Note: This story was dynamically reformatted for online reading convenience. Author: Honey Moon Title: Cherry Picking Time Part: 01 Keywords: lesbian, first time, gg, loli, cucumber Cherry Picking Time Part 01 By Honey Moon Missy looked nervously at Annie, her best friend in the whole wide world, and took a deep breath. "Are you sure you want to do this?" she asked as she stared at the cucumber she held. "It's gonna hurt, I just know it will." The elfin featured girl with the short curly red hair sighed. "You are such a big baby." The eleven year old slipped her jeans down thin but well toned legs, and kicked them off to join the general mess of clothing strewn around her room. With a wicked grin, she then hooked her thumbs under the waistband of her pink Hello Kitty panties and eased them slowly down. "I'm going first, just to show you how easy it'll be." Missy couldn't help staring between her friend's legs. For some reason seeing Annie exposed like this made her heart pound. "Um, are you really, really sure? I, uh, I don't want to accidentally turn into a lesbian or something!" "Get real, Missy! Anyone who drools over Justin Bieber like you do isn't a lesbian." "Good!" "Now bisexual, that's a whole other story!" "Annie! don't say things like that!" "Oh shut up!" she handed a small, nearly empty bottle to her partner in crime. "Use some of this. I stole it from my aunt's apartment last time I visited her. She had a new bottle, and she's so forgetful she'll just think she finished this one up. Too bad I couldn't risk swiping one of her dildos though. There's no way she wouldn't miss it if one of those bad boys disappeared!" Missy peered at the bottle. "Astroglide, what's that?" "Whatta ya think?" Annie settled back on her bed and spread her legs wider. "It's to make things really slippery. It'll be more comfortable that way." She giggled. "Not that I ain't kinda slippery already down there. Just put a couple drops on the business end. Don't get it on your fingers, or you'll have trouble holding onto Mister Cucumber!" "Well, okay." Missy carefully dripped a couple drops of the fluid onto the end of the vegetable. "It's all ready. Are you sure about this?" "Sure I'm sure! I'm not gonna chicken out like a certain big baby I know. Now let 'er rip!" Although she put on a convincing show of confidence, Annie closed her eyes and bit her lower lip as Missy nervously brought the cucumber closer to the cleft between her legs. Fingers trembling, Missy gingerly touched her friend's nakedness as she tried to align things properly. The smooth puffy lips felt so warm and damp to her fingertips, and she shuddered at the little gasp Annie made when she had touched her. Missy shifted her weight from foot to foot, embarrassed at feeling the growing warmth between her own legs. "Okay, here goes!" she announced as the rounded end of the cucumber seated into the little opening between those pretty lips. She pushed, and there was only a little resistance as it slid in a couple inches. "Oh!" Annie gasped in happy surprise. "Score one for gymnastics! I guess I broke myself doing a split or something. That didn't hurt at all!" "That's good!" Missy smiled. "Then I don't have to do this any more!" "Uh, no, keep going!" "Annie, you said you just wanted to pop your cherry so it wouldn't hurt when you picked a guy to screw! You're already popped! If we do anything else it'll be full out lesbo stuff!" "Come on Missy, you can't stop now!" Annie's green eyes begged. "I'm your best friend! Don't leave me hangin'! Just push it in and out for a little while, okay? If you do, I, I, I'll treat you to ice-cream later!" Missy was shocked. Annie may be her BFF, but there was one little fact of life that made her a little hard to take at times. The little bitch was really stingy when it came to money. Annie never treated anyone to anything, and would rather walk miles then spend the dollar fifty to jump on the light rail line! "Really, you will actually take out real money and pay for something?" "Yes! We'll go to the Mall, and I'll get you anything you want from Cold Stone Creamery! Come on push it in some more!" "Not a little taste sample." Missy said with a determined look on her face. "You're getting me a Cheesecake Fantasy!" she paused for a second. "And, we're taking the train! I'm not walking eight miles just for some dumb ice cream!" "Anything you want! I swear it!" "Well, okay, but I'll believe it when you pay for the ice cream!" She slid the cucumber farther into her friend. "This is just too weird though." she whispered, as she pulled the slippery cucumber back out a little bit. "Are you sure nobody will ever know?" "Mom's working late, and my brother won't get home for another couple of hours." She let out a gentle sigh as the vegetable moved back into her. "And, I, I certainly ain't tellin' anyone about this! Every girl in school would want you at their sleep overs if this ever got out!" Standing nervously at the foot of the bed, Missy slowly eased the cucumber in and out of her friend's body. She couldn't seem to tear her eyes away from the sight of Annie's little pussy simply devouring the big green Burpless wonder. She was able to get nearly seven inches completely inside before she seemed to hit bottom, and no more would go in. Annie gave a little grunt. "Take it easy! Don't punch my womb with it! I'll need that if I ever want to make babies some day!" "Oh, s-sorry, Annie!" She repositioned her hand so only about five inches of vegetable goodness would go in before her hand ran up against the smooth hairless mound of her friend's sex. "Is that better?" "Oh damn, fuck and shit, its better then better! It's great!" The slippery green skin of the cucumber gleamed as Missy found a nice gentle rhythm. Annie was sort of squirming around now, and breathing like she just ran ten laps around the track at school. The lanky blonde's blue eyes opened wide as her friend struggled out of her tee-shirt. She couldn't help noticing how firm and big the nipples looked on the perfect little cones of Annie's budding breasts. "You're gonna need a bra soon." She said softly as she openly stared. "No wonder all the boys won't leave you alone!" "Not just me." Annie said breathlessly, as she watched her friend stare at her nakedness. "Don't think I haven't noticed how my brother follows you everywhere, Little Miss Training Bra!" "He does not!" Missy's face turned a rather pretty shade of pink. "Does he? Besides, it's not my fault I'm growing a little faster then you!" she proudly thrust out her chest, showing off the modest promise of things to come. "That's why we gotta get ready!" the prone girl gasped as she teased her nipples between index finger and thumb. "I, I want the first time with a real live guy to feel great!" "So, so do I." Missy gasped as her free hand wandered over her body and slipped up under her skirt. A fingertip slipped up along her leg, and sneakily hooked the crotch of her panties and tugged it a bit to the side. The blonde sighed as she touched herself. Annie was really getting into this, and that was just something too hot to see without getting all wet and nasty! "W-What was that about lesbo stuff?" Annie asked softly as she stared up at her pretty friend. "Shut up!" Snatching her hand from between her thighs, she wiped the moisture off on her butt as she kept on pumping the cucumber in and out of Annie. It looked so exciting to see how the inner lips sort of pulled out a little each time the wet and glistening vegetable withdrew! "Missy, c-could you, could you, uh, pretty please?" "Could I what?" "Rub my clitty!" the redhead whimpered. "I'm getting real close! Just rub it a little, okay, and I'll pay for your train ticket too!" "I have my monthly pass." "Please?" There was no doubting the pure and simple need in that one word. "Well, okay. Buy me some fruit juice after the ice cream!" She could see the little pink nub peeking at her. Missy reached gingerly, and touched it with her index finger. Annie let out a little yip, and her hips bucked up from the bed. As the cucumber continued it's endless in and out, she began to gently stroke her fingertips across that pretty little jewel. Annie made happy little mewling sounds that showed her approval. A sudden compulsion overtook the trembling blonde. Never breaking stride with the cucumber, Missy slowly dropped to her knees. She just couldn't seem to stop herself. Annie was her best friend, but she never thought about doing anything like this with her before! Now, she couldn't seem to let the golden opportunity pass without grabbing it! Leaning closer and closer, she moved her empty hand out of the way. After a final second's hesitation, she stuck out her tongue and let it take the place of her fingers. "Oh Missy!" Annie cried at the electric contact. "That's so good!" Practically slamming the cucumber in and out, Missy rapidly swiped her tongue over and around the firm little pebble. Annie tasted a lot like she did, when she licked her own fingers after `petting the kitty' late at night under the covers while listening to Justin Bieber. No, Annie tasted better! She decided not to worry just now about turning into a lesbian. After all, her own big sister was one, and Kelly was really great! Maybe it would be cool to be bisexual. Especially with someone as pretty and nice as Annie! "Oh God!" the redhead cried as she began to sort of bounce her butt on the bed. "Oh shit! I'm gonna die! I'm gonna die in my bed! Don't stop! Please Missy, don't stop now!" Missy didn't stop! Hand pumping, and tongue lashing, it made her so happy to know her friend liked her efforts! Suddenly Annie cried out, and warm liquid spattered her hand and face as her friend writhed like someone in great pain! "You peed on me!" she scolded when Annie finally seemed to return to normal. Well, for what passed as normal with the devious little redhead, anyway. "That's nasty!" "I did not pee! Don't you know anything?" Annie blushed. "That was a squirt! You made me cum so hard I squirted!" she sighed. "It was wonderful!" Missy stared at her. "W-What was it like?" Annie sat up and grinned her most devilish grin." Strip, kiddo. It's your turn to find out!" Missy backed nervously away from the approaching naked redhead. Annie had a strange hungry look in her eyes that was almost scary! "Strip, as in take off all my clothes?" her face flushed at the thought. "I thought I could just take off my panties! Why do you think I wore a skirt after you called last night and talked me into this?" "Fair is fair, Missy." Annie struck a pose. "After all, you're still staring at me!" Annie was right about one thing. She just couldn't help looking at her best friend even if the feral look in her eyes was scary! She was just so pretty and sexy! Missy came up hard against the dresser, and Annie moved in for the kill. "I, I'll take my skirt off too!" she promised as the rather warm and wet cucumber was taken from her hand. "Isn't that enough?" "Nope!" Putting the vegetable on her dresser, Annie reached up with the fingers of both hands outspread in the traditional `groper' stance as seen in lots of the anime she watched. "I've been curious for weeks! I want to see those sweater puppies right now!" she lunged and gave a little squeeze. "Huh?" Feeling like she was going to sink into the floor, Missy gave a half-hearted giggle. "Mom got them at Justice. They're, uh, padded a little bit." "This I gotta see!" Annie began to unbutton her friend's blouse, ignoring the feeble way Missy tried to push her hands away. Once the blouse was out of the way, she eagerly went to work on the pretty polka-dot bra. "Oh look, they come out!" she proclaimed as she removed the padding. After a brief struggle, she had Missy naked from the waist up. "Why you sneaky little bitch!" she whispered with a grin. "I knew it! You ain't any bigger then me!" Grinning sheepishly, Missy let out a sigh. "Mom got me seven of them for my birthday last month. I couldn't say no now, could I?" "Hell no!" Annie held the bra up to her own chest. "Can I borrow them some time? I bet the guys at school will get whiplash if they notice I suddenly got a bit more competitive in the dairy department!" "You aren't mad? "Are you kidding me?" Annie grinned. "After what you just did to me, I don't care if you're secretly am axe murderer!" With a grin of relief, Missy stepped out of her skirt and pulled down her snow white panties. "Well, I'm not a murderer, but I think you meant that as a complement." Annie whistled like the wolf in all those old Warner Brother's cartoons when he sees a pretty girl. "Padding or not girl, you're a hottie!" She reached out again, and this time very gently caressed her friend's gorgeously formed perfect little cones. "Ya know what? This is shaping up to be my best idea yet!" she grinned. "Are you ready to meet Mister Cucumber now?" Gulping dramatically, Missy let Annie led her back to the bed. "You promise not to hurt me, right?" she asked softly as she sat on the perpetually unmade rumpled bedding. "Missy, you are my best friend! Have I ever hurt you before?" "No, no you haven't." a sudden thought entered her mind. "But what if I'm a lesbian now? Maybe I shouldn't let you do it to me! I should just stick to fingers!" With a laugh, Annie went back and snatched up the cucumber. "I wonder." She said thoughtfully "Do you think Justin Bieber is as big as this thing?" The words came out almost by themselves, propelled by single minded fan devotion. "Are you kidding me? I bet his penis is at least two inches longer, and almost twice as fat!" Annie laughed. "Nope, you ain't a lesbian, that's for sure! Now lay back and try to relax." Ever the classic movie fan, Annie went on in her best Bette Davis voice. "Fasten your seatbelts; it's going to be a bumpy night!" Missy couldn't seem to stop trembling as she scooted back on the bed and spread her legs. "I, I think I'm ready." She said softly. "I sort of got all wet when I was, uh, doin' you." "I'll be the judge of that, Goldilocks!" Annie climbed onto the bed with Missy and stared directly between her friend's thighs. The smooth hairless vagina was about the prettiest thing she had ever looked at! "Hmmm, looks like your ready, but I have to check to make sure." Blue eyes opened wide when Missy realized what Annie was up to. "Yes, please check!" she gasped, as the redhead put her face right between her outstretched legs. "Oh Annie, check a whole lot!" This was a bonus, pure and simple! Annie never ever told her friend about just how many times she humped against her pillow, while staring at a picture of Missy in the one piece bathing suit she wore last year. She had joked and teased about Missy being bisexual, Annie knew deep in her own heart that she herself certainly was! She couldn't wait to actually ride a real live cock, but right now, this was the most important thing in the whole wide world to her! Tongue extended, she gently ran it along the pretty little folds of her friend's most female self. "Oh Annie!" the blonde sighed as the gentle tongue seemed to both sooth her, and set her soul on fire! Missy had known her sister's orientation since she had heard the older girl crying out while supposedly staying up all night filling out college applications with her girlfriend Kathy last year. She had secretly cheered her on when she had finally `come out' to mom and dad. Thank goodness they both understood and supported her, and even managed to talk Kathy's parents into letting the lovers share a dorm room while in college. Now Missy finally knew herself how wonderful another girl could make you feel! "Annie, you're the best friend anyone could ever have!" Annie had read quite a bit about it online, and was delighted in how wrong it all was. Missy certainly didn't smell funny or bad between her legs, and the taste? Granted, it was salty and musky, but Annie could swear she could taste just a hint of lemon! Maybe it was because Missy loved V-8 splash, and drank it all the time. No matter, Annie thought she was simply delicious! As she worked, she learned more about what she was doing. It was so fun to hear Missy squeak and squeal every time she paid a bit more attention to her pretty clitty. Missy was going a little wild. Her late night finger activities never made her feel like this! She reached for Annie, and began running her fingers through those adorable red ringlets as she panted and moaned. "Oh Annie, you're the best! I, I love you! Annie, I love you so much!" Her heart seemed to swell within her chest as she heard Missy's words. She wanted to stop and tell her lover that she felt the exact same way, but decided that it would be better to prove it without words. Annie went frantic as she lashed the tip of her tongue against that wonderful little nub! The fingers in her hair began to tug a bit painfully, but she didn't care at all! If the world exploded right then and there, she still wouldn't have stopped making her best friend feel so good! Missy began to cry out. If anyone had heard, they might have thought some poor girl was being killed! Annie had to grab her thighs with both hands to try and hold Missy still as her face was bathed in the delightful proof of her lover's joy! She lapped away happily, as Missy mewled and whimpered from one peek to the next. She had almost forgotten, but Annie grabbed the cucumber as Missy writhed and moaned. It was best to strike while the iron was hot! Pulling her face from that wonderful wetness, she centered the cucumber and swiftly plunged it in! She actually felt resistance give way as she forever claimed her friend's virginity with five hard inches of fresh garden goodness! "Oh my God!" Missy wailed as she was entered for the very first time. It hurt a bit when her hymen tore, but her crazy mixed up body almost exploded as the pain/pleasure forced her into yet another climax! It scared her a little when Annie noticed a bit of blood darkening the green skin of the cucumber, but what scared her more was trying to explain bloody sheets to mom! That was something she hadn't thought about with today's planned activity! Even before she pulled the vegetable from her panting trembling friend, Annie shoved her hand under the girl's butt. "Work with me, Missy!" she said anxiously as she slipped slowly off of the bed. "For God's sake, don't get any on my bed!" A couple hours later, the two friends happily ate their ice cream at the Mall. "I can't believe this!" Missy said with a wicked grin. "You actually paid for something without complaining! This really is a special day!" she giggled. "In more ways then one! Next time though, just buy a ticket. It was embarrassing watching you check all the trashcans for one that still had time left on it!" Annie couldn't help grinning, even though she had to part with some of her jealously guarded savings to buy the ice cream. "Oh shut up! I found one, didn't I?" she laughed. "Missy dear, why don't you sit down?" she patted a hard wooden stool next to her and grinned even wider. "You even stood on the train, even though that cute guy wanted to give you his seat." Missy blushed prettily. "You shut up! I don't want to sit just yet! Did you really have to shove it in so hard? I don't even want to think about sitting until next week!"