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Wow, Todd, you have a lot of questions there. But your resident sexologist, Betty, is here to help.
Sometimes you will have sex with girls who can't make you cum. It could be you're just not turned on by your girlfriend. But ask yourself these questions. Can your girlfriend fuck for long periods of time? Or does she go for a short period of time and you're just not able to climax because you're not there? If you don't (or can't force yourself) cum, that could be the answer.
I do have to say that it's an impressive skill that you can just go and go like the Energizer Bunny. Many men can't accomplish that feat. Since you're not a fan of the quickie, you need to find a woman with the same sexual level that you have. Look for a girl who likes to go all night and/or have multiple rounds of sex (with breaks in between, of course).
If you're going to have one-night stands you need to tell women that's all there is—unless you're looking for a fuck buddy/friend with benefits. If they keep coming back for more it might be your prowess or the fact that you're concerned with them getting off too (which is a good thing). Also, I have to agree with you that sleeping with co-workers is never a good idea—there's always the gossip and awkwardness, if things go badly.
As for having sex with 2 chicks at once…this can be a good idea. Taking turns will allow you to go for extended periods of time and “get there”. Keep in mind threesomes can be tricky—they're about more than just fucking. If you and your girl decide to bring another woman into the bedroom, you will need to lay down some ground rules. Also, be sure to give your girlfriend lots of attention so she won't feel neglected.
To understand threesome etiquette, I would suggest you check out Adam & Eve's Nina Hartley's Guide to Threesomes; Two Girls & a Guy. This flick has professional porn stars Nicole Sheridan and Mika Tan (not just some cheesy 70s actors) and will make a good time better. Additionally, check out Access Instructional Media's My Three Way with Kelly Welles and Nicky Hunter to help make your fantasy a reality. You'll also want to get some sex toys so when one girl isn't servicing you, she can be pleasuring herself and staying wet. I suggest Nikki Tyler's Pleasure Vibe, the Little Lavender Clit Cuddler, or the Temptress Tiger .
Good luck!
Love, Betty |