Dear Tits and Sass

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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: 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: Breaking Up With a Regular Client Edition

Image via Sassyology
Image via Sassyology

Dear Tits and Sass,

I need help breaking up with a long time client. He is a very sweet guy and if I were to describe our dates (lots of time out in public: dinners, shows, etc.) it would sound like a pretty cushy gig. The problem is that I find being physical with him deeply, deeply repulsive. Not like I’m so hot for my other clients, but it’s a real challenge with this guy. I regularly find myself closing my eyes and trying to breathe without letting *any* expression cross my face—forget about me faking pleasure, I’m merely hoping to not betray my urge to run. Let me stress that he is not abusive or demanding, and he doesn’t hurt me.

I feel like he’s usually aware that I’m hating every second we’re naked together, but he’s so taken with me he lets it slide. The last time we did an overnight together, I dreamed about screaming at him that he was horrible and I never wanted to see him again. He’s not horrible, but I can’t talk my body out of feeling completely miserable during sex with him. We’ve known each other for over a year now, seen each other for long dates at least 15 times, and I have no idea how to break it off. I can’t pretend I’m retiring, and I don’t want to take down the overnight option from my website. (Seeing him for a short period of time won’t really help anyway; I’ve tried, and it still sucks.) But I’ve got to do something because in the days in advance of seeing him, I start feeling really sad and panicked. I don’t think it’s healthy for me to see him anymore, no matter how much money is at stake. Please help!

Sincerely,
SMS (Save My Sanity) 

Dear Tits and Sass: Sugar Daddy Dependence Blues Edition

When you just really need to get away from this guy.

Dear Tits and Sass,

I am an escort in Calgary, Canada and am desperately looking online for some help. I’ve been escorting for a year now and throughout the year I feel I’ve gone through some serious turmoil, and want to get out.

Particularly, throughout my journey almost right away I [met] a sugar daddy and we have had an arrangement for pretty much the whole time I’ve been escorting. Of course, he was very generous with his money in the beginning. Then it turned into an arrangement and everything was still fine and reasonable. As time went by and boundaries got crossed, I have now shared so much personal information with him and started to develop feelings in a weird way. He obviously doesn’t feel the same, as he is married, but he does use manipulation tactics to keep me interested by almost promising some sort of false hope that we will get married and live happily ever after (he doesn’t say it that way, but he gives subtle implications).

Aside from the emotions, though, he has become my top client as he provides the most income for me. However, during this time, I feel I have put up with so much emotional drainage and despair. He has manipulated me and treated me so poorly (mentally). He stays at my place for hours and expects me to text and entertain him when he’s not around. Escorting also became a problem to him at one point too. So it’s like I just can’t win and make him happy. Plus, I have to be so honest with him [about] my personal life on top of that and it’s just draining.

Long story short, I just don’t think I can handle it anymore, but I don’t know what to do. I am so scared to cut him off as I’ve been (in some ways) more comfortable seeing fewer clients due to having him as a source of income, although he consumes so much of my time and demands [so much of] it. Plus, he always thinks I’m lying to him about my “feelings” towards him and always wants me to prove it. I’m just exhausted. I’m starting to wonder if it would be better to just cut him off and go back to seeing more clients again. At what point do you end it with a client, even though I have become dependent on him? I realize as time goes by it’s just going to get worse and worse. How can I change this dynamic again? I barely have enough time for school, and I feel it’s almost like he doesn’t agree with me being in school, which is why I started escorting in the first place (to pay debt, etc.). How can I fix this mess I got myself in? I just want to be normal. Please, I’m crying for help,

SAD (Sugarbabying Ain’t Delightful)

Dear Tits and Sass: Keeping The Kids

(Photo by Flickr user notsogoodphotography)
(Photo by Flickr user notsogoodphotography)

I’m a pro domme who also sometimes does full-service work. My partner of seven years and I are thinking about trying for a kid, but I’m worried about the custody issues that might come up because of what I do for work if he and I were ever to split up, or if I got arrested, or if anything else went wrong. I trust my boyfriend, and I don’t anticipate our stable relationship breaking up anytime soon, but you never know. He’s a white collar professional, while I’ve never held a straight job: I know which one of us would look better in court. What should sex workers with children know about child protective services and how best to keep their kids?

Anxious about the future,

Sarah