/r/Sissy
A safe place for sissies and those curious about sissy culture to talk about all things sissy! Ask questions or discuss about anything sissy related :)
18+ Only
r/sissy is a safe place for sissies and those curious about sissy culture to talk about all things sissy!
Ask questions or discuss about anything sissy related :)
Please read the rules before posting!
Rules:
1.18+ only
2.Be kind
We don't allow any insults, hate speech, homo- and transphobia or other signs of intolerance. In short: Just be a decent human being.
Also, no blackmail or lost bets or anything that has any potential to be without consent. General discussions about fantasies that touch such topics are okay, as long as it does not get too graphic and detailed. The mods will have the final ruling over what is okay and what is not.
3.No selling, begging, spam, "upvote if" posts/comments of any kind.
4.No advertising unless mod approved. Read description for how to get approved.
Unless you get an advertisement approved, no advertising is allowed, including directing users to your profile
If you have something that you think is relevant to the sissy community (meaning support, help getting started, resources, etc.) message the mods before posting to request a mod approved advertisement. After reviewing the mods will approve or deny your request. If approved, make your post and the mods will flair it with a special flair indicating it has been approved.
5.Evading Automod or existing bans will lead to a permanent ban
Trying to actively circumvent Automod by for example trying to obscure specific words or using any other action to do so will be punished.
Same goes for trying to evade a ban by using a different or new Reddit account.
6.No personal information of any kind
7.Make your post under the appropriate Flair. Flair guidelines link in this rule's description.
Flairs are pretty straight forward, if you are unsure about what they mean, check out our post flair guidelines wiki page
If you make your post under the wrong flair, it will be removed.
8.If you have a new account use the "New Sissy" Flair. There are limitations, see description
Your account can be just created, but we still require at least 2 comment karma and a verified email to post under this flair
We do not allow Personals or Task/DM Requests under the "New Sissy" flair.
This flair is not for gaining karma, this flair is for new sissies to ask questions to the sissy community
9.Personals of any kind must be flaired with "Sissy Personals" or they will be removed.
Sissy personals both directly and indirectly must be flaired properly under the "Sissy Personals" flair. Its at the mods' discretion whether it requires the flair or not.
You may ask for advice in DMs in the Need Help / Advice flair, but nothing more than that
Also, please keep in mind rules 6, 10 and 15!
10.We do not allow non-sissies to make personals.
11.If you add a user flair, please follow the guidelines linked in this rule's description
12.All interactions have to be in English
13.No photos, videos or other media
14.No off-topic discussions
15.Post requirements/restrictions
We do have the following minimum requirements to post or comment:
Comments: Account age of at least 2 days
Posts using the New Sissy flair: At least 2 comment karma and a verified mail address linked to your profile
Posts using any other flair: Account age of at least 10 days and at least 2 comment karma
We also only allow one Sissy Personals post every 3 days per user. Any failed attempt to post a personal request (e.g. when using the wrong flair) will also count here.
/r/Sissy
Recently went all the way with another guy (we're both bi) and I felt turned off by the overall experience. I didn't feel hot or sexy while we did it and there was a nagging feeling that I wasn't really enjoying this (despite having my ass penetrated which I love). I've went all the way with some trans before and I really enjoyed it especially getting penetrated by such a beauty.
I've been thinking about it and does it still make me a sissy if I only like really love everything to do with femininity and cocks but get turned off by men in general?
I don't get hard for straight porn i only look for dicks in that and in position of that female getting fucked. Is this achievement or what?
Been feeling like doing ball stuff all day 🍒💥👋
So, like the title says, I really want to ask like a sissy slut, and such huge cock. But I have a girlfriend who i really love and appreciate, and I'm the dom in our relationship and I really enjoy it. But I also really want to be a sub for someone, But opening the relationship is scary, I don't know what to do. She's also my first girlfriend ever, and I've only ever had sex with her. But I've played with my ass with dildos and she knows, but I've never done it in front of her. What should I do?
Hi girls!!! So I've finally decided to do two things. Number one buy me a full slutty outfit with lingerie. And secondly I'm taking the leap from riding and playing to full on sex machine! I'm buying both at the same but can't decide what outfit to go with. I'm getting a pink micro bikini set with stockings and a red one piece baby doll as the lingerie but can't decide one whether to get a cheerleader outfit, go gothic style with a skirt, a slutty schoolgirl, or just stick with the lingerie which will be adorned with a "sissy slut" collar. Any help would be greatly appreciated!
Anyone awake I’m trying to pull an all nighter playing with my bussy and want to see if anyone wants to chat for a bit.
I’ve been talking online with a guy and he’s built me some small level of trust… I’d kind of like to video chat with him but I don’t want to be dumb about it… is there one where he can’t screen record and won’t know my true phone number, email, etc? I’m in a hotel room for a few days so finally have a chance to download and use something I otherwise wouldn’t….
I just wanted to ask your opinion… well for 4 years I’m watching only sissy porn and hypno but I’m still virgin at 21 and still in denial and idk if I really want to become a sissy and get fucked or suck cock.Well I imagine it every day tho… Tbh I’m really lusting and craving cock so so much but something holds me back. I also like girls and irl I’m like the ‘strong guy’. Now I’m wearing chastity so much and panties and I really like wearing them. Any advice would be really helpful!!
Got a little too horny at work today and had to run to the bathroom to take care of it. I locked myself in a stall and quickly pulled down my pants and the pair of panties I was wearing and shoved my fingers in me. I rocked my hips back and forth on them while scrolling through Reddit in my other hand. I got excited every time someone else would come in wondering if they caught a glimpse or saw my panties on the floor. After a few minutes I couldn’t take it anymore and had to get back. I shoved as many fingers in as I could and fucked my bussy till I came all over the stall.
Hello gurls! I'm hoping to hear from some of you on your favorite brands to moisturize your bodies with. I'm running low on mine and looking to try something new! 🥰
Today was an amazing session. Rode the crap out of my dildo. Put it on the wall and it made me feel like a real girl getting fucked. I started to fling pre cum everywhere but I just couldn’t finish from it. Any tips on how to just let loose and cum everywhere? Thanks
Hi there I’m now 20 been with my girlfriend now for 1.5 years she showed me how to be a sissy and has bought me many toys it was all good as I really wanted it to work as she is so hot!
However she ended up resenting my locked up cock and has since cheated on me so I tried to break up with her however I needed to be unlocked.
She came to unlock it however we ended up in a play session with her showing me all the photos and videos she had taken of us and her making me into a sissy I feel trapped as she is now got the keys and still pretty much has utter control over me due to her having the keys and the blackmail on her phone.
I must say as well her bf knows about me and feels exactly sorry but plays along with it what do I do help!
Just got fucked in front of my girl friend and her best friend friend that is a girl by their gay friend. It was the sexiest thing I ever experienced. I never felt like more of a cock slut before
Hi girls,
TL;DR: I feel very bad, empty and worthless after an intense online playsession. Any experiences? What is it and how can it be less extreme? Thx! 🙏
I just had the most intense playsession I ever had. I love being a degraded sissy who is used and punished, love pain and being told what to do. I love being handled mean and hard. But I think I went to far tonight.
I have an online daddy I play with through snapchat. We played tonight but I was pushed to the limits: made ruined cummies twice after days of edging, intense pain play, etc. After ruin 1 I was still very horny and asked daddy for more. After the second ruin I was empty and broken, but he kept on telling me to suck his cock (dildo) I came on, keep on humiliating myself and doing nipple torture. I felt myself breaking but kept being a good girl.
But now, I feel worthless and empty. It was all I asked for, and I loved it in the moment, but feel like soooo bad rn. I have no idea how to help it. This isn’t daddy’s fault at all, it’s nobody’s.
I was wondering: are there other girls who have this? What is it? And have you found a way to cope with it or have it less extreme? Thank you so much, I really need your advice.
Hey sissies, I have a porn related question here. I absolutely love the humiliatrix videos but unfortunately that website hasn’t uploaded anything in a few years. Does anyone have any similar websites they enjoy?
As the title says, finally on my business trip and finally have a few days in my hotel room for sissy time.
Last time was when I made this account… and then found out none of the sissy subs would let me post cuz it was too new!!
So this time I get to stay logged in the whole time I’m here and post or comment whenever I want instead of signing out every 5 min to make sure I stay incognito
Amazon lockers are a blessing and a curse. I tell you there is always something. First time it worked perfectly. Second time I got infinitely locked out of my account AFTER I ordered, so I didn’t get my order or my refund. This time I avoided prior mistakes, and it was still a pain to place the order while trying to be anonymous. Then they split my single order into 4 separate orders even though they were together in the cart supposedly to be delivered on the same day to the same locker. Almost missed my chance to pick up one, picked up 2 more, but the biggest order has yet to be delivered. It was a day late on its own and then the power went out at the locker location and it was closed and they couldn’t deliver. Still crossing my fingers I get it later tonight.
Even so I have my backup stuff and a small amount of what I ordered.
So, first makeup try tonight and if I’m lucky first time wearing a dress too. I’m mostly shaved and gonna have a good few days, one way or another :)
I just want to say thanks to all the girls that frequent this sub and help each other have someone to share with. Love you all
I don't remember which subreddit I saw it, but there was a post for like a "comprehensive" guide to being a sissy/feminization.
Specifically it included directions on how to create a new youtube account and what to search/watch to configure the algorithm for girl mode e.g. fashion and make-up vids. Does anyone remember seeing something like this that they could share with me?
i want to meet up with someone from reddit and do the sexy things we talked about over chat. when i get there im wearing… no panties, a fresh new pair of sheer black pantyhose layered under another pair of opaque ripped pantyhose, leg warmers, boots, a black mini skirt, underneath my oversized chunky brown sweater (that almost covers my skirt) i have a top i made out of gold pantyhose, and some jewelry. my nails are long and freshly painted, my hair is pinned behind my ears, my makeup is done and i have a big butt-plug in my tight virgin hole. i walk up to their door and knock. my heart is beating so fast i think im going to have a heart attack. they answer the door wearing only their underwear and a tight tank to. i scan their gorgeous body and when my eyes meet the print of their massive cock my little dick starts to stiffen “h-hi :)” i barely murmur out. they move closer to me, grab the back of my neck and pull my head to thiers and give me a kiss as their other hand reaches around and grabs a handful of my little butt. i almost melt into goo right there. my mind is corrupted i’m all theirs now. they pull away and say “wanna come to my bedroom” “y-yes of course” i say with so much excitement. they grab my hand and lead me through their house to their bedroom. once we are in they close the door behind them, throw my onto the bed, and they get fully naked the sun marinating in their skin. they come closer to me and start kissing me as they take my sweater off. they move down my body kissing and licking every inch of me. they call me their good little sexy boy and at this point i am rock hard and leaking. they pull off my skirt and kiss my throbbing, twitching, leaky penis over my soft, velvety pantyhose. they massage my thighs and move up to my torso then around to my back and then down to my ass and they keep repeating that motion while they kiss and lick my penis and balls. i’m moaning and breathing so heavy, my mind is fuzz and all i know is “i want to feel this feeling forever-“ o- omg did i say that out loud i think “oh i can make you feel this forever baby don’t worry” i’m embarrassed, turned on and maybe a little ashamed that i said that but all those feeling fade away as they rip open both my pantyhose revealing my hard glistening cock and balls they grab my dick with one hand and start licking and sucking my balls. they grab my butt plug with their other hand and call me a naughty little slut. they start teasing my hole gently pulling on the butt plug then releasing, pulling in it then releasing, over and over. they move their tongue up the shaft of my dick and start twirling their dripping wet tongue around the tip of my penis. i’m in heaven. they wrap their lips around they head of my cock and start sucking me off. they have my balls in one hand their other on my thigh and their mouth on my dick. this is everything i dreamed of. they do this for an hour, edging me the whole time. eventually ounce they made an absolute slobbery mess of my groin they take my dick out of their mouth and slowly pull my butt plug out. they pull me to the edge of the bed and use all their spit to massage my tight little hole. they stand up and say are you ready my good little whore. “mm yes! i’m ready for you” they rub the tip of their hard dick against my smooth wet hole and i’m moaning the whole time. they slowly start to push it in and i feel myself start to give into the feelings of lust all i want is to feel this forever. they start to thrust back and forth sliding their dick in and out of my tight, now non-virgin hole. “god you’re so fucking tight baby” “you’re gonna be a perfect little sex slave for me”… c-can they read my mind?! how do they know what i’m thinking exactly?! they start fucking me faster and faster deeper and deeper. just when i think their balls deep, i feel more cock slide into my hole. they rub their hands up and down my legs. they move towards my feet and take off my boots and leg warmers. they kiss my nylon feet suck my toes while one hand massages that foot and the other one is jerking my dick. they rip a hole in my tights at the toes so they can suck my raw toes. then they turn my over on my belly spread open my asshole spit in it and ram their entire massive hard cocking inside me. i’m screaming and moaning in pain but also ecstasy. they are pounding my little pussy and pinning me down with both hand. i feel so helpless. i feel like a mindless flashlight and i love it. i start cumming and cumming and cumming i’ve never came this much in my whole life, i did it even think a human could cum this much, they call me a dirty whore and stop fucking my they grab my hair and pull my face towards my puddle of cum on the bed and make me lick it up and suck it out of the bedsheets. they tell me to spit it on their hand to use it as lube and i do it. then they bend my over the bed and rub my own cum onto and into my asshole and start to vigorously finger me then they stick their cock back inside and drill me. they tell me to tell them when i’m about to cum. this happens 5 times each time is like cum just materializes out of nowhere. there is no way my balls can make this much semen. each time i’m told to come in different places. the first time was on the bedsheets. then second time we are in missionary and i’m told to cum on my tummy then scoop it up and eat it. the third time we are vertical and i cum on my own face and mouth. the fourth time i cum straight into a bowl and drink it up like a cat. and the filth and final time i cum into their mouth and they spit it into my mouth. after the fifth time i’m laying in their bed exhausted while they fuck my numb boy hole and when they are about to cum i muster up the energy to turn myself around and suck them off to completion, i deep throat their huge cock and they cum directly down my throat. after i swallow that load i pass out from exhaustion. laid out used and abused, sweaty and leaking… but when i wake up-
thank you all for reading! i’ve decided to make this a multi part series and eventually i’m going to draw it into a comic so if you enjoy definitely let me know! pt2 coming soon… after i finish gooning cause holy shit i’m so turned on after writing this.
Just curious how many of you encountered this, and how it happened? The more details the better😅
Help I am curious
Hi everyone,
I am bi and very turned on by sissy captions for a few years already. In 2 weeks I will have the opportunity to live alone for 2 weeks which is the first time in years. I am thinking about trying to wear femboy or sissy clothing in order to find out if I like it and it suits me. I find it difficult however to know where to start. There are so many things I never thought about in my whole life and now they would become relevant.
I guess these are just some starting questions and there will be loads more once I take the first step into the lifestyle..
So please if you could help me that would be much appreciated 🤗
How do I hint at my wife I want her to try anal with me? I’m struggling with the courage to ask.
Hello, is it normal in the following day of a good long fuck session with my toy to have back pain, leg pain?
Looking for Male daddy to talk to and have fun with I will be in miami for a trip in around 6 days and im looking for fun there. Dm me for info and lets have some fun Looking for hook up in miami Must be 16+ and should be black,i prefer black but yoy can be white😊 P.S. You can also be sissy or any kind, girls are also welcome💕
Im still trembling. I have been trying for years and finally all the stars aligned. I listened to advices i found here. Focus on the pleasure building, go slowly without pain and use a lot of lube. I was caged watching hypno and stumble upon the perfect hfo at the perfect time and i exploded when she told me to cum. Giant spurts over and over... unreal. I came again 5 min later and i was trembling after the last orgasm. It feeeels great, less horny but not like usual. Im hooked. I wished i filmed it 🤭
So today was the day that my gf found my panties in the draws. She didn't fine other thing but I dont know what to do. I told her I'm not bi but I just love wear panties when I perk off. In which it was a lie lol. But I don't know what to do now. Any advice?
I’m trying to get better at riding but struggle to do it for more than a couple minutes at a time. Every position feels so awkward to me and my arms always end up sore. Maybe I just need to practice more? But would love some tips
Growing a little disenchanted with “hypnosis” that’s just seizure inducing porn. I’m looking for some actual deep hypnosis, something that really messes with your mind
Also idk how to find shit on Soundgasm so please leave recommendations
I would like to attend a carnival party where I can dress up as a woman in total freedom... what outfit would you use?
I’m looking for some inspiration
As I sit writing this, I'm wearing black lace panties and matching bra. I had an experience with a sissygasm yesterday. I had my vibrator in and I could feel the pressure rising in my locked clitty. Then I cummed and I ate it. But the feeling wasn't as momentous as I thought it was going to be. Afterwards I cleaned up, but I didn't feel the need to wear panties or a bra. I know I'm over PNC and I have accepted I'm a sissy. But there is a slight feeling of moving on. But here I am in bra and panties thinking about sucking cock and being fucked. I hoping to document my journey for you sissy sisters out there to reflect on your own journey:)