"Do-gooders don't get enough groupies."
Many communities in New York and New Jersey are still struggling to rebuild after Hurricane Sandy. Please consider donating to Occupy Sandy, the Red Cross, or the Food Bank For New York City. If you're in the area, here's a list of volunteer opportunities. If you want to make a Hooksexup-appropriate donation, the Ali Forney Center, a shelter for homeless LGBT kids, was completely destroyed by the hurricane, and could really use your help. Thanks.
Sarah, 24
What's the best reason to sleep with a volunteer?
Big hearts, strong hands, and lots of extra energy to burn off. Plus, do-gooders don't get enough groupies.
What's one thing volunteering has taught you about sex?
It's probably not a great idea to keep your sex toys in the basement. Emily Post doesn't really have an approved way to dispose of a stranger's mildewed, sewage-soaked sex swing or VHS porn ruined by salt water.
"I don't really make that much money, or have insurance, so I'm paying out of pocket for my birth-control pill. Is it totally rude or unheard of for me to ask the guy I'm sleeping with to chip in for half of the costs if I'm letting him come inside me?"
Depends on whether you're sleeping with him exclusively. If he's a boyfriend or long-term fuck-buddy (who I hope has been tested if he's coming inside you), he probably knows the deal, and knows he's lucky to get to ditch the wrapper (PSA: safe sex is great sex!). It's cool to ask if he's willing to chip in what he's saving on condoms to keep his dick in the loins of luxury, especially if his finances are more stable than yours. But if he's just some guy, then it's weird to ask him and your other sex partners to subsidize the pill, especially since you should probably be using condoms anyway, if we're going to get all pedantic about it.
"I just moved to the city and don't know that many people. The dude I'm sleeping with has never made me come. He's smart, funny, and pretty cute, but we're not soul mates. Should I bother sleeping with him again?"
"The dude I'm sleeping with has never made me come and we're not soul mates" — no, you should not sleep with him again. Next question.
"The man who just broke my heart after five months of dating said he isn't ready for a girlfriend right now, even though he's twenty-eight years old. But he said he still wants to be my best friend. It's been a week since he dumped me, and I really miss his company. Can I still be his best friend?"
I don't know. Can you? It depends on how good you are with boundaries. Best friends tell each other everything. Best friends sleep in the same bed sometimes but never slip their hands in one another's pants or caress each other's faces lovingly before kissing one another good night. Best friends sometimes blow each other off for a super-hot date and text each other for outfit advice beforehand. Best friends spend all day together but generally don't fall asleep pining for each other, or keep each other's high-school yearbook photos in their spank banks. Can you do this with the guy who just broke your heart without wanting to crawl into a hole with a pint of ice cream and cry forever, or until your hair gets greasy and your boss takes you aside to ask if everything is okay?
"My girlfriend says I have to trim my ball hair before she will give me head. I don't want to. Should I?"
How long is your ball hair? It's reasonable for her to not want to feel like she's got a beard every time she puts your cock in her mouth. Trim it, bro. It's not like she's asking you to caramel-wax your nuts… though that does sound like it'd be a nice fall treat when I think about it. Just a little clean-up, and you get a more enthusiastic blowjob. What a no-brainer.
Noah, 30
What's one thing volunteering has taught you about sex?
You're not always going to get what you were expecting, but if you stay loose, keep the goal in mind, and make sure not to get yourself into a dangerous situation, hopefully you'll come out feeling like you did something good. Oh — and a contractor cleanup bag is not a condom.
What would you tell someone who was looking to meet people through hurricane cleanup?
You're going to want good gloves, some sturdy footwear, and some clothes that can get messy. It can get dark fast, so bring a flashlight. Cleaning supplies are always in high demand. Also, there's a chance that you're going to be in there for a while, so bring a snack and something to drink. Those are all supposed to be double entendres. Your mileage may vary.
Where's the best place to have sex in a pinch if nobody's apartment is free?
FEMA trailer. Is that joke in worse taste than this entire premise?
"I don't really make that much money, or have insurance, so I'm paying out of pocket for my birth control pill. Is it totally rude or unheard of for me to ask the guy I'm sleeping with to chip in for half of the costs if I'm letting him come inside me?"
Unheard of? No. Rude? No. Can of worms? Possibly. If you start getting into even-steven territory, you might not like what happens next. For example, condoms aren't free, and I normally destroy four or five every time just trying to get the box open. It adds up. Also — is your partner on anti-depressants? Perhaps because you're intolerably fixated on "fairness" and you make him crazy? He could be justified in trying to split that cost with you if you want to play that game. Think about it. Lastly, if this is just "the guy you are sleeping with," are you seeing anybody else? And if you're so damn fair, are you going to give him a partial rebate every time you shtup someone else? Can of worms, sister.
"My girlfriend says I have to trim my ball hair before she will give me head. I don't want to. Should I?"
The only bit of information you haven't given me is whether or not you want head. After that, the decision should be easy. And if the implied question is, "Does she owe you head regardless of your shrubbery," put yourself in her shoes. Can you fault her for having a maintenance stipulation? You'd probably have a few requests before servicing you, too, you filthy sailor — it's like a rambutan down there.
"How do I tell my boyfriend he comes too soon?"
I would try this: next time it happens, say something like "Goddamnit you come too soon!" followed by some kind of classical conditioning cue, like firing a starting pistol.
Carly, 25
What's your best story about hooking up with someone you met on a volunteer job?
Most of my volunteer work has been more serious and somber, so it's one of those things where you're connecting with someone in a stressful situation or challenging situation that you don't face everyday. It's one of those things where you say, "Hey, let's go out for drinks." You keep up the conversation. The dialogue. And you discuss what happened today. And maybe one thing leads to another and you go to his apartment and make out and have oral sex and then fun is had all around and you say goodbye. Sometimes you see them again and sometimes you don't.
What's one thing volunteering has taught you about sex?
That they're not mutually exclusive.
What are the ethical guidelines for sleeping with someone whose house you just helped fix?
To make both parties not feel like a whore. It gets tricky when you make it feel like there's payment due. If you're volunteering, you're volunteering because you want to offer your time to someone else without expectation of some kind of reward. So, when you become intimate with someone, there's a danger in making either party feel cheap. I think it's important to keep those areas separate. A gift is a gift, and those are two different kinds of gifts you don't want to mix.
Where's the best place to have sex in a pinch if nobody's apartment is free?
I hear in New York washrooms might be kind of popular. As long as you're not making anyone wait a long time to use the toilet, because that's just rude.
"My girlfriend is getting super into volunteer work. She never used to be so self-righteous and overzealous, but now it's all she talks about. Plus, she's overextending herself so much, I'm practically never getting any. I know it's for a good cause, but how do I tell her it's becoming an issue for me?"
Bring up the fact that relationships also need time investment. It's really exciting to get caught up in the idea that you're making a difference, but you can't ignore your present relationships because of something that's giving you a temporary high. If I were the boyfriend, I'd be very proud of her. I'd say, "I'm so glad you found a cause worth working towards and I'm impressed with how much time and heart you've put into it." But, I'd offer up my time to also get involved in it. I think that's a great, healthy way to do something together. I'd tell her, "You need to meet me halfway, but I don't want to take away from your cause. But I also want you to know I want to spend time with you. How can we make this happen?"
"I don't really make that much money, or have insurance, so I'm paying out of pocket for my birth-control pill. Is it totally rude or unheard of for me to ask the guy I'm sleeping with to chip in for half of the costs if I'm letting him come inside me?"
I think that's absolutely fair. I think it becomes tricky if it's not a monogamous relationship. If I'm a female and I'm sleeping with multiple parties, I think it might be unfair to ask one over the other to pitch in for birth control. It'd be weird to have a birth-control fund from various parties. But if it's a relationship that has longevity and both parties are invested in the common goal of not getting pregnant, I think yes.
"My girlfriend says I have to trim my ball hair before she will give me head. I don't want to. Should I?"
Ask her if she'll shave her pussy. But in all seriousness, I don't think it's totally out of the question to like your hair and tell her to be okay with it.
"How do I tell my boyfriend he comes too soon?"
I don't think you can. How long have you been seeing your boyfriend? You ask if you can introduce toys into the bedroom. I think you have to be very delicate about it, because that's definitely an ego killer and may affect your relationship and bedroom time in negative ways.
Please consider donating to Occupy Sandy, the Red Cross, the Food Bank For New York City, or the Ali Forney Center.
