You’ve finally decided to take the plunge and are ready to explore all the pleasure that comes with prostate massage, strap-on play, and other forms of anal play. Being the smart and savvy person you are, you’ve looked up ways to best prepare for your first encounter with a pro. Thank goodness for that because I have a wealth of knowledge about all things anal.
Let me help debunk some myths, prepare you for worst-case scenarios, and give you advice that might sound awkward, make you laugh, or even turn you on. Before arriving at your top’s space though, it’s important that you mentally and physically prepare for strap-on sex or other kinds of anal play – be it prostate massage, toy play, anal training, or fisting.
You’re Not Gay, But Anal Play Sure Is: A Lie in Three Parts.
It doesn’t matter whether you identify as gay, straight, gender non-conforming, or non-binary– anyone can enjoy anal play! Straight and queer folks can both like it, or dislike it; either way, enjoying anal play has nothing to do with your sexual orientation. Also, stop thinking of toys like butt plugs, dildos, strap-ons and poppers as ‘gay’. While they may be closely linked to gay culture, using them doesn’t make you gay; it makes you a user of that toy or enhancement.
Free yourself of the idea that anal is only for certain people–open your mind and your body will follow!
How To Find a Strap-on Escort or Strap-on Mistress
When I began offering anal play, prostate massage, and strap-on play as an escort, it was something that not many were doing. In the past, if you wanted an anally focused experience you had to give up the intimacy and see a professional dominatrix or choose to skip the kink and hire an escort. But those days are long gone! Many providers specialize in BDSM, kink, fetishes, prostate massages, strap-on play, and anal play.
Professional dommes offer a more limited experience with boundaries regarding what can and cannot be done with them, generally relating to intimate contact, nudity, and types of touching.
Fetish providers or specialized escorts usually provide a more comprehensive, sensually-focused experience. So make sure to read plenty of websites and identify whose style is right for you! Both professional dommes and fetish providers/specialized escorts have their place in the world of anal play – it all depends on what kind of experience you’re looking for!
When communicating with your chosen provider, make sure to pay attention to their etiquette. Most escorts are very specific that lewd/sexually-oriented communication is not allowed. Some will allow discussion once you’ve been screened. Professional dommes often have surveys and will want to know quite a bit about your interests and experience.
Take some time to read through your chosen provider’s website – it may provide hints as to how to discuss your interests, and if that provider offers what you’re looking for. Some escorts may charge extra for special services such as prostate massage, strap-on play, or anal play and list it in their profile. Additionally, a domme should have a page with her interests listed; be sure to be forthright with yours as well. Lastly, if the provider has a screening policy in place, avoid asking explicit questions prior to being screened.
Prepare for Strap-on Sex: How To Clean Your Ass.
So, you’ve booked a session with your provider and the exciting day is coming up soon! You’re stoked and can’t wait till she opens the door. As soon as you arrive, you naturally want to head straight to the bedroom – but hold up!
Even though you may have gone to the bathroom a couple of hours ago, that doesn’t mean you’re all good to go. Quite the contrary, unless you’ve properly cleaned yourself out.
You hired someone to do intimate, culturally taboo things to a part of your body that’s often considered “dirty”.
Shit is, after all, shit.
That being said, having a clean ass is essential if you want to have an enjoyable experience and be welcomed back for more sessions in the future. I understand some of us are conditioned into thinking any contact with our asses is “wrong” or “unclean”. Though this isn’t always the case, over 10 years of experience have shown me people still feel this way, but things are starting to shift, thank goodness!
So if you really want to impress your provider, check out the guide below – trust me, it’ll be worth it! The guide is fun and easy to read, and explains how to clean your ass way better than I ever could.
HOW TO CLEAN YOUR ASS FOR ANAL SEX.
Ideally, you should prepare for strap-on sex or anal play before getting to the provider’s space. But, if you don’t have the privacy to do so, it is important to inform them and book extra time in advance. Your prep time counts towards the clock unless the provider tells you otherwise. To make it more convenient in a provider’s environment, take your own enema bulb or purchase a Fleet enema. Once you have the Fleet, dump its contents and fill it with warm water plus a drop or two of Dr. Bronner’s soap (if available). Refer to the tutorial for further instructions.
Even if you do come prepared for strap-on sex or anal play, I’d arrive with the expectation that you’ll be asked to shower before play begins.
Hemorrhoids and Fissures: A Small Warning
A word on hemorrhoids and anal fissures while you prepare for strap-on sex: if you have inflamed hemorrhoids or an anal fissure, do not pass go and do not collect $200. Anal play is only going to make the situation worse, and you should re-book the date. 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 you currently has an anal fissure or tear, ass play is absolutely a no-go.
You can learn more about anal fissures here.
The Main Event- Your First Anal Experience
Alright, you’re all set – let’s get started! Relax onto the puppy pad and try to breathe deeply – I know it can be nerve-wracking, but don’t worry – your provider should have some helpful tips on how to stay calm. Breathing In through the nose and out through the mouth is a great way to both reduce anxiety and help your pelvic floor muscles (and anus) relax. Those muscles need to loosen up in order for anything to go into your butt, so take deep breaths. Feeling aroused and excited is also going to be helpful too, so let yourself be excited about what’s happening!
And remember that you are in control of this experience. If there’s something you’re not comfortable with, let your provider know. Anal play should never hurt; speak up if something doesn’t feel right or if additional lube is needed. Communication is key here!
Finally, a few words about achieving orgasm during anal play. You may have seen it all over porn sites (though understand it’s often fantasy!), but it takes time to learn how your own body works in this area. Erections may come and go throughout the session without any correlation to arousal levels or pleasure, which is perfectly normal. Don’t worry about impressing anyone with a hard dick, just focus on having fun and exploring! Having an anal/prostate orgasm right away is unlikely, so ditch those expectations in favor of enjoying yourself and the overall experience.
It’s Not You, It’s Me: I’m Just Not Into It
Don’t panic! This is totally normal–you’re likely feeling a bit uncomfortable and overwhelmed. Your prostate may be more sensitive than expected, or you may just not be able to wrap your head around everything that’s going on. That’s alright, though! Everyone’s body reacts differently to new experiences, and I’ve had clients in the past who didn’t really like or get into prostate massage and anal play. It seems like these activities have been labeled as the ultimate sexual experience that will make everyone feel wonderful, but that’s not always true. You may be one of those people who aren’t into it at all–no worries, just drop it and move on to something else.
I remember my first time trying g-spot stimulation and I absolutely hated it! I was so tense; my brain and body didn’t know how to process what was going on so I asked for it to end quickly. However, I was still curious so with time and patience, I came to appreciate that area of my body. Prostate stimulation is no different in this sense, and can often take a while for you to feel comfortable with it.
If your experience wasn’t what you were expecting but you’re still intrigued, keep exploring! Whether by yourself or with a partner or provider–it’s possible to turn something you may not have been fond of at first into something you love.
You Reached The Finish Line
The chances are that you’ve encountered tease and denial during your anal experience; your penis was likely alternating between different levels of hardness and you or your provider were probably giving some form of genital stimulation in order to reach the desired destination.
If all goes according to plan, the resulting orgasm could be incredibly intense and that’s likely why you sought out this experience. You may find that your orgasm lasts longer or that you can get hard again more quickly – prostate and anal play are known to shorten a person’s refractory period. On the other hand, your experience may vary since results are dependent on factors like your ability to relax and the skills of your chosen provider.
It’s also possible that you’ll notice a difference in volume/viscosity when you ejaculate; sometimes cum can be much more watery and there will be more of it when compared to regular ejaculations. This is because the prostate produces additional seminal fluid when stimulated.
After reaching orgasm, you might feel mushy and unable to do much, but one thing is for sure – whatever is inside your ass needs to come out. So make sure that your provider removes toys/fingers slowly as this will help minimize messes. Even if you prepped well, occasionally some fecal matter might still appear with fingers/toys – but don’t worry too much about it as long as it’s only minimal. If you’re quite messy, then your provider will probably let you know so that next time there’s less mess.
Let The Journey Begin
You had your first anal experience and if all went well, you squicked, squeed, laughed, and enjoyed your whole way through it. If you’re into it, congratulations! You’ve found a new way to play with and enjoy your body. If it wasn’t your cup of tea? Don’t fret. 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. Should you want to try again and you liked the provider you saw, let her know! Of course, you can always seek out another provider and see if the experience is better for you (perhaps you’d even like to book me! If so, head here).
xoxo,
Erin
