Vol. 1, Post #4 Assholes are like opinions – everyone has one.

A Dear Reader requested some ass. Some ass-ssential thoughts in my ongoing sex tips for girls* (*girls who are holding on to their mid-life by a thread). A dating odyssey for Young Olds.

Sometimes when I’m in bed with my favorite lover, he’ll turn me over, gripping my hips, and then deliver a loudish and resounding slap on my ass, growling, “Gimme that. So big and juicy…”

This lover often says to me “I love your big juicy ass” and as seemingly well-adjusted as I am, or pretend to be, a comment like this stops me in my tracks for a nano-second. Because even though I know he’s paying me a compliment, and also calling my attention to something that he finds desirable, in that moment, he is unleashing a double-edged sword of a word: Big. And there is never even one instance where I don’t open my mouth to begin to reply something like this, “I go to kickboxing three times a week; what are you talking about, ‘big’?” Then I stop myself. In his eyes, I am sexiness and beauty personified and he finds one of my assets particularly alluring, a part of me that sometimes can give me cause for pause in other settings.

I’m bringing this up because last week, I emailed my subscribers (and posted on social media) that if anyone wanted to suggest a topic or ask a question, I’d be all ears. And TWO readers reached out. Guess what they BOTH wanted to chat about? Excerpt from one of their emails below.

“Hi dear Abbe, (it was fun to type that). Ok, I’ll bite. I have a new partner (we are both in our sixties) and he touches me in ways that used to make me uncomfortable, as I wasn’t so happy with my body when I was younger. These days, I’m pretty open and I think I want him to spank me, or maybe have us try anal sex but I also don’t want to freak him out and am not sure how to frame my request. And speaking of freaking out, I’m doing that to myself right now. I just looked at my naked butt in the bathroom mirror and while I think my partner would be excited about experimenting, I will die of embarrassment if he makes any jokes about my ass.”

Ok, let’s go. Ass play. *

*For the sake of this post, I’m going to use the phrase “ass play” to cover any fun you have with your ass, or the ass of another, not just anal. It’s a small world after all.

I’ll start with me and my ass (after all, it IS my Substack). The obvious not-entirely healthy reaction to words like “big” aside, I know what I look like naked. I’m 5’9” and old school curvy and have been this way since I first sprung tits and hips during the last few years of high school (after years of being precisely this tall but training bra-gangly). I’ve written here that I’m a fan of being naked but even that has its limits and now it’s time to fess up. Like John Travolta in his black bikini 70s underwear gloriously shot from a camera at thigh-level, blowing dry his hair in “Saturday Night Fever,” flexing along with his Bruce Lee poster (oh John), most of us can mug it up pretty good in the mirror before a big night out. Now turn around and try that from behind. “Whose ass is THAT?” I sometimes ask myself when I’m getting ready to head out. Is my mother back from the dead and standing naked in my bedroom, shakin’ it (ew)?

Now let’s add in this: How many times are you balls-deep in the action, when suddenly you think, “Um, how is this looking?” Even with the best lighting, seeing yourself in the throes of fucking is usually not such a pretty moment, particularly if you’ve assumed a position that might not be the most...flattering. I think my Dear Pen Pal might be feeling this. I know I have a vague sense of what I look like most of the time I’m in bed with a partner but when a request for something new comes in, all of that goes out the window.  That aforementioned lover, the ass man? We video and photograph each other all of the time. We both love it. Neither of us are running for political office, so as Michelle says, who cares! We’re pretty adventurous, and I’ve seen the footage, so I’m not exaggerating when I say that I’d describe my overall vibe in any given photo/video session as sort of like Slimer in “Ghostbusters.” Ravenous and slightly scary. Not hot. Doesn’t matter.

Unofficial poll here: Women, raise your hand if you prefer to be on top during sex because that seems the most “slimming.” Wish it were not the case, but I hear that A LOT. (Slimming, not sliming, see above paragraph).

So let’s go back to my Dear Pen Pal’s question, which seems to be two parts. Maybe even three?

1.     How to ask for a spanking.

2.     How to bring the focus around to her ass if she’s never expressed that it may be an erogenous zone for her, and maybe…just maybe…

3.     How to approach first time anal sex.

Here goes.

Dear Pen Pal, unless you are prone to baby talk in bed, I’d say stick with the obvious. “Spank me” or “I’d love you to spank me” OR “Would you like to spank me?” If you’re uncomfortable about making a direct ask, might I suggest that you wiggle your ass on over to your partner, maybe even bend over and run your own hands over it, or pull your partner’s hands onto your ass and encourage them to have a good, long feel? In most cases, your body language will convey, “I’m enjoying my ass and I’d like you to enjoy it as well.” Should your partner take your lead and give you a curious slap, USE YOUR VOICE to convey pleasure. Purr, growl, say “yes” – whatever works for you in the realm of your sex, and then you’re free to tell your partner harder, lighter, more, whatever turns you on. This will not be Rocket Science, I assure you. Once you’ve found you a way to convey your desire, turn up the volume, literally and figuratively.

Let me toss this out to my foxy female readers who are roughly the same age as my Dear Pen Pal. For most of you, in perimenopause, or menopause, or the years that follow, your ass is, well, probably different than you may care to acknowledge. For many, it’s bigger. Or perhaps it’s lost some of its shape and is now flatter. And in both cases, it’s also possibly inching its way towards your ankles. Totally normal. The female body stores fat in different ways as we age, and things shift a bit. For those females with same-sex, age-adjacent partners, this could be of slightly less concern – like sees like and all that. For those of you with male partners, I’ll direct you back to my second post here on Substack and remind you that men like to see naked women, period, and what may give you some concern isn’t even registering in their minds when they gaze upon your glorious nude body. One advantage of having a “big, juicy ass” is the satisfying sound you hear when someone slaps you on it and an aging ass, with its extra padding, might be the crème de la crème in this capacity. Another hooray for getting old!

Like anything, spanking requires consent. Always a good idea to discuss pain threshold in any intimate act. Speak up before and speak up during. Do you enjoy seeing your partner’s handprint on your body as a takeaway? What about bringing paddles, restraints, or toys into the mix? Here’s what I know. If there is something that is ENTIRELY off the table, the time to bring it up is before your clothes come off. What about LANGUAGE around ass play or anything outside of “the usual”? My petite Lovey Dovey Lady B. knows the story about a former British boyfriend of mine who loved to tell me how “naughty” I was in bed, particularly around anything ass related. It reminded me of a bad Monty Python skit. I HATE the word “naughty” as it pertains to sex. Tomato-tomato, huh?

Turnabout is fair play, so, besides thinking about what you might like, what’s your feeling on receiving a request to slap your partner’s ass*, or on ass play that includes tonguing (rimming) or fingering, yours or theirs? Maybe your partner has a desire they haven’t voiced to you, and now seems like as good a time as any to ask. Go ahead, while we’re young. Oh wait…

(*It’s vital to me to pause for a moment and reiterate that violence in any capacity is a hard NO and for some people with trauma in their past, any sort of “rough play” in sex is absolutely out of the question. We all must have supreme governance over our bodies. The end.)

Should we circle back to everyone’s heart of darkness? Let’s talk a little bit about your asshole, Dear Pen Pal, but this is also for any of my Dear Readers. How well do you know it, outside of its day in-day out function? I’m going to suggest that if you’ve gone half a century or more with a modicum of knowledge of what you enjoy in bed, now would be a great time to experiment with the unknown and for many people, ass play is a slightly new frontier. And if you’ve spent the majority of your life thinking that this particular pleasure was something our Gay Brothers owned outright, it’s time to shuffle the cards and deal yourself in if you’re curious.

But…

Lest you think we’re going to get into the how-tos on anal sex here, deep exhale, ok? We are not. For that, I’ll send you over to Dan Savage for this oldie-but-goodie, or even Cosmopolitan for this primer. I’m fairly sure that any of you who want to learn more about HOW to have anal sex can easily satiate yourselves on Google and earnestly read up, or nervously laugh yourselves silly. You pick. Here are the Cliff Notes: no matter how much lube you think you need, add more (good tasting lube as well, if you want to dabble in some rimming).

Another unofficial poll here: Men, raise your hand if you like your prostate massaged, either on its own or during oral sex. I thought so. Well-trimmed fingernails are key here, for everyone (women can experience deep orgasmic pleasure when their partners finger their vaginas in tandem with fingering their anuses, but PLEASE, separation of church and state. Don’t mix mediums, as it were. Fingers, toys, phalluses, et al that have been inside of an anus need to be cleaned before being introduced to a vagina to avoid infection).

Remember I said, “no baby talk” when it comes to asking to be spanked (unless that’s your thing)? Big girl and big boy pants about the following too, please: Despite the fact that, literally, no one alive can claim otherwise…despite the fact that overly precious retailers have tried for years to entice shoppers to pick up tiny tomes with titles like “Everybody Poops” as gag gifts at cash registers…despite the fact that tushy wipes are not just for incontinent oldsters and that the popularity of home bidets is through the roof…most people get wildly uncomfortable at the thought of any anal in their sex for one reason. Sex and assholes can be funny bed partners, with a whole new slew of sights, smells, and sounds. To coin a phrase: Shit happens. With a caring partner, no one will bat an eye and with the best partner, any needed cleanup will be followed by some ferocious cuddling.

(Shout out to my ex-husband and the time that I unknowingly had an intestinal parasite and had to poop on the Gov. Mario M. Cuomo (née Tappen Zee) Bridge. What a cool customer he is, and a sweetie pie; he gave me no shit about any of it. This scenario also led to a lively song penned by one of our most clever friends, “Crappin’ on The Tappen.”)

Thanks for writing Dear Pen Pal. Maybe it’s time to create a Young Olds’ sex positivity bingo card.  Email me at whatsshovegottodowithit@gmail.com if you’ve got ideas for some of the squares. Ass play might be center hole, I mean, center square.