Tuesday, August 21, 2012

Disappointing hookup

The pics decorating this post are completely random with no particular source or theme.

50-ish Business Man had been sending me increasingly explicit POF messages and pictures for several months, all initiated by him.  Exciting!  The anticipation!!  Business Man was married to a man in another city but it was not an open relationship.  He claimed he didn't normally hook up.  "I'm very picky about who I have sex with."

Finally, he was to be in my town on business and proposed a hookup.   I asked to bring along Hunky 22 year old for a threesome.  I did this because Hunky and I had been looking for a threesome opportunity and partly because I wasn't sure if I'd be sexually attracted to Business Man.

We met in the lobby of the fanciest hotel in town.  He was shorter than me and quite dumpy, very quiet as we waited for Hunky to show up.  Hunky had seemed quite excited about the threesome, messaging me and Business Man several times during the day to confirm his attendance.  He was normally highly punctual and reliable, but phoned me as we waited in the lobby to say a "crisis" had happened;  he was not available.  Whatever the "crisis" was,  I thought I heard genuine regret in Hunky's voice.  

Business Man and I went to his room, had a glass of red wine and lay, fully clothed, on the bed for a very long time.  We were like two corpses side-by-side on a mortuary slab as I continued to force the conversation along.  I finally grabbed his hand and started to cuddle him while he continued to be unresponsive.  I was thinking, "Why are we here, buddy?"

Finally we shed our clothes and we made out for a while but I just wasn't feeling it.  Although I was rock hard, he never got harder than a semi which was very off-putting to me.  He was a pretty good kisser, if a a bit slobbery and with a faint whiff of bad breath.  His blowjob was so tentative that I couldn`t feel it;  I had to look down to check that he was even doing it.

Our encounter was just boring.... no aggression or sexual  interest on his part at all.  After 30 minutes, I said perhaps I should be leaving.   It was probably a relief to both of us.

What a disappointment!!  It reminded me somewhat of this recent post by Explorer Jack.
I was so bummed out buy this pathetic hookup experience!   In fact, by the next day (Sunday afternoon) I ignored the invitation of the sexy 21 year old university student to come to his apartment which we`d previously arranged.   To make matters worse, I didn`t message Sexy Student with any excuses or explanations for my no-show.

I must message him soon with an apology but I wouldn`t blame him for giving up on me.  This was the second time I`d turned him down...


  1. Although there isn't, I think there should be a bumper sticker that says, Bad Sex Happens. I've had a couple of real dogs in my past -- I think we all have -- but it's like riding a bicycle: you just have to get back in the saddle and keep on going.

    I think it would have been better if the Hunky 22-year old had been with you. You and he could have had a great time together and your exciting-as-a-flatfish hookup might actually have come to life a bit from watching.

    1. Thanks, Will. You're exactly right! I'm sure a threesome would have been fantastic! Business Man was exactly the type of man that Hunky likes the best and (I'll admit) Hunky is my favourite kind of man. There would have been plenty of opportunities for watching and joining in!

  2. Ah, they can't all be winners, eh? Hopefully the next guy will be a tad less... disinterested? :)

  3. Next time sit on his face and squeal.

  4. Actually your hookup success rate has been good. You are lucky to have done so well!

  5. that happens actually; often the reality fails to live up to the fantasy.
    Best to say 'ah well, there will be other Christmases". and move on.

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