On the Importance of Pillow Talk

I am very lucky to say that I usually have good, if not great, sex. My first time was stimulating and lackluster. With its vilification during my upbringing and being the subject of so much art and ritual, I was certain I was missing something essential and so I set out to find it. A few months after the initial experience, I did a very me sort of thing and stumbled into the good stuff: met someone[1], embarrassed myself beyond all possible reason, and the next morning had the best sex of my (then) life.

Prior to falling in love with sex, if I needed a reset or to take a pause, I’d read something that grabbed at me or walk until I found something that was impossible to look away from, searching for anything that took my breath and mind away to fully engross me. Now that I’m someone who frequently attends yoga classes and meditates regularly, I’ve found the word to name my search for stillness and clarity of mind: freedom.

Good sex was where I felt my most free and I was searching to find how this magic was created. (I have a few more things to make me feel free now, but sex is still in my top three). I could be my most adamantine, uninhibited, curious, and emotive – all of which was rewarded with pleasure and a blissfully thoughtless mind. There are many reasons why I’m in Boston, to why I’m an escort but topping the list is this deep need to chase my love of freedom.


When I mention that I am a person who trends towards an exacting, anxious and a strong type A personality, my clients generally tell me that they have yet to experience a hint of that side. They comment on how much they see me as a free spirit and someone who is wholly herself. I squint because how other people see you is always fascinating a foil to how you see yourself. After leaving it to let it percolate on the back burners for a couple of years, I’m beginning to see what they see.

As I’ve gotten older and more confident in myself and certain in who I desire to be, that’s softened to going with the flow, valuing how well I know my mind and desires, loving to spoil myself, and leaning on the knowledge that I can leave any situation in which I am not comfortable. There is no need for me to be exacting, where my boundaries start, and end is with what I will allow and if there’s something outside of that – I enjoy the privilege of leaving whenever I want to. Luckily, I occupy a privileged place in this industry where over 85% of my connections are: special, affirming, loving, caring, respectful, funny, joyous. Life changing. I’m blessed and humbled by the kind and wonderful men who share themselves, their joys and struggles and how deeply they respect the lines our relationship have.


Under the spell that our shared patient and authentic exploration of how we fit together as humans, we give ourselves freedom from expectations of who and how to be. The anonymity and lack of expectation has given space for candid and unintentionally life changing conversations for me. A part of me knows that this is simply the magic of human connection, but I want to honor these emotionally intelligent and honest conversations I get to have, often with men. There’s a lot to be said about the way emotional intelligence is vilified and ridiculed in men, and here I spend my time such sweet, kind, and humorous people who have decided who they will be for themselves, choosing the life they wish to lead. So, in an effort to be a little braver like my dear clients: Lexapro.

Now I know 5 mg of Lexapro sounds a bit silly to be writing a whole blog post about, but like these simple post coitus conversations – it has meant a great deal to me and changed my quality of life for the better. This life changing work that humans do for each other simply through existing and interacting, even and especially when silly and nonsensical, is what makes this space so precious to me. Likely unknown to my lovers is that I’ve been deathly terrified of mental health medication and its unpredictability, the adjustment period, and the lack of control I may feel if it worked for ‘relying’ on aid. While I likely was neither this verbose nor candid in my fears on my dates, I listened closely to these men as they spoke casually of their medications. Especially to how much joy, stability, and freedom it brought them to choose life on their terms. Giving them more options and for them the expanse that is life became wider, not more narrowed, allowed me to see it as an aid and a friend[2].

So, in short (for the skimmers), another message of gratitude to getting to be Jennifer Green, escort.[3] The recipe for good sex is clear: openness of myself and my partners to keep judgement and unnecessary restraint far from our pleasure. I am thankful for being consistently given lovers that are curious, open-minded and possess strong senses of humor.

And yes, I still have my earth-shattering orgasms. Thank you for inquiring after the health that matters.


(scroll for footnotes)

[1] He was from Boston, funnily enough. If you ask me about the story in person and promise not to judge me (I was horny), I’ll tell you.

[2] Like vibrators and cock rings.

[3] Never Esquire. hahahaha

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To the Last Year and Those Ahead