Thursday, April 17, 2014

A sleepover with a high-powered Toronto lawyer.

My main entertainment while riding on a Toronto streetcar or bus (other than checking out the hot guys)  is to monitor the men on Grindr or Squirt and receive sporadic messages from them. This is how I met the Hungry Spaniard from my last post.

Both of these sites use a GPS system to arrange the guys by their proximity, so the profiles continually changed as I travelled across the city.

On my second day in Toronto, I was messaged by a 54 year old lawyer as I was heading from downtown to my airport hotel on the TTC.  He wasn't particularly attractive but was extremely persistent with many questions:

What are u doing in Toronto?
Are u single?
Are you a principal or vice principal? 
Do you have a lover?
Do you want to see me?
Are u free tonight?

Push, push, push.  He continued to message me sporadically throughout the week.

 I would love to get to know you better.
Just meet and chat.
But no sex guarantees
Don't want to fuck up a potential friend or lover.
But I smoke.  Is that okay?

I cancelled two hookup dudes (one at 5:30 pm and other other at 10:00 pm) and headed out to visit him at his condo in a trendy downtown neighbourhood. 

And, by the way, I had NO INTENTION of having sex with him. I found him deeply unattractive but he seemed extremely interesting and well worth a coffee date.  

The condo complex was very high-end but his apartment was messy with much clutter, stained carpeting and windows filmed with tar from the cigarette smoke.

Lawyer Dude was a bit heavy but had a charming smile and was extremely hospitable.  But something seemed to be "off" in his manner of speaking and behaviour. 

Lawyer Dude:  Do you notice something different about me?
Buddy Bear:  There's something really odd in your manner: do you have Aspergers' or something?
Lawyer Dude:  (defensively)  Why do you think I have Aspergers'?
Buddy Bear:  I'm really familiar with it:L  I've had many Aspergers students.  There's just something really weird about the way you're speaking.
Lawyer Dude:  I smoked a joint just before you came in.
Buddy Bear:  Really?
Laywer Dude:  Yes, I was really anxious about meeting you.
Buddy Bear:   Hmmmmmm

What followed was the most interesting gay conversations I've ever had which lasted over five hours.  During this time, he provided me with some amazing insights about my own gay development and behaviour which I found highly insightful and accurate.

He told me his complicated story:  many years of gay denial, an overbearing, Jewish mother, career and financial success, marriage at 28 to a Jewish bisexual woman with whom he enjoyed M-F-M-F foursomes and their seven rounds of unsuccessful IVF treatments.

He and his wife eventually divorced and he's since had two LTRs with men but was presently single and looking for a boyfriend, rather desperately I thought.  He didn't believe in gay marriage and thought it was impossible for men to be monogamus.

Throughout, he was extremely attentive, bringing me coffee and sweets, later a beer and then ordered a meal for me when he found out I hadn't eaten in eight hours. I called him the ultimate Jewish Mama.

He was intelligent, charming, perceptive and very funny.  I was starting to find him rather cute, sexy even.  

Then after several hours, he stood up and announced:  "All my friends know this about me, even my women friends;  I'm very comfortable with nudity" and proceeded to take off his clothes.  OMFG!  Toothpick arms and legs and an enormous beach-ball sized belly.  But the worst part was his ass which was literally not there;  it was just a wrinkled pucker of skin.  I've never seen anything so deeply unattractive in my life, ever!   I had to avert my eyes.

I said:  "I grew up in a Finnish family where we had fully naked family saunas several times a week.  My favourite place to go in Toronto is Hanlan's Point Nude Beach.  NO ONE is more comfortable with nudity than me.  But this is just too fucked up."  So he put on a robe.

(this story will be continued on my next post on Saturday morning)


  1. Eeeewwww! I might not want to read more of this! LOL

    1. Don't worry! The wrinkled, puckered ass was the worst part of the story!

    2. Whew! And read part two as you saw. I forgot you said you want to experience it all and you did. So you are in the right path! Once again I applaud you! You are an amazing man! I hope every closet case is reading your blog. And those coming out. Hugs

  2. OMFG! he's pushy cause he's a lawyer. the sight of his apartment alone would make me hurl and leave. this is not a good hookup scene; oy!

    1. Yes, I've discovered that lawyers can be pushy. Despite the state of the apartment, he was an extremely interesting person and we had a lively conversation.

      But boyfriend material, he ain't!

  3. OMG! This is surreal! I'm not sure I could have stood the usual stench of a heavily smoked up apartment, but otherwise, I can deal with a lot, and if the conversation was good, etc., then OK! Strip if you must!

    Peace <3

    1. I could handle the smoking, barely,because the balcony door was open.. But I could NOT deal with his nudity. ;-)

    2. I guess I am used to it, having spent a lot of time in clothing optional areas where many of us simply aren't "attractive", and the only smoke blows away, or is intentionally inhaled ;-).

  4. I'm glad to see you keeping it real by posting the bad with the "OMG! He was so hot and young and hung and a great kisser!" posts. ;) I'm am curious as to your motivation to cancel two, presumably, much hotter hookups for this guy. Your hookups usually include a lot of talk but maybe you had a different kind of hunger? Maybe you were just "drained."

    1. Hi Sean! I don't only post about my hottest hookups. I have posted numerous times about disastrous ones such as "The Worse Threesome Ever." Having said that, the vast majority of my hookups have been very positive.

      One guy I cancelled was a early 40-ish married guy with whom I had hooked up last summer. He was not particularly attractive and was quite inexperienced. He was very passionate and was desperately hungry for man-on-man action. That is very hot! I've somewhat moved beyond hooking up with middle-aged married men so I cancelled him, but with some regret.

      I cancelled the other guy without regret. He was a mid -40s black dude (who in fact, came to visit me the next day.) He described himself as "chubby" but I'm finding myself less and less attracted to overweight guys as he turned out to be.

      Lawyer Dude was extremely persistent and we had extensive chat conversations for five days. He seemed (and in real life, was), dynamic, interesting, experienced, funny, fairly rich, worldly and a bit of a "mover and shaker" on the provincial and national scene.

      So in the end, he was a person I really wanted to meet: in my small town life, I just never move in those sorts of circles.

      But I went there with a plan NOT to hook up and in the end, we did not hook up. I am really not attracted to overweight older guys and given our relative imbalance of power, I really didn't want to go there to be treated like some booty call.

      In the end, he was perfectly respectful of my decision not to have sex with him.

  5. You never fail to amaze me with the lengths you are willing to go in exploring the gay experience.

    1. You're funny! Yes, it is a plan that I want to experience it ALL!... rather, experience most things. I won't be trying fisting anytime.

  6. I am sitting here naked....Looking at the two action photos. how my penis is aroused too.....

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