Mr Young's Friend

A few days after Mr Young and I fucked, I got a friend request from Mr Young’s Friend on Facebook. I had seen them in pictures together and Mr Young’s Friend was definitely cute and also very stylish. We began talking on Facebook. He certainly wasn’t as forthcoming as Mr Young and it took him about a week to mention that he knew about what had happened between me and Mr Young.

He was very curious about it and was asking all sorts of questions which of course I answered before we started speaking about his sex experiences. He’d had sex a few times with some of his friends but had only ever topped, including with Mr Young. Then he said he wanted to try bottoming and hinted at the fact that he wanted to try it with me. As much as I loved the idea of it, I didn’t think that it would actually happen because I assumed Mr Young’s Friend was too shy. That was until he asked if he could come over.

I told him that we should probably go out for a coffee first and so we did. He was VERY shy and it took him a while to warm up and feel comfortable, but once he did he started to flirt with me. Mr Young’s Friend was blonde, tanned and had these really big brown eyes that when I stared into them, I couldn’t help but get turned on. Once I had finished my two coffees and he’d finished his one, I invited him back to my apartment.

After a little while of watching TV, we started making out on the lounge. He was quite a good kisser – not as good as Mr Young but good enough! Not long after that, I felt his cock which was already rock hard in his pants so I decided to pull it out and suck. It didn’t take very long before I could feel he was about to cum so I stopped and pulled out my cock for him to suck.

He was definitely not a bad cock sucker at all. He’d get better with a bit more experience but I was definitely enjoying watching him work my cock and gag occasionally while trying to take more into his mouth.

“Do you wanna take this further?” I asked.

“Yes,” he replied.

“Are you absolutely sure that you want to bottom?”

“Yeah,” he said. “I’ve been wanting to do it for ages.”

So I decided to make it as easy as possible for him for his first fuck, unlike my first fuck which was just forced in. I warmed him up by fingering him a little, then two fingers, then three. He was so tight! I couldn’t wait to get my cock in there. Then I pulled out my two dildos. One was quite skinny and the other had a head which was fairly skinny and an end which thickened out as to make easy anal entry. I worked on him with the small dildo and then the bigger dildo. He had a bit of trouble with the bigger dildo and looked like he was in a bit of pain.

“You okay?” I asked.

“Yeah,” he said shortly.

After pushing the bigger dildo in as far as I thought it could go, I pulled it out and got my cock ready to go in.

“You sure about this?” I asked.

“Yes!” he assured.

I positioned my cock over his hole and then slowly pushed it in which was met with a moan. I wasn’t quite sure if it was pain or pleasure but I kept slowly pushing until I was all the way in with him moaning and wincing the whole way.

“The worst is over,” I said.

“Okay,” he said.

Then I started to slowly pump away – very slowly at first! Before too long, the wincing went away and his cock became hard – he was obviously enjoying it. I started to pump faster and then harder and before long I was fucking him and he was taking it like a pro. He started to jerk off and was moaning seriously loudly with pleasure and was grinding his hips around my cock and the bed.

It didn’t take too long for him to cum and the sight of the cute boy cumming with my cock up his ass for the first time drove me crazy and I cummed while inside him.

I flopped onto the bed afterwards absolutely exhausted.

“That was amazing,” he said.

“So you liked a cock up your butt?” I asked.

“Oh yeah,” he said.

It was amazing breaking in Mr Young’s Friend and it seemed like he enjoyed it too!