Bro’s Girlfriend Wants Him to Wear a Vibrating Dick Ring, Plus Should You Hit on Chicks on LinkedIn?

By 11.22.13

Q: So I've been with my gf for a bit, probably had sex about ~60 times now. She says she loves the sex but she's struggling to have orgasms during sex. However, she loves oral sex and that almost always gets her to orgasm. So I plan on keeping that up, but I'm disappointed plain old sex isn't getting the job done despite our best efforts.

She mentioned that maybe I should try this vibrating cock ring that will stimulate her clit…not sure how I feel about this. I want her to be happy but feel like it will take away from the experience/intimacy and I want to be able to do it on my own/feel weird using this type of stuff. I would be willing to try but don't wanna be stuck wearing this ring for the rest of my relationship (possibly life). Thoughts?

A: Approximately 60, eh? Judging by the fact that you can still count how many times you've boned…you're new at this. It's fine. Everybody's got to learn to ride a bike at some point. So to the cock ring I say, why not? Hell, try anything once, if only for the story; and especially if she's the one bringing it up. To all sexual suggestions, you, young grasshopper, should be open and willing. Sure some things might be awkward or tickle or hurt…but you might kinda like it.

I will say its a great thing you're able to bring your lady to climax with the flick of a tongue. That's an essential skill to have and I commend you for mastering it despite having sex with her “~60 times”. But after a while that tongue of yours is gonna get pretty tired, and homegirl is gonna get bored and want the real deal. So allow this to be an opening door into the realm of your sexual experiences. Think of this cock ring as a gateway drug. A gateway drug to role play, handcuffs, outdoor sex, and orgasms. A gateway drug that only has a battery life of 25 minutes, so concern around wearing it for the rest of your life is irrelevant (but still sort of funny).

Don't think of this as taking away from the experience; think of it as adding to all of those to come in the future. 

Q: I've been going out with a girl (she's 20) for about a month and she won't have sex with me…because she's a virgin. Any thoughts on how to make it more comfortable for her when it happens(hopefully soon)? 

A: Let's not get too eager here, v-card thief. This is homegirl's de-flower-ment we're talking about- her sexual rite of passage into womanhood- so don't think for one second that she's gonna take it lightly. And unless you're in this thing for the long haul, I highly doubt your one month of dating is going to earn you rights to the chastity belt keys; especially if she's already waited this long to hand them over.
It's a task that's not impossible, but its not easy either.

Your number one task is to convince her that you're the right choice. And there's some responsibility that goes along with that. Namely, you need to not be an asshole if given the opportunity, which is inherent in making her comfortable if/when the time comes. You might recall that losing your virginity is fucking awkward, so provide as much emotional and physical support as possible during the experience, and let her know beforehand that those are your intentions.

Of course there's always the potential of creating a monster from these situations, which is to say, a stage five clinger. Be alert for any signs of extreme attachment post-penetration; and as always…wrap it up.

Q: So I work for a very large corporation.

We are currently being audited and because of this, there is a team of auditors here who are also employed by our company. 

There are four people on the team and one very hot, sort of innocent looking girl. I talked to her twice, say, 2-3 minutes which is a lifetime in a cubicle filled office building. She seemed interested: Shoulders squared to me, eyes directly looking at mine, quiet nervous replies. Simply put, she wants the D. 

Now here's the kicker. I haven't seen her at all in the past 4 days. She is only here for 2 weeks auditing my department, so she is gone for good shortly. 

After a little stalking on the google, I found her LinkedIn and her last name.

Here's the question: How creepy is it if I were to message her on LinkedIn and ask her to come out for drinks after work or get lunch? Consider that she ONLY gave me her first name(although it IS unique), her name/e-mail is not part of my company wide address book, and we only talked twice in the hallway.

Even if I were to run into her…I feel super awkward asking a girl out in front of other employees. 

Whats the move. LinkedIn message, is it creepy or is it not?

A: As far as your initial intuition goes of assuming she wants the D from two sub-five minute conversations, I say, cool your jets. And to this entire considered approach, I also ascertain the same advice. Cool, your fucking, jets, dude.
This girl is on the job. A job which happens to involve the audit of your employer so frankly, the best move seems to be to keep your distance. What happens if you guys end up in bed together and you casually leak your company's largest financial secret in post-coital conversation? Is that one sack sesh worth losing your job and possibly the foundation of your company? I understand that she's cute but for all you know, she's also a mole.

Moreover the essential move is to NOT contact her via LinkedIn. LinkedIn? Are you fucking serious? If things get serious do you think you'll propose over twitter? That is grade A stalking and her sentiments will not be otherwise. 

Your only shot at scoring a date with this girl — who by the way, may or may not know your name — is going to rely upon another chance encounter.

That's. It.

And frankly, judging by your observations of her, “quiet, nervous replies”, she may already be creeped the fuck out and taking the long route to the water cooler specifically to avoid your lingering gaze. So for that reason, and in favor of remaining off of the audit watch list I say, cool it. 

Q: I'm a freshman in college and I've already slept with 6 girls. My question is this: will girls view a guy as more attractive if they know that other girls want to hook up/are hooking up with him? Does the competition make them want the guy that much more? Or does it make the guy seem gross and unattractive? What if he plays the “I usually just have random hook-ups, but you mean more to me than that” card?

A: Touche, freshpimp. I'm pretty sure your dad told you this on the drive to college but just in case, let me reiterate: wrap it up.

Now that we've covered that point (and you're penis) it's also important to pay attention to the caliber of skank you're bumping against your bed frame.
Or since you're a freshman living in a dorm, against that prison-y brick wall directly above your “sleeping” roommate. 

The point I'm getting at here is that yes; racking up points with the ladies will often make you more appealing to others. Girls wonder what you have that makes you such a desirable conquest and their curiosity leads them to dropping their panties. But if you're strictly bringing home that girl who blacks out four nights a week and loses just as many pairs of panties in that span of time, you're losing street cred rather than gaining it. The lighthearted, “He's kind of a slut” can easily turn into “He has chlamydia” when it gets around that your targeted conquests really aren't much conquests at all. And nobody wants that.

A bad reputation, that is. Or chlamydia. 

In reference to your “but you mean more than that” card, don't play it. Even the most desperate and dense of sorostitutes will see through that transparent bullshit, and it will indubitably be included in the summary of your manwhore-ishness.

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