Finger yourself?

[biguycancun]

Backstory: I spent over two years in chastity getting regularly fucked by a TS dominatrix. At the beginning it was more abuse, allegedly to tame me, but by the end I was a more than willing sub, never allowed to touch my uncaged cock but experiencing dripping orgasms from having my ass fucked by my master/mistress and others.

This was several years ago. I eventually parted ways with her when she became too involved in drugs and I felt I was in danger. I have two remaining "conditions" subsequent to those years. First, while functional and most times satisfactory to both my male and female partners, my cock is noticeably small, much smaller than it was prior to my caging. Second, I can yank on it all day and not cum until i penetrate my ass with something; a dildo, a brush handle, or most conveniently my finger or fingers. I don't need to mess with my prostate, I just need to have something up my ass.

And besides these complications, I find myself missing those times when she would dress me and make me earn my keep by being rented to patrons of her club for sex. While I don't think of myself as trans, being in stockings and heels always resulted in the most intense anal orgasms I ever experienced. And as I'm pounding my own ass, I find myself slipping into those memories more and more. Weird, no?

[KDaddy23]

I finger myself every time I shower but it seems to me that in your situation, you got... conditioned by that TS dominatrix; if you weren't allowed release unless you're being fucked, your body... gets used to that and your mind is used to it, too. Is it weird? I wouldn't say that it is - it just is what it is for you. I've jerked off with a finger or two buried in there and, oh, yeah, whew! But I can jerk off without doing that and... that's that; back to whatever I was doing. My question to you is: Do you perceive this as a problem?

[csreef]

I fingered myself when I was 13ish, and exploring my body. And that was it.

[Jazminedress]

no, nope, not at all

First off, I did not squeeze my ass into a tight dress to do all the work myself, thats what a partner is for.

Are you weird, the simple answer, who gets to judge whats weird, the way I am confuses some people, but it is what it is

[biguycancun]

My question to you is: Do you perceive this as a problem?
No, not really. And I understand enough about human biology and psychology to realize that it's a matter of conditioning. I'm conflicted about the cross-dressing aspect both physically and mentally. I don't consider myself "trans" although that was what my "customers" were paying for. But the thrill of being extremely passable and stimulated by the accoutrements and fetishizing keeps intruding on my maleness. And part of me wants to give in to those feelings while part of me rejects them.

[cornholejoe]

may be a problem for you when i get a finger or fingers up my asshole a man or women is doingme