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Introduction:

Ashley introduces Madison to the world of anal play. Madison and Brian play together.

Chapter 7 - Anal Ashley

Madison finally sees every part of her sister’s body.

As far as I know, nobody played with each other for a few days after that. We were all busy with work or school so we just weren’t all available at the same time. A few days later, however, Ashley and Madison had some down time and were once again hanging out alone in the basement. It was mid-afternoon on a Thursday.

“I think Alyssa is coming over again on Saturday,” Madison said. “If you wanna try to do anything with her, then that would probably be a good time.”

“Alright,” Ashley said, smiling. She was excited. “That works out because I don’t think Brian and I are hanging out that day, and I wouldn’t want him to have to knowingly sit out out like that.”

“Right,” Madison said. “I’m sure Alyssa would welcome having him around once we get things moving though, so-to-speak.”

“She doesn’t exclusively like pussy, eh?”

“Nope,” Madison laughed. “She loves dick as much as anybody else.”

“Well, that’s good,” Ashley said. “I’d love to play with Brian in front of both of you.”

“That would be hot,” Madison said in agreement.

“So what do you think we should do on Saturday then?”

“I’m not sure exactly,” Madison said. “I honestly think she’ll bring up the fact that we heard you and Brian having sex, especially if she’d had something to drink. Could you pick up a bottle of wine after work?”

“Oh, that’s a good idea,” Ashley grinned. “I get so horny when I’m drunk.”

“Me too,” Madison giggled. “So does Alyssa. Do you just want to masturbate together?”

“Yeah,” Ashley said. “You think this will work?”

“Mmhm,” Madison says. “Trust me. One glass of wine and Alyssa is all over me. She’ll definitely bring up the fact that she heard y’all having sex.”

“Awesome,” Ashley grinned. “I’m so excited; this is going to be so much fun!”

“Me too,” Madison said. “I can’t wait!”

“If all of this goes well, then maybe the next time, you and Alyssa could give each other head in front of me like Brian and I do in front of you.”

“I would love that,” Madison smiled.

“Sweet.” The two sat without talking for a moment before Ashley broke the silence. “You said Alyssa has had a threesome before, right?”

“Yeah, she’s had a few. Why? Because what we’d do is sort of like a threesome?”

“I’m just curious,” Ashley said. “Do you know what the composition was? Like was it with two girls and a guy or two guys and her or…?”

“She’s done both,” Madison said. “I actually asked her which she prefers and she said it just depended on what mood she was in.”

“So she had a threesome with two guys?”

“Yes,” Madison laughed. “Why?”

“No reason, really. I’m just wondering. Do you know what they did? The one with two guys, that is.”

“Uh,” Madison blushed. “Yeah. She gave one head while the other did her from behind, and then they double-penetrated her.”

“Holy fuck,” Ashley said. “That’s crazy!”

“That’s what I said when she told me about it,” Madison laughed again.

“Would you ever do that?”

“Which?”

“Either. Double penetration or giving one guy head while another does you from behind or whatever.”

Madison thought for a moment. “I’d definitely try giving a guy a blowjob while another one had sex with me. I’m not sure about being double-penetrated, though. That seems like a lot.”

“Why not?” Ashley asked. “It would feel so good!”

“Would it? I’ve never done anal so I wouldn’t know how that part would feel.”

“You’ve never done anal?”

“Nope. I think it’s hot though. Have you?”

Ashley laughed. “Yeah, Brian and I do anal at least once a week.”

“Really? That often?” Madison breathed. The idea of her sister taking it up the butt was incredibly arousing for her.

“Oh yeah,” Ashley said. “I also just like having my ass played with. Like Brian will put his thumb in my ass or I’ll wear a buttplug during regular sex sometimes.”

“I guess I’m not surprised,” Madison shrugged. “One guy I was with wanted to put his thumb in my butt, but I wasn’t comfortable with it at the time.”

“Oh man,” Ashley said. “You really missed out. It feels so good and really it’s just hot.”

“Gosh,” Madison said. “Well, maybe I’ll see if Alyssa wants to try it. She’s expressed interest in it before.”

“Yes girl,” Ashley said. “Have her eat your ass. Or have her put a finger or two in there next time she’s giving you head.”

“I think I might,” Madison blushed. “Although I don’t know about having her eat my ass.”

“You should at least give it a try, Madison. It really feels a-mazing. Nothing beats an actual dick in the ass, though,” Ashley groaned. “Gosh, I wish Brian were here.”

“Don’t you have a dildo?” Madison asked. “Why don’t you just use that?”

“Like right now?”

Madison shrugged.

“Would you wanna watch me?” Ashley asked, her eyes lighting up. There was excitement in her voice.

“Sure,” Madison said, chuckling at Ashley’s obvious excitement.

Ashley stood up. “Let’s go to my room.” Ashley turned and went towards her room. Madison followed.

They walked through the doorway. Madison shut and locked the door behind them before sitting down on the corner of the bed. Ashley was digging around in her underwear drawer. She pulled out a simple-looking gray dildo. It was modest in length and had a pair of balls on the end. She also took out a bottle of lube. Ashley hopped on the bed and sat against the headboard.

“Are you gonna play with yourself too?” Ashley asked.

“Of course,” Madison laughed.

“Great,” Ashley said happily. She took off her t-shirt and threw it on the ground next to the bed before reaching back and unhooking her bra, which quickly found its way to the floor next to the discarded shirt. Madison drank in the sight of her sister’s big tits. Ashley’s nipples were already quite hard.

As Ashley began to slide her shorts off, Madison began undressing. She took off her shirt and pants, tossing them on the ground near Ashley’s clothes. Ashley was now naked except for her thong, and Madison was wearing just her bra and panties.

“Are you ready to see my pussy again?” Ashley giggled.

“Absolutely.”

Ashley hooked her thumbs into the waistband of her thong and slid the garment down her thighs. After tossing her underwear on the floor, she leaned back and spread her legs, giving Madison a good view of her vagina.

“I’m just gonna masturbate normally until I’m warmed up,” Ashley said, tracing her fingers gently up and down her slit.

Madison nodded, sliding her own hand down into her panties. She began to play with herself. Ashley followed suite, rubbing her clit and moaning softly. The two sisters watched each other as they pleasured themselves. Madison’s eyes traced over Ashley’s body, moving from her sister’s tits to her pussy and then back again.

Ashley slowly slid her index and middle finger into her pussy. She began to fuck herself gently. Madison moaned.

“Okay, I think I’m ready. Usually I just start with a finger and go from there.” Ashley scooted forward, moving towards Madison and away from the headboard. She then leaned back, keeping her legs spread but her knees bent.

“Jesus,” Madison said. She was incredibly turned out by the sight of her sister splayed out in front of her like this. She’d also never seen Ashley’s asshole before. She liked it.

“Do you like the view?” Ashley giggled.

“Yes,” Madison groaned. She slid one of her fingers inside her own pussy.

“How’s my asshole look?”

“Great, actually,” Madison smiled. “Honestly your butthole looks so hot.”

“Thanks,” Ashley laughed.

Ashley slid her index finger in her mouth, sucking her pussy juices off of it. She got it completely coated with saliva. She moved it down and held it at the opening of her puckered asshole. Madison watched as Ashley’s finger slowly disappeared inside her asshole. Ashley moaned. Once she was knuckle-deep, she began to slide back out. She immediately inserted her middle finger too, slowly sliding both fingers in until they were both knuckle-deep.

“That’s so hot,” Madison breathed. “Does it feel good?”

“Oh yes,” Ashley moaned softly. She began to slowly finger-fuck her ass.

Madison paused for a moment before sitting up. She reached back and unhooked her own bra, slipping it off and tossing it behind her.

“Holy fuck, Madison,” Ashley gasped. She stared at her sister’s unclothed tits. They were almost as big as hers. Her nipples stood completely erect on each nipple, surrounded by a faint pink areola. Madison reached up and pinched her nipples.

“If I get to see your asshole, then you should at least see my tits,” Madison shrugged.

“They’re gorgeous,” Ashley said.

“Thanks, Ash,” Madison smiled.

“I think I’m definitely ready for the toy. Can you get it wet for me?”

“What do you mean?”

“I don’t know,” Ashley said, “just suck on it and get it wet.”

Madison hesitated briefly, but then went with her sister’s idea. She picked up Ashley’s dildo and brought it to her lips. She slowly took it into her mouth. It had been a while since she’d sucked a dick before.

“That’s hot,” Ashley smirked. “Maybe I should let you suck Brian’s dick sometime.”

Madison slurped on the fake cock for a moment before taking it out of her mouth. “That would be fun,” she said before continuing to suck on the toy. Once it was thoroughly coated in saliva, she took it out of her mouth and handed it to Ashley.

“Thanks,” Ashley said. She took her fingers out of her ass and held the toy at the opening to her hole. Madison watched as Ashley’s asshole slowly opened as she pushed the dildo inside her. Ashley groaned as the toy filled her rectum. She slid the dildo in until the balls were against her ass cheeks.

“How does that feel?” Madison asked.

“Full. Amazing,” Ashley replied. “Come over here.”

Madison crawled over to her sister, sitting down next to her.

“May I?” Ashley asked, gesturing towards Madison’s boobs. Madison nodded. Ashley reached up and squeezed her sister’s left tit gently. She ran her thumb over Madison’s nipple, eliciting a small moan out of her sister. Ashley grinned and did it again, eliciting another moan.

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.

“Uh yeah, sure,” I said, staring at her tits, my mouth still slightly agape. “They’re gorgeous.”

“Ashley’s are bigger,” Madison shrugged. “But I like mine. I think my nipples are cute.”

“Your nipples are very cute,” I smiled. My cock was throbbing at this point. I had slowed down significantly to prevent myself from popping off already. “You really let Ashley suck them earlier?”

Madison scooted closer to me. “Mhm. It felt really good.” She squeezed her tits together with her arms.

I continued staring at them while I stroked myself.

“I suppose,” she began slowly, “it would only be fair if you got a chance to suck on them too.”

“I have to agree with you on that one,” I nodded. Madison giggled and lowered herself so that her tits were hanging in front of my mouth. I grabbed the left one and held it steady as I flicked her nipple with my tongue. She moaned softly as I took it into my mouth, sucking on her nipple.

“Fuck, that feels good,” she said softly.

I was stroking myself wildly at this point. I wanted to come while I had her tits in my mouth. I switched to her other nipple, sucking it gently. She braced herself against my thigh. I could feel myself about to come, and I think she could sense my urgency because she didn’t stop me. I kept sucking her nipple as I began to come. The ropes erupted out of my cock, most of them landing on my stomach or her arm. I ran my tongue all around her nipple as I climaxed.

I popped her tit out of my mouth once my orgasm subsided. Madison ran to the bathroom and came back with enough tissues to clean us both up. She still had her tits out.

“Thanks for that,” I breathed. “Your tits are fucking great.”

“I’m glad you enjoyed them,” she smiled. “Anyways, I’ll definitely let you know how it goes whenever I try to play with my booty.”

“Please do,” I grinned. I put my dick away and she put her tits away.

We sat and talked for a while longer before she said she was getting tired and wanted to go to bed. I was still horny from earlier and Ashley wasn’t due back for another hour and a half so I figured I may as well jack off again.

“Hey, I have a quick favor to ask.” I said.

“What’s up?”

“Sooo I’m still horny,” I began. Madison laughed. “But Ashley isn’t going to be back for a while.”

“So you’re gonna jack off again?”

“Yeah, and I was wondering if I could see your tits on more time, you know, so I had some fresh material.”

Madison giggled. “That’s actually kind of sweet in a weird, sexual way. But you just sucked on my nipples. Is that not fresh enough in your head?”

“Well, I’m glad you think so,” I chuckled. “And look, I was just trying to come up with an excuse to see your tits again.”

Madison laughed. “That was all you could come up with?”

“I’m horny,” I complained. “That’s the best I could manage.”

“Tell you what. I’ll do you one better, even though you clearly don’t deserve it,” she teased. She took her tits back out and immediately I got completely hard. “The idea of you jerking off to me is really hot so you can take a photo of me. Either delete it after you come, or just don’t show anyone obviously.”

My mouth hung open for a second. “Holy shit, okay,” I stammered. “Thanks Madison.”

“Don’t mention it,” she said, giving me a smile. “What pose do you want me to do?”

“I get to pick a pose?” I asked excitedly.

“I don’t see why not,” Madison shrugged. “The entire point of this is to get you off so why not let you pick?”

My cock was throbbing at this point. Madison was doing this explicitly to get me off. Incredible.

I thought for a second. “Okay, this is gonna sound really cheesy but bear with me. Can you get down on your knees and stick your tongue out like I’m giving you a facial?”

Madison giggled. “Sure. That’s pretty hot, honestly.” She dropped to her knees and held her tits together. I got my phone out and held it up. She stuck her tongue out and smiled with her mouth wide open. I backed up so I had all of her in-frame and snapped the photograph.

“This is awesome,” I grinned.

“You could take another if you wanted,” Madison said. “Maybe one of my butt?”

“Yes please,” I nodded.

Madison eyed the bulge in my pants. “You may as well take that thing out. It looks like it’s far too hard to be all trapped and uncomfortable.”

I almost just took it out but I decided to play with her a bit. “You just wanna see my dick,” I teased.

“Nuh-uh, I’m just trying to be considerate,” Madison laughed.

I smirked at her. “Y’know, it really isn't too bad where it is. Maybe I’ll just leave it there.”

Madison blushed and then pouted. “Okaaaay,” she said, drawing the word out. “I just want to see your dick. Happy?”

“Almost,” I grinned. “Why do you want to see it?”

“You’re the worst,” she blushed. She was still laughing though. “I wanna see it --”

“-- see what?” I interrupted.

“Your cock,” she said, “because it’s big and hard and sexy.”

“Those are good reasons,” I nodded, satisfied with her answer. I pulled my pants down and my hard cock sprang free. In her defense, this was infinitely more comfortable.

Madison starred at it hungrily. I saw her eyes shift down and briefly gaze at my balls before returning to my cock itself. She looked for a moment longer before looking back up at me, blushing hard. “What?” she said. “You have a nice dick.”

I smiled and shrugged. “Nothing, it’s just amusing to see you so entranced by it. I noticed you checkin’ out my balls too.”

“I can’t help it,” she shrugged, dropping her sweatpants to her ankles and stepping out of them. She was wearing a black thong underneath. “Or at least I like looking at it so.”

“I can see that,” I laughed.

“And yeah, your balls look lovely as well,” she smiled.

“Thank you,” I grinned.

“So how should I position myself for you?”

“I figured you’d just turn your back towards me and that would be all. What are you willing to do?”

“Oh please,” Madison laughed. “That would be boring. I’m trying to help you get off here.”

My cock throbbed when she said that last part. “Well, there’s the obvious position…”

Madison turned away from me and stepped away from the couch. She slowly got down onto her hands and knees before arching her back, sticking her butt up in the air. “Would you prefer me on my hands or elbows?” she asked, briefly alternating between the two. Both looked amazing, but her ass looked the best when she was on her elbows. She looked back at me.

“Elbows makes your butt look the best,” I said. “And I love how you knew what position I was talking about.”

She grinned at me and nodded before dropping down from her hands to her elbows, slowly rocking her hips back and forth.

“I haven’t been in the position for a guy in forever,” she mused out loud. “It was always one of my favorites.”

“Mine too,” I smirked. I got behind her and took another couple of photos. I zoomed in on her ass some. I also took some from a little to the side so I could see the rest of her body. Finally, I took a photo entirely from the side so I could see her tits hanging down.

“Okay, we’re good,” I said.

Madison got up, not bothering to get dressed. She stood in front of me wearing nothing but her thong. “Well, you’ve gotten me all worked up again,” she said, pouting.

“Hey, this was your idea,” I smiled.

“Fair point,” Madison said, returning my smile. Her nipples were quite hard. She looked down at my dick. “You’ve sprung a leak,” she joked, observing the large amount of precum oozing out of the head of my cock.

She stepped towards me and reached her finger out, tracing it briefly up the underside of my cock head to the slit. My cock sprang upward and I half-moaned, half-gasped. She got a big dollop of my precum on her finger and sucked it off.

“Jesus Christ, Madison!” I said.

“What?” Madison giggled. “I wanted a taste and Ashley isn’t here to get it for me. Plus you moaned so I know that felt nice.”

“It did.”

She stared at my cock again. She had a hungry look in her eyes.

“You want my cum, huh?”

She nodded.

“Get on your knees, Madison.” I said. I didn’t speak in a commanding voice like I would to Ashley, but there was a firmness to my voice.

She got down on her knees in front of me and began touching herself. I followed suit, grabbing ahold of my shaft. I used my precum as lube and began to pump my cock up and down. Immediately it felt incredible, and I could tell I wasn’t going to last very long.

“Where do you want it?” I groaned.

“My face. Make sure you shoot some of it into my mouth,” she groaned as she rubbed her clit.

I was standing right in front of her at this point. The sounds of our moans filled the room, along with the sound of my hand moving up and down my cock. Madison reached up and held onto my thigh, stroking it gently. Her hand slowly moved towards the inside of my thigh, and she continued to stroke the area gently. Then, her fingers grazed the side of my balls ever-so-slightly. She looked me in the eye and I knew that through her gaze she was asking for permission. I nodded. She smiled, bit her lip, and very gently caressed my balls with her hand. My legs began to tremble. Madison gently massaged my balls with her fingers, stroking the skin delicately.

I only lasted another couple of seconds; the feeling of Madison playing with my balls was too much for me to handle. I stroked myself wildly as I began to climax. Madison continued to massage my balls gently as I painted her face with my cum. I shot three or four ropes into her open mouth, which she held, not swallowing, savoring the taste.

Once my orgasm subsided, I was able to get a good look at her face. Good God did I come a lot. Her face was absolutely plastered with my semen. Madison herself was shaking, still holding onto my balls, massaging them in her hand. Almost immediately her own orgasm tore through her body. She cried out -- a little too loudly -- as her body shook and trembled. She held onto my balls throughout her entire climax. Once she finished, she collapsed backwards. I ran to the bathroom and grabbed a bunch of tissues before hurrying back and wiping her face clean while she laid there, breathing heavily.

“Wow,” she said after a moment.

“Did you feel good?” I asked her, smiling.

“Yes Brian,” she said. “That was incredible.”

“Mine was too.”

“I’m glad,” she smiled, still breathing hard. “You came a ton. I guess you really like having your balls played with, huh?”

“Duh.” I laughed. “And it seems you like playing with balls.”

“Duh,” she said, mimicking my tone. She grinned. “Let’s do this again sometime?”

“Yes please,” I said.

“I’m actually going to go to bed now,” she laughed. “Make sure you put those pictures to use sometime soon.”

“Oh, I honestly wouldn’t be surprised if I jacked off again today,” I said.

“Neither would I.” She got up slowly. “I think I’m gonna try putting a finger in my butt tomorrow morning. I know I’m going to wake up super horny after what we just did.”

“Sounds good to me,” I said. “Let me know how it goes, okay?”

“Of course,” she said. “After all, I gotta get my booty to the point where it could take something like that.” She gestured towards my cock.

“Yes, you do.” I agreed.

She walked over to me and hugged me. I’m almost ashamed to admit it, but feeling her naked tits against my chest made me hard again. It didn’t help that I could feel her wet panties against my leg either.

“Good God, does that thing ever quit?” She said, giving my dick a quick tap on the head with her finger. She gave my balls a very quick squeeze before breaking our embrace.

“Not when there’s a hot, naked girl in front of me.”

Madison blushed. “Well, I’m not naked. But fair enough.”

I stared unabashedly at her tits for one last moment before looking back up at her face. “Goodnight, Madison.” I sat down and and opened my phone, pulling up the photos I took of her. I began to stroke myself, figuring I could come one more time and then have enough time to recover so I could fuck Ashley when she got back.

Madison laughed, “Goodnight, Brian. Have fun!”

“Oh, I will,” I grinned. I watched Madison’s ass as she walked away.

If I remember correctly, I came to the photo of Madison on her elbows and knees. If only she wasn’t wearing any panties in that photo. I cleaned myself up and laid on the bed in Ashley’s room until she got home. Once she was home, she came in and said “hello” before hopping in the shower. She came back into her room with her hair in a towel and nothing else on.

“Hey, just so you’re aware, Madison and I masturbated together a couple of times today,” I said.

“That’s fine,” Ashley said, sitting down next to me. “Honestly, you don’t need to tell me every time you guys masturbate.”

“Okay,” I said. “We also did a little more than that, though.”

“Oh?”

“The second time we masturabted, she reached up and massaged my balls while I finished on her face.”

Ashley laughed. “Good God. You both must’ve loved that.”

“Are you upset?”

“No!” Ashley said. “I don’t care. Do whatever you want with Madison. Alyssa too. I don’t care if you play with them since you’ve already given me permission to do the same. Nobody else though, obviously.”

“Sweet,” I grinned. “Madison did say she was going to try playing with her butt tomorrow.”

“Oh yeah? Are you involved with that at all or…?”

“Well, not exactly. But she did say that she wanted to get her ass to the point where it could handle something like my dick.”

“Wow, she said that?”

“Essentially, yeah.”

Ashley looked amused. “She’s getting bolder.”

“No kidding.”

“And no, I wouldn’t care if you fucked her in the ass,” Ashley said, answering my next question before I even asked it. “Like I said, you can play with her as much as you want.”

I laughed. “Yeah, that was going to be my next question.”

“Obviously,” Ashley giggled. “Man, I bet you can’t wait for her to be ready for your cock.” She pushed me back and crawled on top of me. She reached back and took ahold of my dick, which was completely hard by this point, and aligned the head with her pussy. She sank down onto me, slowly taking me inside of her. We both moaned loudly.

“Well, you seem excited by the idea yourself,” I groaned as she began to ride me.

“The idea of my sister being fucked in the ass by my boyfriend? Yeah, that’s hot,” Ashley moaned.

“Would you want to watch?” I asked. Ashley braced herself on my chest and began to really bounce her ass up and down on my cock. I could tell she was already close to her first orgasm.

“Obviously,” she groaned. I reached up and grabbed her tits as she bounced on my cock. I ran my thumbs over her nipples, eliciting another moan out of her. “Ideally I’d like to participate.”

“Maybe she could eat your pussy while I fucked her ass,” I grunted. Ashley’s cunt was really milking my cock.

“I’d like that,” Ashley cooed as I bottomed out inside her pussy.

“And maybe you should help her,” I said. “I think she’s nervous about putting even a finger in her asshole.”

“Yeah, I’ll offer to help her,” Ashley moaned. I began fucking her harder, thrusting into her as she rode me. “I don’t know if she’d let me touch her asshole or anything, though.”

“Maybe not,” I said, “but it’s worth a shot.”

“Oh fuck,” Ashley cried out, “I’m coming, don’t stop fucking me Brian, oh my GOD!”

I felt Ashley’s pussy throbbing hard around my cock as she climaxed. She was already incredibly wet before coming, but now her pussy was soaked. It took everything I had not to come inside her.

Once she finished coming, she shifted forward, allowing my cock to slide out of her pussy. I immediately knew where this was going. Ashley smiled at me as she reached back and positioned my cock against her asshole. She sat back down onto me and her ass readily swallowed my cock.

“Oh fuck,” I grunted.

Ashley had a look of pure bliss on her face as she sank all the way down onto my cock. We both sighed as I bottomed out in her ass.

“Just let yourself come,” Ashley said, biting her lip. She braced herself against my chest and began to bounce her ass up and down.

I moaned loudly, “Holy fuck!”

I reached forward and held Ashley’s hips as she bounced her asscheeks on my cock. She moaned loudly, savoring the feeling of her ass being fucked.

“I’m gonna come, baby,” I groaned. “Fuck me, oh my God!”

“Fill my ass with your cum, daddy,” she cried, riding me fast and hard.

My cock exploded inside her, painting the inside of her rectum with my jizz. I gripped the bed sheets as her ass milked my cock, extracting every last drop of semen from my balls. Ashley groaned loudly.

I sighed as my orgasm finished. Ashley slowly rose up off of me. She quickly ran to the bathroom to clean herself up, returning with some tissues with which she cleaned my cock. We cuddled there for a moment before getting up to brush our teeth and go to sleep.

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