I Stuck My Thumb in My Friend's Ass - Part 2

Everyone is 18.  This is fiction.

“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.

I lubed up my thumb and approached his ass again. He held still and braced for my re-entrance to his hole, and I spread his cheeks, inspecting his hole more closely, because why not. It was pink and pleasant looking, with just a slight ring of hair around it. His cheeks were a meaty handful, and I kind of wanted to use them as a pillow. When did we cross this boundary? I thought to myself, Maybe when I shoved my thumb in his ass. I kept his cheeks spread as I put my thumb back inside him. He groaned when I did it. 

“I didn’t know that feels so good bro.” He said, “Go deeper, you’re pushing a button inside me.”

“Wow,” I said. This was turning out to be fun. He started humping the toy again with some rhythm, while I just played with his ass and had fun with it. I sat on his legs behind him, and dug my right thumb in as much as it would go. I twirled it around and watched him squirm. I paid attention to what made him react. When I got my second thumb inside and stretched him out a bit, he hissed, so I slowed down, but kept pushing the limits. He started to moan louder and ask for me to go deeper, but there was only so far my fingers and thumbs could go. 

It hit me that I was sitting here with lube, and a big boner, and a friend who was begging me to stimulate his ass deeper and deeper. Why not had turned out to be the theme of the day, and I poured some lube out on my cock.

–

I rubbed the lube into my shaft, up and down a bit, while keeping a thumb in his ass, and pressing down on his “button.” His moans got more guttural, and his hips thrust more firmly into the fleshlight. When I finally got up the courage, I rose to my knees and leaned forward until my cock rested on his hole. Tobi didn’t look away from the porn on the TV, which was back to regular straight anal videos. I saw him brace himself, so he knew what was coming, and he wanted it, but didn’t want to say anything. I leaned forward for balance, and my face ended up right next to his ear. I heard him take a deep breath and hold it, and then I inserted the head of my cock.

His cheeks squeezed my cock reflexively, which felt good since they were lubed up and squeezing the shaft of my cock. His hole was so warm, I had never felt something like this on my cock before. As I pressed in slowly, he finally released his breath in a long sigh.

——

I started fucking him harder and harder, and his whole body gyrated with my rhythm. His cock was in the fleshlight, and my cock was deep in his hole. My ass bounced up and down and the front of my whole body slammed against him making a clapping sound. I was so lost in the moment I stuck a finger in his mouth, and he sucked on it reflexively. I grabbed him by the hips and thrust firmly, cumming inside him. When I pulled out he moaned, then turned on his back. I grabbed the fleshlight and jerked him off rapidly and he came in about 10 seconds. I watched as his ass and taint pulsted with his ejaculation. I lifted the toy off his cock and watched it drip back down onto him. He was out of breath and laid his head back. 

“What the fuck just happened?” He asked between breaths.

“Cool new way to get off.” I said. I watched as my cum leaked out of his ass onto his cheeks, and I threw him a towel.