The next week flew by. Work was just something to pass the time between interludes with Kari. We spent every night together and developed an amazing sexual relationship, as well as a deep personal one. I fell harder for her in a shorter amount of time than I’d ever done before. She confided in me that she felt the same. She’d had a series of what sounded like pretty lousy boyfriends and I was the first one who really got who she was as a person. She was sweet and kind and really wanted to please, both her friends and her family. As an easygoing person, I think I allowed her the ability to relax and I tried to shower her with affection to allow her to relax. In her, I had someone I could confide in and tell her anything to find just simple acceptance. We just clicked.
In the aftermath of the previous week’s orgy, Kari and I decided that it was just a reality of who her friends were. She was not jealous, and neither was I, in fact I was still a bit blown away by the amazing girl who I’d developed a relationship with. She’d told me stories of Dena, Meadow and Ashley that illuminated who they were, three very aggressive, sexual people. I would be lying if I said I wasn’t looking forward to another encounter with any of them. Ashley particularly I seemed to be drawn to, although not in the same way as I was with Kari. The four girls and I often hung out in their loft together in the evening (Kari and I spent every night together, mostly at her place). They were fun and outgoing girls and over the week I opened up to them.
The next week her friends planned a party. On Friday, Kari and I went out to dinner, this time at a relatively upscale restaurant. Kari looked amazing, in a white dress with a haltertop neck that showed off her smooth back. By the time we got back to her place, Meadow and Ashley were already setting up the apartment for the party. The alcohol had already been delivered (Meadow had an older cousin who provided whatever they wanted) and they had moved the couches into back living room, leaving the entire main living space open. The blacklights were turned on, the regular lights were off, and they’d established a bar area. The four of us started drinking and other people starting showing up just a few minutes later.
The party was really bumping by about 10:30. There were maybe 30 people there, mostly friends of Meadow’s and Dena’s. Dena showed up with one of her other best friends, Dawn, and two slightly older guys from a band around 10 o’clock. My friends also showed up around that time and I introduced them all to the girls. They seemed to enjoy the fact that about half of the people at this party were eligible females, a seeming rarity at such parties.
Kari drank heavily throughout the evening. I took it easy, mainly just sipped on beer most of the night, in order to keep an eye on the hard-charging little blond. Around midnight she was thoroughly trashed and I had to cut her off shortly after. By 1 am I had to take her to bed. She encouraged me to go back to the party and let her sleep and she passed out a second later.
Taking her advice, I headed back out. At this point, most people were heavily intoxicated, including my friend Chad, who seemed to have hit it off with Meadow. They were in the middle of the living room, grinding on each other in vague keeping with the beat of the music. Ryan and Michael were talking to some other girls, but weren’t having quite as much success as Chad.
Dena was dancing with one of the two band guys she’d come to the party with. I’d gotten a chance to talk to them a bit earlier and they seemed like cool guys. Rick was the bassist in a band in Bridgeport and his cousin Travis was a drummer in a different band. Rick was 24 and Travis was 22, so they were quite a bit older than most people at the party. They were both tall and thin, with black hair and heavily tattooed. They weren’t the kind of people I usually hung out with, but they were friendly enough and Dena really seemed to like Rick. Kari told me early in the evening that Dena had a thing for musicians, particularly older ones. Apparently she’d dated a 22 year old for a large portion of her senior year before he moved to California.
Anyway, Dena was all over Rick on the dance floor. After taking Kari to bed, I found Ashley, who was just saying goodbye to some people who were taking off. The party was tapering a bit, and there were probably only about 20 people left. Ash and I grabbed a drink and spent most of the rest of the night talking and monitoring the party. Around 2, Meadow and Chad disappeared into her room, Meadow winking at Ashley as she left. Ashley told me this was the signal that my friend was getting lucky tonight. Ryan and Mike left shortly after that, and most of the remaining guests followed suit. By 3 am, the only people remaining were me, Ashley, Dena and the two band guys, her friend who brought them having left. We shut down the music and moved the two couches back into the living room. Dena found her way to one couch, with one guy on either side of her. Ashley wanted to keep an eye on them, just to make sure Dena was ok, so we sat on the other couch. With the light from the kitchen giving us enough to read, we grabbed an issue of Cosmo and read through one of the articles, 50 Hot Sex Tips.
We sat close, our hips and shoulders pressed together as we read through the tips and talked about which ones we’d done and which one’s we’d like to do. I found out some interesting things, like that Ashley had had anal sex before and that she actually kind of enjoyed it. She’d gone down on a girl before, although I suppose this wasn’t a big surprise given her friends and the activities of the previous week. She’d also had sex with two guys at once, which was quite surprising. She informed me that Meadow and Dena had also had threesomes before. I was getting a bit turned on by our closeness and our conversation. We kept an eye on Dena and the band guys, who were talking softly on the other couch. They seemed to be very close as well, with Rick’s arm hanging over Dena’s shoulders and his head mere inches from her ear as they talked. Ashley and I exchanged a look at one point, with both of us seeming to know where this was headed.
We didn’t have to wait long. Rick finally leaned in and kissed her, his free hand moving down to stroke her leg. After breaking off a long kiss, the raven-haired 18-year-old turned and kissed Travis. Ashley and I both watched as Rick’s hand made its way under her black skirt. Her hands moved as well, one for a thigh of each guy. Ashley subtly dropped the Cosmo as we watched the three make out. Dena moaned quietly and spread her thighs as Rick’s hand moved unseen under her skirt. She stroked the two guys legs, working her hands towards their crotches. She alternated long, tongue-y kisses between the two rockers. Travis moved his hands to her large chest, rubbing each of her breasts in turn.
After a moment, I noticed Ashley’s hand creeping up my thigh. I put my arm around her shoulder, allowing her to snuggle closely into me. We didn’t necessarily try and make it subtle that we were watching and at one point Dena looked over at us and smiled.
Rick’s hand at this point was obviously stroking her sex, her hips moving up and down under her skirt. Her hand had found the growing bulges under the ratty jeans of both guys and was working them aggressively. Travis kissed her neck and crept under her white halter top as Rick kissed her mouth. Suddenly she stopped kissing and rubbing them in order to undo the tie behind her neck and slide her top over her head, exposing her braless breasts. Her hands quickly returned to their crotches and Travis attached himself to one of her breasts. Rick continued to do whatever to her under her skirt, which was riding up her hips severely at this point. She was continuing to moan softly, obviously enjoying herself.
Ashley’s hand moved up to my cock, which was getting hard already. After feeling me, she leaned up and kissed my cheek. I moved in and found her mouth, our tongues meeting and caressing. Without really thinking, I moved a hand up to her face, stroking the smooth skin of her cheek and gliding my hand down her neck. She moaned and smiled before kissing my ear. I shivered just a bit as she ran her tongue on the inside curve of my ear, leaving a cold, wet trail as she made her way down my neck with her tongue. It was incredibly sexual and I wanted her intensely at that moment.
On the other couch, Dena pushed Rick over and went horizontal. Her hands working diligently, she unbuttoned Rick’s jeans and freed his hard cock. Fully erect, he was quite long, probably at least seven inches, but much thinner than me. Dena’s mouth moved down to the exposed dick and engulfed the head, her cheeks caving in as she sucked on it. On the other end, Travis spread her legs, propping the upper one up and scrunching her skirt up around her waste. After quickly removing her thong, he went down on her cleanly shaved pussy. She moaned, rather loudly this time, as his tongue moved over her sex. To be honest, I thought it was very odd and uncomfortable to be watching other people start having sex. I’d never seen an aroused man in person, and it was different to be a matter of feet from it.
The thing that kept me from being too uncomfortable was Ashley. She was kissing my neck while rubbing the bulge in my jeans. She was watching the others as well as she did all of this. After they switched positions, Ashley shifted from her position, sitting up and throwing a leg over me, so that she was straddling me. She grinned down at me, a beautiful, mischievous grin, as she pulled my polo shirt over my head, leaving me bare-chested. She followed suit, removing her sleeveless, low-cut blue blouse over her head. She had been bra-less as well, so her perky breasts were now exposed a mere inches from my face. Placing my hands on her smooth back, I pulled her close to me and began kissing her chest, first between her breasts, then each one in turn. I pulled and flicked on each nipple until they were hard, which didn’t take long. I leaned forward and supported her back as I kissed her flat, muscular stomach.
“Ok,” she said, pushing me back into the couch, “time to take your pants off.”
She dismounted and stood in front of me as I quickly unbuttoned my jeans. She assisted in the removal of these and took my socks off.
”Those too,” she said, pointing at my boxer shorts. I’d left them on, not wanting to be too forward. This was obviously not necessary, as she disrobed completely after I took off my last article of clothing. She pulled off her skirt and underwear in one sexy smooth movement, leaving both of us naked. Wordlessly she pushed me back down on the sofa, lengthwise this time so I was lying down completely. She then mounted me in a 69 position, one that was familiar to both of us from the orgy the other night.
Ashley grabbed my erect cock in her hand and slowly started pumping it up and down as we both looked over to the other couch, just to check in. Travis was still eating Dena’s pussy and she looked like she was close to cumming, as her hips gyrated wildly. He was licking her clit as he slammed several fingers into her pussy. He had started removing his pants, exposing his hard cock. Dena was busy herself, as was still concentrating on Rick’s dick. He had moved so that she could lie down and was half-standing, half-straddling her and fucking his dick into her mouth from overhead. She had one hand on his balls and the other massaging her breasts. She groaned loudly as she came, though Rick’s cock muffled her cries.
Ashley and I moved back to our own activities. I felt her mouth moved down to take in my cock as I ran several fingers over her moist snatch. Running a finger over her clit briefly, I raised my tongue to it and flicked. She reacted instantly, her hips shuddering ever so slightly. I ran my tongue up the folds of her pussy and down again, returning to focus my oral attention on her tiny button. I ran my hands over her round ass and inserted two fingers inside her as she continued sucking my cock. Her hands ran over my balls, caressing them and pulling on them gently.
After a few minutes, she moved her mouth off of my cock and on to my balls, sucking on one, then the other. She continued pumping my prick with her fist as she paid attention to my balls. Shifting away from me slightly then, she lifted my balls and licked my perineum. I groaned audibly as she ran her tongue over this sensitive area below my balls. The real surprise came when she flicked her tongue over my asshole a few times. It felt good, but it was shocking and I jerked my hips and she discontinued this, returning to my balls for a few licks. I redoubled my efforts on her pussy as she straightened up a bit. She was still pumping my cock, but was looking over at Dena and the rockers again.
They had changed positions now, so that Dena was on her side, sucking Travis’ cock while Rick finished stripping the rest of his clothes off. He got down on the floor behind Dena’s ass and moved his hand in towards her pussy. Inserting a few fingers in her, he licked her a few times. Making a subtle change in his hand movements, Dena started a bit and removed the cock from between her lips.
“Oh yeah, stick that finger in my ass,” she said. “Man, that feels good. I love having my pussy and ass played with while I suck a dick.”
Thrown off a bit by her dirty talk (though not terribly surprised), I returned to Ashley’s pussy, which was dripping wet at this point. I licked her clit and sucked on it a bit as I fingered her. Feeling a bit bold, I moved my other hand down and rubbed my thumb over her asshole. She was licking my dick head and moaned as I inserted my own finger in her ass. Her hips moved up and down, pumping her pussy onto my face and fingers as I felt her tighten. A moment later she was cumming, with two fingers in her pussy and one an inch deep in her ass. She sucked hard on my cock as she spasmed her way through her first orgasm.
After she subsided, she climbed off of me and took my hand. Helping me into a sitting position, she leaned down and kissed me for a moment before turning around. Backing into me, she spread my legs apart and mounted me in reverse. She arched her back, sticking her ass out slightly and reached back to grab my cock. She rubbed my dickhead over her clit a few times before positioning it in the entrance to her pussy. Without looking back, she slid herself down my shaft. With a few up and down movements, she sunk entirely down onto me with a sigh. From this position we could fuck and watch the other three as well.
Dena came again before they switched positions again. Travis sat down on the couch and Dena mounted him. He immediately grabbed her ass and started her moving up and down on his cock. Rick stood up on the couch beside them, allowing Dena to pump him while she rode his cousin. She pulled him by the dick until he was close enough that she could stick him back in her mouth. His head rolled back and his hands ran through her shoulder-length black hair as she orally pleasured him once again. As she bounced up and down on Travis, she started deepthroating Rick’s long cock, taking in most of his length at a time. Before long I could see copious amounts of sticky saliva coating his dick and dripping down to his balls. He grabbed her hair with his fist and assisted in the movements of her head, holding her head down until she almost gagged each time. Below Travis ran his hands over her breasts and ass, often venturing down to rub the bud of her asshole with his fingers. She rubbed her own hands over her breasts and ass as well, moaning incessantly, though not very loudly.
Meanwhile, Ashley rode me, often looking back over her shoulder to smile at me. Steadying herself on my knees, she basically stood and rocked up and down on my cock. I ran my hands over her beautiful ass and hips. We kept a pretty slow pace, as we both seemed quite interested in watching the others. Occasionally, Ash would reach down between her legs and rub my balls briefly. Her pussy was tight but smooth from wetness and we fit well together. Her well toned body was beautiful and I watched her intently as she rode me.
Dena spasmed again and came, this time removing Rick’s cock from her mouth and kissing Travis as she came. As she started cumming, Travis’ hand went over her asshole again, this time sliding two fingers inside of her. Her hand followed his down and grabbed his wrist. I’d suspected she would remove his hand but instead she moved his hand so that his fingers pumped her ass as she came. After her orgasm subsided, she hopped off of Travis and grabbed both guys by the hand. Moving down to the floor, she positioned Travis in front of her and Rick behind her, with her on her hands and knees between them. Inserting Travis’ cock in her mouth, she moved her hips back and rubbed her ass on Rick’s shaft. Grabbing her hips in one hand, Rick entered her from behind. As he pounded into her pussy, he inserted a finger into her asshole, causing her to squeal a bit.
I was very turned on watching all of this. Ashley’s pussy rose and fell in a slow but steady rhythm on my shaft. I ran a hand down her ass to the rosebud of her ass. I probed a finger inside slowly. Ashley leaned back, forcing me to remove my hand from her ass, until her back was pressed against my chest, her head moving back by my ear.
“You can’t fuck my ass tonight Greg,” she said. “Maybe at some other point, but I didn’t plan on that tonight, so it’s a no-go.”
“That’s ok,” I said, a bit shocked by her directness. “I’m still having a good time. You are so incredibly sexy, I’m having trouble holding back.”
“Oh Greg, you feel amazing inside of me,” she said, kissing my cheek. “So watch this, I bet you anything that one of these boys fucks her in the ass soon.”
Kissing her neck, I rubbed my hands up to her breasts and gave them a quick massage. Grabbing her hips, I pulled her up a bit.
“Here, let’s switch positions,” I said. She got off of my cock and stood up, looking back over her shoulder at me as I stood up. Unable to resist, I pulled her in for a kiss before moving her into position. I pulled her down to the floor in front of the couch, placing her on her back in front of me. I kissed her neck down to her breasts, where I was able to suck on her nipples for a bit. Her hands played through my hair, driving me even a bit crazier. Placing my hands on the backs of her legs, I pushed them up a bit, giving my cock a clear shot at her pussy, which Ashley was rubbing in anticipation. She grabbed my cock and directed me back inside of her. Once inside, we both returned to watching the other three, who were now just a few feet from us on the floor. My uneasiness of watching others was completely gone now, as my state of arousal was enough to make me not care about it anymore.
Rick was still fingering her ass as he rammed in and out of Dena’s shaved pussy. Dena was pumping Travis’ cock with one hand while sucking on him with her lips, both of his hands pressing down on her head. He was chanting ‘fuck yeah, fuck yeah’ quietly as the younger girl sucked his cock.
Just then I heard a door down the hall open and Chad step out into the hallway in just his boxers. Seeing the activity in the living room, he quickly stepped back into Meadow’s room and closed the door. I laughed a bit to myself. I hadn’t really told my friends much about these girls, so he’d really had no way of suspecting what he’d seen. With the lights off in the living room and just a light from the kitchen, he’d likely not been able to see who was involved, just that someone was getting it on in the living room.
I fucked into Ashley’s pussy as she wrapped her legs around my hips. I could feel her muscles tighten around me as she pulled me close to her. Her hands wandered across my back, lightly scratching with her nails as we both intently watched Dena and the two guys.
At this point, Rick removed his hand from her ass and grabbed her by the tits, which were swinging gloriously as he fucked her from behind. He pulled her up off of Travis’s cock and up close to him. He leaned in so that his mouth was right by her ear.
“You’re so fucking hot Dena,” he whispered, just loudly enough for Ash and I to hear. “I want to fuck you in the ass, is that ok?”
“Oh fuckin-a,” she said, more loudly so that everyone could hear, “I want you in my ass so fuckin bad, I was just waiting for someone to ask. Hold on, I’ll be right back.”
I looked down at Ashley, who was smiling up at me with an ‘I told you’ look. I leaned down and kissed her just for being so beautifully smug.
Sliding off of Rick’s cock, Dena hopped up off the floor and ran down the hallway. She came back a minute later carrying a small bottle. Handing it to Rick, she leaned down and kissed him vigorously before resuming her position on the floor. Not waiting for Rick, she pulled Travis’ cock back into her mouth and pushed her ass up high for Rick.
I watched this part intently, as I really had no idea what anal sex entailed. Rick opened the bottle of lube and squirted a fair amount over Dena’s pale ass. He rubbed it from her ass to her asshole, which he pushed two fingers into. As he fingered her ass, he squirted a bit more lube onto his fingers so that it really got into her ass. After a moment he removed his fingers. He emptied a bit more of the lube onto his cock and rubbed it in with his hands. Tossing the bottle aside, he kneeled closer to Dena and rubbed two fingers over her ass again. Placing the head of his prick against her ass, he pushed in slowly. Despite the low light, I could clearly see the head slide in slowly past her anal ring. She squealed again as he entered her ass. Going slowly, he eased more of his cockhead into her ass until he was in a few inches.
Dena was pumping Travis hard with her mouth now and her ass squirmed a bit as Rick worked his way into her ass. He grabbed her hips with one hand and worked a second inch of his cock into her. Pulling her back onto him to assist in the process, he stopped after the second inch was in and started pumping into her. As her ass loosened a bit, he was able to move in more smoothly and finally was able to let go of his cock and grab her waist with both hands.
“Oh fuck yeah!” Dena exclaimed, removing Travis’ cock from her mouth temporarily. “Fuck me deep in my ass.”
“Fuck you’re ass is tight girl,” Rick said in return. “I’m gonna cum all up the inside of your ass.”
”Please, I want you to cum in my ass,” she said, pleading with him. “I want you both to cum in my ass.”
“Dude, you’ve got to get in this,” Rick said, looking up at Travis. Sliding his dick out of Dena’s ass, he grabbed the lube and tossed it to his cousin. Travis lubed up his cock and got behind Dena. His cock was a bit smaller than Rick’s and she was loosed up a bit, so he slid into her fairly easily.
“Ugghh,” he groaned as he entered her ass. “That is so fucking good, I can’t believe it.”
As Travis started pumping his cock in Dena’s ass, Rick stood beside her, pumping his shaft with his hand. She rose up a bit so that she could lick his balls while he stroked himself.
Watching Dena take two different cocks in her ass turned me on pretty much to the point of no return. I’d been slowly pumping into Ashley but now I looked down at her and picked up the pace. Pushing myself up a bit more, I took her legs behind the knees and pushed her legs back and fucked her vigorously. Her pussy tightened and she moaned as I picked up speed. She moved a hand down to her crotch and rubbed her clit as she moved quickly towards orgasm. Her head went back and her back arched as she cum.
“Aahh, Greg fuck me!” Ashley said, her pussy convulsing on my cock. This was too much for me and I let go, cumming inside of her. I kept pumping in and out of her as she came a second time in a row, her hand working on her clit briskly.
After we finished, I leaned back down and kissed her, pushing my tongue into her mouth aggressively. Hers fought back equally and we squeezed each other passionately for a moment before I pulled out. She rolled over on her side and I lay beside her, caressing her body as we watched the other three still going at it.
Travis was continuing to pump her ass while she licked Rick’s balls and perineum. Dena was now working her own clit and propping herself up with one hand. After a moment, Rick moved back and replaced Travis at her ass. Instead of kneeling this time, Rick pushed her front end to the floor so that her ass was sticking up high in the air. Squatting over her, Rick pushed his cock back into her ass, this time pumping down into her. She moaned as he reentered her and rubbed her pussy with her hand. Travis went back to her head and laid down so that she could lick his balls as she’d done with his cousin. Gladly obliging, she took his dick in her hand and stroked him as she played with his balls.
Rick was really pounding her at this point, with most of his cock fitting inside of her ass. Dena put several fingers inside of her pussy and fingered herself while the bassist fucked her ass. After a moment, she came and convulsed underneath the anal assault. This must have tightened things for Rick, who pumped his load into her shortly after.
“Fuck fuck fuck,” he chanted as he rammed himself down into her ass. “Damn, your ass is so fuckin tight. I pumped so much fuckin cum into your ass girl. Fuck!”
Extracting his cock from her stretched hole, he moved so that his cousin could have another turn fucking her ass. Rather than from behind, Travis sat with his back against the couch and pulled Dena on top of him, with her back to him. Positioning his cock at the entrance to her ass, Dena took over, sliding down onto him. She leaned back over him, steadying herself on the couch with one hand and rubbing her pussy with her other. From this angle I could clearly see her ass stretching to accommodate the cock entering her from below. Her tits bounced up and down as she went up and down.
At this point, she had four of her fingers sliding in and out of her pussy as she rode the cock with her ass. She was almost in a constant state of orgasm at this point and the only thing that really kept her quite was Rick kissing her from overhead. His hand was still working his cock as she rode his cousin, but he was quickly losing his erection.
Travis didn’t last long. With a series of grunts, he pulled her down on his cock as far as she would go and held her as he came inside of her. She continued to grind her ass on his cock for a few minutes as her most recent orgasm subsided. After another moment, she dismounted him and stood up. Helping Travis up, she stood between the two tattooed rockers and kissed each one in turn. They each caressed her shoulders and back as she kissed them, they’re hands still feeling and probing. She flopped down on the couch and sprawled, seemingly spent. The guys started collecting their clothes from the floor as Dena let out a sigh of contentment.
Now that the show was over, Ashley and I got up and picked up our clothes as well. Ashley winked at the guys before talking to her roommate.
“Dena, that was so hot,” she said, grinning at her friend.
“I love anal sex,” Dena said dreamily from the couch. Rick chortled a bit as he put on his underwear and shirt. “And I totally love it when I get to fuck two guys at the same time.”
Shaking my head a bit, I slid my boxers back on and looked at Ashley, who was smiling up at me, still stark naked. She grabbed my hand and led me out of the living room, throwing a cheery ‘goodnight’ over her shoulder as we left. Stopping in front of Kari’s door, she leaned up and kissed me again.
“I had a really good time with you this evening,” she said. “And I really love having sex with you. I’m glad that Kari is cool with it, because otherwise I’d have to try and steal you away.”
“You girls are amazing,” I said, grinning down at her. “I’m still trying to get over how lucky I am.”
She leaned and kissed me again before heading down the hallway.
”Night,” she said.
“Goodnight,” I said as I entered Kari’s room. Tossing my clothes on a chair, I dropped into bed next to Kari and fell asleep.