Let me give y’all a bit of backstory in case you don’t already know me. My name is Brian, and I’m dating this girl named Ashley. We’ve been together for a few years now. Ashley is a very… outgoing person. She’s not shy at all, and in fact, she’s a bit of an open book, especially when it comes to her sex life. I realize that’s a lot to tell you right off the bat, but it’s relevant to this story. Ashley’s adventurousness has led to us having a number of incredible experiences with other like-minded people (namely this one couple we’re good friends with, Jordan and Kristen) as well as Ashley’s younger sister, Madison, and Madison’s girlfriend, Alyssa! Fair warning, a lot has already happened between us, so we’re going to hit the ground running from this point onward. Feel free to check out my previous posts if you want some backstory (though it isn’t necessary!).
Believe it or not, Jordan (who is my best friend) and I had spent the first part of the evening drinking with Madison. One thing led to another, and Madison may have sucked our cocks, received a good face-fucking or two, and eventually let us fuck her in the ass several times. If that sounds like a lot, well, it was. I’m still kind of in shock that I spent the past few hours fucking my girlfriend’s little sister in the ass. If you’re interested in hearing about that — or all the stuff that came before it, as there was quite a lot of build-up — then I again recommend that you check out some of my earlier stories.
The long and short of the backstory between all of us is that Madison started watching Ashley and I have sex a while back. Things sort of progressed from there, and Madison slowly became more and more involved. It got to the point where she and Ashley were actually having sex regularly, probably more often than Madison and Alyssa, and Madison and I were fooling around just as often. But let me be clear, she and I have not had sex. We’ve just done… basically everything besides that. Especially after earlier tonight, we certainly checked off a few more boxes.
So with all that out of the way, I should probably get back to the present. Like I said, Jordan and I had spent the earlier part of the evening drinking with Madison, and that led to him and I fucking her in the ass, to be blunt. I suppose I should also add that we also face-fucked her for a bit, which was great. Madison is really great at giving head, which was originally a bit of a surprise given she’s been dating Alyssa for a while now. But I digress. It was now around 10:10pm or so. Alyssa was on our way and would be here in about twenty minutes. Madison, Ashley, and I were just sitting on our phones and talking. We were still on the couches outside of Ashley’s room (in the basement). Madison and I were describing the night’s events to Ashley, who was clearly extremely turned-on by what we were describing to her.
Madison and I first described how Jordan and I had been drinking and playing video games when Madison casually came out wearing a skimpy little tank top and some athletic shorts. To me, it had been clear that she had an ulterior motive at that point, but she totally tried to play it off like she wasn’t trying to get semi-laid. (I say “semi-laid” because her pussy was off-limits.)
I told Ashley how Jordan immediately recognized Madison as the girl who was sucking my dick in those videos I sent to him the other day. And then Madison explained to Ashley how she wasted no time getting my and Jordan’s cocks in her mouth. Madison told her sister about how excited she was at the prospect of having two hard cocks to play with instead of just one.
It was around this point in the conversation when Ashley said “fuck it”, pulled her pants down — followed shortly by her panties — kicked them off her feet, leaned back, spread her legs, and started openly masturbating. Madison and I chuckled and enjoyed the view as Ashley played with her pussy. She slipped her fingers in between her lips before sliding two fingers inside herself. She began to gently massage her clit with her other hand. She was already very wet.
“Please, don’t mind me,” Ashley grinned. “This is just too juicy not to touch myself.”
“What’s too juicy?” Madison laughed. “Our story, or your pussy?”
Ashley giggled. “Both, really.”
I quickly described how Madison had first worked Jordan’s cock for a bit before shifting over to give me some attention. I made sure to include that Madison had addressed me as “daddy” when I instructed her to go and make Jordan cum, which made Ashley moan audibly. Madison and I both remained fixated on the action going on between Ashley’s thighs. Madison absolutely loved watching her big sister touch herself. There were few things that turned her on more than that.
Next, Madison described how it felt to take Jordan’s cock into her mouth. She told Ashley how nice and big it was, and how nice it felt to run her tongue along Jordan’s shaft and around the head of his cock. She talked about taking Jordan’s balls into her mouth and sucking them gently while she stroked his shaft. Madison explained how good it felt when Jordan started to climax, and how she could feel each rope of cum coat her tongue and throat. Ashley was breathing pretty hard by this point, but we were just getting started.
Next, I told Ashley about how I had Madison lean back against the couch. I told Ashley how I fucked her little sister’s mouth in front of my friend, and then how my friend took a turn once his cock was hard and ready again. I described how Madison’s eyes had watered as she took our cocks in her throat. I told Ashley how good it felt to slide my cock all the way into her little sister’s mouth — so that my balls were resting on her chin — and hold it there for a second while Madison gagged and choked. I told Ashley that her little sister had looked so hot with our cocks in her mouth, and that Madison had been our little slut for the evening.
As if that all wasn’t enough, Madison excitedly detailed how I had shot my cum all over her face and her tits while Jordan watched, eagerly waiting for his turn to fuck her mouth. She described how much it turned her on to feel each rope of hot, white cum land across her face and her tits, knowing another man was about to start using her mouth next. Then Madison told Ashley about how she had sat there, absolutely covered in our cum, and brought herself to a huge orgasm while Jordan and I enjoyed the show. She loved touching herself in front of us. She loved that we could see her pussy, and she loved how dirty she felt, freshly face-fucked and covered in cum. Madison said that it was one of the best orgasms she ever had.
“My God,” Ashley groaned as she rubbed her clit. “You are such a fucking slut Madison. What the fuck.”
“I guess it runs in the family huh sis,” Madison said. “After all, you’re sitting here touching yourself to this.”
“Fair enough,” Ashley grinned.
Ashley was getting close to getting herself off. Her toes were curled, she was sliding her fingers in and out of her pussy pretty fast now, and she was breathing pretty hard too. She managed to last until Madison and I told her about how she had let Jordan and I fuck her in the ass repeatedly. At that point, she lost it. Ashley was no match for Madison’s recollection of the night’s events. Listening to Madison — her little sister — talk about how she spent the evening taking two cocks up the ass was too much for Ashley. Especially because one of those cocks belonged to me, her boyfriend.
“Awh, can’t you edge a little longer?” Madison teased as Ashley cried out that she was almost there. “Don’t you wanna hear more about how your little sister spent the evening getting fucked in the ass by your boyfriend?”
“Fuck, fuck, FUCK,” Ashley moaned. Her pussy was so incredibly wet, the sound of her fingers sliding in and out of her hole filled the room.
“Your boyfriend shot his cum into my ass over and over, you know,” Madison said. “He and his best friend pumped my tight, virgin asshole full of cum while you were at work.”
Ashley let out another loud moan. She threw her head back and arched her back as she started to climax.
“Their cocks felt so good too,” Madison continued. “I loved how your boyfriend’s big cock felt in my ass. He made me feel so full. I can’t wait to fuck him again.”
Ashley gritted her teeth and moaned as she writhed around in pleasure. No doubt she was picturing Madison taking my cock in her ass.
“You know what? I’m gonna let your boyfriend fuck my ass every time you go to work,” Madison teased. “Everytime you go to work, you’ll know I’m back home, letting your boyfriend pump his cum into my tight little asshole.. I’ll be his personal little fucktoy whenever you’re not around.” I couldn’t believe my ears. Jordan and I must have awakened something inside her tonight. That, or she was just obscenely horny after being shared by two guys. Either way, I was all for it!
“FUCK,” Ashley cried out. Her whole body was tense as she desperately worked her clit. Finally, her orgasm finished, and she collapsed in a heap, breathing hard, gasping for breath.
“Wow,” she sighed. “Thanks for that. Holy fuck.”
“You’re welcome,” Madison said cheerily. “I’ve got to pay you back somehow. I wasn’t lying when I said I loved having your boyfriend fuck me in the ass.” She winked at me before continuing. “Giving you a good story is the least I could do.”
“You certainly know how to tell a good story,” Ashley smiled. She had stopped fingering herself, but she left her legs open so Madison and I could enjoy the view of her pussy (and her butthole, for that matter).
“I learned from the best,” Madison laughed. “I’ve heard you give so many graphic recollections of getting fucked. I should hope I’d be pretty good at telling you about how I got fucked for once.”
“You’re more than pretty good,” Ashley chuckled. “Were you serious about letting Brian fuck you in the ass whenever I go to work?”
“Yeah,” Madison shrugged. “If he’s horny, at least.” She looked at me. “I already told you that you could fuck my ass whenever you wanted to, didn’t I?”
“You did indeed,” I grinned.
“Exactly,” Madison said. “That would certainly include whenever you’re at work.”
Ashley nodded approvingly. “Works for me. Somebody needs to be able to get Brian off when I’m not around. Who better than my little sister!”
Madison and I laughed. “I’m all for it,” I said.
I checked my phone once Ashley’s orgasm finished, and saw that it was 10:28pm. So, we decided to stop telling the story — we could fill Ashley in on any remaining details later. Ashley went and grabbed a bottle of wine, a beer, and four wine glasses. She poured herself and Madison a glass of wine and handed me my beer.
“Thanks babe,” I said, cracking open the can and taking a big swig.
Ashley handed Madison her glass.
“Thanks sis,” Madison said. Madison’s phone buzzed. She unlocked it and read her text. “Alyssa is here. Should I tell her to just come in?”
“Yeah,” Ashley said. “The front door is unlocked. Mom and dad are asleep. Just tell her to lock it behind her.”
“Gotcha,” Madison said. “Oh, you should probably put your pants back on, Ashley.”
“Oh fuck, good idea,” Ashley laughed. She quickly threw her pants and panties back on. “Good save.”
“Mhm,” Madison said. “Though I hope I get to see your pussy again later.”
“Me too,” Ashley grinned.
Alyssa came downstairs about three minutes later. Ashley quickly poured her a glass of wine.
“Hey baby,” Madison said, smiling.
“Hey baby girl,” Alyssa replied with a smile. She had a look on her face — like a sort of “knowing” look. I wondered if she knew Madison had just taken two cocks in her ass tonight. I wouldn’t be surprised one way or another.
Ashley also topped off her and Madison’s glasses, as they had almost finished their own. I went ahead and finished my first beer and hopped up to grab a few more. “Anybody need anything while I’m up?” I asked.
Everyone gave some form of “no thank you” as their response.
“I am going to go change real quick though,” Alyssa said. She followed me as I walked to retrieve the beers until we passed the bathroom, at which point she went in and shut the door behind her.
I got back with my beers, cracked another open, and sat down. Alyssa had already finished changing. She was wearing a fairly low-cut, black tank top and red running shorts with a white stripe running down the sides. The girls were talking about Ashley and Alyssa’s shifts. The usual. Some annoying customers, shitty bosses, drama with coworkers because somebody fucked somebody they weren’t supposed to, somebody else got caught doing coke in the bathroom. Just standard service industry happenings.
“Tony and Alicia got caught fucking in the bathroom again,” Ashley said. Tony and Alicia were coworkers of hers. They were in an on-again off-again relationship, and there was always drama with them. Apparently they had a reputation for fucking and doing coke in the bathroom at the restaurant. Somehow they’ve been lucky enough to only get caught by other employees, otherwise they’d likely be fired on the spot.
“Of course they did,” Madison laughed. “How many times is that now?”
“As far as I know, they’ve been caught banging four times,” Ashley said. “Like, this was the fourth time.”
“Wow,” Alyssa said. “Can’t they just wait until their shift is over?”
“I’m pretty sure they go straight to one of their cars and fuck when their shift ends,” Ashley chuckled.
“Damn,” Madison said. “These horny motherfuckers.”
“It’s probably all the cocaine,” I said. “Doesn’t that shit make you, like, incredibly horny?”
“Does it?” Alyssa asked.
I shrugged. “That’s what I’ve heard.”
“You sure you don’t have a cocaine habit, Ashley?” Madison teased.
“What?” Ashley laughed. “No!”
“Oh, they’re onto you, babe,” I grinned.
“That would explain why you’re always so goddamn horny,” Madison said.
“She’s got you there,” Alyssa agreed.
Ashley laughed again. “Damn, I guess y’all caught me.”
“Do you play that up?” Alyssa asked Ashley, taking a sip of wine.
“Play what up?” Ashley asked.
“How horny you are,” Alyssa giggled. “Like, I know the joke is that Ashley has the sex drive of a thirteen-year-old boy. But, like, do you really?”
“I don’t know,” Ashley said. “What do you think Brian?”
I laughed. “That girl is insatiable,” I said. “She’d have sex three times a day if we had the time.”
“Really?” Alyssa said. “Damn, wow.”
“That’d be nice every once in a while,” Madison said.
“What would? Having sex three times in a day?” I asked.
“Mhm,” Madison said. “Like, I totally see the appeal of spending the whole day getting fucked.”
“That sounds very appealing,” Ashley giggled. The three of us laughed.
“No, no, it totally does,” Madison said. “But just, like, not every day! Just sometimes, I’d like to spend the day in bed getting laid.”
“Doesn’t have to be in bed,” Ashley winked.
“Good point,” Madison said. “Then I’d like to spend the day getting laid. In bed, in the shower, on the floor, wherever.”
“Mhm,” Ashley said.
“But just not every single day,” Madison said.
“What’s your, like, ideal frequency for having sex?” I asked.
“Depends,” Madison said. “If I’m not busy, then I wouldn’t mind having sex every day. But a few times a week, at least.”
“Yeah, a few times a week is good,” Alyssa said. “You can always go crazy some weeks if you’re in the mood.”
I nodded. “Makes sense.”
“Pretty sure I’ve asked Ashley this before,” Madison said. “And she said every day, at least, right?”
Ashley nodded. “I prefer to get dick at least once a day.”
“Which works for me,” I said. “I’m an everyday type of guy at the moment.”
“Hey, do you guys wanna play a game?” Ashley asked, clearly already feeling the effects of her wine. I think all of us were a bit tipsy at this point.
“What did you have in mind?” Alyssa asked.
“How about Never Have I Ever?” Madison suggested.
“Works for me,” Alyssa said.
“I’m down.” I said, taking another swig from my beer.
“Me too,” Ashley said with a sly grin spreading across her lips.
“How about you go first, Ashley?” I said. “Since you suggested it and all.”
“Okay,” Ashley smiled. “Everybody put up all five fingers.”
We all did as we were told.
“Now then,” Ashley said, pausing for a moment to think of a prompt. “Never have I ever smoked a cigarette.”
Madison rolled her eyes and put a finger down. “Were you targeting me? That was one time when I was, like, sixteen.”
Alyssa laughed. “Serves you right for trying cigarettes at all!”
Madison chuckled. “I suppose so, it was dumb.” She took a big sip of wine. “So who’s next?”
“Let’s go clockwise,” Ashley said. “So Brian, you’re next.”
I had been trying to think of a prompt while Ashley was doing her turn, but I hadn’t come up with anything yet.
I thought for another moment before saying, “Never have I ever accidentally walked in on two people having sex.” I’ve definitely walked in on people having sex before, but never by accident!
Madison thought for a moment. “How do you define walked in on? Because I come downstairs and hear you and Ashley going at it at least twice a week.”
Ashley laughed. “Hey now, we almost always have sex in my bedroom!”
“Almost always?” Alyssa inquired, taking a small sip of wine after she spoke.
“Well, yeah,” I shrugged. “Sometimes we’re out here. Like last week, I’m pretty sure we banged right where you’re sitting.”
“Oh my God,” Alyssa laughed. “You didn’t!”
“It might’ve been where Madison is sitting,” Ashley said, scratching her head. “I’m not really in the right state of mind to remember right now.”
“Oh, I think you’re right, Ashley,” I said.
“Yeah. Because I think I remember being able to see that painting –” Ashley gestured to this painting hanging on the wall behind Madison — “while I was riding you.”
“Oh, you were riding him?” Madison laughed. “Thanks, now I think I have the right mental picture.”
“Mhm,” Ashley said. “If it helps, I was completely naked, but Brian only had his pants down a bit.”
“Why weren’t both of you naked?” Alyssa asked.
“Well, I had just gotten out of the shower,” Ashley said. “And I was horny –.”
“As usual,” Madison interjected.
“Right,” Ashley laughed. “So I came over to where Brian was sitting, and I just got down on my knees, pulled his pants down, and started blowing him.”
“Wow,” Alyssa mused.
“It was pretty great,” I grinned.
“And once he was hard,” Ashley continued. “I sat down on his dick and started riding.”
“Sounds like a good time to me,” Alyssa chuckled.
“Oh, it was,” Ashley said.
“Where was I?” Madison asked. “I don’t remember this.”
“We were pretty quiet for once,” Ashley said. “I thought you might have gone to bed so I didn’t want to wake you up.”
“Ah, but if you had reason to believe I was awake, then you wouldn’t have bothered with trying to be quiet, right?” Madison said.
“Of course not!” Ashley laughed. “It’s more fun when you can be loud.”
“You’re not wrong,” Alyssa said in agreement.
Madison laughed and rolled her eyes. “Okay, well then I suppose I haven’t walked in on you guys doing it before.”
Alyssa thought for a moment before slowly putting a finger down. “I think I walked in on my sister having sex once? I’m not 100% sure because she won’t admit to it, but that had to be what she and her boyfriend were doing.”
“Probably was,” Madison said. “I take it you didn’t ask her?”
“Nope,” Alyssa chuckled. “I felt weird about it at the time. I don’t think I’d care now. If anything, I’d just tease her about it. Alyssa took another big sip of her wine as “punishment” for having to put a finger down. “It definitely looked like they’d been having sex though.”
“Yeah, if it looked at all like they were having sex, then they were probably having sex,” Ashley laughed.
Alyssa nodded. “Yeah.”
“So who’s next?” Ashley asked, looking at the group. “Alyssa is, right?”
“Yeah,” I said. “I just went, so she’s next.”
Madison, Ashley, and I turned and faced Alyssa, who was currently thinking about what to say.
After a bit of thought, Alyssa blushed and said, “Never have I ever done anal.”
Madison blushed a bit too, and then both Ashley and Madison started giggling. I have no idea if Alyssa had any idea that Madison had just spent the evening getting fucked in the ass by two different cocks. All I know is that I did not expect Alyssa to be the first person to give an overtly sexual prompt. I figured it’d be me or Ashley.
“Ooh, it looks like I got a few of you guys, huh?” Alyssa grinned.
“Mmm, I think you did,” I laughed. I took a big swig of my beer and put a finger down.
Alyssa giggled. “You’ve put your, erm, thing in a girl’s butt before?” Alyssa then turned and looked at Ashley. “Does that mean you’ve taken it in the butt before?”
Ashley laughed. “Oh, Brian’s put his ‘thing’ in my butt once or twice.”
Alyssa glanced at me and caught me mid-eye roll. “What?”
“Once or twice? Please” I said.
Ashley laughed again. “Okay, okay, maaaaybe I’ve taken it in the butt — oh, let me see — more times than I can count.”
“That’s more accurate,” I laughed.
“Wow, really? So you really like it then?” Alyssa asked, raising her eyebrows. “I mean, I understand why Brian would like it.”
“Oh yeah? Why would Brian like it?” Madison grinned. She was obviously trying to get Alyssa to say something dirty.
“Oh,” Alyssa said, blushing. “Well, I just have to imagine that the view would be pretty amazing. And I bet it’d make him feel really nice…”
“What would be so great about the view?” Ashley asked as though she really had no idea.
Alyssa blushed again. “I mean, I guess it would depend on the position you were in…”
“True, true,” Ashley said. “But, and I don’t know about you, but personally when I imagine two people doing anal, there’s one position that comes to mind more often than others.”
“Agreed,” I said. “It’s the way God intended it.”
Madison laughed. “God intended us to have buttsex in a specific position?”
“He must’ve,” I said. “Otherwise He wouldn’t have made the view so damn good!”
Ashley and Madison giggled. Alyssa blushed and started giggling along with them.
“I assume you’re referring to doggystyle,” Alyssa said. “Because the girl’s ass would definitely look great if she were on her hands and knees in front of you.”
“Exactly,” I grinned.
“Bingo!” Madison said.
“Yeah,” Ashley said. “I love it, personally. I get some crazy orgasms from anal, let me tell you.”
“Really?” Alyssa asked.
“Now she’s interested!” Madison laughed.
“Oh, yeah, Madison,” Ashley said. “Put your finger down!”
“I know, I know,” Madison laughed. “We’re all well-aware that I like putting things in my butt.”
“Girl, you really do like it though,” Alyssa laughed. “None of my friends finger their asses when they masturbate, but that seems to be your go-to now.”
“Alyssa!” Madison blushed. Obviously Madison wasn’t actually embarrassed, seeing as she’s had both Ashley’s tongue and my cock in her ass several times now. But she had to play it up a bit, I guess?
“No shame,” Alyssa said. “Apparently it feels really good.”
“You’ve never even tried putting so much as a finger up there?” Ashley asked. “Aren’t you curious? It’s, like, a-whole-nother-hole to play with.”
“Nope,” Alyssa shrugged. “But I guess I’m really missing out.”
“Uh, yeah,” Madison said. “Just a bit.”
“It’s just like Brian said,” Ashley chuckled. “God gave you an ass so you could have anal!”
“I didn’t say that,” I laughed. “But I’m not gonna dispute it either. That man definitely knew what he was doing.”
“For sure,” Madison said. “He knew guys would wanna put their dicks in our butts.”
“Mhm,” Ashley said.
“Y’all are crazy,” Alyssa laughed.
“Oh, so that means you’ve definitely never had someone eat your ass either, right?” Ashley asked.
“Nope, never,” Alyssa said. “But I take it that’s also a good time?”
“Extremely,” Ashley grinned. “Brian always gets me off that way before we do anal. I love it.”
“Damn,” Alyssa laughed. She took the last sip from her wine glass, after which Ashley immediately filled it back up. “I didn’t know y’all were so into butt stuff. And I didn’t know literally everything having to do with my asshole would feel so good.”
I shrugged. “It’s hot and it definitely feels good. What’s not to like?”
“How often do y’all…?” Alyssa asked.
“Oh, even I know this one,” Madison laughed. “Ashley can’t go more than a week without having a dick in her ass.”
“How do you know that?” Alyssa laughed.
“Please,” I grinned. “Ashley will talk about her sex life to anyone that’ll listen.”
“Good point,” Alyssa said. “Does she tell you whenever they do anal?”
“Mhm,” Madison said. “Literally — oh my gosh. Literally, the last time, she came into my room right after they finished. She just poked her head in and said, ‘guess who just got fucked in the ass!’”
Alyssa cracked up. “Really? Holy shit, Ashley!”
Ashley just smirked and shrugged. “I couldn’t help but brag.”
“But did you literally go straight to Madison’s room? You didn’t even make a pitstop in the bathroom first, for example?” Alyssa asked.
“Nope,” Ashley giggled. “Brian’s jizz was still in my butt at that point!”
“Good lord,” I laughed. “I actually didn’t know you did that.”
“I didn’t know your cum was still in her ass,” Madison said to me. “I mean, I figured it probably was. But she didn’t tell me.”
“Surprising,” I said. “Ashley usually doesn’t leave out such ‘important’ details like that!”
“Silly me,” Ashley said. “In any case, there’s definitely a ‘once a week’ minimum around here. In fact, Brian and I went anal-only for all of June last summer.”
“Really?” Madison asked. “That, I did not know.”
“Mhm,” I said. “It was a lot of fun, honestly.”
“Goddamn,” Alyssa said. “You must really like anal, Ashley.”
“Girl, that’s what I’ve been saying,” Ashley laughed. “I love taking it in the ass.”
“What inspired you guys to go a whole month of ‘anal only’?” Madison asked. “That’s another thing I didn’t know.”
“I saw something online about this couple that did it,” Ashley said. “It sounded fun. At first, we were only going to do a week. But then we were like, ‘why not go for longer?’”
“Mhm,” I said. “We started at the beginning of June, so after two weeks of anal-only, we just decided to do the whole month.”
“How often did you guys have sex that month?” Alyssa asked. “Like, last June or whatever month you said.”
“June, yeah,” Ashley said. “Hmm, it was a little less than usual, just because my ass can only take so much dick before it needs a break.”
“Yeah,” I said. “Your ass took quite the beating that month. I feel like it was at least three or four days a week.”
“Damn, that’s actually kind of low for you,” Madison chuckled. “You must’ve been a mess, Ashley!”
“Yeah, it was a bit rough,” Ashley said. “I masturbated a TON on the days where we were giving my ass a break.”
“Bro, it was non-stop,” I laughed. “Girl touched herself like four times a day.”
“Holy shit,” Alyssa laughed.
“But man did it feel good to take it in the ass again after a day or two off,” Ashley said. “Having a wait a day or two for dick always makes the sex amazing.”
“I bet,” Madison giggled. “What did you do on the off-days Brian?”
“I jacked off some of the time,” I said. “But Ashley gave me a ton of blowjobs too. At least one a day on our ‘rest days’. Usually while she was masturbating.”
“Damn, you’re a lucky man, Brian,” Alyssa smirked. “When your options are a blowjob or anal, I feel like it doesn’t get much better that.”
“I certainly can’t complain,” I grinned.
“Well, I guess you’ll have to try putting your finger in my booty sometime soon, Madison,” Alyssa said.
“Or two, maybe,” I said quickly. “Ashley says that two feels better than one.”
“Definitely two,” Ashley agreed.
“Yes please,” Madison grinned. “I’m all for it.”
“Okay, okay,” Alyssa said. “You can try putting two fingers in my butt then.”
“Fuck yes,” Madison said. “I owe y’all one,” she said with a laugh.
“You’ll have to let us know how you liked it,” I said. “You’ve gotta report back. For science.”
Madison laughed. “Oh, we will.”
“Of course,” Alyssa laughed. “I just hope I have a crazy orgasm like Ashley does.”
“I bet you will,” Ashley said. “But in my personal experience, a tongue feels better than a finger or two.”
“Oh gosh,” Alyssa blushed. “You really like that too?”
“Dude, yes!” Ashley said. “It feels fucking amazing. No joke. And it’s so hot.”
“Yep. Can confirm,” I said before finishing my current beer and cracking open a new one.
“Okay, well if I like how Madison’s fingers feel, then maybe she can try her tongue next,” Alyssa said.
“Man, I really hope you like how my fingers feel,” Madison giggled.
“Oh, she definitely will,” Ashley grinned.
“I’m excited to try it,” Alyssa admitted. “Ashley, you’ve really made it sound good.”
“It is good,” Ashley said. She had just finished her glass of wine and was pouring herself another. We were all beyond tipsy at this point, I think.
“What’s your favorite position?” Alyssa asked. “You can answer too, Brian.”
“For anal?” Ashley asked.
“Hmm,” I said, thinking to myself about the various choices. Doggystyle was an obvious choice, but reverse cowgirl is also pretty great. Even spread-eagle works pretty well with a pillow under Ashley’s butt, and the view there is awesome too, with her tits bouncing as she gets fucked…
“Oh, that’s a tough one,” Ashley said, also pausing to think for a second.
“I hope you’re ready for a thorough answer, Alyssa,” Madison laughed.
“That’s what I want,” Alyssa grinned. Clearly she was getting a kick out of this. “Don’t hold back.”
“Don’t worry,” Ashley laughed. “You know I’d never do that. Especially not with all this wine in me.”
“I think I know my answer,” I said finally. “But I want to hear Ashley’s first.”
“Okay, I’ll go first then,” Ashley said. “Honestly, I know it’s the obvious choice, but I’ve got to go with doggystyle.”
“How come?” Madison asked. I briefly wondered if it occurred to anybody else how wild it was that Madison was asking her big sister why doggystyle was her favorite position for being fucked in the ass.
“It’s mostly for the same reasons that I like doggystyle for regular sex,” Ashley said. “For one, I just love being on my hands and knees with the guy behind me. It just feels sexy, y’know?”
“Despite having a girlfriend, I actually do know what you mean,” Madison laughed.
“It’s not like you didn’t enjoy your fair share of dick before me,” Alyssa shrugged.
Ashley giggled. “And it’s just hot knowing he can see everything back there too. Like Brian has such an incredible view of my ass.”
“That I do,” I grinned.
“He’s got a great view of my pussy and, more importantly in this case, my butthole. It’s just all on display, which makes me feel hot and dirty. He can see it all.”
“Makes sense,” Alyssa said. “I’ve got to imagine a view of you on your hands and knees is hard to beat, especially if you’re naked.”
“Plus, I love having my hair pulled when I’m being fucked,” Ashley continued. I knew she was horny because she was starting to speak more explicitly. I noticed Madison and Alyssa both blush when Ashley said that last part too. They were definitely into it. Ashley was doing a good job of painting them a mental image of what it looked like when I fucked her from behind.
“Especially when Brian really gets going,” Ashley said. “If he’s got a good grip on my hair while he’s pounding me, it just feels so damn good.”
“Goddamn,” Alyssa said under her breath. She was blushing, but clearly extremely turned on by Ashley’s response. Madison was too, for that matter.
“And when Brian grabs my hips while he’s fucking me — or when he grabs my ass — and when he spanks me,” Ashley sighed. “Ugh, it’s just so damn good. I love when my ass cheeks are all red and stinging by the time we’re finished.”
“Fuck yeah,” Madison said. “Nothing better than being spanked when a guy is fucking you from behind.”
“It’s so hot,” Alyssa agreed. “I also like it when the guy reaches forward to squeeze my tits too,” Alyssa said. “Especially if he pinches my nipples or something like that.”
“Ooh yeah,” Madison said. “I feel like that’d always make his dick go super deep.”
“Yessss,” Ashley said. “Exactly, I love that shit. I love feeling the guy’s body slam into me, like when he’s fucking me with deep strokes.”
“Me too,” Alyssa said. “It just feels amazing.”
“Yeah, I was gonna say doggystyle was my favorite for the same reasons,” I said. “But especially because of the view.”
“Mhm,” Ashley said. “You actually get to see your dick, like, fucking me. That’s my only real complaint. I can’t see your dick going inside me when I’m on my hands and knees like that.”
“Exactly,” I grinned. “I love watching it disappear inside you.”
“Yeah, that’s why I liked having sex on my back,” Madison said. “I could actually kind of see the guy’s dick going inside me. I always thought that was hot.”
“Okay, so then Brian,” Alyssa started. “Which has the better view: doggystyle during anal or doggystyle during regular sex?”
“She’s asking if it looks hotter to watch your cock go in my ass or in my pussy?” Ashley said.
“Yes, that,” Alyssa laughed.
I thought for a moment. “Man, that’s a tough one.”
“It really is,” Ashley said. “I don’t even know which one I like better.”
“I feel like seeing my dick buried in your ass is basically impossible to beat,” I said. “But I also like how your asshole looks without my dick in it, y’know? And I only get to see that during regular sex.”
“Awh,” Ashley giggled. “I actually do think my asshole looks nice. Thanks babe.”
Madison laughed, “true love!”
“Heh, so yeah, I really don’t know. I don’t think I can pick one,” I shrugged.
“Honestly, that’s fair,” Alyssa said.
I was obviously rock-hard at this point. Listening to Ashley talk so explicitly about how she liked to be fucked was driving me insane. And, as Madison would tell me later, it was also driving both her and Alyssa crazy too.
“Alcohol makes me so horny,” Ashley laughed softly and shook her head. “Like I am just craving sex right now.”
Madison giggled. “To be fair, you are always horny like that, Ashley.”
Ashley rolled her eyes. “You always say that! Sure, I’m always horny. But alcohol makes me especially horny.”
“Honestly me too,” Alyssa and I said at the same time. We made eye contact and she smiled at me. “I’d be lying if I said I wasn’t thinking about having this one’s head between my thighs right now,” she said, gesturing towards Madison.
“Likewise,” Madison said, flashing her girlfriend a smile.
“What about you, Brian?” Alyssa asked with a drunk smile on her face. “Are you as horny as the rest of us?”
I laughed. “Girl, I’ve been hard this entire time.”
All of the girls giggled at that. “I suppose most guys would be rock hard listening to us talk about getting fucked in the ass,” Madison said.
“Duh,” Ashley said. “It takes a lot less than that to make a guy hard.”
“Very true,” I said. “If you brush my hand as you walk past me in the hallway, I basically have no choice but to go rub one out in the bathroom.”
Madison giggled. “Is that why you disappeared for like an hour when I bumped into you in the hallway the other day?”
I thought for a moment. “Y’know, I think I might’ve actually been jacking off after that happened.”
Ashley and Alyssa both laughed.
“Jesus Christ,” Madison said, joining them in laughing while also shaking her head.
“Nah I’m kidding,” I chuckled. “I mean, it’s possible, but I actually just don’t remember right now.”
“Mhm, sure Brian,” Madison said, smiling.
“Okay y’all,” Ashley said. “I have an idea. Just hear me out.”
“What is it?” Alyssa asked.
“To put it bluntly, it’s abundantly clear that we are all way too horny to focus on anything right now,” Ashley said, laughing a bit as she spoke. Even with her mind clouded by alcohol and arousal, she knew she was about to propose something a little out-there.
“Clearly,” Alyssa laughed.
“Yeah, I’d say that’s an apt observation, babe,” I grinned.
“So I am proposing that each couple briefly retreat to their respective bedrooms…,” she paused for a moment. “Just long enough to relieve themselves. Then we can come back here and continue from where we left off.”
Madison, Alyssa, and I exchanged glances. It appeared that everybody was on-board with Ashley’s proposal.
“A short break couldn’t hurt,” Madison said with only the tiniest reservation in her voice.
“Yeah,” Alyssa shrugged. “Just a few minutes. No big deal.”
“I’m not opposed either,” I said.
Madison chucked. “I am admittedly a little ashamed to require such a break after talking about sex for not even that long, but I mostly just blame Ashley.”
“Me too,” Alyssa said. “I blame Ashley for making us all horny.”
“Awh shucks,” Ashley said. “That means so much, thanks guys.”
I laughed. Of course it’s Ashley’s goal in life to make her friends (and her little sister, apparently) horny.
“Okay, so let’s go then?” Ashley said.
“Yep,” Madison said. She and Alyssa got up and giggled to themselves as they walked back towards their room.
Ashley and I followed behind them until we reached Ashley’s door. Ashley opened the door and I started to walk in, but stopped and looked back once I saw that she was waiting at the door. Ashley held up a finger.
“I didn’t hear them close their door,” Ashley whispered to me.
“Meaning what?” I asked.
“Maybe they want us to hear them having sex,” Ashley whispered back. “And maybe they want to hear you and I having sex.”
I shrugged. “Probably.” I mean, obviously Madison would love it if we overhead her and Alyssa banging, and we all know how Madison feels about Ashley and I. I just wasn’t as aware of the whole closed/open door situation as Ashley.
“We did joke about forgetting to close our door earlier,” I mused out loud.
“Exactly,” Ashley said.
“What about your parents?” I asked. “Will they hear us if we try to put on a show with our door open?”
“What? No,” Ashley said. “You’re seriously concerned about that now? How many times have we had loud-ass sex down here?”
“Good point,” I shrugged. “I guess they are two floors above us.”
“And they sleep like rocks,” Ashley said. “And they went to bed at least an hour ago, so we’re definitely fine to be as loud as we want.”
“Great,” I grinned.
Ashley stood for a moment longer before shrugging. She started to walk towards me, leaving the door open of course, before stopping quickly. She turned her head slightly and listened.
“I can hear moaning,” Ashley whispered quickly. “They definitely didn’t close their door.”
I got up and tip-toed towards the door, peaking my head out to listen. Ashley was right. I could definitely hear Madison moaning. She wasn’t being very loud (yet), but it wasn’t muffled (as if I was hearing it through a door).
“Yeah, they definitely left their door open,” I whispered.
“Awesome,” Ashley grinned. With that, she dropped her pants and her panties and hopped up onto her bed. She got on her hands and knees and turned to face me, meaning her face was towards her open door.
“C’mere and fuck me already,” she grinned.
I dropped my pants and boxers and walked over to Ashley. She brought her head down and took my mostly-hard cock into her mouth, sucking it gently before moving down to take my balls into her mouth. She pumped my cock with her hand for a second as she ran her tongue around my balls. Once I was completely hard, she let my balls fall out of her mouth, gave my cock a couple more strokes for good measure, and then released it.
I walked to the left and hopped up on the bed behind her. Immediately I was greeted with a gorgeous view of Ashley’s ass. Her pussy was already wet — she wasn’t lying about being horny. I took an ass cheek in each hand and squeezed, enjoying the view of her pussy and her asshole for a moment before releasing her right cheek. I grabbed my cock and aligned it with her pussy. Slowly, I thrust forward, and the two of us moaned as the head of my cock slid inside her.
I continued to firmly grab her ass with my left hand. With my right, I braced against her lower back and slid the rest of my cock inside her. I held it there once I bottomed out inside her, enjoying the familiar feeling of being balls-deep in my girlfriend. Ashley whimpered. Slowly, carefully, I began to slide my cock in and out of her pussy. I gave her right ass cheek a firm slap and began to fuck her harder. Ashley moaned audibly.
With that, I grabbed both of her hips and began to fuck her hard and fast. I pounded her tight, wet pussy, fucking her with deep strokes. She made absolutely no effort to contain herself.
“Oh my God,” she groaned loudly. “Fuck yes, fuck my pussy, Brian.”
“Good girl,” I groaned. “Take my cock, that’s right baby.”
There was no doubt that Ashley’s moans could be heard by anybody in the basement. Hell, if anybody happened to be upstairs right now, then they would almost certainly be able to hear her moans too.
“Fuck yes, daddy,” Ashley cried. “Fuck my tight little pussy. Fuck me, fuck me, oh my God, yes!”
I spanked her ass again, this time hard enough to leave a bit of a mark.
“Fuck, spank me again,” Ashley cried. I gave her another spank, this time on the other cheek.
Even in my drunk state, I didn’t have too much left in me. Knowing Madison and Alyssa were surely getting off to the sounds of Ashley and I fucking was making it hard to last. And to make matters worse, it was at this point that I heard Alyssa’s voice cry out, “Fuck Madison, don’t stop, you’re gonna make me cum!”
“Holy shit,” Ashley and I both said, in between moans. Ashley kept up her moaning, but we both listened as Madison made Alyssa cum.
“Fuck, fuck, fuck,” we heard Alyssa cry out. “Fuck, I’m coming. Don’t stop, I’m coming!”
Ashley started rubbing her clit as I pounded her pussy. I slowed down briefly to stave off my own orgasm. She moaned softly, for once regulating her volume so she and I could enjoy the sounds of Alyssa’s orgasm.
“Just keep going just like that baby,” Ashley cooed. “I can cum from this.” Thank God, if I fucked her any faster, it’d be game over.
Ashley worked her clit as she enjoyed the feeling of my cock pounding her pussy. Her moans filled our room again as Alyssa began working on Madison in the other room.
“Oh fuck,” I heard Madison cry out. “Fuck baby, oh my God, eat my pussy just like that.”
“Fuck,” I grunted. “I don’t have much left in me here, babe.”
“That’s fine,” Ashley groaned. “I’m gonna come.”
I felt Ashley’s body tense up. “Fuck, fuck, fuck, fuck, FUCK!” Ashley cried out. At this point, I gave up on trying to last. I pounded Ashley’s pussy with everything I had. I dug my hands into her hips and slammed my cock in and out of her as my girlfriend started to climax around my cock, fueled by the sounds of her little sister getting head just down the hall.
“I’m cumming,” Ashley cried. “Fuck yes, I’m coming. Oh my God, fuck!”
“Me too,” I grunted.
“Yes, come with me, baby!” Ashley said. “Fill my pussy with your cum!”
With that, I began to unload a huge load into Ashley’s pussy. The room was filled with the sounds of our moans as the two of us climaxed together. We were very loud; there was no doubt Madison could hear all of this just down the hall.
Ashley’s orgasm finished a few seconds before mine. She whimpered softly as I shot the last of my cum inside her. Once my orgasm finished, I left my cock inside her for a brief moment.
“Do you want tissues?” I asked her.
“No,” Ashley said. “I’m just going to put my panties back on. I want your cum all over my pussy.”
“Did this even help your horiness at all?” I laughed.
“What do you think?” she looked back at me, grinning.
“I think not,” I chuckled.
I quickly pulled out of Ashley. She jumped up and slid her panties, followed by her pants, back on before any of my cum could leak out of her pussy.
She and I quietly returned back to where we were sitting, topping off our drinks and enjoying the sounds of Alyssa giving Madison head down the hall. We were only sitting there for maybe twenty seconds before we heard Madison cry out that she was about to cum. Immediately I felt myself get hard again as I listened to Madison ride out her orgasm, unabashedly sharing her pleasure with us with the sounds of her moaning. I glanced at Ashley, who was biting her lip, clearly loving every second of this.
Ashley and I sat and listened to her little sister ride out her orgasm. Once Madison finished coming, Ashley spoke.
“That was so hot,” she said quietly.
“Do you think they’ll be embarrassed?” I asked.
“Mmm, maybe,” Ashley said. “Not Madison, obviously. But maybe Alyssa.”
“Yeah,” I said. “But they’re still drunk, so probably not.”
“I agree,” Ashley said.
We sat and waited. After about two minutes, Madison came around the corner, followed by Alyssa.
“I think you guys forgot to close your door,” Ashley grinned.
“You guys too,” Madison said, returning her smile.
“But it did sound like y’all had a good time,” Ashley said. “Feel any better?”
“Oh, it was great,” Madison said. “But…”
“Still horny?” Ashley asked.
“Very,” Madison shrugged. “How about you guys?”
“Take a guess,” I said.
Madison laughed. “Why don’t you stand up for me real quick, Brian?”
I rolled my eyes and stood up.
“And now, could you just turn to the side?”
I laughed and did as was asked of me. I could feel all of the girls staring at the very obvious bulge in my pants. (It was already visible from the front, but having me turn to the side removed any ambiguity.)
“Okay, you’re good,” Madison smiled.
I sat back down.
“So it goes without saying that Brian is still feeling a touch hot and bothered,” Ashley laughed.
“And, if I had to guess, I imagine you’re feeling the same,” Madison giggled.
“Mhm,” Ashley shrugged. “What about you, Alyssa?”
Alyssa blushed as she sat down. “Madison gave me one hell of an orgasm,” she started. “Buuut I’m gonna need a few more before we call it a night.”
“You and I both,” Ashley laughed. “But from the sounds of it, everybody had an orgasm just now, right?”
“I sure did,” Madison said. “And mine may or may not have been fueled by the sound of Ashley’s orgasm.”
Ashley smiled at her sister.
“What about Brian?” Alyssa grinned at me.
“Oh, Ashley can answer that one,” I said.
Ashley shrugged. “This cum in my pussy had to come from somewhere.” Alyssa blushed pretty hard at that one. Madison just bit her lip.
“He came inside you?” Alyssa asked. She took a big sip of her wine, as did Madison.
“Mhm,” Ashley grinned. “I’m a lucky girl.”
“No kidding,” Alyssa said softly.
“But what did you guys do?” Ashley asked.
“Nothing fancy,” Madison grinned.
“Yeah,” Alyssa said. “We just made out for a tiny little bit and then gave each other head.”
“Sounds like a good time to me,” Ashley said with a smile.
“Agreed,” I said.
“What about you guys?” Alyssa asked.
“Oh, I just hopped up onto my bed and got on my hands and knees.”
“Doggystyle, eh?” Madison said.
“Mhm,” Ashley grinned. “Brian got behind me and pounded me pretty good.”
“Now that also sounds like a good time,” Alyssa said, blushing.
“That it does,” Madison said.
“It was great,” Ashley said. “My favorite part was getting filled up at the end there..”
“I bet it was,” Alyssa said slowly, clearly thinking about what it’d be like to have been filled up by me, just like Ashley. I was already super hard again.
“In any case,” Ashley grinned. “I think my ass is next.”
“What do you mean?” I asked.
“I think she wants you to put it in her butt, Brian,” Alyssa giggled.
“Duh,” Madison said. “But not just that. She’s talking about having Brian cum inside her ass.”
“Yes,” Ashley laughed. “That. That’s what I want next.”
“Damn,” Alyssa said. “Both holes in one night? Y’all are wild.”
I shrugged. “Sounds good to me.”
Madison laughed. “I bet it does.”
“Speaking of butts,” Ashley said. “You didn’t happen to sneak a finger or two in Alyssa’s just now, did you Madison?”
“No,” Madison giggled. “I certainly thought about it though.”
“Honestly, if you had asked, I probably would’ve said ‘yes’,” Alyssa said. “I was too horny to refuse.”
“What if she asked you right now?” Ashley grinned.
“Asked what?” Alyssa asked. “If she could put her finger in my ass?”
“Yes,” Ashley replied.
Alyssa shrugged. “I’m still really horny so…” She took another big sip of her wine, as did Ashley. I was almost done with my beer.
Ashley looked at Madison. “Well?”
Madison turned and looked at Alyssa. “Can I put my finger in your ass?” The two of them started laughing.
“But like, right now?” Alyssa asked, glancing around at the rest of us.
“Why not?” Ashley shrugged. “Brian and I can help make sure everything goes smoothly.”
“That we can,” I said.
“Where would we do it? Like literally right here?” Alyssa asked.
“Sure,” Ashley said. “If that works for you, that is.”
“I guess so,” Alyssa said. “But, like, are we really going to do this?”
“I’m down,” Madison grinned. “I know Ashley’s down. And Brian would never say ‘no’ to a show like this.”
“Damn right,” I laughed.
“Okay,” Alyssa said. “Jesus Christ. Whatever. I’m drunk. I’m horny. Let’s do it.”
“That’s the spirit,” Ashley laughed. She stood up and stumbled toward her room, “I’ll be right back.” She returned a few seconds later with a towel and a bottle of lube.
“Here,” Ashley said, handing the towel to Alyssa. “Sit on this.” Then she handed Madison the bottle of lube.
“Should I just take my pants off?” Alyssa asked.
“Probably,” Ashley said. “That would be easiest.”
“Okay,” Alyssa said hesitantly. She stood up and hooked her thumbs into the waistband of her running shorts. I noticed for the first time that she was no longer wearing a bra under her tank top, and her nipples were clearly hard and poking through the fabric of her top.
Alyssa took a noticeable breath before dropping her pants down to her ankles, skipping them off of her feet. She was wearing a black, lacey thong underneath.
“Goddamn girl,” Ashley said, taking in the view. “You’re so hot!”
“Isn’t that thong so cute?” Madison asked.
“Very,” I grinned.
“Here, I’ll join you in solidarity,” Ashley said. She quickly stood up and stripped off her pants, revealing her own black thong underneath.
“I guess I will too,” Madison said. With that, she stood up and pulled her pants down. She was also wearing a thong, but hers was red.
“Holy shit,” Madison said, staring at Ashley’s crotch.
“What?” Ashley said, looking down. “Can you see Brian’s cum?”
“Mhm,” Madison said. Indeed, Ashley’s thong was pretty clearly wet with my cum.
“Holy shit,” Alyssa said. “That’s hot.”
“Very,” Madison said.
Alyssa started to sit back down, but paused when Madison said, “wait!”
“You should give ‘em a twirl,” Madison grinned.
“Oh, you’re right,” Alyssa blushed. “How impolite of me not to show you guys my ass.”
“We forgive you,” I chuckled. .
“As long as you show off a bit, that is,” Ashley added.
Alyssa gigged. She turned around so that her back was facing us, and we were greeted by a beautiful view of her ass. Evidently she was wearing a G-string specifically, as her underwear disappeared completely between her buttcheeks.
“Bend over a bit,” I suggested.
Alyssa blushed and bent forward, bracing her arms against the back of the couch. Her efforts were rewarded with enthusiastic reactions from Madison, Ashley, and I.
“Hot damn,” Ashley said, breathing in sharply. “You’ve got such a nice ass, Alyssa.”
“Holy shit,” I said. “You’re so hot!”
When Alyssa bent over, we all got a much better view of what all was going on between her cheeks. Her thong was pretty skimpy; it just barely covered her asshole. In fact, you could see her part of her asshole on either side of the thong. And her pussy was barely contained; the thin strip of fabric didn’t leave too much to the imagination. You could see her lips on either side.
“You should spread your cheeks for them, baby,” Madison said, winking at us.
Alyssa was still very much red-faced, but she did as she was told. Struggling a little bit in her drunken state to maintain her balance, she reached back and grabbed ahold of her buttcheeks with her hands. Slowly, she spread them apart. Immediately it became obvious how wet her pussy was.
“Ho-ly fuck,” Ashley said. “Oh my God.”
“Fuck yeah,” I said.
When she was standing normally, we could just see the wrinkles of her asshole on either side of the thong. But when she spread her cheeks, the three of us got a proper look at.. It wasn’t fully exposed, as her thong still covered it slightly, but we could actually see her asshole pretty clearly. And beneath that, we got a great look at her pretty pink pussy. Man, I wanted nothing more than to bury my cock in either one of those holes right then and there. They both looked so inviting, and I bet fucking her would’ve felt amazing.
In any case, Alyssa let us enjoy the view of her pussy and her asshole for another few seconds before turning around. “Wow, okay, that was a lot.”
“You’re so fucking hot,” Ashley said.
“Agreed,” I said. “You’re so sexy.”
Alyssa spread the towel out on the couch and sat down. “Thanks guys,” she said. “How should I sit?”
“Like this,” Ashley said. She turned to the side and laid back, propping her head up against the corner of the sofa and the armrest so that she could still see everybody. She brought her legs up, bending them at the knee, and spread them apart so that she was effectively spread-eagle. We all had an incredibly erotic view of her crotch, which was just barely covered by her thong.
“Now y’all can really see what’s going on between my legs,” Ashley said, playfully stroking the crotch of her panties. “Except in your case, I might stick a pillow under your butt. That’ll make it much easier to maneuver around down there.”
“I am loving this view of you, Ashley,” Alyssa cooed. She was very-clearly staring at Ashley’s lips peeking out on either side of her thong.
“Me too,” Madison said. “I can almost see your butthole!”
Alyssa giggled. “Yeah, your thong isn’t leaving much to the imagination.”
“Just how I like it,” Ashley grinned.
“I’d like it if your thong wasn’t in the way,” Madison complained.
“I bet you would,” Ashley smiled and sat back up. I was surprised she didn’t pull her thong to the side to give Madison a quick peek at her butthole, as Madison was clearly interested. But I guess Ashley was just focused on getting something in Alyssa’s ass rather than showing off her own body for once.
“Could you hand me that pillow there, Madison?” Alyssa asked.
“Yeah,” Madison said, grabbing the pillow and handing it to Alyssa.
Alyssa stood up and lifted the towel before sliding the pillow underneath it. She sat back down and laid back as Ashley had instructed: she leaned back so that she could rest her head in the corner of the armrest and the back of the couch. Her butt was on top of the pillow so when she brought her legs up and spread them, her crotch was sort of elevated. Ashley was right, everything would be much easier to access with a pillow under Alyssa’s butt.
Alyssa sat there with her legs spread wide open while Ashley, Madison, and I admired the view. Much like Ashley, Alyssa’s thong did not leave much to the imagination either. We could see her pussy lips peeking out on either side of the thong, and her asshole was hardly covered at all in this position.
“Oh wow,” Madison said. “Your butthole is more visible than Ashley’s was!”
“Lucky us,” Ashley laughed.
“Oh God,” Alyssa said, blushing.
I laughed. “Isn’t that the whole point?” I asked.
“Yeah, but it’s still kind of a lot that you guys can see my butthole.”
“I’m certainly not complaining,” Ashley shrugged, still looking unabashedly at the lovely view between Alyssa’s thighs. “Actually, I am complaining because I can’t see everything with your thong in the way!”
Madison laughed. “Yeah babe, I think it’s about time you showed us the goods.”
“Agreed,” I said. “Your panties have gotta come off.”
“Jesus,” Alyssa said. She sighed and brought her legs together. She hooked her thumbs into her panties and began to slowly pull them down.
“Ho-ly fuck,” I said under my breath. Alyssa’s pussy slowly came into view. She had her legs pressed together, meaning her pussy lips were pressed up against each other. She looked incredibly tight. Immediately I thought again about how good it’d feel to slide my painfully-hard cock inside her right then and there. I honestly doubt anybody would have complained, especially not Alyssa. But I just sat there and drank in the view. Below her pussy was our target, her asshole, which honestly looked equally inviting.
“My God,” Ashley said. “Your pussy looks so fucking good.”
“So does your ass,” I said.
“Agreed,” Madison said. “You’re so hot, baby.”
“Thanks guys,” Alyssa said, still clearly embarrassed to have everything out on display. Despite this, however, she tossed her panties onto the ground and spread her legs again. The view was absolutely incredible. I wanted to fuck her so badly, as did Ashley and Madison, I’m sure.
“Okay,” Ashley said. “You ready?”
“I think so,” Alyssa breathed. “I’m the weirdest combination of drunk, horny, and embarrassed right now.”
“Sounds like the perfect combination for your first experience with butt stuff!” Madison giggled.
“Alright,” Ashley said. “Madison, go ahead and squirt some lube on her ass.”
Madison nodded and uncapped the bottle of lube. She moved closer to Alyssa and held the bottle over her ass. Slowly, Madison squeezed a big drop of lube onto Alyssa’s asshole.
“Eep!” Alyssa said. “It’s cold!”
“Sorry,” Madison said. “Too cold?”
“No, no,” Alyssa said. “It just surprised me.”
Madison capped the lube and began to slowly massage the lube around Alyssa’s asshole.
“Oh wow,” Alyssa said. “That actually feels really good. Surprisingly.”
“That’s a good sign,” Ashley grinned. I noticed Ashley had her hand between her legs and was very slowly rubbing her clit over her panties. I don’t think Alyssa or Madison noticed though.
Madison positioned herself so that she was basically on her hands and knees, though she was leaning her body against the back of the couch a bit so as to give us as good a view as possible of the action between Alyssa’s legs. And we had a pretty good view. Ashley and I were enjoying a gorgeous look at Alyssa’s pretty, pink pussy and below that, her tight little asshole.
“Alright, I’m gonna start putting my finger inside, okay?” Madison said.
“Mhm,” Alyssa said. She took a deep breath as Madison pressed her finger against Alyssa’s asshole. Madison only had to press for a second before the tip of her finger slipped inside.
“Oh shit,” Alyssa said. She had a weird look on her face. This was definitely her first time experimenting with putting something in her ass. She closed her eyes, maybe trying to focus on how she was feeling.
“How’s that?” Madison asked. She was holding the tip of her finger inside Alyssa’s butt. She was only maybe one knuckle deep at this point.
“Weird,” Alyssa said. “But not bad. Just… very weird. You can do a little more.”
Madison nodded and pressed her finger in a bit more. She stopped once she was two knuckles deep.
“Can you guys see okay, by the way?” Madison looked back, grinning.
“Oh yeah,” I said. I had a great view. I could see Alyssa’s pretty pink pussy and Madison’s finger halfway inside Alyssa’s ass.
“I’m good too,” Ashley said.
Madison noticed that Ashley was masturbating. She smiled and watched Ashley touch herself for a brief second before returning her attention back to Alyssa.
“How are you doin’, baby?” Madison asked.
“Good,” Alyssa said. “Can you do your whole finger now?”
“Sure,” Madison said.
Ashley and I watched lustfully as Madison slid the remainder of her finger to Alyssa’s ass.
“How does that feel?” Madison asked.
“Really nice,” Alyssa cooed. She reached down and began to rub her clit. “Do you want to start fingering me?”
“Like in and out?”
“Fuck yeah,” Madison grinned. She slowly slid her finger out of Alyssa’s ass until it was just one knuckle deep. I glanced over and saw that Ashley’s hand had moved inside her panties. I thought about jerking off, but I decided to hold off for the time being.
Alyssa moaned softly as Madison pressed her finger all the way back inside her ass. She continued toying with her clit as Madison began to finger her, maintaining a slow and steady rhythm. Alyssa was still laid back on the couch in front of us, legs spread wide open. She had her head back now, and her eyes were still closed. She was definitely focused on enjoying the feeling of Madison’s finger sliding in and out of her ass.
I glanced over at Madison and realized that we actually had a great view of Madison’s ass too; I had just been so focused on Alyssa that I hadn’t realized it. Like I said, Madison was on her hands and knees, which is already a sight to behold. But she was also wearing that skimpy little thong, which made her look even more sexy. Her pussy lips were just barely covered, and I could see most of her asshole behind the fabric. I couldn’t believe I had just spent a good part of the evening fucking that tight little asshole of hers. In fact, some of my cum was presumably still inside her.
“Madison,” Ashley whispered quietly. I don’t think she wanted Alyssa to hear, but that was bold given Alyssa and Madison were basically equally far away from where Ashley and I were sitting.
That being said, it seemed like Alyssa was too focused on having her ass fingered for the first time to notice. Either that, or she didn’t react if she heard Ashley. But Madison heard Ashley, so she slowly turned her head and looked back.
Ashley pointed at Madison’s butt, then reached down and pulled her own thong to the side for a second, flashing her pussy at Madison. Then Ashley gestured towards Madison’s butt again.
Madison furrowed her brow for a second, clearly confused, until it clicked for her. Madison turned back towards Alyssa. She reached back with her free hand and pulled her thong to the side. She positioned it so that it was now stretched across one of her ass cheeks, giving us a completely unobstructed view of her pussy and her asshole.
I looked at Ashley and nodded approvingly. She gave me a wink before turning back to enjoy the view, continuing to masturbate, obviously. I focused my attention on Madison for a moment. I swear, I will never get tired of looking at that girl’s bare ass when she’s on her hands and knees. Her pussy looked so good; she was incredibly wet, and I’m sure it would’ve felt incredible to slide my cock inside her. And above her pussy, of course, was that tight little asshole that I fucked earlier this evening. It honestly required a bit of self control to stop myself from getting up and walking over to fuck Madison’s brains out right then and there.
“Baby,” Alyssa said softly. “I think I want a second finger in my ass.”
“You got it,” Madison said. She reached for the lube, uncapped it, and squirted some more around the finger that was already embedded in Alyssa’s ass. She capped the lube, placing it back down beside her.
“Ready?” Madison asked.
“Mhm,” Alyssa cooed.
Slowly, Madison pressed her middle finger up against Alyssa’s anus. With only a little bit of effort, Madison was able to push her middle finger inside Alyssa’s ass.
“Oh fuck,” Alyssa groaned, pausing her masturbating for a moment as she adjusted to having two fingers in her ass.
“Are you okay? Does it hurt?” Madison asked.
“No, no,” Alyssa said. “It’s just more intense than I expected. But I like it.”
Madison held her fingers in Alyssa’s ass just as they were for another moment. She had both fingers about one-and-a-half knuckles in right now.
“Okay,” Alyssa breathed. “I think I’m good. Can you slide your fingers all the way inside me now?”
Madison didn’t say anything. Instead, she just pressed her two fingers all the way into Alyssa’s ass.
“Mmm,” Alyssa moaned. “Fuck, that feels good.”
“Should I start finger-fucking you again?” Madison asked.
“Yes, please,” Alyssa said softly.
With that, Alyssa began rubbing her clit again, and Madison began sliding her two fingers in and out of her girlfriend’s ass.
“Oh shit,” Alyssa gasped. “That feels so fucking good.”
“Right??” Madison laughed. “I knew you’d like having your ass played with.”
“You were so right,” Alyssa said. “Fuck me, that’s amazing. Don’t stop!”
Madison continued finger-fucking Alyssa’s ass, which was gripping her fingers tightly. Alyssa’s fingers were a blur on her clit at this point; clearly, she was working her way towards a big orgasm.
I watched as Alyssa instantly became lost in the pleasure of having something in her ass. She rubbed her clit faster and faster as Madison continued finger-fucking her tight little hole. I couldn’t believe I was seeing this. Never did I think I’d have a front-row seat to Madison finger-fucking Alyssa’s ass.
“Fuck, fuck, fuck!” Alyssa gasped. “You can fuck me harder, baby. Finger my ass harder!”
Madison bit her lip and began sliding her fingers in and out of Alyssa’s ass even faster. Alyssa began to moan loudly. Her back was arched, and her toes started to curl. That girl was quickly falling in love with anal. I was surprised. Even Ashley took a little bit of time to warm up to having her asshole played with. But Alyssa was taking a pretty-good fucking from two fingers, despite having never put anything in her ass before tonight.
“I’m gonna come,” Alyssa cried. “Fuck, I’m gonna fucking come!”
“Good lord,” I said under my breath.
“Come for me, baby girl,” Madison cooed. “Come for me, nice and hard.”
Alyssa gasped for breath and arched her back hard. She was rubbing her clit in little circles while Madison finger-fucked her asshole. Ashley and I watched, both of us unbearably horny, as Alyssa enjoyed her first (of many!) orgasms with something in her ass.
Alyssa sighed heavily as her orgasm subsided. Madison slid her fingers out of Alyssa’s ass gently. She got up and went to the bathroom to wash her hands while Alyssa caught her breath.
“So,” Ashley began. “What did you think?”
“That was incredible,” Alyssa breathed. “My orgasm felt amazing. It was so intense.”
“That’s awesome,” I grinned. “But I’m a little surprised that all three of you girls apparently like anal. And I’m shocked you came around to it so quickly, Alyssa.”
“I’m not,” Ashley shrugged. “What’s not to like? It’s hot. It feels great.”
“Girl, even you took longer than that to start liking anal,” I grinned.
“Fair,” Ashley said. “But Alyssa had a room full of experts making sure her first experience with something in her ass was a good one!”
“You know what,” I said, laughing. “You make a good point.”
“I personally just can’t believe we did that,” Alyssa giggled. “Madison really fingered my ass while you guys watched.”
“Well, I didn’t just watch,” Ashley said. “I was totally touching myself that whole time.”
“Oh my God, really?” Alyssa asked, looking up.
“Mhm,” Ashley said. “I haven’t really stopped.” Indeed, Ashley’s hand was still in her panties, and she was clearly still rubbing her clit, albeit fairly slowly.
“You wanna take your panties off?” Alyssa asked. “I’m the only girl sitting here with her pussy out right now.”
“Actually, I pulled my panties down already,” Madison said. She stood up and kicked them off of her feet.
Ashley followed suit. She brought her legs together and quickly pulled her panties off, kicking them down onto the ground. She leaned back a bit and spread her legs so that Alyssa had a good view of her pussy. “Is that better?”
“Much better,” Alyssa said, looking greedily at Ashley’s pussy.
Madison came back from the bathroom and immediately noticed that Ashley was no longer wearing her panties.
“Nice pussy, sis,” Madison giggled.
“Thanks!” Ashley smiled.
Madison sat down on the couch next to Alyssa and spread her legs so the rest of us could get a good look between her thighs.
“Damn,” Ashley said. “I guess having bomb-ass pussies runs in the family.”
Alyssa laughed. “Apparently.”
“Well shit,” I said. “I’m the only one here still wearing underwear”
Ashley laughed, as did Madison.
“That’s a good point,” Alyssa said, biting her lip. “Y’know, I’ve heard an awful lot about that cock of yours, but I’ve never actually gotten a good look at it.”
“Hey, yeah,” Madison said. “Ashley always talks about how much she likes your dick. I think it’s about time we see it.” Okay, Madison. It’s not like you just spent part of the evening having your ass fucked by me and my friend. And we fucked your mouth too, for that matter!
Ashley grinned. “Well Brian?”
Man, I was lucky this was not my first rodeo. Otherwise this big reveal would’ve likely been a bit disappointing for these three ladies. But I was long past being nervous in this type of scenario.
“Alright,” I shrugged. “But if you guys want to see it so badly, why don’t you come over here so you can get a closer look?”
Alyssa and Madison glanced at each other before standing up and walking over. Both girls had a thin strip of hair above their pussies; they looked very sexy walking over here without any panties. Evidently both girls had foregone their bras, judging by how clearly their nipples were poking through their tops. I could even see Madison’s areolas faintly through the fabric of her tank top.
I spread my legs wide, and the two girls got down on their knees in front of me. I was obviously still rock hard given I just watched Alyssa enjoy her first anal encounter, so I was ready to go. I glanced at Madison and gave her a look as I lifted myself up off the seat a bit. She took the hint and grabbed my pants and boxers, gently pulling them down. She brought them down to my ankles, and my cock sprang up, pointing straight towards the ceiling.
“Oh my,” Alyssa managed. Ashley bit her lip and watched her little sister — and her little sister’s girlfriend — take in the sight of my rock-hard cock.
Alyssa stared at it fairly wide-eyed with a mixture of shock, bewilderment, and arousal painted across her face. It had clearly been a little while since she was eye-level with a hard dick. Madison, on the other hand, stared at my cock with only lust in her eyes. She slowly traced her hand up my right thigh, stopping just before touching my cock. Alyssa did the same.
“Can I–”, Alyssa said, turning to look at Ashley. “Can we…?”
“I’d be offended if you didn’t,” Ashley grinned. She was openly masturbating again. One hand was working her clit while she had two fingers from the other buried in her pussy. Alyssa and Madison would both have likely been fixated on that display if it weren’t for the fact that they were eye level with my erection.
I moaned softly as Alyssa wrapped her fingers around the base of my shaft. She just held my cock in her hand like that for a moment, squeezing it softly, enjoying how it felt in her hand. Madison immediately cupped my balls and began to massage them gently. She already knew what I liked.
“Wow,” Alyssa said. She slowly traced her hand up my shaft, stroking my cock gently while Madison continued working my balls. Alyssa traced her thumb around the head, feeling the ridge against her fingers. “You weren’t lying, Ashley.”
“Yeah. You’re a lucky lady, sis,,” Madison giggled.
“Very lucky,” Alyssa said softly. “You get to play with this thing every night?”
“You’re goddamn right I do,” Ashley said proudly.
“You get fucked by this thing every night?” Alyssa said softly.
“Mhm,” Ashley grinned. “Why do you think I make so much noise when Brian fucks me?”
Alyssa bit her lip. Clearly that girl was imagining what it’d be like to sink down onto my cock right now.
“Go on,” Madison said. “Stroke his cock for a bit.”
Alyssa bit her lip as she began to slide her hand up and down my cock. I moaned softly.
“Do you guys wanna suck it?” Ashley asked. “It feels really good in your mouth.”
Alyssa looked at Madison, who immediately nodded.
“Yes, please,” Alyssa said.
“Oh, I like that,” Ashley grinned. “Go ahead, since you were so polite. Suck my boyfriend’s cock.”
“Yes, mommy,” Alyssa said softly. I swear, my eyes damn-near bulged out for a second. I had no idea Alyssa would be so submissive! I honestly figured Madison was the submissive one, given how she acts towards me. But I guess it’s sort of like how Ashley is with other girls; Ashley tends to be dominant towards women, but she’s incredibly submissive towards me. In any case, Madison was clearly into this too, which didn’t really surprise me. Something about watching her girlfriend act submissively towards another woman apparently got Madison going.
“You can go first, baby girl,” Madison said.
Madison scooted to the side a bit but continued to rub my balls as Alyssa quickly tied her hair back in a ponytail. (She had been wearing a hair tie on her wrist.). Alyssa sat up on her knees and leaned over, holding the base of my cock firmly with her right hand, bracing herself against my left thigh with her other hand. She lowered her head down onto my cock, and I moaned softly as I felt her lips slowly wrap around the head.
“Fuck,” I sighed. “Good girl.”
Alyssa carefully took about half of my cock into her mouth before stopping. She held still for a moment, enjoying the feeling of having a hard dick in her throat again. Madison gently pressed the back of Alyssa’s head down, forcing her to take in more of my erection into her throat. The room was fairly quiet except for the faint sounds of Alyssa sucking my dick.
“Good, baby,” Madison said softly. “Suck daddy’s cock, just like that.”
Madison looked up at me, almost as if to look for approval. I gave her a nod, and she continued pressing Alyssa’s head down onto my cock. Alyssa moaned softly as she took more and more of me into her mouth. She was nearly at her limit. Her eyes began to water, but Madison held her head down a little longer. Finally, Madison removed her hand from the back of Alyssa’s head, and Alyssa quickly came up off my cock, gasping for hair.
“Holy shit,” she breathed. “Fuck me, wow. Fuck, I love that so much.”
“You like sucking cock?” Madison asked.
“Yes,” Alyssa said, still breathing hard. “Fuck yes, I love having a cock in my mouth. I love it so much.”
With that, Alyssa immediately took me back into her mouth. Madison continued rubbing my balls as she pressed Alyssa’s head back down onto my cock. She f****d as much of me into Alyssa’s throat as she had before, but this time, she allowed Alyssa to come back up off of it immediately.
“Fuck yeah,” I groaned as I watched my cock disappear and then reappear from Alyssa’s lips. Madison bit her lip as she began to force Alyssa to bob her head up and down. Alyssa moaned softly, placing both of her hands on my thighs, and allowed herself to be controlled by Madison.
“Make sure she sucks me good,” I moaned, looking at Madison. She nodded and moved her hand from my balls to Alyssa’s forehead.
“Holy fuck,” Ashley said. Madison began to force Alyssa’s head to bob up and down on my cock. I was essentially fucking Alyssa’s mouth, but Madison was doing all the work.
Alyssa began to gag, and her eyes were watering, but she didn’t stop. I just sat back and enjoyed the blowjob. It felt fucking incredible, especially considering Alyssa hadn’t worked a cock in a long time.. Alyssa was working her tongue around my shaft as best she could while Madison pressed her head up and down.
“Good girl,” Madison cooed softly. Alyssa continued moaning as she was f****d to suck my cock. It was getting incredibly messy too, and the room was filled with wet slurping sounds as Alyssa relinquished her body to be used for my pleasure.
I enjoyed “face-fucking” Alyssa for another minute or so before Madison slowly pressed Alyssa’s head down onto my cock again. This time, she didn’t stop where she did before. Instead, Madison slowly f****d Alyssa to take the entirety of my cock into her throat. Alyssa’s eyes watered and her makeup began to smear as she fought to take all of me into her mouth. Finally, her nose pressed up against my pelvis, and Madison held Alyssa’s head down onto my cock for another good five seconds before letting her girlfriend come up for air.
“You’re not half bad at sucking cock,” Madison mused. “Look at you deep-throating him.”
Alyssa was breathing hard. She had spit all over her mouth, and tears in her eyes. “Thank you,” she said. “I’ve had my fair share of practice. I’m just a little rusty.”
“Feels pretty goddamn good to me,” I grinned.
Madison began tying her hair back. “I think I’ll have a go now.”
Alyssa shifted out of the way.
“Rub my balls,” I told her. “Like Madison was doing earlier..”
“Yes, daddy,” Alyssa said. She reached over and took my balls into her hand, massaging them gently while Madison finished tying her hair back.
Madison shifted into position in the middle of my feet. She sat up straight, grabbed the base of my shaft, which was very wet from the head Alyssa had just given me, and brought her lips to the head of my cock. Slowly, she took me into her mouth, and immediately I let out a moan. Madison twirled her tongue around the head of my cock, teasing the underside of the head for a moment, before continuing to take more of me into her mouth. Unlike Alyssa, she had no problem taking all of me into her mouth. I placed my hand on the back of her head and held her in place once her nose pressed up against my pelvis, and I enjoyed the feeling of having the entirety of my cock buried in the throat of my girlfriend’s little sister. All the while, Ashley was masturbating just a few feet away from me, and Alyssa was gently rubbing my balls.
As if to prove that Madison knew how to suck cock better than Alyssa, I held Madison’s head there for a long time. Her mouth was warm and wet, and her tongue danced around my shaft as my cock stayed buried in her mouth. Finally, I let her come up for hair. She gasped and breathed hard, but she was in much better shape than Alyssa had been, despite holding my cock in her throat for longer.
“Wow,” Alyssa said. “You really know how to suck a cock, baby.”
Madison flashed her a smile before taking my cock back into her mouth. She began to bob her head up and down my shaft, sucking the top half of my cock while she stroked the bottom half with her hand.
I moaned loudly as Madison worked my cock like a pro. She had gotten to be pretty good at sucking me off at this point. I glanced over at Ashley for a moment, who looked like she was in heaven watching her little sister and her little sister’s girlfriend give me a tag-team blowjob.
“Couldn’t we suck him at the same time?” Alyssa asked after a moment.
Madison popped my cock out of her mouth and immediately began stroking the entirety of my shaft. “Oh fuck, yes, we totally could.”
Madison shifted over a bit to make room for Alyssa, who immediately shifted up so that she was next to Madison. Madison took the head of my cock back into her mouth while Alyssa immediately went for my balls. She ran her tongue all over my sack, clearly enjoying herself. She took one of my balls into her mouth and sucked it gently while her girlfriend began sucking my cock with slow, deep strokes. Madison took about three-fourths of my cock into her mouth before slowly rising back off of it, keeping her lips wrapped tightly around my shaft. It felt fucking incredible. If I hadn’t spent most of the evening emptying my balls into Madison’s ass, the two of them would absolutely have gotten me off already.
I watched as Alyssa took the entirety of my sack into her mouth, sucking it gently. She traced her hand up my thigh and rested it just above my cock while Madison continued bobbing her head up and down. Alyssa popped my balls out of her mouth and began to run her tongue around the base of my shaft. Madison took the hint and came up off my cock, opting instead to run her tongue up and down the opposite side of my shaft. Together the two girls sucked opposite sides of my cock. At one point, Madison was sucking on the head while Alyssa was running her tongue up and down the length of my cock. Then the two of them sucked my head at the same time, their tongues intertwining a bit as they pleasured me. They were essentially making out with my cockhead in between their lips. After that, Madison licked her way down to my balls and took them into her mouth, enthusiastically licking and sucking them while Alyssa began bobbing her head up and down on my shaft again.
I honestly wasn’t sure who was sucking me better. Both girls really knew how to suck a cock. And both looked incredible with their lips wrapped around my shaft. Madison would take all of me into her mouth and hold me there while looking up at me with the sexiest look in her eyes. She loved sucking my cock and pleasuring me so well in front of Ashley, I think. And Alyssa was just insatiable. Once she got my cock in her mouth, she would start bobbing her head up and down so fast. It felt amazing. Couple that with Madison gently sucking my balls, and I was in heaven.
Sometimes Alyssa would stop and gently suck the head while Madison would run her tongue up and down my shaft. Then Alyssa would take more of my cock into her mouth, and Madison would return to running her tongue all over my balls. And then it was Alyssa’s turn to lick my nuts, and Madison would take my cock back into her mouth. It was a miracle I hadn’t come down one of their throats already. Thank God for alcohol (and for the events earlier this evening).
“So,” Ashley said after a while. “Clearly y’all are having fun there.”
Alyssa popped my balls out of her mouth so she could speak. “I’m so fucking horny,” she said. “I forgot how much I loved sucking cock.”
“No kidding,” Madison said after coming up off of my cock. “This is incredible.”
“I’m glad to hear that,” Ashley smiled. “But I’m wondering if you guys would like to fuck him?”
Both Madison and Alyssa blushed hard. The two of them glanced at each other for half a second before looking back at Ashley. “Yes please,” they both said together.
“Who wants to go first?” I grinned.
“You got it, baby,” Madison cooed. She scooted back so that she’d have a better view of the action.
Alyssa nodded and then looked up at me, her eyes burning with desire. Slowly, she stood up and climbed onto my lap. She pulled her tank top up and over her head, tossing it down onto the ground behind her, and suddenly I had Alyssa’s bare tits in my face. My hands found her hips, and I took one of her nipples into my mouth. She gasped softly, a soft moan escaping her lips as I teased her nipple with my tongue, flicking it up and down, sucking it gently. She put her hands on my shoulders and looked down at me as I took her other nipple into my mouth. I sucked gently as I reached back and grabbed her ass, squeezing it hard.
I took her nipple out of my mouth and looked up at her. She held my gaze for a moment before I pulled her down. Our lips met, and I wrapped one arm around her back, holding her firmly, while I grabbed her ass with the other. She whimpered softly as our tongues intertwined. Unable to wait any longer, she reached back, and I felt her fingers wrap around me. Carefully, she aligned herself, and the two of us held one another’s gaze as she slowly sank down.
I gripped both of her hips firmly as I felt her. Her warmth. Her arousal. She was incredibly wet. She moaned softly as I bottomed out inside her. I groaned as I felt her pussy tightly gripping my cock. I can only imagine the view Madison had of her girlfriend. Ashley too, for that matter. Alyssa braced her hands on my shoulders again and began to rock her hips. Immediately I could tell she knew what she was doing. She started to ride me — a little clumsily at first, but that could have easily been chalked up to being drunk. I just sat back and watched her — her face, her breasts — as she rode me.
“Oh my God,” Alyssa gasped as she found her rhythm. She bucked her hips steadily. “Oh my God. Oh my fucking God.”
The room was filled with the sounds of our fucking. Alyssa was so incredibly wet. Everybody could very clearly hear the sound of my cock sliding in and out of her pussy as she rode me. And she felt incredible — her pussy was so warm, so wet, so tight. I hoped this was my first of many times inside her.
“I can’t believe I’m fucking you,” Alyssa breathed as her pussy moved up and down my shaft. Her lips were gripping me so tightly; it felt amazing.
“Me neither,” I moaned. “Your pussy feels so fucking good.”
“So does your cock,” she whimpered.
The two of us continued fucking like this for a while. To our right (well, my right, Alyssa’s left), Ashley sat, legs spread, masturbating furiously to the sight of another woman riding her boyfriend’s cock. And sitting on the ground in front of us, Madison was taking in the sight of my cock disappearing inside her girlfriend’s pussy. She watched my balls bounce rhythmically as Alyssa slammed herself up and down onto me, and as loud gasps and moans escaped our lips. Madison could see how wet her girlfriend was for me. She watched Alyssa’s lips gripping my cock as she rode me. And she could hear how incredible I was making Alyssa feel. I wondered if she cared that Alyssa was enjoying my cock in her pussy first.
For a while, Alyssa would do the work. She would bounce her ass up and down while I sat back and enjoyed the feeling of her pussy gripping my cock. Some of the time, the two of us would kiss. Sometimes I would take her nipples into my mouth and suck them or flick them with my tongue. I groped her tits and squeezed her ass, spanking her good and hard. She cried out with a picture of pleasure and pain every time I slapped her ass.
Other times, Alyssa would rest for a moment. She would brace herself against me, and I’d brace myself against her, holding her hips tightly as I began to thrust upward into her pussy. She moaned the loudest when I did the work; I could fuck her much harder and much faster than she could ride me. Clearly she loved having her pussy pounded. Yet again, we were lucky I’d spent so long fucking Madison’s ass, or else I wouldn’t have lasted two minutes inside Alyssa. Especially when I was fucking her like that.
We fucked for another minute or two before Alyssa was on the brink.“I’m going to come,” she whimpered. “Brian I’m going to come on your cock!”
“Good girl,” I said, looking into her eyes. I spanked her ass and grabbed her tits. “Come for me. Come on my cock like a good little slut! Your girlfriend is watching, remember? She’s watching you take my cock. Don’t you want Madison to watch you come on my big cock?”
“Yes,” Alyssa cried out. “Yes, fuck me, I’m gonna come! Oh my God, I’m coming!”
Alyssa leaned forward, clutching me hard as her climax hit. She moaned loudly and dug her nails into my back as I took over and began fucking her, trying my best to match the pace she had been riding me.
“Keep fucking me,” she begged. “Shit!”
I held her hips with both hands as I fucked my cock in and out of her pussy. It was hard to stop myself from cumming as I felt Alyssa’s pussy pulse and throb around my cock.
“Fuck, fuck, fuck, fuck, fuck,” Alyssa breathed. “Shit! Fuck me, holy fuck, oh my GOD!”
“Holy FUCK,” I heard Madison say, though I couldn’t see her. I briefly wondered if she was masturbating before my focus returned entirely to the feeling of Alyssa’s pussy climaxing around my cock.
Finally, after what felt like well over a minute (though in reality it was probably not quite that long), Alyssa’s orgasm finished. She collapsed in a heap on top of me. She was breathing hard. She brought her head up, grabbed my face in her hands, and kissed me deeply.
“Thank you for that,” she said. My cock was still inside her, of course. “Holy shit.”
“How was it?” Ashley asked.
“Just… wow,” Alyssa sighed. “Fucking amazing. You definitely lived up to all of Ashley’s hype.” She winked at me. “I hope you enjoyed my pussy as much as I enjoyed that cock of yours.”
“Oh, I did,” I grinned. “You’re an incredible fuck. If I wasn’t drunk, there’s no way I would’ve been able to last through your orgasm. That felt amazing.”
“We’ll have to go at it again sometime,” she smiled back. “Soon, I hope. There are a few more positions I’d love to fuck you in.” She turned her head and looked at Ashley. “And I wouldn’t mind getting you off in my pussy next time.”
“Yes, please,” I grinned. The thought of pumping a load inside of Alyssa’s pussy was… wow, yeah, that would be great. And if Alyssa stayed interested in anal, then maybe I could fill her ass up just like I had done with Madison earlier.
“Can I join you on the couch, Ashley?” Alyssa asked.
“Of course, baby girl,” Ashley said.
Slowly, Alyssa came up off my cock. I was actually disappointed as I felt myself leave her pussy. But my disappointment was not long for this world. Alyssa walked over to the couch on which Ashley was masturbating. She sat beside her, catching her breath for a moment, before leaning over and kissing Ashley, who enthusiastically kissed her back. I bet they would’ve started making out, and honestly that might have progressed to them having sex, but they stopped before things got too far. They didn’t want to miss the upcoming show, after all.
Madison, who had been watching Alyssa walk over to sit with Ashley, turned her attention back to me. Our eyes met as she rose up off the ground and walked over to me. Like her girlfriend before her, Madison carefully climbed onto my lap. But unlike her girlfriend before her, Madison was in a familiar position. My hands found her ass, and then Madison’s top was on the floor. I took her left nipple into my mouth and sucked it gently. She ran her hands through my hair and moaned softly.
“Are you ready?” I asked her softly, briefly taking her nipple out of my mouth before continuing to suck it softly.
“Yes,” was her response. “I’ve wanted this for so long. And I’m so horny after watching Alyssa take your cock like that.”
Without breaking our gaze, I felt Madison’s hand wrap around my cock. I felt her shift into position as she aligned my cock with her pussy. She held still for a moment, with the head of my cock pressed up against her. She took a deep breath, and slowly, she took me inside her.
Finally. The two of us had been waiting for this moment for a long, long time. We looked into one another’s eyes as Madison sank down. She moved slowly, savoring every inch of me that entered her. She moaned softly as I bottomed out inside her pussy for the very first time.
“Oh my God,” she whimpered.
She braced herself against my chest and slowly began to rock her hips. The tight grip of Madison’s pussy was intoxicating. She felt different than Alyssa. Not better, not worse, just different. But like Alyssa, Madison was unbelievably wet. No doubt she was as turned on as I was. Ashley stopped masturbating for a moment, taking in the sight of her boyfriend fucking her little sister for the first time.
We fucked slowly, carefully — almost as if we’d miss something if we went too fast. Madison maintained a surprisingly good rhythm as she rode me. Her ass rose and fell slowly, but always on-beat. It felt fucking amazing. I couldn’t believe I was finally fucking her. She felt so good; it felt so good to finally be inside her. Her pussy was so tight. Every stroke was heavenly.
“Your cock feels so good,” she whimpered. “I love it so much, daddy.”
“Your pussy feels amazing,” was my response. I had one hand on her ass while the other was groping her breasts. I alternated between pinching her nipples and spanking her, each of which elicited a gasp or a moan.
She began to ride me faster. Her hips bucked. Her back arched. She gasped, cried out. Her ass bounced up and down on my cock harder than before. I spanked her harder. I felt her pussy begin to throb around me as we fucked. Slowly we became more desperate. She clawed at my chest as I gripped her sides. Every movement was intoxicating. I spanked her hard, I pinched and pulled her nipples. Her hair fell into her face as she was overcome with arousal.
Then it was my turn to take over. Like Alyssa, Madison leaned it, bracing herself against my body. Our lips met as I put two hands on her ass and began to thrust my cock up inside of her. She broke away from our kiss, her mouth hanging agape as I fucked myself up into her. Every stroke was pure ecstasy. The room was filled with the sound of our bodies colliding as I fucked Madison’s pussy. Each thrust was bringing me closer and closer to an orgasm that I would not be able to stave off.
Ashley and Alyssa watched, their hearts pounding, as Madison and I fucked passionately. They watched my balls bounce and my cock disappear inside Madison’s pussy. They greedily drank in the sound of Madison’s moans, of our breathing. Madison’s pussy had gotten so wet that we could literally hear every stroke. It was incredible.
“Keep fucking me,” Madison begged. “You’re going to make me come, Brian. Please, I want to come on your cock. I want you to fuck me while I come.”
“Me too,” I grunted. “But I don’t think I can last too much longer…”
Madison’s eyes lit up. “Inside me,” Madison said quickly. “I want you to come inside me. Don’t hold back, I’m almost there.”
“Are you sure?” I asked. But clearly we had both already agreed to her proposition, as neither of us had slowed down.
“Yes daddy,” Madison moaned. “I want your cum inside my pussy. Please fill me up. Please baby. I want every drop inside my pussy.”
“Fuck,” I grunted. That did it. “I’m gonna come!”
“Me too,” Madison said, gasping for breath. “I’m gonna come! Fuck me, oh my God. Fuck my pussy, Brian. Shoot your cum inside me. I want all of it! Fill me with your cum, daddy. Fill your little girl with your cum!”
“Shit!” I felt my balls tighten. I thrust myself as deep inside of her as I could as I began to climax. I clutched onto Madison as her body began to shake and convulse. She came fucking hard. Harder than Alyssa had. Her pussy was throbbing and pulsing around my cock so intensely, she practically milked the cum out of my balls.
I felt the first rope of cum shoot out of my cock, then a second, and a third. Madison’s orgasm coaxed every last drop of cum out of me and into her pussy. My vision damn-near went black as I emptied my balls inside my girlfriend’s little sister.
“Oh my God,” Madison cried out, clutching me tightly as she was completely overwhelmed by her orgasm. Every rope of cum that erupted out of me brought forth a new wave of incredible pleasure. Finally, at long last, I was coming inside Madison’s pussy.
And to our right, Ashley was watching as her boyfriend filled her little sister’s pussy with his cum. And Alyssa was watching as I shot my load deep inside her girlfriend. They watched as I thrust my throbbing cock in and out of Madison’s pussy. They drank in all our moans, our gasps for breath. They watched as we clutched one another tightly, riding out one of the best orgasms of our lives.
My orgasm finished before hers. I held her as she rode out the remainder of her climax. It only lasted another few seconds. She continued shaking a bit once she was done, so I just held her tightly while she caught her breath.
“You good?” I asked.
“Y-yeah,” she said shakily. She was breathing hard. “That was amazing. Far and away one of the best orgasms of my life.”
“Me too. I can’t believe I finished inside you.”
“Me neither,” she chuckled. “Good thing I’m on birth control!”
“Duh,” I said. “I would’ve pulled out otherwise!”
“Speaking of pulling out,” Ashley said. “Don’t pull out yet.”
Ashley got up, gesturing for Alyssa to follow. She knelt down in front of where Madison and I were. Alyssa walked over and sat on the ground next to her.
“Okay,” Ashley said. “When Brian takes his cock out of Madison, a whole bunch of cum is going to start dripping out of her pussy. So I’m thinking, since she’s your girlfriend, that you can be there to catch Brian’s cum when it starts dripping out.”
“Sounds good to me,” Alyssa said. “What are you going to do?”
“I’m gonna clean Brian’s cock off with my mouth!” Ashley said cheerily. “There’s still gonna be plenty of cum on his cock. And plenty of Madison’s juices, for that matter.”
I felt a hand gently begin to caress my balls.
“Man, you really drained him, Madison,” Ashley said. “His nuts feel empty!”
“Do they really?” I laughed.
“Well, not exactly,” Ashley giggled. “But I bet Madison’s pussy is really full of cum right now.”
“Oh yeah,” Madison said. “I could feel him cumming. His cock was throbbing non-stop.”
“Oh yeah,” I said. “That was a huge load. She’s nice and full now.”
“That’s so fucking hot,” Alyssa whimpered. “I can’t believe I just watched a guy come in my girlfriend’s pussy.”
“I can’t believe I just watched my boyfriend come in my little sister’s pussy,” Ashley giggled. “That’s one for the spank bank.”
“I bet,” Madison laughed.
“Are y’all ready?” I asked.
“I am,” Ashley said.
“Me too,” Alyssa said.
Madison slowly rose up as I lowered myself slightly. My cock slipped out of her pussy, and just as Ashley had said, a bunch of cum immediately began dripping out of Madison’s pussy.
“Holy shit,” Alyssa said quickly before lunging forward. She opened her mouth and stuck her tongue out, catching most of the semen on her tongue. She brought her mouth up to Madison’s pussy before sliding her tongue inside Madison’s slit.
“Oh wow,” Madison moaned. “Fuck, wow, that feels really good. Be careful though! I’m a bit sensitive right now.”
“Good girl,” Ashley cooed. She placed a hand on one of Madison’s buttcheeks and rubbed it gently. “Make sure you get as much of Brian’s cum out of her as you can.”
Alyssa hummed an acknowledgment as she continued slurping up as much of my semen from Madison’s pussy as she could. Meanwhile, Ashley focused her attention on my cock. She took me into her mouth, immediately working the entirety of my length into her throat. She sucked me very slowly, knowing I’d be sensitive because of my recent orgasm. I was still pretty hard.
Madison moaned softly as her girlfriend wiggled her tongue around inside Madison’s pussy. I grabbed her tits and squeezed them, and then she leaned forward and planted her lips against mine. We kissed as our significant others cleaned us up. Ashley slowly sucked the mixture of semen and pussy juice from my cock while Alyssa licked up as much of my cum from Madison’s pussy as she could.
Madison and I made out for another minute or two until I felt Ashley release my cock from her mouth.
“All clean,” she said.
Alyssa slid her tongue out of Madison’s pussy. “Same here.”
“Wasn’t that yummy?” Ashley asked. “There’s nothing better than pussy juice and cum.”
Alyssa giggled. “It was pretty yummy,” she said. “And there was so much cum! Like my God, you really filled her up, Brian.”
“Ugh, that’s so hot,” Madison groaned. She gave me one more kiss before slowly standing up. She turned to Alyssa and gave her a kiss. The two of them embraced for a moment. Ashley sat next to me on the couch.
“I can’t believe how turned on I am about that,” Alyssa said. “Why is it so sexy that a guy just shot a load inside my girlfriend?”
“I’m with you,” Ashley grinned. “Kind of the inverse scenario for me, but it’s so sexy that my man just pumped his cum into another girl.”
“Not just any other girl,” Madison giggled. “Your man just shot his cum into your little sister!”
“Even better,” Ashley said. “Fuck me, wow.”
“Sounds like Ashley needs a turn on your cock, Brian,” Alyssa laughed.
“Honestly, you already fucked me tonight,” she said. “I’m sleepy. You can just fuck me tomorrow.”
“Really?” I chuckled.
“Yeah,” she said, yawning. “But you have to fuck me in the ass tomorrow.”
“You got it,” I grinned.
“Yeah, I think we’re gonna go to bed,” Alyssa said sleepily.
“All that fucking really wore us out,” Madison giggled.
“Same,” I sighed. I stood up, as did Ashley. We picked up a bit of the mess we had made before heading to the bathroom to brush our teeth. Madison and Alyssa joined us. The four of us stood there naked, just casually brushing our teeth. It occurred to me that I had fucked all three of them tonight. I had come inside the pussies of two of them, and I fucked one of them in the ass several times. Not a bad way to spend a Friday night if you ask me!
We finished brushing our teeth. Of course, we couldn’t just say “goodnight” like normal people. Instead, Ashley suggested that everybody should get a kiss goodnight. So we went in pairs. First, Madison and I kissed while Ashley and Alyssa kissed. Ashley had two handfuls of Alyssa’s ass while Alyssa had one hand firmly gripping Ashley’s tit while the other caressed her head. Their tongues danced and intertwined together as they ran their hands over each other’s naked bodies. Madison and I did the same. Her tongue traced across my lips before intertwining with mine. She grabbed my ass while I grabbed hers.
The four of us made out in our current pairs for maybe thirty seconds before Ashley said that was enough and we should switch. Madison and I broke away from each other. She reached down and caressed my cock and balls briefly before letting them slip out of her hand. She walked over to her sister, and the two of them embraced briefly. Then Ashley’s hands found their way to Madison’s butt, and Madison grabbed both of Ashley’s tits in her hands. Madison pinched Ashley’s nipples with her thumbs briefly before reaching back to grab her sister’s ass. The two of them kissed passionately, no doubt thinking about how Madison had just fucked me. Their tongues snaked in and out of each other’s mouths as their hands enjoyed the feeling of one another’s bodies.
Meanwhile, Alyssa was gently caressing my balls while I squeezed both of her asscheeks. She had me pressed up against the wall. She managed my nuts gently as we kissed. She ran her tongue across my lips, and then I did the same to hers. Then I bit her lip gently. She moaned and slid her tongue against mine. I ran my hands up and down her back as she stroked my chest gently. I put my hands back on her ass and pressed her against my hardening cock. She whimpered softly before slipping her tongue into my mouth, kissing me hard as I gripped her ass tightly.
I opened my eyes just long enough to glance over at Madison and Ashley. Madison was firmly gripping Ashley’s right buttcheek with one hand while the other hand was clearly in between Ashley’s legs. Meanwhile, Ashley was squeezing one of Madison’s tits while the other was working her little sister’s clit. The two of them kissed passionately, their tongues wrapped around one another. This lasted a little longer, maybe forty-five seconds. Madison and Ashley finished making out. Clearly the two of them wanted more. No doubt, they will be having some alone time tomorrow. It was clear they desperately wanted to have sex, but they were also very sleepy.
Alyssa bit her lip and looked at me. “Thanks for the fuck,” she smiled. “I haven’t been fucked like that in forever.”
“Thank you,” I smiled back. “We definitely need to do that again soon.”
“Very soon. And I want your cum inside my pussy next time, okay?”
“That sounds great to me,” I said.
She planted another kiss on my cheek before turning and following Madison out of the bathroom. Ashley smiled at me, and the two of us returned to her bedroom. Staying true to her word earlier, we didn’t have sex. Instead, we each quickly downed a bunch of water before collapsing in a heap on her bed. Madison and Alyssa did the same.