“What the hell do you mean? How and… isn't that ridiculous!? They're chips!”
Kevin stood up to Monica, who he was assigned to by his frat house. Kevin wasn't a big tough guy, but he's reasonable. Light brown hair and a soft, European face. Skinny but fit, a typical college boy who is healthy but doesn't hit the gym hard but wants to party. With guys and with girls.
Each of the pledges were given a sister from another house to work with and serve for a day. Each sister had their own set of rules that the pledges were supposed to follow and Kevin played along at first. Closing the door gently, helping her down gently, putting away some papers gently. But then he thought it was stupid when he was told to eat chips gently. They were chips!? How was he supposed to chew chips gently?
He stuck his hand in the bag as she walked up to him. He raised his brow at Monica in her yoga pants and tight t-shirt. When he first saw her, he felt lucky to get a day with her. She was undoubtedly sexy. She had this quiet but compelling demeanor and a killer body. When she explained that around her, he had to do everything gently, he smiled. It was fun and his mind went to some fun things he could do gently with her and that body. But he was getting tired of how everything had to be gentle.
“Closing the door gently I get… getting it on gently… I get that too.” They haven't done anything yet but he wanted to plant the seeds. He tried to notice her reaction but didn't catch any reaction our of her.
“...But chips0? They're chips!” Kevin chewed confidently to prove a point.
Monica approached Kevin in his jean shorts and he looked down at her. She stared in front of him and made him squirm a little. He remembered that she needs to give his fraternity her approval.
“I don't mean to be disrespectful… but it's just-”
Monica swung her foot out in an arch, slamming it hard into Kevin's balls. Kevin's eyes bugged out as he dropped the chips to the floor and pulled his hands in to clamp over his testicles.
“Ohhh! My balls, holy shiiiit…ahhh… oooo my nuts what the fuuuck!?” Kevin cried out, doubling over. He collapsed to the floor and lifted his ass into the air and shook in pain. A guttural, sick moan escaped his lips as they fluttered against the floor.
“If you aren't gentle, then I won't be either.”
“Unnnn… nuts, my nuts…ooo you kicked them sooo hard…” Kevin croaked. His hands cupping his nuts in his jean shorts. Eyes were wet and it felt like his balls were obliterated. He did not expect this at all. His stomach churned as he rocked in the fetal position.
“Yes. Your poor, poor nuts… try not to puke, okay?”
“Mmphhh… f-fuck… you…”
Monica laughed and kneeled next to Kevin, who was writhing like a fish out of water. His face was reddening as the deep guttural agony twisted his balls and guts.
“Mmm…maybe! If you are gentle today. And play along… then I'll fuck you.”
Kevin looked up at Monica, grimacing and breathing hard. He stared at her and swallowed hard before whining and putting his head down, bowing in submission.
Soon, Kevin was able to stand up. He gently picked up the chips he dropped and cleaned up. Gently, Kevin followed Monica and helped her decide on what to watch on TV.
Then, Kevin gently was asked to help Monica pick out some clothes. A thin white blouse, a short pink skirt and knee-high stockings.
“Oh yeah… you'll look really good in that.” Kevin mused. He looked at Monica and thought about how her legs would look. Her breasts pressing against the tight blouse…
“Yeah… I would. But you will!”
Kevin laughed at the joke, but then soon realized Monica wasn't laughing. She was just staring at him and suddenly he shook his head.
“Wait, wait! You want me to wear this! I'm… I'm a dude! A guy! I have a dick and balls!” Kevin exclaimed, grabbing his junk.
“I know. I felt them before.”
Kevin groaned and lifted his junk, massaging his nuts and shaking his head.
“Shut up… I'm not putting this on, Monica. I'm telling you.” Kevin lifted his hands and palms up, smiling disarmingly.
“I'm a guy, I'm not fucking putting this-”
Monica swung her knee up hard and reintroduced Kevin's frat boy balls to his pelvis.
Kevin immediately gasped out. His knees clicked together and bent over, trying to cry out but there was no air in his lungs. He quickly collapsed to the familiar position, bowing to Monica.
“That wasn't a very gentle response… Kevin, Kevin, Kevin. Do you hear me?”
“...uuuuaaahh… awwwhh… stoooop… stop hitting me in the nuts…”
His breathing was ragged and brutal. His eyes were watering and he couldn't look up. The pain was so overwhelming that it made his sight pounding and his head aching. His forehead was pressed against the ground as he held his sore, swelling testicles that were the size of walnuts.
“Hmhmm! No! I'm not. That's the gimmick, Kevin. You are either gentle and subservient. Or your balls get crushed. Now… get off your knees you little bitch and put on this dress. Trust me. You'll look really good… and every man that puts this on, comes out better. And more gentle… and less of a testosterone fueled, misogynistic pig. Now! Look at me!” Monica commanded with a new voice.
Kevin looked up, face red and eyes watering. He was shivering in pain and gritting his teeth.
“Wear it… gently… so your balls can have a gentle rest of the day, cutie.” Monica smiled, tilting her smile as she ended. Her breasts shook as she moved and Kevin grimaced. His head turned down and he let out a wet guttural cough.
One hour later
Kevin put on a bright smile as he poses for Monica. His smile was forced as he turned in the pink dress. His thighs were visible under the dress as he twirled in it. The blouse showed off his flat stomach and light treasure trail going down to the pink dress. Monica smiled as she watched.
“Beautiful… so good.”
Then, Kevin shoved his ass out, showing off his body. Knee high stockings, gap of clear skin that went up to under his dress. Then he bent over, the pouch of manhood peaking out, showing himself off. Then, standing up he felt a rush of energy.
He hated this at first. And had to force himself to play along but there really was something to this, he thought. Seeing himself in the mirror, he felt conflicted at first. His immediate thought was… wow, he looked hot. He owned the outfit. He never saw himself in this light but he did have the body and face for it.
He smiled at Monica as she approached him.
“You know, I actually kinda–”
“You look good. Hot even. But you weren't posing very gently.”
Monica swung her foot out up between his legs and Kevin's eyes twitched. His balls were pancaked between his legs for the third time today.
“Ooo! Nooo, not agaaaiinnn…”
Kevin collapsed to the ground and held his balls under his skirt. He rolled on the ground, eyes tearing up as he groaned out loudly.
“Fuck! My nuts, aaaghh! Why! Stop… stop kicking me in my nuts… it hurts so fucking bad…”
“A gentle person wouldn't show off their ass and equipment like that. You have a long way to go before you understand what it means to be gentle.”
Kevin's groaning was strained and his voice was even more wobbly “...nnnnn… you're gunna b-break my balls…” Kevin started sobbing. His fingers wrapping around his bruised testicles, holding them tight to his body.
“Why… why are you crushing them…my poor nuts.. “
“Because you're a man. It's fun to do and it's how you learn. Doesn't this feel terrible? Aren't you sick to your stomach? Don't you just want his pain to end?”
“Mmph… pp-please… just stop kicking me in the balls…” tears fell to the floor. He couldn't take it anymore. The pain was just too much.
“Then… be a good boy in a dress… and be better. Be beautiful… be gentle :)”