The Challenge Club

Jack loved going to the Summer's farmers market, for more than just the good food. Every Saturday during the long hot summer, he would fill his bag with everything from fresh local produce and baked goods to hot sauce and artisan chocolates. He would also fill his head with a catalog of hot woman that feed his appetite for fantasy characters. These personas would be inspiration during his long Saturday afternoon masturbation sessions.

As a young, single professional Jack didn't really have a problem meeting, or dating woman--an unending supply of dating apps made that easier than ever. The city was large enough, and single enough, that those apps--even the more niche ones--provided no shortage of choice, and that variety was perfectly represented in the city's outdoor farmer's market.

Every Saturday Jack would stroll through the market, drink a cup of good coffee and enjoy eat a breakfast sandwich while he watched the crowd. There were a few regulars he would always spot--most of whom already appeared in his afternoon fantasies--but there were also a limitless stream of new faces.

Jack didn't really have a type; he could appreciate the beauty and sexiness of all women: the older MILFs who's husband's was on the golf course, the younger MILFs pushing strollers, their bodies full of motherly curves; the mid-thirties professional types showing off their tight asses in the latest expensive athleisure wear; the rumpled college girls in baggy sweats looking for a hangover cure--his list went on and on. And the woman didn't need to be single, or alone, to win a place in Jack's vivid imagination, he was just as happy to picture them having wild, adventurous sex with their boyfriends.

It wasn't just about jerk-off fantasies either. Jack found the farmer's market to be a wonderful place to actually meet women. Everyone was so happy to be there, enjoying the sunshine and good food, that it fostered an inherit friendliness which made casual conversation easy and effortless. In fact he'd dated, and fucked, more than a couple of woman he'd met while sampling juices and pies.

Today Jack's shopping list included fresh veggies from the local grower. The aisles of folding tables were crowded as he picked and bagged, his attention largely focused on the bins of produce. He paused to carefully size up and squeeze a few avocados. That's when he noticed the woman across from him doing the same with a bin full of cucumbers. In the periphery of his vision he mistook her for a guy. She was wearing a plain white v-neck tee and her hair was buzzed short; all one length. Once he realized his mistake has felt embarrassed for even considering it. Her facial features where so delicate and beautiful there was no question of her gender. Her white tee was stretched taunt over her small chest. Braless, her dark nipples where clearly visible through the shirt. Traveling down her small frame he found a thin waist and ample hips--womanly in every traditional way.

She seemed lost in thought as she repeatedly picked up cucumber after cucumber; lifting each on her palm, moving her hand up and down as to feel the weight and heft, and then curiously wrapping it with her thumb and middle finger to check the size. Some were in fact so large that her small hand could not encircle them. Jack alternated his glance from the produce up to her face, trying to catch her eye. It seem obvious what she was doing and he wondered how she might react when caught by a stranger who knew that she was going to do more than eat that cucumber.

At last her attention broke from the green phallus in her hands and she locked eyes with Jack. An embarrassed grin broke quickly across her face and her cheeks grew noticeable flush.

"Have you found just the right one?" Jack asked with a playful tone.

"Oh, shit, ahhem, yes," she cleared her throat and then let out an odd giggle, "I think so."

He looked through her basket at her other items; more salad makings, a loaf of sourdough, a bottle of pop, and a couple of large eggplant.

"What's on the menu?" he ask.

"Oh, well, special recipe actually. I need everything just right," she replied, holding up the chosen vegetable and giving is a suggestive shake.

Clearly she's not overly embarrassed, he thought, or she would have already bolted.

"Have I seen you here before?" she asked.

"Maybe, I'm a regular. I don't recall seeing you though. I'm Jack, by the way," he said, extending his hand.

She awkwardly reached to shake with the cucumber still in her hand before catching the mistake and putting in her basket, "Hah, sorry. Justine. Nice to meet you. I'm actually here most weekends as well, but I might have looked different. My hair was much longer. I just buzzed it; bit of a crazy impulse," she said self-consciously.

"Well it suits you," he said. In fact she looked incredible. He can't believe he'd never noticed her before. "Can I buy you a coffee? That Blue Brew cart has good stuff."

"Ok, sure," she replied.

Sitting at a small plastic table aside the coffee stand they made a bit of small talk about the weather and their favorite market vendors. The conversation was light and easy, but largely pointless. Jack already knew that Justine would play the primary subject of this afternoon's jerk-off session. Now getting a better look at her, he saw she actually topped his 5'10" height. Her build was thin, but not what he'd describe as skinny--more of the lean tautness of someone has been athletic all their life. In watching her handle her cup of coffee he also discovered her hands where not small at all. She had long elegant fingers with nails painted dark navy blue--they made the size of the produce she handled seem all the more impressive.

"So, about this special recipe you're shopping for, what exactly are you going to be eating?" he asked, figuring he might as well push things ahead--he knew exactly why she was shopping for cucumbers.

In fact, Justine was fully aware she was caught sizing up the produce. She had been watching Jack for a while and timed her trip down that aisle just right. There was more than veggies on her shopping list today. But, still feeling she needed to feign some embarrassment she started hesitantly, "Hum, well, so, no actual meal involved. But there is a recipe!"

"What exactly does that mean?" he replied curiously.

"Ok, well, shit, I can't believe I'm going to tell you this, how do I explain. Ok, so the recipe is more of a list really. My girlfriends and I found this challenge thing on the internet. It involves a list of things, and cucumbers and eggplants are on the list. Oh, and the pop bottle too." She wasn't yet ready to reveal that he was on the challenge list as well.

Jack could feel his cock already stirring in his shorts. "Ok, so how exactly does this challenge work," he asked, throwing the challenge in air quotes.

Doing her best to continue the coy-act, she continued. "Oh my god, ok ok so. Aheem," she summoned mock courage, squirming and stamping her feet, "so the challenge is an ordered list of things you have to, uhmm, masturbate with. There; I said it!

"Oh wow!" Now it was Jack's turn to fake a startled reaction.

"So the list starts small and gets bigger. It also says which, um, entry point, the object needs to go into. If you know what I mean."

He did, and so did his dick, which was now at full attention. His mind quickly flashed back to the produce in her basket--none of it was small.

"So, based on your purchases I'm to assume you've already worked your way through some of this list."

"Yeah, it starts out pretty easy. Sharpies, fingers, hairbrush; all the standard stuff most girls try as teenagers."

"And your friends are doing this too? Is it like competition?"

"Sort of, yeah."

Justine had already noticed him twice adjust himself in his chair, his hand dropping below the table. She figured she'd sized him up right. Time to drop the bomb.

"It's actually a group activity," she said, keeping her gaze on his face, looking for a reaction. She caught him mid-sip; he coughed nearly spraying his mouthful of coffee.

"Really?!"

"Yep. Every once in awhile we get together, share what we've found and have some fun." Just one more bomb to drop, she thought. "And as part of the challenge list we also need a guy...to watch. That's #24 I believe."

Jack was speechless. His mind was going a mile-a-minute, re-playing every girl-on-girl-masturbation porn scene he'd ever watched. Now he might get to live it for real!

"So are you in?" she ask causally. "I mean, I'm guessing you've already got quite the hard-on going down there, I'm sure you'd like to watch something fun to finish that off. Right?"

Justine spent the rest of the morning readying things for the Challenge Party. On her way home from the farmers market she picked up a couple bottles of champagne and chardonnay--the parties always included some form of libation to loosen every one up. She tidied up the apartment; mainly the small living room where the action usually took place. The large L-Shaped sofa allowed everyone a comfortable seat and a clear view of each other. There were also the requisite bath towels, as both Justine and her friend Tara had discovered they could squirt.

Getting the group together on a Saturday was a rare occurrence. Tara and Kelly both worked in retail shops, which usually meant they were scheduled to work on weekends. After a string of breakups, Saturday had become the lonely day where Justine wallowed in self-pity trying to figure out how things had gone wrong, yet again.

Then, one Saturday afternoon, everything changed. Her last boyfriend Gary had left a few random things in her apartment. She was cleaning her bathroom and discovered he had left his beard trimmer (he did have a nice beard). She picked it up and tinkered with the settings; flicked it off and on, feeling the buzzing in her hand. She looked up at herself in the mirror and immediately knew what she was going to do.

Thirty minutes later, her now hair covering the bathroom floor, she stood looking at herself in the mirror feeling completely renewed. The beard trimmer--being so much smaller than a typical hair clipper--had made the process rather slow, but it was done; a bold move to be certain, but not out of character given her adventurous personality.

She was also inspired to go to work on her public hair. Her thick natural bush had been both loved and loathed by various partners. It was time for a change. She first started delicately trimming--first a tidy V-Shape, then an 80's landing strip, and then... she put the trimmer down and grabbed her razor. For the first time since she started puberty her pussy was perfectly hairless and smooth as glass.

Before cleaning up the mess she sat down on the bathmat, leaned back against the tub, and buried the vibrating, non-clipping, end of the trimmer against her clit and had one of the best orgasms of her life. And so started her new Saturday ritual.

Sex with her various boyfriends had ranged from comically bad to occasionally fantastic. Her last, Gary, wasn't particularly romantic, or creative in the bedroom, but he did happen to have a rather large dick--certainly the largest cock she'd ever been fucked with. An impressive 9+ inches and most notably: thick. It was Greg that allowed her to realize girth was she craved the most.

The subject of size came up one night while drinking with the girls. Tara and Kelly were always her post-breakup sounding board. Justine lamented that the thing she'd miss most about Gary was his cock. They all laughed and Tara joked that she'd have no problem finding guy to replace him. "I don't know," replied Justine. "Gary was something special. He has big. Like really big."

They started to compare notes about former boyfriends, and their various dick's--shapes and sizes. It seemed that Gary might have been the largest of the bunch. Justine reluctantly admitted that she had started watching big dick videos on Pornhub, and was really turned on by the thought of being completely filled--stretched even. Kelly and Tara had never had had huge boyfriends and it peaked their interest.

Justine's own exploration, down the rabbit hole of Reddit, soon led to several discoveries. One: there was a name for woman who like large dicks--"size queens". (She kind of liked the queen title). Two: it dawned on her that there was a host of household objects that might satisfy her size cravings in a fun and interesting way. This realization spurred more Reddit searches (and more than a few on Pornhub). Eventually she stumbled upon something called the "Size Challenge". It was a list of 100 objects, in roughly ascending sizes, each assigned a point value. For each object you masturbated with you received points, and a bonus if the object went in your ass. (There was even a bonus somehow calculated based on having two or more objects inserted at the same time, but Justine couldn't be bothered with all that math). The Challenge seemed ridiculous, but also fun and kinky, and it mostly certainly made her horny.

She shared the link with Kelly and Tara, and her current score--already having checked off the first ten:

1. One finger
2. Small Sharpie
3. Lipstick
4. End of a toothbrush
5. Candle
6. Two fingers
7. Handle of a large makeup brush
8. Handle of a hairbrush
9. Popsicle
10. Carrot

Certainly none of these were a real challenge, especially after 9-inch-Gary, but she had fun sticking to the list, and more than a few had made it up her ass (she didn't share that with the girls, yet). The popsicle turned out to be a sticky mess which necessitated a shower; thank god for the detachable shower head.

Kelly and Tara got a laugh out of the Challenge and both quickly made their way through the first part of the list. Kelly suggested maybe they make it a group activity. Both Tara and Justine were initially hesitant. The girls all liked to talk about the details of their sex lives, sometimes quite detailed, like the accidental squirt that nearly choked Tara's list boyfriend, or Kelly's newly discovered cum fixation, but Tara and Justine were't so sure about actually getting naked and masturbating in front of each other. Kelly did have a few experiences with a college roommate, which she said admitted were fun, and assured them it wouldn't make anything weird between them. Of course what Kelly hadn't shared was that she and her college roommate had been fucking each other their entire senior year.

And so it was that on a sunny Saturday afternoon Justine found herself tidying the house getting ready for an another round of masturbation with the girls. This was actually be the third time they'd gotten together. The first session was a bit awkward, and they giggled like school girls managing to check off more challenge items. There was a more relaxed atmosphere the second time, and things got really hot when they discovered they all genuinely got off on watching someone else get off. They also witnessed Tara's incredible squirting ability first hand (they could be see why her boyfriend nearly drowned), and Justine also came to learn that with enough pressure, in just the right spot, she too could squirt--it was a wet and messy afternoon.

Today's session held a surprise in store for the other girls. Justine's decision to invite Jack was a spur of the moment addition; she had not told Tara or Kelly. Her rationale was that they all liked being watched, so what was one more set of eyes. Plus, they'd certainly get to watch him get off, and Kelly could indulged in her cum fetish--if she was so inclined.

Kelly and Tara rang the bell at three o'clock. They too had brought champagne, and a shopping bag full of assorted items to be used during the afternoon. Jack had not yet arrived. Justine invited them in and they popped open champagne with giddy girlfriend laughter.

As a pair, Tara and Kelly couldn't look more different. Kelly was a big girl, not overweight, but full-figured. She was the same height as Justine (about 5' 9"), but outweighed her by a solid 40 pounds. Long legs, thick thighs and broad shoulders allowed her to carry that extra weight in a way no one who ever deem fat. Double D' boobs also helped balance out her proportions. She's was comfortable with her body shape and she carried herself well.

Tara looked like a little kid next to Kelly and Justine. She was 5' 2" (barely), and a petite 100 pounds (barely). The only blonde of the group, with Justine and Kelly both having dark brown hair; she was blessed with perpetually perky B cups, and an equally perky smile that gave her the air of a high school cheerleader.

"So I have a little surprise," Justine announced. "I did something a little crazy this morning at the farmer's market. It was a total impulse. I invited another person."

"It's a guy," Justine paused, waiting for their reaction. Their eyes lit up. "His name's Jack, he's really hot. I've seen him around a few times. He caught me sizing up a giant cucumber. It was kind of funny; I was totally embarrassed. I think he knew exactly what I was going to do with it. Anyway, we had some coffee, and told him about the Challenge list. I made up something about needing to have someone watch as part of the challenge. I know it's not really on the list, but I figured it was an easy way to get him interested. And trust me, he was--he had a fucking massive hard-on while I was telling him about us. I'm actually really curious to see how big he is.

"So, are you two ok with that?" she raised her crossed fingers and gave the girls a silly grin.

"Ok, I'm game," said Tara.

"I think he could be useful," Kelly said, her mind already wandering. The thought of a guy cumming on her while she masturbated really turned her on. (In fact it was on her personal challenge list.)

"Whew, good. Ok, well he should be here any minute," Justine said.

Champagne in hand, the girls settled in on the couch and shared the items they'd each brought. They had made more or less similar progress through the list, so the new items would come in handy for everyone. Large vegetables were on the menu today; they had all brought the biggest cucumbers they could find, and Justine picked up a few eggplants that looked rather intimidating. Tara had brought a couple of rather suggestively shaped bathroom products: a girthy can of shaving cream with a nice rounded top, and bottle of shampoo oddly shaped like a giant butt plug (these product designers knew exactly what they were doing).

Kelly shared hers last, waiting for the girls full attention before making a dramatic reveal. She had discovered a dildo company called Bad Dragon, who made all kinds of crazy dildos. Justine and Tara both gasp when Kelly slowly pulled a 14", purple, replica horse cock from her bag.

"Oh, my god! You're crazy," shouted Justine as they all broke out in laugher. "Let me see that thing."

The color somehow made it slightly less obscene, but there was no mistaking what it was supposed to look like. Justine comically smack her palm with it. It was floppy, but also had some heft to it. "I know it's not on the list (thank God), but I thought it would be fun," bubbled Kelly.

At just that moment, the door bell rang. They all jump and broke out in more giggles. Horse-cock in hand, Justine answered the door. The look on Jack's face went from excitement, to terror, and back to excitement as he took in the scene.

"Come on in Jackie-boy. We've got a little surprise for you," Justine said, as she smacked the purple cock into her open palm. The girls again erupted in laughter.

"Ahh, ok? Hi, I'm Jack," he stammered. "I'm not exactly sure what's going on, but nice to meet everyone."

Justine made the introductions and apologized for blindsiding him with the addition of her friends. She explained how the Challenge list had turned into a Saturday ritual for them. Jack clearly didn't mind. He scanned the room, wide-eyed with excitement at the prospect of watching the girls three fuck themselves with large random objects.