Ask Jack and Jill, Issue 3, Vol.2 (18+)

Ask Jack

“People in movies, magazines, gossip, are always going on about ‘oh she gives such good head.’ What’s, like … What does that even mean? What are some women doing that puts them on such a pedestal with their lovers?” – Annie

Hey Annie,

Unfortunately, there’s no straight-forward answer, for a ton of reasons. The major one being that every man likely has his own preferences. But that reality does mean a significant portion of your answer resides in the fact some women have the ability to read a man’s reaction to what she’s doing and “figure him out.” That’s what’s sexy, more so than what, specifically, she’s doing down there. I think the problem is all those Cosmo magazines telling people things like “Ten Moves to Blow His Mind!” Sure, one of those moves might blow his mind, but the other nine not so much. Some women understand that and try a few things to see what’s working, so, it’s not her “moves” but rather her ability to read a man. That and her confidence and command over us. Ultimately, it is the degree to which he is attracted to you — and how lucky he’s feeling that you’re doing that to him — that makes it mind-blowing. Also, enthusiasm goes a long way (not the faked, porno kind! That’s just unnatural and weird, we don’t expect you to act like this is the best thing that’s ever happened to you, but, a general sense it’s not a chore and we’re sharing an intimate moment is nice). There is, of course, technique. Some women, sure, they have a few tricks up their sleeve, and the more they have, the more they can try on a guy, and diversity, mixing it up, is key too. But it’s honestly got a lot to do with a natural ability to act with confidence and a connection to the task at hand. In any case, he’s lucky you’re down there, don’t go worrying too much about this.

“I’m recently out of a longterm relationship. My friends do the internet dating thing, and I kinda checked it out. There are a few people on there that I know, and would rather approach them in person instead of online. Is it weird to chat up someone you only know is single because of the dating site? Do I need to confess that, or just approach them on that site? Would they be embarrassed if I said I saw them on there? I don’t see them much in person these days so I guess I’d contact via FB otherwise. Stick to the date site?” – Bradley

Hey Bradley,
I think the time to be embarrassed about being on a dating website has come and gone. It’s a big city, outside our own tight-knit groups, and how else are we to meet a partner? So don’t worry about that. And I wouldn’t worry about how you found out the person’s single, as it’s highly unlikely they’ll ask, and not a big deal if they do. Focus on why you like this person, and the best way to present these reasons to the person. Words are your best way to win someone over, if you can use them right and mean it. If s/he’s on a dating website, s/he’s looking for someone like you to come along and change his or her life. That’s all you need to glean from the fact this person is on a dating website. Go the Facebook route, drop them a nice line, see how they’re doing, and take it from there. No need to say, “Hey saw you on a dating website. Want to date me?” Just, check in with the person on Facebook, sure, read their reaction to your reaching out to them, take it from there.

Ask Jill

“My bf won’t go down on me and I go down on him ALL THE TIME. What should I do, Jill? Any  advice? How do I make him see that he owes me for all the head I give him?” – Violet

Hi Violet,
I understand your frustration but the fact is, he owes you nothing.  Giving your boyfriend oral sex does not mean that he has to reciprocate if he’s not comfortable doing so.  There are particular sex acts that some people just aren’t into. How would you feel if he insisted on anal sex and you weren’t into it? Would you feel as if you owed it to him somehow? No, of course not. A healthy sexual relationship can be about giving and receiving but ONLY if both partners are cool with the sex acts involved. Never pressure someone into doing something they don’t want to do.  Have you talked to him about this? If not, try asking him why he doesn’t give you oral sex. It could be that perhaps he’s nervous that he won’t know what to do or perhaps he’s had a negative experience before. Talk about it with him and if oral sex is just not something he enjoys giving, you’re going to have to accept it and move on.

p.s. there’s an adult toy called The Sqweel that is basically a wheel of soft silicone tongues that spin around and simulates oral sex. If all else fails, this little toy might help.

“So, I recently started seeing this guy. He is super sweet, does such nice things for me, we laugh a lot together, he’s great. It took some time but we’ve finally started fooling around a bit. We’ve tried to have sex a few times but every time it has happened, he loses his erection. He doesn’t even seem overly interested in having sex and it’s made me uncomfortable approaching the subject as I love having sex. The couple times it’s happened, he hasn’t really offered up an explanation and I didn’t really want to pry because our relationship is somewhat fresh. What should I do?” – Lola

Hey Lola,

Pry.
If you want to have any kind of relationship with this person you need to be able to communicate with each other.  If you can’t talk about your sex life then you shouldn’t be having sex with each other.  I know it can be tough when a relationship is brand new, but it’s also a great time to get in the habit of being open with each other.  Bring the subject up, somewhere other than the bedroom in the moments after he loses his erection, so it isn’t so fresh and he isn’t mortified about it. Try doing it while you’re curled up on the sofa some time.

Your guy is probably just suffering from performance anxiety. The more times he loses his erection, the more nervous and anxious he will be the next time sex happens. He may even start to not want to have sex at all to save himself from the embarrassment. Talk to him about what’s going on and ask how you can help.  As well, heterosexual sex doesn’t always have to be about penis in vagina. There are so many other things you both can do to each other to ease the pressure on him. Just like some women need extra foreplay to become lubricated or to get “in the mood” maybe he just needs a little time to be comfortable having sex with a new partner. Being a guy can be hard sometimes. They are taught that a big, strong, erect penis symbolizes power.  So what happens when their penis doesn’t work? It can be crushing. Some men can shake it off, laugh at it. But erectile dysfunction/performance anxiety can really take its toll on a man. Be understanding  and patient until you can chat with him and find out what’s really going on.  It’s a sensitive subject but I am so glad you cared enough to ask us about it. Good luck!

“Jack” and “Jill” will answer two questions each, every second Tuesday here on TheOvercast.ca. Use the anonymous form below to ask a question of your own.

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