This coming week, I'll be giving a hot college boy his first taste of My strap-on cock. He's watched plenty of porn, but had no idea how to actually prep for a strap-on date. Here's the advice I gave him (This is shared from the perspective of a Dominant woman for a submissive man, but is relevant advice for male bottoms regardless of D/s dynamic):
#1 - Hygiene
If you want a woman enjoy putting a cock up your ass, it's a good idea to make sure that ass is squeaky clean. Buy an enema or anal douche; you can find them at local drugstores like Walgreens or CVS, or online at sex stores like Adamandeve.com. Douche and/or evacuate approximately 1 hour before your date. After you douche, make sure to shower. Don't forget to use a warm soapy washcloth to clean between your ass cheeks.
Some Dommes also enjoy it when their dates are shaved, waxed, or trimmed. It's up to you to ask your date what She enjoys beforehand (and decide what you're willing to endure for Her pleasure).
#2 Practice First
Before having someone else play with your ass, I recommend learning about your body in a lower-pressure environment at home. Invest in a butt plug and some Maximus lube (or another lube specifically designed for anal play - they are usually thicker). If you don't want to use a butt plug, other options include anal beads, small dildos, or simply a gloved finger. Make sure that anything you insert has a wide base so that it doesn't get stuck. The lube, however, is not optional (the ass isn't self-lubricating like a pussy, no matter how turned on you are).
The anatomy of the ass is unique - there are two rings of muscle that control the anal opening. The external anal sphincter is under voluntary control. The internal anal sphincter is formed by involuntary circular fibers, which means you can't control whether it opens or closes through muscle movement. To get your internal anal sphincter to open, you need to be relaxed.
Before putting anything inside, rub a lubed-up finger or toy around the outside of your ass. Turn yourself on and be gentle. There are a ton of nerve endings in this area. I recommend putting a small object (butt plug, finger, etc.) in very slowly, by yourself, and practicing deep breathing to relax that internal sphincter. Get used to what it feels like to have something inside of you. Don't force the plug in - you'll likely clench down even more, and may inflame your delicate tissues, which can potentially cause hemorrhoids. Go slow, breathe, and allow yourself to open.
#3 Warmup & lube
In a lot of strap-on porn, a Dominant woman just shoves her cock into a man's "virgin" ass at Her whim, without lube or a warmup. This is not reality, and if you ask a woman to do this to you, She may cause serious damage. Virgins, a responsible Domina does Her best not to break Her boytoys. If you're not sure how She plays, make sure to negotiate that she use lube and warm your ass up with a finger or toy before you begin taking Her strap-on. If you want to skip the warmup, you can always show up with a butt plug already in 
Hope this is helpful! Play safe, pervs.
Kisses,
Miss Courtney
The information you have provided is very helpful - especially for those of us that lack experience in your area of expertise. Which obviously involves the use of your strap-on.
cg
Don't use the enema as it comes...pour out whatever is in the bottle and fill it with warm water and use that. There are detergents and other stuff in enemas that you don't really need and warm water will work just fine for cleaning you out. Make sure you do it properly, and I suggest at least 90 minutes, to make sure you are completely empty 
K
I know a number of pegging enthusiasts who don''t much care for the drugstore enema kits (e.g., Fleet). Most of the peggers prefer the pegees to use the (about $40) Shower Shot type of shower-head-attachment enema instead, because the Fleet kind doesn't really remove any fecal matter -- it just gets it wet and squishy, like mud. 
If you do the Shower Shot, you might find that you really enjoy the "clean" feeling afterwards. Just be careful not to do it every day. As I understand it, too many enemas can have a detrimental effect on your health by depleting the bowel of beneficial bacteria.
You also have to be mindful of the temperature of the water. What feels great to the rest of your body (i.e., a warm or hot shower) won't be nearly as much fun up your rectum. I'd also suggest dialing up the amount of water you're receiving VERY SLOWLY.
Usually, 3 or 4 fill-ups and discharges (suggest using the toilet instead of the bath) will clean you out thoroughly. You'll know because only a clear liquid (the water) will come out when you're done. Enemas take a while, and even when you're finished, you'll feel the sudden urge to run to the toilet, so please don't trying doing this half an hour before your session. Allow some time, maybe 2 to 3 hours before your session, and maybe keep your eating to a minimum "the day of".
Good luck!
Thanks - great addition to Courtney's post. Not sure the shower shot is practical when one is traveling or at a location other than home, but worth looking into.
Again, thanks for the very informative post.
Yes. The fluid in store enemas is meant to dissolve shit so it means that your purge comes out muddy and messy. It's MUCH tidier to use tap water after pouring it out. You can refill and do this a few times and it works really well. I like to use three purges, warm, cold and warm.
Also, be patient with draining the fluid out and try to do it at least a couple of hours in advance because som residual water can get trapped in the sigmoid.
Lying on your side is also a good thing to do when getting the enema.
Posted By: MistressKiley
Don't use the enema as it comes...pour out whatever is in the bottle and fill it with warm water and use that. There are detergents and other stuff in enemas that you don't really need and warm water will work just fine for cleaning you out. Make sure you do it properly, and I suggest at least 90 minutes, to make sure you are completely empty
K
Miss Courtney:
This post is a real public service to all of us who enjoy this sort of play. I hope that any ladies who aren't that experienced in this area read part 3 of your post. From personal experience, I can tell you how unpleasant it can be when a lady doesn't properly warm up one's hole before using bigger toys.
Hopefully those interested in such activities will read it and learn.
Everyone's body is different, it's also probably wise to try finding out what works for you long before you have a date
Thank you for posting - this is very similar to what I send gents via email before they arrive for session
Em
My BDSM interests initially started at age 7 with a female teacher and it was all about spanking. Later on I witnessed the severe paddling of a boy bent over and getting it from a man.
I had fantasies about that for many, many years, I mean bending over and being paddled by a man but not once did it ever occur to me that there was any "gayness" to it.
But a few months ago I saw a photo of a dominant female with a very realistic strap-on and my dick got incredibly hard. Go figure. I still don't think there is a gay bone in my body that I am, at least, consciously aware of, because females drive me crazy but I really don't know what to make of it
I would agree that if you're primarily attracted to women, then you are definitely not gay. Now if you are occasionally attracted to men, then maybe you are bisexual. But based on what you mentioned, it doesn't sound like you necessarily are. Kinky play can be different than regular sexual interactions. Sometimes we want to do kinky things with someone who we aren't necessarily attracted to, based on being attracted to the taboo element of the interaction. So you might want to get spanked by a man, but you also might not want to necessarily sexually interact with him or be attracted to him at all. Or maybe you will be and you just don't know it yet! But the two experiences don't necessarily go hand in hand. One thing I love about kink is that sexual attraction isn't always the point, so sometimes I get to engage in really fun and fulfilling play with someone who I am not attracted to necessarily, and it's still a very intimate experience that connects us, but in a different way than sexuality does. The two can definitely be practiced together, but they needn't be.
Being attracted to a woman with a cock is still a straight experience, whether she is a cis woman with a strap-on or a trans woman with a cock (or even a trans woman with a strap-on). There's some funny ideas in society about how straight men can never be into cocks (or being penetrated by anything for that matter) for any reason whatsoever, but these are pretty arbitrary standards based on insecure masculinity. Lots of straight/masculine men are into sucking cocks, being penetrated with fingers, enjoying prostate pleasure (for godsake your prostate is literally in control of your orgasm- how cool is that?!), or getting fucked with a strap-on/cock. What really determines your sexuality is who you are attracted to. Whose cock do you want to suck? Whose fingers do you want in your ass? Is it a woman's or a man's? Or sometimes both? It's all good in my book!
I'm into people of all genders, myself.
Just a word of caution for some of us older gents who might want to endulge in this activity. As an old hobbiest (63) I was seeing a provider who enjoyed this and I ended up with some issues that required a visit to an Urologist. Turns out that if one has a slightly enlarged prostate it can be damaged and cause blood in the urine. After going through the procedure where they run a camera up your penius (not the most fun I've had) I got to see the bruising on the prostate which caused the bleeding. Haven't had any problems since stopping that activity. So, just a word to ladies to inquire on us older gents about this issue which affects all older men before trying this activity.
In my experience buying those disposable enemas is not the best way to go because they have stool softener in them. This can lead to a messy situation later. If you don't have a personal one at home to use warm water than just dispose of the fluid in the store bought one and use warm water.
Another good point for a beginner is to cleanse back there several times. Keep flushing until your clean. Trimmed hair is always preferred but not required.
Also fellas, let your Mistress know your experience. I've had guys who could barely handle a six inch and other who's ass completely swallowed a nine incher. I need to know what I need to be using. No surprise.
P.S. Always thank your Mistress for all the precious gifts she offers you.
