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Surprises are generally unwelcome when it comes to sex, and especially to sex work.

Two years ago, I found a letter in my sister's car informing her that the blood she gave during a charity blood drive had tested positive for HIV. I didn't say anything to her, because I wasn't supposed to find out and I didn't know what to say. In the time since, there were a couple times that it sounded like she came close to telling me, but never did. I worry she never will. She has also recently had some health complications that raise concern about how well she's taking care of herself, and I am concerned that she's missing out on treatment that she should be receiving out of fear that someone in our family might find out. (Our family is a bunch of judgmental religious immigrant types.)

My sister and I have really only begun to get along in the last few years. Our relationship is fragile, but I care for her deeply. I wish we could have her diagnosis acknowledged between us so she can know that I'm not going to stop loving her, that I respect her no less, and that I want to help take care of her. But that means having a conversation that I'm not sure I have the right to start. What should I do?

Sensitive Issue Surrounds Treating Errant Retroviruses

Your sister may not be facing HIV alone. She could have confided in friends, she could be seeing a great HIV doc, she could be attending a support group. And if your sister were in good health, SISTER, I would encourage you to run with the assumption that she's getting the help and support she needs. It's generally a good idea to err on the side of respecting a sibling's right to privacy.

But it doesn't sound like your sister is in good health.

While it's possible she's facing health problems that you've wrongly attributed to her HIV infection — people with HIV can come down with other shit — that could be a risky assumption. You don't wanna respect your sister to death. If there's a chance your sister hasn't sought treatment because she feared it would get back to your family (she's still on your parents' health insurance, her physician is a family friend) or because there's some other issue (language barriers, cultural barriers), err on the side of speaking up. Tell your sister what you know and tell her how you found out. If you don't tell her how you learned about her HIV diagnosis, your sister will worry that rumors are spreading and that other people already know. So you have to come clean about snooping.

Then tell her you love her, you're worried for her, and you want to make sure she's getting the care and support she needs. She may be upset that you know something she wanted to keep secret, but you can point to the past two years as proof you can be trusted to keep her HIV status confidential. You can't be trusted with her mail, obviously, but you've proven that you won't blab to the family.

I was born female, and I've been binding for a while and identify as gender-neutral. But I'm afraid to tell others that I'm gender-neutral for fear of being told I'm wrong because I wear dresses. Does wearing skirts and dresses mean I'm not gender-neutral? I just think I look better in dresses than flannel.

Gender Neutral Asexual Youth

Wear whatever you like, identify however you like, and refuse to engage with idiots who think they have a right to critique, dictate or overrule your gender identity.

My husband and I have started flirting with the idea of "same-room sex" with other couples. We want a couple to watch us have sex, and we want to watch them have sex, but with no physical contact between couples. But we have had a difficult time finding couples that do not want a soft or full swap. I have decided to surprise my husband with a prostitute who will watch and video us but not have contact with us. I think he will be thrilled. But I am totally naive about sex work, and I'm also afraid I could get jealous since there would be no other man in the room for me! Help me avoid possible pitfalls!

Monogamous Voyeurs And Exhibitionists

"Surprises are generally unwelcome when it comes to sex, and especially to sex work," says Siouxsie Q, a Bay Area sex worker as well as the creator and host of the WhoreCast (thewhorecast.com), a weekly podcast about sex work and sex workers. "You think your husband will be thrilled by a surprise prostitute — but what if he is not?"

You're already worried that you might not be into it: You wanna be watched by a couple, but you're only thinking about hiring a woman, and that could leave you feeling jealous.

"If you are going to hire a pro, you might as well get exactly what you want," says Siouxsie. "There are plenty of escorts who do ‘doubles' with other escorts. Some providers specialize in this! Communicate with your husband, and instead of putting together a surprise, embark on a sexual adventure together. Looking through ads and picking out people you both find attractive may be fun."

Siouxsie recommends booking at least two hours for a session — you don't want to rush through your fantasy — and that you respect your sex worker's quoted rate, i.e., no haggling over their hourly rate.

"When your providers arrive, communicate your boundaries and expectations clearly so everyone is on the same page," says Siouxsie, "and you and your husband should agree in advance about either of you being able to call a ‘time-out' mid-session in order to reestablish boundaries or to talk something out. This sounds like a fun session that most providers I know would be stoked to book! So make your fantasies come true!"

For your Halloween treat, Dan secures sex advice from a mortician, at savagelovecast.com.

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