OK, this is for older people right?

[jackoman]

This is my first post and I'm hoping for some confidential advice. I've been around the block a few times, but need a little help.

Background. I'm 52, she's 40. We're both married but not to each other. We've totally connected intelectually over a 3 month period of chatting, emailling and phone calls. This last week, we met fact to face. Our previous conversations have not been about sex other than to briefly indicate we are not happy with current situations. This meeting was also not about sex. We talked on many subjects and it felt like we had known each other forever.

When I first saw her, all I could think is she is out of my league. I'm on the chubby side and she is proportional. She's cute, funny, long legged, and fairly hot. We have a long, friendly conversation at lunch and then sat in my car where we cuddled, kissed and touched for two hours. We would have gone to a motel except for having agreed this was a get-acquainted meeting. I also did not want to rush her and she didn't want me to think she was too easy. However, we both wanted to go further. Instead, we finally said goodbye. Riding home, I kept pinching myself to make sure I wasn't dreaming. Before saying goodbye, we decided to meet next week in a motel.

While in my car, we both kept our clothes on (mostly). Next week, there won't be any hiding my somewhat chubby body, with wrinkles, etc and lack of physical fitness. On the age related thing, I will also take a magic pill before hand. I am not dead but to last a little longer and be harder the first time and help recovering for the 2nd or third time, I will need a little help from the pill.

I don't anticipate any trouble pleasing her orally or making her feel thoroughly appreciated, etc. While I have had previous similar relationships, it has been a while and I don't want her to think I am having a heart attack when we get into regular sex. Hopefully, I won't be wheezing. I would like to lie there and let her do all the work, but I don't want to be callous. Should I tell her to remember i am not an athlete and assume she knows the age difference precludes me from running up 10 flights of stairs?

Is it a good idea to take care of her orally for as long as she can stand it and then let her take the lead? Or should I say something? If I try to be the macho man and go for it but can't finish, is that a bad time to roll on my back and tell her to climb on?

On a related note, the few conversations we've had about sex we've both indicated a desire to do oral for the other. So now, we are meeting for the explicit reason to have sex. Naturally, driving there, I'll be thinking about it and be ready to explode. Do I do the gentleman thing and make sure the lady comes first? By that time, I might not even last and go off from friction of the bed.

Or, do I indicate it would allow me to spend more time for her if she could "take the edge off" for me first?

On a related note, whether first 2nd or 3rd, when she does do me, how do I know if she will swallow? Should i ask or say something like, "will you need a towel or will there not be anything to wipe up?" My reasoning here, is I very much like to stay inside while I am coming. In fact, I want very much to feel it being milked for a while after I come. I'm guessing this is a "see what happens" scenario.

Damn, I have asked a lot of questions and hope to get at least a couple answers. Hopefully, I won't get flamed or lectured or given advice, admonitions, etc for what we are doing.

One last question related to swallowing. I've heard it will taste better if i drink pinaple juice. Is that a glass a couple hours before? A few glasses the day before or 10 gallons a day for three weeks before hand?

[a-bit-shy]

Well, I think you are asking a whole lot of someone you don't really know that well. Take it slow. Let her know you care. Don't be too pushy. Please her. Body worship her. Make her the centre of your world for that brief time you are together. Don't make this about her. And, most of all, if this isn't going to be a lasting thing, don't lead her on!

[dancingdoc2]

My recommendation is to put the same amount of time, effort, and interest into your marriage in order to make it better. Failing this, once you become single, then connect up with someone, not before.

Apparantly, you think it is OK to have a dalliance with someone; imagine what your reaction would be if you were on the other side of this and found out? Wives have a sixth sense about this so do not think you are getting away with anythng.

[learning]

I cannot agree more with the response from Doc above. So often one looks at a situation selfishly, try turning the tables!

If things are that bad at home, divorce! It really is more simple then many people make it out to be!!

[Sustayned]

I'm going to have to make it a third here. I believe that once someone has their interests up for someone else, they talk themselves out of trying to make their current situation better.
However, I'm biased in that way. No matter what, if your marriage is no good and can't be fixed, like the Doc says, divorce and once you're single you can do this all you want. How can you have any kind of relationship if it is based on sneaking around? No good ever comes of a relationship built on the misery of others.
And finally, for what it's worth, I wish I had a dollar for every time a married person said that their new fling and he/she are soul mates or really connect or whatever. I think the whole thing is disrespectful and disgusting.

[EvilEvilKitten]

I, however, understand your position.
Relax; the first time with any woman is going to be fraught. She already knows you are not an athlete. She already knows you are 12 years older than she is. She also knows you are married as is she. She's also worrying that she's not a hardbody any more. The insecurities are the same for you both - a reverent "you're magnificent!" will help there. What you now do is lead with your strongest suit. Take your time. Make her feel appreciated from the first moment to the last while also making sure that you get yours as well. Exhibit a quiet confidence and all should go well.
Good luck to you.

[wellmannered_squirrel]

Pineapple juice will not work. nothing will in fact.


As for my advice, I would plan something for the after motel time. Dinner ?


As for the divorce/marriage thing, well... I think you know what you should do by now.