Anal Invasion

You probably know that my wife can’t have sex due to health issues. She’s offered to help me relieve some tension, but she always pulls back at the last moment. I’m considering purchasing a strap-on anal dildo for her to use on me. I usually wear trousers while I keep skirts indoors as indoor attire. Although I don’t fancy men, being under her control appeals to me. I can secure myself with handcuffs over a stool, leaving no way out if she decides to proceed. Could anyone advise on the best approach? Is it painful? Will it cause any harm? It’s been a long while since my last time in there, and I don’t want to injure anything now. Can this method provide satisfaction? What is the proper way to go about it?

I may not be the best source for direct experience - I've experimented with butt plugs but found them lacking, and they are a firm boundary for My Lady (regardless of direction), which covers my entire experience. That said, I know quite a few people who really enjoy strap-ons. Both Dommes and subs seem very happy with the sensations involved, reportedly without any negative consequences. Having watched a man get fisted almost up to the lady's elbow, I can confirm that the anus and rectum are capable of handling substantial sizes. The key is ensuring those sensitive, delicate tissues stay relaxed and well-lubricated to prevent serious injury. The combination of high bacterial presence and fragile tissue poses an obvious health risk. As long as the strap-on isn't one of the "porn" giants in terms of size, you should be fine. Will it hurt? Yes, if your muscles aren't relaxed and lubrication is insufficient! Aside from prostate massage (which I haven't tried), I don't see direct physical satisfaction coming solely from anal play. An orgasm can certainly result from psychological triggers like humiliation or a sense of being violated, rather than just the physical stimulation of another body part replacing penile sensation. It really depends on what triggers your sexual arousal. However, there's something else about your post that concerns me slightly. If your wife "backs out" when you ask for relief—which I assume means direct contact like a blow job or using a vibrator—I'm not sure how she will be convinced to handle an assault weapon like a strap-on? Perhaps discussing the general concept with her would be a good starting point? I'd suggest that you find a friendly ProDomme experienced in wearing a strap-on, give it a try, and see if it suits your needs—after explaining your reasoning to your wife. Based on what I've observed, strap-on play isn't just something you do instinctively; some learning and guidance are advisable.