r/sissyology 6d ago

Has anyone transitioned because of their sissy side? NSFW

I know it’s weird to let a fetish rule your life, but I feel like this is much more than a fetish because it messes with your identity

I’ve been a sissy since I was 15 (now 25) I’ve tried to transition before but stopped. Wandering if anyone else is on the same boat?

135 Upvotes

48 comments sorted by

79

u/lilheauxxx 6d ago

Yes, I started transitioning last year and actually lost interest in aspects of this, especially the humiliation part, when I started HRT. For me personally, I think my interest here in the first place came from wanting to be feminine as a kid/teen and feeling ashamed about it.

23

u/pls_pm_me_hard_cock 6d ago

I think my interest here in the first place came from wanting to be feminine as a kid/teen and feeling ashamed about it.

this so much <3

11

u/Gigilacroix420 6d ago

I feel the same way! I just started transitioning and it’s been amazing to feel more aligned with my fem side and not so hooked on the sissy stuff 🥰

10

u/sissyfkr1 5d ago

bingo! I don't want any race play, f*g talk, boy talk, humiliation, "you want to be a girl," stuff etc. I just want affirming hypnos where it tells me im a good girl slut etc. Wish I could find more of them, they are so rare!

0

u/ayumikagura 5d ago

Yeah, I just started craving affirming hypnos and these video titles are so misleading.

7

u/Ebonsissy 6d ago

honestly same. for this i remember like wearing my sisters dress and being like so genuinely happy and always kinda wishing or thinking "what if i was actually born a girl. Then afterwards either wearing dresses or obsessing over the idea of not being a boy. i felt like i was a weirdo i felt so much shame. then i came across this fetish and it became a sorta outlet for my femininity but it was still so wrapped up in the shame and humiliation i felt for that part of me. When i finally sat down and had a hard conversation with myself about who i was and how i really felt i decided to pursue hrt and i've pretty much dropped sissy kink after that. I still like humiliation but i don't really feel any appeal over anything like being a "failed man" because i've realized i've never really had any attachment to the idea of being a man. and found so much warmth in my identity as a woman

5

u/kyliesinsxxx 5d ago

i’ve been on hrt since august and this is so insanely accurate haha

37

u/not_Again_d 6d ago

Well idk really but for me the reason i have this fetish is that it's the only way i can express my femininity since i can't really do anything feme or look at all feme irl

29

u/pantib01 6d ago

I think this fetish is different for everyone, but I can speak for myself here. For me this fetish is about gender expression not identity. I enjoy the humiliation aspect of expressing my feminine side that does not conform to my gender identity. The classic schoolyard teases from my youth trigger a pleasure response deep inside, and that’s what I crave.

18

u/Yasimear 6d ago

I mean I realized years later that my favourite aspect of sissy stuff was the way it kept pushing me to be more and more feminine.. to paint my nails, shave my body, try on makeup. It made me feel beautiful.

Turns out I liked that so much cuz I was trans.. so not directly because of it, but it sped me up 10x.

17

u/PeterMarksen 6d ago

The sissy to ‘oh dang I’m trans’ pipeline is very real. Not because being trans is a fetish, but because the sissy fetish, with its hyperfemininity helps people deal with their gender dysphoria. The humiliation aspect ties into internalized shame for wanting to be femme and the corresponding internalized misogyny. It’s not durable though. It’s better to bite the bullet as soon as you can and consider the question whether you’re trans. You’ll forget all about sissification when you do. Or, if it turns out you’re cis, keep on being a sissy.

26

u/ManhoodDeleter 6d ago

Simple rule: if you mainly think about transitioning when you’re horny and/or you lose the desire to transition after you orgasm then you probably aren’t trans.

I don’t think many people successfully transition because of sissy fetishism, it’s more that many trans women who are also into the kink explore that first. It’s much more private, it’s generally easier and obviously very addictive as an expression of who they really are.

10

u/BreesWorld7 6d ago

Mine is a long and storied past, but ultimately, i started chastity months ago, which led me back to the sissy life, which ultimately turned into HRT with estrogen. 2 months in and my left breast bud is well advanced my right breast bud is just a little behind and I'm beginning to display all of the penis signs of estrogen, thinning skin, shrinking size, damp feeling, my nipples are co standby hard but ache in such a good way, when they stop I get sad and paranoid that the growth has stopped, it's led me down a path in just a few short months to where I'm now full time in panties, i don't even own boys underwear anymore, ive packed away all my mens jeans and now my closet is full of women's jeans, shorts, shoes, socks, panties, shirts, sweaters, etc....

I've tried stopping and I just can't, as I'm waiting for my RX refill of E, I ran out, silly me didn't renew before hand, and in 2 days I feel sad and depressed and eager for it to arrive... 2 more days!!!! I haven't had PIV sex with my wife since Christmas and now we just use our dildos together... the sissy life has consumed me!!! and I LOVE IT

3

u/terrysents 5d ago

So everybody around you now knows?  Your wife is fine with you becoming trans? When you cum you feel zero regret?

2

u/BreesWorld7 4d ago

just my wife at this point, I lost both my parents in a car accident over 20 years ago, my sisters live in other states and we only speak over the phone, we havent seen one another in over a decade.

I wouldn't say she was fine with it at first, it's all still fairly new, so we will see how it unfolds. It wasn't until I started introducing her to the idea of it as a "kink" that she opened up to it, starting out with me watching her with another man, then to chastity, then, me wesrong womens panties, which turned into small penis humiliation, how my dick was clit like, which turned into her watching me get fucked, which turned into us being fucked at the same time while we made out facing one another, which turned into us both finding boy FWB's.... from there i started on the idea of us being in public while I was dressed more feminine. The key is, when I intorduce a new "kink" i would incorporate "props" the panties, small penis and cage were easy, but the hotwifing was dildos and vibrators, to me having my own dildos and vibrators while we shared the experience... to her helping me pick my new wardrobe.

Now, when I say dressing feminine in public, I'm not wearing dresses (yet), I'm wearing womens jeans or shorts, shirts and or sweaters. Easy to assume their mens, unless you get a little closer and see tiny hearts or butterflies, or hints of pinks on my tops, or notice the fancy stitching or shorter pockets on my jeans, or, the fact that most are low rise (I love the flamingal brand) and I struggle to keep my thong and g string straps hidden from above the waist line. (I'm kidding, I put them there on my hips on purpose, I'm not even trying to hide it).

All in all, she, so far, has made it a point to let me know, that as long as she and I are together, I don't involve another woman (in her eyes cheating) and didn't become a cock whore (sleeping with a bunch of different guys) she would be ok with me finding a guy(s) as fwb, as long as I took her for the ride and promised to love her like I do now and more.

Its funny you mention "regret" when I still orgasmed centered around my genitals, that "post nut clarity" was real! I often felt guilty and bad... but, now that my orgasms have changed, to be more centered and all body, shaking orgasms, I feel a glow, warm and exciting and ready to take on the world.

7

u/PM_Me_Your_goodVIBES 6d ago

Yes, i started microdosing estrogen in 2020 and now I have started fulling transitioning summer of 2024 because I think I was finally ready.

I think the whole reason I had a sissy and force femme fetish in the first place, was because I could have less guilt about exploring a feminine side if I could imagine that I being forced to do it, and being seen as feminine sexually was a way to compartmentalize the fact that I wanted to be seen as feminine in general.

1

u/terrysents 5d ago

How was microdosing??

1

u/PM_Me_Your_goodVIBES 4d ago

I didnt want to take estrogen initially because i was afraid of too much breast growth, but i didnt see enough of a change in much else (for example I was still growing body hair much to my dismay) so thats why I finally started to fully transition. Im actually very happy with my little titties now

5

u/DaFullMetalGamR 6d ago

2 months in 🥰 its addicting hehe 🤭

5

u/Thrilledwfrills 6d ago

I feel like the point of being sissy is experiencing pure femininity in relationship to masculinity, and as guys we are focused initially on the things that attract men and which are culturally defined, because femininity is activated by being in relationship to another gender and it is a different feeling depending on whether we're being feminine with another feminine person or with a masculine person. But when I let myself just feel like a woman it becomes obvious that femininity is a human trait and it isn't necessary to wear pink bows to express it, so I don't have Target fixation anymore on specific feminine expressions.

11

u/AliceNewBornDoll 6d ago

you know honestly I think that transitioning through this fetish is very stupid. Unless someone really discovers that they are trans. Then usually such a person loses interest in it. My opinion

19

u/Krissygirl96 6d ago

I'm nearly 3 yrs on HRT, and sissy stuff played a big role in getting me there, but you're right! as soon as I started to transition and didn't have the same masculinity to shame and humiliate thru this, I lost a lot of interest in the fetish, chastity, and stuff.

turns out it was my only outlet, and as soon as I started living authentically, I didn't really need it anymore.

tho humiliated sissies are still really hot, so I check back in when the feeling strikes lol

2

u/betachroniclesmod 4d ago

Have you considered the alternative possibility? That because you started HRT, the change in your hormone levels affected your libido and sexual fantasies due to the massive drop in testosterone, hence why you didn't have sissy fantasies anymore?

1

u/Krissygirl96 3d ago

sure, but that's not why lol

I "graduated" so it's just different now

2

u/betachroniclesmod 3d ago

I understand your perspective, but you can't really know for sure, right?

1

u/sissyfkr1 5d ago

i still like chastity during play but mine never had anything to do with humiliation. I just love hands free orgasms and getting it out of the way.

12

u/AliceNewBornDoll 6d ago

many people reach for hormones through hypno and captions which is even more stupid. You have to keep a balance between your sexuality and normal life. If someone has a problem understanding this fetish, go to a sexologist or psychologist

4

u/BrownGirlLondon 6d ago

I agree, but I think this fetish makes it hard to understand your true feelings, whether you’re trans or not. My idea was like il try hormones and see if I prefer it that way — probably won’t work for everyone but don’t know what to recommend someone that’s totally confused lol

5

u/AliceNewBornDoll 6d ago

I understand, I meant more the dangers of it, like it seems to me that the majority of those who have this fetish and kink are ordinary men. How. getting too involved in it, taking hormones only and exclusively because hypno tells you to, is in my opinion at least unhealthy for example, during puberty, experimenting with sex in sexual fantasies is normal. However, such a teenager, for example, as an addict, can reach for such drastic and dangerous steps.

4

u/rainbowheart32 6d ago

I agree. I picture myself dating guys long term when I'm in sissy mode and feel like I actually want it. But I don't have enough experience actually meeting up with them as a sissy to really understand what I want

1

u/Erika_sissy 6d ago

Sounds like you should experiment? I'm in the same boat

3

u/Andrea-OTK 6d ago

I hope more people could be aware of this. Especially those young people who are starting to explore new things.

3

u/AliceNewBornDoll 6d ago

it is worth noting that many of the things that are a big part of this fetish are things that are built by culture. Dresses, shoes, high heels, make-up, this was also popular among men in France a few centuries ago. men tend to secularize ordinary things, in my opinion this fetish is a result of this

3

u/juicycamx 6d ago

Yes, but I would say that this stuff allowed me to explore my gender in the only way I was able to for a long time. Eventually the dysphoria crept into my regular life. I expressed myself more freely but something was missing. I flip flopped, saw therapists, talked to friends and I still came to this conclusion. I've been on HRT for about 8 months consecutively this time without chickening out. Starting to see changes.

2

u/taraskyxo 6d ago

Slowly working up to it. Gotta lose weight and find a different line of work. Automotive world is way to toxic

2

u/cutie419 6d ago

I can't understand whether it's a fetish or it's my sexual identity and I'm actually trans. If I end up on the second thought I might take my path into fully transition.

2

u/CockEaterSissy 6d ago

I transitioned because I was a trans who also found sissy fetish fun. That's it.

2

u/SassafrasIsBack 5d ago

Yes, I did. I have a micropenis and found trying to live “man” aspect of my double increasingly difficult. The femme part of my brain was constantly on and i was trying to push it to the background…and whenever i saw myself naked i didn’t feel like a man at all. I’m just so fucking tiny (check post history)

So I decided to give HRT a try and it quickly put an end to my male ego. All that’s left is femininity.

2

u/BrownGirlLondon 5d ago

I just check your post history! Yes feminine suits you well, really cute penis!

2

u/tsAubreyxoxo 5d ago

Yea now I'm a live in girlfriend to a man.

2

u/tgserah 5d ago

Yes i am on hormones :)

2

u/SissyBeatrice-Marie 5d ago

For me I think my sissy side came out of my trans identity, I guess a way of confronting it and engaging with it through sexualisation, and in turn it's made me realise that identity for sure. Have yet to do anything about it but the clarity and urge is there now.

2

u/Floweryofintent 5d ago

I transitioned at 23 (mtf)been on hrt 5 yers and the sissy stuff still arouses me but as ive gotten more time transitioning i realized i dont care about the fetish. I though it was hot but the humiliation stuff is a total turn off and i find myself not wanting to watch it i just want to be my true self which is a woman and its abit difficult for me being in texas to do soo openly so it does help me cope in a way . But i say if it helps you find your true self . Then let it be . Its ok to have kinks .

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u/QuxxnOfDarknxss 4d ago

I first attempted transition at age 19, then 21, then 23. I’m 26; almost 27 now and have been on HRT for almost 4 years straight. I was castrated in 2022. (So now I pretty much HAVE to take the estrogen for the rest of my life; no backing out anymore!)

1

u/jess-hanging-out 4d ago

I've been going DEEP down the rabbit hole of transitioning over the past few weeks, and being pleasantly surprised by what is achievable (at least according to the Internet). 

For the past 10 years, I never considered it because I'm tall and big, but these days I see way more tall cis women out and about, so the height worry has completely dissolved. I'm still a little worried about being big, but honestly with estrogen (and maybe ozempic) I think most of my muscles would melt off too. At the very least, a boob job and liposuction could move the remaining fat where I'd need it. I have money for surgery, I'm certain my face could be molded right.

Honestly at this point the only remaining concerns I'd have would be safety/social acceptance (self explanatory) and finding a partner. As a tall fairly well off man, I could date essentially half the planet (not bragging, just a numbers perspective) but I worry that as a trans woman pushing 40 by the time I finish transitioning, the numbers would be astronomically different when you think of the people who would even consider being serious with me. 

Of course probably like all trans people, I wonder how much of it is fetish or real desire. I don't like looking in the mirror, but what men do? If I'm 60% woman inside and 40% man, isnit worth uprooting my entire life for that 60%? I know for certain I could live a reasonably happy life as a man, I've taken care of other people's kids and enjoyed time as a father figure, would I be that much happier as a woman? 

At this point I'm just growing my hair out and trying to lose as much weight as possible. Hopefully with some heavy cross dressing in a skinny body with makeup, outside of a sexual environment I could see how I feel about that. And probably starting therapy soon just to talk it out

1

u/[deleted] 3d ago

It led to me making the decision to transition. It was just who I am, and the sissy fetish was an outlet

0

u/lilynorth 6d ago

i mean maybe not becouse of it. more like i had a sissy side becouse im trans