I asked this over in r/ask_sexworkers but it looks like there are a lot more folks active over here so I thought I’d ask here too…

Hi there! I am 40F and very sexually inexperienced (only had sex with three people — ever — and never with a cis woman). I am considering hiring a queer SW with the intent of asking her to teach me how to give pleasure to a woman?

A couple questions:

1. On her booking page, there’s a box for describing what you’re looking for. Is this the sort of thing where I can say the above directly? Or should I be speaking in code? (sex work is not legal where I live)

2. If I were to ask her to show me how to perform oral sex on her, would that be weird? Would that make her feel, like, obligated to fake an orgasm (because I suspect I won’t know what I’m doing)? And if it is an acceptable thing to ask for, should I expect that she’d want me to use a dental dam? And if so, would I bring that or would she have it?

2–part B: Same question but for fingering — do sex workers usually want you to use gloves for manual stimulation?

1. After making the booking request, how long do you typically wait before hearing back? If for any reason she doesn’t want to cater to me, will she say so? Or will I just never hear back?

2. Another question about the booking page — the requested date and requested time are required fields. The drop-down menu literally has all twenty-four hours of time as selectable options — but if you select a weird time are they going to just say no or will they offer an alternative? Is it weird to book someone at, like, 11am on a weekday?

3. Finally, for an incall, is there a way to ask her what the parking situation is before you commit to the booking? I know this probably sounds really stupid, but I am terrible at parallel parking. Kind of nervous that I won’t find a good spot in her neighborhood and will arrive sweaty and gross. Also, speaking of which, if she says she “keeps herself clean and groomed” and “expects the same from her clients” does that mean she expects clients to shave? Or trim to a specific length? (If it’s the latter, what is that length? shaving would be a dealbreaker for me because I have really sensitive skin….)

Thank you for any guidance!