Should I hire an expensive hooker?

The problem isn't attracting such girls - the problem is that, once attracted, I get this sinking feeling that I wouldn't know what to do with one (like a dog chasing a car). This immeditately gives me pause - with the end result that what could have ended up with a trip to her place just ends up as having been a very nice evening where we both had a lot of fun.

 

I think your over thinking it. Listen to gut urges, and temper them with manners if they get out of hand.

Making a move sexually should all be pre-programmed, in much the same way we all know what to do with food, even before we're taught what food is..you just kinda know.

What complicates it is what society labels as inappropriate and appropriate, and then on top of that the emotions of embarrassment or shame.

Don't be afraid to flirt, touch, and make fun-flirty comments, just know to take two steps forward and one step back and keep going especially after you ask them point blank if they're willing, if not stop. But never feel ashamed about it.

Humans are animals after all, we just have the ability to think at a higher level than most.

 

Well, I'm pretty much resolved to hiring a hooker, and I can some some really stunning ones in my area (including pornstars) with rave reviews.

The problem is, I'm completely terrified by the idea of having sex... Yes, it's crazy, I know, but when I think of the moment where the push comes to shove, so to speak, I find the notion remarkably unsettling.

I can envisage having her own and the initial preliminaries, but envisaging the act of penetration terrifies the bejeesus out of me, and I immediately start looking for excuses not to do it (it's late and she's had too many clients so it won't be good; I'm not sure I'm feeling well enough; maybe I should drop a few more kilos and have a surgery to fix up the remaining lose skin on my belly which flaps back and forth when I do the thrust; I need up to be up really early tomorrow; I still have tons of work to get done over the weekend; etc etc etc). I then end up procrastinating (playing video games, checking the news, responding to work e-mails) until it's too late in the day to do anything.

Predictably enough, the pattern repeats the next day, making for a rather psychologically unpleasant day-to-day experience ("Today I'm gonna do it, errrr, maybe not quite today, ah come on I have better things to do, hey, isn't it expensive, ok, not today but definitely tomorrow, today I'm gonna do it."). Upon reflection, the pattern isn't too different from the opportunities I've had to have sex before but consciously refused to seal the deal due to insecurities over my lack of experience.

So, uh, any tips on working up the courage to have sex for the first time as man?

 

Have you ever had a blowjob from a woman?

 

Yes - was fun, though she wasn't the facial / swallow type, sadly.