DILF Chaser

I knew he was deciding whether it was worth the risk. I think it was the way I smiled up at him shyly that helped him decide. He said, “fuck it,” and took me by the arm to lead me to the storage room. He must have read my mind, because ‘fuck it’ was exactly what I was hoping for.

The stub of Grandpa's cigar never left his mouth the whole time he was giving it to me up the butt. I already knew he wasn't gong to kiss me, it was a rule he learned when he was in the Marines.

Dad apologized for getting so carried away, but I told him I hadn’t really expected him to stop with just the tip anyway.

He could see I wanted to, but I was also afraid. So, he just took me by the arm and said, "C'mon, it won't be so bad, I'll go easy on you." And he did. At first.

Our neighbor, Mr. Yeager likes big cigars. In fact, everything about Mr. Yeager is massive. His massive cock stretches out my little pink asshole so much, I can’t hold his massive load in me. He orders me to lick up the spillage so it won’t stain his patio.

I politely asked him if I could get at the hair dryer to his left. He moved just enough for me to squeeze my hairless buttocks between his bulge and the sink. The sound of the hair dryer covered the sounds of our grunts and moans. The mirror allowed me to see the look on his face when he nutted. And my parents wonder why I go to the gym so much.

When Uncle Jack wants to take a nap, he tells me how long to let him sleep.  I awaken him gently, by pushing my face between his hairy buttocks.  He’s always ready for another round after his nap.

I ran around the corner and almost jumped head first into the sun shelter.  I halted myself when I realized that it wasn’t the one my family had reserved.  I apologized profusely, saying I thought I’d find Dad in here.  “Crawl in, kid, maybe you did,” he said in a deep rumble.  I asked him to hold that thought, found my family and told them I was going to walk down the beach a ways.  Then I went back and let him adopt me, hard and deep,  for a couple of hours.

Our neighbor was reading on his terrace when I interrupted him.  I asked him respectfully to help me out, but he said he had plenty of butt boys already and didn’t feel like breaking in another virgin.  So, I dropped to my knees and begged.  That seemed to do the trick.  Apparently he saw something in me that was worth developing.  Or as he put it, “Subs like you bring out the artist in me.”

I asked our neighbor if it was okay if I swam naked.  “Sure, kid,” he said, “but aren’t you afraid that will make you somewhat vulnerable?”  I told him I was sure he wouldn’t do anything I didn’t want him to do.  “Well, there’s one good way to test that theory, show me that ass and let’s see if you like what I do to it.”:  I did like what he did to it, after it stopped hurting so much.  

Dad opened a private lounge in his cigar shop for special customers, like Mr. Hawkins.  I serve as attendant in the private lounge five nights a week.  On those nights the private lounge is packed, and so is my ass.  Dad’s appreciating the advantages of having a fag son.

“Nah, your head would get in the way of the TV.  Here, just work on my armpits until half time.”  Dad prefers a good football game to head.  Either that, or he knows he can always get head from me, so why miss the game?

I know Granddad was awake when I was climbing onto the couch.  But he didn’t open his eyes until I was fully impaled.  He smiled and tickled my navel.  “I’m tickling your little belly button from both sides of it, aren’t I little buddy?”

The man who picked me up in the park flashed his hairy chest and said, “Here, kid, this ought to hold you till we get to my place.”  Actually, it just made me more impatient.  He probably knew it would.

I looked over my shoulder to see his reaction.  “Huh.  You’re completely smooth.  Yeah, I think I’d like that,” Uncle Andy said.  It was my first time ever, it was just his first time with a guy.

Would love to get lost at sea with this silverfox

It was a little game Granddad and I played.  He’d take us away from shore and announce that now that we on the high seas, his word, as captain, was law.  I’d get down on my knees and ‘swab the deck.’  After that, it was time for him to ‘inspect’ my poop deck.