A few months ago I found myself in an unusual for me type of scenario and out of curiosity I thought I might throw it out to the group to see what you guys might have done, were you me.  It doesn’t have to do with our hobby per se, although does involve being away from the family.  Read on.
 
First a small bit of back story.
 
When I first got into my field over twenty years ago I had a huge crush on coworker of mine.  She was already married and while we were friends I never got any sense that she had any attraction towards me.  However, I was borderline in love with her and had she ever given me any type of signal, married or not, I would have made a move.  But alas, it was not to be.  After the birth of her second child she opted not to return to work.  This was before the days of social media and facebook, so our friendship faded, we lost touch and I would occasionally wonder what she might be up to.  I haven’t seen or heard from her in probably over 15 years.
 
Now flash forward to late last year.  I was invited to a three day industry conference held upstate and was asked to be a presenter/speaker.  It is a bit of an honor in my field and I was flattered to be asked.
 
It also meant a three days on my own away from the family.
 
I guess my presentation went well because I was suddenly very popular afterwards.  Women from all over the industry kept approaching me, offering to get me drinks at the mixers, sit with me at the meals, walk with me between sessions.  It was kind of fun.
 
A very attractive 25 year old woman seemed particularly smitten with me.  And I began to wonder if something might happen between us before the conference ended.
 
The final evening of the conference there is bit of party where everyone just lets loose, drinks, dances and has fun.  I walk into the party and who do I see, but the woman I was crazy about 20 years ago.  She sees me, bee-lines over to me and gives me a huge hug.  We are genuinely happy to see each other.  She had returned to work for a new company a few years prior and I hadn’t heard.  
 
She looked good.  Keeping in mind it is 20 years and two kids later, but she still looked really good for her age.  She’s still married but seemed disenchanted with the marriage.  She saw my presentation and seemed a bit smitten with me as well.  We’re laughing and catching up and before I know it, we’re flirting.
 
Now the 25 year old is hovering around me, pulling me away at every opportunity to talk, drink or dance.  So I’m back forth between flirting with the 25 year old and the 45 year old.  As the night is drawing to a close I realize I actually, for the first time in my life l, have a choice.  
 
I can go to the 25 year old’s room and investigate what appears to be great body. Or go to the 45 year old’s room and live out a fantasy I had 20 years ago.  
 
Now I’m not going to share what I did just yet because I want to hear what everyone else would do in the same situation.  
 
So, my brothers.  What would you have done?

I would have gone with the 45 year old and fulfilled the fantasy...

+1 eom

Let the fantasy with the 45 year old live on. Or arrange to bang her at a later time, either after you get home or at the next conference.

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Not sure if I would want to mix business partners or potential business partners with pleasure. It might give you a headache but if you don't care then I say go for it but be careful because women do talk especially the 25 year old. Some ladies can catch some type of feelings quick (same for guys) and when they don't get what they want it can get awkward but based on the position your in with you work; it seems to me your a smart man and can make your own choices ! Either way I hope you had a great night!

You don't want to have any regrets in life.

I've had several opportunities like this in the past and always chose to keep business and pleasure separate. If I was at an event like this, I would have already lined up my playtime, so would have made an appearance for appearances then excused myself to enjoy the charms of the lady I had already made plans with.

just go to your room, stare in the mirror and live out your fantasy that all women are smitten with you, and that you've made a huge mistake paying for escorts all these years.

I think the 45 year old is the obvious answer, he can fuck as many 25 year old hookers as he wants, and fucking a 25 year old co worker could be either a career or marriage ending decision.

Fucking the 45 year old will not only fulfill a decades old fantasy, but is less fraught with risk as she too is married.

I can't believe I just recommended fucking a 45 year old over a 25 year old, but please keep in mind this is only my advice to the OP, not what I would do. Everyone here knows what I would do. Hit them up for a threesome of course. lol

Forgot to put the "eom" again...

-- Modified on 3/7/2016 2:36:25 PM

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-- Modified on 3/7/2016 11:48:40 PM

Strange things can happen on business trips.  I remember being on week long one over 20 yrs. ago.  Most of our entire division was as well, and the evenings were party fests at the Bennigan's next to our hotel.  My boss (single female one year my junior) got quite drunk, and as second in command, I had to bring her back to her hotel room.  In the state she was in, she made it known beyond doubt that she wanted me to...  Well, I was sober enough to know this would not be a good career move, so I deferred.  Next day, she apologized, and was grateful I didn't take advantage.  But there are more...

A few years later, I was on a two day trip alone visiting a satellite office, and one my colleagues from my office was there on an independent trip of the same duration.  Same level, same age, but married.  I had worked with her for several years prior before we were both reassigned, and she was always flirtatious.  After the work day was over, I met her at the inadequate buffet that passed for dinner at the company pad for hotel, and we ended up going out to dinner at a real restaurant instead.  After we got back to the hotel, we parted for an hour to check up on e-mails, then she came up to my room because I had a bottle of 12 yr. Belvanie double wood.  My room also had a balcony, it was May, and nice outside.  Her flirtatiousness and the single malt lead to her spending the night...although this ultimately lead nowhere despite her divorce a year later in the long run, the sex with her was incredibly great.  I still look back and smile...

This happened before before I discovered TER and the hobby.  On future trips to the same location, a lady I met in Vegas who lived in NJ was my companion for the evening many times, and although she was only a part time provider, we were kindred spirits.  She's now retired, but the good memories remain.

As for what I would have done in your situation, I would have gone for the younger babe.  You mentioned that you had feelings for the older lady...I would have taken it more slowly with her, not tried for a one night stand.  But that's me...

Wow, thanks for responding guys!  It's interested to see the different opinions and how we all would have reacted.

Well, it turns out I ended up spending the night with the 25 year old.

Now in hindsight, I kind of regret my decision, although I wonder if I would have had regrets no matter who I had spent that particular evening with.  

As I said before, the night was drawing to a close and it was pretty clear that I had my pick of who to go back with.  Even though half of me really wanted to see what would happen with the 45 year old, I think because the 25 year old was more aggressive and, truth be told, more insistent, I ended up going back to her room.  We were barely inside her door before she had her tongue in my mouth and we were making out like high schoolers.  It was a nice night.  It wasn't the best sex I've ever had, but in lets be honest, other than professionals, since when is the first time ever great?  Anyway, I think I was fulfilling more her fantasy than she was fulfilling mine.

The next day after I left the conference and was driving home, I immediately regretted my decision.  Mostly for some of the reasons stated in this thread.  I wasn't worried that the 25 year old was going to become a problem for my career or marriage.  I just didn't get the sense she was the type to cause trouble.  Besides, She was pretty cool and we've spoken since and it wasn't awkward or anything.  I think it was a true to form one night stand.

No, I regretted it more because I think I missed my chance with the 45 year old permanently.  The stars aligned in such a way that opened up a window of opportunity that I don't think will happen again.  She looked disappointed when I said goodnight and she saw me leave with the 25 year old hanging all over me, and I saw her face which appeared to be a combination of disappointment and disgust.  I don't know when and if I'll see her again, but I'm pretty sure she wont be as in to me as she was that night.  

If only I'd had a more level head that evening.

Nice reading though... ah.... I so love great Russian Language .. we have saying for any occasion- so here is one I want to translate in to English Ж

"a streak of grey brings an old boy to his spring day"

as well as  other saying of my homeland comes to mind -  

"any toy is O.K. that keeps the baby at play "

It is always better  to be safe then to be  sorry :

You are a hobbiest.  You will always be able to find a cute 25 year old to fuck.  But getting to be with someone you actually had a crush on?  Well that is a rare opportunity that may never come again

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Hopefully, you got the contact info for the 45 year old and you can now pursue her as well, so all is not lost!