Prostrate for Prostate
“Unfortunately, with men’s health, we don’t talk about it enough, and prostate cancer gets lost in the conversation. We men need to be looking out for ourselves.”
One of the many things I’m grateful for in my short run as an escort is the opportunity to meet many different people from a variety of backgrounds and walks of life. When people hear that I used to be an escort the most oft-asked question I get is, “So what was the worse thing you’ve ever had to do?” Don’t get me wrong; I don’t mind answering this question because I have a load of stories that all tie for first place for The Worst Thing I Had to Do. I just find it odd that I’m never asked, “What did you like about your job?” Yes, being a sex worker was no cake walk. It has its ups and down like any regular job. I find it strange that when we ask about sex work specifically we like to ask and focus on the bad. You can ask some Wall Street bro what they like about their job and I’m 97% sure they will always refer to their money. But based on the number of Wall Street bros I’ve slept with, they are not actually that happy. That’s why they hire me. So I’d like to take this moment to recount a very pleasant time that I had with a couple who hired me.
Rewind back to 2015 where I was about 3 years in the escorting game. I have some experience under my belt, I’ve taken some courses, learned a bit about my limits and some basic sexual anatomy and biology, and it was around this point where my kill count had just peaked over the 3-digit milestone. I was contacted by a lovely older couple (I wanna say they were in their 50s or 60s, because I called them my zaddies) named Walter and Ben. Walter and Ben were a sexy couple; established in their careers in interior design and cuisine, respectively, nice penthouse apartment, both sporting a healthy amount of salt and pepper in their facial hair. As you can see I didn’t need money as a reason to fuck them because I would have totally fucked them for free. But alas they did hire me for a very specific job, one that I had not yet experienced therefore made me feel unprepared.
They sat me down in their chaise lounge, Walter sat just a few inches to my left while Ben went to the wet bar to mix the three of us some mimosas. I can tell from Walter’s energy that there was something on his mind. His posture was slumped and he stared blankly in to space.
“Is everything okay?”, I asked.
Walt replied, “Yeah…yeah. Just something on my mind. Wait until you take a sip from Ben’s mimosas.”
He seemed so vague about answering the truth. Not really my business, but it did tickle my curiosity.
Ben came back from the wet bar holding three champagne flutes filled with freshly squeezed orange juice, a splash of Cava, and a garnished rim of powdered sugar topped with a maraschino cherry.
Holy shit was it delicious. “Damn! This is amazing!”
“Thanks! I wanted something special since today might be a little intense?”, Ben said with a tone of uncertainty. “Walt and I have been together for 30 years now, and we haven’t had sex with anyone else nor do we want to.”
Okay? So what am I doing here?
“So you might be asking yourself what are you doing here.” (Whoa.) “Well, we heard from our friend that used your services that you’re really good at what you do. Not too long ago Walt had prostatectomy because of prostate cancer. Well now he can’t get it up. And he’s always the top. So do you see our dilemma?”
Walt’s eyes started to water. It’s as if he had lost something so important and dear to him. I get it. Men have such an intimate and close connection to our genitals and our sexual performance. To get rid of a man’s ability to cum is basically taking a limb from him. When you get rid of the prostate you can still get hard, but be prepared to say adios to your ejaculation, one of the surefire ways that gay men know they got the job done. So I knew how important this was to their marriage. Why else would they call to hire a professional? I told them that even though I still have all my parts with me, I am able to have an orgasm from my frenulum, my ears, my neck, my nipples, my back, my pussy, and my crack. Needless to say that this made them more willing to try out everything I got.
Over the course of several sessions, I met with them to redefine and explore new sexual ideals with them. Starting with getting rid of the top-bottom label and take the importance out of genital orgasms. Because let’s be real; being exclusively a top and bottom is sooo last decade. Like, really? Versatile is where intellectuals grow. And why is it that we’re so focused on cumming? I get that it feels great and it even looks great. Shit, I feel like a wizard when I make that sticky goop spray out of his dick with just my mouth. Look, Ma, no hands.
So the next few sessions were comprised of Walt lying down ass up and me teaching Ben how to top like a queen. I also taught them different positions, ways to get more intimate while having sex, and how to simply enjoy anything not intercourse-y. Can’t a girl just get off without having to use so much pelvic thrusting energy? Kissing is so underrated! Hand stuff? Give me five! And that’s all we did for a while. Helping them get reacquainted with different types of pleasure. This might be the humble beginnings of my career as a sex educator since, in retrospect, this doesn’t really feel like something an escort would do. It sounds like more of a sex coach. But really isn’t that what escorting is?
During one of our sessions while Ben was topping Walter, something magical happened. While Ben was penetrating Walter in a spooning position, Walter’s legs started to stiffen, his toes started to curl. and his dick was rock hard.
“Oh my god, I think I’m about to cum,” Walter said with bated breath. “Keep fucking me just like that.”
As Ben kept thrusting just like I taught him, Walter’s eyes started to roll to the back of his head.
“Fuck, I think I’m gonna cum too,” said Ben as he tightened his embrace around Walter.
“Fuck…fuck…FUCK!”
Walter closed his eyes and let out a loud pleasure-filled moan as his stiff cock started to flex and relax from the orgasm. Ben followed suit with his loud moan and ejaculated in Walter’s ass. You’re probably thinking what am I doing in this room while they’re fucking. Well, I was simply observing. Okay, not exactly. I was standing on the foot of their bed naked and hard and stroking myself because I felt that wearing my shirt and jeans was being overdressed. I guess having a hot escort feel like a cuckold set the mood? Hey, whatever gets the job done, right?
Both their naked wrinkly bodies glistened with rivulets of sweat in the sunset seeping through the very tasteful Venetian blinds. Trying to catch their breath, Walter tried to say something, but all he could mutter was a softly mumbled' “thank you” followed by a sob. There’s not many sexy things that can make me cry, but this was definitely one of them. I felt so honored to be part of their journey in reclaiming their sex life and sparked a new flame in their relationship. They thought they had lost something so valuable to them when they just needed a little push in the right direction. To be part of that journey was so humbling and tugged at my heartstrings that it made me tear up a little bit. Which is why it was so odd that I stayed hard.
Walter and Ben looked in my pelvic direction. “Whoa, someone’s still hard. Wanna come fuck both of us?”
Of course I did. I’m paid by the hour, right?
