Sex Advice From . . . Role-Players

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"Cosplay" is a Japanese term for “costume play,” wherein fans of anime and manga dress up as their favorite characters and attend conventions. That is where we found this week’s sex advisors.

Anna, 23
Sol Badguy from Guilty Gear

How do you nudge someone into bed without seeming too aggressive?
I’m a really aggressive person, so if they can’t handle that, then the relationship isn’t going to work out. I’m used to getting my way, so everything kind of runs on my schedule, and most guys are pretty available for sex. It hasn’t been a real issue. There’s very few guys who feel uncomfortable or feel rushed. They’re usually ready to go.

How do two people who are friends make the jump to sleeping together?
That’s complicated. I really feel that there’s a window in the friendship when that’s possible. If you know someone for, say, more than a year, you kind of missed that gap. Around the three-month mark, try to move things in that direction. If it hasn’t worked around nine months, you have to ease off.

Tips on role-playing for beginners?
That largely depends on your partner. I don’t date people who aren’t cosplayers. I’m enough into cosplay that it would just be too complicated to explain to someone why I need to work every night for eight hours and not sleep for a month before a convention. But I have dated a few people who are not as interested in cosplay as I am. You have to feel out what they’ve done with other partners. If they’re real innocent, which is sometimes nice, introduce it slowly. Find sly ways to work it in. It might be something simple like, "Oh can you wear this, oh can you do this," one element at a time. But if you have a partner who’s more experienced, just negotiate very formally.

The best locale for public sex?
I don’t go for public sex in most settings, because I always worry about minors. Like some people will have sex in Central Park and then some kid’s out there just throwing a frisbee and goes behind some bushes and ends up seeing more than they should have. You have to be really careful about that. I would say that the best place probably is at concerts, especially if there’s an over-eighteen show.

Tips for restraint sex?
I personally really like rope. It’s very flexible, it can be put to use for a lot of different purposes. A lot of aesthetic things can be done with it. I’ve picked up a little bit of Japanese rope bondage. And I weld now, so if I ever had a partner who was really into it, I guess I could take some measurements . . .

What characters and costumes should never be brought into sex?
If it takes two hours to put on the costume, it will probably take you an hour to take it off. Short skirts work well because you don’t have to remove them.


Internet porn: how much is too much?
I think the question is what kind. “Hot Asian Barely Legal” can get old really fast, but I have a high tolerance for stuff that’s in relatively good taste. I think that pornography has opened up a lot of great opportunities for artists. If you look at softcore porn, you can find a lot of reference material on human anatomy. Artist’s models make twenty-five to forty dollars an hour, and it’s so much cheaper to go to

How do you get a cosplayer to come home with you?
Be in costume. That’s really the in. Cosplay is predominantly female, which is interesting because a lot of the girls are single. Cosplayers are very trusting around each other. We all stay in the same hotel rooms and basically eat, live and sleep together. If you’re a guy cosplayer, you’re going to see every girl in your social group naked at some point. There’s a lot of costume changes.

My girlfriend doesn’t like cunnilingus. Personal preference or psychological problem?
I think the real question is why. It might be from a previous bad experience, which you guys could discuss. A lot of girls are self-conscious. I can kind of be self-conscious about that general area with a guy I haven’t been seeing that long. You see a lot of cocksucking in the media, but you don’t see a lot of cunnilingus. So I think women are often very unsure of their genitalia and about what is and isn’t acceptable. Talk to her and find out if she’s uncomfortable because she doesn’t know what you’ll think.

How can both men and women give the best head?
I think practice makes perfect. You don’t necessarily need a partner to practice: train that gag reflex down! Basically just be aware of what your partner’s reactions are. Some guys like it really neat, some guys don’t.

What can a male virgin do to ensure that his first time isn’t a travesty?
Oh, man. I’ve had some pretty bad male virgins. It helps if he knows a bit about himself: I tend to come very quickly or it takes a very long time, stuff like that. There’s a tremendous amount of social pressure of sex put on guys from the performance end of it. Girls are kind of, if they participate, great, if not, well at least they were there. The trap is that a lot of guys have preconceived notions about what sex is going to be like for them. Just let go of that, try to have a good time and make sure you remember her name.

Female ejaculation: have you experienced it and how do you make it happen?
I haven’t. I get very wet, but I don’t spray water in some sort of fantastic geyser. I hear it depends on the angle of the glands to the opening of the vagina. For me it might not be biologically possible, but I think position would probably play a big role. You’ll want to have your legs spread and breathe and tilt your pelvis until you figure it out. You can do many exercises to better your muscle wall control, give you a boost.

What are the essentials for keeping a long-term sexual relationship healthy?
Variation. Things can stagnate really quickly. I don’t mean you always have to be trying some kinky, weird thing. Sometimes you need to try some kinky n
ew things and sometimes you just need to like have normal, everyday sex. Be understanding of your partner’s schedule. I’ve had partners who, if you have sex with them, you know it’s going to be a four-hour investment, and I’m like, I have to be at work in an hour!

Male bisexuality: myth or reality?
I think it’s absolutely true! Guys are just as likely to be bisexual as females. Socially, it’s harder for males.

How do you talk your friends into group sex?
That’s really hard. If you’re having group sex, you really have to talk to everyone in the group. The real danger of a large group is that there may be too much peer pressure. But let’s say you were a guy and you wanted to get your girlfriend and another girl to have sex. The proposal would probably sound a lot better coming from your girlfriend. If you’re going for more than one guy, it would be more difficult because a lot of guys get homophobic. But if the guys know each other, the girl needs to have a sense of humor. You need to be able to tolerate a certain amount of high-fiving. A smaller group is always more workable than a smaller group. And room parties at conventions.

Chris, 22
Squall from Final Fantasy VIII

How do you nudge someone into bed without seeming too aggressive?
Wow, this is a little more in depth than I was expecting. I really don’t do that. It’s more like, “You want to bang? Okay, cool.”

How do you introduce role-playing into your sexual repertoire?
Do cosplay. You’re more likely to be alone in costume than your average couple. At a convention, for example, it’s the big icebreaker. A lot of videogame and anime characters have relationships with each other.

Tips for using restraints in bed?
I own a pair of metal handcuffs. That fuzzy shit starts shedding, and it can ruin the entire thing. So I’m down with the metal handcuffs. Even a bandana will work. But you don’t want to use a Naruto bandana, because it’s got that big metal piece in the middle. That’s just not good for anybody.

Best place for public sex?
The beach on a good night. I’m pretty flexible, so I don’t have to worry about sand in my ass.

What characters and costumes should never be brought into sex?
Anything with a lot of armor or spikes. Anything that takes fifteen minutes to get out of.

Can you introduce porn into a relationship without seeming cheesy?
I’m thinking the soft-core Skinemax stuff is the best for couples, because it’s all like — I don’t want to say well-shot, because it’s all crap — but less offensive than Spice Channel.

Internet porn: how much is too much?
When, after you save the last file, it says, “low memory: you can’t save anymore." Keep an eye on your system, delete what you don’t jack off to anymore. "Enough" depends on how much you can save.

My girlfriend doesn’t like cunnilingus: personal preference or psychological problem?
If she doesn’t like it, don’t wrack your brain about it unless you’re really into it. It’s less work for yourself.

Tips for good oral sex?
I’m sloppy when it comes to giving head. I do it until the job is done. Girls, whatever you do, don’t kiss him afterwards. Especially if you swallow! Never! It’s common sense. Go to the bathroom, wash your mouth out. Drink a glass of water. At least give me the illusion that you’ve cleaned out your mouth.

A man hasn’t had a whole lot of sexual experience, and it’s causing some performance anxiety. Does he bring it up with his partner?
Don’t bring up the anxiety. Let her know if it’s your first time. Some girls aren’t going to be too keen on it, unless they’re into doing virgins. I know a girl who’s really into going after the geekish, quiet guys because she can fuck them and they don’t know what to expect.

What are the essentials for keeping a long-term sexual relationship healthy?

Not cheating is probably one of the important ones. That tends to ruin things.

Male bisexuality: myth or reality?
It’s both. I’ve seen guys who just do it for the attention or to lure girls into a false sense of trust. Like, "Oh he’s bi, he can’t be a bad guy," and next thing they know, he’s taking them in the shitter. But there are some honest-to-God guys who can’t make a decision. A little from column A, little from column B.

How do you talk your friends into group sex?
Nothing sucks more than blowing it for a bunch of people. I’m not too big on the orgies. Threesomes here and there, but never an orgy. It’s one of those things: in the business of pleasure, don’t bring your friends into sex. When it’s just three people, do your best because girls talk a lot. Once word spreads, if you’re good, you’re a legend. If it’s bad, stick with that internet porn.

Ray, 20
Riku from Kingdom Hearts

How do you nudge someone into bed without seeming too aggressive?
Small things like taking the hand, kissing. You have to take some steps, because they’re going to wonder if you’re interested in them or not. But don’t take it too far.

How do two close friends make the jump to sleeping together?
It depends on how long you’ve been friends with that person. If you haven’t been friends with them all that long, I would just make a few jokes about it. Drop hints and make it seem a little funny. Depending on their reaction, you can keep taking it a little bit further.

Tips for using restraints in bed?
Make sure that it’s not rape. Then it’s just a matter of finding the materials.

Best place for public sex?
Obviously you can’t have it too hot or too cold. Things get numb, things get messy. I’d say beaches and parks.

Internet porn: how much is too much?
When you need to keep installing and uninstalling hard drives to keep all your porn, I think it’s time to go outside.

My girlfriend doesn’t like cunnilingus. Personal preference or psychological problem?
Well, if she doesn’t like it, she doesn’t like it. There’s nothing you can really do about it. Try and do it a little differently to make sure she enjoys herself. Other than that, you really can’t force it.

Tips for giving the best head?
For women: they call it head for a reason. You can’t just keep doing the same thing, concentrate on key parts and expect it to be fun. It just gets boring after awhile. For guys: know what you’re doing. It takes some experience, to be honest with you. Women are a lot more detailed. I find that women have a much easier time pleasuring a guy than we do for them.

What can a male virgin do to ensure his first time isn’t a travesty?
Before it even happens, there’s going to be a time when you discuss your past experience. I would not recommend lying, because if you do, she’ll expect a really great time, and when you’re horrible . . . I’ll be honest with you: my first time was horrible. It takes practice. So let her know, because then she can work with you. You’re just going to get better from there.

Female ejaculation: have you experienced it and if so, how?
I’ve never experienced it. It’s like an urban legend.

Male bisexuality: myth or fact?
I never went down that road. Some people may just do it for attention, but there’s people who do it because that’s just the way they go. I know a lot of girls who do the bisexual thing because they know a lot of guys who find that attractive. I just can’t say if it’s guys who are trying to impress girls, or that’s just their own thing.

How do you talk your friends into group sex?
I’ve never attempted that. I’m not a telepath.

Carrie, 22
Aeris from Final Fantasy VII

How do you nudge someone into bed without seeming too aggressive?
Find a medium. You shouldn’t be a jerk, and you shouldn’t be a whiner.

Tips for role-playing in the bedroom?
You don’t have to have sex to do it, you do it with foreplay, making out. You can have a bunch of different levels to it if you want. People who’ve done it a lot should give space and time to people who are inexperienced and let them grow. As a female, it makes you uncomfortable and can hurt you emotionally.

Best locale for public sex?
Somewhere dry.

What characters or costumes should never be brought into the bedroom?
Children and tentacle monsters.

Can you work porn into a relationship without seeming cheesy?
It can work if you both like it. It’s not my thing, I prefer hentai.

How do you get a cosplayer to come home with you?
Make friends with them, then tell them where you want to be with them, and make sure you’re both in agreement.

My girlfriend doesn’t like cunnilingus. Personal preference or psychological problem?
If she’s uncomfortable with it, she might not be comfortable with herself. Help her with it. But if she just doesn’t want to do it, just let it go until you know she’s ready. Forcing it will just make things worse.

What can a male virgin do to ensure that his first time isn’t a travesty?
Research, research, research. So you’re not left in the dark like, “Uh, do I touch you?”

And what should I female virgin do?
The same thing, basically. Always use protection.

A man in his late twenties hasn’t had a lot of sexual experience and it’s starting to cause performance anxiety. Should he bring it up with his partner?
It’s not uncommon. A lot of guys over twenty or even thirty can be virgins. That’s a common thing I see.

What are the essentials for keeping a long-term sexual relationship healthy?
Always tell someone if you don’t like something. And ask what they like. There’s nothing worse than not telling someone how you feel. And be silly; always have fun with each other.

Male bisexuality: myth or fact?
There are bisexual women. I’m bisexual. Why not?

Group sex: how do you talk your friends into it?
It’s not my thing really. Too many emotions right there. Too complicated. And it sounds very tiring.

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