So, a bit of background I guess. 26, been into femboy/femdom shit since at least 15? trawling back old emails I can find orders for (garish and ugly) girls clothing and sex toys from when I was 15. I've always been a loner, felt distant from people, didn't feel in charge of my own life, felt judged and ostracised, didn't know how to approach people, didn't have many friends or social life etc. I *may* have some form of Aspergers, I'd personally prefer to blame things on my own choices and real personality flaws than consider myself biologically disadvantaged, but if I was it would explain parts of my personality/communication. And for what it's worth I'd always been very skinny and androgynous. So I think the psychology of why this stuff appeals is pretty evident, it turns your flaws and insecurities into advantages, if you lack initiative you get to be acted upon, if you feel ignored you get to be the object of desire and attention, and if trying to overcome or ignore those issues is causing you stress than the act of dropping it all to larp as some kind of helpless bimbo is incredibly freeing. even the harsher stuff, the humiliation, is about turning anxieties into strengths.
As I got older, in bits and pieces, I've had a fair few vanilla opportunities with women and opportunities to indulge femboy-ism and other submissive behaviour, mostly with women, tried with guys a couple times but never committed, just felt wrong. But I think years of conditioning, plus general nervous temperament, and conditioning to be excited by screen stimulus as opposed to in the moment has neutered my sex life considerably. I've probably had like, upwards of 20 sexual partners of some level, actually penetrated maybe 4 - 6 women and almost never orgasmed from anothers stimulus. staying hard enough to fuck is very hard. I might technically be a virgin. Certainly had an uneven sexual experience (had lots of foreplay/bj's, eaten a lot of pussy, hardly ever gone PIV, been pegged and some other kinky things). I think the awkwardness of regular, vanilla sex has only made the taboo kinky stuff more attractive
To be honest, I don't know when I decided that sissy-adjacent fetishism was unhealthy and I wanted to avoid it. I can find reciepts from url blocking software from when I was at least 20, but I suspect I've pretty much thought it about as long as I've been doing it. I spend most of the year in a kind of passive-denial, where I don't do much to avoid the content online but don't engage irl, but maybe once or twice a year I think fuck it, get some lingerie or clothes, toys, etc, make accounts on alternative dating sites, etc, maybe meet a girl who's into that stuff. I suppose one thing about my personality is that I'm self conscious enough and risk avoidant to have not exposed too much of this in real life, not having had to walk back on it or make eye contact with friends knowing they know.
At some point over the last year, on my way to turning 26, I decided that not believing in my own agency was holding me back, personally, socially, mentally, sexually, I've basically been trying to live in a more 'Yes Man' style, like living by the motto 'Fuck it, why not?', but also not be afraid to approach and ask people things on my own wherewithal. I won't go into what kind of stuff that has included bc it's approaching doxx territory but it's involved group holidays, physical challenges, charity drives, just 'stuff' in general. It's been good for my confidence. During this period, I'd been on my probably longest string of abstinence, and a girl I'd met on a dating app invited me to do some mad outdoors activity, which involved driving all the way to another country. Well I met her, it was great, we did out outdoors activity, we had something approaching sex (worrying that after like 21 days, and with 2 taladafils I could hardly keep it up, but oh well). But it was more than that. She was like the most warm and open, non-judgemental person I'd met. She was so easy to talk to. I'm normally a guarded person, and I can be a little judgemental and a little afraid of being judged as well. There was none of that. Nothing about her made me cringe, I didn't feel like I was looking over anything to be with her. We made plans to meet a couple weeks later, she was moving back to my country so it would be easier to meet in the future.
We're at mine, and we're getting into it, and she asks, what are you into? I'm hesitant, and she said, no, like what *are* you into? I noticed you liked a bit of teasing last time? I hesitantly tell her, well uh, sometimes I wear lingerie I guess. She tells me to show her, and I go to the car to grab it, because I'd pre-emptively hidden it in case she saw it poking out from somewhere, in fact a testament to how non judgemental she seemed is that she seemed more sad that I thought I'd have to hide it. I let her pick some out for me and I put it on, and she kind of continued, okay, then what? what do you do with your lingerie on? I kind of sheepishly admit that I like to wear chastity sometimes, and to my surprise she says I *love* chastity, and tells me to put it on. I'm aware that this is very much not a porn sub, so I won't go into what we get into, but we definitely had a lot of fun, she's a good tease and she (claims) that this is the first time she's had an orgasm with a partner, that she never really cums in front of people. I'm mostly just astounded that it's even happening, this is the first time I've admitted this to anyone who I haven't specifically sought out for femdom stuff.
When we're done, she asks a few questions. If I'm gay, to which I say no, I tried meeting with a guy once but it just felt uncomfortable, if I might transition, also no, I just like this kind of stuff I guess, both get a hmmmm response. I suppose I'm feeling insecure, and the amount of alcohol and frankly anti-anxiety meds I've taken to get this far probably aren't making me think the best, and I can't really remember how but I do remember showing her a thirst pic of me fully erect, kind of to prove some level of masculinity? that probably wasn't very attractive. Well, we think loosely about our plans, she admits she doesn't think we'd be right for a relationship but she'd like to keep seeing me as friends (with benefits), and I'm a little upset that we're not going to have a full relationship but I'm just glad to have her, and we fall asleep in each others arms.
When I wake up, she's gone. She's driven home. There's a text waiting for me. It says on the drive home she's had a think and I 'have a lot of things to figure out and she doesn't have the bandwith'. A couple of other things that I don't really buy as factors as well, like not wanting to watch a 2 hour summary video of a nigerian soap opera on my TV, and apparently insulting one of her hobbies. I guess she's right, I did have things to figure out, I was conflicted about this kink and I have been for a long time. At first it feels like she really pushed me into that state, enjoyed it, then judged me for it, which felt awful. After a bit of time I can accept that perhaps being visibly conflicted and insecure about it afterwards might have been a bigger turn off. But I was so angry, and I still am. Angry at her, angry at myself. I can't help think that well, it never would have happened if I had held fast. I've never felt so able to be myself with a person, after a life time of being guarded, living under personas, and it's shattered. I have no reason to think I'll get that opportunity again, but I have to keep trying. So, that's my motivation for now.