✨ Prostate Massage & Pegging ✨

Luna Robbie
Sep 5
9 min read

I take extreme pleasure in administering pleasures for fellow buttsluts and curious potential converts alike.

Pressure to do butt stuff is never sexy; however for anyone who is curious or craving an anally excited playmate and wants to embark upon a next-level luxury experience of pleasure, I love to frolic in the land of assplorations.

So let’s dive—er, gently massage—our way in!

tl;dr:

The basics of butt play:
- Lube is a must
- Prep is simple
- Every step is guided by open two-way communication
Sessions can range from gentle first-time intros to wild strap-on adventures.
We mix erotic play with safety, trust, and exploration
Prostate play and pegging require a level of erotic trust and surrender to pleasure that can dismantle shame, deepen a sense of safety in intimacy, make the receiver a better lover, and unlock the possibility of assgasms.

🎧🎙️ Listen to me to a Prostate & Pegging episode with Kathy Kay of Strictly Anonymous Confessions on Apple, Spotify, or wherever you get your podcasts.

MY DEFINITION:

Prostate Massage

The prostate gland is a walnut-sized organ located just below the bladder in people with penises. Its primary biological role is to produce seminal fluid, and when stimulated internally through the anus—or externally through the perineum—it can create sensations ranging from gentle arousal to overwhelming orgasm.

Pegging

Dan Savage popularized the word, which refers to using a strap-on harness with a dildo to penetrate a partner anally.

WHY I LOVE IT:

I have a two-way arousal system when it comes to putting things in holes.

I discovered this in my early twenties when a lover invited me to explore putting a finger first on and then in his anus (always use lube!) while he was in pussy penetration mode. I was already having an extremely nice time, but this skyrocketed my turn-on to previously unknown heights—we were like a double ouroboros, a transcendent symbol of infinite time and human connection and we could still make out.

It would take me another half decade of dabbling with fellow unschooled ass-curious lovers before I found an anal mentor who taught me the wonders of giving and receiving slow warm-up, massage, training with plugs, and that lube is non-negotiable for butts (unlike pussies, butts don’t produce their own lubrication).

As a receiver, it took me nine months of buttsploration in a supportive kink dynamic to fully let go of the unconscious anal shame I hadn’t known I was carrying so I could have my first assgasm.

As a giver, a huge part of the turn-on is confidently creating a safe, delicious space for my partner to rest, receive, and explore the sensations of deep pleasure—without any hint of pressure to perform.

In fact, I need my counterpart to relax. At most, I might want a partner to perch on all fours if facing down (oh yes, I have dreams of subtle-and-beautiful-but-utilitarian bedroom furniture), sometimes legs up if face up. And I will require a small bit of verbal feedback about the sensations my partner is experiencing while we calibrate.

Plus, I find it so fun and hot to feel my lady parts get increasingly wet while my hands are getting most of the action.

While there’s no definitive research yet showing prostate massage prevents prostate cancer, some studies suggest it may improve circulation, relieve congestion, and help people notice prostate-related changes sooner. And since increased blood flow is almost always a good thing for health and pleasure, it certainly can’t hurt—unless you skip the lube (Always use lube! No one wants anal fissures or even micro-tears).

Finally: I can definitively say, every penis owner who has offered up their asshole to me has absolutely become a better lover to my pussy with their hands, mouth and cock.

DETAILS AND PREPARATION AND VARIATIONS:

There are many different ways to play with butts, and it’s important to tailor each session to the needs of the person receiving.

A session with someone who has been warming up their own butt for years while watching my content is going to feel very different from someone who knows nothing of my own buttslut story and is overcoming shame-y social conditioning along with the new feeling of exploring sphincters. And, both can be deliciously rewarding as long as communication lines are open.

At the ranch, we explicitly spell out what explorations are on the agenda, and I encourage this approach for all assplorers. In the initial negotiation, we decide which activities we definitely want, which activities we want to explore with moment-to-moment communication, and anything we definitely want to stay away from.

For some people, any type of ass-related play would be considered “kinky.” For some of us, buttholes are inherently sensual and many wonderfully lovely vanilla anal sessions have been had. Pegging can definitely include a power dynamic—but it does not have to. However if the idea turns you on, I recommend trying it.

Throughout the session, I ask partners for verbal feedback about their experiences, give them different pressure options and finger motions to choose from, and I love telling them what I’m doing to them and what I’m about to do next. Especially with new-to-me or new-to-butt-stuff partners, I make sure to ask them each step of the way if they want to go on to the next agreed-upon step, stay where we are, or go back to something else.

This sets the stage for affirmative communication as we collaborate in the exploration of possible assgasm. But once activities are agreed-upon:

How does butt play actually unfold?

For me, all sessions start with body massage—the extent of which will vary, vastly based on need. But before we get to specifics, the most common questions I get for assplay-related sessions are always about:

Preparation

It is important to know thy self, and know thy partner since comfort thresholds vary from person to person.

I’ve noticed that those who engage in regular anal play seem to have a good sense of their body’s rhythms, and also aren’t terribly bothered if bits of fecal matter are present—it is normal, given the location. A healthy diet of whole foods and plenty of fiber supports regular bowel movements, after which there is typically a clear window for play.

In Nina Hartley’s Guide to Total Sex, she points out that really, it’s just about cleaning a few inches of the skin that lines the rectal canal, which can be accomplished with water in a lube gun or enema bulb.

I’ve also heard stories of fasting or high-fiber or veggie-only diets leading up to play; I don’t enjoy being hungry and typically live a life with great fiber levels, so I don’t typically prep much myself if I am in the role of receiver.

However, I have heard horror stories related to various new, heavy, spicy, and/or processed foods that caused unexpected situations so…know thy self, always hydrate, and play with a partner you can be comfortable with, regardless of what unfolds.

I also have a nurturing kink, so if you’re nervous and want to be walked through the cleaning/enema process, as long as you bring that up in the negotiation, we can work that into our playtime. Typically most of my partners make the effort to clean up ahead of seeing me so we can spend more of our time together on play.

Brand New Initiates

Sometimes, explorers need a safe and helping hand to cross new territory. Especially if anal play has been demonized, considered taboo, or labeled shameful in one’s household or community of origin, a helpful hand and reassurance might be just the thing.

Ideally, I would get to say hello to the entire animal body, massage every inch so it can relax, and transition slowly towards erotic massage, really taking my time waking everything up head to fingertip to torso to hips, then toe to thigh, finding the locked spots in legs and pelvises, and spending so much time rubbing near and around the anus, it’s basically begging for my touch by the time I get there.

Explorers

For the curious ones who have shirked social norms (at least privately) on their own, sometimes all that’s missing is a co-creator. These playmates will often show up, favorite toys in hand, usually already wearing a butt plug, and in some cases of very good listeners, have read all my preparation manuals and have already been edging a week for me.

They are typically exceedingly eager for me to touch all their hot-button spots, which makes them all the more delightful to draw into extended tease. I do still usually wake up a body, but if the animal body already feels anal-safe, I might spend more of my warm-up tease focusing on and around their pelvis, perineum, thighs and buttocks.

Add Cock

How much I include a partner’s penis will vary, person to person.

If someone is brand new, it might be helpful to receive a familiar pleasure sensation to relieve the pressure of experiencing a new, unfamiliar receiving. For others, this is entirely overstimulating in a non-delightful way, so instead we focus on the single sensation and communicating with me as we move slowly, letting go of all penis worries. In many cases I might include a mixture depending on how the arousal cycle unfolds, which is why ongoing communication at each step of the pleasure experiment is so important.

Fingers and Toys

I always start with my hands, arms and elbows for the massage. When the time is right, I don my black nitrile gloves (who else has at least a hint of medical kink?) and continue the massage internally with a finger. This is where we get to dial in communication about the sensations being experienced as we progress.

I listen to my partner’s body and follow its lead, and wait to be welcomed in (never force anything into another human being). Sometimes one finger becomes two (or a few!), but sometimes even a little of rimming massage is enough to sate the curiosity of a novice explorer.

Fisting is typically beyond the scope of this session, but could be included if negotiated ahead of time and appropriate training were in place.

Depending on the desires laid out before play, we may add toys—anal dilators, beads, butt plugs, vibrators and dildos, and I can spend quite a long time getting lost in experimenting with a partner to find out what they like best. If in a kink context, sometimes it is fun to plug a submissive before administering pain and/or pleasure or commanding worship.

And speaking of worship—

Add My Mouth

I have exploded some heads adding fellatio while two fingers administer prostate massage and my other hand anchors the cock and tickles the balls. I am told it is a phenomenally delicious series of sensory delights (again using communication to discover favorites), and that it is nourishing to be able to relax so deeply in a safe space.

If it’s a session that includes rimming, I will use a dental dam and/or Lorals, depending on what’s happening in a given moment. For those of us who want to lick in all the nooks and crannies of our lovers, Lorals are natural rubber latex panties invented to add a layer of safety. They’re nice and thin so interesting sensations can be delivered everywhere, back to front and back again, and I personally like the containment of a nice bulge.

Add My Strap

For those who wish to experience my pegging skills, I will add a cock to my strap-on harness once everything is warmed up. I do usually pack a couple of dildo options, however if you have one that is a favorite, I encourage you to bring it along. Doggy is a classic favorite, but positions are ours to explore!

Assgasm Potential

Anal orgasms are not guaranteed, however they seem to happen with my lovers who are the most comfortable, and even first-time explorers have had an assgasm of their desires. I’ve noticed that those struggling either with stigma or who take more time to feel comfortable with the intensity of the sensation have a harder time surrendering. However, I’ve seen curiosity, trust-building, and practice lead to magically pleasurable places!

Aftercare

Even if there isn’t an explicit kink dynamic, it is a powerful experience to surrender deeply, and I require a reconnection and reintegration period to close the session—part of the reason anal play sessions are in the luxury category is because in most cases it’s hard to rush them.

What this looks like will again vary from person to person. Usually it involves at least a little bit of quiet cuddling. Sometimes we eat snacks and share recaps. Sometimes I pet or brush their hair while telling them the specifics of the good job they did, and the parts I found especially arousing. Sometimes it’s a conversation in the shower together about shame, society and what it feels like to realize we can enjoy what we enjoy. I encourage check-ins after the fact, especially if raw feelings arise in the wake of big vulnerability. If societal shame rears its gnarly head, I’m there to reaffirm the greatness of my partner’s butthole.

WHO IT’S FOR:

Anyone who wants to have their butt played with by someone who is definitely into it.
Any penis owners who wants to let go of worrying about hardness and enjoy receiving.
Anyone who is curious and wants an experimentation friend.

Does it make a guy gay? Nope—however in my experience it can make him better at giving oral if he’s paying attention.

So, if you’ve been looking for a luxury experience reaching the heights of anal pleasure with a partner who will make you feel safe—and all kinds of other things—this session might be for you.