Advice

Sex Advice From People Riding the Subway in Their Underwear

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Q: What's the proper etiquette for hitting on someone whose pants are already off? A: Half the work’s already been done for you.

AdamAdam, 27

Why are flash mob and Improv Everywhere participants better in bed?
They’re willing to try new things and don't mind putting themselves out there. Open-minded people are better in bed.

How did you choose what underwear to wear on the No Pants Subway Ride?
Last year I had no idea what to wear, so I put a lot of thought into it this year. I think that boxers are cheating, since they’re basically shorts. I went with boxer-briefs with penguins on them. I think they’re appropriate with all the snow out, and they’re fun.

Are Improv Everywhere events a good place to pick up girls/guys?
Yes! You already have something in common, and you know they have an outgoing personality. Strangely, people are more relaxed when they’re not wearing pants. They’re definitely a lot easier to approach. 

Sex with my long-term partner is getting boring. What are some easy ways to make it fun?
I'm a big fan of outfits, toys, or doing something you know you shouldn't. Let me in on a dirty secret, like that you’re going commando for the day. Or send me a picture of a new toy you just bought. Even texting dirty while together in a public place can be a lot of fun.

My roommate has walked in on my boyfriend and me having sex twice now. I'm beginning to think she's doing it on purpose. How should I bring it up?
I’d bring it up casually in a joking matter. You don't want to come off as aggressive if it was on accident. Maybe stress that she should knock first before coming in, or even resort to the sock on the doorknob if it turns into a big problem. 

The idea of making a sex tape with my boyfriend really turns me on. How can I convince him to do it?
Tell him it’s something you’ll watch while you’re alone and wanting him. Also, sex tapes are fun to watch while having sex. He really shouldn't need too much convincing. 

I recently slept with a guy who was more groomed down there than I am, and he seemed grossed out by me. Do two people have to be on the same pubic-hair wavelength to make it work?
If you're in a relationship, you just have to communicate what you want. If a girl’s going down on me, I’m going to try to please her with grooming and vice-versa. If one person is asking too much, maybe a compromise can be made. Example: if the girl doesn't want to go completely bare, perhaps she could have a small landing strip.

My new girlfriend got pissed that I'm tagged in pictures with my ex-girlfriend on Facebook, especially since my ex and I are on good terms. She's convinced I must not be over the relationship. What should I do about it?
Stress that there is nothing wrong with being friends with your ex. Ending things on good terms is a lot better than having a bitter ex. Emphasize that, clearly, you have chosen your current girlfriend. You wouldn't be with her if you still wanted to be with your ex.

I'm really into this girl I'm seeing, but she never goes down on me. She feels it's degrading. Should I just drop it, or is there a way we can compromise?
Compromise. Suggest trying to 69, since it's more mutual.

Amanda

Amanda, 26

Why are flash mob and Improv Everywhere participants better in bed?
We're spontaneous, fun, and obviously not too self-conscious.

What's the proper etiquette for hitting on someone when their pants are already off?
You don't want to be the creepy guy overtly checking everyone out. Make eye contact, smile, the usual stuff. But you can definitely say something like, "Nice undies!" (Don't call them panties. It's icky.)

How do you choose what underwear to wear on a pantless subway ride?
I went for coverage, because it's cold, and comfort, because I had to walk through the Times Square station in them. My underwear matches my socks. Plus, everyone likes a basic boy-short.

Are Improv Everywhere events a good place to pick up guys?
Yes. There's someone here for everyone, but people are all pretty open and down for a good time. You've also got many built-in conversation starters. Come here, pantless, often?

My roommate has walked in on me and my boyfriend having sex twice now. I'm beginning to think she's doing it on purpose. How should I bring it up?
How is she walking in on you and your boyfriend? Are you having sex in the living room? She shouldn't have to accommodate naked people in shared living space. Consider staying in a private room when she's around. But if she's coming into your bedroom without knocking, that needs to stop. That's really all you have to say.

I'm a woman and my girlfriend and I are planning our first threesome. What should we do to prepare?
Be really careful as you choose your third. Think about what you all want out of the experience before you're in the bedroom together. Talk about your limits and what to do if things get lopsided or start to feel awkward.

I recently slept with a guy who was more groomed down there than I am, and he seemed grossed out by me. Do two people have to be on the same pubic hair wavelength to make it work?
Not necessarily, but I don't think it's fair for one person to groom and one person not to. Too much pubic hair is an impediment to sex. Keeping things neat down there is common courtesy.

My new girlfriend got pissed that I'm tagged in pictures with my ex-girlfriend on Facebook, especially since my ex and I are on good terms. She's convinced I must not be over the relationship. What should I do about it?
Don't delete the pictures or untag yourself. Your girlfriend's insecure and needs to respect that you and your ex were together and are now friends. She's not the only person you've ever been with – and that's a good thing.

After a drunken outing, I kissed one of my oldest friends. I don't know if he felt anything, but I know I didn't. Do you think this calls for a talk about it (with each other and our significant others), or can we just move on?
Ugh, no. Maybe send an email to your friend, if you have to. But don't even mention it to your significant other.

KeithKeith, 30

How did you choose what underwear to wear on the No Pants Subway Ride?
This is whatever underwear I was going to wear today. I’m not making any changes, nothing special.

Are Improv Everywhere events a good place to pick up girls?
I think so, but I haven’t really tried hitting on anyone yet. I probably will after this interview!

Sex with my long-term partner is getting boring. What are some easy ways to make it fun?
Porn. I like anything with Addison Rose or Tori Black. I’m a big fan.

My roommate has walked in on my boyfriend and me having sex twice now. I'm beginning to think she's doing it on purpose. How should I bring it up?
Definitely bring it up. Tell her that you’re not looking for a third strike.

I'm a woman and my girlfriend and I are planning our first threesome. What should we do to prepare?
Ask for advice from someone who’s been in one before. I’d probably say the third person should be a stranger, so there’s no drama. The third would be a guy, right? I’d hope it would be me.

The idea of making a sex tape with my boyfriend really turns me on. How can I convince him to do it?
Just tell him straight up that you want to make a sex tape, but that it would just be between you two. Then, make sure it doesn’t get out there into the world.

I recently slept with a guy who was more groomed down there than I am, and he seemed grossed out by me. Do two people have to be on the same pubic-hair wavelength to make it work?
I don’t think so, but two people should try to compromise. You shouldn’t have to completely shave if you’re used to being like a forest or vice-versa.

After a drunken outing, I kissed one of my oldest friends. I don't know if he felt anything, but I know I didn't. Do you think this calls for a talk about it (with each other and our significant others), or can we just move on?
Just forget about it. You never need to talk about drunken events.