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No one is going to know the two of you better than the two of you. While it can be fun to swap techniques with other players, most "mentorship" relationships are unnecessary and often smoke-screen for toxic dynamics.

My favorite book in my library to loan to the recently-interested is "Screw the Roses, Send me the Thorns." It's certainly "classic" and legend has it that it was orginially laid out on a copy machine, but it remains one of the best survey-level resources out there for loving people doing this stuff because its fun in a non-commercial setting. Revolutionary for the time when most media was centered around Commercial Domination(tm.) A classic then, still excellent now.

I have so many "technique" books it's hard to narrow them down, but the first I would pick up is "Jay Wiseman's Erotic Bondage Handbook." Rope is useful, rope is cheap, rope is versatile, and with a few simple guidelines rope is remarkably safe. The biggest guideline being "don't do weight-bearing rope unless that's a specific fetish you're into and have spent a few years getting good at it." This book isn't about Japanese-style rope with an eye towards moving on to suspension, although I have books like that and I love them. This is about using Western style rope to keep things out of the way while having safe, sane, and consensual sexytimes. Simple techniques, creative applications, and a thrumming focus on safety make it a great start.

Comboing the two should give you a pretty good start on some neat ideas, save you some dosh by making it easier to put together a toybag that's not going to require a lot of cash outlay, and hopefully keep you away from handcuffs. I own a pair, I use them for capture play, but the can be prone to causing injuries both superficial and serious so you really don't want to be moving around while wearing them. Rope may not be 100% safe but it's certainly safe-er.

If you're interested in branching out a bit more, or you learn better from videos, or you would like to get your education and your porn fix at the same time, kink.com's Kink University has both a commercial site and a free sample feed of guest teachers that cover a wide, wide variety of activities with a focus on learning enough skills to have fun while getting an overview of what the kink/activity "is."

If you don't mind being marketed to a bit, Extreme Restraint's XR University and their Pornhub mirror, which is not verified so I won't link it here, are also excellent. Generally the two hosts bring in a guest star and speak to them about a certain kink for the first half of the vid, then do a hands on demonstration for the second half, interspersed with two-three commercials. The good news is that they go very in depth on the products used, make recommendations for ones they particularly like, and make it clear where they can be purchased. The maybe-bad news is that's because they sell them through their online store and are doing this to make money. Personally, I respect the hustle, love the videos, and think selling toys by teaching people to play with them is a great idea where everyone wins, but I don't judge the people who are bothered by the idea it's primarily an infomercial. Your mileage may vary.

In short, don't spend money on dominatrix time unless you just want to spend money on having that kind of experience. Do talk with each other and if you feel like it grab a few books and some pleasant-enough-feeling cheap rope and experiment. You can, and almost certainly will, buy more expensive and specialized stuff later, or just learn some techniques for safely manhandling each other that make rope unneeded if you get into that. Or all of the above. Mostly, just have fun and take care of each other and everything else will work out. Good luck and have fun.

(Disclaimer: links to commercial products and websites included for convenience only. I have no business relationship with anyone in this post other than happy customer and receive no compensation other than the warm fuzzy feeling of passing on recommendations that were given to me when I was starting. 1/4 inch nylon is fine and if you tie it in a pillowcase you can just chuck it straight into the washing machine and dryer. Fnord.)

What a good boy! That image of him bent over and inviting you to explore him for your own pleasure is priceless.

My recommendation would be that you continue to take things slow and stop focusing so much on the prostate. If you want him to have positive associations with these sessions, that can be done in any number of ways ranging from praise to sensual touching to rewards and aftercare specific to these sessions. Think of his prostate like your clitoris. Have you ever had a partner who simply would not stop poking and prodding it, all the while thinking this would totally rock your world? Our prostates are more subtle organs than our penises, and some of us don't like direct stimulation at all. I personally do enjoy sticking stuff up my butt on occasion, but when I tried stimulating my prostate with the njoy purewand that everyone swears by, I found it quite painful. As soon as the tip grazes my prostate, it causes my sphincter to constrict involuntarily, which in turn presses the tip hard against my prostate in a vicious cycle. I do enjoy indirect stimulation of my prostate when I play with my perenium, and I occasionally touch it lightly with my finger while exploring my hole, but the pleasure I get from inserting a dildo has little or nothing to do with prostate play.

Upon reflection, this should make a lot of sense. Perhaps you have sometimes enjoyed traditional intercourse even when your clitoris or g-spot was not directly stimulated. Some women enjoy anal sex despite the obvious lack of a prostate, and people of all genders may enjoy rimming, which has more to do with stimulating the sphincter than anything else.

There are many aspects of pegging your man might grow to enjoy. He already seems to enjoy submitting and trying his best to please you. And something about the physical sensations from that last session elicited that cute little moan. Beyond that there are feelings of vulnerability and intimacy. No one else has permission to explore his body in the way he is allowing you to do.

With regard to physical sensations, don't underestimate the sphincter. Lube up your finger, and, before or instead of penetrating him, pretend your finger is a tongue and you are rimming him. Make slow circles around his hole. Gently trace your finger down his spine and, just as you get to his hole, swerve a quarter inch to the left so you just miss it. Do the same thing again and swerve to the right. Do it again and just lightly dip your finger down into the valley for a microsecond (without penetrating), then keep tracing your finger over and past his hole and onto his perenium. Cup his balls. Every muscle in your body feels good when it stretches and relaxes. This is why yoga and massages feel so good. The sphincter is no exception, and it never gets a chance to relax.

Also, don't underestimate "feeling like he has to go to the bathroom." You know how sometimes after taking a massive dump you just feel so fantastic? Sometimes pooping can be painful, but sometimes things slide out easily and it feels kind of...good. It's more or less the same sensation when things slide in easily. This is actually the feeling I'm going for when I play with a dildo. After relaxing my sphincter and doing slow thrusts with frequent reapplications of lube until everything is nice and slippery and my body is (somewhat) used to the invader, I'll start pumping away at a pretty fast and (more importantly) steady pace until it feels like I'm just taking one glorious, continuous shit (sorry if that's TMI). As soon as you stop or vary the speed too much, the sphincter starts resisting again. This can also be pleasurable (hence anal beads) but is a decidedly different sensation. He actually should feel like he's pooping when he is sufficiently relaxed. Our bodies have no referent for relaxing to let something in. Our muscle memory only knows how to relax to let something out. Luckily, this same mechanism also makes it easier for you to stick something in. The obvious caveat here is that there's no way to enjoy this if he's actually worried about pooping on the bed. Invest in some water proof sheets or lay down plenty of old towels. And make sure he knows how to properly cleanse himself before these sessions.

Finally, you both may benefit from an approach informed by sensate focus. This link will initiate download of a 3-page PDF summarizing the practice. I am not a sex therapist, but I have read extensively on the subject, including the most up-to-date clinician's guide cover to cover. Stage 4 has some awesome gentle femdom implications, but I'd recommend focusing on Stage 1 for your current explorations. A common misconception during Stage 1 is that partners take turns touching each other for their own selfish pleasure, but they are actually supposed to take turns touching for self-focused interest and/or curiosity, without regard for their own or their partner's arousal or pleasure. Instead, both partners are supposed to focus on the most reliable aspects of touch perception: namely, temperature, pressure, and texture. It might be helpful to imagine that you're playing with Silly Putty, rather than your boyfriend's asshole, just to keep the focus on this sense perceptions. Meanwhile, whenever he gets distracted by concerns about pleasing you or enjoying himself, he should try to return his attention to clinical observations about his current sense perceptions of pressure, temperature, and texture. It might be helpful to imagine himself as Spock or an android explaining the sensations of pegging (silently) to himself without making any value judgments or showing particular emotions. The idea is to get both of you out of self-defeating "head spaces." Later on, you can start verbally communicating more about what does and does not feel good.

It might be helpful to think of your next few "scenes" as training sessions, rather than sexy times. Keep them short, and maybe leave the dildo and prostate massageer out of it at least for now. Keep it up just long enough to practice returning attention back to temperature, pressure, and texture, but not so long that either of you get tired or bored. Consider lying in the bed together afterwards, or watching TV. If you decide to continue having your normal sexy times and cuddles while these periodic training sessions are going on, consider saving it for a different time and place.

A good option to try initially is a knockoff Holy Trainer. I used one of these for a while and it worked quite well.

It's plastic and fairly closed design which is fairly good for comfort but will need to come off at least weekly for hygiene.

They usually come with 4 or 5 rings in different sizes so you can try and see which size works for you. This will come in handy if you want to go for a custom cage later as you'll have a better idea of the measurements that work.

And it's cheap, so if it doesn't work out, you haven't lost much.

Another important aspect is solid rings vs rings with hinges or multiple pieces. Solid rings are better for comfort and long term wearability. You have to put one ball through, then the other, then your penis, and it can take some practice. On the other hand, hinged or multi-part rings can be easier and quicker to get in and out of, but you might get pinched as there are places where your skin can get wedged into.

Speaking of getting into the cage, once the ring is on you, a really good way is the "stocking method" - you take a nylon stocking and put the closed toe end through the cage so you can pull it through the hole, then put your penis in the open end of the stocking and pull the stocking through as you push your penis into the cage. This helps pull you into the cage as far and completely as possible, minimizing friction and preventing skin from bunching up at the neck of the cage.

For sizing, you want the ring to have enough room to get a finger tip under it when it's on, not really more or less than that.

For the cage, I like as little room to grow as possible. Nice and snug around the shaft and nice and short, close to a perfect fit to the completely flaccid penis with as little room to grow as possible. Of course with a nice small cage comes a nice little humiliation angle as well.

And once it's all on, it's really useful to apply a little lube around the ring, especially at the bottom (most common place for "ring burn")

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:)

Search “sissy pouch panties”
Also, I love these and my boy started stealing them so I had to buy him his own. They are exceptionally comfortable

Here, try this instead: Razorless Shaving for Men by SoftSheen-Carson Magic Extra Strength Shaving Powder, For Coarse Textured Beards, Formulated for Black Men, Depilatory, Helps Stop Razor Bumps, Since 1901, 5 oz https://www.amazon.com/dp/B00CREUEV2/ref=cm_sw_r_cp_apa_i_lm4SDb0Q35MJT

Here is an example of what I was talking about yesterday: https://www.amazon.com/Under-Restraints-Ankle-Bondage-Fetish/dp/B00UZJK9KM

Also... how did last night go?! What kind of fun can you report back on :)?

This is my jam, and nearly the only casual pants I own.

Found it

This one:
https://www.amazon.com/FYJENNICC-Lightweight-Premium-Chastity-Transparent/dp/B07QWXGFHW/ref=mp_s_a_1_1?fap=1&keywords=fyjennicc+chastity&qid=1574810635&refinements=p_85%3A2470955011&rnid=2470954011&rps=1&s=hpc&sprefix=fyje&sr=1-1

Underwear Women 6 Pack Satin Panties Set Bikini from S to Plus Size (XL) https://www.amazon.com/dp/B076L2KMQZ/ref=cm_sw_r_cp_apa_i_RvRRCbH7SG3A4