Read Story: SEASON 1 EPISODE 23

"Do you have a favorite position for anal?" Madison asked.

"I like doggystyle the best, I suppose," I said.

"Because of the view?"

"Mhm" said. "It's hot being able to watch your dick go in and out of the girl's butt, to put it bluntly."

"I agree," Madison chuckled. "How much different does Ashley's butt feel compared to her pussy?"

That was quite the question, but nothing too out of the ordinary for us at this point. "It's tighter right around the entrance, like her butthole itself is super tight, but inside isn't as tight as her pussy."

"Hmm." Madison thought for a moment. "Well, obviously Alyssa doesn't have a dick so can't really get my booty fucked, but Ashley offered to let me use her dildo."

"That would work," said. At this point, I had a very obvious tent in my pants. Talking about anal with Madison was driving me crazy. "Putting your own sister's dildo in your butt is pretty crazy, though." I smirked.

"So is watching your sister give her boyfriend a blowjob," Madison laughed. "And letting her boyfriend come on your face. In fact, I'd argue that those two are even crazier."

"Fair point," I said, chuckling.

"Feel free to take care of that, by the way," Madison sald, gesturing towards my crotch. "I guess talking about anal with me has really worked you up, eh?"

"Just a bit," I laughed. I pulled my shorts and boxers down. My fully-erect cock sprung up, pointing at the ceiling. I grabbed it at the base and began to slowly pump it up and down.

"I'm surprised Ashley can take all that up her ass, Madison said, watching me stroke myself. "You're definitely bigger than the dildo she uses."

"Well," I said, "we usually warm her up a lot."

"What's your 'routine?"

I began to massage my balls gently as we talked. "I usually eat her ass first. Then, I'll use one finger, then two, then three. Then we use that dildo. Once she can handle the dildo, she'll either blow me or I'll fuck her pussy until I'm wet enough. Then I fuck her in the ass."

"Oh gosh," Madison said. "I don't know if would want my ass eaten. The rest of that sounds lovely, though."

"Ashley loves having her ass eaten," I said. "She usually comes from it. I'd try it at least before writing it off." I continued to stroke myself as we talked.

"Well, maybe I'll try a finger next time masturbate. And then I could try Ashley's dildo."

"My dick is always available too," I said with a grin. I was only really half-joking, though.

"I don't think I could take all of that." She gestured at my dick again. "Not in my ass, at least."

The fact that she sort of implied the idea of us having regular sex made my head spin. "Well, if you ever get the point where you can handle her dildo comfortably, you know where to find me."

Obviously I didn't expect her to ever take me up on that offer, and I'd have to make sure Ashley was okay with me butt-fucking her sister. Somehow didn't think that would be too much of a problem at the rate things were currently going, though.

Madison watched me jack off for a moment before speaking again. "I don't even know if I like it up the butt yet." She was blushing pretty hard.

"Well, I would just start with a finger, like you said." I smiled.

"Fair," Madison said, sighing. "I think will. My poor little butthole isn't gonna like it when I try to get her dildo up there, though."

I laughed at her comment. "Start small," I shrugged.

"Do you want some lube for that, by the way?" she asked.

"Uhh, sure?" said, uncertain about what exactly she was suggesting.

She leaned forward and spit onto my cock a couple of times.

"Oh," laughed, "thank you." I stroked myself a bit faster now, spreading her spit all over my dick.

"Is that good?"

"Yeah, this feels way better, thank you."

"No problem," she smiled.

"So did anything else of interest happen when you two mastubated earlier?" I asked.

"Well, yes actually," Madison said. "I showed her my tits for the first time."

I stopped stroking myself.

"What?! Really?"

"Mhm," Madison laughed. "Aaaaand I sorta let her play with them. Aaand suck on my nipples."

"Holy shit." I resumed stroking myself, causing Madison to laugh.

"And I sucked on hers while she came," she smiled, knowing she was driving me crazy.

"Holy FUCK. That's so hot, Madison."

Madison laughed again. "If you told me a few months ago that I'd be letting my sister suck on my tits while I masturbated, I would've thought you were insane. But it was a lot of fun."

"Well, both of you have an amazing pair of tits so I can see why you had so much fun."

"Both of us?" Madison smirked. "You haven't even seen my tits."

"Well, I mean..." began. "Based on how good your boobs look in a bra..."

Madison blushed and giggled.

To Be Continued...