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The boogey man phallus

Updated: Jul 30, 2021

(Writers note: This was written a few months a go for my first session with a male escort. I also talk about my past of sexual assault, and trauma. So trigger warnings apply.)


I woke up this morning happy. Yes, I got laid last night but that wasn’t exactly why I was happy. I mean it was definitely a big part of it. Finding my partner for the night was under, I think to most, unusual circumstances. See, I booked a male escort. I paid for sex. And I can happily report with much enthusiasm: worth every fucking penny. I’ll happily do it again; in fact, I plan to do it again. Some would most likely find this quite extreme (maybe?). It doesn’t bother me one bit to be honest and I wouldn’t write this either if it did. Who wouldn’t want to spend time with a handsome, smart, and well humored man, who’s great at conversation? Can I clone him and keep a copy for myself please? My standards just got a major adjustment. I’m ashamed to see how low my standards had been prior to this and how badly I had been treated and treated myself. Now I want someone who actually respects me, themselves and is good at communication. You know, going for real high bar stuff here (that would be sarcasm).


I’m thirty-one; why don’t I go down to the club snag me a hunky man to drag back and have my way with, I hear some say? To which I respond: yuck and no thanks. The Saturday night meat market does not appeal to me, I find it disgusting to be frank. Personal safety is something I care about deeply. You have no idea who or what, you’re taking back with you. And my experience with former partners; guys are fucking slack at getting tested. Common excuse is they don’t want a stranger fondling them downstairs. Like seriously, they have to lube us up and crank us open with a car jack. You can get over being fondled for twenty seconds for public health and safety buddy. Plus, I don’t drink, I’m an old lady and it’s past my bedtime. Nothing says sex appeal like a grumpy, tired, cold, and sober hag at the bar.


I tried very briefly online dating again recently (because, hey I’m lonely and I would like a companion), and again I found it’s not for me. Tinder, wow. What a wild ride of sadness. One profile still stands out to me. A middle-aged man (yes, my settings included older guys, I like me a silver fox) profile picture of some text: “If I had a superpower, it would be fucking two chicks at once”. Then his biography started with: “Hi I’m (name here), I’m a father of two beautiful girls…”. Oof, can someone please come and collect their dad off Tinder. I find if the connection doesn’t grow organically from my day to day, I have a hard time keeping interest and it’s to brittle. I get bored very quickly. How does one actually date as an adult (especially when you throw into the mix that you’re into open and non-monogamous relationships)? Does anyone know? It seems like everyone’s at a bit of a loss when I ask my friends that are in the same boat.


This is where Mister paid tall, dark, and handsome comes in. I had a specific thing I wanted Mister paid, tall, dark, and handsome to help me with in the bedroom too. Oooo, we’re getting acquainted now aren’t we. See, I have a fear of penis. Yes, I’m scared of dick. Not snakes, spiders, my bosses’ scorn, or spontaneous combustion. Dick. Thanks brain. It was so bad that even while watching naughty TV, my brain would somehow have a built-in censor bar. It caused me to wonder if I was a lesbian on quite a few occasions. Let alone the stress it caused me in actual relationships. See, everyone seems to be okay with me saying I can’t touch their naughty bits, until they want me to touch their naughty bits. Not many seem to be educated in the art of caring or respecting an obviously traumatized person right in front of them, saying they can’t do something. Willingness to communicate, consent, checking privilege and caring seems to be in short supply.


My thought at first was that this had stemmed from a prior sexual assault. My first time was rape, and I was twenty-one. A decade ago. I was finally sick off it ruling my life and I wanted to work on it. I actually had a breakthrough with my psychologist a week prior to my booking. And my problem: daddy issues. I got blindsided by that one, trust me. My dad passed away when I was thirteen, a pinnacle and crucial age of development. I remembered a random memory of my dad being a bit of a nudist (nothing nefarious) during that particular session and had a chuckle. My shrink looked at me with huge eyes. Turns out that had been the missing link to my problem. Go figure. Teenager dealing with immense grief which stops further mental and sexual development for several years. I think you can put the link together, because I’m not willing to write it just yet. But I always felt a tremendous amount of disgust, shame, and guilt in connection to anything to do with a penis. I had always just categorized it under rape, and why would I want something that caused me so much trauma. Boy was I wrong. It was like a switch in my mind got smashed on. I was tasked to exposure therapy and had to google some images. Suddenly I could actually look at them and see them. And quite honestly, I’m not sure if I’m better off or not. No offence guys, but it isn’t pretty.


Now the new problem here was I wasn’t about to trust anyone with my safety, let alone my vulnerable mental health on the issue by picking up Dave from anonymous bar three. I have a connection in the sex industry, so I get some insider info on the gig (plus hilarious work stories). Sex workers really do have better work stories, just saying. It was because I had this connection and exposure, that I started thinking maybe an escort would be the best way to go. And it just so happened that this particular one which came recommended was touring in Wellington. I cursed when I saw he was booked out. I couldn’t leave it however, as I had resolved within myself that I wanted to fix my problem of the boogey man phallus. So, I messaged him a week or two later. Asking if he knew anyone else in the area that came recommended. Turns out he’d had a cancelation. My bravery faltered for a bit as it suddenly became real as we booked a day and time, and I paid the deposit.


The week prior was filled with anxiety. I was scared. Went back and forth wanting to cancel. I didn’t. The day rolled up quickly and when I got the message saying he was outside I almost threw my phone out the window. It was ‘D’ time. I stood for a second behind the door to breathe for a second before opening it. And there he was. It can be an art form, communication, and he was an artist. Best way to get people to relax is to find common ground and to relate. I was comfortable within ten minutes. I over analyze everything, trying to dissect everything as it happens, a bad trait sometimes. So, it was interesting to feel it happen in real time. Not that it wasn’t or couldn’t be genuine, but I couldn’t help trying to pry apart what was “him” and what was the professional. Even though it is the same person, the professional is always an extension of the other and vice versa. They’re both real. Like writing a good character for a novel, they’re just extensions of ourselves. Personas are like small talk. Everyone does it and has it but I’m realizing I really don’t care about the weather. I’d rather know what do you think is the meaning of life? I want something to chew on. And he gave me something to chew on… Not just metaphorically.


What followed after our hour of chatting, was an hour by which I realized we have a huge problem in society: a lack of communication in the bedroom because its uncomfortable. I knew this within myself, experienced and witnessed it. With him, it was the most respectful hour I’d ever spent with someone in an intimate nature. And it was easy. Well, easy in a sense he showed me how easy and normal it should be. He literally just asked if he could do things. I asked if he could show me something. That simple. A sentence. A few words here and there. It didn’t “disrupt” the flow (which is an excuse I have heard), but it actually added to it. He gave me space to try and face my fear and there was no judgement or pressure. I feel sorry for the next poor sod to cross my path. The bar to entry got lifted drastically. It showed me my own issues, how low my self-worth had been. My self-esteem had been whittled away to where I found it hard to take a compliment. He helped me realize a lot about myself in two hours. And for the whole penis ordeal. Well, they’re still weird. That’ll take a while to heal. It’s just a meaty joystick that I’ll have to learn the controls for. But for now, I’m happy. I faced a fear and got further than I thought I would. So, there will be a part two to help me get even further. But like my time with Mister paid, tall, dark, and handsome; my word count is up. So, see you again next time.

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