Need some advice... new to this
 

Hi guys,

I'm hoping someone can help me find some satisfaction without getting myself in trouble. I'm married and totally straight. Never so much as kissed a guy. I'm just really interested in having my ass fucked, and my wife has no interest in such a thing. I know nothing about cruising. I'm okay with anonymous, or stranger sex, but I don't think I want to do anything in a park or public place; too afraid of cops.

Any advice on how to get my virgin ass fucked?

Thanks!

It's easier than you think
 

You have two obvious choices: go to an adult book store and make a connection, or go to a gay bar and do a pickup. I'm assuming you don't have any gay friends willing to pop your anal cherry as I'm sure you would not have had to write for advice.

There are some serious considerations before you get yourself in this situation. You're married, and have broached the subject with your wife. How will she react if this becomes public later or becomes a regular thing? If you can deal with the guilt of cheating on your wife, and it is cheating whether with a woman or another guy, proceed. If not, just go buy a dildo and make believe.

Thanks for you advice!

I've gone to a gay bar twice now. I ordered a beer and than I waited, and waited, and waited... I'm not sure what I'm doing wrong. I know that I'm totally naive about this, but I'm not sure what I'm supposed to be doing to get more attention. I'm a good looking guys. So... what am I missing?

Putting the moves on at a gay bar
 

I can't really help you there. It is more a personality thing than looks. You got to look like you fit in. Nobody wants to meet the new guy, undercover cop or gay basher fears might hinder them. If the bar has a bulletin board, check it out. Even if you are not really interested in going that route, pretend to read and even jot down a number. You want to give the appearance of being on the prowl without looking desperate.

In most gay bars I have been in, you can usually strike up a conversation with someone pretty easily. Don't start off with "How big is your dick?" or "I really want to get my anal cherry busted!" Just a normal conversation about the music or the decor. After your target feels more at ease, a hand on the shoulder or covering his hand with yours for a second can signal intimacy wanted.

Before you go, make sure you have a suitable place to take your date if you get successful. Nothing more frustrating than get the juices flowing, and then standing outside the bar arguing "your place" or "mine". Don't assume that you can just do it in the dark corner, most bars have to police such action to keep from getting closed down. Cops also are aware of the gay bars and are on the lookout for male couples coming out of the bar to head into the bushes or back alley. Don't assume he will have a place without a roommate or parents. Having a place selected beforehand will also allow you to set up the room with towels, lube, dvd, or anything else to help the mood. If you get him back to your place and the action gets hot and heavy, do you really want to stop to go looking for towels, lube, condoms, etc.

If nothing else works after a time or two, drop your pants and hop up on the pool table yelling "Cherry for the taking". No, really, don't do that no matter how desperate you get. Save that for the after hours orgy after you become accepted by the bar regulars.;)

Just place an ad on craigslist.org

Direct approach
 

Hey William13-
Here's a suggestion that I've recommended to others in your situation. Forget the bars, the baths, the parks. Too iffy, and if you don't know what you're doin' (a-HEM!), you could find yourself in a mess.
Check out the escorts, in the bi-weeklies, and on-line. Yeah, you're payin' for it, but we all pay for sex one way or another, regardless of what many guys will say. If you do your homework, you should find the 'perfect fit', no pun intended. These guys know what their doin', and they'll give you exactly what you're lookin' for. They are, after all,'professionals' in their field.
I know I'll raise a firestorm of protest for this, but there's much to be said for sex workers. Look around. Be choosey. You're payin' for it, after all.
T

I have to say I fully agree. You get the talents of a pro and lots of the things that could go wrong (like seeing co-workers at a bar or baths) are taken out of this equation. Plus you can be entirely honest with the escort and I suspect you'll find they've been involved in this very situation before.

Keith