Inexperienced trailer park hottie

 Today's pics are from Flip Flops Boy and all resemble my new friend, Trailer Park Hottie.

I live in a rural area, so a hookup invariably involves a 30 minute drive to town or for a gentleman caller to drive here.  Too often, men say that I live too far away for  hookup.

In the case of a car-less young hunk (usually a student), I often drive into town to pick him up, bring him to my house and then reverse the process at the end of our sexytime, 120 km (70 miles) in all.  And I must add, all this driving is well worth the rewards received.

So imagine my excitement when I was Grindr - messaged last summer by a 28 year old hottie, 5'8", 150 pounds who lived only 4 km away!

Although I never received his face pic, other of his pictures revealed a toned, lightly furry and tattoo-free torso, a hint of abs, a magnificent, above-average cock and and a full bush of rampant pubic hair.  A rarity, these days!

Over the next nine months, Trailer Park Hottie "played footsie" with me, usually messaging me around midnight a few times per month.  He was usually bored and horny and often asked me questions:  "What do you do with a guy in bed?  But after a few minutes of chat, he would log off Grindr and often not log on again for a week or more. 

Over many months, he also sent me many pics of various of his body parts:  cock (hard and soft), balls, ass and thighs.  So hot!   But I gradually came to the conclusion that he was either a tease or was extremely inexperienced and lacked the courage for a face-to-face meeting.

To use a fisherman's analogy, it took me many months to "reel him in."  When  I finally meet a young man in person, I always ask: "Why did you pick me out of all those dozens of profiles?"

They always same the same thing:
(1)  They liked my face picture, usually describing it as "handsome" and sometimes "kind."
(2)  I took the time to get to know them online and to talk honestly about myself in a non-sexual way.
(3)  I never initiate the conversation about sex, ever.  Inexperienced young men hate it when an older guy starts the conversation with a crude proposition.  ("I want to pound your virgin ass!" or "I want to suck your cock!")  

Finally, last Friday night (at 1:00 am!) I received the message: 

Trailer Park Hottie:   "Can you come over now?  We can sit on my couch, watch porn and jerk off together.  But I don't want you touching me."

Buddy Bear:  "Dude!  It's too late and I'm too tired!  Message me on Grindr any time tomorrow and I'm all yours"

All day Saturday, I monitored his Grindr profile and watched as he logged on and off all day long, building up his courage.  Finally at 5:00 pm, he messaged me:  "Can you come over?  But it has to be right now.  I don't have a lot of time. "


Trailer Park Hottie was absolutely adorable, a cutie who greeted me at the door shirtless (a lean, lightly furry torso!) with dishevelled hair, bare feet and track pants revealing a promising bulge.  He had a sweet smile but otherwise was too nervous to speak and was trembling visibly.

On the couch, I took off my jeans to reveal my rock-hard cock stretching out my Andrew Christians.  He was so hot!  He unzipped and started to play with his cock which quickly grew to +7 inches and quite thick.  A thing of beauty, especially on a smaller guy!

Although Trailer Park Hottie told me in advance that I would not be allowed to touch him, I put some lube on my hand and asked, "May I?"  He nodded and I applied lube to his beautiful cock. He stretched back, closed his eyes and moaned and trembled as I used the cock massage techniques taught to me by Rick of Torn Jeans.   So incredibly hot! 

At one point, I whispered in his ear: "Do you want to touch my cock?"   He nodded, so I applied lube and he gave a firm-gripped handjob which made me squirm.

Much later, I whispered again in his ear: "Hey baby, I you to cum my mouth.  Can you do that for me?"  He nodded again and after very little effort, I had a blast of his sweet, salty cum in my mouth. So hot!   I kept his cock in his mouth for a few minutes after he came, feeling it throb sporadically and gently massaging it with my tongue as I caressed his belly, balls and inner thighs with my hands.

To avoid any after-hookup awkwardness, I pulled on my pants and prepared to leave.  Trailer Park Hottie hugged me (at my request) and said:  "Next time, I'd like to try some of that on you."   Next time? Woo-hoo!

Golden shower

I've been too busy and exhausted to blog this week, yet again.  Most days, I have every intention of doing a quick post at bedtime but invariably, I fall asleep instantly.  But here a few random snippets of my week.

1.  The cute, passionate cub who gave me my best complement ever ("You fuck like a porn star!") wants me to pee on him and then fuck his Hungry Ass.  Although I don't understand the sexual appeal of being peed on, I've decided that I want to do it .... I think it might be fun and it will certainly be another interesting item crossed off on my gay sex bucket list.

But now I am starting to have Peeing Anxiety, more correctly, Volume Anxiety.  I am a middle-aged man, after all, and I never could pee like a race horse, even in my prime.  But Sexy Cub assures me that is not the volume of pee which is of interest, rather, where it is aimed. 

Does anyone one have any experience with this, or advice? 

2.  My son traveled just over half-way across the country to come home for his Spring Break.  Although he just turned 18, I am struck by how self-confident and self-reliant he is, as well as being a total hunk.  He's extremely handsome; very blonde with brilliant blue eyes,  broad shoulders and slim hips.

He spent most of his time with his girlfriend (a beautiful, quirky, intelligent young woman who was my student for grades 10, 11 and 12), his posse of close friends and slept a few nights at his mother's house. 

Despite that, I saw him nearly every day "on the fly" for short periods of time.  His time was seriously divided but he did his best to see me.

I was sad that he wasn't with me full time, but then I considered how divided his time was and how much pressure he must have been under to spend time with everyone.  When your kids are adults, it is natural to see less of them and in a divorced family, the kids' time is even more divided.

2.  My eldest daughter turned 23 this week and I hosted birthday lunch for her, my son and parents.   As my daughter is a chef-in-training in a fancy gourmet restaurant in town, I put pressure on myself to produce a "gourmet" lunch.

The menu:  a salad of mixed spring greens with maple vinaigrette, candied pecans and shaved parmesan, crab cakes with corn and cilantro, freshly baked biscuits and that 70s classic, Bacardi Rum Cake baked in a Bundt pan!

3.  I attended a drag event where Hunky University Student was a featured performer.  I was overwhelmed and awe-struck by his on-stage presence!   As a woman, he was gorgeous and voluptuous, with incredible energy, charisma and sex appeal. The crowd went wild!

At the end of the evening, a very drunk married couple staggered towards me at the door.  The handsome, well-dressed 40ish husband pressed $10 into my hand.  Can you call us a taxi?  I laughted:  "Are you serious?"

He hugged me and slurred: "Yes, you look after us and I'll look after you!"  I did what he asked and with one arm wrapped deliciously around his mid-section, helped him and his attractive, voluptuous wife (who had been giving me the eye all evening) into the taxi.  I had a fleeting thought: if they had offered me $200 for a threesome, I would have said:   "Hell, yes!"

Hookup with a drag queen OR Butt-fucking while standing up

I'm always on the lookout for attention-grabbing post titles and I couldn't decide between these two, so, what the heck, I decided to use them both.

I'm finding that this one-a-week posting just doesn't work for me;  there are so many stories that are falling by the wayside, unreported for my own personal journal of my gay journey.

It's been an exhausting week and I've been too busy to post, what with my regular teaching duties, school extra-curricular activiyies, Pride planning work and hooking up with some fine men.

I had hookups three nights in a row with three very special men.

Wednesday Night:  After many months of messaging, I hooked up with a married guy who occasionally likes to play with men with his wife's blessing, he said.  He drove to my house from an isolated northern region some one hour away and brought a bottle of red wine to share.  Classy!  And highly motivated!

He didn't tell me his age but I pegged him at 40 but he had an incredibly fit, boyish figure unlike I'd ever seen on a mature man.  I was shocked when he told me that he was 56, the father of three with numerous grandchildren.

Boyish Married Guy had a most remarkable life story:  he left school at 13 and was on his own by 16, doing the work of a grown man.  He earned his fine figure with a lifetime of doing heavy labour on the railroads, in northern logging operations and in various mines.  Although he limited schooling, he was intelligent and extremely interesting to talk to.

When asked about his wife, he said, fondly:  "Oh, she knows I like cock!  I told her all about it when we started going out forty years ago."

He went on to say:  "She beautiful!  An amazing woman!  I love her more than anything and we have sex all the time, still.  But she knows that I need to have a cock up my ass every now and then..... she understands completely."

We had the most intense hookup ever which lasted several hours, and yes, plenty of butt-sex happened.  He'll be back, he said!

Thursday Night:  I spent the next whole evening, about five hours, with the handsome and insatiable 19 year old university student who I blogged about here.    He's a champion cuddler, a fantastic kisser, horny as hell and a dead ringer for Adam Lambert. 

Hunky Student has the same FABULOUS mop of dark hair, intense eyes but was quite a bit chubbier than Lambert.  At Hunky Student's request, I modelled my collection of Andrew Christian undies; he liked the jockstrap the best.


What I'll remember most about our encounter was the after-glow of our sex, when he laid his his head on my furry chest and looked at me with what seemed to be adoration. Very intimate!  Later, we lay naked together with our limbs entwined and lips pressed together and we both fell sound asleep.  So sweet!

And yes, Horny University Student revealed to me that he has been a drag performer for two years and invited me to his next performance next week.  I can't wait to see him!  We spent hours discussing the appeal of drag and technical aspects of its performance;  I received quite an education! 

Friday Night:   I spent yet another evening at the swanky airport hotel with Hunky Brazilian flight attendant.   So hot!  It was also my first experience as a top doing stand-up butt-sex which, to be honest, I found to be a pain in the back.  But I'll have to write about my new Brazilian friend in my next post.

But I will say at this:  he wants to see me in three weeks, the next time his flight schedule brings him to town.  This leads me to this question:  How many "regulars" should a gay guy have?  I have a dozen or more!

Passionate Brazilian flight attendant

Like most places in North America, it's been a very cold winter;  our average temperature in February was the coldest in our entire recorded weather history.

But due to the improvements I made in the plumbing system, my water system only froze once, very minimally, which I was able to thaw out in minutes.

This was huge improvement over last year where I had daily freezing issues for most of January and February.  Woo-hoo!  But in the past two days, temperatures have soared to 0 C (32 F)!  Balmy and spring-like!  To my great amusement and pleasure, I noticed a few young men going around town in shorts.  :-)

I haven't posted in over a week not because I had nothing to blog about but I was too busy with gay shenanigans to blog about them including several sweet hookups.  I fear that my posts are getting a bit repetitive.  But here is an update from last week:

• Every day, I see hot naked guys at my gym with beautiful cocks and asses, letting it all hang out in the communal showers and locker room.  It is one of the simple pleasures of my life which I never tire of.
• I had a four hour hookup with a Brazilian flight attendant at a swanky airport hotel!  He was 35 but looked ten years younger.  He was intelligent, passionate and deeply appreciative of my efforts and highly vocal.  I asked: "Aren't all your hookups like this?"   He shook his head vigorously:  "You have no idea !!"
• Passionate Brazilian resembled the handsome guys pictured here but without the visible abs;  lightly muscled, smooth and with a shaved head and beautiful dark eyes.
• Passionate Brazilian was so thrilled with our encounter that he made an arrangement get together next Friday, his next stopover in town.  Yes, sir!

• At my school, our GSA has been re-invigorated with help from our students' council and we now have two transgender students (trans boys), two lesbians and (I think) two female allies, "friends of...." attending regularly.    
• The sad part is that most of the gay teen boys are as deeply closeted as ever.  How do we reach them?
• I attended our city-wide Gay Straight Alliance planning with 25 FABULOUS queer students;  such courage and enthusiasm!  We planned many joint and school-based queer events and I am planning a trip for delegation to the national Canadian GSA summit in May
 

The one thing that I won't be blogging about is my exciting weekend visit to a major Canadian city to visit a special friend, perhaps future husband material, who moved there a month ago.

We had a fantastic time but mainly "played house", rarely leaving his downtown condo.  But it remains bittersweet, I think for both of us, living so far apart among other complications.