Dean gripped the steering wheel tightly as his blood boiled. How dare Mr. Gilmore question his present? Sure, he was Rory's grandfather and was concerned about her safety but Dean had built that car himself. He had checked it. His father had checked it. Yet Richard hadn't trusted his work and now the two of 'em were driving to Hewes Bros, in two cars, to have it checked by Gypsy. The old man had even asked him to drive behind him to avoid any problems... It was so disrespectful. He would have never done anything that could have put Rory in danger.
"What the-?" Dean mumbled as he watched Richard's car ahead blink and pull up in a lay-by. Confused, so did the boy, parking behind him. A funny thought crossed his mind. What if the old man's car had broken down and now he needed a ride? Well, that would be such a setback for Mr. Gilmore... With a smug smile on his face, Dean opened the door and stepped out of his car, walking up to the older man to check on him.
"I didn't blow a tire if you were wondering. I just thought that maybe you could use a ride" Richard explained subtly, rolling down his window. The young boy gave him a bland look and so Mr. Gilmore gave him a more explicit hint by reaching for his bulge and squeezing it.
"S-sir, I-I-I..." Dean mumbled, baffled and speechless. He had been caught off guard. His bravery had given way to a scared little boy, the one he actually was. The old man's lips curled up into a devilish grin as he rubbed his clothed dick through his pants with anticipation.
"Listen, kid. Rory is our only granddaughter and, trust me, my wife isn't going to like you. If you want an ally, you better do as you're told and take a ride on my rod. Understand?" Richard explained, his voice sounding like a subtle threat. His prey had wound up in his trap. He had watched Dean approach boldly from his rear-view mirror, and now he was panicking.
"... ok. I-I'll do it" Dean said, eventually giving in. He had thought about getting back into his car and driving away but... what for? If this could help him be with Rory and forget what had happened with Christopher and Luke then... fine. Mr. Gilmore sneered and opened the car door, promptly pulling his 6,5 hard inches prick out of his pants, the head glistening with pre-cum.
Dean looked around to make sure no one else was there and reached down to undo his belt. He was a bundle of nerves as he kicked off his shoes and slid his pants off, his briefs following soon after. A shiver ran down his spine, the cold air hitting his bare ass and soft junk. What on earth was he doing? Richard gave his stiff pole a couple of strokes and adjusted himself on the car seat, spreading his legs wider to accommodate the young boy. Without further ado, Dean got in the car and straddled the older man, positioning himself onto his lap. His heart skipped a beat the moment Mr. Gilmore spread his cheeks apart and nudged his hole with the tip of his cock. Jeez, it was so wet...
Keeping his gaze down not to meet Richard's, Dean gripped the older man's fat cock by the base and began to lower himself down onto it. His breath hitched as the pressure built and built until the head popped in past his initial resistance. Mr. Gilmore let out a soft groan, his hands gripping the boy's hips tightly. How delightful... He enjoyed the look of discomfort on Dean's face as he struggled to sink further down, taking more of his length inside him. It wasn't easy, though. Pre-cum had mildly lubed his entrance but not enough. Yeah, Richard's cock wasn't huge but still quite thick and stretched him wide. It hurt so much.
A few inches away from bottoming out, Dean paused to give himself a moment to get used to the intrusion but the older man wasn't interested in waiting. At all. He thrust upwards and buried his entire shaft in, balls deep, making the young boy cry at the sudden impact. Shit... That whimpering was music to his ears... Plus the tight heat enveloping him was driving him nuts... A tear formed in the corner of Dean's eye and fell down his cheek, his body trembling.
"What's the problem? I thought you would ride. Then, ride already" Richard urged, amused, as he gave the younger man a hard slap on his butt, making him arch. He loved being a pain in the ass... literally. Dean bit his lips, trying to steady his breathing, and began to move. He started out slow by lifting himself up slightly before sinking back down. Over and over and over. Each movement was excruciating. The friction was acute as he felt the older man's shaft split him open, inch by agonizing inch. He tried to relax and calm down, but to no avail.
"E-easy, please..." Dean begged, with a soft whisper. His plea went unheard, on the contrary, Mr. Gilmore's grip on his hips tightened, guiding him to keep the pace he demanded. The young man obliged, exhausted. His eyes were closed and his face contorted in woe as he rode Richard with increasing speed and desperation, his limp willy bouncing against his stomach with each thrust. The sound of their wet bodies slapping together filled the car, adding to the intensity of the moment.
The older man threw his head back, groaning like a pig. The way Dean was sliding up and down, fucking himself on his fat cock... That kid was a promising whore. He just needed the proper training. As his orgasm approached, Richard couldn't help but buck his hips and hump to chase his release. The younger man felt it too and ignored the strain in his muscles in the hope that it would be over soon. Luckily, he didn't have to wait long. After a few deep and settled plunges, Mr. Gilmore pulled out of his abused ass and came with a grunt. His nails dug into the kid's flesh and his body tensed as 6 spurts of warm, sticky jizz squirted out, most of which painted Dean's pale butt and his own hand. For a while, they were frozen in time. Then, it subsided.
"Not bad... You've been good..." Richard panted, his chest heaving as he tried to pull himself together. Finally, he let go of his grip on the younger man who got off of him and rolled onto the passenger seat with a gasp. Holy shit... his ass was sore. He was about to break down when Mr. Gilmore gave him some light slaps on his face with his cum-smeared hand. "Get a hold of yourself, kid. We're not done. I still need to make sure the car you built is safe"
Dean nodded, accommodating. His eyes were glassy, empty. The smell of sex and sweat kinda made him sick. After a moment of hesitation where he watched Richard put back his cock into his pants like nothing had happened, he opened the car door to retrieve his clothes and threw up on the street.