r/Sissy

It will be nearly 1 year since my husband started his sissyfication journey and today my sissy partner goes by the name of Tiffany.

Tiffany's adventure started as a harmless experiment of trying codressing and exploring this side of always wanting to try it last June and my husband was hooked. It started gradually, panties, lingerie, makeup, wigs, women clothes to finally sleeping with other men while being in sissy mode.

And now, around 1 year later, we say down and spoke about it and she told me that she doesn't see herself going back and like being her sissy self. The dressing up, feeling cute and sexy and also the various men who visited her, well she's feeling at ease with her current situation and I'm so glad I had this conversation with her and you all don't know how proud I am of her.

So there are 3 things that got my husband hooked and during our conversation we tried to break it down to see what factors really brought us to our current situation.

1. Women clothing and makeup feel better

She told me that it was probably one of the first things that started and trying my panties for fun really got to her. They werre sexy, comfortable and really made her feel beautiful. Also introducing her to makeup was mesmerizing for her as she couldn't believe how beautiful her face looked all dolled up

2. Sissygasms

My husband was able to have prostate orgasms well before the sissy journey but there's a thing about getting fucked by man and suddenly started leaking cum that really fucked with her senses and feelings. I gotta agree on this because the first time she has a sissygasm while in sissygear was with my dildo. We were on our bed and she was fucking herself with it and climaxed. I could see the expression on her face and inside me I knew something changed forever inside her. After cumming she stopped and we joked about it but yeah, I remember. And as time went by and having more prostate orgasms along the line, she told me she prefers cumming like this now and sex in her head always ends with her having a sissygasm. Those thing are dangerous lol.

3. My acceptance of Tiffany

It seriously came up and I was surprised. But she told me that she wouldn't have continued exploring herself if I weren't letting her do so. I mean, I am a partner in this relationship, and I won't lie saying that I didn't love watching Tiffany get born. It was deeply amazing to see her progress.

We also talked about how a certain hypno (I think you know what I am referring to) messed her brains up when she was starting and I kind you not, she must have had gone over that all hypno 5-6 times already. So I think it had something to do.

This was my husband's sissy journey till now. We are definitely not planning on stopping because we were honest to each other about wanting to continue like this. I am not hiding that we had some challenges (mainly socially), but for what it's worth, our 2 close friends (couple we swing a lot before) know about the new dynamics and we're amazed how Tiffany's sissyfication started a while ago and they didn't know anything. They were impressed with the clothes selection and yeah, it's going great for now.

Sissyfication is a wonderful thing to explore. If you want to try it, I highly recommend, Tiffany highly recommends. Start slow and see how you feel about it. It worked for us. What started with a couple of panties tryouts became a full blown sissy adventure for us. Don't be scared to try it as once you cross this line, you'll realize how wonderful it feels for yourself. Also things always remain behind closed doors, so have fun.

Hi all, 20 m

ive recently been questioning myself and who i am or what i am, i was on porn and came across a hypno vid and it made me feel so horny and crazy.

Well since then i havent been able to get that sensation out of my mind and im wondering.... whats it mean to be a sissy? Do i have to have a particular body?

Ive always been straight but since that JOI hypno its a little different now...

Is this a phase?

Should i be concerned?

Let me know

Cheers

Ooooh that was so awesome!!! I was showering and decided to play with my ass a little. I started riding my black dildo(23cm/9 inch) and at some point I layed down in the shower in missionary position and thrusted my hole as fast and deep as I could. My dildo was going ball deep inside me and like after a min or two I felt like I was about to cum and literally in 30 second I squirted through my chastity on my belly. I felt like I was on the clouds, so proud of my self.

Have a bit of time alone later. Probably an hour or so. How girly should I get?

Hey there fellow sissies, I’m brand new to this subreddit, looking for friends I’m 21 and my names Jessica

Someone help. I need help deciding what to wear later. I have a brief timeframe today alone. Should I just go with a dress, or should I go lingerie/skirt etc?

So I just started a low dose patch but I’m terrified. I want to present more femme but it’s a huge step.
Yikes!

Hi all,

Longtime lurker, first time poster.

I've been on the fringes of sissy/CD stuff for a few years now, but have recently decided to go a bit further. I bought myself some cute underwear just to have, and I gotta say it looks and feels phenomenal!

Couple little hiccups though: I'm a very clearly masc man, and I can't really change much about it. My appearance is tied a lot to my job, and I don't live alone, so it makes it difficult to indulge in such things. Because of that, I don't see myself ever fully embracing this part of me.

That being said, I'd love to be in with a like-minded group of people who would be encouraging and nice to me as I play around and enjoy the feel of dressing up. Would I ever go further and do more physical stuff? Maybe, if life shifts in a way that lets me. For now, I'm content dressing up. I'd just like to share the experience with an encouraging group. It'd be nice to be around like-minded individuals.

If this post isn't right for this subreddit, feel free to delete, just redirect me to to where it would be the best fit.

Thanks so much.

Genuinely curious if your body count with men rose quickly.

Unintentionally spent the week being a naughty slut, I wanted to have a few naughty meets but ended up fucking nearly every day across the week.

Thursday: Went to a guy's place I met online. After sucking his floppy dick for 20 mins he admitted he was on coke so I bailed. Use viagra if you sniff ffs

Friday: Went to a club for Tgirls. Dressed up in white stockings and crop top with pink mini skirt, bra and panties. Blonde wig and pink heels. After sucking off 3 guys who didn't want to fuck, I was getting banged in front of a load of guy's when one of them shoved his cock in my mouth and I was getting it from both ends.

Getting spit roasted for a crowd was hot af but sadly only lasted for a few more guy's as was boiling and I was getting overheated in my wig. Ended up being fucked by 5 guy's including a massive BBC and finished up getting sucked off by a sexy CD

Sunday: Met a guy I've had previous with. He's a complete stud, bent me over straight away and shot his load in me after about 1min but stayed hard and carried on fucking me. After a few mins he gets me on my knees to facefuck me and tells me he's cumming again. I didn't believe him until I started to taste his jizz down the back of my throat.

Puts me on the bed and fucks me deep with my legs on his shoulders until he CUMS AGAIN inside me. Honestly im not making this up. After this he strapped me down to his fuck machine and had me in there for 30 mins which was amazing.

Monday: Drove to a guys place dressed in my French maids outfit and black pvc boots. He was naked when I arrived and I dropped to me knees to get him hard. After 2 mins he was stiff and got me to bend over so he could fuck me raw, 2 mins later he was finished. Not to upset about the short fuck as I'd forgot my lube and was kinda hurting. Squeezed his cum out my ass at home and ate it.

Tuesday: Met a guy I've met a few times before, normally spend all night partying with him so was looking forward to this night. Had my white and pink outfit on again, shortly after arriving he tells me another CD and guy are coming over to party with us, all cool with me.

Turned a bit weird as they were all on some hardcore substances which I won't go into but the guy who came over had a huge cock and absolutely railed me hard for ages, also got spitroasted again :)

After a while my host got jealous of sharing and took me to his tiny bathroom where he put my head in the toilet and fucked me hard while calling me a dirty bitch, made me lick the toilet seat and kept flushing.

Sucked the CD off too :)

Wednesday: As this was my last free day for a while I went all out. Got a guy to come round mine but he wanted me blindfolded. So I was kneeling in my living room wearing a schoolgirl outfit with a black stocking as a blindfold. I hear him come in and straight away a hard cock is shoved in my mouth, I was very impressed. After a few mins of facefucking he lifts me on my sofa and bends be over so he can fuck me, didn't last too long but was hot.

After that I drove to some guys house who'd I'd only exchange a few messages with online, bit desperate of me but was horny af still. His cock was massive! Big and thick but had a weird head on it I wasn't keen on sucking so I quickly got him to lie down so I could ride him. After I'd gotten used to his dick inside me I bent over for him and let him rail me hard, was intense but got in the zone so was loving it. Flipped me on my back and cummed inside me with my legs in the air.

At this point was about 1am when I got home but was still gagging for it so went back online and advertised that I could host. Eventually got a younger guy over about 3am, his dick was rock hard while sucking it but he never made a sound which was weird. Bent me over my sofa and jack hammered away for about 10 mins, I loved it so much his dick was a perfect size.

He stopped after a while and said he wouldn't be able to cum. I say no worries can I suck you off again. This turned into him fucking my throat really intensely, like I was nearly going to tap out when suddenly his load hit the back of my throat.

So I ended up fucking 11 guys and having around 20 cocks in my mouth, honestly Im not sure how it happened. Have a pic of the fuck machine I'll post in comments xx

i like the online sissy life style and gooning non stop but there is a problem i need to work and find a job but it will eat all of my free time how you keep a goon life balance

Because the sensations along the way make me more than happy☺️✌️

So basically im a sissy for over 2 years now and always took pictures with filters.
Now i am alone at home for 2 weeks and want to try out the makeup from my mom.
Pls give me some advice im so lost 😭

Sometimes I look back at my journey and wonder how much a person can slowly change without realizing it.

At first, I considered myself completely straight. I had a few gay incidents but kept telling myself it “didn’t count” because it was only curiosity or just a blowjob.

Then I became attached to giving oral to one guy regularly, and that was the point where I finally admitted to myself that I was bisexual.

After that, things slowly escalated: one guy became multiple guys, curiosity became preference, and I realized I was becoming more attracted to men than women emotionally and sexually.

For a long time I still resisted certain labels. I didn’t see myself as feminine, submissive, or a “sissy.” But after exploring anal and more submissive experiences with multiple men, I slowly started accepting that side of myself too.

Then humiliation/submission became part of it. Things like serving, obeying, licking feet, doing degrading tasks, craving validation from dominant men… even then I still told myself:

“I’m not a slave.”

But after meeting my first genuinely master-type person, something mentally changed for me and I started accepting that identity too.

What confuses me most is how every stage felt impossible to imagine before it happened:

Straight → curious

Curious → bisexual

Bisexual → more attracted to men

Submissive → sissy

Sissy → slave

Even crossdressing was something I once thought I would never enjoy, and now it’s part of me too.

Sometimes I genuinely wonder:

Was this always hidden inside me slowly coming out?

Or did repeated experiences and validation slowly reshape my identity over time?

Has anyone else experienced this kind of gradual transformation in sexuality/kink identity?

Hi everyone, I have a couple weeks in June booked off work and thought it would be fun to really try to feminize myself and take some time to fully explore being a good committed sissy. I would love some suggestions on what would be fun to post and ideas to try out! I love making content and looking forward to getting creative with my posts and trying out new things on camera I’m pretty open and have some money I’m willing to spend to achieve this.

I was also thinking of doing some polls if the posts get attention so people could vote on what they would want to see and follow along and the idea of being feminised by a group of people and fellow sissies seems really fun and something new for me to try.

I already have a few toys such as dildos and plugs, a few sets of cute lingerie and underwear, a cage, a wig but still really open to expanding this so any suggestions for this too would be amazing! sorry if this comes across as lazy in any way I was just super curious on what other sissies and people would like to see and ideas this amazing community has!

I’m also planning to get some stands and a ring light so I can try make some genuinely good content and fun angles

TLDR

I have a few weeks free and would love some fun suggestions to try whilst Im able to become a sissy full time for a few weeks

Hailey 💕

I started pretty standard with liking women and watching regular porn. Then at around age 17 I was talking with some guys while changing after gym class and for some reason the topic changed to homosexuality, and one guy mentioned that everyone will have at least one gay dream in their life. Weird and probably fake statistic but when I went home and jerked off I was suddenly thinking about his muscular body, his lips, how it would feel to touch his chest and his penis, and I came.

Fast forward and I am now regularly having sessions thinking about men. But I know they are all straight, so I struggle to imagine them wanting me as a boy. At this point I have been to a lot of parties and have seen how the girls dress, short dresses, skirts, sometimes with a visible thong or push up bra. I start imagining myself wearing this when I'm dreaming about guys.

Then eventually when I'm looking for porn I basically stumble upon caption porn, and eventually sissy captions. The fap roulettes inspire me to go futher, as they often tell you to wear specific clothes, use toys and where to cum. I start fingering myself, then use carrots and cucumbers. I also try tasting my own cum and giving myself facials.

Eventually I muster up the courage to buy a multipack of colorful thongs online. I end up wearing them basically any time I'm alone. I then finally buy a real dildo, every orgasm I've had up until that point pales in comparison. This is how I am meant to be satisfied.

Eventually I get my own place, and due to covid I get to spend all day in lingerie, with a cute dress or my maid uniform over it, I buy multiple more dildos that can vibrate, squirt and with suction cups so they can be floor or wall mounted.

And thats how I became a sissy. Don't really want to take it further with a real guy, but might eventually buy a sex machine.

How about you?

God I remember I used to be so straight. Wouldnt even consider guys. But that kink has turned me so fucking gay.

I love all kind of men. Feminine, masculine, skinny, big, buff, hairy, smooth, short, tall. AND I LOVE COCK TOO. (Yes also like every kind :3)

AND I wanted to saymore cute lovey dovey stuff about what I would wanna do to a guy but I forgor :p

So I have 2 dildos and 3 plugs. One of my dildos is just a normal dildo that I worship and love so much!! The other is a squirting dildo that is extremely difficult to use. So I hardly ever use it.

I’ve been searching Amazon lately for other dildos and have found a lot of thrusting dildos that also have a “heat” option on them. And I’m not talking about a sex machine, just a $40 thrusting dildo that has a suction cup.

Does anyone use them? If so how do they feel?

Also does anyone use knotted dildos ? I’ve also been thinking about getting one but I don’t want to hurt myself either lol

Any advice would be greatly appreciated! Im ready to do more anally stuff I just don’t know where to go next !

i have sucked dick and gave hand jobs but never have i done anything with my ass because of fear,im scared of the pain and i want tips on how to make anal sex less painful and feel better any tips from more experienced sissys?

Hey girls! So I've been dressing on and off for like a decade now but am still super closeted about it. At times I've been more public about it and have dressed more fem around friends and family but have since then reclused.

I guess I just want to avoid the questions and judgement. But it has always eaten at me from the inside. I want to be feminine so badly but I just feel like it will never truly be available to me.

I also have a lack of privacy at home and that definitely doesn't help.

Would love to hear how some of you have carved out time to be your pretty selves. Any advice or discussion is encouraged!

Thank you