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This is part one in a two part question. First part: Condoms.
Dear Omniphiliac, I was just wondering if you had any pointers for first-time off-the-bat condom usage. To help combat, or deal with, what a colleague of mine has called “total wiggle bullshit,” or TWB. To help the man please the lady (or man) when he’s got a big ol’ slab of desensitizing latex on his schlong and increase, for that matter, the chances of orgasm for the man himself.
Ah yes, the horrible effects of TWB can be incredibly troublesome for both partners. You two are riled up, raring to go, and you’re harder than Chinese algebra, but the moment your cockula sees that dooming latex shield it goes limp. Leaving both of you to look at each other, then look at your dick and say “WTF mate?”
There’s at least two main factors that cause TWB; physical and psychological.
Physical being you ain’t got no sensation, sucker. Or at least the sensation that you do have is nothing like the sensation of flesh on flesh (or should I say, mucous membrane on mucous membrane) loving. One way to combat this is by applying a few drops of your favorite lube inside the condom (penis side) before you put it on. This will allow for additional friction and giving you a little more sensation. However, stay the fuck away from using oil-based lubes (including olive oil you Italian stallion, you), as oil breaks down latex and that is no bueno for both parties, my friend. You can also have your partner give you a good fluffing before and during condom application. Have him or her put it on for you whilst jacking you off, or put it on with their mouth if they’re so inclined. There’s also no shame in using a cock ring. Just because you’re young and virile doesn’t mean you can’t be just a little bit harder. If your partner gives you a dirty look and asks you what you’re doing with that circular contraption, tell her or him that it ensures that the condom stays on (wink wink). Hell, get a vibrating cock ring or one with little nubbies on top to produce a greater chance of turning on your partner as well.
If you’re able to stay hard right after putting on the condom but your dick shrivels up half way through sex, try some different positions that may increase good ol’ friction. A little oral also helps, or just take a break and use another condom a few minutes later if you have to.
Psychological means your thoughtsicles are getting in the way of proper sexing. You may be one hard motherfucker but the moment you pull out that condom you think to yourself “oh jumping jehosaphat, this condom is going to suck, I’m not going to feel a damn thing.” Saying this to yourself–hopefully you’re not saying this out loud as this may scare off your sex partner–will most likely increase the chances that this will be a shitty experience. As I said, having your partner assist in putting on the condom might make this a sexy part of foreplay and you’ll be too busy thinking how hot your partner is to concern yourself with worries of latex-caused doom. This also may be anxiety-related if this was your first time with the partner. Being that you wanted to show off your sexual prowess but might have begun to feel anxious thinking that you won’t impress or please your partner. You’re not going to please everyone all the time, but you sure can try. Try not to work up this image of hot hot sex and just take it all step by step. Over thinking the matter will just bring you doom and gloom. Although this is faulty logic think of it this way, your cock needs all the blood it can take to stay hard, right? So don’t waste that blood in your brain by over thinking the minute details of your loving.
As far as your last question goes regarding increasing chances of you coming to fruition, who says that you have to cum while thrusting away inside your partner? While there is of course the appeal, and sometimes pressure to just finish off while fucking, it can also be sexy to orgasm outside of intercourse. However, your partner should get to choose where you finish off, whether it be on their body, on your hairy hairy stomach or on that tea towel your 2nd cousin gave you for Christmas a few years ago.