A familiar dilemma - GG story

[suckseed]

I ran an ad on craigslist a few days ago under casual encounters, men seeking women. My second one ever. I said I was looking for someone like myself, busy but wanting an ongoing casual thing with someone nice. I got back a response from a woman who is very outgoing and sexually uninhibited. She's divorced and has a daughter, elementary school age, that spends half her week with the father, and we were both on the same page about not getting together when the kid's around, so I know she's a good mother. She seems really sweet, intelligent, but has worked sporadically for the past year, is financially struggling, and has not been treated with much kindness by the men she has met. She sort of looks like Joan Allen, nice, but not my favorite. Mid thirties.
We have been emailing and IMing for the past 2-3 days, and had phone sex last night. This woman is multi-orgasmic and wants to know if, among other things, I've ever had a strap-on in me and gotten a blowjob at the same time! The thing is this. She keeps saying how she can't believe how sweet I am. I've just been honest on the phone about where I'm at in life and what I'm looking for. I've made it clear I'm neither rich nor looking to be in a serious relationship. But I think this woman will fall for me. It's been a long time for both of us since there's been a relationship of any duration. I want her, and I'm not opposed to taking her out and showing her a good time. But part of me thinks it would be cruel to enter into this knowing it will end. And I want to know what you guys think. I know this is off topic, but it would be worse at a guitar forum. Come to think of it, I'm sure many guys could relate there too.

[Youngmc]

that strap-on blowjob thing would have been enough to sell me, go for it what do u have to lose

[needsum]

all you can do is be honest--it'll be better for you in the long run. If you fuck and chuck her, you could be on the receiving end of one hell of a pshycho bitch who will make you miserable. And, you seem to be the kind of guy who actually gives a crap about her feelings, so I bet you'll be feeling pretty lousy about it anyway.

If you just tell her the truth, that you're attracted to her and are interested in having a good time, but do not want to let it get carried away and head into something too serious and committed, she may appreciate you much more for it, whether or not she sticks around. She'll know you're not just trying to use her up and spit her out. At least you give her the option of leaving without suffering the guilt of fucking her over.

[specialk]

I ran an ad on craigslist a few days ago under casual encounters, men seeking women. My second one ever. I said I was looking for someone like myself, busy but wanting an ongoing casual thing with someone nice. I got back a response from a woman who is very outgoing and sexually uninhibited. She's divorced and has a daughter, elementary school age, that spends half her week with the father, and we were both on the same page about not getting together when the kid's around, so I know she's a good mother. She seems really sweet, intelligent, but has worked sporadically for the past year, is financially struggling, and has not been treated with much kindness by the men she has met. She sort of looks like Joan Allen, nice, but not my favorite. Mid thirties.
We have been emailing and IMing for the past 2-3 days, and had phone sex last night. This woman is multi-orgasmic and wants to know if, among other things, I've ever had a strap-on in me and gotten a blowjob at the same time! The thing is this. She keeps saying how she can't believe how sweet I am. I've just been honest on the phone about where I'm at in life and what I'm looking for. I've made it clear I'm neither rich nor looking to be in a serious relationship. But I think this woman will fall for me. It's been a long time for both of us since there's been a relationship of any duration. I want her, and I'm not opposed to taking her out and showing her a good time. But part of me thinks it would be cruel to enter into this knowing it will end. And I want to know what you guys think. I know this is off topic, but it would be worse at a guitar forum. Come to think of it, I'm sure many guys could relate there too.

I think your suffering from a dose of maturity. Happens sooner or later to most guys. Who wants to get a phone call or email, after the a few rounds of sex followed by the big dump? That will get your guilt meter peggin' a 10. When it's the other way around, girl dumps guy, for some reason it's not too a problem........NEXT!!!

Best thing to do is lay your cards on the table, let her know where she stands, remind her if it gets out of hand, and see how she goes..er blows...whatever. Maybe you'll have a change of heart yourself, stranger things have been known to happen. Good luck!

[ezed]

She sort of looks like Joan Allen, nice, but not my favorite.
But part of me thinks it would be cruel to enter into this knowing it will end.

Opinions are like assholes, everyone has one. And there are a number of people here who think I am one. So here is my opinion.
Written comments don't embodied your entire thought process. But the above quoted comments are the most telling. I think you answered your own question.

The fact that, to date, you have not followed your dick and instead followed your conscience confirms it. The fact that you're asking us seals it.

You already know what is right but you'd still like to tap her. Although, she's not an escort, the tap is still going to cost you someway, somehow.

And since I like you because your posts tend to be sincere, I'll risk the slings and arrows and state the following:

Though you honestly told her your feelings, and what your looking for, the vast, vast majority of woman truly believe they can change that and have you see it their way. And ultimately, you won't, and then you pay.

[Quinn]

Though you honestly told her your feelings, and what your looking for, the vast, vast majority of woman truly believe they can change that and have you see it their way. And ultimately, you won't, and then you pay.

Co-sign....

-Quinn

[seamonkey]

Here are a few more things to consider:

Has she spent enough time grieving the loss of the marriage in order to sort things out enough to maintain the boundaries and expectations you want? People often think they only want sex so as to avoid more loss, but they're really trying to replace what they just lost.

Has she ever had a sexual relationship like the one you two are discussing? There's always a first time, but understanding her sexual history can give you some idea about how well she can handle this one.

Yes, I used to be a therapist.

Good luck.

[hondarobot]

Heh, just keep this in mind, always (and once it starts they never let it end, and it's just not worth the effort on your part):

[peggygee]

Here are a few more things to consider:

Has she spent enough time grieving the loss of the marriage in order to sort things out enough to maintain the boundaries and expectations you want? People often think they only want sex so as to avoid more loss, but they're really trying to replace what they just lost.

Has she ever had a sexual relationship like the one you two are discussing? There's always a first time, but understanding her sexual history can give you some idea about how well she can handle this one.

Yes, I used to be a therapist.

Good luck.

Suckseed,

I am going to tell you this because you seem like a fairly decent guy, I like the 'cut of your jib'.

For the most part women just aren't wired the same way men are. We may say that we are cool with the whole friends with benefits thing, but in actuality a lot of us would like to settle in with a decent guy.

For me, if I meet an intelligent man, good sense of humor, is good to me, and my child, well I start to mentally hyphenate our names, and pick out China patterns.

Compound that with him hitting the 'A through G' spots, and having a great sexual chemistry, and yeah, you might have the makings of a real life 'Fatal Attraction' - watch your rabbit - Doc .

So, if you still want to procede against the sage advice of counsel, then I would fully and clearly state your intentions.

And try not to make her have too many orgasms, that kinda shit really fucks with our rational thinking.

[suckseed]

Thanks to all of you. I just wrote to her and told her I couldn't in good conscience become involved. I really get the sense that she's bringing in men to help support her with promises of freaky sex. She admitted to me that she just broke things off with a man who paid her rent last month. Plus she's been fired from her last three jobs. It's so weird - she doesn't seem like a whackjob in terms of how she speaks or writes - it's the stories she tells, and her tendency to see herself as blameless vs. the cruel ex and former employers. You'd think someone would know to keep that stuff to themselves.
Like my man who always makes me laugh Ezed said, I knew the answer but wish I didn't. Can anyone relate to being involved with the wrong person for the sex?
Oh, and the other main interesting woman who I've been corresponding with? Get this: Master's degree, works for the city as a social worker, very well put together, seriously she wouldn't be out of place on the set of Friends, (not that I watch a lot of tv ), wants very kinky sex. OK, ya got me! Wrong! Turns out she can only cum after being slapped around, because she was traumatized by two assholes when she was a 16 year old virgin. So I went looking for a fun lover, and ended up finding two deeply troubled women that I now am bummed out about and feeling sorry for.
But compared to them, I feel like I've got my act together!