Jockstrap Shopping (Pt 2)

Read Pt 1 here 

I beat myself up about it sometimes, because if Angela ever found out I’d blown her son, Trevor, well...it wouldn’t have gone well. But the next time we all three of us hung out – at a picnic at Angela’s house – everything seemed kosher enough.

There was Trevor, looking more swole than I’d ever seen him, in a backwards ball cap, tank top and athletic shorts. He greeted me with a huge hug. I guess I’d worried that keeping a secret would fuck with him somehow, but if anything he appeared more relaxed, and when talk turned to his new girlfriend I wasn’t surprised. Though I did notice he was calling me “Mike” now and not “Uncle Mike.”

Angela was the one who insisted Trevor give me a ride home.

“He’s on the way!” she insisted to her son. Trevor shrugged and agreed. We headed to his car and I got in the passenger seat. I asked him how football was going.

“It takes up all my fuckin time,” he said. I was still getting used to him swearing around me. “I barely get to see my girl,” he added, and glanced at me. I changed the subject, but when we got to my house he asked to use the bathroom. I had a sense where this was going and almost told him no. But then I though: he wants it. So do I. Why not? I waited anxiously while he used the bathroom and when he came out I was cleaning up the kitchen. I turned to him and he had the hugest hard-on in his shorts.

“Would you want to blow me again?” he said. I sighed. The guilt I’d felt intermittently over the last few weeks had been real. But equally intense was the memory of how turned on he’d been, how he’d moaned when I slid my tongue in his beautiful ass, how much hot teen cum he’d unloaded down my throat. It had taken over my jack-off fantasies.

“Let’s go in the bedroom,” I said. Once we got there I saw how nervous he was. I smiled at him and he smiled back, then I lifted off his shirt and felt his pumped-up body.

“You look so good,” I said.

“Thanks,” he said. I reached for his waistband and lowered his shorts. He wasn’t wearing any underwear and his big boner heaved out, a drop of precum at the tip. I looked up at him as I got on my knees and slid it into my mouth, all the way until my face was in his trimmed pubes.

“Goddamn you suck so good,” he said as I bobbed away.

“Better than your girlfriend?” I said.

“Definitely,” he said. I started to turn him around.

“Fuck yeah,” he said, and braced himself against the bed, perching out his perfect, muscled ass.

“Bet she doesn’t do this,” I said, and dove my face inside, tongue searching out his hole. I pressed it into him and he groaned.

“No way man, you’re the only one who’s ever done it...feels so fuckin good,” he said, voice getting high and reedy as I tongued him deep. I had him get up on the bed on all fours and stroked his cock as I ate him out. His ass was just pristine, firm and round with the slightest brush of hair around his pucker.

Already it felt different from last time, like we both wanted it to last. I was keeping him on edge while I licked his hole and his moans kept getting more intense. I decided to test the waters and put the tip of my finger to him. He backed up on it – his ass just swallowed my finger. So then I was massaging his prostate and sucking him from below.

Then, just when I thought he might cum, he got up and grabbed me and started making out with me and grabbing my ass.

“I wanna fuck you,” he said in my ear. I was stroking his cock and he started licking at my neck, fingers digging into my jean-clad ass crack.

“Are you sure?” I said, and he responded by shoving his tongue in my mouth. I told him I needed a minute and went to the bathroom to clean up real quick. I looked at myself in the mirror – a thirty-something guy about to give it up to a kid half his age, someone I'd known since he was a child. My cock was so hard. When I came out he was laid back on the bed with his arm behind his head, stroking his cock and ready.

I lubed him up and straddled him. It was difficult to look him in the eyes as I took him in my ass for the first time. It had been a while since I’d gotten fucked – never mind with a cock that big and thick – so it took a minute for me to get used to it. But my boner never went down and when I started bouncing on his rod he reached for mine and stroked me.

“Goddamn that’s some good ass,” he said. The dominant stance he was taking was such a turn on – it was a side of him I’d never imagined. Once we got into it he wanted to fuck me from behind. Then on my back. I let him plow me for over an hour, raw, in any position we could think of. We made out and edged and when he went to cum inside me I didn’t protest. He held tight to my hips and I felt his cock pulse as he shot his huge load again, this time deep inside me. A few moments later, as his cock still pulsed in me, I stroked myself to my own orgasm which went all over his hard tits and stomach.

Then I fell on the bed next to him and caught my breath. I felt the guilt creep in. The first time I’d been able to tell myself It was just a blowjob. Not the smartest decision I’d ever made but not a huge deal, either. But now we’d fucked – had sex, made love. His load was dripping out of me and now he had to head back to his mom’s house.

“Don’t worry, I won’t tell her about this, either,” he said, which broke the tension a bit. Then we talked – about the bisexual desires he’d had since he was nine, and how he’d always found me attractive. That he’d gotten head from a boy in his calculus class a year ago but other than that he’d never had a chance to explore it. He said he was grateful that he could do it with me.

“Is it hard, keeping it a secret from your mom?” I asked. He scoffed.

“I don’t tell her half the shit I do,” he said. That made me feel better. We got dressed and then I saw him to the door.

“Thanks Uncle Mike,” he said, and gave me a kiss as he headed out to his car. Then, just before he got inside, he turned to me and smiled the sheepish, charming smile I’d known of his since he was a boy.