Dear Tits and Sass

Home Dear Tits and Sass

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: 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

Dear Tits and Sass: My Boyfriend’s Back

Nobody liked Logan.
Nobody liked Logan.

Dear Tits and Sass,

I was with my boyfriend for two years and we decided to take a break at the beginning of this year, shortly after which I began stripping. We recently got back together and I still can’t pluck up the courage to tell him about my new job, which I love. Problem is, his ex-wife was a stripper and he harbors a lot of negative attitude towards strippers and the sex industry in general, and has said some things that make me uncomfortable telling him (“I couldn’t date another stripper”) as well as the fact I’m scared he would tell my parents out of concern. The longer I keep it from him the worse it will look, and besides I think he suspects it already. Help, please!

Thank you,
Secret Stripper

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 & 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