Author’s Note:
Hello all! I apologize for yet another extremely long lapse between the release of the previous story and this one. I’ve been extremely busy. I genuinely appreciate the continued support and interest in my stories, though. I hope you all are doing well, and I very much hope you enjoy this next chapter.
There are two characters in this chapter, Kristen and Jordan, who are relatively new. Both of them made an appearance in the last chapter, and they are also found in another story/series, “Brian & Ashley”. That series is also about Brian and Ashley (the main characters from this story), but it focuses on their interactions with other characters (namely Kristen and Jordan, at least initially) rather than Madison (Ashley’s younger sister) and Alyssa (Madison’s girlfriend). So if you want some more back story on Kristen and Jordan, be sure to check out that series/story.
As always, thanks for reading. 🙂
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Ashley, Jordan, Kristen, and I were hanging out in Ashley’s room. It was a Friday, which meant that Ashley and Kristen would be going to work shortly. For those who are unaware, Ashley is my girlfriend, and Kristen and Jordan are dating. I consider Jordan to be one of my best friends.
I was sitting on Ashley’s bed. Ashley was next to me. Jordan was sitting in Ashley’s desk chair, and Kristen was sitting on the edge of the bed. Normally we would all hang out again after Kristen and Ashley were done with work, but Ashley and I were going to hang out with Madison (Ashley’s sister) and Alyssa (Madison’s girlfriend).
“So same time next weekend?” Jordan asked.
“That works for us,” I said. Kristen nodded in agreement.
“Cool,” Ashley said. She got up and walked over to her closet. She opened it and grabbed a button-up shirt for work before fetching a pair of work pants from her dresser. Kristen grabbed her work clothes out of her backpack, which she had brought with her.
“I think I’ll hang out here for a bit babe,” Jordan said.
“Okay,” Kristen said. She pulled her shirt up over her head and set it down on the bed. She was wearing a maroon bra underneath. Jordan and I made no effort to avoid staring at her cleavage. Kristen noticed our gazes and flashed us a smile before putting on her work shirt.
The same thing happened with Ashley, who had just taken her top off as well. Jordan and I enjoyed the view of my girlfriend’s tits (covered by her bra, of course) as she changed into her work clothes. We had the added treat of seeing Ashley’s nipple piercings through her bra.
I think the girls enjoyed our audience, as they made a little show out of changing their pants. Kristen turned away from us and bent over, arching her back slightly. She slowly pulled down her pants, revealing a thong that left little to the imagination. I felt my cock getting hard.
Ashley quickly did the same thing — she turned her back towards us and bent over, slowly taking off her pants. My girlfriend was wearing a cute little red thong.
Kristen grabbed her backpack and began to rummage around through it as an excuse to stay bent over. Her thong basically covered the entirety of her pussy, but luckily for us, the fabric thinned out considerably around her asshole. Specifically, Jordan and I could clearly see the darkened skin surrounding her hole. We could even make out a few of the creases of her asshole behind the thin strip of fabric.
As Kristen continued to rummage around her backpack, Ashley slowly swayed her hips back and forth, feigning no excuse for this display other than to turn us on. And Ashley’s thong left even less to the imagination than Kristen’s. The thin strip of fabric covering Ashley’s pussy clearly showed both of her pussy lips on either side. Ashley’s asshole was almost completely visible too; the thong really just covered the hole itself. The creases and darker skin around Ashley’s asshole were completely obstructed. The fact that my girlfriend was showing herself off to my best friend like that was admittedly extremely hot (and his girlfriend was doing the same for me, of course!).
The girls kept themselves on display for another few seconds before giggling and standing up. Ashley gave Kristen’s butt a firm smack before putting her pants on. Kristen laughed and returned the favor, slapping Ashley’s butt with her hand.
“Y’all are too much,” I said with a grin.
“Are we?” Kristen giggled. She walked over to Ashley’s desk, where Jordan was still sitting, and reached down to feel her boyfriend’s crotch.
“What’s the verdict?” Ashley asked, smirking slightly.
“Hard as a rock,” Kristen giggled. “Feel free to check for yourself, though.”
Kristen turned to me and gave me a smile before walking over. She placed a hand on my thigh and slowly slid up my leg. Kristen bit her lip as her fingers first brushed against my cock. She gently wrapped her hand around my shaft — through my athletic shorts — and squeezed it.
“What do you think?” Ashley asked. She had walked over to Jordan and was standing in front of him now.
“He’s plenty hard, alright,” Kristen giggled. She hadn’t let go of me yet. Instead, her hand was slowly sliding up and down my erection. It felt nice.
“No surprise there,” Ashley laughed.
Kristen continued to slowly jerk me off through my pants. The two of us watched as Ashley lifted the waistband of Jordan’s shorts and boxers before sliding her hand into his pants to grip his cock directly. She first reached down and gave his balls a quick squeeze before wrapping her hand around my friend’s shaft.
“What do you think, Ashley?” Kristen asked, biting her lip again. I could tell it turned her on to watch Ashley grope her boyfriend’s dick.
“Rock hard, just as you said,” Ashley grinned. She began slowly pumping Jordan’s cock, enjoying how it felt in her hand. As precum began to leak from the tip, Ashley used her thumb to spread it around his cock, providing some better lubrication for her to jerk him off.
Kristen went ahead and slid her hand underneath the waistband of my gym shorts and boxer briefs. I moaned softly as I felt her fingers directly on my cock. She began to jerk me off again. We stayed like this for another minute or so — Ashley stroking Jordan’s cock as Kristen stroked mine. Jordan and I moaned softly as we enjoyed the feeling of one another’s girlfriends stroking us off.
Ashley sighed. “Damn. If only we had a little more time before work. He’s so nice and hard…”
“I know,” Kristen pouted. “If not for work, I’d happily take care of this for you, Brian.” She gave my cock a final squeeze before winking at me and turning back around.
Ashley sighed again and let go of Jordan’s cock. She came over and gave me a kiss before walking into the hallway. Kristen did the same, walking over to give Jordan a kiss before following Ashley into the hall. Jordan and I got up, unashamed at the tents we were both rocking. He grinned at me before following the girls into the hallway.
Ashley waited for me outside her door. She gave me another kiss before saying to Kristen, “ready?”
“Mhm,” Kristen said cheerfully. The two girls walked upstairs while Jordan and I went over to the lounge area of the basement. The plan was to just drink and play videogames for a bit. I was a little concerned about getting blue-balled, but I don’t think I got quite enough action to have anything to worry about. If we had messed around any longer then I likely would’ve needed to relieve myself, though.
I went and grabbed some beer from the fridge. Jordan retrieved a bottle of whiskey from his backpack. We sat on the couch and booted up Smash (i.e., Super Smash Bros). He and I cracked open a couple of beers and started playing. I think I was on my second drink by the time my phone buzzed. I looked at it — a text from Madison.
The text read, “Is that the guy we sent stuff to the other day?”
I quickly typed out a response and sent it, “Yep, that’s him. His girlfriend was here earlier, but she and Ashley both went to work.”
Jordan and I played a little longer. We had both killed three or four beers a piece by this point, or at least I knew I had drank three so far. I wasn’t really keeping track of Jordan’s intake, but we were both starting to get a good buzz going.
I looked at my phone again and saw that Madison had texted me a few minutes prior. “And they have an open relationship or whatever?”
“Yeah, I wouldn’t have sent them stuff otherwise.” I replied. I could’ve supported this further by telling Madison about how Kristen had stroked my cock a bit earlier (and that Ashley had jerked off Jordan for a bit), but I felt that to be unnecessary. Instead, I sent another text saying, “We’re just drinking and playing Smash if you wanna come hang.”
“Are you guys drunk?” she sent back almost immediately.
“A little,” I replied. We weren’t really drunk, but we were getting to that point pretty quickly.
Jordan and I kept playing for a few more minutes. We were just finishing a match when Madison came out from around the corner. She was wearing booty shorts (i.e., daisy dukes, very short-cut jean shorts, etc.) and a tank top that didn’t leave much to the imagination. She was blushing a bit, though I could tell she was trying to come off as confident.
“Hey Madison,” I grinned. Jordan looked very surprised to see her.
“Is that…?” he whispered to me. I nodded subtly. Jordan grinned.
“Hey Brian,” Madison smiled. She looked at Jordan. “Jordan, right?”
“That’s me,” Jordan said.
“You want a beer?” I asked Madison, gesturing to the unopened cans we had sitting out.
“Yes, please,” she said quickly. I chuckled. Liquid courage. I really don’t know why Madison was so nervous; Jordan was just about the most easy-going guy I knew. But I guess Madison didn’t know him well at this point.
“We could also take a shot together?” I offered. “I mean, you can still have the beer either way. But we have liquor if y’all wanna take a shot.”
Jordan shrugged. “I’m down.”
Madison nodded.
I grabbed Jordan’s bottle of whiskey and poured what I estimated to be one shot’s worth of alcohol into each of three red solo cups. I handed Jordan and Madison a cup and then retrieved mine.
“Well?” I said, raising my cup.
The others raised their cups and then took their shots. Madison made a face. Jordan and I handled ours fine. We were already drunk enough that the taste didn’t bother us.
“Wash it down with some beer,” Jordan chuckled as Madison shook her head back and forth.
“Blegh,” she said. She cracked her beer can open and took a swig.
“So Madison, have you ever played Smash before?” Jordan asked.
“Not really,” Madison said. “I’ve overheard Brian talking about it before, though.”
Madison watched Jordan and I play for a bit, sipping on her beer. Once our match ended, Madison asked if we’d like to do another shot.
“I’m down,” Jordan said.
“Same,” I said. I poured another round of shots in the same cups from before. We tapped our cups together and took our shots. This one definitely went down easier for everyone.
“Woo, alright,” Madison said, shaking her head. “I think I’m good for now.”
“Same,” Jordan chuckled. “At least, I don’t need another shot for a little bit.”
“Agreed,” I chuckled.
“So Madison, I gotta say,” Jordan started. “I really enjoyed the show from you and Brian the other day.”
“I was wondering how long it’d take before you brought that up,” I laughed.
Madison giggled and blushed. “Well, I’m glad you enjoyed it.”
“I’m surprised you’re so good at giving head — like blowjobs — even though you’re dating a girl,” Jordan grinned. The man certainly had a way with words.
“What can I say?” Madison shrugged. “I take pride in my skills. And besides, I don’t only date girls.”
“Apparently not,” Jordan smirked.
“She’s quite talented,” I said. “Madison definitely knows what she’s doing.”
Madison shrugged. “I’ve had a lot of practice lately.” She gave me a wink.
“Goddamn, Brian,” Jordan said. “You are one lucky dude.”
I laughed. “That I am.”
“Y’know,” Madison said. “It might be… helpful if I had more than one guy to practice on.”
“Oh?” Jordan said.
I laughed again. “I think the alcohol is getting to you, Madison.”
“Maybe,” she grinned. “But I’m just saying! I don’t want my skills to be too… specified.”
“Specified?” I asked.
“I think she means that if she only sucks your dick, then she’ll just be good at sucking your dick and not, like, any other dick,” Jordan said.
“Yeah, that’s what I meant,” Madison laughed.
“Well,” I said. “We just so happen to have another guy here who likes blowjobs.”
Jordan laughed. “I’m game,” he said.
“Yeah,” I said. “You could practice on us for a bit if you want. Show off your skills. After all, it’s not every day you have two dicks available to play with, in your own basement no less!”
Madison nodded. She took another big swig from her beer and put her hair back in a ponytail.
“Oh shit,” Jordan said, shooting me a look. I returned his look with a shrug and a grin.
Madison got down on her knees in front of us. “Who’s first?”
“Jordan,” I said. “Show him what you got.”
Madison nodded. She shifted over so that she was kneeling directly in front of Jordan, who spread his legs, allowing Madison to move forward so that she was in between them.
Jordan lifted his butt up off the couch enough to get his pants down to his knees. He shifted around to pull his boxer briefs down next, revealing his semi-hard cock. His balls had been shaved fairly recently and were pretty smooth. Good timing.
Madison grinned. She’d obviously only been playing with my cock lately; it had been quite a while since she’d had another to play around with.
“Why don’t you take your shirt off?” I suggested.
Madison blushed and nodded. She reached down and pulled her shirt up and over her head, revealing to us that she wasn’t wearing a bra! Her gorgeous tits came into view, with her pretty, pink nipples standing at attention, clearly erect.
“Holy fuck,” Jordan gasped. He definitely wasn’t expected to see her tits.
She smiled at him sweetly. Madison leaned forward and placed her hands on Jordan’s thighs. Slowly, she traced her hands up towards his growing erection.
Jordan breathed in sharply as Madison’s fingers wrapped around his shaft. She held Jordan’s cock in her hands for a second, enjoying the feeling of it growing to its full size. With her other hand, she gently cupped Jordan’s balls and massaged them.
Madison leaned forward more and brought her head down. She opened her lips and took one of Jordan’s balls into her mouth as she began to slowly stroke his shaft. He looked over at me and gave me a look that, to me, said holy FUCK Brian, I can’t believe this is happening.
Madison took the entirety of Jordan’s balls into her mouth and sucked them, causing Jordan to groan audibly. She released his sack from her mouth and, starting with his balls, began to trace her tongue up Jordan’s shaft. Jordan moaned as her tongue teased his frenulum for a second before running back down the length of his shaft and down his balls.
Madison traced her tongue back up Jordan’s shaft, this time stopping at the top to lick the head of his cock.
“Fuck yeah,” Jordan groaned. He watched Madison circle her tongue around the ridge of his cock, stopping to tease the sensitive underside of the head every so often.
With them pretty distracted, I grabbed my phone and quickly recorded a video on Snap chat to send to Ashley. In the video, you could clearly see Jordan’s cock and Madison’s mouth and tongue. I panned the camera up briefly to catch Jordan’s face so Ashley would know who her little sister was sucking off. I sent the video and returned my focus back to them.
Madison had started gently sucking the head of Jordan’s cock, occasionally bobbing her head down to take more of him into her mouth. She was working the base of his shaft with one hand, pumping it nice and slow, while the other hand massaged his balls.
I could tell Jordan was in heaven. And I was also enjoying this. Watching my girlfriend’s little sister suck another man’s cock (instead of my own) was incredibly fucking hot. The fact that this man happened to be one of my best friends made it even better!
Madison worked my best friend’s cock for another thirty seconds or so before coming up off of it.
“I think I ought to give Brian a turn,” she said, still stroking Jordan’s cock, which was slick with her saliva.
“Not gonna turn that down,” I grinned. I lifted myself up off the couch enough to get my shorts and underwear down around my ankles. Madison shifted over so that she was kneeling on the ground in front of me.
Madison looked up at me with a devilish smile. She scooted forward and, wasting no time, immediately began to trace her tongue up and down my cock. I was, of course, already rock-hard. I groaned loudly as my girlfriend’s little sister began to pleasure me in front of my best friend. I wondered, for a brief second, how our girlfriends would think about this. No doubt they would both find it hot as Hell.
Madison traced her tongue up the length of my shaft and popped the head into her mouth, sucking me gently. I ran my hand through her hair and gripped it at the roots, holding it firmly. She whimpered softly as I pressed her head down, forcing more of my cock into her mouth. I forced her to bob up and down on my shaft, pressing her head back down until she had almost all of me in her throat before letting her come up a bit, only to press her back down again. The wet, slurping sounds of her lips sliding up and down my cock filled the room.
“Fuck man,” Jordan said. “Look at her go. How’s it feel?”
“She’s a fuckin’ pro,” I half-said, half-moaned. “It feels fucking great. She knows how to suck a cock.”
I pulled her up off my cock, still gripping her hair firmly in the back.
“Go make him come,” I said, looking her in the eye.
I released her head and she nodded. “Yes, daddy.”
“Oh my God,” Jordan said. I don’t think she expected Madison to call me “daddy”. To be honest, I didn’t really either, but I fuckin’ loved it, especially because Jordan was here.
Madison scooted back between Jordan’s legs and took his cock back into her mouth. He was just as hard as when she stopped sucking his dick. She immediately began bobbing her head up and down his shaft, taking almost all of him into her mouth each time. Jordan’s toes immediately curled and he moaned loudly. Madison was doing what I told her to do.
I looked down at my phone and saw that Ashley had responded to my snap chat. I opened it and it was a picture of her face, mouth wide open but clearly smiling. She had captioned it, “holy fuck! What a little slut! I was already horny after playing w Jordan’s cock, and now this?!”
I chuckled quietly to myself. I readied my camera and watched as Madison brought Jordan closer and closer to orgasm. She was working his cock expertly — all the practice she put in on mine was paying off.
“Fuck, Madison,” he grunted. “I’m gonna come!”
I started recording and watched as Jordan’s orgasm hit. He threw his head back and held Madison’s hair as she took his cock all the way into her throat. She rubbed his balls as they emptied themselves into her mouth, shooting rope after rope of fresh, warm cum. Once Jordan finished, Madison came up off his cock and showed him her open mouth, still full of his cum.
“Shit,” Jordan said, breathing hard. “That was one of the best blowjobs I’ve ever gotten. Holy fuck.”
Madison turned towards me and saw I was recording. She made an effort to show the camera the fresh load she had before swallowing it and showing the camera her now empty mouth. Cheesy? Maybe. But it was fuckin’ hot.
I made sure to save the video. I modified the recipients, changing them from just Ashley to include Jordan and Madison as well before sending the snap chat.
“Madison,” I said. “Come sit against the couch.”
She did as she was told, turning around to face away from the couch. She scooted back so that her back was flush against the couch. Basically, she was sitting on the ground with her back against the couch.
“Scoot over so that you’re in front of the middle cushion.”
Jordan looked a little confused, but I’m sure he figured I had something particular in mind. Madison scooted over to where I had specified. I stood up and stepped so that I was standing over her. I grabbed her head and pressed it back so that it was resting on the couch.
“Open your mouth.”
Jordan grinned. I could tell by the look in Madison’s eyes that she was incredibly turned on by my ordering her around, especially in front of someone else.
Madison opened her mouth and remained still.
“Good girl,” I said. I bent over the couch, bracing myself with one arm against the top of the back cushions. The angle wasn’t perfect, but it would work.
With my free hand, I grabbed my cock and aligned it with her mouth. I slowly thrusted forward and sank my cock into her mouth. She whimpered softly as I entered her. I slid about half my cock into her mouth before sliding it out until just the head was in her mouth. Her tongue teased it, licking circles around my head. I thrusted forward again, this time sliding my cock all the way into her mouth until my balls rested against her chin. Madison whimpered softly, clearly enjoying the feeling of having a cock in her throat.
She reached down and quickly unbuttoned her shorts before sliding a hand into her pants. She began playing with herself.
“Oh my God,” Jordan said. “She’s masturbating! She’s touching herself while you face-fuck her.”
“She’s such a slut,” I said as I began to slide my cock in and out of her mouth a bit faster. Each time, I would sink myself down to the hilt and enjoy the feeling of having my cock buried in her throat. Then I would slide myself out and let her suck the tip for a second. Madison was squirming around beneath me, clearly enjoying the work she was putting in on her clit.
“That’s right, baby girl,” I said softly. “Take daddy’s cock.”
I began to thrust my cock in and out of her mouth a bit faster now, no longer stopping to let her suck my cockhead. I could feel my orgasm approaching rapidly; face-fucking my girlfriend’s little sister — while she masturbated and my best friend watched — was too much for me to handle.
“Fuck,” I grunted. I pulled out and began to jerk off. I moaned as the first rope of cum shot out of my cock and landed across Madison’s chest. I fired off another two ropes onto her tits before aiming at her face and unloading the remainder of my cum there. When my orgasm finished, she had a good amount of fresh semen on her cheeks and lips.
“Holy fuck,” Jordan said. “Jesus, you completely covered her.” He laughed a bit.
I grinned as I stood in front of her, catching my breath and admiring my work. That was a great fuckin’ orgasm. Madison had several ropes of cum criss-crossing across her tits. Her lips, cheeks, and chin were also covered with my jizz.
“Are you still horny?” I asked Jordan.
“Duh.”
“You wanna have a go?”
Jordan grinned. “Fuck yeah.”
He stood up and kicked his pants and underwear off his ankles. His cock was almost completely hard at this point. Madison stayed where she was, still clearly playing with herself. She seemed more than happy to let us use her mouth to our heart’s content. I stepped aside as Jordan got into the same position.
He leaned forward braced himself against the couch, positioning his cock at Madison’s mouth. Jordan thrusted forward and sank his cock into Madison’s mouth, sliding all of it inside until his balls were against her chin. He held it there for a second, looking Madison in the eye. She groaned softly and I could see her fingers furiously rubbing her clit. As her eyes began to water, Jordan slid his cock back out of her mouth.
“My God,” he groaned. Jordan began to fuck her mouth. He thrust his cock in and out of her mouth fast and hard, really fucking her good. “This feels fucking amazing. Holy shit.”
“Goddamn,” I said. “You’re really throat-fucking her.”
“Fuck yeah I am,” Jordan grunted. Surprisingly, he didn’t have much more left in him. I watched him face-fuck my girlfriend’s little sister for another thirty seconds, his balls coming to rest against Madison’s chin with each thrust, before he pulled out and frantically stroked himself off onto her face and tits.
Madison was breathing hard as a fresh load was shot onto her body. I could tell she was getting closer and closer to her own orgasm with each rope of cum that landed on her. Jordan sighed as his second orgasm of the evening finished.
He and I stood in front of Madison and watched as she masturbated, covered in our semen. There was cum dripping down off her nose and her nipples. She had streaks of semen across her eyes and her collar bones. My girlfriend’s little sister was absolutely covered in our cum.
Together we watched as Madison brought herself to orgasm, sitting on the ground in front of two guys who just throat-fucked her. She threw her head back (just as it was when we were using her mouth) and arched her back. Her toes curled and a cry escaped her mouth as her orgasm hit like a truck. She bucked her hips like mad as she played with herself, her fingers a blur on her clit. We watched as she moaned and shook, covered in our cum, her hips rocking back and forth as she enjoyed her orgasm. She must’ve climaxed for a good ten or fifteen seconds.
Once she was finished, she sat there, unmoving, breathing hard. Jordan and I were both rock-hard again. She looked up at us and smiled.
“Honestly,” she said. “Seeing both of you standing there with your cocks rock hard like that… I don’t think I’d ever get tired of the sight.”
“Likewise,” I laughed. “This is a pretty killer view.”
Madison blushed. “Can you help me up? I wanna wash off.” So much for the view! But I’d wanna wash off too if I were her.
“Wait! Lemme send a photo to Ashley.” I grabbed my phone and quickly snapped a pic of Madison sitting down on the ground absolutely covered in our cum. I saved the photo before sending it to Ashley, Jordan, and Madison.
“Okay, you’re good,” I said.
I held out my hand to Madison and held her up. She walked to the bathroom; Jordan and I followed.
The three of us walked into the bathroom. I let the other two walk in first so I could make sure to shut and lock the door behind me, not that I necessarily expected anyone to walk in right now. Madison drunkenly walked over to the shower and turned it on. She pulled off her shorts, which she hadn’t bothered to rebutton, and climbed into the shower, stumbling a bit but not falling over. Jordan chuckled as he watched her. Madison blushed. I guess she wasn’t too drunk to be unaware of her clumsiness.
I don’t really know how to describe how I felt watching her. I mean, she was naked and, like Ashley, she had a really nice body (obviously, I’ve described it a million times to you), so that was nice. But it was just sort of funny watching her hose off my and Jordan’s come from her face and chest. Like this whole situation was still bizarre given she was my girlfriend’s little sister.
Nobody really talked. Jordan and I just watched Madison rinse the jizz from her body and admired the sight of her tits and her ass. Once she had cleaned herself to her own satisfaction, she turned off the water. I went and grabbed a towel from the towel rack and handed it to her. She wrapped herself in it and stepped out of the shower onto the bath mat. She looked at herself in the mirror as she rubbed the towel against her skin.
“Okay, so I know I just had an orgasm,” Madison said. “Buuuut I’m still really horny.”
Jordan and I grinned. We were both already hard again. I mean, we had just been watching her shower — naked of course.
“Me too,” I shrugged. “Jordan?”
“It’s hard not to be hard when you’ve got a hot girl standing in front of you, completely naked,” he laughed.
Madison blushed. She dropped to her knees and, since I was the one closest to her, she reached over to me and pulled me closer to her by my leg. I took two steps so that I stood in front of her. She immediately took my cock into her mouth and began sucking me off again.
“Holy fuck,” Jordan said. “Madison, you look so fucking hot sucking his cock like that.”
Jordan’s hand found his cock and he began jerking off. Immediately Madison motioned for him to come closer. He let go of his dick and walked over. Madison reached over and massaged his balls for a second before taking Jordan’s cock in her hand. She began stroking him off, clearly in love with the act of working two dicks at once.
Madison’s free hand snaked down between her thighs and she began playing with herself while she blew me and jerked Jordan off. Man, the sight of my girlfriend’s little sister sucking me off would never get old. I watched as her lips slid down my cock, stopping to hold all of me in her throat before sliding back up so that her tongue could tease the head. I moaned softly. Jordan was right — Madison was really good at giving blowjobs.
I reached down and gripped Madison’s hair, holding it tightly right at the base. She immediately stopped moving her lips up and down my cock and instead held her mouth open; she knew what I was doing. I began to slowly thrust my cock in and out of her mouth, savoring the feeling of her lips tightly wrapped around my shaft. I groaned softly.
“Let’s go to Ashley’s room,” I said, removing my cock from Madison’s mouth. She nodded in agreement.
I turned and opened the bathroom door slowly, peering cautiously into the hallway. The coast was clear. We darted across the hall into Ashley’s room. Jordan was the last to enter; he closed and locked the door behind us. Jordan and I removed our remaining clothes; Madison was already naked. She hopped up on the bed and positioned herself on her hands and knees, arching her back so that her ass was up in the air. Jordan and I got a perfect view of her dripping-wet pussy and her tight little asshole. If only we could take turns pumping that gorgeous, pink pussy of hers full of cum…
“Jesus Christ,” Jordan breathed. I don’t think he ever expected to see Ashley’s little sister in a position like this. Certainly not when she was drunk, horny, and completely naked.
I hopped up on the bed and knelt in front of Madison, who immediately took my cock into her mouth and resumed my blowjob. Jordan climbed up onto the bed behind her. He grabbed her hips and admired the view. Madison’s gorgeous pink pussy and tight little asshole were on full display for him to enjoy. He gripped Madison’s cheeks, squeezing each with his hands before spanking her. He delivered a solid smack to the left cheek, eliciting a soft moan from Madison, before smacking her right cheek even harder. Madison whimpered softly. I know Jordan was just dying to sink his cock into Madison’s warm, wet pussy. How good it would feel to fuck her right now — just pound that tight pussy of hers until we were ready to unload inside her.
Jordan scooted back and knelt down, still holding onto Madison’s hips. Starting at her clit, Jordan slowly traced his tongue up Madison’s pussy.
“Oh fuck, holy shit,” Madison moaned, taking my cock out of her mouth. “Oh my, God.”
Jordan ran his tongue up and down her pussy again, eliciting another moan out of Madison. Jordan gave her ass another smack before running his tongue up to her vagina. He ran his tongue around the outside of her vagina before sliding his tongue inside her. Madison immediately cried out in pleasure.
She looked back up at me for a second before taking my cock back in her mouth. She did her best to blow me, but she was a bit distracted by Jordan’s tongue.
“Y’know, Jordan,” I said after a moment. “Madison is a bit of a slut for having her ass played with.”
Jordan gave me a look that communicated that he understood, or at least that’s how I interpreted the look. And he appeared to get it. Immediately, he moved up from her pussy and began eating Madison’s ass.
“Oh FUCK,” Madison cried out. She was breathing hard now — short, jagged breaths. Jordan ran his tongue around the outside of Madison’s asshole, moving it closer and closer to the center, teasing her.
“Oh my God,” Madison whimpered. “That feels so fucking good.”
Jordan continued to circle Madison’s asshole, allowing his tongue to run closer and closer to her hole itself.
“Please,” Madison whimpered.
Jordan pointed his tongue and licked Madison’s asshole directly for the first time. I watched her eyes roll into the back of her head as she moaned loudly. Jordan darted his tongue back and forth across her asshole now.
Being perhaps a little bold, Jordan pressed his tongue against her asshole, working it inside her a bit. Madison groaned loudly.
“Fuck yes, Jordan!” she cried out as she felt Jordan’s tongue slide inside her asshole. “Lick my ass. Oh my God, fuck yes!” I could see her toes curling back as Jordan wiggled his tongue around inside Madison’s ass.
“Jordan,” I said. “Look in the top-right drawer of our dresser there.”
Jordan got up and went over to the dresser while Madison stayed in position, whimpering, and clearly a bit sad that Jordan’s tongue was no longer in her ass.
Jordan opened the drawer. “Panties?”
“Yeah, rummage around in there. You should be able to find a couple of dildos.”
Madison immediately looked at me and grinned, her prior disappointment vanished.
Jordan looked around for a second. “Oh, I see them, they’re in the back,” he said.
Jordan pulled out two dildos — one a bit larger than the other. He brought them over to the bed and handed them to me.
I immediately handed the small one to Madison, who took it into her mouth and began to suck it enthusiastically.
“Holy shit,” Jordan grinned. “Aren’t these Ashley’s dildos?”
“Yep,” I nodded.
“Holy shit,” he said again, chuckling and shaking his head, likely in disbelief.
Once the first dildo was coated with Madison’s saliva, she handed it back to Jordan.
“Fuck her pussy with it,” I said.
Jordan grinned and lined up the toy with Madison’s vagina. Once the head was aligned with her pussy, Jordan slid the toy inside her.
“Fuck,” Madison breathed, her toes curling immediately. “Oh, shit.”
“Does that feel good?” I asked her.
She looked up at me and nodded. Jordan began sliding the toy in and out of her pussy now, using long, slow strokes at first. Madison moaned softly, enjoying the feeling of her sister’s dildo fucking her pussy.
I handed the larger dildo to Madison. She looked up at me as she took it into her mouth, sucking it in rhythm with Jordan’s fucking of her pussy with the first dildo.
Once again, I had to take a second to take in the sight before me. My girlfriend’s little sister was naked on her hands and knees on Ashley’s bed. She was sucking one of her sister’s dildos while one of my best friends fucked her pussy with another. And we weren’t done yet.
“Alright,” I said. “Try fucking her ass with the one you have there,” I gestured towards the dildo Jordan was fucking Madison with.
Jordan grinned. Madison bit her lip. Jordan pulled the toy out of Madison’s pussy. He aligned the head of the fake cock with Madison’s asshole.
“Ready?” he asked.
“Yeah,” Madison breathed. She bit her lip again as Jordan pressed the toy against her asshole. It only took a second for the head to slide inside her. Madison gasped.
“How we doin’?” Jordan asked.
“Good,” Madison moaned. “I can take more; Brian’s right. I love having my ass played with. I can handle this.”
Jordan grinned and shook his head. I think he was having a bit of a “holy shit” moment too. He slowly slid the rest of the dildo into Madison’s ass until it bottomed out inside her.
“Fuck, that feels so fucking good,” Madison moaned.
“It looks so hot,” Jordan said. “Do you want me to fuck you with it now?”
“Yes please,” Madison whimpered.
Jordan slowly slid the toy back out of Madison’s ass, stopping with just the head remaining inside her. Madison moaned as Jordan slid the dildo back inside her all the way. I watched as Jordan began to fuck Madison’s ass with long, smooth strokes.
“Holy FUCK,” Madison groaned. “That’s so good. Fuck yes, Jordan, that feels so good. Fuck my ass, holy fuck!”
I took the second, slightly larger dildo from Madison and handed it to Jordan.
“Fuck her pussy with that one,” I said.
Jordan took the toy from me and nodded. Without slowing down the fucking of her ass with the first toy, Jordan slid the other dildo inside Madison’s pussy.
“Oh my GOD,” Madison cried out. She stuffed her head into the bed and moaned loudly as Jordan began to fuck her pussy with the second dildo.
I walked on my knees around to the side of Madison partly so that I could get a better look at my girlfriend’s little sister being DP’d by Ashley’s sex toys. Madison’s pussy lips gripped the larger dildo so tightly, and watching her take that fake cock made my desire to fuck her even worse.
Madison reached back and began rubbing her clit as Jordan slid the toy’s in and out of her ass and pussy. He had a good rhythm going. As he slid the larger dildo into Madison’s pussy, he was pulling the smaller one out of her ass. Likewise, as he slid the smaller dildo back inside Madison’s ass, he slid the larger toy out of her pussy. And she was clearly loving every second of it. I knee-walked back in front of Madison and she immediately took my cock into her mouth. She sucked it gently. I think she just wanted to have all three holes filled.
Madison moaned loudly as she held my cock in her mouth. Her breathing was quickly becoming more rapid.
“Don’t stop,” I told Jordan. “I think she’s gonna come.”
Jordan maintained his rhythm, loving the sight of Madison’s pussy lips and asshole gripping the sex toys as they were thrust in and out of her body. I watched as Madison clutched the sheets hard with her free hand. She cried out as loudly as she probably could have given my cock was in her mouth.
“She’s coming,” I said. Jordan kept fucking her two holes with the toys as Madison’s entire body began to shake. She moaned loudly, still holding my cock in her mouth, apparently determined to orgasm with all three holes filled. Jordan and I just watched as she spasmed and convulsed in front of us. Jagged moans escaped her lips in between gaps for air. Jordan never let up on the toys; he continued to fuck her pussy and her asshole with them hard and fast through Madison’s orgasm.
When Madison’s climax finished, I hopped up and grabbed a towel from Ashley’s closet.
I handed it to Jordan. “For the toys,” I said. Jordan nodded. He slowly slid the larger dildo out of Madison’s pussy and placed it on the towel. Next, he slid the smaller toy out of her ass and placed that on the towel too. He wrapped them up slightly and placed the towel on the floor next to the bed.
Madison collapsed, basically panting. I rubbed her back. Jordan squeezed her ass.
“You ever have an orgasm with all three holes filled before?” I asked, grinning.
“Nope,” she breathed.
“How was it?” Jordan asked.
“Fucking amazing,” she said, breathing hard. “I’ve had plenty of orgasms with something in my butt or something in my pussy, but not both at the same time, and definitely not with a cock in my mouth too.” She took another second to catch her breath before saying, “but I think it’s y’all’s turn to cum again.”
“What do you have in mind?” I asked, a little hesitantly.
“Well,” Madison grinned. “My ass is all warmed up and ready. I think it’s about time I took a real cock up there.”
“Holy shit,” I said. Jordan’s jaw dropped a little. “Are you sure? We can just stick to blowjobs or something. We don’t care.”
“No, I want your cock inside my ass, Brian,” she said, looking me in the eye. Then she turned and looked at Jordan. “And yours too.”
I didn’t say anything for a second. I was trying to contemplate her proposal, but I was admittedly a little too drunk to think clearly. And the horniness was getting to me a bit too, obviously.
“My pussy is still off-limits,” Madison said. “But there’s no reason both of you can’t enjoy my ass.”
“Okay,” I said. “If you’re sure.”
“I am,” she said, biting her lip. “I want to feel you both shoot a load inside my asshole.”
“Holy shit,” I breathed. “Fuck yeah, let’s do it.”
Jordan looked at me and grinned. “You got it first, man,” he said, stepping aside.
Madison rolled over so that she was on her back. “Gimmie Ashley’s pillow,” she gestured at me.
I gave her the pillow. She lifted her butt up in the air and positioned the pillow underneath her so that her ass was elevated a bit.
“Oh, that’s a lot better,” I said. She was in a much better position to take my cock in her ass like this. I took a moment to appreciate the sight before me: my girlfriend’s little sister, completely naked, legs spread wide open. Her cute little nipples stood completely erect, and her pussy glistened with juices from her last orgasm. Below that was her tight little butthole, my target.
Jordan tossed me the bottle of lube. My cock was already soaked with Madison’s spit, but I squirted a healthy glob of lube onto my shaft and rubbed it in a bit, just to be safe. I wiped my hand off on one of the towels, and then shifted forward.
“Are you ready?” I asked her.
She nodded, pleading at me with her eyes to get my cock inside her already.
I shifted forward and aligned my cock with her ass so the head was pressed right up against her hole. Madison whimpered softly. I pressed forward some more, and her ass immediately gave a little, allowing the head of my cock to enter her.
“Oh my God,” I moaned as I watched my cockhead disappear inside Madison’s ass for the first time.
“Fuuuuck,” Madison moaned. “Oh my God, Brian. You’re finally inside me. Fuck.”
Madison reached down and began to play with her clit as I slid more of my erection inside her. Her asshole gave some resistance, but the work Jordan put in earlier helped warm Madison up, and I was halfway inside her without too much effort.
“How is this?” I asked her. “Are you okay?”
“Yes, this feels fucking amazing,” she purred. “We should’ve done this a long time ago. It feels so good to finally have your cock inside me.”
I held still for another moment, relishing the sight of my cock halfway buried in her ass. Jordan was shameless stroking his cock to the sight of me sodomizing my girlfriend’s little sister.
“I can take all of you, you know,” she said softly. “That was always the goal, wasn’t it?”
I chuckled and nodded. I grabbed onto the sides of her stomach and thrust the remainder of my cock inside her. The two of us moaned loudly as I bottomed out inside her. My balls were resting against her ass cheeks, and I enjoyed the feeling of her tight ring gripping the base of my cock. Madison’s fingers were already speeding up as she worked herself towards another orgasm.
“Fuck me, Brian,” she groaned. “Fuck my tight little ass.” Hearing Madison talk dirty like this was driving me crazy.
I slowly slid my cock about halfway out before thrusting forward so that I bottomed out inside her again.
“Fuck, that feels so good,” she moaned.
I began to thrust my cock in and out of her ass faster now, and with longer strokes. She was impossibly tight and so warm. I reached up and grabbed a handful of her breasts as I slid my cock in and out of her ass.
“Oh my God, Brian,” she cried out. “Your cock feels so good. Please don’t stop, fucking Christ, please don’t stop!”
I pinched her nipple with one hand while I gripped her side with the other. Her ass felt so fucking good. I leaned forward and moved my face towards hers as I began to really fuck her fast now. I brought my lips to hers and we kissed as we felt our orgasms approaching. She traced my lips with her tongue as I did hers, and our tongues intertwined in between gasps and moans. I broke our kiss to watch her face contort with pleasure as I pounded her ass. She cried out my name in between gasps and groans. She felt impossibly tight, and it wouldn’t be long before I was emptying my balls inside her.
“Are you close?” I whispered to her, knowing I didn’t have much left in me.
“Yes,” she whimpered.
I grunted and forced myself to hold on a little longer as I pounded this girl’s ass. I straightened back up and gripped her sides hard as I thrust myself deep inside her with each stroke. The sight of her ass swallowing up my cock would be burned into my mind for a long time after this.
Finally, I could hear the familiar tells that Madison was about to her cum. Her moans became increasingly frantic, and her breathing was rapidly growing faster and faster.
I let myself lose control. I fucked her hard and fast now. With each stroke I sank my cock deep inside her ass, my balls slapping against her ass cheeks as I pounded her. The feeling of her asshole tightly gripping my cock was incredible. And the fact that I was fucking my girlfriend’s little sister in the ass was unbelievable.
“Fuck, fuck, fuck, fuck, FUCK!” Madison cried out. “I’m gonna cum Brian, oh my GOD!”
Madison’s eyes rolled into the back of her head and her toes curled as her orgasm hit. I felt her ass begin to pulse and spasm around my cock, and that immediately pushed me over the edge.
“Fuck, I’m cumming too,” I grunted. I grabbed her hips and sunk myself deep inside her as I shot the first rope of cum deep into her ass. Finally.
“Fuck,” Madison cried as she felt my cock pulse and spasm as I unloaded inside her. Her fingers toyed wildly with her clit as she came with my cock deep inside her. I couldn’t control my moans as I shot another four ropes of thick, hot cum inside her.
I quickly slid my cock out of her once my orgasm finished. Madison was breathing hard, but she wanted more.
“Your turn, Jordan,” she grinned. “I don’t think you’ll be needing any lube. Brian took care of that for us.”
“Jesus Christ,” I breathed. I scooted to the side and sat down as Jordan took my position. His cock was already rock-hard.
Just as I did, Jordan took a moment to appreciate the sight before him. Madison was laying on her back, legs spread, her pretty, pink pussy and gorgeous tits on full display. And below her pussy, her tight little asshole, now with my cum beginning to leak out of it, waiting to be filled by a second cock.
Madison gently toyed with her clit as Jordan’s eyes ran greedily over her body. Finally, once Jordan had enough, he moved forward and pressed the head of his cock against Madison’s now cum-covered asshole. The fact that he would be using my cum as lube to fuck Madison’s ass was in and of itself insane.
“Ready?” Jordan asked.
“Fuck yeah,” Madison whimpered. “Fuck my ass, Jordan”. She began rubbing her clit more intensely as Jordan thrust forward. Madison’s asshole, slick with the fresh load of cum I had left inside her, readily gave way to this new intruder.
Jordan moaned as he sank his cock into Madison’s ass. He stopped when he was half-way inside her, giving Madison a chance to adjust to his impressive girth. Jordan ran his hands over her body, caressing her stomach and her thighs and her breasts. He pinched her nipples between his fingers and groped her breasts as he enjoyed the feeling of Madison’s asshole tightly gripping his cock.
“Okay,” Madison breathed. “Give me the rest. I want all of that cock inside me.”
The two of them moaned softly as Jordan slid the rest of his erection into her asshole, and Madison’s eyes rolled into the back of her head as he bottomed out inside her.
“Fuuuuck,” she breathed. “Oh my God.” She was already moaning loudly now, no doubt loving the feeling of Jordan’s massive cock filling her butt.
Jordan began to fuck her slowly, using shallow thrusts with only the top-half of his cock for now. The two of them moaned together as Madison enjoyed taking her second cock of the night in her asshole.
It wasn’t long before Jordan was fucking her faster. Madison’s moans and grunts became more frantic as Jordan began to really pound her ass. With each thrust, his balls slapped against her buttcheeks and her body shook. I was surprised Madison was taking his thick cock in her ass so well, but she appeared to love how much he stretched and filled her.
“Your ass is so fucking tight,” Jordan grunted. “I can’t take much more of this.”
“Cum for me,” Madison grunted. “Give my ass a second load of cum. Fuck my tight little asshole, Jordan!”
Jordan did exactly as I had done. He gripped Madison’s side and thrust himself deep into Madison’s ass as he began to unload inside her. He groaned loudly as he pumped her butt full of a second load of thick, white cum. Madison looked like she was in heaven.
“Fuck yeah,” Madison whimpered. The two held eye contact as Jordan’s cock painted the inside of Madison’s ass.
Jordan finished cumming and slid his cock out of Madison. Madison’s tight butt now had a healthy flow of cum dripping out of it onto Ashley’s pillow.
“I think Ashley is gonna need a new pillowcase,” Jordan chuckled, watching as his and my cum slowly trickled out of Madison’s punished hole.
Madison laughed. “You guys really filled me up.”
“Did you like it?” I asked.
“Fuck yeah,” Madison said. “Having you guys fill my butt with your cum was amazing.”
“Are you sore at all?” Jordan asked.
“Hmm,” Madison said, contemplating his question. “Not really? But maybe that’ll change. Hopefully not, though. Do y’all wanna put a towel under my ass real quick?” she asked.
Jordan nodded. I handed him a towel as Madison lifted her butt up off Ashley’s pillow. Jordan slid the towel under her ass and moved Ashley’s pillow.
“Gimmie her pillow,” I said to him.
Jordan handed me the pillow. I slid the pillowcase off and through it on the floor by Ashley’s dirty clothes hamper. I put the pillow back in its original position for now.
Madison was still laying on her back. She had brought her legs up so that they were bent at the knee but still spread, giving Jordan and I a perfect view of her pussy and her asshole. She sighed.
“Is there still cum leaking out of my butthole?” she asked.
“Yeah,” I laughed. “A fair amount, really. I guess we both came a lot.”
“That’s so hot,” Madison said. “Jordan, feel free to shoot a load inside me whenever you come over, honestly.”
“Holy shit, really?” Jordan asked.
“Yeah,” Madison said. “If it isn’t obvious, I very much enjoy being butt-fucked, and I especially like it when guys cum in my ass, apparently.”
“Good deal,” I laughed.
Madison glanced at me. “How’d it feel to finally fuck my butt, Brian? Was my butthole as tight as you imagined?” She giggled.
“Honestly, it was fucking incredible,” I said. “You were so tight. I’m shocked I lasted more than a few seconds.
“Agreed,” Jordan said.
“What about you?” I asked. “Was anal as good as you imagined?”
“Oh yeah,” Madison said. “Fuck yes it was. I can officially say that I love taking cock up my ass.”
“Lucky me,” I grinned.
We just chilled for another couple minutes, not really saying much. After a little bit, Jordan broke the silence.
“Y’all mind if I shower real quick?” Jordan asked. “I have a change of clothes in my backpack. I’ll probably call an Uber right before I get in.”
“Sure,” I said. “Just grab yourself a towel from the linen closet in the hallway, you know where it is.”
Jordan nodded. He grabbed up his clothes and dashed into the hallway, quickly grabbing a bath towel before ducking into the bathroom. Madison and I heard the shower turn on. She grabbed her phone and started browsing, but otherwise stayed laying on her back as she was. The sight of her legs spread like that with her pussy on full-display and her abused little asshole clearly visible was honestly making me hard again, despite the fact that I must’ve had three or four orgasms by now.
Madison glanced over at me and saw me staring at her ass. Her eyes darted to my cock and she giggled at the sight of me being hard again already.
“If you wanna have another go, be my guest,” Madison said.
“Can you roll onto your stomach?” I asked.
Madison nodded and adjusted herself so that she was laying flat on her stomach. I grabbed the bottle of lube and scooted over to her. I used one hand to spread her ass cheeks while I squirted some lube onto her asshole with the other. I shifted again so that I was standing on my knees, straddling her ass. I spread her ass enough to align my cockhead with her asshole.
“Ready?” I asked.
“Yep,” Madison said. She was still browsing her phone, clearly more than happy to let me use her asshole to get off again since I was still horny.
I thrust forward and sank my cock into her asshole, which gave very little resistance this time around. Madison moaned softly as I immediately began to fuck her. I had no intention of making this last. I just enjoyed the feeling of her butthole gripping my cock. I thrust my cock all the way inside her and stopped fucking her long enough to squeeze both of her asscheeks. Then I braced myself on one arm and resumed pounding her ass while I squeezed her buttcheeks with my free hand. I gave her a good spank and began to fuck her harder. With each thrust my cock plunged deep inside her ass. I fucked her hard and fast for another two minutes before I climaxed.
“Fuck,” I grunted. “I’m gonna cum again.”
I sank my cock inside her and gripped her ass as I began to ejaculate inside her. Madison actually moaned softly as I filled her butt for the second time tonight. I didn’t cum as much as I did the first time, but she still got another sizable load in her bottom — the third one of the evening.
Once my orgasm finished, I slid my cock out of her ass and collapsed on the bed next to her.
“Thanks for that,” I chuckled.
“My pleasure,” Madison giggled. “You’re welcome to use my ass whenever you want too, as long as I’m not busy. Except for right now — I think my butthole needs a bit of a break. Just for a little while, at least.”
“That’s fucking awesome,” I laughed. “Thanks.”
I laid there with my eyes closed until Jordan came into the room. “Alright y’all, I finished showering and my Uber is gonna be here in two minutes. I’ll catch you next weekend if not later this week, Brian. And it was nice meeting you, Madison,” he said.
“I’d get up and hug you, but I’m kind of gross at the moment,” Madison laughed. “It was great meeting you too though.”
Jordan laughed. “No worries, I’ll see y’all later.” He closed the door behind him and went upstairs.
“See ya,” I called after him.
I closed my eyes again. I was ready for a nap, as was Madison, apparently. She turned her phone off and laid next to me, closing her eyes too. It wasn’t long before we were both asleep, laying naked on Ashley’s bed, with my cum still dripping out of Madison’s ass.
We awoke maybe three hours later. Ashley would be home in less than an hour, most likely. Alyssa would be here shortly after that. I was the first to wake up. I grabbed my phone and saw I had several missed texts from Ashley. I groggily typed out a response and hit send.
I put my phone down and slowly sat up so as not to disturb Madison, who was still asleep. She was laying on her stomach with her arms folded beneath her head. She looked so peaceful, which was almost funny considering this same girl just let her sister’s boyfriend and his best friend take turns fucking her in the ass. I traced the length of her naked body with my eyes, starting with her feet, running up her calves and her thighs. I paused and admired her ass for a moment. Part of me couldn’t believe that I had pumped several loads into that big butt of hers just a few hours prior. I ran my eyes up her back and paused to admire her face. She really was quite beautiful; she had pretty eyelashes and gorgeous hair. She looked a lot like her sister.
I spent another few minutes sitting there in silence, not really thinking about anything. I guess I was mostly just processing the events from earlier in the evening. To be clear, there were no regrets on my end. Tonight was easily one of the hottest experiences of my life to date, and I think Jordan felt similarly. I made a mental note to check in with him tomorrow after he had some time to process what happened. But as I believe I’ve mentioned several times now, he and Kristen have an open relationship of sorts, so I doubt there would be any issues from him (or Kristen for that matter). Plus I don’t know if Kristen is a big fan of anal or not (she could be for all I know), but if not, then I’m sure she’d be happy that Jordan could fulfill his “anal desires” elsewhere.
My phone buzzed. I picked it up and checked the notification; Ashley would be home in about twenty minutes or so. As I was typing out my response, Madison stirred a bit and then woke up. She opened her eyes and blinked twice before stretching and yawning.
“Hey Brian,” she said sleepily. “What time is it?”
“Nine thirty-five,” I said. “Ashley will be home soon, like twenty minutes or so.”
She sat up and rubbed her eyes gently. “I need a shower.”
“Me too,” I chuckled.
“Do you wanna join me?”
“Of course.”
I grabbed some clothes from my backpack, along with my phone, and followed Madison to the bathroom. I locked the door behind me, but realized Ashley might get back before we finished showering, so I unlocked the door. Madison stood in front of the mirror. I came and stood next to her. Our eyes scanned over our naked bodies.
Madison reached over and lifted my soft penis up with her index finger. “This might be the first time tonight that you aren’t hard,” Madison giggled.
I laughed. “Oh, I imagine he’ll perk up soon.”
I decided to take the opportunity to brush my teeth. (I kept a toothbrush at Ashley’s house as I stay over frequently.) Madison followed suit.
“How are you feeling?” I asked after we had both spit out our toothpaste.
“Fine,” Madison asked. “Physically, that is. Mentally I am also fine, though. You?”
“More than fine,” I grinned. “Tonight was pretty great.”
“Yeah, it was,” Madison giggled. “I’ve wanted that for a long time.”
“Me too,” I said.
“Honestly, I wish you weren’t limited to fucking me in the ass,” Madison sighed.
“Yeah?” I chucked. It was still amusing to see Madison speaking in such a brazen fashion, given I originally knew her as Ashley’s shy little sister. I suppose that version of Madison was long gone though. That Madison wouldn’t have let her sister’s boyfriend and his best friend take turns cumming in her ass, of course.
“Yeah,” Madison said. “I haven’t been fucked like that in a long time. It would feel so good.”
I nodded in agreement. “Yeah, it’d be pretty great.”
“And it’d be so dirty, y’know? My older sister’s boyfriend fucking my pussy. God.”
“Yeah,” I said. My cock was rapidly getting hard again. “But to be fair, taking my cock in your ass is pretty fuckin’ dirty.”
“That’s true,” Madison laughed. “And letting your best friend fuck me in the ass is also pretty wild.”
“I have to ask,” I said, hesitantly. “What would Alyssa think of all this?”
“She wouldn’t be happy,” Madison said grimly. “Honestly, she was so turned on by you and Ashely having sex that one night. If I had just been open about this from the beginning, I bet she would’ve been on-board.”
“Yeah,” I said softly. “You’re probably right.”
“But I actually don’t think she’d be too upset.”
“Really?”
“Yeah,” she sighed again. “Obviously both she and I are bi, right?”
“Mhm,” I said. I was quickly typing out a message to Ashley that Madison and I were about to shower, and we’d probably still be in the shower when she got back. As we talked, I walked over to the shower and turned it on. Madison followed, and once the water was warm enough, we got in together.
“So she actually has a couple of guys she hooks up with sometimes,” Madison said softly.
“What? Really?” I was a bit shocked by this.
“Yeah,” Madison said. “Before we started dating, she explained that, although she’s attracted to both guys and girls, it’s hard for her to be completely satisfied sexually without dick, basically.”
“Wow, okay,” I said.
“She told me that, if she and I dated, she would want to still hook up with these two friends with benefits that she had. And to be clear, she didn’t force me into agreeing with her. Like she wasn’t manipulative. She said that she completely understood if that made me uncomfortable, but that she didn’t want to be sexually exclusive in that respect. And she said that I was obviously allowed to have one or two friends with benefits of my own.”
“How often do they hook up?” I asked.
“I’m not sure,” Madison said. “We don’t talk about too much. She’d tell me if I asked, and admittedly it’s a bit of a turn-on to imagine her getting fucked by some guy for reasons I don’t care to explore right now, but I usually just don’t ask her about it.”
“I see,” I said. “So you don’t think she really would’ve cared if you had wanted to hook up with me?”
“Right,” Madison said. “I mean, obviously it’s more than a little weird, given you’re my sister’s boyfriend. But I doubt that Alyssa would have cared too much. It might have even been a turn-on for her the way it is for me.”
“Why didn’t you tell her then?”
“I don’t know. Maybe I’m just used to not talking about this kind of thing with her. But obviously that doesn’t make any sense.”
“Right,” I said. “And I guess she’s open to you and Ashley messing around?”
“Well, yeah,” Madison said. She was shampooing her hair at this point while I was washing my body. “I mean, we all fooled around that one night a few weeks ago. And I think everyone knows what the expectations for tonight are.”
“But she doesn’t know that you and Ashley have had sex, or whatever, aside from that one night?”
“Right,” Madison sighed. “I’m gonna talk to her after tonight, assuming everything goes well.”
“About what?”
“I just want to be transparent with her going forward, at least. Like I want her to know that Ashley and I have sex and you and I have sex.”
“Makes sense,” I said. I also thought Madison should come forward and be honest about how she was already hooking up with Ashley and I regularly, but I didn’t say anything about that. Not yet, at least.
“And I also want to make it clear that she’s welcome to hook up with you and Ashley one-on-one, like without me there, as well, of course. It’d be more fair that way.”
I chuckled. “Do you think she wants to do that?”
“Well, I’m not completely sure,” Madison said. “But she has said that she thinks Ashley is super hot. And she’s very much into you as well. I don’t know if she actually wants to fuck you guys or not though.”
“Wow,” I grinned. “That’s good enough for me. We’ll see what happens, I guess.”
“Yep,” Madison said. She had finished washing her hair and was almost done washing her body. I was done.
I was about to step out of the shower when I heard the door open and then quickly shut. My heart skipped a beat, but I knew it must’ve been Ashley.
“Hey guys,” she said. Indeed, it was Ashley.
“Hey,” Madison said.
“Hey baby,” I said, peaking my head out from behind the shower curtain. Ashley smiled and came up to give me a quick kiss.
“It sounds like y’all have had a fun evening,” Ashley said, grinning. She was stripping off her clothes as she talked.
“Uh, yeah,” I laughed.
“It was pretty great,” Madison said.
“Well, I hope you guys are still horny enough for tonight,” Ashley giggled. She was completely naked now.
I stepped out of the shower. “I’m done, you can get in if you want.”
Ashley quickly handed me a towel as I was dripping everywhere before joining Madison in the shower.
“I mean, I’m never not horny,” I laughed.
“Me too, honestly,” Madison said.
Suddenly there was a loud SMACK followed by a series of giggles from both sisters.
“What happened?” I asked.
“Ashley just slapped my butt,” Madison said, still giggling.
I pulled back the external shower curtain (like, the one on the outside of the shower; there are two), which was opaque. The inner shower curtain was translucent so I could see them in the shower. Madison was closest to the shower head, and she was facing away from Ashley. Ashley’s nipples were hard.
“Good idea, Brian,” Ashley said, referring to me moving the shower curtain out of the way so I could see.
Ashley reached down and squeezed her sister’s ass. Madison bit her lip. Ashley stepped in close and pressed her naked body against her sister. Madison could feel Ashley’s hard nipples pressed up against her, especially because of Ashley’s piercings.
Ashley maintained her grip on Madison’s ass as she leaned in and whispered in her ear, “I hear you let my boyfriend fuck you in the ass tonight, huh?”
“Uh huh,” Madison said, nodding her head. She was smiling and biting her lip again.
“How many times did he get to cum inside your ass?” Ashley said. She was squeezing Madison’s left ass cheek with her left hand. She reached around with her right hand and took Madison’s right breast in her hand, pinching her sister’s nipple between her thumb and index finger.
“Twice,” Madison gasped. Ashley kissed Madison’s neck, biting it softly.
“How did it feel?” Ashley said. She released Madison’s ass and reached around to grab her other breast, squeezing both of them firmly.
Madison whimpered. “It felt so good,” she said softly.
“You like taking my boyfriend’s cock in your ass, don’t you?” Ashley purred. She was kneading Madison’s breasts with her fingers while pressing the rest of her body up against her sister’s.
“Yes,” Madison whimpered. “I love when he fucks me in the ass.”
“You’re such a slut,” Ashley said. She kissed Madison’s neck again and pinched both of her nipples, pulling on them hard. Madison cried out, but she clearly loved the pain. Ashley kept tugging on her sister’s nipples while she bit and kissed her neck.
Madison moaned loudly. Ashley let go of her right breast and slowly traced her hand down her sister’s tummy. She snaked her fingers along either side of Madison’s vulva. She was still gripping Madison’s left breast firmly.
Ashley let her middle finger run down the center of Madison’s vulva, passing lightly over her clit before reaching the entrance to her vagina. She was basically cupping Madison’s pussy now. Slowly, Ashley hooked her middle finger inside her little sister’s vagina. Madison was incredibly wet. Ashley slowly slid her middle finger in and out of Madison’s pussy, listening to her little sister’s moans of pleasure.
Ashley slid her finger out of Madison’s pussy as she released her left breast. She wrapped her right arm around Madison’s stomach as her left hand found Madison’s pussy. Ashley hooked two fingers inside Madison’s cunt now and began to fuck her a bit more firmly now. Madison moaned her sister’s name.
Once her two fingers were completely coated with Madison’s juices, Ashley slid them out of her sister’s pussy and quickly brought them around back so as to avoid the water. Ashley used her other hand to spread Madison’s ass cheeks. Carefully, Ashley reached down and brought her fingertips against Madison’s asshole. Ashley’s right arm was still wrapped around Madison’s tummy, holding her firmly in place. Madison’s eyes were closed and her head was tilted back. The water was mostly landing on her chest.
Ashley pressed her middle finger forward slightly. Madison’s ass resisted just slightly before Ashley’s finger disappeared into her asshole. Madison groaned loudly. Ashley slid the entirety of her finger into her little sister’s ass. And now, with her finger firmly embedded in Madison’s ass, Ashley moved her right hand down and began to massage Madison’s clit. Now, I think I’m pretty good at giving head and making girls cum with my fingers. But Ashley was an expert. She worked her little sister’s clit like a pro. Madison reached back and gripped Ashley’s hair with one hand while she braced herself against the wall with the other. Ashley began to finger-fuck Madison’s asshole while she rubbed Madison’s clit, causing Madison to cry out and moan loudly.
And within two minutes, Madison was on the brink of orgasm. “Fuck, oh my God,” Madison cried. “You’re gonna make me cum, Ashley. Fuck, please don’t stop.”
“Good girl,” Ashley cooed. Ashley was always so submissive to me, but she was definitely being dominant towards her little sister. “Cum for me. Cum for your big sister.”
“Ughhhhhh,” Madison groaned. “Fuck baby, oh my fucking God. Oh fuck, oh fuck!”
“That’s right,” Ashley said. “Cum for your sister, baby girl.”
Madison let out another big moan before crying out, “Ashley, I’m gonna come! Fuck, fuck, fuck!”
Ashley held her little sister tightly as she rubbed her clit and began to cum. Madison’s legs trembled as her orgasm rocked throughout her body. The feeling of her big sister finger-fucking her ass and massaging her clit was overwhelming. Madison moaned and cried out loudly in between gasps for air as Ashley pleasured her.
Once Madison’s orgasm subsided, Ashley slid her finger out of Madison’s ass, and Madison turned to face Ashley. She looked into her big sister’s eyes for a brief second before placing one hand on Ashley’s cheek and another on Ashley’s side. Madison tilted her head and brought her lips against Ashley’s. The two kissed deeply. Ashley’s tongue darted out and traced gently across Madison’s lips before retreating. Madison’s tongue followed Ashley’s, tracing gently across Ashley’s lips. Ashley gripped Madison’s ass with one hand while pulling her in closer with the other. Their tongues began to intertwine now, and the two sisters moaned softly as they made out.
I stood and watched, fully erect, as my girlfriend passionately made out with her little sister. Their hands moved over one another’s bodies greedily, stopping to caress each other’s breasts, thighs, and bottoms as they frenched. After another few minutes, Ashley broke away. She gazed into her sister’s eyes for a moment before smiling. She went in for one final kiss before breaking away completely.
“That was nice,” Madison said. She was blushing hard
“I thought so too,” Ashley smiled.
Madison sighed and stepped out of the shower. I wrapped a towel around her and she tried off while Ashley finished showering. Madison quickly noticed my hard cock. She reached down and held it in her hand, not stroking it or anything, but just enjoying the feeling of it in her fingers.
She leaned in close to me and whispered in my ear, “After tonight, you can just bend me over the sink and use my pussy to relieve yourself in situations like this.”
She moved back and looked at me for a reaction, blushing again. I held her gaze for a moment, biting my lip, before grabbing her and pulling her in. I brought her lips against mine, and she immediately slid her tongue across my lips. She dropped her towel and reached down to stroke my cock slowly as we frenched. I moved against her slightly and backed her up against the wall. She and I continued just like this, making out while she slowly stroked my cock, until Ashley had finished showering. She stepped out and grabbed herself a towel, watching as her little sister and boyfriend made out against the bathroom wall.
“Well, I’m glad to see we’re all still plenty horny,” Ashley laughed.
I broke away from Madison and the two of us laughed. “Clearly,” I said.
“When is Alyssa going to be here?” Ashley asked, looking at Madison.
“Uh, does anyone know what time it is?”
I grabbed my phone and checked. “It’s 10:05.”
“Oh, she’s probably on her way,” Madison said. “Let’s get dressed. She told me she’d be here around 10:30.”
“Alright,” I said.
We exited the bathroom. I followed Ashley into her room while Madison went to her room to change. Ashley let me walk past her before shutting and locking the door behind her. She got up onto the bed and laid on her back, spreading her legs wide open. She was ready for me. Without saying a word, I climbed onto the bed and immediately sank my cock inside her. She began rocking her hips as I brought my lips against hers. I fucked her with slow, deep strokes, bottoming out inside her each time.
Ashley’s pussy gripped me tightly, but I was able to stave off my orgasm for about ten minutes. Outside Ashley’s bedroom door, Madison was setting up for the evening. She had brought out wine glasses, shot glasses, cups, and water bottles. Ashley and I were making no effort to be quiet; her parents had gone to bed about an hour ago. So Madison heard us, clear as day. She heard Ashley’s moans of pleasure as I fucked her pussy. She heard Ashley cry out when her first orgasm hit. And Madison heard her big sister announce that she was cumming for her second orgasm too. And finally, Madison heard me groan that I was about to finish, and she heard Ashley plead for me to cum deep inside her pussy. And I did. I sank my cock into my girlfriend’s pussy and ejaculated deep inside her.
Once my orgasm ended, I kissed Ashley deeply again. “I love you,” I said.
“I love you too.”
Ashley got up, grabbed her clothes, and quickly waddled to the bathroom to clean up. Madison laughed. I finished getting dressed and walked outside of Ashley’s bedroom to join Madison on one of the couches.
“How was the sex?” Madison smirked.
“Amazing,” I grinned. “I’m a lucky man.”
“Clearly,” Madison laughed. “Did you finish inside her?”
“Of course!” I said. “You jealous?”
“A bit,” Madison giggled. “But I’ll get my turn soon enough.”
“I hope so,” I said.
A moment later, Ashley came out and joined us on the couch, sitting to my right. Madison was on my left. We sat on our phones and chatted while we waited for Alyssa to arrive. The night was only just beginning.