Ask GayDemon: Trapped in Paradise?

I’m about to go on our first holiday with my boyfriend. We have been together for about 9 months, so we’ve never really spent quite so much time together and I’m not sure how we will cope. Maybe I’m worrying over nothing, but do you have any tips to avoid this being a disaster in the making?
-Vexed Vacationer

Break up with him just before the vacation and go out on a single date with a new guy and invite him on vacation for your second date. He'll probably be creeped out that you're moving so fast, but if you pay for everything, he's likely to just fake it and go along with you for the vacation experience itself. Not your company.

So you can promise separate beds but then tell the hotel to make sure they actually only have a single bed in the room so then you can fuck the new guy in the middle of the night and if his self-esteem is low enough, he might just not say no.

I mean, of course he should say no to you if he doesn't want to have sex with you, but the point is, he consensually may choose not to.

Hopefully your vacation is some place remote like Easter Island where even if he got a running start away from you, there are lots of open fields and he can only get so far, especially if you're driving, or have the room key and all his stuff is in the room. So don't let him drive or have the room key.

Alternately, for whatever the planned length of your vacation together, in advance of it, lock yourselves in a tiny room for that length of time and see if you hate each other after. If you can't get off work to do that (since you would have instead planned your leave to be for your actual vacation) then just wear the novelty product Underwear Built for Two so you are forced to spend all your time together.

The thing is, you can be sick of each other even when you aren't together, so the vacation is just an opportunity to accelerate what will naturally happen in your relationship. And you can get outside of your head as to your normal roles. It may actually break open your routine of how you relate, so just let it. Let yourselves be yourselves. And make sure you both assert yourself for what you want to do within the vacation and listen to him also. And compromise.

So, yeah, maybe he wants to go shopping while you want to go to a museum. Clearly in that case, he's wrong. But basically just try to fit both in. And tell him how much you are enjoying experiencing these things with him. Also make some sort of surprise within the vacation. Maybe he eyes some item in a museum gift shop (see, shopping and museum in one, I'm a genius). So you secretly buy it for him and put it in his luggage and he finds it when he unpacks. You win 10 blowjobs, 9 from him and 1 from whomever.

Have fun! You'll be fine. And take pictures. You might break up when you get home for totally other reasons, so you'll want the memories. Or if you hate the memories, then you can enjoy deleting them. This is all called life. You don't know what will happen and that's what's interesting about it.

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