Wednesday, February 29, 2012

Rode hard and put away wet.
Yesterday (Tuesday) was one of my most exhausting days ever!  Here's how it went down:

  1. At 6:15, boarded a plane to Toronto.
  2. Arrived just in time for an  appointment at Canada's leading cancer centre, the Princess Margaret Hospital.  I've been referred there for a consultation about the removal of some wisdom teeth.   This simple procedure was complicated by possible radioosteonecrosis of my jaw caused by radiation treatments for cancer.  I blogged about this earlier.  
  3.  A decision was made to remove the teeth using conventional methods.  By noon,  left the cancer centre minus three teeth, but with a frozen mouth and a supply of Tylenol 3s with codeine.
  5. Spent five hours hitting my favourite Toronto spots such as Chinatown (hot & sour soup!), Queen Street West  (the coolest consignment shops), Church Street gay village (amongst my peeps!),  the newly-renovated Toronto Reference Library (spectacular!) and the Art Gallery of Ontario.
  6. My favourite male strip club, Remington's,  opened its doors at 5:00 pm.   I finally relaxed, drank a couple of draft beer (mixed with pain meds.... naughty!!) and looked at the hairless boys (meh!) and sexy men (woof!  made my cock hard!) peeling out of their sexy undies and wiggling their cocks around.  What a pleasant way to spend several hours!   I'll report on this in a future post.
  7. At 8:30 pm, back on the plane, arriving home at 11:30 pm.
  8. At 12:00 pm, back at my waterfront home where my special guy was waiting for me.  Our... er... reunion begins.
  9.  From 2:00 - 7:00 am (today), we slept naked, cuddled together in the cozy three quarter bed,  me spooning him, him spooning, me or facing each other with limbs entwined.  Total bliss!
  10. At 7:00 an, wake up to face a busy day at work.  Whew!

Monday, February 27, 2012

A texting "oops"

 My daughter knows ....... Two weeks ago, I was texting a sweet bedtime note to my special guy.  Unfortunately, I was  in a darkened room and I'd misplaced my reading glasses.  After I pressed "send", I realized to my horror that I'd sent the text to my 17 year-old daughter!   Oops!!

My daughter texted me back, "Dad, you sent the text to the wrong person ... obviously."   The next time we met, I said to her, "I guess you figured this out already, but I'm seeing someone........ *long pause* .....  She said, "I see."

I continued, "It's time for me to find for some happiness.  I deserve it.  He makes me feel very special .... and I haven't felt this way in a very, very long time." 

She said, "That's good.  You deserve it."   She then asked a few questions:

"What's his name?"    I answered with his actual first name.

"How long have you been seeing each other?"   I lied, "A couple of months."   (actually, it's been five weeks)

"Where did you meet?" .... I said that he was related to a work colleague.  That is the truth, but we actually met on an online gay hookup site.  I couldn't tell my daughter that!

"How old is he?"   I said he was a couple of years older than me and that he has four adult children, all out of the house.  At that she laughed and said, "Oh, my!"

Then I said, "I would never ask to to keep a secret from your mother, but I'm not planning on telling her about this right now.  Mom is having a tough time coping with everything as it is."  My daughter agreed, "I think it would be better if Mom doesn't find out about this."   Another milestone in my gay journey has been crossed.... and this one wasn't hard at all!

The next Sunday,  I tidied myself up as best I could and told my daughter that I was having lunch with my friend.   "Oooo!  Lunch!  Where?"  I named a fancy hotel in town.  "Ooo!  Fancy!!" I gave hear a kiss on the cheek and headed out the door.

My daughter stopped me in my tracks, "Oh, Dad?"


"Your breath smells nice!"

Sooooo embarrassing!

Saturday, February 25, 2012

Heading home

First of all, a couple of hot guy + cute dog pictures for Sean's Dogably Pawfect Saturday from

The other two pics were taken in the western Canadian city which we visited.  Which city we're in? I'm betting that no one will get it unless they actually live in western Canada. We'll boarding the bus soon for the long, long drive home with all 45 teenagers accounted for. Another successful, exhausting trip!

In the third pic, I am admiring the cock and balls on 2.5 ton bronze life-sized statue of a North American bison. (it's not a buffalo!!) I texted my special guy to say that looking at this statue reminded me of him. (LOL)

There was no gay fun on this trip at all; NONE! Given our gruelling schedule, the large number of young people involved and the spread-out nature of the city, it was impossible for me to sneak away. But there was eye-candy galore; lots of hot men, both young and middle-aged. Woot!

I am most looking forward to seeing my kids again when I get home;  at least I can count on my daughter. My son has cancelled out on the last couple of times he should have stayed at my house and I'm finding it very distressing. My wife said, "He just needs time." Probably sensible advice, something I don't always receive from her.

My gay slut phase is full steam ahead and while away, I've received messages from three guys I've been with, each wanting to arrange "round two" of our play dates, one request to go out as platonic friends and several messages from new guys, aged 22 to 55. And this doesn't include an arrangement for a sleepover with my regular guy on Monday.

While I am pleased to have some "satisfied" customers, I'm finding it impossible to balance the demands of work, home, having my kids with me half of the time and having all these guys wanting to be with me.  Being a gay slut is a full-time job by itself.  I'm not kidding! Something's gotta give!

Wednesday, February 22, 2012


This post was prepared earlier and was posted using a timer because I am on yet another trip as a chaperone.  This time, I'm with two other adults in charge of 45 teenagers, ages 16 to 18.  We will be spending about 20 hours on a bus during a four day trip to a big city, but not the same one  as my last trip.     Woo-hoo!

So, this will be an "eye-candy only" post featuring that most elusive of sightings, the VPL  or visible penis line showing a nice cock head outline.  All pictures are from Enjoy!

Monday, February 20, 2012

Flaky Twenty-Somethings

All pictures from hotyoungguys.

I have a profile on three hookup sites:, and   By far the nicest and most normal guys have been found on, probably because a full face picture is required on every profile.  Plenty of Fish has been very productive for me but I still find to be a very scary place.... too many profile pictures of cocks and assholes.

On, about half of the messages I receive are from guys in their 20s. Many of these list on their profiles "Seeking a Woman" and claim to have "no experience" with men but want to experiment or "learn together."

I still can't imagine what a hot young man (and they're all hot!) would want with a guy who is 20 to 30 years older, but I've stopped questioning this. I'd never hook up with a guy in his 70s, or even 60s.   I think the young 'uns find the idea of a mature yet inexperienced man somehow appealing and often mention my promise of "absolute discretion."

Some of these 20ish guys will start a chat with me. When asked to explain this age preference, they respond:

"I like men, not boys."

"Age is just a number."

"Don't care how old you are. U R hot."

"I'm not out so I can't hook up with anyone my age in case they know me or know someone who knows me."

While I am mainly interested in my guys my age, I still cannot resist the lure of a young man, as unreliable as they are.  Online, young men are much more eager to show their hard cocks while on a webcam chat.  I never ask to see their cocks;  they do this on their own.

Recently, a beautiful, tall, slim 22 year old and I were were webcam chatting and then he stood up and started to unbutton his jeans ("Oh my God, what is he doing??") to reveal a beautiful average-sized, rock-hard cock and a pair  of low hangers.   Wow!  He offered to show me his asshole, to which I responded, "I don't want to see it!   Ick!".  He flashed a sweet smile at that.

When asked to show my cock online, I responded, "Forget it, buddy, I'm not showing you my cock.  Trust me, I have one.  If we meet in person, you'll see it.  It's average-sized or a bit bigger, decent girth, smooth, big mushroom head...  "

Other than my sweet encounter with the 22 year old aboriginal young man, the majority of the 20ish men online have flaked out;  they either abruptly stop chatting or stop responding to messages in a conversational string which they've been pushing along.   I know it's not a question of me seeming needy or over-eager;  I feign disinterest and am minimalist in my chats with them. 

During a very enjoyable video cam chat two nights ago, the sweet, slim 22 year old mentioned above (he of the beautiful cock and low-hangers)  was aggressively seeking a hookup with me, push, push, push.   I agreed to meet him at a doughnut shop the next day at 7:00 pm.  I showed up on time, and of course, he didn't show up   I left after twenty minutes.

I was a bit surprised at this no-show since he initiated the whole arrangement so decisively, but I wasn't entirely disappointed.  I was still very tired and little sore from my other two hookups earlier in the week.   No regrets:  I truly enjoyed my webcam chat with him and it was his issue that he decided not to take it to the next step.

Saturday, February 18, 2012

Prostate massage + hand job = cum

For Sean`s Dogably Pawfect Saturday, here is a cute guy - cute dog pic from cuteboyswithdogs.

The day after my bottoming success, I had coffee with with a 52 year old IT nerd who I`d chatted with on  Unlike all the closeted, married guys or twenty-something flakes I'd been chatting with, he was the first really experienced gay guy I`d met online. We arranged a  hookup for the next day.

As I drove to his house, I wondered, "Why am I doing this?"... but summoned up the courage to continue. I was on my quest for the Holy Grail... an experienced gay guy who knew his way around a man's body and could teach me a thing or two about gay sex.   Despite all my hookup success, I still hadn't cum in the presence of another man and I was deeply distressed about this.

Bruce was very nice but not particularly attractive and, despite thirty minutes of passionate kissing and naked full body contact (two of my most favourite things!), my cock was a limp as yesterday's lettuce.  I just wasn't feeling it ... it was so mechanical!

He took his role as my mentor to gay sex very seriously and we discussed the possibilities to get me over my mental "not cumming" barrier.  We had a very long talk about my sexual history and I began to see what a sweet, compassionate man he really was.  He made me lock my eyes with his as we resumed our activities ... to deepen our emotional connection.  I found this very difficult to do.  Suddenly, our encounter "clicked"  and began to feel some passion in  our encounter.

I agreed to a prostate massage / hand job combo.  He inserted a well-lubed finger while doing a hand job with the other.  Such was his skill and gentleness that I had to ask him if he was at my prostate yet.  After some time, I felt shivers, then waves of trembling from my head to my toes with much involuntary writhing and moaning from me.  Fantastic!

Afterwards, he told me that I was "on the edge" for about two minutes and could feel my cock and prostate in spasms, ready to squirt.  Then, suddenly, everything stopped. I'd lost the edge. 

I finished myself off in about 20 seconds while he continued the prostate massage.  It was insanely intimate.   I'd had my first orgasm with another man.... a gusher!... incredibly intense.

He had a few very interesting observations about me:
1.  I needed an emotional attachment with a guy to have sex with him.  It was only after our intimate conversation that I truly began to 'get into' our encounter.

2.  He declared me a "true bottom" and said that he pushed his finger only half way in... and that during the prostate massage, I was rhythmically pushing my prostate onto his finger.  He said it was like my prostate was yearning for his touch.

3.  I craved and enjoyed kissing and full body cuddling, the closer and tighter the better.

4.  He said of all the hundred or more guys he's been with, not one had his mind "shut down" his orgasm like mine did.   He said  (and I agreed with his insight) that I still must be carrying a great deal of guilt about having sex with men.  Although I was physically capable of having an orgasm, my mind was a barrier which was not allowing it to happen.

5.  He was certain that I had now overcome my mental barrier to gay sex... (I hope!)

Afterwards, I told him I'd feel selfish if I didn't reciprocate, so we agreed that I'd give him a hand job.   I decided not to do a prostate massage.... I'd had enough learning for one night! 

Much to my surprise, giving him a hand job was the hottest thing ever and I got rock hard again,  harder than ever, despite having just cum.  He held onto my cock while I jerked him off.   He provided much instruction as to what worked for him and with much moaning and writhing, he came. I felt like a sexual superstar!

I'm thinking that I will visit my new friend sometime soon for my next lesson at the Gay Sex University.

Thursday, February 16, 2012

Bottoming Success (NSFW)

All pics are from

Sorry for the lack of posting! I've been at my waterfront house where I've cancelled internet service for the winter.  It was an exciting and memorable Valentine's Day, that's for sure!   Spending about 14 hours in bed with a special guy was the sweetest, most intimate thing ever!  My first gay sleepover date!

It was the emotional connection was the most special thing and having enough of a shared history to know which sexual buttons will push your guy over the edge.  It was fantastic to wake up in the middle of the night to find your guy spooned up against you  with his arms around you.

I also bottomed properly for the first time, all the way this time.  My extreme level of relaxation helped, knowing that we had all the time in the world.  The glass of red wine I drank also played it's part.  However, this time was more successful than our last attempt largely due to my position.

Lying on my back with my ankles up around his shoulders was amazing .... who knew that this decrepit middle-aged fart could be so flexible?   I know  this will become my favourite position although I plan to experiment with the dozen or so different possibilities for anal sex.  It afforded me good fondling access to thighs and a furry torso and a clear view of his "O-face"... the best thing of all!

This was no slam-bam affair.  It was an extremely slow process and very gentle,  The pressure was fairly intense, but I was pain-free throughout.  It was a very special feeling to be "filled in" like that,  much like a woman might feel during heterosexual intercourse except much, much tighter.

There still wasn't much outright "pleasure" to be had for me this time;  I was losing my bottom virginity, after all.   But at one point, I wondered if his cock was pushing against my prostate, one of my G-spots.....  that had it's possibilities for pleasure, that's for sure.

It will take me quite a few more bottoming experiences for me to fully enjoy it, but I was enormously proud of myself for achieving this milestone.  After my first attempt,  I could very well have said, "Forget this idea!" so am very happy that I / we persisted.

I am finding this part of my journey all-consuming with respect to the time I'm spending on it.   Apart from the time we spend actually spend together, we do much texting, phoning and e-mailing throughout the day.

I am still getting plenty of messages and chats on and, mainly from the 20-something flakes and 50+ dudes, many married and closeted but also from some experienced gay guys.   I have several 'irons in the fire' and at this point, do not feel the need to be exclusive although that may come soon.   However, my guy and I have agreed that we will not discuss any other guys who I may be hooking up with.  We did have these discussions at first but we found that opening that conversational can of worms did cause problems.

Sunday, February 12, 2012

Red union suit

At a thrift shop recently, I found a red union suit like these ones.   Score!!   I already posted pic of my white union suit, here.   Perfect timing, since it's been a little chilly recently (-20 C or 4 F)    I think it's the sexiest thing imaginable, especially unbuttoned down to there.   Aren't these guys adorable?

I'm thinking of wearing it for my first  sleep-over date on Valentine's Day, at least for the sleeping part of it.   Red wine, chocolate, great food* and best of all, all evening and all night in bed.... anticipation!

* appetizers eaten in bed

Friday, February 10, 2012

I bottomed .... sort of

I've been very much wanting to try bottoming for some time and we've been working towards that .... rim, lube, one finger, two fingers, etc.

I understand that relaxation is very important in this situation. My regular guy and I were together for a long time, about five hours, and he'd commented that he'd never seen me so relaxed. But I'm not sure if that outward relaxation extends to being relaxed "down there."

So, with much lube, a lot of time, gentleness and caring I received about half of the length before I'd had enough. The verdict was "extremely tight."

I understand that bottoming for the first time can be a big deal, so I know it will get better. While I wouldn't describe it as "painful", it wasn't particularly comfortable and there was little pleasure involved at that moment.

I also suspect the position I was in, lying face down on the bed, might not have been the best choice.... I must look into some of the other options. I am like the "Little Engine that Could".... "I thnk I can, I think I can....", so we intend to try it again. I'm not going to give up that easily!

My final thoughts:
  • I could not imagine, not in a million years, bottoming for someone who you didn't know, trust and feel a great deal of affection for.
  • Hundreds of millions of people have bottomed before me; if they can do it, so can I.
  • I thought of people who have been anally raped (such as those poor 10 year old boys in the shower at Penn State.) I'm horrified and sickened at the thought of the terrible abuse and pain they must have endured....

    Wednesday, February 8, 2012


    I returned a few hours ago from my trip to Toronto feeling like a horse that's been rode hard and put away wet, so this will be a very short post.  It was an exhausting four days for us two chaperones, leading our young charges through a gruelling program of big-city activities.

    I know many people, especially childless gay guys, find teenagers difficult to deal with, so imagine dealing with a dozen!  In fact, the kids were fantastic and we had enormous fun with them,  The challenge was to strike a balance between allowing them a certain amount of freedom and yet ensuring their safety.  Some of the kids were far from "street smart" but no one got sick, lost, mugged or injured.  Woot!

    Since I was "on the job" 24 hours per day., I didn't have too much time for private fun but I did manage to squeeze in a few gay things:
    1. I visited a sex shop, Priape, on Church Street, to stock up on necessities.  I also looked longingly at all the coolest brands of pretty man-panties.  At $40 or more, they were not something I could afford right now given my severe cash flow problem.
    2. On another day, I did a walk-through through the gay village and had coffee in a cafe.  It was was very quiet at mid-day but it was good to see the few the sweet, 70ish gay couples about.  It was great to be among my "peeps" and I felt a hundred times more confident than my last visit there in July.
    3. I went to Remington's male strip club on two evenings and had a fantastic time!  My visit on Monday evening was especially memorable it was nearly empty, with  a stripper-to-customer ratio of about 4:1.   More on that later.
    4. I would have wanted to hook up with some online Toronto friends and we did discuss some serious possibilities, but the timing, logistics and my chaperoning responsibilities  didn't permit this to happen.
    5. The gayest thing I did was to get my picture taken with a sweet, charismatic young man earning his way through university by posing for money in a
      Spiderman body suit. I admired his self-confidence and also for the way he filled out his spandex.  
    It took me an amazingly long time to summon up the courage to go talk to him and get a passer-by to take our picture.  It seemed like such a gay thing to do, especially on a crowded street corner!

    I told him that a gay guy like me would have great difficulty in deciding whether  his front or rear view looked better. … both looked fantastic!   He was cool about the compliment and thanked me.

    In the end, I was so glad that I posed with him.  I love the picture and it was so sweet (and arousing) posing with my arm around with him.   After a few days away from my regular guy, I was craving even that simple contact with a man.

    Sunday, February 5, 2012

    Where is Buddy Bear?

    Yesterday, I travelled a couple thousand miles to a major city for a four-day trip for my work.  The first commenter who can guess where I am will win a valuable prize, but I haven't decided what. Maybe a face pic of me?

    Since I am traveling with a dozen seventeen-year-olds who are in my charge, there will be no "gay fun" on this trip. This will be very different from my last trip, my Big City Gay Adventure, which I wrote quite a few posts on, from this one , that one and ending with this one   In particular, there will be no hotel-room hookups with random guys. To do so (and to be caught) could possibly result in the loss of my job and a revocation of my professional certification.  I may be courageous in my gay journey, but I'm not stupid!

    There is still much fun to be had on this trip, however. We are having the greatest fun mercilessly teasing the young man who attempted to board the plane with his library card as his only ID!  Being a very small town, the plane was delayed by ten minutes while his mommy raced back home to get his passport. What a hoot! 

    It is so much fun working with young people!  Some of the small-town teenagers on our trip had never been on a plane before, much less been to a major city.   The whole group was, in the words of one of them, "quivering with excitement" as we took off.

    While the young people had some free shopping time, I strolled through the gay village and took these pictures:

    Friday, February 3, 2012

    Rimming (NSFW)

    All pics from

    Platonic Date:
     Last week, I had a coffee date with Dave who had disclosed that he was HIV+.  He was very discouraged when I told him that we would never be intimate.  He used to that reaction;  when local guys find out of his status, he never nears from them again.  In two years back in town, he`s only had sex twice.

    He had been stood up for the previous four coffee dates.  I said I would never be that cowardly;  if I didn't want to go out with him, I would at least tell him.

    I invited him to attend a local film festival with me last Sunday.  I already had two tickets but my daughter was not able to attend.   We met for coffee an hour before the event.   Dave was much less nervous than our first meeting;  last time,  he was visibly trembling.

    This time, we had a lively gay-themed conversation.  At 19 (25 years ago), he was outed to his family by his "roommate's" mother.  As a result, he has very strong views on allowing people to come out on their own terms and timing.  He's lived in major cities all over the world and has had a vast experience in all matters gay.

    Do you want to know about gay guys in different ethnic groups?  Well, he's had 'em all!  Guys with the biggest cocks and balls?  Spaniards.  The most passionate guys in the world, capable of giving you the greatest pleasure, especially if you're a bottom?   Brazilians.  (No surprise there!)

    At the crowded film festival,  I met a dozen people that I knew in the first five minutes.  We said "hi" in passing but I didn't introduce Dave.  They might have wondered what I was doing there with a guy, but frankly, I didn't give a damn what they thought!

    As to the film festival, I loved it but the films weren't Dave's cup of tea at all.  He was very polite about it, but after two hours, we both had had our fill.  It was only half finished, my back was sore and I wanted to get home to my daughter.

    I dropped him off at his parents', a 700 square foot house in a pretty rough neighbourhood;  he lived in a tiny attic room.    He shook my hand and said he had a great time;  he said that it was good for him to get out.  We said we'd get together again in a week or two, maybe go to the gym.  Two days later, I received a confusing message on from Dave.  He later apologized for the message, saying he was"drunk and horny" when he sent it.  Oops!

    Another 20-something chat:
     Fresh off my sweet encounter with Trey, I received another message from yet another  a 25 year old who claimed to be "seeking a woman' in his profile.  He wrote:

    I'd like to meet you. I have no experience. Maybe we could teach each other...?
    How sweet is that?   How could I possibly say "no?"   I'd practically be doing a public service, launching these questioning young men into an exciting life of gay sex.   This new guy and I chatted for about a hour.   He seemed as sweet as my first impression of him but I was "playing it cool" .....  just reeling him in.

    With these guys, it is best to let them get their courage up, for them to make the first move.  Sadly, I had to go to work so we cut our chatting short.  It's been two days and I've had no communication from him,  despite several opportunities to do so.  Sadly, I think he's yet another 20ish "straight" guy who is just not ready to take that next step.

    My regular guy and I had discussed rimming .... I said that I wanted to experience what it felt like.  Then why was it such an unexpected (and delightful) surprise, when, after hours together, he flipped me onto my stomach and dove right in?   I didn't know what to expect, but the warm, ticklish , entirely pleasurable sensation sent shivers throughout my body.  It wasn't orgasmic or anything....  I'm not sure what it was supposed to even feel like.   But mainly I laughed out loud at his boyish enthusiasm,  his delight as he dove right in.

    I look forward to being rimmed again.  I've come a very, very long way in three weeks, but it will be a while, I think, before I actually do the rimming.  It will take a bit of time to get my head around that one.  When I'm comfortable with the idea, I'll be the first to know!


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