I do a lot of pegging—that is, strap-on sex with male partners. Most of these partners are fairly, if not totally, new to anal play and prostate stimulation, let alone the added psychological experience of being “fucked” by a woman. It can be a daunting endeavor, and my clients (I do this professionally) are often nervous about several aspects of the activity.
I am totally self-taught, led by my experiences with sex work in general and a love and history of fanatical sex toy enthusiasm. I have always been very open-minded, and when I chose to embark on a sex work journey for a second time, I decided to avoid past mistakes and stick with activities that didn’t wear out my body or cross my boundaries. The term “open-minded” seems to lead a large portion of prospective clients to the idea of strap-on sex. With an arsenal of sex toy review items at my disposal, I was all for it. Heck, what better way to produce a great review than with multiple partners to test the merchandise?
After working with a few regulars, accompanying clients on journeys with orientation exploration, and introducing several gentlemen to the activity, I started to feel like a pro. But hold on! Here I am offering to help people discover their prostates, and not only do I not have one, but I don’t even enjoy things inside my butt? Okay, the only respectable way to make sure that experience qualified me to teach and practice pegging was to make sure that the available literary materials matched my technique. I was quite confident that I was doing everything right with nothing but very satisfied bottoms, but it was best to make sure.
I contacted every toy reviewer’s favorite LGBTQ publisher, Cleis Press, and asked what they had available. This is how I acquired The Ultimate Guide to Prostate Pleasure by Charlie Glickman—it sounded perfect! My copy is softcover with an attractive photo of a toned, muscular dude’s back, inviting you in. The 346-page, large-print book is divided into 15 chapters which follow a short foreword and introduction.
Chapter 1: Before We Start (FAQ): All sorts of questions that I myself have heard over and over are addressed in simple, easy-to-understand, extremely sex-positive language. Questions about pain and whether it’s messy accompany the popular “will it make me gay?” (Of course not—gay means men attracted to men, nothing at all about the inside of his butt being rubbed by a woman with a toy) and talk about where exactly the organ itself is located and accessed.
Chapter 2: The Sexy Prostate and Chapter 3: What Is the Prostate?: All about the specifics of anatomy and what to expect. Several quotes are included from the real experiences of various men describing how p-spot stimulation feels to them, and comparisons are made between the female g-spot and the p-spot. There’s a short excerpt on prostate stimulation for transwomen that I found informative and important to include as transwomen’s bodies have similarities and differences with p-spot stimulation that are probably not addressed in many other books on anal play.
In Chapter 4, hygiene, cleaning, and hair removal are covered—this makes prostate stimulation less messy and much easier to navigate.
Chapter 5: Penetration, Chapter 6: Searching for the Magic Button, and Chapter 7: Locating the Gland: These three chapters pretty much say to go slow, breathe a lot, he’s in charge, and stop when it hurts, along with some suggested positions. They also remind you not to forget about his penis during all of this.
Chapter 8 is a chapter I find most relevant to whom I assume will buy this book, at least based on how often I’ve been asked how one partner can broach the subject with their significant other. I have a ton of clients who say, “I really wanna try this but I’m afraid that if I tell my wife that I want to stick something up my butt she’ll kick me out.” They want to (a) make sure that they enjoy it before attempting to introduce it, and (b) know what they are doing before they make the request to avoid clumsy mishaps.
This leads to Chapter 9: Prostate Massage and Chapter 10: …Massaging the Perineum, which focus on technique for massage, both internally and externally. Chapter 9 has some great tips on combining p-spot massage with penis play, which is useful info since it can be confusing to lose an erection during intense pleasurable stimulation. Anal fisting is also covered, which I found interesting.
Chapter 11 covers my favorite TOYS! Starting with thorough info on types of lube, then moving through explanations of all the different toys for anal and specifically prostate use, including special brand names. They go on to cover harness types and strapless strap-ons, finishing with the kinky stuff—electrostimulation and urethral sounds. Every good toy manual should always contain proper material and cleaning info. I find here it is brief—I would like more info on how to choose a material other than just impermeability.
Chapter 12: Anal Sex and Strap-On Fucking: The juicy stuff—more technique and positions. Rather repetitive of previous chapters until you get to the sling stuff. I especially like the advice on where to put his legs because often my partners seem self-conscious of this, not wanting to do the “diaper position.” Pegging tips, including how to help the top get off, round out the chapter.
Chapter 13: Real Men Don’t…: Didn’t we already cover this in the first chapter? Oh well, I’m sure many men are going to need a lot of reassurance that taking it up the butt does not make them weak or gay. Real men take it up the butt, dammit!
Chapter 14: Prostate Health: This chapter is all about the medical issues that can affect the prostate, with a major focus on cancer from screening to treatment.
Chapter 15: Possible Benefits of Prostate Massage: Including increased circulation, clearing blockages, and breaking up stones, to name a few. The chapter then goes on to explore the history of prostate massage and how it has continued to be recognized as a valid holistic health treatment, at times rivaling modern medical methods and maybe even preventing prostate cancer.
CONCLUSION and AFTERWORD: Massage that prostate and recommend this book—this author is rad. That’s basically the gist of it. The resources/endnotes/author bio and index finish the book.
Reading this book from an intellectual perspective, I would be a bit bored and feel patronized from all the repetition, but I’m sort of biased since most of the content I already had experience with or knowledge of. Therefore, I revert to thinking about all of the questions that my prostate stimulation clients are full of and the various concerns they express. Would this book cover all that they need to know or would find helpful? Yes, and then some. Many topics addressed are direct issues brought up time and time again by average dudes lost as to where to find what they need to know.
Our society in general still sees anal sex as taboo, promoting it regardless of whether women are the receivers but shunning it in relation to men. This doesn’t make a whole lot of sense, seeing as how the P-spot, the most sexually pleasurable bundle of nerves on the male body, is accessible anally, while in contrast, females have no such anal spot. In other words, the male anatomy is much more designed for anal penetration/stimulation than the female. There are just as many bisexual men as women, but once again our world promotes female bisexuality as “hot” and normal while male bisexuality is seen as disgusting and strange.
The Ultimate Guide to Prostate Pleasure makes it clear to readers what I am in 100% agreement of—that anal sex, prostate, and strap-on play are not solely gay or bi/pansexual acts. I think fear of threatened identity regarding sexual orientation and female/male status is rampant and hinders more common prostate play. One area that the book does not cover is the psychological submissive factor of being a bottom during anal play, other than in relation to gender and orientation. Not all gay male bottoms are submissive, and neither are any other men by any label, but pegging is a great way to explore status. Submission is intensified with certain positions like being on all fours. Strap-on play is a physical activity but also can play a major psychological/emotional role.
Thank you to Cleis Press for providing me with a copy of Charlie Glickman’s book in exchange for my unbiased opinion, making for a review in accordance with all relevant legal guidelines. Cleis Press rocks, and for once, I will actually suggest Amazon as the best place to pick up a copy. Click on the link below after clearing your cookies, and the mega-giant will actually award me a small commission, which will ensure that I keep making videos and writing reviews. Thanks!
Check out what else Cleis Press has to offer in the fields of sexuality and/or LGBTQ literature. They are a groundbreaking, truly sex-positive publishing house. I will be giving away a copy of The Ultimate Guide to Prostate Pleasure with a few other pegging-related prizes in an upcoming post on beginners’ pegging. Subscribe to my latest posts by email or comment below, and I will contact you when the giveaway goes live.