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GROUP SEX STORIES

Old Friends and New Opportunities

Old Friends and New Opportunities

by Jilliannes
21 min read
4.67 (11500 views)
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"Cheers, ladies!" Four glasses were simultaneously raised and gently clinked together as the old friends celebrated a lifetime of friendship. They had known each other since they were in college and had remained good friends throughout the passage of time -- even if life had taken them in four different directions and finding themselves in the same zip code together had been rare. Now, three decades later and with all the bumps and bruises inevitably experienced by nearly every person just from being a human, the quad sat together around a table once again, confident in the knowledge that each accepted the others without reservation, without judgement, and with a platonic love for each other that nothing could break.

The reunion of sorts had happened spontaneously and serendipitously. For no reason other than pure happenstance, the four found themselves back in their college town over the same weekend, and the chance to get together just developed organically. A few quick texts were exchanged and soon all found themselves huddled around a table at their favorite pub in the city for an evening of laughter, catching up, and reminiscing about their college years together -- back before the reality of adulting had hit them squarely between the eyes, and before the halcyon days of college life were behind them. Nothing had changed and yet everything had changed. No life is perfect, and as the flowing wine relaxed them, each in turn shared anecdotes about the circuitous roads that they had travelled. They each knew the general paths that the others had taken, but listened intently as their journeys were rehashed and more details revealed.

Tanya had never married. She had come close a couple of times -- the last of which ultimately resulting in the birth of her daughter. Instead of wallowing in self-pity though, she had instead embraced her circumstances and did the best she could to provide a great life for herself and for her now grown daughter who was off in the world making her own way, well-prepared to face adulthood. Tanya was tough, but inside she was still the playful soul that she had been in college. Tanya considered herself bisexual, and perhaps that had prevented her from settling down with a man. It probably was the only part of her that she had kept hidden from her sorority sisters, as the stigma associated with also being attracted to girls was still pretty strong during their college days. Being surrounded by her friends reminded her of easier times when she could discreetly play with others and focus on her own needs privately. Back when her most demanding decisions were which guy was going to have the privilege of dating her on an upcoming Saturday night, or if she would instead hook up with an unknown woman at the lesbian bar two towns away where her anonymity could be preserved.

Lori had been married three times, and the last one had ended when the jerk stepped out on her with a young slut, twenty years his junior and with major daddy issues. It was ridiculous and obvious to everyone around them that the bitch was only looking for security and attention and was more than willing to offer her youthful sexual enthusiasm to Lori's bastard ex, who was clearly too stupid to see it himself. That affair had lasted less than a year, but the damage to Lori's ego and self-esteem was crippling, and she had only recently found the inner strength to accept her new reality and to pledge that there would never be a number four who could hurt her like that. As a younger woman, Lori had always prided herself in being the hot little piece of ass that every guy wanted to fuck senselessly and had usually let them whenever asked, but being the one abandoned for the pleasures of a younger pussy had left her feeling old and inadequate. Her intimate needs were currently being cared for exclusively by a battery-operated friend that she kept in the drawer, but if asked, she would have to confess that a real cock would be a whole lot of fun to enjoy again. Recreationally only, of course.

Val's husband had died of a massive heart attack about five years prior. He had been her college sweetheart, and theirs had been a very happy marriage. No kids came of it even though they had tried for years, but she had nonetheless been left with the satisfaction of a history with him that had been emotionally and sexually fulfilling. Val had enjoyed the intimate attention of plenty of guys during her first two years of college but had decided for her own reasons to keep her virginity intact until she met her life-partner, opting instead to become legendary on campus for her superior oral skills. She had learned to confidently receive from the guys as well, and soon it was well known that a date with Val was almost certain to end with one's balls being thoroughly drained, especially if a guy was also willing to get her off first with his tongue. She had watched as her friends fucked guy after guy in college and had enjoyed listening to their late-night sexual confessions as they told all about the last dick that they had experienced, but once she had John in her life and her hymen had been broken by him, Val had remained true to him through it all. She had no idea how to start over -- not that she really wanted to. As it was for Lori, the idea of a warm, naked body to enjoy again had a certain appeal to it. She was fearful of ever putting herself back out there, however, as appealing as it was to have a new penis to enjoy.

Debbie was the only one of the three whose life had taken the more traditional path. She was married -- at least legally -- to a guy that she met right out of college, had two grown kids with successful careers, a house in the suburbs, and a labrador named Sally. Her life had been financially satisfying and peaceful, but if she were being totally honest, it was more than a little mundane. She appreciated the things that her rather uninspiring husband had provided to her but had been feeling for quite some time that a big part of her had died inside -- a detail that she hadn't shared with anyone other than him. He had gotten bored with her as well, and the two were living essentially as roommates, and neither really cared what, or who, the other was doing. She knew the marriage was over just as he did, and she had evidence that he had moved on romantically, even though they had never actually discussed it. Didn't matter. Debbie missed the fun of college life experienced with the girls, and with a generous number of guys too. Guys that her husband knew nothing about. He knew she wasn't a virgin when they met, but perhaps the body-count number that she had shared with him had been somewhat understated -- way understated! She had left those crazy poundings behind her at graduation however and relegated those fond memories to life-experiences of her past. Debbie knew that there was a whole lot more to the sexual repertoire that she had left unexplored, and given the right motivation, might be willing to step out of her comfort zone. Here with her old friends, recollections of those days of youthful indiscretion moved back to the front of her mind once again, and she wondered if that "right motivation" might show its face before the weekend was over.

Three bottles of wine shared between four women had the predictable impact, and soon their conversation had gotten sillier, louder, and a bit too explicit for polite company. But they really didn't care anymore, as tales of their sexual exploits during their college days became just too much fun to revisit. A table of dressed-to-kill coeds perched upon nearby barstools got quite the earful and soon realized that their current generation actually hadn't invented the hook-up culture like they thought they had, and that they had better get busy if they ever hoped to live up to the sexual exploits of their predecessors.

As so often happens when old friends reconnect and inhibitions are properly softened, their conversation turned to that most basic aspect of the human experience, and the rehashing of one particular college evening became as vivid in their minds as it was in their bodies all those years prior.

"I'll never forget that frat party during our sophomore year! I did things that I hadn't even known I could do! What were their names?" Tanya looked wistfully toward the ceiling. "I actually worried if my asshole would ever recover after that!" The ladies all burst out laughing, especially when they saw the shocked expressions from the coeds at the next table.

"Me too," Debbie added. "Wasn't one Cliff? And Brad, right? What was the third guy's name?"

"That would be Rich," Val added with a lusty breath. "He had the nicest cock I ever had in my mouth, and I always felt that I let him down that night!" Again, the coeds' eyes popped as they listened, and the quartet laughed even harder. "What I wouldn't give to have a chance with that one again!"

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Lori leaned forward and half-whispered to her friends. "Keep it down! You're announcing to the entire bar what kind of sluts we were back in school."

"Who cares! No one knows us in here anymore!" Val quickly retorted as she raised her glass toward their nosey neighbors. Her pronouncement was technically true, but their conversation was clearly being overheard by the other patrons.

Time passed quickly as the foursome revisited what was certainly the most sexually outlandish night of each of their lives. What had started as a drinking game had evolved into an all-out orgy, and before it was through, the four sorority sisters and three handsome frat boys had experienced carnal knowledge that eliminated whatever remaining innocence they might have still had -- except for Val. She had stayed true to her chastity pledge that night, choosing instead to show them that her reputation as the campus blowjob queen was well-deserved. She had enthusiastically applied her oral skills to each of the guys, first bringing Cliff right to his edge before turning him over to her friends to finish the job. Brad was next and enjoyed her talented mouth perhaps a little too much. Val drew his orgasm from him quickly, and before he could pull out, with a guttural moan he deposited his creamy load deeply into her mouth. Val lustfully swallowed every drop of his seed and then turned her attention to coaxing Rich's impressive erection to full mast.

Cliff's youngest uncle had once told him to be a gentleman and focus on a girl's pleasure first if he was ever lucky enough to be naked with a real one, and so he soon was flat on his back, his face firmly ensconced between Debbie's willing thighs as she hovered closely over him - his tongue pleasuring every hidden erogenous zone that it could find. Debbie's orgasm hit her hard, and her pussy gushed onto his face as she lost her control. While he and Debbie had been orally dancing, Lori had been riding on Cliff's cock while masturbating herself with her fingers as she brought herself to a powerful climax. Cliff could finally take no more stimulation, and as Lori's pussy was replaced by her hand and mouth, he ejaculated spurt after spurt all over her face.

But Rich had made the calculated error of pre-gaming with a handful of lotion prior to going to the party, and while Val's blowjob felt amazing, was having a little trouble getting to another orgasm so soon after his solo efforts. On the floor beside them, Tanya was kneeling with her head on the carpet and her ass in the air while her fingers wildly stroked her clit, driving her toward her own orgasm. Rich saw his once-in-a-lifetime opportunity, and reached his hand over to her, pressing his thumb firmly against her little brown starfish. Tanya moaned her consent. Val helped guide Rich's erection against her friend's tight sphincter, and with a little patience and a whole lot of saliva from Val, Rich soon popped Tanya's anal cherry, plunging deeply into her bowel. A few strokes inside and soon her tightness and the shear eroticism of being buried in her ass was drawing a new load of cum from his balls. Rich withdrew and made his deposit onto Tanya's lower back, all within inches of Val's watchful eyes which were glued to the spasming of his cock. As Val finished licking the gooey mess off of her friend, the three were joined by the others and the group collapsed together in a sweaty pile of flesh. They were spent, and a core memory was permanently etched into each of their minds -- a memory that would be called upon during many masturbation sessions throughout their lives. It was an awesome night that never happened again, but for this group of horny college students, was an experience that none would ever forget.

Time had been rather kind to the old friends. They were certainly no longer collegian, but nonetheless, had each stayed rather fit and could still capture the imaginations of men of all ages. Much to the chagrin of the coeds who were each doing their best to attract some Saturday night action, to the three handsome guys sitting together at another nearby table, the four more mature women each fell solidly into the category colloquially known as MILF, and these frat-boys were soon trying to figure out how they might actually discover if the maturity and experience of the quartet could live up to the stories that they were hearing loudly retold. Miraculously, coupled with a generous helping of serendipity, opportunity knocked!

On rather wobbly legs, Val and Debbie excused themselves from their friends and started making their way to the ladies' room. As they passed the boys, Val's ankle twisted slightly and she stumbled unceremoniously into Devon, causing his beer to spill all over the guys' table. His protective instincts kicked in as he caught the slightly tipsy woman whose body was now pressed against his -- one of her hands conveniently resting directly on his cock for support as she tried to avoid the floor. "Oh! I'm so sorry!" Val apologized with a giggle -- her body holding its position against his for a few moments longer than necessary, and her hand giving a couple of gentle squeezes to the penis now in its grip. "I really have to pee, but I'll bring you another beer when I get back, okay?" Val couldn't help but notice the muscles of the attractive young man now holding her as well as the substantial handful in her palm, and silently wondered how his body might look naked, aroused, and thrusting on top of hers. The germ of an idea was starting to form, and she intended to share it with Debbie as soon as they were alone in the restroom.

"Don't worry about the beer. We have another pitcher coming." As the two women turned and hurried to the ladies' room, the three couldn't resist lustfully checking them out. Six horny eyes traced the two fit bodies from top to bottom, and each of the men silently wondered what kind of experienced skills those two could to bring to a bedroom. Silent glances were exchanged and another naughty, but similar, idea was starting to take shape at their table as well.

Tanya and Lori had been watching the train wreck playing out before them. Val had clearly taken advantage of her clumsiness and used the opportunity to sneak a handful of the young man's junk. "Just like college days!" Tanya whispered with a giggle. "I'll bet she did that on purpose!" The guys were each very handsome, and after all the dirty talk about their past escapades over the last couple of hours, there were four very aroused pussies that were going to require the attention of something stimulating before the night was over -- a showerhead, a vibrator, or perhaps some fingers. Or just maybe... Now it was Tanya and Lori whose eyes were meeting, and in whose minds naughty ideas of their own were forming.

Debbie's life may have been rather uninspiring, but she and her husband had made a substantial amount of money that allowed her to afford a very nice two-bedroom suite for the four ladies at the full-service Hilton near the bar. It was spacious, elegant, and equipped with two plush king-sized beds. Convenient.

Once in the ladies' room, Val grabbed Debbie and hauled her into one of the stalls perhaps a bit too forcefully, but her urgency and the wine had gotten the best of her. "That kid has quite the package under those pants!" she started, her words coming out fast and totally unfiltered. "I'll bet he knows how to show a girl a good time! Remember back when we would just haul a guy in here and have our way with him? I really need to get laid, Debbie!"

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"Are you crazy? Those guys are young enough to be our kids! As if they'd want anything to do with a couple of old ladies like us anyway."

"They're not kids! They're college men, and I'll bet they'd be a lot of fun! Just tell me you'd pass up having a piece of that, given the chance. You know you wouldn't!"

"You've had way too much wine, Val! Let's get back to the others before they do something they'll regret."

The women staggered back into the dimly lit bar in search of their friends. Debbie could feel the wetness in her panties from all of the previous suggestive conversation but figured that a good Jilling later in the hotel would take care of that. As they approached their table, however, Val's empty seat was now filled by the tight collegiate ass of the guy she had groped a few minutes earlier, and Debbie's empty chair was caressing that of one of his buddy's -- the third standing between them and all clearly working on convincing the attractive mature women to do some much more private activities with them. Across the table, Tanya and Lori were doing their best to look nonchalant and disinterested as the young men clearly flirted with them, but their body language was giving them both away. The dance had begun.

"So, now you're outnumbered!" Val said as she wrapped her arms around Devon from behind. "Hey, big guy, you boys gonna spring for some more drinks?" Trevor just grinned as the waitress appeared right on cue behind them with another bottle of wine. "Smooth! Aren't you going to introduce us to your friends, Tanya?"

Pointing to the others, Tanya began, "Ladies, these fine young specimens are Marco and Trevor, and the guy you're groping again, Val, is Devon. Guys, meet Debbie and Val." Glasses were once again lifted and what little inhibition remained quickly faded into oblivion. It didn't take long for the banter to turn from silly to suggestive, and small talk about college majors and favorite sports teams was replaced by thinly veiled inuendo. Then the big reveal from Devon:

"Our dads were best friends when they went here. They were Greeks like us -- same frat."

The ladies looked at each other, each recognizing a certain familiarity with these fine young males. The wine was continuing its magic, and Devon continued. "Did you go here too?"

"We did! We were sorority sisters. Do you... know when your dads graduated?" Val asked a bit tentatively, suspecting that fate just might be flinging a very naughty opportunity squarely at them.

"Mid-eighties, I think. My uncle told me a little bit about their college days. Sounds like they were quite the partiers back then!" It was time to turn the conversation to the topic that they all were skating around. "I was drinking with my uncle one night and he got a little too chatty. My dad would've killed him for telling me, but I guess there was one party where our dads were drinking with these girls and before they knew it, they were all naked and had an orgy! Can you believe that? I doubt they ever told our moms about it!"

The look on the ladies' faces turned to shock and the four sat in stunned silence for a little longer than they should have. Val finally spoke what they were all thinking. "Uh, that sounds like a wild night. What's your dad's name, Devon?"

"Rich. Why?"

The four women exchanged knowing glances. "Just wondering." Nothing more needed to be spoken, as each was transported back to one very special evening -- one that they now intended to re-live. The guys sensed that something was up but had no idea what that something was. But it seemed pretty certain that these ladies were ready to bless them with their talents. Body language screamed lustfully and touches exchanged on arms, legs, and elsewhere were anything but subtle. It was clear to them all that a more private venue to continue their evening would soon be a necessity if they wanted to avoid being arrested. A quick confirming glance to her friends shifted the erotic adventure into high gear, and Debbie finally said out loud what all of them were silently thinking. "I have a suite next door at the Hilton. How about we take this party over there so that we can get to know each other better?" The guys didn't have to be asked twice. Trevor quickly settled the bar bill and the group headed out into the night air, each of the guys silently praying that they hadn't consumed so much alcohol that they would suffer the humiliation of whiskey dick once called upon to deliver. And each sensed that they would soon be called upon, maybe even more than once.

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