Chapter 5: Ashley and Paul
I’d met Kari two weeks ago now and it was getting on to the end of July. Meadow was off on a vacation in Europe with her parents for a week. Dena had started dating Rick and was spending a lot of time at his place. Kari and I were still spending most of our copious amounts of free time together and we often hung out with Ashley, which was fine with me.
The second night after Meadow left, Kari and I came back from dinner to find Ashley with a new guy. He apparently was a rugby teammate of her ex-boyfriend’s who he’d introduced her to. He looked every bit like a rugby player, a forward-type, big and muscular. He even had a vaguely Maori looking tattoo on his right bicep. His name was Paul and he had cooked dinner for Ashley. They were just cleaning up the dishes from dinner when Kari and I entered. We decided to kill the evening (Thursday night, but only Kari had to work the next day) by playing drinking games.
The evening progressed nicely. We all got a buzz going early but didn’t get crazy (I’d found that I had to watch Kari because being fairly small meant she got drunk fast). Paul was a cool guy. He was a sophomore at UConn and had been playing in a summer rugby league, where he’d met Ashley’s ex. He and Ashley were just hanging out at this point, but I could see that she liked him. They had similar personalities and interests so I thought they might end up getting a bit more serious. Kari seemed to approve anyway and by around 11, Kari was making plans for us all to go on some double dates.
At one point I got up to go to the kitchen to get some more drinks. We were hanging out in the back living room, which was more cozy and where we all generally hung out. The kitchen separated the two living rooms. Anyway, I’d gone in, grabbed a round of beers out of the fridge and started making Kari a mixed drink (she didn’t like beer, but Ashley did). I could hear giggling from the girls in the other room and I figured something might be up. I grabbed the drinks (rather skillfully I might add) and headed back into the room. Ashley had moved over to our couch and was sitting next to Kari, where they were both giggling still. I looked at Paul and he’d turned a bit red and was looking slightly uncomfortable.
“Did I miss something?” I asked as I passed around the drinks. The girls composed themselves as Paul answered.
“I think Ashley’s fucking with me a bit.”
“I was not,” Ashley looked at me with a mischievous grin and said, “I was just throwing out some suggestions about what to do next.”
Ashley grinned even more wickedly now and Kari burst into giggles again. I was pretty sure that she was becoming quite intoxicated and noted that she might get cut off soon. I’d seen that grin on Ashley’s face before and I was quite sure whatever she’d said to Paul she’d meant.
“Uh-oh,” I said, grinning a bit at Paul. I realized that I’d gotten a bit used to the habits of these girls but other people were still a bit taken aback by it. I figured Paul might be in for a surprise tonight. At this point I was pretty sure anything could happen at any particular point, so nothing would really shock me anymore.
I sat on the arm of the couch and took a swig of my beer as Ashley explained a bit more.
“I just think that it might be kind of fun for some people in the room to try some new things.”
Ashley took a sidelong glance at me before returning her grin to Paul. I was instantly intrigued by what she was saying, as I had an idea already.
“You know, Paul,” Ashley continued, “there are some things that you’ll just have to get used to around here.”
“And she’s not kidding,” I added. I have to admit, it was kind of fun picking on the new guy.
“I mean, we’ll take care of you and feed you, but you’ll have to keep your mask on at all times and stay chained in our basement,” Ashley said, looking as serious as she could. Kari couldn’t handle it and burst out laughing and I nearly did a spit-take with my next pull of beer. Paul’s face sank and I swear he audibly gulped. Ashley lost it at that point and start guffawing along with Kari. [They both had great laughs, different but both great. Kari’s was a sweet, little-girl laugh, while Ashley’s was a boisterous, loud laugh. They both fit their personalities.]
“Dude, they’re totally fucking with you,” I said, wanting to end Paul’s misery. “We’re on the second floor, they don’t even have a basement.”
“Shit,” Paul said, obviously relieved. “Ashley you scared the shit out of me.”
Paul took a deep swig of his beer and sank back into the couch a bit. The girls composed themselves a bit before Ashley spoke again.
“Ok I was kidding about that last part, but I’m also being serious. I think it might be time for us to have a bit of fun.”
I swear I started hearing cheesy porn music in my head as Ashley took a pull of her beer. After setting it down, she did something that surprised me a bit and turned and kissed Kari. It wasn’t just a peck, but a full-on, tongue-in-mouth kiss. It totally took Kari by surprise and I had to reach in to save her drink from falling out of her hand. She responded nicely though, pulling Ashley in as she continued the kiss. I was aroused by this and I’m sure Paul was a bit blown away by it. When the kiss ended, Ashley got up and moved back to the couch by Paul.
”Ok we’re going to play a game for a while,” Ashley said. “It’s called ‘never have I ever’ but we’re going to change the rules. Every time you have done something, you have to take off an item of clothing.”
None of us had that many articles of clothing on, so I figured this would be a pretty quick game. I didn’t quite know how quick, as apparently Ashley had some ulterior motives.
“Ok, I’ll go first. Has everyone done this game before?” Ashley asked. When we all nodded she continued. “Ok, never have I ever had anal sex before.”
She’d told me a week before that she had so I knew that she was trying to get the show on the road. She slipped her shirt over her head before she even really explained what was going on.
“Ok if you have never done the thing, raise your hand. If you have, take off something.”
Paul, looking a bit red again, slipped off one sock. Kari and I laughed while we raised our hands. Ashley looked at him.
“No, socks are a pair, take ‘em both off. And Paul, I wouldn’t have guessed, please explain.”
“When I was a senior in high school I dated a college senior for a while,” he said as he slipped off his other sock. “She was in to some pretty freaky stuff and she had me try it.”
“Ewww, so you’re going to be pretty good at this game,” Ashley said.
“If by good you mean naked faster,” I said, laughing.
“Ok, go ahead Paul,” Ashley said, poking him in the side. She looked good sitting on the couch in a black bra and baggy cotton pants.
“Ok, never have I ever had a threesome,” Paul said finally.
The rest of us exchanged a look before Ashley asked with a rueful grin, “Does a five-some count?”
Without stopping to watch Paul’s reaction, I stripped my shirt off. Kari had done the same, exposing her pink bra. Ashley slipped off her pants, leaving her in matching bra and panties. Paul was shaking his head still.
“Ok, maybe I’m not the only one,” he said.
It was my turn now but I wasn’t quite sure what to say. “Never have I ever masturbated in a room while other people had sex.”
It was a strange one, but I had a feeling I might get Ashley on this one. I was surprised however when Kari slipped her pants off and Paul lost his shirt. My mouth open, I just looked at Kari. This was one thing she’d never told me. Ashley meanwhile remained planted on the couch, smiling.
“Please, do explain,” she said.
“I was drunk at a party one time a few years ago,” Kari said, blushing as she talked. “I had passed out on the floor and when I woke up some people were doing it on a couch. I was drunk and horny so I . . . “
We all looked at Paul for his explanation.
“I was in a fraternity house last year,” was all he said, as if that explained it. Ashley guffawed again and pointed at Kari.
“Never have I ever had sex with anything plastic,” Kari said, smiling at Ashley.
“Well played madam,” Ashley said as she unhooked her bra and let it fall from her perky breasts. She was absolutely comfortable sitting in a lit room in just her panties in front of a guy she’d only met a few days ago (the alcohol probably helped this a bit).
To our surprise, Paul had also stood up to remove his jeans. I must have had a sort of disgusted look on my face because Paul quickly jumped in with an explanation.
“No no no, it’s not like that,” he said. “My girlfriend had this toy that was basically a mold of some porn star’s pussy. She liked to get off while I fucked it.”
“Ok, that’s some pretty weird shit,” Ashley said as Paul sat down in just a pair of boxer briefs. “Ok, those two need to catch up, so never have I ever had sex in a beach changing room.”
Kari lost her bra while I took off my pants, leaving us all in just our underpants. Ashley seemed to think this was enough because she called the game off.
“Ok that was nice, and we found out who needs to try some new things tonight,” Ashley said. Without wasting time, she leaned over and kissed a surprised Paul full on the lips. As he settled into the kiss she ran her hand over his flat stomach. She didn’t hesitate when her hand reached his underwear and dove right in.
Kari apparently had taken the hint from Ashley and settled herself on top of me, her tongue caressing my lips before probing into my mouth. I ran my hands down her smooth back and pulled her close to me. I kissed down her neck to her sternum, and then focused on her right breast. She moaned as I sucked the nipple into my mouth on flicked it with my tongue. As I did the same to her left breast, she stroked her hands through my hair. Her ass felt amazing in my hands as I squeezed and caressed it. By the time I’d finished playing with her breasts she’d begun grinding her pelvis on me. I thought I could feel the wetness from her panties through my boxers.
On the other couch, Ashley was really wasting no time. She’d fondled Paul to hardness (I’m sure that hadn’t taken long) and had slipped his boxer briefs off. She was pumping his cock with her fist while he licked her nipples, which she conveniently had shoved in his face. He did seem to be getting over his initial shock though and was reaching between her legs. Moving up her inner thighs, he made contact with her sex, which elicited a groan from her. It also apparently was the signal to move forward, as she removed her tit from his mouth and kissed a trail down his chest and stomach. She settled down in a kneeling position on the couch, with her lovely ass sticking in the air, before plunging his cock into her open mouth.
“Oh fuck,” Paul exclaimed as Ashley inhaled his shaft. She pulled him out again to focus on licking the head of his dick, running her tongue around the tip and ridge around the base of it. His hand fell to her head as she continued to please him.
Feeling pretty frisky at this point, I lifted Kari off of me and reclined her down on the couch, so that her ass hung off the edge of the seat. I quickly stripped off her panties, revealing her wet snatch. She smiled at me as I dove down to kiss her, kneeling on the floor in front of her. She smelled sweat and wonderful as I licked her pussy from bottom to top, settling on her hooded clit. I pushed her legs back and felt her hands in my hair, guiding my head to where she wanted me. I rubbed her clit with my tongue while reaching a hand down to explore inside of her. She was wet and had obviously shaved recently, so her lips were smooth. She groaned as I pushed my tongue into her for a moment and her hands tightened, actually pulling my hair. She was not really trying to be quiet, as no one else was home but Ashley and Paul.
“Aahh,” Kari said softly, “man I love it when you rub your tongue all over me.”
Neither of us was one to talk during sex so this sort of surprised me, but turned me on at the same time. Renewing my effort, I flicked her clit with my tongue and pushed two fingers deep inside of her, rubbing the top wall of her vagina. Her pussy tightened on my fingers as I continued to feel her. One of Kari’s hands left my head to squeeze her breasts as she moved towards orgasm. I think she’d been turned on because she came fairly quickly. She tightened on my fingers and yelled out in ecstasy as she came on my mouth.
“AAHHH YESSSSS!”
I watched her face, eye’s closed, contorted in joy as she orgasmed. She bit her lip between moans, trying to keep it under control. I tried to do my best to disrupt her control and continued fingering her and working her clit with my tongue. I loved her reaction, from her cries to her hips pumping up and down as I caused her so much pleasure.
She did eventually recover, at which point she pushed my head away and hopped up off the couch. Helping me up from the floor, she hugged me close and kissed me. Before I could really get into the kiss or resume feeling her up, she sank down to my cock, which at this point had slipped through the slit in my boxers and was standing proudly before me. Grabbing it with her hand, she ran her tongue slowly along the underside, from the base to the tip, which she then sucked into her mouth. As she sucked my cock head into her mouth, I looked over to check in on the other couple.
Ashley was still on the couch beside Paul, sucking on his cock. She was engulfing large portions of his dick into her mouth at a time. I could see his shaft glistening with spit on her upstrokes. He had gotten a hand into her panties, where he was stroking her ass. It didn’t look like he could actually reach far enough to slip any fingers inside of her, but she seemed to be enjoying it anyway. She had a hand on his balls, gently pulling on them as she blew him.
Kari was revving up to this point as well. After licking the head a few times, she’d started working more of the shaft into her mouth at a time. She worked her hand up and down on the base of my shaft as well as she sucked on me. Her other hand was stroking up my leg, around back and on to my ass, where she moved me gently forward, humping my cock into her mouth further. I got the hint and started the motion myself. She groaned with satisfaction as I gently fucked her mouth. Abruptly she stopped and removed my boxers, leaving me naked, standing in front of her. This allowed her to rub my balls as she resumed her face fucking.
Hearing a groan from the other couch, I looked over to see Paul maneuvering Ashley a bit. Moving to his side a bit, he was able to get a hand underneath her and slide a few fingers into her pussy. He pumped her hard with his hand while she continued to suck his dick. She also seemed to enjoy this more and was bucking her hips now as he fingered her. She sucked him into her mouth deeply, taking almost his entire shaft into her mouth before removing it entirely. She hopped up of the couch, dropped her underwear to the floor, leaving all four of us now completely naked. Smiling at me, she walked over and dropped to her knees beside Kari, who then stopped what she was doing.
“No don’t stop,” Ashley said, “just for a moment.”
Kari reinserted my cock into her mouth as Ashley leaned forward and pulled one my balls into her mouth. My head rolled back uncontrollably as the two girls worked on me with their mouths. It only lasted a moment though before Ashley jumped up again, this time bringing Kari with her.
“Come on, everyone over to the couch,” she said, grabbing my hand as she went. She plopped me down on the couch in a sitting position, pushing Kari on top of me. I pulled her close and kissed her, wanting to be inside of her. I didn’t have to wait long, as Ashley grabbed my cock and positioned it at the entrance to Kari’s pussy. Kari pushed down with her hips, forcing me inside of her. She was so tight and wonderful, even after several weeks of sleeping with her almost nightly, I sighed uncontrollably. As Kari slid down on my shaft, Ashley gave my balls a quick lick than hopped up on the couch herself. She positioned Paul underneath her and slid on top of him. Now both girls were on top, mere inches from each other, riding their men. Kari slid up and down on me, her wet pussy squeezing on my cock. Kari’s tits were right in my face, so I took one into my mouth and sucked on it. She moaned briefly, but Ashley distracted her by reaching over and pulling her into a kiss. I could see their tongues intertwine as they continued to hump Paul and me.
I watched then as Ashley’s hand slid down Kari’s back to her ass. Running a finger down her crack, she slid it into Kari’s asshole as she humped up and down on me. Kari jumped with shock and pulled out of the kiss with Ashley.
“It’s ok,” Ashley said, keeping her hand on Kari’s backside. “Just let me do this while you work on Greg.”
Kari hesitated, as she seemed to debate what to do next. Trying to help her out, I grabbed her waist with both hands and resumed her up and down movement. She quickly resumed her riding motion and her kiss with Ashley. Soon I could see Ashley’s hand moving as she fingered Kari’s ass. I could also feel Kari tighten with pleasure so she must have enjoyed it after the initial shock. Before long Ashley had moved Paul’s hand into mimicking hers, so both girls had fingers in their asses while riding guys side by side.
While it felt great having Kari ride me, it didn’t last long. Just as Kari began to get close to orgasm, Ashley hopped off Paul and jaunted out of the room, throwing a ‘be right back’ over her shoulder as she left. The three of us shared confused looks, but I thought I might have an inkling of what Ashley had left for. I was proved right when she came back into the room with a jar of lube.
“OK Paul, ready for some fun?” she said, smiling her mischievous grin. Paul nodded dumbly as Ashley pulled him off the couch. She kneeled down in front of the couch and leaned over the seat, presenting her ass to Paul. Squirting a generous amount of lube on her hand, she rubbed her ass and pushed two fingers inside, preparing herself for what was next. Meanwhile I was still inside Kari, but neither of us was moving, transfixed on what the other two were doing. After lubing herself up, Ashley looked over her shoulder and smiled at Paul, who had been stroking himself a foot or so behind her.
“Just go slow, it’s been a while since I’ve done this,” she said. As Paul positioned himself behind her, she reached a hand underneath her and started rubbing her pussy. He grabbed onto her hip with one hand and with his other slowly guided the tip of his cock into her ass. He did go slow, pushing the head in until it popped past her anal ring. Once the head was in, he slowly stroked in and out of her as she groaned. After a moment, he had worked about a third of his dick into her ass and she was really rubbing on her pussy hard.
“Aaahh,” she moaned, “man, I’m cumming already!”
She started humping her ass up and down, instantly driving most of his length into her ass. He grabbed onto her bucking hips and started pumping into her. She settled down after a moment and he was able to establish a steady rhythm.
Ashley looked up and me and Kari (who had not moved since they started) and motioned us towards her with a finger. Kari dismounted me and Ashley guided her to the couch in front of her. Removing her other hand from her sex, she pulled Kari into a reclined position and pushed her legs back, giving her an unobstructed view of her pussy.
“Yeah, this is nice,” Ashley said as she ran a finger between Kari’s pussy lips. “Greg, I believe her mouth is free,” she added as a suggestion before putting her mouth on Kari’s clit. Kari immediately spasmed with joy as Ashley’s tongue connected with her and Kari placed a hand on Ashley’s head. Rock hard and totally hot, I stood up on the couch next to Kari, presenting my cock for her. She didn’t really hesitate and sucked me into her mouth as Ashley caressed her pussy with her tongue.
From my vantage point, I had a great view of my girlfriend being eaten out by one of her best friends and her friend being fucked in the ass by another guy. I was really turned on by the anal sex, as I had been the previous time with Dena. I was overwhelmed by my desire to try it this evening. It was almost as if Ashley read my thoughts at that point.
“Paul, I want you to stop for a moment,” she said, moving forward off of his dick. “I want Greg to try this.”
Her eyes flicked to Kari when she said this, trying to get a reaction from her. I admit I looked at Kari too, mainly to get approval. My girlfriend looked at Ashley first, then up and me. She smiled weakly and nodded her approval. I hopped down off the couch and knelt behind Ashley, assuming the position directly behind her ass. I was excited and nervous at the same time. Ashley grabbed the lube off the floor and squirted more onto her hand. She looked back over her shoulder and smiled as she rubbed my cock, lubing me up.
“OK Greg, just go slow and enjoy!” Ashley said after letting go of my dick. She watched me over her shoulder as I got up right behind her. I exhaled deeply once and positioned myself at the entrance to her ass. I placed the head on her asshole and pushed forward with my hips. I watched as the head slowly entered her ass and started breathing again when the entire head popped in. It was tight, almost to the point of hurting, but felt amazing. I kept pushing in, guiding my shaft with my hand. Once I started pushing in, my cock entered more easily than I’d thought it would and before I knew it, half of it was inside of her. I looked up at her and smiled, amazed at what I was doing for the first time. Pulling out a bit, I started up a humping motion and began fucking her ass. It was tight and smoother than I’d expected, glorious all around. She moaned deeply and smiled at me as I slowly fucked her ass.
As I pumped into Ashley, Paul sat on the couch beside Kari, who was watching me wide-eyed. Ashley looked back at her and stroked her inner thighs and sex some more. She pushed Kari’s legs back and ran two fingers from her clit to the entrance to her pussy. But then she kept going, all the way down to Kari’s ass. Pushing two fingers in, she looked back at me and winked. She pumped Kari’s ass, causing Kari’s head to roll back in pleasure. Her hand stretched out and rubbed Paul’s leg, grasping his cock in her hand when she reached it. I wasn’t really jealous at all as she pumped Paul’s dick with her fist, after all I had my cock buried in her best friends ass at the moment.
Ashley’s ass rocked back into me as my cock slid in and out of her ass. I rubbed and squeezed her ass cheeks as I fucked her, pulling her back down onto me on my in-strokes. Ashley was groaning as I nailed her ass, Kari was groaning while Ashley fingered her ass and I was enjoying the whole scene. Paul was working Kari’s pussy as well and I could tell she was getting close to cumming as her hips bucked and her head lolled.
Ashley pulled forward off of my dick as I felt the first twinges of orgasm rising. A bit disappointed, Ashley pushed herself off the floor and onto the couch next to Kari. She was ready to reposition us all again.
“Kari, do you want to try it in the ass now?” Ashley said to her friend. “I promise you’ll like it, and now Greg’s done it so he can go slow.”
Kari nodded up at Ashley, who smiled.
“Ok Greg, just come up to the couch and make sure you go really slow with her.”
Ashley pulled one of Kari’s legs towards her and pushed her down farther on the couch, so that her ass was almost hanging off the end of the seat. I got up to Kari and pushed her legs back a bit further, so that I had a good view of her asshole. Before doing anything else, I leaned forward and kissed Kari, trying to reassure her that it would be ok.
As before, except from a different angle, I placed the head of my cock at the entrance to Kari’s ass. I slowly moved forward, pushing the tip into her hole. As I felt the head of my cock slide into her ass, Kari started and bucked a bit. Ashley held her tight and stroked her leg as I kept pushing forward, slowly but steadily. Kari was definitely tighter than Ashley, but after a moment, the entire head slipped into her ass.
“Oohh,” Kari exclaimed, almost whimpering as I pushed further into her. She breathed rapidly, almost heaving as I pushed an inch, then two into her tight ass. I rested for a moment, letting her adjust to the cock intruding into her ass. My heart was racing now, as I was fucking this beautiful girl in the ass. I started pushing in and out of her now and felt her relax a bit as I established a slow and steady rhythm. Because of my position, I could rub her clit with a thumb while pushed back on her other leg.
“Oh that does feel good!” Kari exclaimed after a moment. Ashley leaned down and kissed Kari as I sped up my motion a bit.
After kissing Kari, Ashley got off the couch again and moved Paul over a bit on the couch so they had room. Pushing him back into the couch, she turned her back to him and slowly positioned herself over his cock. With her feet still on the floor, she lowered herself onto his cock, to their mutual moans. She pumped herself down on him a few times before leaning back on him. Both of her feet moved onto the couch beside Paul’s knees, so she was almost squatting on his dick, her hands supporting her on the back of the couch. Now that she leaned back, I realized that Paul’s cock was in her ass again. She pumped up and down on him, his large hands guiding her waist in a riding motion.
I moved both of my hands to Kari’s legs, continuing to keep her ass a bit up off the couch as I rammed into her ass. She rubbed her own clit and even slid a finger into her pussy. She came quickly. Moaning and groaning in ecstasy, her hips bucked and her ass tightened on my cock. I couldn’t handle it at this point and felt my cock unleash shot after shot of cum into Kari’s ass. She continued to grind her hips on me, milking every last drop out of my dick as she came again.
Beside us on the couch, Ashley was moaning as well as she rammed herself onto Paul’s shaft. He had both of his hands on her hips as she moved up and down on him. With a massive groan, he pulled down on her hips and held her in place as he came into her ass. She reached a hand down and rubbed her pussy as she swirled her ass in little circles on his cock. After his orgasm finished, she pumped her ass up and down on him, finally cumming herself. She was stuffing three fingers into her pussy as Paul’s dick plunged repeatedly into her ass, her cries of joy filling the room.
After she came, we all flopped down, exhausted. I was laying on the floor, Kari got off the couch and lay beside me, curled in the crook of my arm, while the other two sprawled out on couches. After a moment, I broke the silence.
“Thanks for making us try new things, Ash,” I said. Ashley grinned down at me and Kari, who was nodding approval.
“No problem,” she said as she got up off the couch, “I love trying new things, and tonight was a good night for it. But now I’m exhausted.”
She grabbed Paul’s hand and pulled him off the couch.
“Come on, time for bed,” Ashley said as she led the rugby player out of the room.
Pulling Kari up off the floor, I guided her off to bed as well, both of us completely satisfied.