Maybe, since your wife is open to the idea, but might need some guidance, you could consider finding a friendly dominatrix. I’d imagine they’re rather versed in the art of pleasure of pain. You could have a nice evening having said dominatrix showing how rough is okay, and how rough is too little or much.

I mean, since it’d be cheating for you to get too off on that, you could wear a nice chastity cage, and be properly hogtied with your butt up. If you trust your wife with the safe word, you could even have a ballgag, so no flirting with the dominatrix, you know. I also recommend a mirror setup, in front of you, where all the buttplugs from the size of the pinkie, to the size of your fist is visible to both you, and your wife, but your wife also has a proper view of the actual inseriton, as it is a demonstration purposes afterall. Maybe have her a seat, with some red wine and good cheese, maybe few grapes or cherries too, for the process. If she wants, she could wear that nice evening dress with (or even without) some nice lingerie, since you’re having guests over, afterall.

Also, if your butt is too hairy for her to get a proper view, the dominatrix probably knows how to use wax strips to make sure the way to your hogtied, newly hairless, butt would be sufficient.

I’d imagine the first plug would be so easy to insert, that it’d prompt the dominatrix to skip one or two plugs, as she has a nice pleasant banter with your wife about your disposition. Perhaps your wife shoukd also feed the wine and cheese to your guest, since she probably has her hands too lubed up to touch the food herself, but it would be rude not to offer anything for the guest. And of course after few demonstrative insertions later, it’s important for the student in this situation to have their turn too, with your guests hands assisting with the insertion. And eventually, when you get to the bigger and bigger plugs, you probably won’t even need more lube, as you’re so lubed up, and squirming in that lovely, lusty pain, having the two newfound friends having an engaging, giggling, converstation while shoving that fist sized plug in and out of your stretched butt.

But that’s just a serving suggestion, I guess. Anyways, sorry for wandering off.

For the photographing thing, if you’re not happy with your body, work on it (as a less fattie than I used to be, I recommend the gym and dropping extra added sugar from your diet). If the hair is the problem, it’s okay to shave. But I’d say the biggest thing is to have proper lighting. There is a reason why the ringlights are very popular amongst “influencers”. And just a little tidbit of information: make-up artists who train for video production do get a lot out of being on a porn set, as there is a lot of skin that needs to look good for the camera.