Jockstrap + Leather Boots = High Performance

I was around 14 when I saw a jockstrap for the first time. It was one with a protecting cup to wear when playing hockey, worn on top of your underwear. It would take a few years before I discovered the type of jockstrap worn by athletes like wrestlers or cyclists. I was a bit shy when I bought that kind of sporting good, but I never regretted it. A whole new world of erotic pleasure opened up!

Not sure if you know, but this underwear was first invented in 1874 by a Chicago sporting goods company called Sharp & Smith. Its designers were looking for a bespoke underwear solution for the bicycle jockeys working the cobblestone streets of Boston. Something to prevent cyclists from crunching against the hard seat on their delivery run.

When I entered university, my English teacher said he needed to make an evaluation, and asked us to write a composition on the topic of our choice. I don’t think I have ever been as bold, but I wrote about the joy of wearing a jockstrap. Here is a bit of what I included (I’m probably enhancing my composition here, but that’s the joy of writing).

I started by saying that the basic design of the jock-strap is fairly uniform:  an elastic waistband to which is attached a support pouch for the cock and balls, and two elastic straps affixed to the base of the pouch and to the left and right sides of the waistband at the hip. Then, I went on to say that sports teams of North American schools and colleges were big enthusiasts of the jockstrap.

The term “jock” – commonly used in North America to refer to an athletic guy – emerged in the late 1950’s, and comes from the jockstraps worn by sporty guys. Today the jockstrap has transcended the sports-field and has been incorporated into the everyday wardrobe of many gay men.

My first bold statement was revealing that when I was in grade 12, my gym teacher asked us to wear a regular jockstrap (no cup), and that I got to see some classmates in the hottest manly place: the locker room. It didn’t take long for me to associate this gear to steamy masturbation material or inspiration!

Nothing could stop me! I asked why do gay men adore wearing a jockstrap? I answered that they like the feeling of both wearing something but still feeling exposed and naked. They like the feeling of being somewhat constrained. They associate jock straps with athletes and virility. They think it accentuates intimate features of their partners like lingerie does on women. They just think it’s cool.

I concluded by stating that jockstraps show off your best… assets: “Who doesn’t want a perky ass? Those two straps below your butt help prop up your booty an extra inch (2.5 cm), and the pouch highlights your package. Jockstraps are probably the most accessible underwear for getting freaky. Need to hump in a hurry? Bottoming? No removal necessary! Topping? Just slide the pouch over. What other undies can you keep on whilst fucking or getting fucked?”

I read somewhere that a healthy sperm count involves keeping the testicles lower than the rest of your junk. Jockstraps keep them at a perfect level while keeping your penis front and center where he belongs. Jockstraps give us that “next to nude” feeling while still covering up our jewels. We dig them because they give us that sexy factor: knowing you've got hot underwear on can make any man feel a little bit sexier. A recent online survey indicates that 68.6% of gay men wear jockstraps on a more or less regular basis.

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The title of my story includes leather boots. Enter Jacob, a guide I had when visiting Poland almost twenty years ago. This handsome 40-year-old bald man gave our group a tour of Warsaw. I was immediately intrigued (and attracted) by his dress code: he not only wore a leather cap, coat, and pants, but also a pair of knee-high boots. I followed him closely, as you can imagine, asking questions, even offering a beer when we stopped for a free visit of the monument of the Warsaw Uprising, and former Jewish Ghetto area with the Umschlagplatz (term used during The Holocaust to denote the holding areas adjacent to railway stations in occupied Poland where Jews from the ghettos were assembled for deportation to Nazi death camps).

Jacob certainly sensed that I kind of had an eye not only on his boots. He winked a few times and brushed his leg against mine. The signal was so clear that I dare put my hand on his thigh. He immediately grabbed and squeezed it. “I’m free after the visit”, he whispered. “Can spend the whole evening and night with you if you want”, I answered.

I was the last one to tip Jacob. He wanted to give me change for my 20 US dollar bill, but I insisted: “You deserve it, you made my day!” I followed Jacob to his apartment and was struck by all the pics of guys cladded in leather on the walls of the living-dinning-sleeping area. This guy had a such a virile fetish! That was just an appetizer. When he undressed, his bulge was highlighted by a leather jockstrap. I was fucking glad that I was also wearing a jock.  

Jacob’s butt was already perky. The straps marvellously enhanced this asset. After kissing and caressing on the sofa, I was naturally drawn to his slightly hairy crack. I asked him to sit on my face and let me brush my beard against his wild offering. I didn’t loose time to kiss, lick, and slap his arse before tongue-twisting my way inside his satanic haven.

My Polish guide “guided” me to his boots. He certainly wanted we to lick them. It was the case, but he had a plan. A first lick triggered a firm 6-inch (16.25 cm) hard-on. He then opened the chest that seemed to be a coffee-table; it contained at least three pairs of boots. He put on the cowboy boots, and believe it or not, as I licked them, his cock went up an inch more (2.5 cm), gradually bursting out of his jockstrap. Fuck, sex with Jacob was so hot!

He then put on the Harness motorcycle boots and, with each of my stroke-caress, his cock instantly reached 8 inches (20.32 cm). I was drooling as much as his mushroom. The next pair of boots was a replica of the Royal Canadian Mounted Police’s brown boots with spurs; they measure 17 inches high (43.18 cm). As I shined them with my spit, I could hear Jacob moaning, begging for a creamier shine. I jerked off and ejaculated over both boots. His cock had now reached over 9 inches (22.86 cm). I wanted it deep inside me. A powerful raw fuck!

Jacob positioned himself to shove his engine in my tight hole. I could sense that he had the hot feeling of deflowering a virgin. It wasn’t the case, of course, but I had never had a huge Polish sausage up my ass. Physical pain quickly turned into virile, savage pleasure. As he kept pounding me, I held on to his boots, encouraging my “mounted police” to explore the wilderness of my rear end. His explosion was an ecstasy!

I can just imagine what would have happened if Jacob had worn a pair of rubber hip boots. The inseam is 32 inches (81,28 cm). Holy fuck, jockstrap + leather boots = high performance!