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Dear Tits and Sass: The Hooker Slump Edition

Image via Business Week
Image via Business Week

Dear Tits and Sass,

I’ve been an escort for 3 years now. I’ve painstakingly built up a great brand that is original and true to my personality, I update my website regularly with new text and pictures, I keep my blog relatively up to date. I advertise on four different sites (3 local, 1 national.) I have completely plateaued in my business, and I have no idea what else to do. I have a local core of clientele but lets face it, it’s not paying the bills. How do I shake out of this hooker slump? Is it just time to pack it in?

Sincerely,

Down in the Slumps

Alice: There’s no need to pack it in unless you really want to. You’ve got options!  It’s great that you’re keeping your website up to date, and that’s probably a piece of what’s keeping your core group around. The trick, though, is getting new clients to get to your website via your ads. Since you advertise on multiple sites in your local market, try diversifying your ads with different photos and approaches on each and keep them as fresh and updated as you do your website. It might seem counterintuitive, but taking an ad down for a while can give your business a boost, especially if you’ve been advertising on the same sites for the majority of your career. 

Dear Tits and Sass: The Client Boyfriend

(image via Flickr user frankieleon)
(image via Flickr user frankieleon)

My BF is a former client. When I first met him I was in my early 30s and really popular. I saw him once or twice… I missed a couple appointments and he stopped seeing me.

Over the years my business slowed down. I operated UTR, mostly relying on regulars…After almost eight years my client who would become my BF contacted me for a date. I didn’t remember him, but he showed me an old review he did about me back then on one of the boards. He started seeing me twice a week. We did some overnighters and we started spending social time together. He was open-minded and generous. At the time, I was barely making it. He started paying for dates in advance. He signed a lease for me and he wanted to move in.

I liked him, but I was still escorting. I wanted him to help me, but I wasn’t willing to give up my freedom. He said he could deal with me not living with him and me continuing to work. He was OK as long as we still saw each other regularly.

[But] after a few months, it was clear that the relationship was really stressing him out. There was tension between us around me not operating securely enough. He tried to give me instructions about running my business. After some arguments, he finally conceded that I had been doing this for a long time and that I knew how to take care of myself.

He never asked me to quit, but I knew every time I told him that I had an appointment it caused him pain. Bottom line, I told him I was retiring. He was so happy. I told him I would go to school and get my education.

So for nearly two years I have been lying to him. I did go to school, but my school closed down. I took down my old contact information, but my review site is still up with all the old information on it. I changed my stage name and I have been operating UTR for nearly two years. He still pays my rent but threatens to cut me off unless we live together. He looks for me occasionally on the boards, but my new name protects me and he wants to believe me.

He loves me. I love him like my generous uncle. His money is not endless and he wants a commitment or he is going to cut me loose. I have mixed feelings. He has been good to me and he has given me a lot. I have a five-year-old. My BF has been generous and kind to her.

I’m getting older, but I think if I was more public I would still have a good five to eight years to make money. Should I give him a break and let him go while he still has some money left?

Sincerely,

A

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 and Sass: How to Retire Edition

wrt
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: 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