The Jockstrap

He had walked past the shop numerous times before. First it had sparked his curiosity, then his fantasies, until his nerve finally held and he stepped through the door. He was greeted by nondescript dance tunes and shortly after by a sales assistant who appeared from behind a rack of black latex apparel. 

“Hello, can I help with anything?” the man asked him with a reassuring smile. “Yes, I’m looking for underwear. Briefs, trunks, that sort of thing…” he replied, less confidently than he had hoped. “Sure, our underwear section is downstairs,” the shop assistant advised and pointed him towards the stairs next to the till. 

He nodded his thanks and went down the narrow steel staircase. The basement was more spacious than he had anticipated and illuminated with spot lighting. On the back wall he made out a selection of briefs on hangers. Manoeuvring past unreasonably sized dildos, cock rings and other, hard to place paraphernalia he reached the underwear section. 

Feeling unobserved, he browsed through the racks. 

“Found something you like?” came a sudden voice from behind. Startled, he turned around to see the sales assistant descending the stairs. “Still browsing,” he answered. “Quite a selection you have.” The other man had joined him in the narrow aisle, running his hand along the hangers while eyeing him up and down. A smile playing around his lips, he observed: “I think I know the right style for you.” 

He reached up to one of the wall mounted racks. “I’d always go with a number smaller than usual with this cut. Try these.” Enthusiastically he handed the shopper a cobalt blue jockstrap with black elastics and one with a silvery grey pouch. “You can put them on over there in the cabin.” Following the advice, the customer went inside and closed the knee high curtain. 

Hesitantly he took off his shoes, followed by his trousers. Dropping them to the ground, he slipped off his boxer briefs as well. Facing the half length mirror, he saw his penis twitching, having already started swelling up over the course of his exchange with the shop assistant. Quickly he pulled up the blue jockstrap, just managing to fit his member into the bulging pouch. 

He felt a gust of air on his bare behind as the curtain was pulled back. 

“Looks great, just as I thought,” the sales assistant proclaimed. Stepping into the cabin, he pushed the customer’s t-shirt up, placing his warm hands on his waist. “Those buttocks deserve to be on display. You like it too, it seems?” The man in front of him blushed, looking down at his own erection in the mirror which was about to burst from the jockstrap. 

The shop assistant moved his hands back and down onto naked buttocks. After giving them a firm but gentle squeeze, he ran a finger in-between the cheeks. Finding the clenched hole, his middle digit massaged the tight ring of moistening muscle. Moaning, the man before him bent forward slightly to steady himself with his hands against the mirror. 

The customer watched as the man behind took a packet of lubricant from his pocket. Ripping it open, he let the warm liquid drip onto his crack from above. As it slowly seeped down towards his hot hole, the shop assistant opened his own trousers and pushed them over his pelvis. His hard cock stood erect while he rolled a condom over the shaft. As he finished, the lube had reached the expectant sphincter. 

Gripping his cock at the base, he placed its tip against the glistening hole. 

The customer flinched as he began pushing the engorged glans through his sphincter. Putting one hand on his lower back to steady him, he continued unperturbed. Gradually wriggling its way forward, eventually the rim of his cockhead penetrated the resistant ring of muscle entirely. “Ahhh,” the other man hissed with a pained tremble in his voice. Gripping his hips with both hands, he thrust his stiff cock forward and deeper inside until its full length was buried inside the rectum. 

They were both panting in unison while the shaft was beginning to drive in and out between firm cheeks. Their eyes met in the mirror briefly, flickering with the lust of the moment. Having his tight hole hammered, the customer had to resist the urge to grab his own throbbing cock, instead closing his hands into white knuckled fists. Sighing deeply, the man behind came, his semen pumping through his rock hard rod. As he withdrew, the customer straightened up, observing his own erect penis, still nestled inside the taut blue pouch. 

“Are you going to wear it out?” the sales assistant asked. “Yeah, I might as well…” the customer replied. Having dressed, he followed him up the stairs and to the till, paying for his new purchase. “Come again,” the shop assistant beamed as he turned to leave. “I hope so. Next time maybe…” he replied and stepped back outside. 

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