A Walk in the Woods
Fluttershy enjoyed being part of Canterlot High's special disciplinary program. That would have surprised most of the students who were outside her circle of friends. She came off as shy and demure and most thought, if anything, she would be kind of a prude.
In actuality, Fluttershy loved sex. While she hadn't yet had full intercourse, that was more due to not yet finding a partner she wanted to be that intimate with. Her friends were nice, and there were certainly more than a few students of any gender at CHS which she found attractive, but she didn't want to risk making things awkward within her circle of friends, and full sex just seemed to her like something she should savor with someone she actually loved.
Everything else, on the other hand, was fair game. Cumming was almost an addiction. She masturbated every morning after she woke up and again before she went to sleep. On days she didn't have school, she usually found time for at least two more sessions. She had an impressive collection of sex toys in a shoebox under her bed. During the previous summer, her parents had gone out of town for a week and Fluttershy hadn't bothered wearing clothes for that entire time, setting increasing personal records for most self-inflicted orgasms in a day, culminating in a grand total of almost 40 in a single 24 hour period.
So, to her, it was a god send that the special disciplinary program was used at CHS. Students who acted up in class, and had chosen to participate in the program, were made to orgasm repeatedly up to a set number determined at the beginning of the semester. Fluttershy had jumped at the chance, although in her usual circumspect way. With it came a new discovery.
She loved being watched. She liked pretending to be shy about stripping naked in class then being restrained and made to orgasm over and over again while her classmates (those who hadn't elected to opt out) watched her. And then, after a few months, she discovered something else she really liked.
Which was why she was currently leading a fairly cute boy named Merry Band into her favorite clearing behind the school. Classes were over for the day, and she had invited him to join her for a walk in the woods.
Of course, the poor boy had no idea what he was really there for.
“Um, thanks for inviting me out here, Fluttershy,” Merry said as she led him over to a log in the middle of the clearing. “It's... nice.”
Fluttershy gave him a smile. He was so adorable. Slender and fresh-faced, with tousled blonde hair and gorgeous blue eyes. He was dressed in a T-shirt and jeans. Fluttershy cast her eyes over him, and noted with delight the slightly awkward bulge in his pants. Boys were so predictable. And she loved taking advantage of that.
She sat down on the ground, leaning up against the log and patted the area next to her. “Come sit down. Take a minute to listen to the forest. I love doing that out here.”
Merry swallowed and nodded. He sat down next to her and took a deep breath. “Smells nice out here.”
Fluttershy leaned forward, pressing herself up against his arm. The boy glanced down and blinked at the sight of her cleavage pushing against the neckline of her shirt. He blushed and tried to act casual. Fluttershy closed her eyes and inhaled deeply.
“You smell nice,” she said, as her eyes reopened.
“Um.. thanks?” Merry's voice cracked slightly. Fluttershy looked at him and smiled again.
“Do you know why I asked you out here, Merry?”
“N-not really. To be honest, I didn't think you knew I existed before today.”
“Oh, I noticed you, all right,” Fluttershy said with a soft giggle. “I saw you earlier today.”
“Huh?”
Flutteshy leaned in closer, pressing herself up to him. She whispered into his ear. “I saw you watching me through the window of the class room from out in the hall.”
Merry swallowed again. “Um... I... uh... I just --”
“Watched me cum again and again in front of the whole class?” Fluttershy finished. Merry started to turn his head, but she grabbed his chin, keeping it in place so she could still whisper into his ear. “I know you watched, little boy. You watched my naked body writhe and twitch and cum as I rode that sybian on Ms. Harshwinny's desk. You watched my breasts bounce and my hips rock over and over again as I tried to keep quiet while I came... and came... and caaaaaaaaaaaaame.”
Merry's eyes were wide and he was looking at her out of the corner of them. “I... I mean...”
“You watched,” Fluttershy's voice was low and sensual. “You dirty, dirty boy. Even though you opted out, you still wanted to watch.”
“It wasn't my idea!” Merry blurted out. “My parents didn't want me to participate!”
“Ohhhh,” Fluttershy released his chin and gave him a naughty smile. “So you have to perv on your classmates in secret, huh?”
“Yes! I mean, no! I mean... yes, I watched, but I just... you're so pretty!”
Fluttershy blinked. “You think I'm pretty?”
Merry swallowed again, and nodded. “I think you're the prettiest girl in school.”
His breath rushed out of his lungs as Fluttershy enveloped him in a hug that even Pinkie Pie would have been impressed with. “Thank you!”
Merry's mind went slightly blank as the pinkness and softness and the smells of nature surrounded him. After a few moments, he realized the hug had finished...
… and Fluttershy's hand was on his thigh. He looked at the hand then back up to Fluttershy's face. Which held a very dangerous expression.
“So,” Fluttershy began, her hand gently rubbing up and down his jeans-clad thigh. “Did you get to take care of things after I was done?”
Merry was so distracted by the feeling of her fingers brushing his leg that he lost track of the conversation. “What?”
Fluttershy leaned in closer and whispered into his ear. “Did you go and let aaaaaaaall that nasty boyjuice out of your poor balls? You watched me for such a long time. It must have been boiling in there.”
“Well...uh...” Merry's face was bright red. “I really... um... that is... I didn't exactly have time to...”
“Ohhhh, you poor thing!” Fluttershy cooed. “All that hot, sticky boyjuice pent up in there with nowhere to go! That's not good. Let me see.”
Merry yelped as the hand on his thigh moved squarely to his crotch. Fluttershy gently squeezed the area, noting in satisfaction the hardness she encountered there. This was one of her favorite things to do. Find a CHS student who wasn't on the release program, but DID watch as other students were made to cum in class, bring them out here...
… and play.
“You're so hard.” Fluttershy looked directly into Merry's eyes. “And your poor balls feel so full.”
She squeezed again, causing a strangled cry from Merry.
“Oh, we need to do something about that,” Fluttershy said.
“um... no, that's... that's okay,” Merry gasped. He looked at Fluttershy who withdrew her hand and was looking at him with a forlorn expression.
“Are you sure?” she asked. “You look so uncomfortable and I'm sure it's awkward to walk. I don't mind helping you.”
“Y-you don't?”
Fluttershy leaned back against the log, spread her legs and gestured to Merry. “Come here.”
Merry blinked. Fluttershy's skirt was draped in such a way that nothing could be seen, but the general effect was both enticing and a little intimidating.
“Come. Here.” Her voice was harder, demanding.
Merry swallowed again, then slid over, sitting down between her legs, his back to her. Fluttershy's arms encircled his waist and she kissed him gently on the cheek.
“Now, be a good boy, and let Mama Fluttershy help you get all that nasty white stuff out of your poor swollen balls. You really should have taken care of it long before now, you silly thing.”
Fluttershy's hands went to the button of his jeans. He shudderd as she popped it open and began tugging the zipper down.
“Um... are you s-sure about this?” he stammered.
Fluttershy's hand slid into his pants and cupped him through his underwear. She squeezed, causing him to let out a squeak. His testicles felt firm and heavy. The squeeze sent an odd wave of pain through his gut.
“Oh, these are much too full. You poor thing, you have blue balls. That's not good. Mama's going to have to take care of this right away.”
She brought her other hand up and quickly freed Merry's rigid cock and swollen balls from his underwear. He moaned as she did so, gently caressing him and causing the boy to shiver.
“There we go,” Futtershy cooed. “Doesn't that feel better without your undies in the way.”
“I... guess? I mean, I just--”
“Shhhh,” Fluttershy shhhh'ed. “Mama's going to take care of her good boy. You do want to be a good boy for Mama, don't you?”
She gently squeezed his bloated nuts with one hand while giving his cock a firm but light stroke. Merry gasped and his hips bucked.
“See? Mama knows what you need,” Fluttershy cooed in his ear. “Mama does this for all the good boys who don't get to release at school.”
“All?” Merry gasped. Fluttershy was still softly stroking him, teasing the head a bit before moving her hand down his rigid shaft. He stared straight ahead, afraid she'd stop if he turned to look at her. He felt her breath in his ear again.
“Mmm-hmmm. Mama takes care of the good girls too. There's soooo many of you who see all the naughty naughty things that go on all day. It's not fair that you don't get to relieve some of that pressure. So Mama has to do this for you.”
The hand around his cock left for a moment, as Fluttershy licked her palm and went back to stroking him. Merry bit his lip. It felt so good and he fought to keep from moaning.
“It's okay, sweet boy,” said Fluttershy. “Let Mama know how good it feels. Good boys don't try to hide their feelings from Mama. Let it out. Come on... be a good boy and tell Mama how it feels.”
“It feels good,” Merry whispered. “But it kinda hurts too...”
“That's because you let your balls get too full.” Fluttershy's other hand gently squeezed them again, causing Merry to moan. “Good boys don't let that happen. Good boys know all that boyjuice has to be let out every so often. You're a good boy, aren't you?”
“Yes,” Merry said. The sensations were overwhelming him and he felt like his testicles were clenching up.
Fluttershy stopped stroking. “Yes, what?” she said, her voice hard.
“Yes... Mama?”
The stroking and fondling resumed. “That's my good boy.”
Suddenly, the speed of her stroking increased and her grip on his balls tightened. Merry gasped again as the sensations became more intense.
“We need to get it out of you, my good boy,” Fluttershy was saying. Her voice was raspy. “You've held onto it much too long and it needs to get out. I can feel it in your poor balls. Your boyjuice wants to come out. It needs to come out.”
Merry cried out as he felt his balls clench harder and the tingling sensation at his tip that indicated something was coming. Fluttershy kept stroking. Kept fondling. Kept whispering in his ear, encouraging him to let go.
“Let go. It needs to come out. You know it needs to come out. You know Mama's only doing what's best for you, don't you.”
“Yes, Mama!” The words came out in a rush of air.
“Then cum. Cum for Mama. Let all that nasty stuff out. You've been a good boy so far, and good boys do what Mama says. Good boys don't keep all their juice inside where it can hurt them. Cum for me. Cum for Mama. Cum for Mama right now!”
Merry practically screamed as all the semen he'd kept pent up in his balls rocketed out of his penis, spurting out onto the ground. Tears rolled down his cheeks as the pressure caused his orgasm to send conflicting signals of pleasure and pain to his brain. His hips rocked, but Fluttershy let go of his balls and held him close, all while pointing his cock away from them. All the while, she kept encouraging him.
“Yes, gooood boy! Keep squirting it all out. There's so much! What a good boy, giving Mama all this boyjuice! Keep going. Don't stop. Mama wants to be sure it all comes out. Oh, such a sweet boy. Such a good boy.”
“Aaghghghhhgh!” Merry cried. He felt like he had been cumming for hours, that it would never stop. But eventually, it did and he collapsed back against Fluttershy, who kissed him on the cheek again and gently stroked his hair.
“Oh, so much backed up in there. We may need to do this more often. Mama can't have her boy getting so pent up. It's not healthy. Good boys need to be milked every day to keep that from happening.”
She slid her hand back down to his balls and gently cupped them again. Unseen by Merry, she gave and evil little smirk. “Oh, my!”
“Huh?” Merry grunted, still dazed.
“There's still some in there,” Fluttershy said in a mock concerned voice. “Well, we can't have that. We need to get all of it out.”
Merry let out a sharp moan as Fluttershy began stroking him again, bringing him back to full hardness.
“Wait,” he gasped. The sensations were more intense as his sensitive penis was still recovering from the pleasure he had just felt.
“No, we can't wait,” Fluttershy said firmly, increasing her speed. “If we do, it will just take longer. Mama's going to get all your boyjuice out of you so you can have a good night's sleep tonight. Now just relax and let it out.”
Waves of pleasure raced through Merry Band as Fluttershy mercilessly stroked his cock. He writhed against her and his moans became louder. Suddenly, she clapped her free hand over his mouth and wrapped her legs around his own, holding him in place.
“Shhhhh, good boy. Mama's here. But we can't have you make too much noise. I mean, who knows who might hear us. The faculty parking lot is right over there.” She let out a theatrical gasp. “What if Principal Celestia or Vice Principal Luna hear you and investigate. Oh my, they could find us here and see you like this! Your poor cock in my hand as I work to relieve all that pressure in your balls. What would they say? They'd be sooooo angry.”
Merry's moans were muffled as Fluttershy craned her head to get her lips as close to his ear as possible.
“Oh, but what if? What if they joined in? What if they realized how pent up you are and decided to help Mama out. Oooh, can you imagine? They might get down here and help me. Imagine! Principal Celestia stroking this good... boy... cock...”
Fluttershy smiled as her emphasis caused Merry to practically scream into her hand. She kept teasing, kept stroking, kept talking.
“And Vice Principal Luna could be fondling these sweet little balls of yours. And all that time, I'll be right here, holding you, making you feel safe, telling you what a good, good boy you are. And who knows?”
She removed her hand from his mouth and pulled him closer as she felt his cock begin to tense. “Maybe all three of us will use our mouths on your lovely good boy cock.”
That was all it took to drive Merry over the edge and cause him to cry out as a second orgasm took him. His cock throbbed and pulsed, but only a small amount of semen came out of him, with less force than his first. He tensed, then collapsed against Fluttershy, eyes closed, breathing heavily.
“Good boy,” she whispered, then kissed his cheek again. “That's Mama's good boy.”
She snaked her hand down and cradled his balls again, gentler than last time. “Oh dear, I think there's still some more in there.”
“Wha?” Merry's eyes opened and he looked at her. “No, please... there isn't any more AHHH!”
Fluttershy relaxed her hand from squeezing his balls. “Hush. Mama knows best. There's more in there and I want it all.”
She started slowly stroking him in time with her words. “Every. Last. Drop.”
She wrapped her free arm around him, locked her legs and began fiercely stroking him, using his last load as lubricant. Merry moaned and nearly cried as a new mix of pleasure and pain enveloped him.
“Please... Please... no more... Please...” he whimpered.
“Please, what?” Fluttershy asked, not letting up.
“Please... Mama. Please... I don't have any more...”
“Oh, I think you do. And all your boyjuice belongs to Mama now. Understand?”
Merry nodded his head frantically. “Yes, Mama.”
“And you're going to give your boyjuice to Mama whenever she wants it, aren't you?”
“Y-yes, Mama.”
Fluttershy smiled. “That's my good boy. Now, give Mama your last load. Give it to me and it'll all be over.”
“I'm trying, Mama!”
She could tell he was. She had milked so many boys like him before. They tried so hard to cum again, but it was so hard when they got to this point. Their bodies just refused to cooperate. Fortunately, she knew just the thing to encourage him.
“Would you like to know a secret, my good boy?”
Merry moaned again in response. Fluttershy got close to his ear again.
“Mama's not wearing any panties.”
Merry's head turned, surprise on his face. “What?”
Fluttershy smiled and took one of his hands. “Mmm-hmm. See?”
She dragged his hand under her skirt and bent her knees so she could push her pussy up against his fingertips. She gasped and cooed as he brushed up against her clit.
“Mama stopped wearing panties a looooog time ago. Doesn't it feel good?”
Merry swallowed. “Y-yes, Mama.”
“I bet you'd like to play with Mama's kitty, wouldn't you?”
“Yes, Mama.”
Fluttershy resumed stroking Merry's cock. She kept up a steady pace, and Merry felt the pressure building again. “Well, if you keep being a good boy, and listen to Mama, and give her all your boyjuice, maybe one day, Mama will let you play with her and make her cum. Would you like that? Would you like to help Mama cum?”
“Yes, Mama!” Merry cried.
“Would you like to feel Mama squeezing your fingers as you thrust them in and out? Would you like to feel her quiver on your tongue as you lick her little kitty to climax?”
“Oh, god, yes, Mama!”
Fluttershy's voice lowered as she moved in for the kill. “You want to fuck Mama, don't you? You want Mama to moan and writhe as your thick good boy cock pounds her pussy over and over again. You want Mama on all fours in front of you, screaming in pleasure as you grab her ass and --”
Fluttershy slid Merry's hand out from under her skirt, wrapped her arm around his waist again and started thrusting her hips up against his ass as she pounded his cock.
“THRUST it in and out of Mama! That's what you want isn't it? Or maybe you want Mama to do that to you?”
Merry let out an inarticulate moan. The pressure was unbearable but he wasn't able to get over the edge to get the relief he needed. Fluttershy kept rocking her hips into his back.
“You want Mama to fuck you, don't you? You want Mama to put on a big beautiful strap on and fuck! You! Hard! Don't! You?!”
“YES, MAMA, YES!” Merry yelped.
“Then CUM!” Fluttershy demanded. “Give me your cum! All of it! Right now! Mama wants every single bit you have! And, maybe, Mama will give you what you know you really want! DO IT!”
“MAMAAAAAAAA!” Merry's whole body convulsed and twitched as he came. There was very little actual fluid but Merry's brain was practically exploding with pleasure. He finally collapsed against Fluttershy, breathing heavily. Fluttershy put his cock and balls back in his underwear and zipped up his pants. She hugged him from behind and kissed the back of his head.
“That's my good boy. Just rest now. Mama's got you. You don't need to worry about anything.”
“Th-thank you,” murmured Merry.
“'Thank you,' what?” Fluttershy said, putting an edge on her voice.
“Thank you, Mama.” Merry corrected, before his eyes closed and he fell asleep.
Fluttershy smiled. Another one for her collection. And maybe, one day, she really would give him the fucking he so desired. That they all desired.
She made herself comfortable. After all, Mama couldn't let her boy wake up all alone, could she?
“Good boy.”