worried it might get uncomfortable but it's actually super comfy and I barley feel it. Now there is no reason to unlock.

I am new to this , and would love to connect with other sissies to discuss outfits and whole of other stuff, if anyone interested?

Hey all. My wife and I have been playing with some fun / sexy ideas for the coming year and one thing we did was make a calendar of cuckolding rules for each month of the year. I’d love to also do this for sissification. For example: January: panties every day Etc. anybody have any ideas?

Looking for advice on how to use a thrusting dildo with suction cup

So I am asking to see if there are groups or subreddits where sissies can talk or ask for advice making content?

Today I went shopping for the first time dressed up. It was extremely nerve racking. It was so nice tho being able to just shop in the store like a normal girl instead of amazon. The cashier was quite rude but other than that it was fine. Would love to have a fellow sissy friend to shop with.

Horny wannabe sissy here. Horny af and super wet. Will be your personal pornstar. Dm me doms😩😳

I just signed up for private ballet lessons at a studio and I am so excited! This will be the most sissy thing I have ever done and I can't wait to wear a leotard and tights and get taught how to dance one on one. Regarding the attire, they said because it's private lessons, I can wear whatever I'm comfortable with and that I could invest in "traditional ballet attire".

My question is, what should I wear and if you were me, what would YOU wear?

I'm so excited!

I bought a buttplug set online and decided tonight was perfect to try it out. I had to coax it in with a lot of lube (it was pretty big to start out) but once it went in it felt SOOO good. The cold glass felt amazing against my walls as it warmed up. I can't wait to do this more often!!! I also have a g-spot vibrator that i've been waiting to try out, that may be in the books soon

Hey beautiful ladies I’m looking into cages and I’m trying to think what’s the right size for me to start with. And if there’s any decent priced ones I went to my local sex store and they were like 65 for the cheapest and I was thinking that was a bit overpriced.

Hey! I’m looking for a cage that is comfortable enough to wear at work and not bulge too much. If anyone has a recommendation please tell me! Thanks :)

I love hitting the local adult book store for the gloryholes, and was there after work, not even crossdressed just horny in my chastity cage, and spent fifteen minutes working this thick cock that barely fit through the hole. My mouth was getting tired so I started stroking him off, turned and bent over, and slowly backed my pussy up onto him. He didn't pull back so I pushed all the way back to the hole, and he started slamming into me over and over, took him barely two minutes to cum all up inside me and the last couple of shots on my hole. During this, another man had snuck into my booth and just watched me get railed bareback by a stranger, moaning and bucking against this thick cock, my pink sissy pussy chastity cage bouncing. I did drop to my knees and suck him off after, feeling the wetness between my legs as cum slowly drooled out of me.

I felt it the whole way home in slow rush hour interstate traffic.

Trying to pass a little time, wondering if anyone wants to chat!

I've loved the feelings of being a sissy slut for a long time, but the one thing that's bothered me the most is the fact my ass is really big, but the sides look kinda square.

Someone said a diet, but nothing about what type of diet or something similar. Does anyone here know what helps?

I'm 18, I'm getting too far into this, every time i try to go back i can't and i look too feminine for a "man" and I've been feeling myself grow attracted to men and i haven't had the interest to touch myself while erect.

Heyyy ladiess, I’m a pretty fresh sissy here to be honest. Not that feminine at the moments but I’ve been watching hypno and doing sissy stuff for a while nowww like 6-7 month sooo I think it’s time I get to becoming a better sissy and find a daddy you knowww

Been using my dildo for a while and I really want to try and get my first HFO. Any advice? I know I need to practice a lot and stuff but are there any other tips and tricks to try and achieve it?

So I made a bet last week on the Tyson fight and I knew Tyson would win and... Nope so now to hold up my end of the bet. I have to get my belly button peirced, which is way better then what my buddy was gonna have to do, get a smallish tattoo of my choosing so lucky I didn't get that. But I've got my ears pierced and now gauged but I've only had those. Ive wanted to do this but I feel like it's only gonna cause a awkward situation later on. Around family and swimming or a new straight relationship ect... Idk what to do

Im about 2 inches soft but 6 inches hard and the current cage i have my foreskin makes it difficult to wear long term since it pokes out the front making it hard to use the restroom or stay hygienic. Hoping someone else has advice! Thank you :)

Hello lovelies

I am building up my Pleasers collection but I want higher shoes/boots. Yes, that means higher than 7-8” which I can walk and dance in no problem. I’m not having much luck except for some sketch looking stuff on EBay and a few Chinese websites.

Anybody know of a place where I could get higher, quality platform heels? I think 9”-10” would be the limit for safe walking (at least on a Flamingo-style ankle boot). Of course the other problem is that I need a women’s 14 (in Pleaser sizing).

Thank you dolls 💕

Fill my dms with dick pics or anything you want and i will answer all/ do anything you say 😁

Please please please

Hey everyone!!! So pursuing Grindr I came across this amazing BBC. When he first sent a dick pic I legit thought it was his forearm for a second. He’s 10 inches and THICK. Now wanting to be the good sissy I am obviously I want to choke on that majestic dick and let him tear apart my hole. With all that said he will beat my biggest by at least like 4 inches and who knows in girth. My typical prep is enema and toying with myself any tips or recommendations are appreciated!

I started HRT a month ago (Spironolactone and estradiol) and omfg it’s like night and day.

First thing to change. Mental benefits. The best way I can put it is that looking back, it was like my emotions were playing through an old black and white tube TV. Now it’s a 30 inch LCD 8k display! It’s all so much more vibrant!

Next, my skin!

My skin is soooo fucking soft omfg it feels like velvet, especially when I’m freshly shaved. It makes me feel really small and delicate as I run my hands over my smooth soft body. Oh, and less oily skin, I need a LOT of moisturizer.

Sensations.

Everything just feels kinda different?

I’m still stealth (for safety reasons) and omg guys clothes are so scratchy! I wear woman’s clothes at home or in safe spaces and it’s infinitely softer! Everything just feels so much more sensitive I guess. Oh, also, pain feels different. In a way I can describe though. It’s like saying “Huh, the color blue looks more blue than before”.

And Oh. my. God. Pleasure just feels so much more intense. I used to be very quiet when masturbating, but I genuinely cannot hold my moans anymore. Everything is just so much more sensitive. Downside to this though, my feet get cold super easily.

And lastly, boobs.

There isn’t really much to say, they have just barely started to grow but my nipples are so sensitive that I need to stop myself from playing with them pretty much constantly. Oh, and my doctor recommended I give myself a type of breast massage every day to help prevent too much soreness and it’s pretty much heaven. As they grow more sensitive I honestly don’t know if I could handle doing it anymore it is so mind meltingly good.

Now keep in mind, I’m not just a sissy, I am trans. Please don’t take hormones if you aren’t trans and/or want to be some level of androgynous as many changes are irreversible and others only benefit you if you are trans as otherwise, it could give you huge amounts of dysphoria.

Also, just because you are a sissy and this is a kink doesn’t mean you aren’t trans. Sex and kink are often a gateway or a reflection to deeper thoughts.

I felt like i had to share this, as it felt like a dream come to life😍😇

So, when i got home from work, i started going through grindr because ive been horny all day. So i started prepping myself in case i found a willing daddy, and after 30min or so a black guy popped up. He was american and here on a business trip, and i thought "perfect!" And we agreed on the basics.

I finish up prepping, put on cute little bustier, black stockings, matching thong a cute short dress and put on some boyclothes over and stuffed my wig carefully in my bag. I started making my way to his hotel, which took a while as i dont live near the city centre where he stayed.

When i got to the hotel i made my way to the elevator, got up to his floor, and found a place to transform into my sissy alter ego. I checked my wig and the little makeup i had, and walked to his door and knocked. It felt like i had a thousand butterflies in my stomach when he opened up and let me in.

What met me was a tall, muscular man in a suit, and i felt so girly standing there looking up at him slightly. I wore some kinda tall heels and im fairly tall, and it made me really happy to be short and smaller than him. He had requested to do bareback if i was recently tested too, which i actually had after my last relationship (gf cheated). We showed each other our test results (super sexy, i know😂), and he spanked me and called me a good girl.

We started kissing a little bit, and he grabbed a good handful of my ass while doing it. After a little bit, he told me to pull back the curtains (which scared me a little at first) and place my hands on the window. He lightly kicked on my ankles to make me spread my legs, grabbed my hips, pulled them towards him and told me to arch my back. Then he hiked up my dress and started spanking my cheeks to get them red, while also giving me a couple of wedgies before pulling down my panties. he checked my cage (metal nub cage that looks like half a sphere), played with it a little while messaging my pussy.

He then told me to get on my knees with my back against the floor to ceiling window, and made me watch him take his shirt off. He then walked over to me, got his crotch right up against my face, and i could see it was straining to get out, and he smiled and said: this is my favorite part. I unbuckled and pulled down his pants, and his cock hit me in the face. It was a gorgeous, thick, weiny 8" with a slightly smaller head, and he started laughing and told me i looked like the girls in the pornos when they did the same, and i giggled back.

I started sucking and playing with it, and after a while when it was nice and wet, he grabbed my head to throat fuck me. To my amazement, i actually managed to take him all the way a couple of times. He told me to get up and face the wall again, and i could hear he started lubing himself up. I felt him line up with my hole and started to push himself into me gently, and picked up the pace while i moaned. Then he pulled me towards him and pinned my arms behind my back and pushed me against the cold window and told me to watch the people walking past below while he fucked me. After a little while my legs started shaking, and he pulled out, lifted me and threw me on the bed. I felt like i was in a sissy dream as ive fantasized about that for a long time.

He pulled me to the edge and started going at it again, and he now he was hitting my spot with every thrust. Not long after my legs were shaking again while being pushed back. I felt a squirt build up, and after a little bit he picked up the pace and slammed into me every time, i squirted all over myself and i wimpered in extacy. He slowed down for a little while before he repeated what he did, and i squirted a second time, but this time he pushed all the way inside me and he moaned while i felt him trobbing his cum inside me, before he collapsed on top of me.

After a little bit we got up and dressed, i said goodbye and thanks when he walked into the bathroom, and i put my boyclothes back on and left.

Im writing this on the metro train back home, and feel his cum slowly leaking out, and feeling pretty happy about it 😇

Hope you enjoyed reading my little friday evening adventure❤️