Fuck me.

it is better to get that squared away early on than have her realize it after you've tried to live a lie.

You do both yourself and her a favor that way.

Has honesty ever set you free?
At what cost?

I don't recall the specifics...but it was similar.

At first make only vague statements like, "I've been a very bad boy." See how she responds.  If her eyes start to twinkle and she says, "Me too!" you've got yourself a winner.
Just don't tell her about me and your mom

dabbled as escorts?  If she doesn't say much, then you ask her if she ever considered it?  Sooner or later you will need to fess up.

What anyone does prior to getting involved with someone else is really none of that persons business.

You really are a Dr. Who nerd.

Life isn't always so logical. You know?
You definitely work with numbers..

Tell this one that you fuck hookers....nothing but upside!

Posted By: TheHoundOfCullin

Life isn't always so logical. You know?  
 You definitely work with numbers..

I agree with Dr Who. Anything you say, can and is often used against you at some point.

no ones perfect,  
ask her out to a upscale dinner and get to know her.  
show genuine interest in her life.  

If the real reason is to clear your conscience, it's not a good idea as you really only might hurt the one you tell.  

A response would depend on how are the relationship has gone.  In general, I would say no. Here is why. In relationships we trip over ourselves. Does not knowing cause her harm? If no harm, that would be a reason to not tell her.  Was it really fucked up shit or just in your mind?  Is it continuing or in the past?  Hound, a thought that it took me a long, long, time to learn - "only a fool trips over something that is behind him".  Eyes forward and good luck.

I bring up various topics during our dates and if the date sounds conservative and not cool with such things, I act more conservative.  

suggest you stuff her pussy in your face to save yourself lol! Women can be fickle and no matter how cool with shit they may seem she will hold it against you at some point. Just stay cool and a little mystery is a good thing!

but it beats the alternative sometimes which is the freedom of lies and deception.

The gist of the problem is as old as mankind:

Nobly bear the burden of truth in all its horror, or wrap ourselves in deception while riding the proverbial wheelbarrow to ruination.

On balance both paths have their plusses and minuses.  The trick of living is picking which one to ride with and knowing when to switch.

As with many things in life, timing is everything.

Those with successful timing are the winners.  Those without, not so much.

Otherwise your dad Inicky will miss you. This way you are virtually guaranteed to be back here in a matter of hours, right after she tells you what a sick fucker you are and to get the hell out of her life.

But seriously, why would you volunteer to tell her all about TER, you fucking hookers, and every sick detail about your sex life, especially if she's not asking? If she asks, that's different. Speaking strictly for myself, I am too lazy to live a lie, (I still don't know how you married guys do it) but telling the truth is one thing, making yourself out to be sex perv is another. Do you really think that I brag to the civvie chicks in my life that I have been with hundreds of civvies and thousands of pros in my lifetime? Even the hookers here on TER are put off a bit by those numbers, I might be honest, but I do know how to "sugarcoat" my numbers when I don't want to have a woman go running out the door screaming at the top of her lungs that she never wants to see me again.

You may think you're like minded, she may think otherwise. Especially if she reads into it too much.

I can fuck up a relationship in tons of other ways too.
It's my specialty

It's a Boy Scout thing.