She ran her thumbs back and forth over her sister’s nipples, then she pinched them. Madison had slid her hand back into her panties and was playing with herself.
“Come closer,” Ashley said softly. Madison leaned in, knowing what Ashley had in mind. Madison positioned herself on Ashley’s side. She sat more upright than Ashley so that her nipples were within reach of Ashley’s mouth. Ashley stuck out her tongue and flicked it up and down over Madison’s nipple before taking it into her mouth and sucking gently. She reached up and groped her sister’s other tit. Madison groaned and rubbed her clit faster.
“You can touch mine too, you know,” Ashley said. Madison squeezed Ashley’s boobs as Ashley continued to suck on hers. Ashley was also playing with herself at this point, rubbing her clit while her ass was plugged with the toy. A moment later, Madison scooted back and leaned down, taking Ashley’s nipple into her mouth. She reached over and played with Ashley’s other boob.
“Keep doing that while I make myself come,” Ashley groaned. She reached down and fucked herself with the dildo with one hand while she rubbed her clit with the other. It didn’t take long before she was about to come.
“Don’t stop sucking my tits,” Ashley cried. “I’m coming!”
Madison kept sucking and running her tongue all around Ashley’s nipple as her sister’s orgasm erupted. Ashley bucked her hips and continued fucking herself with the dildo as she came.
Once she was finished, she said “your turn”. Madison laid down and continued to play with herself. Ashley laid next to her and Madison’s nipple into her mouth. She sucked it gently, running her tongue around Madison’s areola and flicking her nipple with it.
“I’m gonna come, baby,” Madison moaned softly.
“Good girl,” Ashley cooed. “Come for your sister, baby girl.”
Madison cried out as she climaxed. She fucked her pussy wildly with her finger and massaged her clit while Ashley continued sucking on her left nipple.
“Oh my God,” Madison said through clenched teeth.
Once her orgasm finished, Ashley just laid down next to her.
“That was great,” Ashley said softly.
“No kidding,” Madison breathed. “Do you still have the dildo in your ass?”
“Yep,” Ashley laughed.
“That’s so hot,” Madison said.
“You’re welcome to use it anytime,” Ashley said with a wink.
Chapter 8 – Photoshoot
Brian and Madison play together.
I went over to Ashley’s house later that afternoon. We ate dinner together before Ashley left for work. She was closing that night so she wouldn’t be back for a while. I was just gonna hang out with Madison until she got back, although it was entirely possible that the three of us would “hang out” once Ashley got back from work.
Madison and I were sitting in the basement; she was sitting next to me on the couch. We had gotten pretty close recently. We were always good friends, but the development of the sexual component of our relationship had brought us even closer. We’ve also gotten to the point where we can essentially talk about sex and whatnot without it being awkward.
“So I have a random question,” Madison said.
“What’s up?”
“What’s your opinion on anal?”
I laughed. “Anal? Is there any reason you’re asking, or are you just curious?”
She answered my question with another question: “Did Ashley tell you about what happened earlier?”
“No, what?” I smirked.
“We were talking about how we can get Alyssa on-board with our ‘activities’ and we got horny, so naturally we masturbated together.”
“Obviously,” I chuckled. “Because it’s natural for sisters to get horny and masturbate together.”
“Of course,” Madison giggled. “And Ashley asked me about anal. One thing led to another and she ended up masturbating with a dildo up her butt.”
“That does sound like something Ashley would do.”
Madison laughed.
“Well, if you guys talked about anal, then Ashley probably mentioned that she and I do it a lot.”
“Yeah, she did,” Madison said. “She really likes it, I guess.”
“She does,” I smiled. “I’m a lucky guy.”
“You like it too then?”
“Duh,” I said. “I love anal.”
“What do you like about it? I’ve never done it before, but I’m curious if it isn’t obvious.”
“I think it’s hot,” I shrugged. “It looks hot.”
“Yeah,” Madison said. “I agree. I guess it’s a bit weird I’ve never tried it since I’ve been interested in it for a while now.”
“You think it looks hot?”
“I mean, yeah,” Madison said. “I watch porn too, you know.”
“Really?” I asked. “I guess I’m not surprised now, but before we all started, like, doing ‘things’ together, I never would’ve thought you watched porn or masturbated.”
Madison shrugged. “I masturbate at least a few times a week, usually to porn. And ‘anal’ is probably the kind I watch the most even though I’ve never done it.”
“Well, first of all, that’s really hot,” I said.
She rolled her eyes. “You’re such a guy.”
“And,” I said, ignoring her playful jab, “you should really try it sometime. It can feel really great.”
“Apparently,” Madison giggled. “Ashley seemed to be having a great time earlier.”
“Right. It’s actually been a little while since she and I did anal though, maybe a week or so. Usually we do it a couple times a week.”
“Do you have a favorite position for anal?” Madison asked.
“I like doggystyle the best, I suppose,” I said.
“Because of the view?”
“Mhm,” I 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 I can’t really get my booty fucked, but Ashley offered to let me use her dildo.”
“That would work,” I 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 said, 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 I 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 I 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 I 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 I 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?” I said, uncertain about what exactly she was suggesting.
She leaned forward and spit onto my cock a couple of times.
“Oh,” I 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…” I began. “Based on how good your boobs look in a bra…”
Madison blushed and giggled.
“I can only imagine how nice they must look unclothed,” I concluded.
Madison smiled. “Yeah, well Ashley really seemed to enjoy them.”
“Exactly,” I said.
Madison looked like she was contemplating something for a moment. After a brief pause, she pulled up the shirt she was wearing and then the bra underneath it. She left the two bunched up above her tits. My jaw dropped. Madison laughed. “You literally have your dick out in front of me. I guess my tits aren’t really that big of a deal.” she said, shrugging.
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