Tales of a Middle-Aged MILFmaid

Tales of a Middle-Aged MILFmaid

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Tales of a Middle-Aged MILFmaid
Tales of a Middle-Aged MILFmaid
A Decade in the Demimonde

A Decade in the Demimonde

My sex work (Re)volution (part one of three)

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Melissa M
Dec 31, 2023
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Tales of a Middle-Aged MILFmaid
Tales of a Middle-Aged MILFmaid
A Decade in the Demimonde
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What I picture when I write about sex work, stigma, power and liberation in our secret playground (“Witches Going to Their Sabbath” by Luis Ricardo Falero)

I was less disciplined than I wanted to be with my writing this year, I hope this essay with three parts makes up for those who’ve been waiting a while. I’ve starting writing today on the winter Solstice, the longest night of darkness. I picture in my mind we’re all at bottom of the sea before we reverse course and slowly start rising up again towards the sun. The past two years have marked my bigger transformation of moving towards the light, coming out, writing about my experiences to reveal more and slowly become one person again. After taking baby steps, I strapped on the rocket booster in 2022 and thrusted myself up faster when I came out online under my real name, starting here on Substack. Every essay I publish, I exorcise a few more demons taking up space in my brain— they won't let met think about anything else until I release them so they can burrow into other people’s minds. Writing in this raw way and making it public have been self-therapy sessions, letting all of you witness it so I can bless it and let it go. I don’t think I would be the talented artist, jester and therapist without the suffering. I’m grateful for the dark experiences as it’s given me so many great stories to share, like paintings in my head waiting to take hold of a canvas and reveal themselves.

_______

It was ten years ago this month, December of 2013. I was on a week-long cruise in the Caribbean with my dad, stepmother and her children. It was a very generous gift from my parents as I was pretty broke at the time, just fired from my $12 an hour sales job and I don’t think I had any paid photography gigs that year. The year prior I took real estate classes at a community college and I passed the California realtor licensing exam on the first try, which I was proud of. But the fantasy I had in my mind of million dollar listings falling into my lap (it was the Bay Area after all) and collecting $30,000 agent fees didn’t match the reality of hustling hard to just get your first client. It was the same hungry feeling I knew too well as a struggling freelance photographer and hustling for clients (sugar daddies) as a wannabe baller escort.

When I look at the photos of us in swimming in the turquoise ocean, walking past the colorful architecture in San Juan and our smiling faces around the table at dinner, all I really remember is my feelings of longing and anticipation and how I had to keep those feelings a secret. Every day on the ship I would go to the business center to get on their dollar-a-minute, dial-up modem and check my email to see if my account was

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