Casual encounter

Dearest Pud,

My boyfriend and I have been together for 3 years. He is 40 years old (I am 25) and he has never, ever, had an orgasm with a woman. He can only get himself off by masturbating in the most bizarre way (I wont go into details, I just have never seen it done this way). His physician gave him advice to see a therapist, but there is nothing mentally wrong with him. He and I both want to help him orgasm, with me.

What should we do?



Head on over to Craigslist, pick your city, and go to the “casual encounters” section. Post the following ad:

“25 year old female and closeted 40 year old gay man in denial seeks bisexual man with good oral skills.

You’ll get about 50 replies, and you’ll both have a great night!

Rock on,

6 Responses to “Casual encounter”

  1. 1 Anonymous July 1, 2006 at 9:13 pm

    awesome. I’m glad you’re using the askpud format. was an awesome site.

  2. 2 Anonymous July 2, 2006 at 1:51 am

    good advice for the little lady 🙂
    3 yrs huh?!!!

  3. 3 captain_kewl July 3, 2006 at 5:11 pm

    Dude, this is the begining of a beautiful troll

  4. 4 SleekBlackMercedes July 3, 2006 at 9:15 pm

    sexual issues need to be talked over. perhaps meeting a therapist could help.

    yeah reading some sex related articles in forums can open the mind to other possibilities.

    who knows? wish you luck lady!!!


  5. 5 Anonymous July 14, 2006 at 2:45 pm

    Tailand may have all the answers. They are very wise and have people all over the streets that help with this sort of problem.

    Works better than any theropist.

  6. 6 Anonymous February 7, 2007 at 4:16 am

    looks like someone made a film about casual encounters:

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