Some questions (sizes, pain, commitment, and love)

[Ness]

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:

• 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.

• 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.

[AnalLover]

HI Ness,

I can only attempt to address three of your questions; and even then I can mostly only speak to my specific personal experience. For some (or perhaps all) of these questions, there is probably no single “correct” answer.

Is it really possible [for a male] to achieve orgasm solely through anal sex?

Reading this forum, it is clear that some females do orgasm solely through anal sex. However, while I have read some men say that they do/have orgasmed solely through anal sex, I have not heard/read it very frequently. In my own personal experience, it has probably happened for me less than 5 times in 40 years (thousands of episodes) of frequent anal toy use. I have to have some sort of penis stimulation to orgasm. However, I so much enjoy the sensations of the anal toy use that I don’t always even try to have an orgasm. All I can suggest is keep experimenting and find what works for you.

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?

That depends upon what you enjoy. There is NO “should”! With practice, your capability will likely increase. You may or may not choose to increase the diameter and/or the length of the toy. You may want to experiment with using multiple toys at the same time. Do what feels good for you. If there is pain, STOP, take a break, and if/when you are ready, continue more slowly, carefully, etc. Every person is different, everybody feels pleasure differently, etc. Don’t every think in terms of “should” – other than you should use plenty of lube, you should stop if it hurts, and you should be careful.

Like using toys, you may or may not choose to be fisted (whole hand / arm inserted) – most males can, with practice, receive the woman’s arm at least up to the woman’s elbow; some men can take a woman’s arm it even deeper; much depends upon the size of the woman’s hand. Taking a man’s hand or arm is possible for some men; it all depends upon size of the hand/arm and the amount of practice.

Will I end up suffering from incontinence when I defecate?

I believe that most or all the people on this forum would say that the answer is “no”. In my opinion, the negative comments that one hears about incontinence are either without merit, or the problem is the result injury caused of violent insertion, etc. Unfortunately, this is not a subject that most medical doctors receiving education about – some of them just tend to repeat the common myths they heard when they were younger. (Even though I understand that you are not gay, if you can find a gay-male-oriented physician, you may find more well-informed advice on these subjects.)

However, there may be different “stages” along your path. There are likely to be certain times when you may be more “loose” and prone to “accidents” – especially early in your stretching evolution.

My experience over more than 40 years of regular anal toy activity is that there were occasional periods of time when I had to be careful not to fart (for reasons you can imagine). Sometimes things were on the loose side. However, as time passed and with more practice, and with modest sphincter-tightening exercises, my sphincter muscles actually got stronger and stronger. Nowadays, if my wife is fisting me, I have to be careful not to “crush” her hand/wrist/arm if I squeeze my outer sphincter.

I would also say don’t “freak out” if you have times of “looseness” and have an accident – it happens. Just perhaps take a break for a little while and also look up how to do tightening exercises.

Again, everybody is different. Their bodies are starting at different points of conditioning and will also react differently to the activity. Also, the activities are always different (how much force, how much speed, how much lube, diameter of toy, length of toy, angle of insertion, etc., etc.) You just have to find what is right for you and adjust as you go along. Very important: communicate with your partner regularly and constantly about what feels good and what is uncomfortable, and especially if there is pain (“STOP”).

Also, don’t ever put yourself into any situation where your partner is not listening to your feedback and is not modifying their actions according to your instructions and feedback. It is possible to be seriously injured – and even have life-threatening injuries – from violent anal toy use / fisting or toy use / fisting contrary to the recipients instructions / feedback. However, in my personal, non-medical opinion, proper anal toy use / fisting is extremely UNlikely to cause any problems.

Most of all, do what you enjoy and what feels good.

[Ness]

Thank you for your advices, specially regarding the mandatory communication between partners. We’re fine in that regard, but it’s important, of course.

After your comments, I feel more comfortable and confident now, I’ll tell you how things go!