Top Training | JACK BAILEY | Chapter 1

From the outside, Jack’s household seems perfectly ordinary. Close-knit, loving family with a handsome, all-star athlete boy. And in many ways, this is true. But what people might not assume is just how close-knit Jack is to the men in the family… particularly his grandpa, Lance.

Grandpa Lance has always taken a special interest in Jack. The young man’s bright, sunny smile always puts the older man in the best mood. For Lance, so much of his joy came from how much he reminded him of his son, Jack’s father.

Lance loved being there for his son when he was growing up. And back then, Lance was busy being a business owner and community leader. He didn’t have a lot of time for his son, something he deeply regretted. When Jack came into the picture, he swore to make sure Jack had all the attention he could ask for, giving him every bit of encouragement and advice possible.

Of course, Jack was much more than just his son’s kid. As he got older and developed into a young man, Lance couldn’t help but notice how handsome he was. Even sexy. Something about his wide-eyed innocence matched with his familiar good looks made Jack hungry for him in a way he hadn’t imagined.

Their first kiss came as a bit of a surprise. The two were embracing each other after a holiday when the two were uncharacteristically flirty and close. The rest of the family had started to go to bed, but Lance and Jack were up laughing and messing around, becoming unaware of the late-night hour.

It was quick at first, then the second was somehow longer and deeper. Jack had never kissed a boy before--or a man, for that matter--so he was naturally confused by all the emotions he was feeling. It felt nice. Strange and unexpected. He didn’t know if it was because it was his grandpa or because it was his first.

He couldn’t deny that he was attracted to the older man. How could he not? Grandpa Lance was the definition of silver fox, well built, successful, friendly, and warm as a wool blanket. He even smelled like firewood… something Jack had not noticed until that moment, but never forgot after.

The two went to bed separately, not going any further. The rest of the family didn’t know what happened, but Jack waited for the chance to kiss him again.

Months later, Jack found himself on the eve of a first date. He was excited and nervous, as young men are, sitting in his room and waiting for the day to carry on it’s slow march. He couldn’t get out of his head, thinking about all the ways he could mess up and embarrass himself. He was so distracted, he barely noticed Grandpa Lance enter his room.

He was dressed impeccably, clearly coming from the office after work. It wasn’t uncommon for Grandpa Lance to show up to the house, but very rarely did Jack and he find themselves alone. Lance closed the door behind him, locking eyes with his grandson, and feeling his chest fill up pride.

Lance said he heard about Jack’s date and wanted to give him a bit of pep talk. Jack’s face cracked the biggest smile, feeling his nervous subside with his grandpa there. Jack was expecting advice on how to open doors and be polite, but the handsome man caught him off guard by asking a direct question.

“Have you ever had sex before?”

Jack’s face flushed red. He didn’t know what to say that would sound right, so he just told the truth that he hadn’t. Lance smiled, feeling a mixture of relief as well as excitement. He liked being able to help his boy out with such a momentous occasion. And the idea that it was his first time only made it all the more special.

Lance took off his jacket, revealing his bulging muscles tightly wrapped in his fine, collared shirt. Jack never got over how beefy the older man was, putting many younger men to shame. Seeing him begin to unbutton his sleeves and shirt, Jack found himself at a loss for words.

“Do you want some pointers?” Grandpa Lance asked, already beginning to remove his clothes. Jack could hardly believe what he was hearing and seeing. It became pretty apparent that this was not going to be a usual birds and bees conversation, nor was it going to be purely theoretical.

Grandpa Lance told Jack to start by taking off his clothes, which the boy eagerly jumped to the edge of the bed to help. His fingers quickly and excitedly finished the last of the buttons and the dress shirt fell off with ease. As Jack looked up, he saw the beautiful spread of soft white hair across Lance’s muscular chest, his well developed pecs pushing out freely and making him look even bigger than before. As Jack’s eyes went wide and his mouth fell open, he took in the scent of that firewood… and he was in heaven.

With Lance’s permission, Jack took a handful of the older man’s member, still concealed in his underwear. It was big and warm, plenty thick and growing harder as he touched. Lance guided him to his nipples. Jack teased them before taking them into his mouth. His soft, full lips pressed onto them, feeling the silky fur of his chest caress his face.

Lance repeated under his breath “good boy, that’s my boy” as Jack navigated his body, seeing Jack’s cock begin to tent up his shorts.

Lance wanted to show Jack exactly what he needed to know. Taking off his underwear, Lance got up on the bed and spread his legs apart, giving Jack a look at his hairy, bare ass and tight hole. Jack gazed at the man’s backside, never having seen something so beautiful. Everything he’d seen in porn and in life was all smooth skin twinks. But here was a man like he’d never seen, in the flesh, and ready for him to explore.

Lance taught him how to rim his ass, relaxing and tightening his sphincter on the tip of the young man’s tongue, giving plenty of encouragement and guidance on how to properly loosen him up. Jack couldn’t believe he was tasting his grandpa’s hole, but everything about how it looked, tasted, and felt was amazing. He could have stayed with his face planted between his fuzzy cheeks for hours, but his throbbing cock was becoming too much to bear, and Grandpa Lance was keen to feel it deep in his hole...