First Jockstrap Comes with Fringe Benefits

Hello guys! My name is James. I come from a small town in Oregon, USA. I’m 19-years-old and a virgin. The only thing I know about sex is a stallion fucking a mare. I like to wear tight jeans and jerk off in the haystack, thinking of naked men and women. Not sure whom I would choose if there was only one possibility. I saw an ad for jockstraps in a catalog, and it turned me on 200%. I get hard so quickly and masturbate with more vigor when I imagine a heavy hairy guy like me wearing this special sexy gear. Does that mean I’m gay…?

I am now visiting San Francisco, strolling down Castro Street. I heard that it attracts a lot of gay guys. I wouldn’t mind having a drink with a hairy and heavy built man like me. I have not yet caressed a man, yet alone touch one in a special way. What I want now is to find a boutique selling jockstraps. I notice a shop advertising leather gear, dildos, cock rings and… jockstraps. It is early on a Monday morning, well 11 am, but the place is totally empty. I enter, look around, find the jockstrap corner, examine the various brands – had no idea there were so many –, choose a red one, and ask if I can try it on.

“Yes, but over your underwear”, answers a handsome employee.

“I picked up a CellBlock 13 in a large size but I’m not sure if it will cover my big…, I mean my full crotch.”

“Put it on, come out and let me see.”

I enter the cabin, remove shoes and jeans, slip on the jock, and come out to face the teller. He immediately adjusts the pouch and the straps. His hands over my dick make it grow slightly. He winks at me and says: “You take at least extra-large. Stay there and I’ll get it. It’s not busy, I’m all yours.”

I wonder what he means by “all yours”. Is he just polite or perhaps interested in me…? I don’t have time to imagine a possible scenario, he comes back with the extra-large red jockstrap and looks me straight in the eyes, with a hand on my semi-rigid crotch: “I’m Brad, nice to meet you, try this one, it’s the largest we have in a red CellBlock 13 brand.” I slide it on over my bulging underwear, but it still feels too tight. “My name is James, not sure this size is large enough.”

“Maybe it will fit better without your underwear, but I have to be sure that your cock and balls are clean. Let me see what you’re sporting so fucking nicely?” As soon as I get naked, Brad starts to lick my shaft and balls. He then sucks my rod, while caressing his own bulging crotch. “You’re clean now, James, but the extra-large jock will overflow because you’ve got the biggest bazooka hard-on I’ve ever seen.”

“Thanks, Brad. It’s the first time a guy sucks my cock and it felt sooooooooo good!”

“I was sure you were an experienced gay man, especially with a rod that size. Glad you liked my tongue massage! It’s normal that a jockstrap feels tight when you have a hard-on. Let me suck your man juice and see how a ‘normal’ dick fits in the extra-large pouch.”

On that note, Brad swallows my shaft as far as he can – about 7 of my 10.5 thick inches –, and pumps me so well that I burst ropes of creamy nectar that he swallows at 90%, keeping 10% for a snowball kiss. Fuck! Now I have no doubt in my mind, I’m 100% gay! I also want to suck him, and it doesn’t seem to be against any policy rule for employees. Brad is more than willing; he directs me to a larger cabin with a small bed, like in a sauna bathhouse (I later found out). He has a 6-inch cut penis, not too hairy, with low hanging balls. As everything is new to me, he guides my position for a 69, caressing my hairy pecs, squeezing my balls, tickling my cock with the tip of his tongue. That obviously gets me harder. I copy his gestures and we end up sucking each other like the end of the world was close. We both swallow and kiss voluptuously.    

Even at rest, my dick seems a bit too big for the extra-large CellBlock 13 jockstrap. Brad is a resourceful employee, and comes up with a solution that overwhelms me. “I have this made-to-measure leather jockstrap. It was for a bear about your size, but he never picked it up, even after having made a 50% deposit. If it fits you fine, you can have it half-price.” He turns around to get the handmade leather gear and helps me tuck in my precious jewels. He adjusts the straps around my ass and moans with delight: “I want to be the first one to fuck that hairy firm butt! And I know a hairy bottom friend who would love to be fucked by a well-hung guy like you.” I obviously have no knowledge of fucking, except for the stallion stuffing a mare.

A client comes in the shop and Brad pushes me back into the cabin, whispering: “Wait for me here, it won’t take long, he’s only picking up a made-to-measure harness.” A few minutes later, Brad locks the door, puts a “Closed for 10 minutes’ sign, and comes back to fuck me. I’m in for a total surprise. He licks my ass, tongue-twists its way inside making me moan with unthinkable pleasure, then inserts two fingers to lubricate my hole. Brad has experience in shoving his pointed dick in a guy’s ass; I feel the pounding with a light pain at first, but ecstasy takes over me. Brad positions me so that he can fuck, jerk and kiss me in a well-choreographed scenario.

I leave the boutique with my leather jockstrap on, and we schedule a dinner meeting, followed by my first experience fucking a guy. Brad’s hairy bottom friend is a wonder bear: George is about 20-years-old, measures easily 6 feet tall, weighs 220 pounds, has a dark beard, is hairy all over, has a nice belly, and sports a huge watermelon ass. My wildest dream is about to come true! Brad is filming the scene and I follow his instructions. George is not much into kissing or getting sucked, but he enjoys rimming. “A guy like you can eat my ass for breakfast, lunch, dinner and midnight snack. Best preparation for a hard and deep fuck!”

That is what I intend to deliver. It’s my first but certainly not my last time as a Top (I quickly learn the meaning of Top and Bottom). I keep my leather jock on, snapping the pouch open to let my bazooka emerge forcefully. I want it fierce, savage and raw, like on the farm. I’m the stallion and George is the mare. My dynamite punches make him scream, howl and moan with virile pleasure. It is so fucking hot when Top meets Bottom in wild complicity.