Chastity update - Day 21

Today is my 21st day without penile stimulation. I wear a chastity cage a lot of the time during the day but not always. I’m self-locking. From day 10 to day 20 my libido was pretty low. Around day 15 the cage rub was getting a little too much for me, so I stopped wearing it a few days. Last night, I was feeling horny, so I put my cage on and watched a little porn. I love watching guys with thick dicks fuck forever without cumming, which I’ve never been able to do. I’m not sure what my longest period without an orgasm has been, but I won’t celebrate a new ‘personal best’ until 30 days.

I’m questioning a little why I’m doing this today. I know I’m going without a physiological release, and I can feel that a bit today. But I know why: in orgasm denial mode I feel connected to the real me who thinks about gender and sex. When I fap, I basically think about gender and sex only to stimulate myself via fantasy while fapping and never outside of that 5 minutes every other day or so; it is so split off. I’ve done that. I know where it leads. I want to try something new. I’ll continue to play this by ear.

I think going to that gay chastity event that I posted about on day 10 was really eye-opening for me. I love sucking cock and being fucked, but I’m not attracted to most men and some things about gay hookup culture turn me off. Another piece to being a sissy is ultra femininity. I like wearing feminine things. I don’t find it humiliating. I don’t want to dress up like a maid or other role play. I’d rather grow my hair out than wear a wig (I’m privileged to be able to do that).

I appreciate some things I do like better now. Even if I don’t see myself as a top or alpha, my attraction to women is robust; if I found someone who I matched with psychologically, there’s a good chance I’d find them physically attractive too. I want to have sex with women. I want women to see me in my cage. I don’t want to take on a traditional masculine sexual role in a heterosexual coupling. I would now say that topping causes gender dysphoria for me. I want to be primarily submissive. I’d rather not have penis-in-vagina sex; I’d prefer to use a strap-on; I’d prefer not to come and to focus on my partner’s pleasure through oral, strap-on sex, and cuckoldry. I’d like my partner to be the dominant sexual figure in the relationship. I don’t think I want a female-led relationship though (egalitarian is my norm), because that kind of feels like painting over the rest of the relationship with kink, and there are other important things I want to pursue in life outside of kink.

For a long time, “sissy” was a good label for me to describe what I’m into. Now, that may have changed. I am a feminine guy; that’s a gender thing. I identify as pan but I’m mostly attracted to women. I know I feel pretty dysphoric using my penis during sex. I’m submissive. I really like chastity. I think I’m a feminine male sub. I think I’m looking for a femdom or otherwise kink-compatible woman partner. It sure would be nice to have some friends with benefits too. Maybe a friend who knows I lock or a couple guys who I know are STI-free and I could suck their cock once in a while.

At one point in this journey I was trying DIY hormone replacement therapy through what I could buy over the counter. I’ve avoided lifting weights for years, wanting to shrink my upper body to look more femme. With this new idea of what I’m looking for, I think I want to put myself out there and try to meet people again. I’d like to be physically fit, and that will help me. I should keep developing my sense of gender and style.