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Dear Tits and Sass: How to Retire Edition

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Image from LasVegasLawBlog

Dear Tits and Sass,

I have been a sex worker for about nine years now, in a variety of capacities.  The past three years I’ve lived and worked as an upscale independent escort in a several different cities. I have regulars in three cities, a website, and a mailing list with about 800 people on it. This fall I’m starting school, working towards a professional degree (in a city where I have never worked). I am trying to come up with the best plan for resigning from the business, while keeping the door open to work again if I need to or want to. The risk-benefit analysis favors very heavily on the side of completely quitting and trying as much as possible to erase all evidence of ever having existed (taking down my website, delisting off TER, deleting my gmail account, etc.). In fact, I have become even more paranoid than I used to be about screening, because if something negative should happen now I would likely lose my ability to pursue the professional degree I’m after and have to keep doing sex work (I’m feeling burnt out and ready to move on) until I came up with another plan. But part of me fears losing this business I spent so much time building, in case I should need it (with an already established good reputation) in the future. I also wish to keep the ability to call on my regulars, so as to work without advertising (if I want to)—and I don’t want them to know where I’m going to school or even what city I’m moving to. And, to some extent most relevantly, I want to make as absolutely much money as possible before I retire my online presence (as much as possible, given the number of “stolen” ads of mine that are floating out there) in August. What are the best tips and tricks for getting the most cash out of retirement, and then disappearing off the face of the internet, without burning all my bridges?
Sincerely,
Goodbye To All That

Dear Tits and Sass: Dating Edition

Those two biblical lovebirds, Ruth and Boaz. (image via the New York Public Library Digital Collection)
Those two biblical lovebirds, Ruth and Boaz. (image via the New York Public Library Digital Collection)

Dear Tits and Sass,

I’m 28 and I’ve been a stripper for almost seven years. The last couple have definitely been the hardest, but the most profitable. I’ve created a life better than I could have imagined for myself before I started dancing—riding horses at nationally rated jumping shows, buying a house, driving a nice car, zero student debt and actual time to go to college as an adult, traveling to marathons and going on luxury vacations often, eating healthy food, and more. I wake up every day to a life I love, good friends, my pups. I’ve spent the single years doing my own thing.

I’m ready for and really want a partner. I haven’t dated in almost five years, save for a month of dating an impotent obese man. My 65-year-old customers probably have exponentially more sex than I do. Dear God, I want a steady flow of conversation that doesn’t involve being paid, and holy cow I would love a steady supply of dick before my vagina dries out like the Sahara. Online dating was a big fail on one free site and two paid sites—the few dates I had were either okay and didn’t work out, or sucked. I choose not to date customers of the club I work for as a personal boundary. I’m not so much into casual sex, but the few partners I’ve tried have led me to believe that I’m an unsatisfying-penis magnet.

It’s gotten to the point where even thinking about dating really sucks, and makes me unhappy for days when someone brings up the idea. It seems like as soon as I reveal my job, guys either flee or do the “trophying” thing until it quickly gets old for them. Recently, a friend wanted to introduce me to her boyfriend’s attractive pal. When I asked her if she’d told him about my job, she said she and her boyfriend would wait for me to tell him.

I feel like I’m tricking someone into a date with me if I don’t come with a huge red flag, a scarlet “S,” and some infamous Jaws-esque warning music. I don’t want to quit my job, and I’m not apologetic about what I do, but it does seem to be a big deal to men who aren’t meth addicts, have all their teeth, and live indoors. I don’t think it’s fair if they’re set up on an outing with me if they’re being…um, tricked. I’d want to know if someone was setting me up with someone that had a pretty big possible dealbreaker.

My question is: How in the fuck do I start dating again? Do I tell prospective gentlemen about my job, and when? Should my friend tell this man about my job before he decides whether he would like an outing with me? Do I lie entirely for as long as I can, despite my work being at obvious hours, and the stilettos and g-string laundry that litter my house? How long do I lie? Do I really have to wait another six-to-sever years (quittin’ time) before men will take me seriously as a partner?

Sincerely,
Calloused Masturbation Hand

Dear Tits & Sass: Overly Attached Client Edition

Dear Tits and Sass,

Last February, I met Phil off a sugar dating site. He was extremely effusive in quasi-personal affection towards me during our first meeting, to the point that I realized he was an attachment risk and considered not seeing him again. (He’d had a recent and extremely nasty divorce.) But I agreed to a monthly arrangement of x dollars/month for indefinite weekly meetings and saw him three times total. In addition to sex, he wanted an intellectual relationship.

Between our meetings, Phil frequently wrote me vaguely romantic emails, with very familiar addresses and conclusions (things like “dear love,” etc.). I am married and he knew that. Eventually he was sending me such intense emails that I concluded he actually thought he had fallen for me. The last piece of evidence for me that things had gone too far was when I went over to his house and found a picture of myself on his mantel: He had learned my real name from a careless mistake I made, found my Facebook, and got the picture from there.

I didn’t return his calls or emails for awhile. He sent me several distraught emails and I finally emailed him, apologized for being uncommunicative, and told him that I couldn’t see him anymore because I was concerned he was getting too attached. I was pretty blunt, but toed the line between being a person breaking up with a lover (as was appropriate to the stupid sugar game we were playing) and an escort cutting off a client (I, for example, referred to myself explicitly as an escort/sex worker in the email). I told him my role in his life should be therapeutic and motivational, not romantic, and that I did not think that was possible, basically.

He sent me a recent email proposing we keep seeing each other, just less frequently, and I did tell him I’d respond to it (oops—maybe shoulda held my cards), and I am hoping there is something I can do to let him go. I also am nervous because I (a) don’t want to acquire a stalker or something, and (b) he has my real name, which means that he could conceivable out me if he felt sufficiently jilted. Don’t know if he’d do that or not. (My husband knows about all of this.) What should I do?

Sincerely,

Unhappily Loved One 

Dear Tits and Sass: My Parents Found Out I’m A Stripper Edition

One way to convince your parents stripping might work out
One way to convince your parents stripping might work out

Hello Tits and Sass,

I am a dancer in Canada and have been reading your great blog for over a year; I have also had the recent experience of being outed to my parents a couple of days ago. I have only just turned 20 so I haven’t moved out yet and am extremely mixed up about how to deal with the situation calmly. I am cut off from any coworkers for a few days (so I have no women who understand my perspective to ask advice from) and my parents are attempting to take control and make me quit (which I have no desire to comply with, I have been stripping for a year and am happy). If anyone has any words of wisdom, a post about the topic would greatly be appreciated.

Best regards, Claire

Dear Tits and Sass: Boundaries

boundaries2Dear Tits and Sass,

I’ve been a worker for around ten years now and have been full time for around the latter half of that. Navigating having a partner while being a worker is nothing new to me. However, I’ve been with my current partner for around a year and over the last few months I’ve started to worry about possible whorephobia and manipulation around my work.

A few of my regulars have become friends over the years, a few of whom I’d see socially (like going for dinner/drinks tagged onto a booking), communicate with socially (off topic chat and not just admin style arranging bookings kinda contact) and when this has happened, it’s been driven by me and stayed well within my comfort zone. But now, these long-term regs are backing off because I’ve created distance due to my partner’s difficulties around it, and I’ve not provided them with a solid reason why. I don’t know what to say to them other than being busy, but with no explanation a few of my crying manbaby clients have taken it personally and I’ve lost their custom!

I lost another client because activities happened during a session which were outside of what my partner and I had agreed (which was down to miscommunications and misunderstandings, rather than me deliberately ignoring anything that we’d agreed). The culmination of this happened when my partner had overheard something while I was seeing my client at my incall space, and didn’t like the sound of it so looked through the air vent to see what was happening.

I felt sick that she had been doing so without my prior consent, but obviously she was angry that I hadn’t respected our rules and it must’ve been a pretty tough way for her to find out. I heard doors slamming and told my client to wait a moment, and paused the booking to go and talk with her. I tried to calm the situation and said I would finish up with him so we could talk properly after. This wasn’t good enough, and she walked in on him, shouted at him, and then stormed out. I didn’t know what to do so I apologised, gave him his money back and then asked him to leave. Another regular lost.

Most of my clients are older gents but one is younger, and as such I adopt a more casual, familiar tone with him. My partner read through my work e-mails  and at first, said “I know it’s work, you’re flirting on the internet for money,” which felt accusatory but at least partially understanding. But later, she said that she didn’t like the way I spoke with him and she didn’t want me to see him anymore.

And then there’s my most frequent regular, who did become emotionally needy and made attempts at boundary pushing—but the situation was manageable and still worthwhile from my point of view. She genuinely felt he was dangerous and even though I wasn’t sure if I agreed or not, I did take her concerns seriously and I did stop seeing him.

Since I’d been working for so long, I’d almost built up enough regs to not need to screen for new clients—something I’d been working towards and hoping for, for quite some time! But now, it looks like my regs—newer and older—are where the issues lurk. I won’t stop being a worker for the sake of my relationship, but at the same time, I do want to respect her boundaries so that we can both feel safer and happier about it.

She considers me to be financially well off, and as such she thinks I’m secure enough to be able to cherry pick only the best or easiest bookings. I’m not doing survival SW, but I do flex my work practices around how much money I need at any given point. She struggles to comprehend why I see certain clients/permit certain activities when I “don’t have to”, and the only reason she can find is that I’m apparently greedy and money-obsessed. In reality, her comfort zone around SW is different to mine and on top of that, I’m far more of a workaholic. But when she is critical/questioning of certain things that I do with clients, it makes me feel like she’s being judgmental and whorephobic.

Ultimately I’m wondering if the issue is with her lack of trust in me, or if it’s to do with me being unreasonable in the way I work, or if it’s her being controlling and critical in ways that are unfair or even emotionally abusive. I do respect her right to tell me how she feels about my work, and I do want to accommodate her as much as possible, but when she gives me ultimatums then I worry that it’s gone too far.

Sincerely,

Overwhelmed