Webinar Signup

Two Ways to Learn:

The Art of Pegging <<–

1. You are welcome to attend one of my free webinars. I schedule several each month, for all 3 classes (descriptions below). Click here

2. I now offer my Beginners Pegging class on-demand (others coming soon). This allows you to view it at your convenience, as many times you like, and share it with your partner(s) for a one-time fee. Click here

The Pleasures of Pegging – Beginners – 2 Hours

The misconceptions, myths and taboos that are all wrapped up in Pegging result in so much shame, and many misunderstandings. This can be tricky territory for couples to navigate. I will teach you what Pegging is, what it isn’t, and all the reasons to explore it. You will learn the necessary basics to start you off on your own Pegging adventure!

The Pleasures of Pegging – Equipment – 2 Hours

Choosing Pegging Equipment can be very confusing! So many toys from the cheap and toxic to top-of-the-line and pricey. Navigating all the choices can be mind-boggling. I will teach you how to choose the right equipment for you and where to find it! Big beautiful bodies need different equipment than small beautiful bodies. Sensitive prostates need different toys than prostates that need more stimulation. Also included, props and sex furniture for pegging! A very deep dive into equipment.

The Pleasures of Pegging – Advanced – 2 hours

Curious about the variety of ways to encourage orgasms for the giver and the receiver during pegging? Chasing after that elusive hands-free orgasm? I will share with you all the tips and tricks I know to help you experience the most pleasure possible while enjoying pegging with your partner. We will also explore the territory of the more extreme longer and wider toys, the safety concerns of same, along with the benefits of choosing to explore with them – and where to find these toys, too!

Where Can I Find a Woman to Peg Me? – 90 Minutes – Coming Soon!

This is the question I get asked pretty much endlessly, ever since I started teaching about pegging. In this webinar, I will teach you everything I know about finding a partner to explore pegging with. Personal stories of success, help with profiles, pictures, introductory messages, connecting with your kink community or connecting with a pro. No magic wand, but tons of good information. Takes effort, guys…and it’s so worth it!

Webinar Testimonials:

My Wife and I enjoyed your webinar today. Loads of great information and fun stories too. We both agree that the words from chat:  ‘Pegginar’ and ‘Ass Class’ were funny and appropriate. Your manner of teaching is wonderful as you put somewhat nervous men at ease with your calm and reassuring logic.  Your humor helps too! I hope you keep doing what you are doing. My wife and I are eager to get started on this new adventure. I can hardly wait until she is a comfortable and a skilled giver. I will do my best to help her all I am able. Cheers!


My girl friend and I attended your zoom meeting this morning. Really I wanted to say thank you for hosting the informative webinar. There were Societal stigmas that I thought I had addressed and realized that part of me didn’t fully let them go yet. It was very appropriate and a good reminder to start with those Common misconceptions . There was a lot of great detail information. You have inspired my girlfriend and I to explore pegging more fully than how we would have approached it on our own. We are very excited to enjoy the slow process of firsts. Thank you.


Hello Ma’am. I just got done with your advanced pegging webinar that a friend told me to attend, & she also recommended the one you do for beginners that I attended a couple of months ago, & am mostly writing about. I followed your recommendations on what beginner toy to get, went with the Aneros Helix Syn Trident & Sliquid Silk lube. I have nothing but positive things to say about both of those & I thank you so much for the recommendations. I’ve gotten better & better results from each night of using the Aneros toy, & I’m extremely happy exploring a side of me that I’ve always wanted to.

Someone that I’m in a dynamic with directed me your way & I’m glad she did. You’ve been extremely helpful & informative, along with encouraging. Hopefully sooner rather than later I’m finally able to get pegged & feel an entirely different sensation & have someone else be in control, which is nice. But main point is, thank you for your recommendations which have helped me get ready to be pegged, helped me enjoy something that I’ve always wanted to try but had no idea where to start, & you’ve technically also helped me be more comfortable with who I am, which is wonderful.

So again, thank you so much for the time & work that you’ve put into your webinars. They’ve greatly helped me so far & I will direct anyone possibly interested in pegging towards your site & webinars. Thank you so much Ma’am.


A huge amount of information. We got there thinking that we knew already most of what Ruby was going to teach. But how wrong were we!

Fantastic webinar, thanks Ruby 🙂


Just wanted to say thank you for this webinar. I learned so much, but not how to get to the chat block on an iPad. Thank you, thank you. I can’t wait to try some of those positions. We’ve been pegging for a couple of years but obviously just fumbling in the dark. Wow!


Webinar “Advanced Pegging” was just so educational today. 2.5 hours of harness advice, dildo types explained, anatomy, practical tips, pillows, furniture to help everything plus more! Your generosity in time and knowledge to help mainstream pegging for all is a worthy and noble cause. Thank You so much! PERFECT CLASS I would highly recommend to all.


Thank you for such a fantastic webinar on pegging for beginners. You covered a lot of material in such a relaxed and knowing way while empowering both givers and receivers with knowledge and acceptance. Beyond refreshing!!

I also would like to extend my gratitude for providing this information without a fee. I have noted the different ways to monetarily thank you for the time when I am better equipped to do so. I know flattery is cheap, but I’m the kind who only gives earned complements. That being said, thank you for reflecting the jewel in your name, and you are rare indeed. I’m richer for having crossed paths and I thank the universe for you.

I look forward to the next portion of the lesson.


I just got finished with your advanced webinar and I just wanted to say thank you so much for everything that you do (and for free nonetheless)! So much of what you covered are things that we’ve been researching ourselves and the information is so scattered. I have so many websites bookmarked with various pieces of information and your webinar consolidated so much of this information. I definitely think you should charge for these webinars.


This webinar was totally worth the price of admission. She is a tremendous presenter. She covered everything you’d expect and three times more. Highly recommended.


Ruby Ryder’s webinar’s are exquisitely wonderful.  She raises the bar, er dick, to new heights.  I don’t know where she learned to teach but her presentations are easy to follow, concise and engaging.  She is easy to talk with. Having been to many presentations myself hers was the best organized from start to finish.  If you have not taken her class, I’ll guarantee even veterans will glean a tip or two.  Cherrie D’Amour


I had to cut out a little early at the end of your online webinar this past Saturday but I just wanted to drop you a belated note to say thank you.  I wasn’t sure what exactly I was expecting, but your presentation was professional, educational, thorough and very well done.  I may decide to sign up for and watch it again in the future on a week-end when I’m not quite so busy so I can catch the whole thing and not have to rush out the door.  I was only vaguely curious about pegging prior to watching your webinar.  Now, I feel much more prepared to go down that path, if/when I decide to (I feel it’s only a matter of time since this kink is so prevalent among men).



Premiere 101 class, great guidance, absolutely accessible. Pegging Amazing!

Just doing the webinar itself was fun. I paid, cuz, I’m me. She’s got a Patreon, too. I’ve never taken a webinar nor really gone to Patreon to dig into it, but this presentation was worth me learning about those things.

And more.

Outstanding stuff! Can’t wait for the advanced class! Viva la Pegging!


Thank you for promoting another form of intimacy relatively unknown to experienced lovers.  I take the opportunities whenever available to expose more people to Ruby Ryder and PeggingParadise.com.


I so thoroughly enjoyed last nights webinar (until my laptop battery died a bit sooner than expected) and I wanted to give you a virtual round of applause! Thank you for allowing me to attend. 

Your tips and tricks have aided my girlfriend and I to have two of the most memorable evenings of our ~2 years together and I’m sure a third will happen soon enough.


Your webinar – Loved it! Learned a lot. Thank you. A real turn on with husband and me learning about it!


You have opened doors in a 23 year relationship I never thought existed.