Preparing for Prostate Massage, Strap-on Play, and Anal Play
I can remember it like it was yesterday- the first client I ever had came to me specifically because I advertised as a Chicago prostate massage escort who does strap-on play and prostate massage. I’d partaken in these activities many a time in my personal life as a top (the doer/giver of said activities), and I’d been blessed with bottoms (the receiver of said activity) who were experienced and really into it. The people I’d played with were so into these things, that they had their own prep routines, toys, preferred lubes, and puppy pads ready to go, and it made my experience as a top seamless. These folks had prepared so well, that there wasn’t any distraction from the situation at hand (heh heh).
My first-ever client though? Not so much. Not only was he ill-prepared in lots of departments (he definitely fibbed about his level of experience and to my dismay didn’t come with his favorite toys in tow or a very clean ass), and my lack of professional experience didn’t help matters for me or my bedding.
Now, almost seven years later, I’ve had my fingers, fists, and toys in more assholes than a combination urologist/proctologist, both personally and professionally. So who better to try and guide anal newbs, right?
I’ve broken this down into two sections- one section for the givers of said anal pleasures, and a section for the receivers. While there is different prep involved for both sides, I’d highly suggest reading both sections so you can build empathy and rapport with your butt buddy. Believe me; knowing what’s going on with your partner really makes the experience a whole lot better. So without further adieu:
Preparing for Prostate Massage, Strap-on Play, and Anal Play for Tops
Looking for info on preparing to receive prostate massage and anal play? Click here!
So, you’ve finally decided to get on board with the trend and offer anal play to your clients. Or perhaps you’ve been really curious about all the fuss and why people with prostates are falling over themselves looking for willing fingers to get into their asses. Maybe you’re just really turned on by penetrating your partner anally. Trust me; I get it. I really, really do. I’m a Chicago prostate massage escort. It’s hot to me.
I’m here to dispel some myths, prepare you for worst-case scenarios, and tell you things that will make you squick, cringe, laugh, and even turn you on. Because with prostate massage, strap-on play, and anal play in general, you’ll run the emotional gamut.
Before we even get to the play date, though, you’ll need to be prepared, both with your brain and in your supply closet. Here’s a list of basics that you’ll want around if you want to make anal play a thing you do ever:
Basic supplies for prostate massage, strap-on, and anal play
- Latex-free nitrile gloves. I buy them in black, on Amazon, in bulk. I keep them in a few different sizes at my incall location, and outside of condoms, they’re the one thing I’d never want to run out of.
- Condoms, both latex and latex-free. Toy coverage is important, particularly if you’re sharing toys. Plus condoms can really help to contain any unexpected messes.
- Puppy pads/Chux/Absorbent bed pads. These will save any surface your bottom is laying/kneeling/hovering above, and are just as important for catching excess lube and tossing used toys onto as they are for catching any ass leakage.
- Lube, both water-based and silicone-based. I love Sliquid for water-based and hybrid lubes, and love Gun Oil for silicone-based. Oil-based lubes, Crisco, coconut oil, Boy Butter, and the like are best saved for large insertions, anal stretching, and fisting. Give your bottom options for their lube experience! Just remember your lube compatibilities (no oil-based with latex, use caution with silicone toys and silicone lube, etc).
The above things are really all you need, outside of your hands, to have a fucking rad prostate massage or anal insertion experience. Most of the prostate massages I give are done solely with my hands, with toys used when folks are ready to take more. If you’re anticipating playing with folks who are going to be interested in more than just your hands, or your hands are small (mine are… big, so I get away with less toy use for prostate/anal play), you’ll want to have these things on hand as well:
More advanced supplies and toys for prostate massage, strap-on, and anal play
- Dildos of varying sizes, starting quite small in size. I personally prefer Tantus brand dildos for work purposes; they’re really great quality silicone, can be easily sanitized, and they’re durable AF. I’ve had several of their toys for well over four years and there’s little to no deterioration on them. I’m also one of those people who uses silicone lube with silicone toys (most pre-lubed condoms have silicone in the lube), and that’s been a non-issue. Also note, that all of those mega monster dildo cocks that you see in porn aren’t actually used a lot IRL. I have a few of them, and they’re truly more for intimidation/humiliation purposes and don’t serve much of a role outside of that unless I have a really greedy/hungry bottom who can actually take them.
A WORD ON INSERTABLES: Please, for the love of your body and the safety of your play partner, don’t buy cheap toys that smell like new carpet and gasoline when you take them out of the package. “Jelly” toys are full of carcinogenic agents, and anal tissue is highly vascular and super absorbent. Large dildos are often made from materials that are less than ideal to keep them affordable, and they may be so big that they can’t be covered with condoms. If your partner is interested in these, I suggest that your partner have THEIR OWN, and that these not be shared between people. The smell of these toys is often nauseating and can give folks headaches, too. High-quality insertables are not cheap, and you should only be using toys that are non-porous and can be easily sanitized/sterilized. Toys made with high-quality silicone, stainless steel, and glass are the only toys that enter me or my play partners.
- Prostate specific toys. Whoo, these vary wildly too, and will ultimately depend on the comfort and level of intensity your bottom is looking for. My absolute go-to in this category is the Njoy Pure Wand. It’s solid stainless steel and weighs something like 2-3 lbs and can double as a weapon, but it’s prevented me from developing carpal tunnel. While there are lots of other toys like it on the market, the quality and durability of the Pure Wand is unsurpassed.Another prostate go-to that most people will find when looking for prostate toys is the Aneros. I personally have zero experience with this toy, as anyone who’s come to me and said they bought one used it a few times and decided they didn’t like it. Your experience may differ though!
- A strap-on harness. These vary wildly in style, support, comfort level, and price. I personally prefer SpareParts harnesses, as they’re washable, comfortable, and really supportive. I highly recommend trying on harnesses when possible, and if you have a Pleasure Chest, Babeland, or awesome local toy store, you should be able to try them on with no worry.
- Butt plugs of varying sizes. I honestly don’t use these a whole whole lot in prostate massage/strap-on scenarios, but they’re great to have around in case someone needs some loosening up. I find the firmer the plug, the better, and if it’s angled to do prostate stimulation, great!
- Poppers. Yep, I said it. If you really want to get into anal play and offer your play partners an experience that they’ll definitely not forget, you’ll want to keep poppers on hand. Of course, you can always have your bottom bring their own, but I’ve turned many a person onto poppers to enhance prostate massage, strap-on, and anal play experiences and it’s changed their whole world.
Communication with your bottom/client
Now that we’ve gotten through a supply list, we really need to go over communication with your bottom. If it’s your first time administering a prostate massage or any form of anal play, let them know! Doing something for the first time isn’t shameful, and you don’t have to be an expert in order to do it. What you do need to do though, is be up front about your level of experience, or inexperience, as may be.
You’ll also need to address your bottom’s /client’s level of experience as well. Jokes abound when it comes to the truthfulness regarding a bottom’s experience (I’ve had folks tell me they’ve never had anything in their ass and then proceed to take almost half my hand), but getting an idea of where you’ll want to start is important. It’ll inform your toy selection, positioning, and length of time you’ll need for the session. For inexperienced players, I definitely recommend a longer period of time, ninety minutes minimum, and starting out with your client on their back. It’s a position that’s easy to relax into.
Cleanliness is next to godliness: How to tell a grown ass person to clean their ass out.
Okay! So you’ve got some basic toys, all the gloves you could want, and you’ve ditched your white comforter and thrown down the puppy pad. They’ve arrived, you’ve talked a bit, and you’re excited and ready to go. So are they! Time for your client to put their heels to Jesus, right?
NAH. Stop right there.
You’ve wrongly assumed that your client is prepped the way they should be, and you’re about to be in for a shock. Here’s why:
In this scenario, your client is probably a cisgendered, heterosexually-identified man who’s never truly thought about the cleanliness of his asshole. He may have never even considered scrubbing and washing it thoroughly, let alone cleaning inside of it. He might even be one of those guys who thinks grooming and taking care of one’s appearance isn’t “manly” and might even have some programming around ass play being identified with gayness. Or, he could just be wildly unaware of his own asshole!
While lots of men do take this into consideration, a lot of cis hetero-identified men do not.
Remember the first-ever client that I saw? I assumed very incorrectly that he knew how to prep correctly and was left to deal with all kinds of shitty mess. I was under the assumption that a grown-ass man knew how to handle his own body and asshole. I was wrong. So very, very wrong.
Before your bottom even gets to you, send them this as a homework assignment. Quiz them on it, too:
HOW TO CLEAN YOUR ASS FOR ANAL SEX
It’s a really great cartoon on how to clean your ass for anal sex, and is super applicable to any sort of anal play. Have them pay particular attention to that part about going past the sigmoid colon, lest you’d like to get the front of yourself covered in ass water. Not that I’d know anything about that or anything, or why I have a latex apron. Anyway!
In our particular situation, I’d anticipate your client needing time to prep at your space. Make sure to let them know that they’ll need to bring their own enema bulb/supplies, and that the time will be included as part of the session. You’ll be amazed how many folks come prepared once you tell them prep time is on-the-clock. 😉
Also of note: if you’re going to supply Fleet enemas, or your client is going to pick one up, make sure you don’t use the liquid that comes with it! It’s a laxative, and we’re only looking to clean out a portion of the colon. Dump the contents and fill it with warm water instead.
Even if your client is prepped, I’d suggest having them hop in the shower or thoroughly clean up/wash prior to getting started. Precautionary measures, after-all.
A word on hemorrhoids and anal fissures: if your client has hemorrhoids and they are currently inflamed or an anal fissure, do not pass go and do not collect $200. Anal play is only going to make the situation worse. Hemorrhoids themselves don’t have to mean no anal play, and here’s some tips for getting around that situation. Anal fissures are notoriously tough to heal, and need to be left alone. If your client currently has an anal fissure or tear, ass play is absolutely a no-go.
You can learn more about anal fissures here.
Hey, Erin! Is there anything tops can do, hygiene-wise, to prep for giving a prostate massage, anal play, or strap-on play?
I’m really so glad you asked! Honestly, outside of your regular routine, there’s really only one major thing you should do before going near someone’s asshole with your fingers: take care of your hands!
Whether that entails getting a manicure or trimming your nails/hangnails on your own, make sure your hands are something you’d want near your own delicate places. You’ll be wearing gloves, so a lot can be forgiven, but just do a quick check and make sure you don’t have any broken nails or anything jagged that could be felt through a glove. If you’re femme and have cute-ass stiletto or coffin nails, make sure to stuff cotton balls into the fingertips of your gloves. Trust me, I’ve accidentally poked a prostate with a stiletto nail because I forgot to do this. It’s a faux-pas that can be hard to come back from and leave your client really uncomfortable.
The Main Event!
Now that your client/butt buddy is well-prepped and ready to go, it’s time to start the action! Lay that puppy pad down, have your supplies ready and easily accessible, and get down to it!
**Because this is an article pertaining to the basics of anal play in general, there’s not specific technique for prostate play mentioned. That’s going to be in a follow-up article!**
If it’s your client’s first time (hell, if you’re ever going to be in someone’s ass, period), they need to be turned on. You can’t just lube up and jam your fingers/a dildo into someone’s asshole. This is a one-way ticket to anal fissure town, and that’s not the kind of impression you want to leave. Chances are your client is going to be nervous, and you’ll need to help them relax in order to make this a pleasant experience for the both of you.
When it comes to getting a client turned on and not quite so nervous, I’m a big fan of massage and hand jobs, and if I’m feeling flexible enough, I’ll include oral. Paying attention to your client’s body cues, breathing, and erection will let you know when they’re ready, but definitely feel free to mix it up. You have your own methods as to how you turn a nervous client into a turned on one, and this really should be integrated into what could be considered the “warm-up phase” of your anal adventure.
It does not matter if your client booked a prostate massage, a strap-on session, or some other anally-focused experience; their asshole needs to be warmed up and prepared to take whatever you’re going to put in it. Use lots of lube, more lube, and go slowly! Remember asking about their level of experience? This is where that information comes in really handy. Newbs will need a lot more warm-up time. Folks experienced with anal play may need less. You’ll know when your client is ready for more; you’ll feel their asshole relax and become more pliable, their body will relax and cues will become apparent. When in doubt, ask! I talk to my clients A LOT during anal experiences; from making sure I’m in the right spot for prostate play to permission to insert a bigger toy for anal stretching, communication is key (even if it is along the lines of ‘is that greedy hole ready for more?’).
Also, don’t concentrate solely on your client’s ass; pay attention to their dick, balls, perineum, and general genital area. It all feels amazing and will add to their pleasure exponentially! While the experience is anally focused, it doesn’t mean all the pleasure is all anally focused; folks who are new to receiving anal play will often need more genital stimulation than those who have learned to harness their anal feelings and use them for pleasure.
I should note here something really important when it comes to anal play of any sort: your client’s dick may or may not stay hard the entire time, and chances are it will cycle through periods of being hard and being limp. This does not mean your client isn’t turned on; chances are they are super into what you’re doing. If your client starts to worry about their dick not being hard, remind them that ultimately as long as what you’re doing feels great, the hardness of their dick doesn’t matter. When in doubt, share this snippet of info with them:
The same pelvic floor muscles that contract in order to keep a dick hard are also the same muscles that need to relax in order for an asshole to open up.
OH NO! MY CLIENT HATES THIS OMG IM BAD AT THIS WHYYYYY
First off, don’t freak. This isn’t entirely a reflection on you and chances are it’s not a reflection on you at all.
You’ve done all the right things, communicated, and your client is just not into it and not having the experience they’d hoped for. That’s okay! Everyone’s body reacts differently to new stimuli, and I’ve had a few clients over the years really dislike or not get into prostate massage and anal play at all. Unfortunately, prostate massage and anal play has gained a reputation as being a Holy Grail™ sexual experience that makes everyone feel incredible and for some people this just isn’t true. If your client is one of those folks, and you can simply drop the activity and move onto something else that you’ll both be happy with.
I tell this story to clients whenever they’re disappointed that anal play wasn’t what they thought it would be:
The first time I ever had g-spot stimulation, I was NOT into it, in the least. I didn’t like it, my body tensed up, and I couldn’t relax. It was a new sensation that neither my brain nor my body knew how to process, and I asked for the experience to end pretty quickly. I was curious though, and with time and patience, came to understand the wonder that is that particular area of my body. Prostate stimulation isn’t much different in that sense, and can often take the body and brain some time to process.
Also, keep in mind that the more experience you gain in this area as practitioner, the more likely you’ll be to give your client a stellar experience. Your client should be understanding and empathetic towards you as someone who’s new at giving!
Cumming To an End: The Old Faithful Experience
You’ve gotten in there, and you’ve worked your magic through a series of fingers, toys, oral, dick massage, and the like. Your client is now on the brink of orgasm! Fucking awesome! How, where, and when your client orgasms is entirely up to the two of you, but here are some things you should expect.
Cum volume/viscosity will be wildly different from what you’re used to. Oftentimes, cum will be much more watery, and there will be a lot more of it. When the prostate is stimulated, it produces more seminal fluid. On top of that, an orgasm that includes anal play is often far more intense and longer-lasting than that of an orgasm produced simply through genital stimulation.
If everything goes right, your client might just be in for the most intense orgasm they’ve ever had, and that’s probably why they’re searching out this experience in the first place.
Your post-orgasm client is probably in a play-doh-like pile and unable to do much except lie there. The one thing they might be able to do, however, is tell you to get whatever’s in their asshole out of there ASAP. While your first inclination might be to just snatch out your hand or the toy, you’ll want to go slow. The sensation of having something removed from your ass can be just as intense as something going in. The directional movement out of the ass is also the way nature likes things to move, so your client’s body can also help with this.
Keep in mind though, that no matter how well your client prepped, all that moving and shaking may have caused some things to come loose. On occasion, some fecal matter will come out with your fingers/toys. No big deal, really. You signed up for ass-play after all. If it’s on your glove, take the glove off from the bottom up and ensure the glove turns inside-out; same goes for the condom that’s on the toy- let it roll over itself and turn inside-out to allow for easier clean-up.
Also, keep any comments about minimal post-play mess to yourself. It’s an ass. There’s bound to be some kind of mess at one point or another. However if the mess is extreme, you might want to recommend better prep for your client in the future. If there’s no mess and you’re thoroughly impressed, let your client know! It encourages them to keep up that prep routine for future playtime with you and others.
Keep the puppy pad/towel under your client until they’re ready to get up and clean themselves up. They’ll probably want a shower due to the copious amounts of lube you’ve used during the experience.
And Scene! Fin. The End. You did it!
You had your first anal experience and if all went well, you squicked, squeed, laughed, and enjoyed your whole way through it, and so did your client. If you want to find out what went well and what could have been better, ask your client and don’t take things personally. This is a very new skill you’re learning, and having feedback is important if you want to get really good at it! Of course, you might have just hated it and in that case, now you know. You shouldn’t feel obligated to continue on this path unless you truly want to. No shame in trying and deciding something isn’t for you.
If you’d like more information, I’d recommend reading the entry below that’s geared towards bottoms. The more knowledge the better, right? I’m also working on a series that addresses specific activities, so for all of you looking for a prostate massage how-to, you’re in luck!
I’m hoping you found this article helpful, and I’m opening up the comments to take questions. I’ll answer them when I can!
Until then, remember that spelunking isn’t just for caves.
xoxo
Erin
PS: remember, the article for how to receive anal for bottoms is here!
