NEW WORLD: Semester Three

[NewGuy20]

I know at least a few different people on DD who follow my Ebooks so I thought I'd make a post about a work I just published. I've had a lot of requests for a sequel to the "New World" series and I finally found the time to write it. 

Check out this link for more: 
https://www.amazon.com/dp/B07SQLQB6P

 

Chapter I: Hitched

Mike sighed heavily, sprawled out on the couch and staring at the holographic TV in the living room. Watching a movie had sounded like an entertaining enough distraction when he started it. Now he wasn’t so sure. The protagonist in the film was a tall, athletic woman with her platinum blonde hair tied back in a tight bun. Of course, the hero of the movie was a woman. Big surprise there. The tight, black leather pants she was wearing accentuated her ass but that was about the only thing Mike found entertaining about what he was watching. Biting his lip, he crinkled ever so slightly as he felt his penis starting to get hard, straining against the ridiculous chastity device affixed to his genitals. He was used to that by now.

Lying on his stomach, as Mike shifted his weight, he felt the spongy texture of his warm disposable diaper between his legs. He was wearing only a wet diaper and a short t-shirt: his official uniform at home during the summer break. Sure, he had argued with his mom that he could come and tell her when he needed a change and that he was allowed to wear sweatpants even while living in the freshmen dorms… but his protests went unacknowledged. When he lived at home during high school, his mom almost never allowed him to wear pants. Mike could only conclude that his mom would always see him as a little child regardless of the fact that he was now a college sophomore, not to mention the fact that he was engaged! At first, the idea of getting married made Mike feel like an adult but the more he saw his mother and sisters reactions to the news, the more he just felt like they would be glad to pawn him off on another caregiver.  

He just tried to turn his attention back to the holographic character in front of him. With two pistols in each hand, the blonde woman fired bright red lasers at the army of deadly zombies in front of her. With the heroine’s expert aim, each laser found its mark.

“Come on! Let’s go.” she shouted, looking down at the young man beside her.

Of course, the male character only existed so that the female character would have someone to rescue in the story. The timid looking actor with tears in his eyes couldn’t have been much older than Mike was. Maybe 20 or 22 years old? The shiny white waistband of his diaper was sticking up above his pants and his puffy rear end left nothing to the imagination.

“Grab my hand!” the woman shouted, pulling him off the ground.

Just then, Mike’s view of the holographic TV was obscured by his older sister’s lower body. She was wearing a t-shirt and a tight pair of jeans, her hands poised on her hips.

“Hey, move!” Mike groaned, twisting his neck in an attempt to see the three dimensional images behind her.

“You’ve been in here for over an hour and from the looks of the wetness indicator on your diaper, I’d say you need to be changed.” Brittany said.  

“Can you come back in 20 minutes? This is almost over.”

“Nope, you need a change now, Mikey. No more TV.”

In a split second, the hologram disappeared and Mike found himself staring at the wall. Groaning, he stood up with a huff and instantly felt his sister pulling back the waistband of his diaper to take a peek down the back.

“Good, you’re not poopy. I’m late to meet Jackie so hurry up. Lay down.” Brittany said.

Mike did as he was told, lying down on the living room floor. If his sister hadn’t turned off the TV, he would have at least had some entertainment while he lay there getting changed. Now he just had to stare at the ceiling as she untaped his diaper, running baby wipes over his crotch. In the beginning of the summer, he had been embarrassed about the prospect of his mother and sister seeing his chastity device… a symbol of his minor indiscretion last semester. Yet they didn’t seem at all surprised and hardly even commented on it. Apparently, Emily had told Brittany that she was keeping him in chastity and Brittany, in turn, told their mother long ago.

Emily. Mike had to admit that just thinking about Emily made his heart swell with joy. He’d never felt so strongly about a girl before. Did he have mixed feelings about the engagement? Of course! He still yearned for independence and adulthood, or at least something that vaguely resembled adulthood. His reservations about marriage had more to do with the institution of marriage though than with Emily herself. He was thrilled with the idea of spending his life with her and he knew if he just talked to her about having a little more freedom once they were married, he knew she would understand. Living with her would certainly be better than living at the dorms with that bitch Alyssa!

Just as Brittany was sprinkling powder all over him and sliding a diaper under his bare butt, their mother walked in.

“Hey guys, I just got off the phone with Horseshoe Park and it looks like the venue will be ready in time for the wedding. I’m so excited for you Mikey! I know it’s a cliché to say this but I just can’t believe my baby boy is growing up so fast. It seems like just yesterday that I was that foolish single mom trying to potty train you.” his mom said.

Brittany snickered and rolled her eyes as she taped up Mike’s diaper.

“I can’t believe you actually thought thatwould work.” Brittany said, standing up and dropping the wet diaper into a metal trashcan in the corner before cleaning her hands with a baby wipe. 

“Well Britt, it was just such a breeze training you. I think you honestly took a few days before you stopped having accidents. I guess I just got overconfident. It was a different time back then. You know Mikey, when you were born, Dr. Lauren Halie’s book hadn’t even come out yet. We knew boys were having trouble back in those days but… well, we didn’t know how much extra care you little guys needed.” his mom said, playfully pinching his cheek.

“Ugh, yeah. I know all about that book, mom. I took a class on it last semester.” Mike said, rolling his eyes.

“Oh sweetie, what are you so grumpy about? Aren’t you excited to see Emily tomorrow?” his mom said.

Mike smiled and nodded.

“That’s a good boy. Now I’ve packed your clothes and everything. Your bags are by the door to your room. Remember, we’re leaving at 11:00 sharp tomorrow.”

Emily. Just the mention of her name was enough to lift his spirits. Most of his disgruntled mood just stemmed from the fact that it was the last day of summer and he had to go back to school andback to living in the dorms. Thanks to the new rules that the administration had passed, unlike previous graduating classes, he and his fellow male students wouldn’t have any new freedoms as sophomores. So he was essentially going back to a minimum-security prison for the next few months. Then again, hopefully he’d be able to move in with Emily after the wedding. 

Lying in bed that night, Mike tossed and turned, unable to get to sleep. He was excited to see Emily without a doubt but he felt like he had to temper his expectations. It had been a good summer overall and Mike had even gotten a chance to see some of his old guy friends from high school. Those boys were all still living at home and getting their diapers changed by their mothers. Mike’s own mother had even been called to babysit them a few times! In contrast to them, Mike felt like he was actually advancing towards adulthood pretty quickly.

Emily had come to visit him for two weeks in July. She was on an accelerated schedule doing summer classes and two weeks was all she could spare. Her visit had gone great… except for one thing. Mike had expected to get unlocked, to be allowed out of chastity and for them to have amazing sex for the entire time she was there. While she had unlocked and pegged him the first night, he had been promptly locked up afterwards. The quick orgasm she had given him made him hope there were more to come. Towards the end of the first week, she unlocked him for a quick hand job, which he heartily enjoyed. That was it though. Yet he had given her oral a whopping 10 times while she was there!

It was all hardly fair but she made it clear that he wasn’t allowed to askto be unlocked or to ask for sex… and anyway, the sex that he really wanted, he figured she wouldn’t give him. Mike desperately wanted to enjoy putting his dick inside herfor once! “Misogynistic intercourse” was what one of his textbooks called it. In high school, Mike and a few of his friends found some old dusty magazines in a library during their field trip to the local university. In one of them, there was a photo of some gorgeous woman with big boobs was getting fucked by this tall, muscular guy with a huge dick. She looked like she was really enjoying it too! It was the ultimate symbol of adulthood and power in Mike’s eyes. Of course, Mike didn’t look like that though and his penis wasn’t anywhere near as large as the man in the old magazine. Yet he couldn’t help wonder if this was the reason most pornography had been banned in North America. Politicians said it was demeaning to women but Mike figured that the Matriarchal Feminists just didn’t want any symbols of male dominance or male power allowed in society. Unable to really have sex with his fiancé, all Mike could hope for was a hand job when they finally met up again. 

In truth, no males looked like the ones in old movies or pictures. Even in adulthood, boys were slender and short with only thin wisps of fuzzy, patchy facial hair. Mike hoped that someday soon, he might grow some visible facial hair or at least a few hairs on his bare chest.

Eventually, Mike must have fallen asleep because the next thing he knew, his mother was waking him up and sun was shining in through his bedroom window. Their trip to the university was uneventful. Mike stared down at the rooftops of houses as their car’s jet engine grumbled away. Brittany talked practically nonstop about the classes she was going to be taking and how difficult to professors were. Suddenly, Mike’s watch vibrated for a moment and he looked down at its screen.

EMILY: Want to do dinner tonight? I can pick you up at 5:00.

He quickly sent an enthusiastic ‘yes’. When the car landed on campus, his mother gave the two siblings a warm hug before yanking her son’s pants down to check his diaper. Mike frowned. It wasn’t as though his mother had ever been shy about public diaper checks but with so many attractive girls walking around the campus parking lot, Mike had hoped she would have made an exception. He was found dry or at least mostly dry. While Brittany was left to walk to her dorm on her own time, Mike’s mother insisted on walking him over to his.

“Be a good boy this semester. Remember, I’ll be in town a couple days before the wedding to help get everything set up, okay?”

Mike nodded, slinging his bag around his shoulder.

“Do you want me to walk you up to your room? It might be nice for me to have a chat with Alyssa.”

“No, mom. I’m good, seriously, I’ll be fine. I’m a sophomore. I can handle this.” Mike said.

“Well… okay. I guess I know you’re in capable hands. I love you so much.” she said.

Mike couldn’t help but wince as she gave him a big kiss on the cheek and two firm pats on his padded rear end.

“Love you too.” he mumbled.

Taking an elevator up to the dorms, Mike walked in to see a number of young freshmen boys there with their mothers talking to each R.A. assigned to their rooms. Still, it seemed odd that there were only about half as many freshmen boys this year as there had been the previous year. Were there fewer boys applying to go to school or was the university just acceptingfewer boys? He was, after all, at one of the few universities in the country that allowed boys as students. Brushing past them, Mike walked to his room. He smiled upon seeing Drew lying on the bed across from his in a baggy t-shirt and sweatpants. The skinny kid had the same messy, wavy hair that he always did… wild and untamed, just like Drew himself.

“Wow, I didn’t expect to see you back this semester!” Mike said.

“Shut up, you dork.” he said, getting off the bed and giving Mike a quick hug.

“No, I just meant… weren’t you like failing multiple classes last semester?” Mike asked.

“Yeah, technically but my mom wrote a letter to the university’s president. The woman’s got friends in high places. So I guess I’m back for at least another year or until I get kicked out.” Drew said.

“Its great to see you, man. I thought I’d have some random freshmen as my roommate. I want to at least try to have a little fun this semester.”

“Yeah, well, speaking of having fun or… nothaving fun, I heard you turned to the dark side.”

“Huh?”

“Oh, don’t even pretend you don’t know what I’m talking about. You went to that male students’ rights march with me last semester. Now I hear you’re engaged?”

Mike sighed, staring at the floor for a moment before dropping his bag beside his bed. A dribble of warm pee escaped into his diaper causing him to let out an audible whimper.

 

“Well? Is it true?” Drew pressed.

“Yeah, I guess it is true.”

“So you’re actually going to go through with it?”

“I don’t know.” Mike shrugged.

“Really? You thinking of calling it off?”

“Huh? No, no, no. You can’t tell anyone I said that. Look dude, I love Emily more than anything. She’s the love of my life and I’m really excited to be her husband.”

“Gross. You’re gonna make me barf, dude.” Drew groaned.

“I’m just going to sit down with her before the wedding and… uh, have a talk with her. I’m going to tell her that uh, as her husband, she needs to respect me because I’m, you know, an adult.”

Drew burst out giggling at Mike’s mention of the word ‘adult’.

“Shut up!” Mike groaned.

“Hey, don’t get me wrong. Its great to hear that you aren’t completely pussy whipped but do you really think a girl like Emily will go for something like that? She’ll probably laugh harder than I did!” Drew said.

“I guess I still need to think about how I’m going to phrase it… I just need to use the right words. Emily wasn’t like all the other R.A.s. She is a kind, loving, and logical person.”

“Look, she’s not a bitch like Alyssa. I’ll give you that. But Emily is a Matriarchal Feminist right down to her bones. Sure, she’s not as radical as some of them but she believes in everything in that stupid book by doctor whats-her-name.”

“You haven’t even read that book.”

“Yeah well, I’m not getting married either!” Mike shouted.

“Hey!” a stern female voice said.

Mike turned to see Alyssa in the doorway of their rooms.

“Boys, we’re in the dorms now so its time to use your indoor voices. I excepted everyone to be a little rowdy considering you guys just got off summer break so I’ll let you two off with a warning. Tonight though, I expect you both to settle down and go straight to sleep after you both get changed and ready for bed. Do you understand me?” Alyssa said.  

“Uh-huh.” Mike said, a little nervous to see her standing so close to him.

“Good. Orientation is in 5 minutes so I expect you both to be up front then.”

“We know the rules. We’re sophomores now, remember?” Drew said.

“Well Andrew, considering the way you boys behaved last semester, I think you could both use a little refresher. I’ll expect you both out there in 5 minutes.” 

Sitting in the main room under the bright florescent lights, Mike and Drew slouched in their two plastic chairs as Alyssa explained the rules to the wide eyed freshmen boys in her usual strict tone of voice. Sinks and high countertops with straps – the changing tables – adorned the walls. Even though it was always kept quite clean, the room had a naturally strong scent of baby wipes, powder, and just a hint of that smell of stale urine. Mike wasn’t sure whether the urine smell was always there, whether the freshmen boys’ moms had been changing their diapers today, or whether some of the boys in the room might be wet or messy at that moment. Feeling another dribble of pee in his own diaper, Mike realized he was hardly above it all. Yet soon it would be just a matter of time before he was living at Emily’s house. He loved the smell of her place and he’d likely be over there later tonight!

“Of course, from the hours of 8:30 a.m. and 4:30 p.m., you will be in class.” Alyssa said. “You may be signed out for an evening but only by someone properly authorized to do so. For most of you that means your mommies, a sister, or maybe an aunt. Or in Mikey’s case, you might see his fiancé here from time to time. Her name is Emily. She used to be an R.A. in the dorms here and she was one of our best. She doesn’t work here anymore though so I don’t want any of you bothering her. If you need something, come to me or one of the other R.A.s.”

Looking at each R.A., Mike noticed a few friendly faces from the previous semester; including an attractive looking blonde that he recalled seeing with Emily a few times. What was her name? Lucy? If only he and Drew could have gotten Lucy as their R.A. She seemed nice enough. She was a little heavier than she had been last semester and had clearly put on some weight but Mike wouldn’t dare mention it aloud. He could get disciplined by the school, not to mention punished by Emily for criticizing a girl’s weight out loud. Calling a girl “fat” could actually get him suspended!

Instead, they were stuck with Alyssa. Mike glared at her. Squirming in his seat, the chastity device under his diaper once again felt very tight around his penis. Alyssa’s black tank top showed off more skin than usual, though it had been a pretty hot summer so he couldn’t blame her. It was clear she wasn’t even wearing a bra. Her breasts weren’t huge by any means but Mike couldn’t help but wonder if she was just trying to tease him and the rest of the boys on that floor.

Mike had always been attracted to Alyssa and he hated her for it. Actually, he hated himselffor it. First, there was her awful buzzed, shaved head. Well, it wasn’t quite that short today, maybe an inch long? The masculine haircut should have been enough to turn him off. Though he had to admit her big, bright eyes were somewhat pretty. They were piercing, deadly serious, and intimidating. Whenever she gave him that look of hers, he knew she meant business. It made him scared and a little turned on at the same time. That silver nose ring of hers looked dumb enough but the biggest distraction that drew Mike’s gaze was the broad waistband of her underwear. Peeking up above her jeans was a hint of her red briefs along with their black waistband, and the brand name of her underwear in bold, capital letters proudly on display. Years ago, Mike had seen an old movie where one of the lead male actors had his underwear visible above his jeans like that. Emily never flaunted her underwear in public and hers were much sexier and more feminine than Alyssa’s were. Though he had to admit that there was some appeal to Alyssa’s tomboyish style overall. 

As Mike grabbed himself through the thick, wet padding of his diaper; he had a thought that made him frown. His attraction to Alyssa was based partially on her attractive body, partially on her gorgeous face, and also partially on something else. Alyssa was masculine in all the ways that Mike wished he could be. She was strong, independent, powerful, and most of all; she confidently wore underwear and could use the bathroom whenever she wanted! It was no wonder that she displayed her underwear with such pride. It wasn’t as though Mike would feel any more powerful if he walked around sagging his pants to show off his high rising diaper waistband! Quite the opposite actually. Diapers symbolized everything that made Mike feel incompetent and inadequate. Underwear symbolized the opposite not just for Alyssa but for all girls. Although, he knew Alyssa was probably flaunting it to reinforce her power over the boys in her charge. That had to be the reason she deliberately allowed her underwear to show. It wasn’t a sexual tease or flirtation. It was a show of dominance: a symbolic representation of the fact that she wore the pants in all of their interactions… and the underpants.  

Just a few hours later, Mike stood patiently in that same room waiting beside Alyssa for Emily to arrive and release him from his captivity. The second his beautiful fiancé stepped into the room, Mike sprinted over to her and gave her a huge hug.

“Whoa, take it easy there, champ.” Emily said, almost falling over.

She gave him a quick kiss on the lips. The dress she was wearing looked amazing.

“I missed you!” Mike said, his voice sounding a little higher in pitch than normal.

“I missed you too, kiddo.” Emily smiled. “Now just give me a minute and we’ll get you signed out.”

Alyssa handed her a tablet with a screen on it. Mike couldn’t believe all the paragraphs and fine print she had to go through but he figured she wasn’t reading every line. It was just some legal bullshit that tied into all the university’s crazy rules for boys.

“Nice bag.” Alyssa said, noticing the large purse with blue and white stripes that was slung around Emily’s shoulder.

It took a few seconds but Mike quickly realized it wasn’t a purse at all. It was a diaper bag.

“Thanks. I figured since Mike’s my fiancé now, I’m going to have to take a little more responsibility on nights when I have him.” Emily said, patting the bag on her hip.

“Good plan.”

“How was your summer?” Emily asked with a smile.

“Not bad. Did a little travelling. It’s nice not having a whole floor of boys to look after but I guess I can work here for another year before I graduate. The money’s good.”

“Are you and Amy still dating?”

“We broke up.”

“Oh Alyssa, I’m so sorry to hear that.” Emily said with a frown.

“Its totally fine. I broke up with her actually. We just wanted different things. Maybe we were too alike.”

Mike sighed heavily, hoping that Emily might take the hint about how impatient he was getting. They were wasting valuable time that they could be spending together. He hated when Emily or any woman talked about him like he wasn’t sitting right there in the room, like he was some helpless baby who didn’t understand what they were saying.

“Does he have a clean diaper on?” Emily asked.

“Of course, just changed him a half an hour ago. I checked him about a minute before you walked in and he was practically bone dry. I was kind of shocked quite frankly.” Alyssa said.

“Oh really?” Emily smiled. “Is my little boy happy in his clean diapee?”

Mike frowned at Emily’s tone of voice.

“Aw, come on, sweetie. I’m just joking around. Come on, you’ll feel better once we get you fed.” Emily said, tussling his hair.

“Have him back by 9:00.” Alyssa said.

“You got it.” Emily smiled.

As much as Mike hated to admit it, Emily was right. They ordered an appetizer of French fries when they arrived at the restaurant and he quickly perked up.

With her long brown hair down around her shoulders, Emily had a purple satin dress on that showed off a hint of cleavage. As she brushed her hair back behind her ear, Mike could see that her lacy pink bra strap was showing just a little bit. A stream of warm pee trickled over his balls before getting absorbed into his diaper. Squirming a in his seat, he crinkled a little. While his diaper wasn’t that wet, the tiny bit of warmth was enough to arose him and his penis was again demanding release from the plastic tube locked around it. He sucked some juice from the plastic sippy cup that that waitress had brought them while he listened to Emily talk about the numerous classes she was taking. Emily had always said one of the things she loved about him was what a good listener he was. He didn’t interrupt like other boys. Anyway, it wasn’t as though his summerhad been particularly eventful. The most fun he’d had since she left was the night that his friend Ethan from high school came over to play video games. 

“So anyway, I couldn’t believe it but they offered me an administrative position at the hospital. I would have two people working underneath me. Isn’t that great?” Emily said.

“Um, yeah but… I thought you said you were planning on going to medical school to become a doctor?” Mike said.

“Well, I thought about that. I might still go to medical school but this job pays really well. Besides, we’re getting married soon and it’s going to be a lot harder for me to support us if I’m a full time student. Trust me. This is for the best, baby.”

Mike smiled as she placed her hand on his.

“Can we go back to your place after this?”

“How about now? We can put our food in to-go boxes and grab the check real quick. I’m hungry for something other than food and um, I don’t want your mouth to get tired out here.” Emily said with a giggle.

“Let’s go.” Mike smiled.

The second they opened the front door to Emily’s apartment, the two lovers began passionately kissing. While Mike’s chastity device was getting really uncomfortable, he was as enthusiastic as ever as she yanked his pants down to reveal his diaper. By this point, he wasn’t even embarrassed to have it showing. It would just make it that much easier for her to take it off and unlock him. The lighting in her apartment wasn’t all that bright anyway. He grabbed Emily’s breasts through the taught panels of her pink bra before sliding his hands up underneath the soft fabric of her dress to fondle her toned body. Her legs were toned and smooth. Brushing his hands away, she grabbed him by the wrist and led him towards the bedroom. To top it all off, there was an aroma of lavender and scented candles in the room; a welcome respite from the less pleasant smells of the boys’ dorm rooms. He could believe that he would soon have this gorgeous woman and her immaculate, lavish apartment all to himself.

As Emily dropped the diaper bag in the living room, she practically pushed Mike into the bedroom. She pulled the dress off over her head and just as quickly, she unclasped her pink bra. Now Emily stood in front of him in only a pair of lacy blue panties. 

“See anything you like?” Emily asked, squeezing her bare breasts together. 

Mike licked his lips. The sight of her statuesque nude body never failed to leave him transfixed. Emily snapped her fingers and pointed to the floor beside her bed.

“On your knees. You know the drill.” she said, raising her eyebrows.

“Um… uh, Emily?”

“Yeah?”

“Could you uh… ch-change me first?” Mike asked.

He was embarrassed to ask but he figured he might as well get comfortable if he was going to go down on her. Emily slowly took a step towards him. Looking at him seductively, she slipped two fingers into the leg band following it to the middle of the diaper. The thought that her fingers so close to grazing his genitals made him even more aroused.

“You’re just a little damp. I’ll change you later. Now quit stalling.” Emily said, sliding down her lacy panties and taking a seat on the bed.

Grabbing a handful of Mike’s shaggy brown hair, she guided his mouth down onto her womanhood. It was a familiar enough sight. The glistening wet lips of her clit were framed nicely by a landing strip of short pubic hair. Mike dutifully moved his firm tongue around and around in concentric circles as she moaned.

Well, he wasn’t going to get a diaper change now until he was done. What else was new? Whether it was Emily, his mom, or his sister; he got a diaper change whenever it was convenient for them not him. His opinion mattered very little. While mildly annoyed that he hadn’t gotten changed into a clean diaper, he was still determined to show her that his oral skills hadn’t suffered over the summer. He was going to ‘pay it forward’ and ensure that he earned an orgasm no matter what. As her breathing began to quicken, Mike had a firm grasp on her bare thighs, still working wonders with his tongue. Finally, he felt her legs squeeze around his head as she came so loudly and vociferously; he had to wonder if the neighbors had heard. Mike figured it had been a while since she too had experienced an orgasm.

“I love you.” she said, still panting.

“I love you too.”

She stoked his hair for a moment before standing up. Mike could only admire the gorgeous curves of her nude body in the dim bedroom light as she slipped on a pair of red, bikini style panties followed by a white tank top. Her hard nipples were clearly visible through the fabric.

“Why don’t you get up? Have a seat on the bed.” Emily said.

“What about my uh…” Mike pointed to his diaper.

“Mikey, those things are state of the art. With that absorbent leak core, you could pee in that thing 10 more times before it came anywhere close to leaking. Besides, we’re going to be living together soon. I don’t mind if you sit down in my apartment while wearing a wet diaper. Really, don’t worry about, okay?”

“Um, okay?”

Taking a seat on the bed, Mike was unsure of how to feel. It appeared as though Emily wanted to talk to him about something but he was still holding out hope for at least a hand job and a diaper change. Taking a seat beside him on the bed, Emily put her arm around him, gently stroking his back. Mike’s posture relaxed, clearly feeling comforted by her touch, though still more than a little horny.

“I’m guessing after being in chastity for the last few weeks, you’re pretty anxious for me to unlock you and let you cum, right?” Emily said.

“Well um, y-yeah?”

“I’ve given your chastity a lot of thought since my little visit over the summer. I even got a chance to talk to your sister about it. Well, she agreed with me that our special day would be that much more special if you didn’t have an orgasm until our wedding night.”

“What?!”

“Mikey, calm down.”

“But… but that’s forever! You can’t be serious.”

“Mikey, I already told you once to calm down. Don’t raise your voice to me.” she said sternly.

“S-s-sorry.” Mike said.

“As I was saying, I’ve given a lot of thought to this and I think it might reinforce just what an important commitment this is. You’re going to need to be able to love and obey me during the times when I’m allowing you to have orgasms as well as the times when I’m notallowing you to have orgasms. I think this is just one more reminder that for the rest of our lives, I’m going to be the one making that decision… not you. Do you understand me?”

“Yeah… I guess.”

“You still want to love me, obey me, and be my husband. Right?”

“Yeah, of course!”

“You need to remember that it wasn’t even my decision to put you in chastity in the first place.”

“I remember. It was Alyssa. Ugh, I hate her.”

“Mikey, it wasn’t Alyssa’s fault. Do you remember what happened last semester that caused Alyssa to put you in enforced chastity as a punishment?”

“Yeah, I remember.”

“Alyssa caught you tugging and rubbing the front of your diaper like a naughty little boy after lights out. You knew the rules for freshmen boys and you broke them. You are wearing that device because of your actions… not mine.”

Mike frowned but he said nothing. He felt a deep sense of sexual frustration, as if he had been tricked. Even so, he knew that throwing a tantrum wasn’t going to do him any favors. It would just get him into trouble. Even though Emily had her arm around him and was gently stroking his back, he resented her in that moment as he felt another trickle of pee in his wet diaper.

“Now all of that being said, the boys in the dorms aren’t due for a prostate milking until a month from now. Like you’ve been told before, it’ll get out some seminal fluids and keep your prostates and your other boy parts healthy. I’ve already told Alyssa that I’ll be taking care of you that night. But since I know you’ve had a long summer, I’ve decided you could benefit from me milking you tonight. You won’t have an orgasm but I think you’ll feel a lot better when we get you taken care of… and you’ll be a lot healthier. Now doesn’t that sound nice?” Emily said.

“I guess so.” Mike said, unable to hide his disappointment.

“Great. Well, I’ll get everything ready on the bed and then we’ll have you lay down on your tummy, okay?”

Mike watched as Emily turned to leave the room, staring at her toned butt in the skimpy red panties she was wearing as she pulled her brown hair into a ponytail. When she returned a moment later; she had a box of medical gloves, a bottle of lube, and some baby wipes.

“We’ll get you in a clean diaper after this but right now I think it would be a good idea to keep that same diaper under you to catch everything. Come on, flip over.” Emily said.

Grabbing a towel from her closet, Emily laid it on the edge of the bed. Standing up, Mike repositioned himself so that he was laying on the bed, face down with his legs dangling over the side.

“Do you want a pillow? It’ll probably be comfier.” Emily said, sliding a pillow over.

She was right. It did feel better lying with his face and chest on the pillow. Emily carefully ripped back the tapes on his diaper and adjusted the garment until he could feel cool air on his naked, damp butt. The warm, sodden padding of his wet diaper was still pressed up against his crotch. He listened as Emily opened up the bottle of lube and squirted some onto her gloved fingers.

Whimpering to himself, he could feel one slimy finger pushing firmly up against his puckered sphincter. Then he felt Emily’s warm breath on the back of his neck as she began to whisper to him.

“Sweetie… you’re going to have to try and relax. Take a deep breath for me.”

Mike inhaled, then exhaled.

“Good boy. One more time. Breathe in for me? Now breathe out.”  

Mike did as he was told and felt Emily stroking his back with her one free hand. Then before he knew it, she had slipped a finger into his butt hole. It slid in… then out. Next she slid two fingers in and this time, he closed his eyes tightly and tried to remain focused on relaxing. Somewhere inside of him, her two firm fingers found their mark and almost imperceptibly began to message his prostate.

The sensation wasn’t as enjoyable as pooping and it wasn’t as erotic or intimate as her pegging him in the missionary position. While there were some aspects of it that felt good, frankly, Mike would have rather been messing his diaper than dealing with Emily slowly milking his prostate. Neither one would result in an orgasm but he at least had more control over pooping in his diaper. He often got to decide where and when he messed himself, at least most of the time. Mike sighed at the thought that pooping in his diaper alone could be more enjoyable than any act Emily performed on him in their bedroom but he supposed this was a special case. During his freshmen year in college, Mike had read in a textbook about ‘dirty boys’. Apparently, the term once applied to boys who enjoyed pooping in their diapers. In was rarely used now because it was assumed that all boys enjoyed pooping in their diapers. Mike had always resented that ridiculous conclusion. After all, if he had just been allowed to poop in the toilet, he gladly would have done so! Maybe Drew took some infantile pleasure in messing his diapers but Mike was different!

Now, he was rethinking all of it though. In chastity permanently, messing his diaper was a choice he could make almost daily to offer himself some pleasurable relief. It was cathartic. While Mike might have denied it for a long time, now he was beginning to think that he really was a ‘dirty boy’ after all. The guilty thought gave him no comfort as Emily’s two, lubed up fingers persisted in penetrating him, massaging his prostate in gentle circles.

“That’s it. Good boy. Just relax… you’re doing great.” she said, stroking his back.

Emily’s soft voice offered little reassurance. He wished that he could at least have watched TV while she penetrated him. Mike yearned for a distraction but instead, he was trapped in the present experience, sensing every little detail of the prostate milking process. The wet diaper against his crotch no longer felt warm. It was now cool, clammy, and hardly comfortable.

Just then, his eyes popped back open. He felt like he was peeing in his diaper again. For a moment, he feared his diaper might flood or that he might pee on Emily’s bed but it was only a small trickle. In that moment, he realized what was happening. He hadn’t actually just peed. His body had purged itself of that tiny bit of seminal fluid Emily had been talking about. For some reason, rather than alert her to this fact, he just laid there silently while she continued massaging his prostate. In his current position, he didn’t real feel empowered to say much of anything to her. He was totally exposed and under her control. The process would end when she made the decision to stop.

About two minutes later, she withdrew, gently putting her arm on his shoulder to roll him over onto his side. Tiny drops of cum dripped from the clear plastic tube around his now limp penis. A rubbery sound confirmed she had removed her medical glove as she rolled him onto his back, his sore rear end resting on the towel. Folding up the damp used diaper, she carried it out of the room, still dressed in only her panties and a tank top. Strangely, Mike barely even looked at her as she exited the room. He was suddenly feeling more subdued, tired, and even relaxed.

She returned promptly with a clean diaper in one hand and a tiny bottle of power along with a pack of wipes in the other. Pressing the screen on her watch, the tiny lock on Mike’s chastity device popped open. She slid off the lock along with the two-inch, hard plastic tube that had covered his penis. Despite having thought about this moment for so long, Mike felt largely numb to it all as his fiancé cleaned the tube with a baby wipe before wiping off his balls and penis. A few seconds later, the tube was back on and the lock snapped shut, affixing the tube to the ring around his balls. Once again, he was locked in. His fate was sealed and while he might technically get unlocked once or twice in the future, it would be two months before he would have the chance to have an orgasm. With a sprinkling of powder, Mike’s butt came to rest on a clean diaper and Emily swiftly pulled it up and taped him in place. Finally, he was clean and dry once again.

Sleepy and starting to zone out, Mike said nothing on the car trip home.

“Mikey?” Emily said, breaking the silence.

“Huh?” Mike said, in a daze.

“Have you given any thought to who you want to be your Best Boy at the wedding?”

“Huh?”

“Your Best Boy. You know, the boy who is going to stand next to you at the wedding ceremony.”

“Well, Drew I guess.”

“Are you sure?” Emily asked, raising an eyebrow.

“Yeah, why not?”

“Sometimes I think he’s a bad influence on you. Maybe he’s turned over a new leaf this semester but he got in a lot of trouble last year. He doesn’t always know how to behave and he gets really rowdy, even more so than a normal boy. His well connected mother was the only reason he was allowed to come back this semester.”

“So… I can’t pick Drew then?”

“No, I didn’t say that. This is your choice to make. But if he steps out of line or misbehaves at the wedding, my mom will give him the worst spanking of his life. Make sure he understands that.”

“Okay, y-y-yeah.”

With that, Emily walked Mike up to the dorms, signed him in, and shortly thereafter it was lights out.

 

Check out the link to read Chapter II:

https://www.amazon.com/dp/B07SQLQB6P 

[Menaiya]

Glad you're writing again. I haven't seen any other books out of you lately. Any more anthology books coming too? (glad this one is out!)

[MagicGuy1971]

You should do one with women. You could even set it in an alternate present day, the point of divergence could be the failure of the 19th Amendment.

[Eagle0769]

In order to see the next chapter we have to buy your book?

[Diaperingdaddy]

a nice read. i look forward to the next book!

[CDfm]

That would be horrible. Servicing your wife is one thing but to have to preform regularly and then to only be milked would really suck. I would rather go without any if I were in Mikes shoes. 

[Diaperingdaddy]

On 6/14/2019 at 5:22 AM, CDfm said:

That would be horrible. Servicing your wife is one thing but to have to preform regularly and then to only be milked would really suck. I would rather go without any if I were in Mikes shoes. 

Did you read the whole book? It gets better.

[CDfm]

No I am almost embarrassed to say but I don’t have a kindle so I didn’t get the rest.

[Sarah Penguin]

On 6/15/2019 at 9:01 AM, CDfm said:

No I am almost embarrassed to say but I don’t have a kindle so I didn’t get the rest.

You can read kindle stuff without an actual kindle ereader.  There are free apps for phones, a windows app, as well as a thing where you can read anything you have online in a web browser tab. 

[halfdeadcorpse]

1 hour ago, Sarah Penguin said:

You can read kindle stuff without an actual kindle ereader.  There are free apps for phones, a windows app, as well as a thing where you can read anything you have online in a web browser tab. 

Yup, I've never had an e-reader and have gotten by fine with the app on my phone, and later my tablet.

I believe NewGuy20 has recently released another eBook that's a compilation of elements from his prior books, but since I have all the prior ones I've decided to skip this one. I would recommend their books, they are reasonably priced and well written in my opinion.