We’re living in the era of the ass. In the early aughts, saying someone had a “fat ass” was an insult. Now Brazilian butt lifts are all the rage and influencers left and right are creating workout videos for how to get that Kim K bootay. This cultural phenomenon transcends beyond body standards and into the bedroom. Anal sex has basically become the new oral. There used to be this perception that only promiscuous women were into it and that it was somehow degrading. On the flip side, straight men shied away from ass play because they were afraid of giving off gay vibes. Thank god those dark ages are behind us. While having anal sex and eating ass aren’t my personal faves, it’s fun to dabble and I’m so here for the stigma to be removed.
Reflecting back on the many lovers I’ve had over the years, the generational divide is real. Guys under 35 are way more into butt stuff than their older counterparts, which makes total sense given the porn they were exposed to. Older men tend to skew way more vanilla with the occasional sex freak exception. While the older guys I’ve been with aren’t generally all that keen on sticking it up the butt, quite a few of them are into prostate stuff — far more so than the straight young guys. I’ve deduced two reasons for this. For starters, silver foxes have been around the block and have had way more time to explore their sexuality. Secondly, they are more in the know about prostate health and view prostate massage as a holistic health treatment as much, if not more so, than a sexual act.
Much like a happy ending situation, giving a prostate massage is about providing a safe space for a man to be vulnerable. In doing so, he can relax and let go of tension in his body, leaving him rejuvenated and ready to take on the world. A 2022 goal of mine is to master the prostate massage and I encourage others to join me on this quest. Similar to the special bond that forms when a man performs shibari on a woman, a woman who gives a man a prostate massage is partaking in a magical union between the masculine and feminine. It’s that kind of nurturing, non-penetrative sexual intimacy that can really take things to the next level, whether you’re in a traditional relationship or a sex-worker client one. Of course, if you are fucking some dude who is not giving you orgasms or cash, then don’t bother, and while you’re at it, dump his ass. Only kings are deserving of the royal treatment — never forget that.
As I went down a rabbit hole of prostate massage YouTube tutorials, I figured sitting down with a sex-positive doctor friend, who also happens to be an ex sugar daddy, would give me a more antecodotal look into the wild world of prostates. And boy was I right. Meet Dev. He’s a good looking heart surgeon in his early fifties who definitely falls into the sexual deviant category of sugar daddies:
Jules: So give me the download. I know you’ve mentioned falling in love with a chick who gave prostate massages for a living. Tell me more about that.
Dev: So you’re correct in that I used to date a woman who gave sensual massages to the rich and famous but unfortunately I never got to take full advantage of her expertise. You see I have this condition called prostatitis.
Jules: Da fuck is that?
Dev: I first noticed it in college. I would meet a woman and we would start making out and I would get a small erection, but I wouldn’t be able to convert because of my poor skills.
Jules: Poor skills?
Dev: You know, the woman would be like “no.” Things were very different back in the ‘80s. The AIDs crisis made people scared of casual sex. So she would leave and I would develop the most excruciating case of blue balls. I remember talking to my friends about it and they would get blue balls but not like me. I wouldn’t be able to walk for days because it would hurt so much. I also used to get this burning sensation when I peed constantly, which led me to believe I had an STD. I would go in every few weeks to get tested but the tests would always come back negative. So finally I went to a urologist and told him what was going on. He said “Sounds like you might have chronic prostatitis. Let me see.” He then proceeded to stick his finger up my ass and I fucking nearly jumped across the room, as I screamed “No, no, no.” The doctor then proceeded to tell me: “You have a really boggy prostate.”
Jules: Boggy?
Dev: So it’s soft rather than hard like a walnut, which is how it’s supposed to be. Consequently I love the idea of butt stuff but if someone tries putting a finger up there, I’m going to hit the ceiling. It’s a no fly zone.
Jules: So it hurts really bad?
Dev: It’s not really even that it hurts, it’s more of a burning discomfort which I heard is normal, but for me I just feel it way more intensely than most men. See women give birth so they can do that kinda thing. They can breathe through that discomfort whereas men are…
Jules: Fucking babies?
Dev: Ya we’re babies.
Jules: So does that put you at a higher risk for prostate cancer?
Dev: I don’t think so.
Jules: What about prostate massages for prostate health?
Dev: When done right, prostate massages are known to help with erectile dysfunction, painful ejaculation and enlarged prostates. My ex-girlfriend made it her business to give prostate massages to CEO types. Some were surgeons like me and she would tell me what they were into. This one guy I actually knew invited to her to his place while his kids were in the bedroom next door and proceeded to instruct her on which way to put her hand and stuff.
Jules: So did she only do prostate massages?
Dev: No no she did other stuff too. I got to know her through the standard handy.
Jules: So you met her through her sensual massage service and then she became your girlfriend?
Dev: Ya.
Jules: And then she opened up to you about all the prostate massage sessions she had with CEOs and shit? But she never gave you a prostate massage because of your condition?
Dev: Yup. But condition aside, she actually thought giving prostate massages was disgusting and she didn’t want to do it to someone she was in a romantic relationship with.
Jules: It’s interesting cause I feel the opposite way. Like I would only ever want to give a prostate massage to someone I’m super into. Same thing goes for anal sex. Even if a daddy was willing to pay me twice as much to fuck me up the ass, I wouldn’t be down – unless I was already really attracted to him.
Dev: That’s where you draw the line, I get it. But everybody has a different line. I actually recently took the anal virginity of my latest sugar baby. She had had some sort of procedure done when she was younger that left scarring so she was really self-conscious about it.
Jules: So her letting you in was a big deal.
Dev: Oh ya, huge deal. I actually gave her ketamine *laughs* I basically put her under anesthesia.
Jules: So what did it take away the pain? Did she enjoy it??
Dev: Ya I mean she was dissociated, she didn’t feel a thing. But she enjoyed it and was really into anal from that point forward. Highly recommended by the way. At least that’s my professional medical opinion. It relaxes the muscles and removes any sense of anxiety. In fact, I’ve actually been on the receiving end of that. One time this chick gave me a bunch of ketamine and after the fact she told me she had had her entire fist up my butt and I was like “really?” and she was like “Ya you came so hard.”
Jules: So was it some next level orgasm?
Dev: I don’t know I was high on ketamine so I don’t really remember. *laughs again*
Jules: Were you high on anything else?
Dev: Just some alcohol and a bit of coke.
Jules: Love how that’s enough to put any normal person into outer space, but for you it’s like: “Just another Tuesday.” This is why you’re my fave.
Dev: This all better not be traceable back to me! I think it’s time to stop recording.
Jules: Okay okay, just a few more questions. So all in all, your experience with prostate massages isn’t great?
Dev: So unless I’m under anesthesia, in which case it is pleasurable, I find the sensation to be very distracting to my pleasure. I mean I would like to do it. It seems to be something people really enjoy. I love having my ass eaten though, just no fingers up there. And obviously I very much enjoy partaking in anal sex when I’m not on the receiving end. For many reasons.
Jules: Gotcha. And what would those reasons be?
Dev: Number one – no one gets pregnant. Number two – it’s nasty and taboo which makes it hot. Number three – the whole “she’s letting me in” trust bond. You know I’ve talked to one of my best female friends about this and the first few times she had sex as a teenager, it was anal because she didn’t want to get pregnant. People come to their conclusions about anal with very different frames of mind and I’m fascinated by it. You know what’s wild? I’ve never had anal sex with my wife.
Jules: Really?!
Dev: Ya it’s just not her thing. There’s cultural and generational factors for sure. People cross that boundary very quickly compared to back in the day. Even in the 90s or 2000s, your average woman was not going to let you anywhere near her butt.
Jules: And what about the prostate stuff? From my experience, older men are into it. Do you talk to your guy friends about that kind of stuff?
Dev: I have my friends who I talk to about sex but most of my close friends I don’t talk to about sex because on the rare occasion I have, it’s backfired. People are just so surprised when they hear what a freak I am that they can’t look at me in the same way. But amongst the ones I can be open with, one or two of them have definitely mentioned their interest in prostate stuff.
Jules: I know the feeling. Some of my friends know about my sugaring past, others don’t and never will. Why risk putting yourself out there when you know that person doesn’t have the bandwidth to be open-minded and accepting? So not worth driving a wedge in the relationship over.
Dev: So true. That’s why I’m grateful to have weirdos like you in my life. We can just be totally honest with one another.
Jules: Aww, love you!
Dev: Love you too.
Jules
Based in Brooklyn, Jules has dedicated her twenties towards harnessing her pussy power, exploring the muse, whore, and wild woman archetypes along the way. When not blogging, you can find her sweating the toxins out in a hot yoga class or sipping a matcha latte at a pretentious coffee shop, whilst she scribbles away in her journal.
