GayCest – Teaching My Grandson – Tape 3 – Hard Lessons – Jack Bailey and Lance Charger

Jack Bailey was pretty gutted when he didn’t get the job he’d hoped for. He’d worked so hard to prepare and present himself as best as possible, but in the end, it didn’t work out. Jack had always challenged himself and was no stranger to defeat, but something about this one stung a little bit more.

Jack’s grandfather had done so much to help him and he really valued that time together. In a way, he felt like he wasn’t alone in the interview or anything else because the two of them were a team. He felt like he was standing on the shoulders of the giant that was Mr. Charger and that would help him go farther than he imagined.

Of course, the hard lesson he had to learn was that he was his own man at the end of the day. With all the love and support of those behind him, he was going to be judged on his own merits. As his grandfather read the letter of rejection, he felt embarrassed that such a powerful and successful man as Mr. Charger had to be part of his failure. He didn’t want to disappoint himself, but Jack didn’t want to disappoint his grandfather even more.

When Mr. Charger could see the boy beginning to sink deep into the office chair, he immediately knew they had to course correct. No longer was the task about jobs or interviews or preparedness, but it was about making sure Jack knew he was still his special little guy.

Mr. Charger pulled Jack Bailey over to him, letting him sit on his lap as he’d done when he was younger. He put an arm around him and told him how special he was. He knew he had to make Jack feel better any way possible. And lately, he’s discovered something that always puts a smile on the young man’s face…

Standing up, Mr. Charger gave Jack Bailey a kiss on the lips before bending him over the desk. It was sudden and fast, but it was enough to let Jack know what was coming. He didn’t have to think about the job or the letter, or anything else but what his grandfather was doing.

Mr. Charger pulled down Jack’s pants, getting a close view of his soft, smooth ass. He kissed it softly at first before diving his face deep between his cheeks.

“Isn’t this better?” the grandfather asked, smiling and looking up at his boy. Jack Bailey couldn’t help but crack a smile, appreciating that the older man was pulling out all the stops to make him feel good.

Mr. Charger’s tongue moved over Jack’s hole with expert precision, both tickling, teasing, and gently moving inside. Jack couldn’t help but moan, feeling his loins swell with excitement. He wanted to feel his grandpa inside him and to forget all about the letter. And Grandpa Charger knew that.

Pulling out his cock from his pants, the older man could sense the boy’s desire to submit. He needed to let go and think about nothing else but an intense pounding. He slid the tip of his member against Jack’s hole, feeling him come back on him ever so slightly, as if he was beginning to be penetrated with his ass.

Mr. Charger took off the remainder of his clothes, put a hand down on Jack’s smooth, youthful back, and plunged himself deep into his grandson’s guts.

Jack tried to contain his moans, not wanting to alert anyone nearby to the fucking occuring in his grandfather’s office. Mr. Charger, on the other hand, seemed to have no care in the world but his boy’s needs. He worked him slowly, fucking him with gentle thrusts at first, giving him a chance to get used to the older man’s thick, throbbing member. But once Jack Bailey fully relaxed, the older man held nothing back from his boy.

The first aggressive thrust was a shock. Jack did not expect to be so roughly fucked by the older man, but he was instantly grateful. He felt completely taken and dominated, feeling his bare cock move inside his hole and slam against his prostate. Jack stroked himself between the desk and his body, loving every hard push the older man gave him.

The furious pounding was almost more than Jack Bailey could handle, but he didn’t dare ask it to stop. He looked back at his grandpa, seeing the powerful, handsome, unstoppable man he’d always known and loved. And enduring the full force of his fucking, he knew he was special. He knew he was protected and cared for. That even now as he struggled to take the onslaught of deep penetrations, it was he that Mr. Charger was performing for.

Jack wanted to feel his grandfather breed him more than anything else he’d ever wanted. More than any job or trophy or approval. Knowing he could have his grandfather right there inside him, with him, injected him on such a profound, natural level… it was the ultimate prize in life…