I Stuck My Thumb in My Friend's Ass - Part 1

Everyone is 18. This is fiction.

Here we were again. Just taking turns bouncing a fleshlight on our cocks. Ever since we got the toy a few weeks ago, we had done little else when we were together. Tobi and I had been friends forever, and never hid much from each other. Ever since we first compared cocks and I saw how big he was, I was transfixed with his cock. Not that I was gay for him exactly, but I always loved when he would whip it out. And, I swear it’s gotten even bigger lately. 

So we were doing our normal after-school routine when his parents were still at work. We busted out the porn on his big TV in his room, and rubbed ourselves til it was time to get naked from the waist down and pull out our fancy pocket pussy. Tobi was basically rich so he could get whatever he wanted. Our bare asses would get some sweat on his bed but he never seemed to care.

“I’m gonna mix it up today.” He said as he grabbed all his pillows and made a pile on the edge of the bed, securing the fleshlight underneath and holding down the pillows with both hands. I saw what he was going for.

“Nice.” I commented, and watched as he laid across the bed, and fumbled with his cock until it entered the toy under the stack of pillows.

“Fuck yeah” he said when he achieved penetration. He fixed his eyes on the TV, with some slut on her back taking two dicks at once in her pussy. 

I glanced over at his new technique. He was humping down into the fleshlight. It looked fun, and you actually got to thrust forward into the thing, rather than just jerk yourself off with it. I wanted to try. But, from this angle I noticed his ass for the first time. 

“You actually have a nice ass,” I said, “It bounces like a girl’s. And you have like basically no hair, except a bit right here.” I reached over and poked his little pink hole with my index finger. His hole puckered and he squirmed immediately and fell forward laughing.

“Bro that felt funny but not bad.” he said. 

“Fag” I said, chuckling at him. He really is cute, I thought, in a no homo way I assured myself.

Then he continued back to his slow, rhythmic humping. I’d never thought I was gay before, but I couldn’t look away as his hole winked every time his cock pulsed, and the tight cheeks on his white little ass jiggled ever so slightly when he bounced on the fleshlight. I was stroking my cock out in the open, and I guess Tobi felt I deserved a turn on the toy.

“You want a go on this? I don’t wanna finish yet.” He asked without looking at me.

“I’m actually good back here.” I said, eyeing his ass.

He sank his thick cock balls deep into the toy and held it there, then grabbed his phone to put a new video on the TV. I could see his sizable ball sack hanging down between his legs. He chose a new anal creampie compilation on the front page of our favorite porn site. He started thrusting again, really slowly, clearly edging in the pocket pussy. 

Suddenly in the compilation a pegging video appeared. Some slender college guy was having the time of his life getting fucked in the ass by a girl with a thick dildo strapped onto her. I raised an eyebrow and looked over again at Tobi. He chuckled, but didn’t reach for his phone to change it. I got turned on thinking of one of us getting pegged. Why not, I thought, maybe it would be fun.

“Would you try that?” I asked him.

“I’ve heard it’s a lot of fun,” he said, “maybe.”

I was so turned on today, I decided why not. Before I could talk myself out of it, I stuck my thumb in my mouth and got it sopping wet, and just as the guy on screen started cumming hands-free from the dildo pumping his ass, in one swift motion I shoved my thumb into my friend’s ass, and pushed down toward his cock from the inside. To my surprise, he froze still, and I felt his hole contract on my thumb in pulses.

“I can feel your heartbeat.” I said, amazed.

“No bro, I’m cumming.” He said breathlessly. He started to jerk his hips sporadically, and I just held on, keeping my thumb in place. His warm, wet hole honestly felt nice, and apparently he was loving it.

When he finally stopped pulsing, he fell face forward and breathed hard like he was catching his breath. I slowly pulled out my thumb, and he involuntarily moaned lightly.

“What the fuck was that? What did you shove in my ass?” He asked, still catching his breath.

“My thumb, dude.” I said, giving him a thumbs up with my wet digit I had just pulled from his hole.

“That’s gay bro,” he said, and I started to worry. Then he continued, “but do it again.” He got up on all fours, his ass facing me and his cock still inside the pocket pussy. He started to gently thrust again. He had never gotten soft after cumming, so I guess he was ready for a classic double-creampie.

“As you wish” I said, and grabbed the lube from the fleshlight box and got ready for round two.