It was a week since we had all jerked off together. We had been too busy to do anything like that again. I had walked in on James pumping his cock since then. He had been lying on top of the covers on his bed. He had his legs spread wide exposing his naked body. I had gone in to wake him up because, judging by the time, he had slept through his alarm. I just told him the time and left, smiling. We were all moving around one morning getting ready for work or uni when I said, “We should all just take tomorrow off. Call in sick or whatever. The last week has been so busy, we need time to unwind”.

“Good idea” Ted responded. Everyone seemed enthusiastic so we all agree to take the next day off.

The next morning everyone slept in, grateful for the break. I awoke early than everyone else and cooked a full breakfast for everyone. At about 11 James, Matt and Ted stumbled out of their rooms in the sleep clothes, or lack of. Ted was wearing a dressing gown over his clearly naked body. James was wearing a pair of boxers, Matt was just in a pair of tight boxer briefs. I was wearing a loose pair of gym shorts with nothing underneath. “How did you guys feel after last week?” I said.

“God that was so good” Ted said through a mouthful of toast.

“Yeh you certainly looked like you had a good time” James remarked smiling.

“Have you guys ever tried anal masturbation?” Ted asked. James and Matt said no while I said that I had a couple of times but could never get it right. “I can…you know…show you guys” Ted said slightly awkward.

“That would be awesome” Matt said, clearly eager to improve his orgasm. We finished our breakfast with Ted trying to explain the best way to anal masturbate. We decided there was no other way but for him to actually show us. We walked casually to the living room again, James, Matt and myself sat on the couch like we had done the other week. Ted, however, sat on the coffee table in front of us.

He shrugged of his robe, the rest of us were still in our sleep wear. Ted put on leg up exposing his whole and said, “This position is easiest as it opens up the hole more. You take some lube and put it on your finger” Matt passed him the bottle of lube and Ted massaged some onto his finger as well as his cock. He got his cock erect, making it point up and giving us a clear view of his ass. He took his wet finger and circled his whole gently. The slowly he pushed it in his face show an expression of pure ecstasy. “Then you just sort of slide it in as far as you can go,” He said demonstrating, “I find it easiest o curl my finger a bit and find the prostate. Once you find it rub it. Some people can orgasm by just doing this but I like to stroke as well”. He continued to massage his prostate while precum oozed out of the tip of his big cock.

Simultaneously we all stripped off and passed the lube between us. We put our legs up and gently inserted our fingers into our asses. There was a chorus of moans and grunts as we entered our asses. We did as Ted said for a little bit until I said, “I don’t think I can find my prostate”

Ted said, “It’s really hard to describe…umm...look I’ll show you where yours is.” He took his finger out of his ass and knelt down in front of me. I took my own finger out of my ass. Ted put some more lube on his own and gently nudged my asshole, “Are you ready?” he said.