How should I propose going from “friends” to “friends-with-benefits”?
Firstly, gauge both general and specific interest: figure out if your friend is generally interested in having a friend with benefits, and if your friend is specifically interested in you. If you have one but not the other, you have a recipe for disaster.
It varies case by case, but for the most part, getting the general idea just means having a theoretical conversation about no-strings sex. Maybe the only benefit they want from you is your Netflix account.
There are a few different ways to gauge specific interest, but I prefer directness because that sets you up for actually making this friends-with-benefits thing happen, and you’ll both forget about it pretty quickly if they’re just not into you sexually.
Oh — be prepared for that. Don’t get offended, don’t dwell and you’ll have minimal friendship damage.
Ask about their type, and if you’d theoretically fit that type. You can be subtle. For example, let’s say that you’re wingmanning for the night, and you want to make sure to look for the right type of people.
If your friend is generally interested in no-strings sex, and is specifically attracted to you, don’t stress: you’ve got this. Create a situation where you’re alone together and chill — studying, watching sports, baking cookies together, anything near your/their bedroom. Talk in theoretical terms about why you’d want this type of relationship: it’s hard to pick up chicks, you aren’t ready for a girlfriend, but good Lord, your balls are blue. (Or switch the gonads, whatever, this is pretty much the same whatever your gender.) Ideally, your friend either cottons on or agrees with you, and you can just straight-up propose no-strings sex with them. Boom. Done. Tap that.
P.S.: If you are truly crushed by their rejection, then you have feelings for this person beyond horniness and friendship, and you need to figure those out.
How soon do guys start picturing a girl naked after meeting her?
Meeting her isn’t necessary. A Facebook picture on his friend’s phone will suffice.
Hey, so I really think there should be an article about anal. What are the supplies I need beforehand? What are some anal-related foreplay strategies I can engage in leading up to the big thing? How do I do it so it doesn’t hurt? Do I need a butt plug? Does my boyfriend need a butt plug? What is a butt plug? Stuff like that please.
I have a limit on my word count, so I can’t answer this as thoroughly as I want, but there were a lot of questions about anal (get freaky!), so I wanted to at least scratch the surface. Send in the questions you still have after reading….
The Captain’s Four Rules for Anal Sex
1. Don’t Brokeback this shindig. So in the film “Brokeback Mountain,” these two guys have sex in a tent without prep or lube.
Don’t do that.
Use MORE LUBE (water-based lube, reapply often, or silicone lube, but not with a silicone sex toy) than you think you need, and make sure the person taking it is really relaxed.
Having an orgasm first helps, and so does taking anal step by step. Maybe the first time you try you’ll only get up to fingers, and that’s okay. Anticipation makes it more fun.
2. Deliver more than your package. That is to say, there’s more to anal than penetration, and all of the “more” that I’m about to list can also work as awesome foreplay. Rimming, fingering during oral, inter-gluteal sex (the “booby banging” of ass sex), butt plugs, spanking, etc.
3. Bend over, boyfriend. The prostate is a very cool part of a dude’s body, and it’s also boring and dumb to assume that only girls like being screwed. The “Bend Over Boyfriend” is an actual type of strap-on. I know, how weird is that?
4. Don’t insist. Some people just plain aren’t into butt sex, which is okay. Everyone’s into different stuff.
On the other hand, if they’re just worried or embarrassed, try some of the foreplay/penetration alternatives in rule two and work up to it.
Is sending a one-night stand 600 emails over one weekend acceptable? Or am I being too frontish?
If by “frontish” you mean “possibly clinically insane,” yes.
There were a few submitted questions that I hoped, for the sake of my sanity and also the world, were just people messing with me, and this is one of them, but just in case it isn’t — no, that is definitely not acceptable. In general, I’d say that text messages or Facebook are preferable to email because they’re more casual, and that a limit to two contacts is a hard-and-fast limit.