Title was supposed to be written as "Diapered and Emasculated," oops lol. This story (and eventually others) can also be seen on my Wattpad! https://www.wattpad.com/user/blushingginger

This will be posted as 8 separate Chapters here (Reddit limits to post size)

Chapter 1 – Courtship and Lust

Ron was elated. He had never been this close before. His social ineptitude and awkward demeanor had long prohibited him from any romantic pursuits or “adult” late night activities with women. But he had hit it off so well with Kimberly when he met her at his college’s board game night. He found it easier to relate to her because she was nerdy, and he was able to talk with her about things that would turn other women off immediately. If you went up to most girls and started talking about Nintendo, those girls normally looked down on you as some kind of childish loser and wrote you off as a potential romantic interest. But because Kim and Ron shared that common interest, he could lean on those things to find things to chat with her about, where otherwise he would be stumped.

Now he was sitting across from her outside a Subway, with the sun shining down on her brown hair and lighting up her deep brown eyes, which were inexplicably smiling at him. This had never happened before. He was usually too shy, too submissive and too weak-willed to find himself in this position. She was laughing at his corny jokes, she was giving him looks that could only mean good things to come, and she was asking him more questions about himself than any girl had ever asked before. In his excitement in answering her questions, he almost forgot to make sure he also asked her questions about herself to show he was interested in her too, but it was clear things were going well regardless.

She was so attractive it drove him mad. Her wide, ample hips were outlined by the black yoga pants she was wearing, which very flatteringly revealed the curve of her behind. She leaned forward in interest, bringing her eyes closer to his. Her pupils were deep pools that were easy to get lost in. Leaning in revealed more of the top of her chest to him, her bountiful bosom peering out from under her shirt. Her eyes were intense, and her hair a dark river over her shoulders.

Kim squinted her eyes in a chirp of laughter at Ron’s joke, opening them again to look right into his. Ron’s leg did a nervous twitch, and he became subconsciously aware of the fact that he was going to have to hit the bathroom at some point. He smiled back at Kim, trying not to seem nervous. Ron had the feeling that she was playing up how funny his joke was just a little bit, but he didn’t mind. She was being nice to him.

Kim’s lips parted as she prodded him. “So now you’re staying in the Donner Hall dorm this semester?”

Ron nodded vigorously. “Yeah, I couldn’t stand the guys in my old dorm. And I also couldn’t stand having to share a room with that one guy who always left a mess everywhere.”

Kim’s head perked up in interest. “Oh? Do you have your own room to yourself in Donner?”

Ron cracked a smile. He liked where this was going. “Yeah, the rooms all share a common area, but I don’t have to share the bedroom itself or bunk with anyone. I really like having my own private area.” He raised an eyebrow at her. “You should come see it for yourself.”

Kim cracked a smile herself. “You know what? I would love to! In fact, I think I’ve had enough sun for one day. Maybe we should head there right now.”

Ron threw out his trash and sauntered towards the dorms, Kim by his side and a new confidence burning in his chest. But that confidence soon started to turn into self-doubt. Things were going too well. Were his expectations for what was about to happen too high? Did he have what it takes to secure his conquest of this lovely girl? Was he setting himself up for embarrassment and failure? But he shrugged off those doubts. Now was the not the time to second guess how well things were going. Now was the time to take his shot with the attractive and amicable fellow student who presently seemed very interested in following him to his room.

He blushed a little as he waved to his dorm-mates in the common room, as they saw the girl following behind him and gave him knowing looks. Kim waved cheerfully to them, not seeming at all shy or self-conscious about their amused expressions. Ron closed the door behind himself and Kim. He had to remind himself to take a breath. He was hyping himself up a little too much if he wanted to perform properly.

“Well, here it is! My royal quarters.” He said jovially.

Without warning, Kim picked up a pillow from his bed. “I bow to no king!” she blurted, before striking him across the head with the pillow and then bursting into a fit of laughter.

Ron laughed as well and grabbed another pillow. “No fair, you had the element of surprise!” He complained as he swung wildly at her.

“Royal my ass!” Kim cried, doubling down on her feathery assault.

She slapped him in the stomach with a strong blow that almost caused him to lose control of his bladder, which he had forgot he’d been holding. He laughed and swung back in turn. He got close to her, wrapped his arms around her, and brought her down onto the bed in a fit of giggles.

She looked up at him innocently and put a finger to her lips. "Looks like you've got the best of me! Now what are you going to do with me?”

Ron felt his heart race at Kimberly’s words. She was daring him to make a move. He took a step closer and gripped the bottom of her shirt. She smiled and bit her lip invitingly. Trying to hide his nervousness, Ron pulled the shirt upwards over her head, revealing her smooth stomach and lacy bra. Ron tossed the shirt aside and paused to admire her feminine figure sprawled out leisurely on his bed, before leaning over and kissing her. She closed her eyes, gripped his head, and kissed him back passionately.

As they kissed, Kimberly slid her yoga pants and panties down her smooth legs, while Ron ran his hands up and down her sides. She smiled at him slyly. “Your turn, big guy. Go on, take your shirt off. Make yourself comfortable.”

Ron grinned and yanked his shirt off, tossing it over his head onto the floor. He then leaned back in to kiss Kimberly again, removing her bra as he did so, then fondling her breasts in his hands. At one point he moved his mouth from her lips to her neck and started gently nibbling it, causing her to chuckle in delight. Ron was enjoying the feeling of Kimberly’s skin against his own.

At length, Kimberly put her hands on Ron’s chest and pushed him back a little, looking right into his eyes. “What are you waiting for, hotshot? Take the rest of it off.” She gave him a teasing look. “You aren’t … shy, are you? I’m sure you have no reason to be…”

That last sentence seemed to be merely playful banter, but all the same Ron couldn’t help but feel a slight bit of nervousness come over him. He shook that feeling off and resolutely stood up from the bed. He looked down, swiftly slid his pants and underwear off in one motion, kicked them away, and then walked over to the bed, looking up at Kimberly’s face and making to embrace her again.

Kimberly looked down at Ron’s crotch and her mouth opened slightly, her cheeks growing red. She put a hand over her mouth and burst into laughter, using her other hand to push him away slightly. As she laughed, she looked back up at Ron. Pity had replaced the lust in her eyes. She looked back down at his crotch and continued laughing.

Ron felt embarrassed and unsure what to do or how to react. He sat on the edge of the bed next to her, starting to feel subconscious about his nudity. He asked, “What’s so funny?”

Kimberly managed to catch her breath after laughing so hard. She sputtered “I'm sorry, dude. I just kind of expected you to have a normal-sized dick. It's just really hard to continue seeing you as a man after seeing your little baby penis. No woman could ever feel that thing inside her. I’m not even sure you could even get it in!"

She continued to laugh cheerfully, not seeming to care that her laughter was delivering a crushing blow to Ron’s manhood. Ron got up sheepishly and walked over to where his pants were, starting to put them on.

Kimberly watched him, continuing to emasculate him with her mocking words. “You really had me going. I thought you were going to be some kind of dominant alpha guy. I wasn’t expecting you to have a two-inch dick. I can't believe I was going to sleep with you!” Kimberly, with mocking eyes and pouty lips, held up her hand and performed a pinching motion with two fingers, mimicking the size of his inadequate dick, then burst into another fit of giggling.

Ron felt a mixture of embarrassment, anger and pain as Kimberly laid into him. “It’s not funny. I can’t help how big I am. You don’t have to be so hurtful about it…”

Kimberly snorted with a smirk on her face. “What did you expect, Ron? Did you not know you had a tiny widdle baby penis …” Her eyes had wandered around the room and fallen upon a half-open drawer in his closet.” “… Uh, Ron? What's that?"

Ron was slightly taken aback by her change of tone. He followed her gaze and his heart skipped a beat. “Uhhhhh,” he stammered, breaking out into a sweat, cursing himself for not having kept that drawer closed.

Without waiting for a response, Kimberly yanked the drawer wide open and pulled out a blue crinkly package. A package of XL Goodnites Pull-Up diapers. Kimberly snorted, putting her hand to her mouth for another fit of laughter, looking straight through Ron with even more pity than before.

For his entire life, Ron had been a bedwetter. His bedwetting often worsened with stress, but regardless, it was always there. There had been periods off and on where he had been able to stay dry the entire night, but those periods never lasted long. Most mornings started with him waking up in a wet diaper, feeling like a pathetic toddler. And that’s what he wore to bed. Diapers. He wore diapers to bed like a fucking baby. It was his most shameful secret. After a while, he had given up on any hopes of growing out of his infantile habits and resigned himself to the fact that he was going to be wearing diapers to bed for the foreseeable future.

And just now, poking out of the open drawer he’d never closed (how on Earth could he have predicted he would be bringing a girl over to his room?) were his XL Goodnites training pants for bedwetters. For some reason he had stuck with the same Pull-Ups his parents had always bought him before he went off to college. In his mind he convinced himself that if he kept buying the Goodnites rather than the Depends, people were less likely to think they might be for him. And the Goodnites were more familiar. But now that he was caught, the childish designs were just making the situation even more humiliating.

As Kimberly laughed, Ron wallowed in a wave of humiliation and self-loathing, his face beet-red as he stood frozen and speechless before Kim’s mocking gaze. He stammered out “Y- Y- You don’t understand. They’re not for me…”

Kim scoffed. “As if! You’re a fucking bedwetter! It makes sense since you have such a little baby dick! Awwww, does the little baby have a tiny bladder to go with his tiny pee pee?” She held the package of Pull-Ups aloft and pretended to suck her thumb.

Ron grit his teeth and his eyes started watering. “Stop it!” he shouted.

“Awwww is the widdle baby gonna cry? Does baby need his liddle binky?” she continued her thumb sucking routine. “The big baby is sad because his crush found out he’s not potty trained yet! Poor baby!”

“I just need them at night! It’s not a big deal!” Ron shouted, tears in his eyes.

“Ohhh my, why didn’t you say so? That’s soooo much better!” Kimberly cooed in faux admiration. “You are such a big boy after all! Well,” she looked at him snarkily, “maybe not in every way…”

Ron’s hands were trembling. “Stop saying that!” he cried. Then he froze.

He felt a weird sense of warmth running down his leg that didn’t belong there. It took him a second to process what was happening. Then his eyes opened wide with horror. He jerked his head down.

He was wetting himself.