This is going to be a fairly long and autobiographical post. I hope it’s not boring, but I think it was necessary to provide some context before asking the questions.
A few months ago, I started dating a woman 15 years older than me, and we’re very happy together. My partner has some very specific fetishes that, somehow, have always attracted me, subconsciously. While I’ve regularly cross-dressed in the privacy of my home, and that’s something I still do in her presence—and with her consent—the idea of receiving anal sex hadn’t really sunk in until I met her. I had occasionally played with my fingers in my anus and had tried briefly and sporadically inserting small objects, but only after meeting Belle and learning about her fantasies did I begin to consider becoming a member of the anal-only lifestyle club.
I want to make it clear that when I say “anal only,” I mean that from now on, I wish to derive sexual pleasure solely from anal penetration by Belle, and to permanently abandon direct stimulation of my penis.
The reason for this sort of partial chastity is that I want to please Belle and fulfill her fantasies of feminizing me and turning me into her servant.
Since I already behave and dress like a woman in private, I suppose I’m halfway there. However, I have several questions I’d like to clarify as I begin this process:
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The first question concerns sexual pleasure: Is it really possible to achieve orgasm solely through anal sex? I experience very pleasurable sensations during anal sex, but I’ve never been able to reach orgasm, neither with solo anal sex nor while being sodomized by Belle.
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I’ve read online about the practice of prostate milking. How often should it be performed? Is it used only for health reasons? Is it safe to perform? Does it involve reaching orgasm, or are ejaculation and orgasm through milking separate?
Naturally, I’ve considered wearing a chastity belt permanently, both to avoid the temptation to masturbate and to reduce and conceal the bulge in my groin. I’ve never worn one before, and I’d like to know if it hurts a lot to use at first, when I get my first erections while wearing it.
I’ve read that over time, the size of a penis “in captivity” can shrink to a minuscule, insignificant size, and that’s one of my long-term goals: to reduce it to little more than a useless protrusion. How long will it take to reach a negligible size, say, 1 cm? Will it return to its initial size if I stop wearing the chastity belt when it reaches a token size and is completely useless for sexual function?
-Currently, Belle sodomizes me with a 25 cm long by 5 cm wide strap-on. I usually wear a butt plug daily to dilate my anus and reduce pain: as time goes on and the frequency of anal sex increases, should we use a strap-on with a larger diameter to achieve the same level of pleasure and for me to “feel” that she’s penetrating me? Or should I stop using the butt plug? Will I end up suffering from incontinence when I defecate?
And finally, the most important question of all: how can I stay motivated and committed to the cause and to fulfilling Belle’s wishes when doubts arise and I think about abandoning our shared project?
Thank you so much for reading this far. If you can help me, Belle and I would be incredibly grateful.