Advice

Sex Advice From Santas

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Yomi, 40

SantaCon United Kingdom.
I’m spending Christmas with my girlfriend — at her family’s house. Any advice for sneaking in some sex without accidental walk-ins?
Sneak off to the bathroom — say you have a problem with your contact lens and need someone to give you a hand. One of my favorites is “I’ve got something in the car.”

How do I avoid awkwardness and clichés when I want to invite someone up to my apartment after a date? 
The best line I was given was, “Well, let’s see if you’re a good fuck.”

Direct. I appreciate that approach.
And it works. It was good in that it brushed all the crap to the side, and I knew what was expected of me. And to be honest, this affair lasted three years.

A friend of mine recently told me that he doesn’t enjoy receiving oral sex. Sometimes he has trouble staying aroused when it’s happening. I think he feels like a blow job is demeaning to his partner. How can he get over this hang-up?

This is a problem for a lot of men. Have a nice sensual massage, use some flavored oils, tasty little ointments, a bit of chocolate sauce. Get the person into a nice ticklish mood and then gradually proceed.

 

My partner wants me to wear a cock ring. She says it intensifies her pleasure. I want to make her happy, but imagining myself wearing a sex toy feels unnatural. Is there a way to phase out that feeling?
Let her tie you to the bed for a short while and play around. You’ll soon get used to being restrained in one way or another. Men wear belts and ties. It’s not much different from that.

I really want to have a threesome, but all of the people I’ve met that want to have threesomes are disgusting. How can I go about finding a couple of normal people for this?
The best thing: go to a gay bar and pick up a man. There are lots of men in gay bars who aren’t necessarily gay and are open-minded enough to try something like that.

A guy I’m seeing can only finish with a condom on if he takes me from behind. The fuck is all right, but I’m starting to take the lack of coming face-time personally. He does a lot to please me, so is this something I should just get over?
No. Hell no. This almost sounds like something people say here in the UK: “Nice body, but put a plastic bag over the person’s head.”

We call that a “Cleveland Brown” here. They’re a football team that has very nice uniforms, but ugly helmets.
[Laughs] I say strap the fucker to the bed and just ride him. It’s as simple as that.


Brittonie, 23

A friend of mine recently told me that he doesn’t enjoy receiving oral sex — sometimes he has trouble staying aroused when it’s happening. I think he feels like a blowjob is demeaning to his partner. How can he get over this hang-up?
The best way is just to start by exchanging oral sex, or you do it at the same time. Also have a conversation about it, try to figure out where that comes from. A lot of it probably comes from pornography. In general, when you see some porn star come all over someone’s face, it’s not hot, it’s gross.

I hooked up with a colleague at work. Now it seems to have fizzled out quite naturally, and another guy at that job is interested in me. Is it a bad idea to double-dip?
No. As long as you can keep the nookie out of the workplace and the workplace out of the sex, there should be no problem.

I really want to have a threesome, but all of the people I’ve met that want to have threesomes are disgusting. How can I go about finding a couple of normal people for this?
Well, in Boston, there’s a pretty huge polyamorous scene, with bands and specific shows you can go to. There are a lot of normal people into having threesomes who are only comfortable talking about it when they feel safe. And there’s safety in numbers. That’s really the way I would recommend doing it, because you get an idea of what these people are like, and you can find something within that circle.

When is it okay to hook up with a friend’s ex?
Depends on how good a friend it is. If it’s a really good friend, I would say you should ask them. I made the mistake of hooking up with a friend’s ex-boyfriend and it ruined our friendship. It just wasn’t worth it. It’s kind of like hooking up with your best friend. You have to weigh the consequences.

Is it appropriate to give someone a sex toy for Christmas? The best sex toy to give for Christmas?
I gave one of my friends a blow-up doll — it was more of a joke than anything else. Several years ago my friend and I exchanged gifts. I got her a clit kisser, and she got me jelly.

That’s friendship.
Yeah, she was one of the best roommates I ever had.

I’m a girl whose boyfriend is bisexual. I’m not interested in threesomes, and I prefer to be monogamous. Is there hope for our relationship?
Sure. You can either say, “Don’t make out with boys while we’re together.” Or, “I want to watch.”

Enjie, 23

courtesy of Santa Speedo Run (an all-Santa, all-Speedo road race that raises money for Children’s Hospital Boston)

How do I avoid awkwardness and clichés when I want to invite someone up to my apartment after a date?
Pretend you have something interesting in your house, and if you don’t, pretend you lost it. In any case, while she’s there, pour her a drink. There’s no way to avoid awkwardness or clichés. But most people will suspend their disbelief if they think they’re going to get some.

When you drunkenly kiss a co-worker at a holiday party, how do you save face the next day?
For the most part, pretending like it never happened works. It’s like the prerogative of women to forgive themselves anything when drunk.

When women talk dirty to me, I get so turned on that it hurts. But I feel very self-conscious when I try to respond. How can I get into dirty talk without feeling like a fraud?
Half of dating is saying unnatural things. Say whatever comes to mind and realize the other person wants to suspend their ironic sense of cliché-ism as much as you do. Otherwise, who in the hell could have sex?

A girl I’m seeing sometimes shrugs off my touch when she’s tired, ticklish, etc., leaving me unsure where she likes to be touched. What should I do?
In our society, apparently you’re not supposed to ask. It’s like in Coupling [the British sitcom on BBC America], when Jeff explains that for some reason guys are supposed to know how to operate the equipment the moment they get in. Suck it up, if you know each other, don’t worry about appearances, ask her what makes her feel good. If not, you’re kind of screwed.

When is it okay to hook up with a friend’s ex?
If it’s heat of the moment, you should always tell the friend afterward. If it’s not heat of the moment, you should always ask the friend beforehand.

I’m obsessed with someone who shot me down. I’m convinced we’re perfect for each other. How can I tell if someone is truly uninterested or if they’re playing hard to get?

No one is ever playing hard to get. If they are, to the point where you confess your undying love, that person is probably crazy. And outside of the movies, if you act like John Cusack and keep up with it, it’s not a cute romantic comedy, it’s stalking.


Jamie, 30 

Bellingham, Wash. Santacon Ringleader

My fuck buddy and I have very little to talk about, and while this wasn’t a problem at first, now it’s kind of turning me off when we’re physical. How can I get him to be more of a buddy and thus a better fuck?
Share a sex partner with that other person. Then you could reflect on what that experience was like for you both. I really want to have a threesome, but all of the people I’ve met that want to have threesomes are disgusting.

How can I go about finding a couple of normal people for this?
Lower your standards.

A guy I’m seeing can only finish with a condom on if he takes me from behind. I’m starting to take the lack of face time personally. He does a lot to please me, so is this something I should just get over?
I actually had a Santa that was like this. We lined the room with mirrors. You get the face-to-face time that you’re looking for, and it gives you the sensation of having two or three other Santas in the room, without actually having to get into multiplayer action.

I’ve gone out with a guy twice. We flirt and touch a lot and have a lot of fun, but he still hasn’t made a pass at me. Is he not interested? What should I do to make him more interested?
That’s a difficult question; a lot of people have different tastes. If it’s a man, and you’re trying to get his attention, the smartest thing to do is to grab him by the hand, whisper some dirty comments into his ear, pull him into the bathroom and give him a blowjob. You’ll find out in only a couple of minutes where you stand.

Matt, 25

West Chester, Pennsylvania, SantaCon Leader

There was a report a couple years ago about many teens choosing to lose their virginity in December because of pleasant childhood memories of the holidays. Is the “Santa Effect” bullshit?
I think it’s bullshit. Teenagers get it on any time of year. I don’t think it’s really the gift that it used to be.

How do I avoid awkwardness and clichés when I want to invite someone up to my apartment after a date?
Tell them you give a nice massage. The coffee technique is age-old; I don’t think that works anymore.

Is there such a thing as a good pick-up line?
I would say go in a Santa suit, and walk up like an idiot to any girl or guy, and you shouldn’t have a problem talking to them. That’s definitely what I’ve noticed. We’ll be in a bar with fifty Santas, and every Santa is talking to someone just cause everyone thinks it’s hilarious.

I’ve gone out with a guy twice. We flirt and touch a lot and have a lot of fun, but he still hasn’t made a pass at me. Is he not interested? What should I do to make him more interested?
No, he’s probably just shy. Really, I don’t think there’s anything you can do unless you make the first move. If he’s shy, he’ll come around in the next few dates, but if not then he’s not worth your time. But if he flirts with you and he’s not making his move, it’s probably either he’s shy or he has something else on the side.

What’s a way you can be assertive in asking someone out/winning someone over without being too aggressive?
Do something small or nice for them. They’ll start thinking about you. Leave a note on their car. If you do something just sort of nice or stupid for them, they know you’re thinking about them, and it’s leading up to asking them out, but it’s not like you’re smothering them. If you do something small like that, it will get you on their radar.

Have you ever done it with the hat on?

Nope, but maybe this is my year.