Friends With Benefits

This is a new story called “Friends With Benefits” Let’s begin…..

Lily had just turned twenty-one. With hazel blue eyes, soft blonde shoulder length hair, and a smile that made most men melt, Lily had been looking forward to this particular weekend for quite some time.

Her two very best friends, Jose and Adam had been talking about taking her out for a night on the town for her birthday celebration. She had known Jose and Adam for years, never intimate with either of them, though they had certainly flirted and teased one another on several occasions. But beyond that, they’d remained simply friends, albeit very good ones. One thing that Lily appreciated about both of them the most, was they could share and discuss nearly everything, trust one another to keep confidence, and rely upon one another whenever there was need.

They had both been by her side after her very hard breakup with her boyfriend Steven, something that had set her back on her heels for several weeks after discovering he’d been banging one of the women he worked with. Something that had been very traumatic for her to accept as she’d given her virginity to him shortly before discovering he’d been sleeping with another woman.

With everything she had recently been through, Lily was looking forward to a fun-filled entertaining night with her two very best friends.

They had gone to one of the local restaurants/bars that was a very popular hangout. Starting out with a tall pitcher of Margaritas, one of Lily’s favorite drinks. She was soon into the swing of things, having a great time joking and laughing with her two friends. When it became known however that it was in fact her birthday, the custom of this particular place was to bring out the “party funnel” as it was called.

Leaning back in her seat, one of the bartenders placed a long thin funnel just above her mouth while another stood on a tall chair pouring the contents of a specially designed birthday drink into the funnel. It was the challenge to see if anyone could keep up with the continual pour until the entire contents of the drink had been consumed. Not really high in alcohol content, it wasn’t designed to make anyone sick or get stupidly drunk. And though she’d already had two glasses of Margaritas, Lily felt more than up to the challenge.

Several other patrons began to gather around their table as the bartender began to pour the concoction down the funnel. Jose and Adam began chanting, “Go! Go! Go!” as she drank, miraculously keeping up with the continual pour. Spilling very little upon herself, though a large plastic bag had been draped around her to prevent ruining her clothing, the crowd began to cheer, giving her a standing ovation for accomplishing a task that very few were able to keep up with.

“Impressive Lily!” Jose said congratulations to her. “Yes, it was…but I’d be willing to bet you couldn’t do that again with a real drink!” Adam challenged.

“Well not now I couldn’t!” Lily admitted. “That was a lot of liquid! Maybe later,” she left the challenge hanging.

“Yeah, right…maybe later,” Adam teased. “Like I said, no way with a real drink!”

Though feeling good, Lily was far from being drunk. But her inhibitions had flown out the window with the party atmosphere as well as having more fun than she’d remembered having in a long, long time.

“Put your money where your mouth is Adam! What are you willing to bet I can do it?”

“Ok…” Adam said grinning. “Twenty bucks says you can’t!”

“That’s it? Twenty bucks? Come on Adam, surely you can make this a little more interesting than that! Twenty bucks seems hardly worth it. Like I said, you’re so sure I can’t do it…let’s really make it interesting!”

Jose perked up at that. “I’m in! So what if we lose Lily?”

She considered that for a few moments, then grinned wickedly. “I win, the two of you have to come over and clean my entire apartment next weekend. And I mean clean it! Windows, floors, dust mopping, everything!”

Suddenly Jose wasn’t as enthusiastic as he was a minute ago. “I don’t know Adam…” he began backing off worriedly.

“And what if we win then?” Adam challenged back.

“Name it!” Lily told him.

Adam was now grinning even more broadly than Lily had. “Anything?”

“Anything,” she replied now wondering if perhaps she’d put her own foot in it as the expression on Adam’s face told her he wasn’t thinking about her doing any cleaning.

“Ok Lily, here’s the bet then. We lose, we clean your entire apartment. You lose, then you come with Jose and I up to my folks cabin next weekend.”

Lily stared at him. “And? That’s it? Just come up to the cabin for the weekend?” Adam actually seemed nervous now as he obviously began mulling over the real meaning behind that. “Not exactly. You lose, you have to do whatever Jose and I want you to do with the two of us.”

Lily stared at her friend incredulously. They’d never been intimate with one another aside from that occasional flirting and horsing around which had included a few semi-erotic wrestling matches. But beyond that, there’d never been anything else.

“You can’t be serious!” she replied thinking that he was in fact kidding around with her.

“Like you said Lily, put your money where your mouth is!”

She sat back in her seat staring at him. It wasn’t that Adam and Jose weren’t attractive looking men, they were. Adam had a boyish look about him that was sexy as hell! He wore his dark hair long in a ponytail, stood a few inches taller than she, with alluring hazel green eyes that could penetrate a person’s soul. Jose was the taller of the two with shorter light brown hair, but had the sculpture of a body-builder though he wasn’t. More than anything, Lily was concerned that getting involved sexually with either one of them might ruin their long-term friendship.

“If I do lose, which I won’t by the way, both of you need to know this is a one time thing. I don’t want it ruining our friendship,” she added seriously. “But like I said, I have no intention of losing either. I expect to see the two of you showing up at my apartment bright and early Saturday morning ready to spend the entire weekend cleaning!”

Once again Jose appeared a little nervous at Lily’s self-confidence. That look convinced her.

“Ok, it’s a bet!” she heard herself saying.

“Pinky swear it!” Adam responded.

In all the years they had known one another, none of them had ever broken a pinky-swear promise. As silly as it might have been, it was the one thing that had cemented their trust between them. Adam was taking this seriously, which meant that if Lily really was going to go along with the bet, she’d have to swear to do whatever it was that Jose and Adam told her to do if she lost.

Lily held up her hand extending her pinky expecting Adam as well as Jose to wrap their own little fingers around hers. What she also realized as she did that however, the mere thought of what this bet meant if she actually did lose had caused her to become somewhat excited.

Adam as well as Jose couldn’t help but notice that either. Lily had luscious full breasts with rather large thick delicious nipples. Both of which had grown erect pressing fully against the tight tee shirt she had worn even through her bra.

Adam surprised her by extending his own pinky out, but rather than wrapping it around her own as she’d expected him to do, he placed it lightly on top of one of her nipples causing her to flinch.

“That’s not exactly my pinky finger!” she started leaning back and away from him forcing Adam’s finger to fall away from her breast.

“It is now…if you’re really serious about the bet!” he challenged her again. “You can back out now if you want Lily. One last chance. Either put up, or shut up!”

By way of an answer, she leaned forward once again. “You might as well pinky-swear on my boob too Jose because I am serious! I’m looking forward to watching the two of you wearing rubber gloves and cleaning my toilet!”


Adam had given Lily easy to find directions up to his parents cabin. As she pulled into the long drive heading towards it, she shook her head in disbelief that she actually really was going through with this. And she’d been so close to winning too! Nearly downing the entire pitcher of Margaritas, the bartender who Adam and Jose had coaxed into helping them had just poured the last of the drink into the funnel when Lily choked suddenly, her mouth pulling away with the last bit of drink suddenly drenching her.

Shocked, she looked up to see both Jose as well as Adam looking just as stunned as she was initially until they both began grinning with the certain knowledge that their wildest fantasies were about to come true!

As Lily pulled her car into the semi-circular driveway, Jose and Adam stepped out the front door of the cabin greeting her. Taking the overnight bag she’d packed, Adam actually leered. “You’re really not going to be needing this,” he said simply, then turned heading back into the cabin. Lily followed, as did Jose who appeared considerably more nervous, almost embarrassed in fact than Adam had appeared.

She had heard Adam talk about his parents cabin before, but had never had the opportunity to see it though she’d actually been invited up on more than one occasion.

“Wow! This is pretty nice!” she admitted as she began following Adam up the spiral staircase leading up to the enormous upper floor. A large balcony overhung the downstairs sitting room where there was also an enormous fireplace that took up nearly the entire length of one wall. Reaching the top of the stairs, Adam gave Lily a quick tour, sitting her bag down on one of the two twin beds inside the smaller of three bedrooms.

“Down the hall is the master bedroom,” he said a bit suggestively with a wink and a smile, letting Lily know as he did that Adam had every intention of holding Lily to their bet. “In here is the upstairs shower, as you can see, it’s easily big enough for four!” once again telling her as he showed her about that he as well as Jose had obviously been entertaining several naughty thoughts. Leading her into the main bedroom, Lily saw that the enormous comforter had already been pulled down revealing black satin sheets covering the bed beneath it. Lily actually walked over to the bed caressing the softness of them.

“Just for me?” she teased nervously herself. Adam nodded his head. “Just bought them for this occasion,” he admitted. “Thought you might like them.”

Lily sat down on the bed. “Now what?” she asked a bit apprehensively. The boys turned looking towards one another.

“Well, like I said when you arrived. You probably won’t need much of whatever you brought along with you. Jose and I will go back downstairs and fix us some drinks, get a nice fire going for this evening so you won’t get too cold.”

“Too cold?”

Daring Friends with benefits will continue on the next page

Series NavigationFriends With Benefits – Part 2 >>

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