XXX Ms. Easterfield's Baby (Chapter 31 added, no really!)
A young man knows something missing in his life and finds it in the most unexpected place
Posted on
Add A New Story
The page list
The Next Page
Chapter 1

********Sam sat patiently in his car listing to a morning talk show, waiting for school to start. *This was it, his senior year of high school. *The first day leading to his last day of school and he couldn’t wait. *It’s not that he hated school or anything, he just wanted the freedom that college was sure to bring. *So here he sat absent mindedly waiting to hear the bell. *He knew this would be his best year yet, how couldn’t it? He had saved all his electives and passing periods in order to create the best senior year in the history of public school. *He looked down at his schedule and smiled to himself. *All TA (teacher’s assistant) classes and all with the same smokin hot teacher. *




********The bell sounded, as Sam watched his class mates poor out of various buildings and cross the quad to their next class. *It would be their second period of the day and the first for him. *Man being a senior was good. *He had turned 18 the week before school started and while nothing had really changed he liked knowing he was now an adult. *




********Sam listened as the shorter five minute bell sounded. *Thinking he didn’t want to upset his teacher day one, he got out and headed to class. *He quickly left the teacher’s parking lot, where he had managed to slip his car into since campus safety doesn’t check it once class has started, and joined the throngs of students, making their way to class.

“Good morning Sam, nice to have you back this year.” *Ms. Easterfield greeted him as he pushed open the door to the classroom. *Sam smiled and nodded in way of response, he was trying not to stare at the amazonian goddess before him. *He had the biggest crush on her ever since freshman year when he had taken intro psych with her. *Three years of schooling later and he was still just as enamored with her powerful 6’5” frame. *

She had been a new teacher his freshman year and had immediately became his favorite. *She was fresh out of college and eager to be the perfect teacher. *She often shared stories with her classes of her time in college and the many collegiate teams she had played on. *With her height and natural athleticism she had managed to letter in softball, basketball and volleyball, the latter two she was even team captain. *She had graduated with a degree in psychology, and teaching. *This fact alone would probably would have been enough to become Sam’s favorite teacher, but add on to it her great body and looks and it was all Sam could do not to stare.

“Why don’t you have a seat at my desk. *Today I’ll just be going over syllabi so I won’t have anything for you to do really. *I would let you just skip today but I may need you to run and make copies if I should run out, plus I want to show you how the grade book software works in between classes.” Ms. Easterfield got up from her desk in order that Sam could take her seat. *As she stood Sam was taken back my her outfit. She was wearing a low cut V shirt, showing off her great cleavage, and a tight black skirt with a high slit. *Sam was sure that if the principal had not been a male, Ms. Easterfield would get in trouble for her revealing outfits. *

Sam quickly took a seat behind the computer, hoping to hide his growing excitement. *“What’s the matter Sam, did you forget how to talk over the summer?” Ms. Easterfield smiled down at him from where she was standing.

“Oh, Um sorry... I’m not trying to be rude. I’m just not a morning person.” *Sam said blushing a deep crimson.

“Well wake up sleepy head it’s already the second period.” *She reached down and tousled his hair making him blush even harder. *

“Actually it’s my first.” He replied trying to will the blood out of his cheeks.

:”That’s right, I looked at your schedule, my it is an easy one isn’t it, and only having to have me all day.” *By this point other students were starting to fill in the desks. “Go ahead and feel free to use the computer to surf the web.” She said as she headed towards the front of the class. “Just stay off sites that will get me in trouble.” She added as she got to the front. Causing a fresh wave of blood to course through the skin on his cheeks.

Now Sam sat alone at the back of the class behind the teacher’s desk watching as she got things started. *He could tell a lot of the other guys in the class were just as taken with her as he had been, when he first had her. *Now with her attention elsewhere he felt safe to stare. *Her dark skin always looked a healthy tan, thanks to her mother’s Brazilian ancestry. Sam noticed for the first time she was wearing a jade necklace and earrings that stood out on her skin and highlighted her wonderfully dark eyes and hair. *She had on black heels that added another two inches to her all ready tall frame. *Sam’s gaze moved up her immaculately sculpted legs to her thin waist and on up to two of her most stunning assets. *Sam’s eyes lingered on her breasts. *On a smaller frame the double DD’s would have looked ridiculous, but on her tall frame they looked perfect. Finally his eyes moved on and continued their upwards climb. As Sam’s eyes moved up they caught Ms. Easterfield’s. *Sam blushed a deep crimson when he realized that he had been caught leering. *Best to entertain himself with other eye candy, he thought to himself.

He reached into his backpack to remove his iphone. *He switched on its bluetooth and tethering, before disconnecting the Ethernet cord from the back of the school’s desktop. Now time for a little big brother free net surfing. *Sam wasted no time in pulling up some of his favorite abdl sites. Unbeknown to Sam, Ms. Easterfield had a key logger program, so even though he was using his phone’s internet she was still tracking his activities online.


Chapter 2


********It didn’t take long for Sam to settle into a routine at school. *He would sneak his car into the teacher’s parking lot just before second hour, then head to Easterfield’s class. *He had two of her classes back to back before lunch. *Sam’s lunch was extra long because he had an open period immediately following the lunch hour. *Then he would report back to Easterfield’s class for another two periods before the day ended. *His TA schedule was sociology first thing, then abnormal psychology, followed by intro to psychology, and finally her advanced placement psych course. The fact that Easterfield taught only psych related courses gave him the perfect excuse for TA-ing only for her, as he was planning on majoring in psychology when he graduated. *In reality he wanted to spend as much time with his dream angel as he could. The first week had been super easy as it was laid back while everyone eased back into the school year. *He had ample time and privacy to play on the web as the back row was entirely empty, with the exception of abnormal psych, which had one student in the back row.

********Sam spent most of that first week surfing abdl sites. *He had never worked up the nerve to actually buy himself diapers, but he knew the second he escaped his crappy home life he wanted to be diapered 24/7. *The fact that he hadn’t yet experienced wearing diapers only made him more anxious to live vicariously through the characters he read about online. *The only class he wasn’t constantly surfing the net in was his abnormal psych class. This was do in large part to the girl sitting in the back row, and because he found this class the most interesting. *

********At first he had been annoyed that someone was in the back row. *Easterfield’s policy in general was the back row was to remain empty, but due to the popularity of abnormal psych there just wasn’t enough seats. *An exception had to be made, and this girl had been the last to arrive so she got the seat. *After Sam got over his initial annoyance he realized how strikingly beautiful she was. *He had never seen her before in his years at the school so he wasted no time in looking her up on Easterfield’s attendance program. Turns out she was a senior transfer student named Kayla. *She had moved to the area from mid west. *

********Sam hadn’t ever had a girlfriend, he told himself they just were not worth the hassle. In reality he never thought he could get one. *However this Kayla was exactly the kind of girl he would want. *She had a strong athletic body, short blond hair pulled back into a ponytail, and an angelic face. *She looked like the kind of girl who wasn’t willing to take crap from anybody. *Sam was desperate to find some reason to talk to her. *However his lack of skills with the girls left him tongue tied. *He caught a break when Kayla leaned back to ask him a question.

********“It’s Sam right?” She asked in a low whisper.

********Even her voice sounds heavenly, Sam thought. *“Uh, yeah that’s right.”

********Kayla smiled at his shy awkwardness. *“Well, I’m Kayla. *I wasn’t here the first day, is there anyway that I could get a copy of the syllabus.”

********“Yeah sure, I’ll print one for you.” *Sam immediately turned to the computer to print one off for her. *“Here you go.” He said as he handed her the freshly printed copy.

********“Thank you.” *Kayla flashed her brilliant smile again, melting Sam’s heart instantly. *She began to turn back around in her seat and Sam realized that his window was quickly closing.

********“So, your a transfer right?” *Sam asked keeping his voice down, so that Ms. Easterfield wouldn’t hear them.

********“Yeah, we just moved here from Lincoln, Nebraska. *Which kind of sucks because I would have been captain of my softball team this year.”

********“Oh, why the move then?” *Sam was so thrilled to be having a conversation with an attractive girl that he stopped thinking about being quiet and the volume of his voice started creeping up. *Ms. Easterfield heard Sam and Kayla in the back of the class. *She smiled to herself. *She had always thought Sam to be painfully shy and was happy to see him talking to girl. *

********Kayla got kind of quiet before answering. “Well my folks actually just split and my mom wanted to put as much distance between them as possible.”

********“Oh, I am so sorry to hear that. I wish my parents would separate.” Sam realized the mistake of what he said the moment he said it. He started blushing as he tried to back track. “Umm, that’s not what I meant to say, I’m sure it sucks, its just all my parents do is fight, argue and scream.”

********Kayla reached out and placed a hand on top of Sam’s arm to stop his rambling which was mostly to himself at this point. “It’s okay Sam. I understand mine were the same way.” *Her hand felt warm on his skin. Sam wished the moment would never end. But as if on cue the bell sounded ruining it. *Kayla quickly scrambled to put her books away, as all her classmates had been packed up and waiting for the bell for the last several minutes. Kayla stood and lifted her backpack up. *At that moment Sam realized two things, she was much taller than he thought, she stood right around 6 feet. Second as she lifted the bag he could see the sinewy muscles move in her arm, she was much larger and stronger than him, that was for sure. Sam is what you would have called a late bloomer. *Even now in his senior year he stood at just 5’3” and was constantly being mistaken for a freshman.

********“Have a good rest of the day and if anyone gives you any problems just let me know and I’ll give them some.” Sam had a sheepish grin on his face. The thought of him giving anyone trouble was absurd. He was hoping that Kayla would find the humor in it as well. *

********The comment had the desired effect as Kayla immediately began to smile. Sam felt like he was basking in warm sun light every time he saw that smile. “Thanks Sam, but how about if anyone gives you trouble, I’ll have your back.”

********Sam shrugged, “Yea that’s probably more likely.”

********“Ah don’t worry little one, I’ll protect you.” *Kayla smiled again before heading out the door to her next class. *Sam wasn’t sure how to take the comment, but his mind was already thinking about various daydreams involving him and Kayla. Sam didn’t even notice Ms. Easterfield walking back towards the desk until she was just about next to him. Sam’s mind immediately shifted into panic mode as he realized what was up on the computer monitor. *He had pulled up his abdl sites at the beginning of class today but got distracted by Kayla. *Now sissykiss was still pulled up and Ms. Easterfield was almost within a view angle of the screen. Sam rushed to close the the tab, only to be greeted with a INTERNET EXPLORER NOT RESPONDING! Sam was out of time, all Ms. Easterfield would need to do is turn her head to see the bright pink background of sissykiss. Sam quickly slid his foot over the power bus-bar and stepped on the on off switch. *He let out a huge sigh as the screen went black.

********“Sam, you okay? You looked flush.”

********Sam nearly jumped out the chair when he heard Ms. Easterfield’s voice. *He spun on the axis of the swivel to look at her and assess whether or not she had seen anything. Ms. Easterfield was standing in the corner she had one hand in a storage cabinet grabbing paper but her body was turned facing Sam. *“Uh, no, actually I’m feeling a little feverish.”

********“Why don’t you go ahead and go home then.” *Ms. Easterfield’s voice took on a sympathetic motherly tone.

********“I think I’ll do that, I’m just going to restart your computer first, I think I accidentally shut it off with my foot.”

********“Don’t worry about it sweetey, I can handle that.”

********Sam started to get nervous again, he needed to plug back in the ethernet and clear the browsing history. “No, really its not a problem. *TAs are supposed to lessen the work, not create more, right. Besides I promise not to throw up on your desk.” *Sam smiled weakly, trying to play up the sick card.

********“Ok, then if you are sure. *I am going to go get my lunch out of the teacher’s lounge. Go ahead and take off for the day when you are done. Just be sure to check out with the office.”

********“Thanks I will.”

********With that Ms. Easterfield headed for the door. “Feel better Sam.” She said before disappearing into the hall. Sam wasted no time removing the evidence from the computer and checking out of school. *It was the first time that Sam wanted to get out of school with out seeing Ms. Easterfield.

********As Ms. Easterfield walked down the hall she couldn’t help but think that Sam had been acting weird. *It’s possible that he was feeling sick, but he seemed fine moments before when he was talking to Kayla. *Her woman’s intuition told her something else was at play here. *It was almost as if he was acting like a small child who just got busted eating cookies before dinner. *Then she remembered that she had a key logger on her computer. She had installed it her first year at the school, because she had suspected that her now ex-husband had been using her laptop to web-chat with other girls.

********Sam sat in his car and wondered what to do with the rest of his day. *He had been planing to finally make his first purchase of diapers this weekend as it was labor day weekend and he would have all day Monday to enjoy them. Today almost seemed like the perfect opportunity to do it. The fact that he was getting out early meant he could drive to a neighboring town to make his embarrassing purchase and then he wouldn’t have to worry about seeing anyone he knew.

********Ms. Easterfield got back to her classroom to find it empty. *She logged onto her computer and started with the web history. *It was empty, confirming her suspicion that Sam was hiding something. Next she checked her key logger, It was an advanced one that had code in it that sought out web addresses, user names and passwords. *It seems Sam has been busy on my computer this past week she thought to herself. She made note of the sites most frequented and the corresponding log in information. *She decided to look into it further when she got home and didn’t have to worry about the schools spy software. Then she would decide what to do about it.. She wasn’t planning on turning him into the school but her mind was already crafting more interesting ways of using this information. *It seems she too will have a busy shopping weekend with interesting purchases.

Chapter 3

********Sam started his car and headed towards the nearest neighboring city. The radio was on but he wasn’t hearing the music. His mind was solely focused on the what he was about to do. *He had thought about buying a package of diapers for himself for a long time, but never got the courage to. Now as he got closer to his objective he felt the butterflies increasing in his stomach with each passing mile. Before he knew it he was parked in front of Rite Aide. “All right Sam you can do this.” Wow giving yourself a pep talk out loud, that’s just sad, Sam thought to himself.

********He took a look around the parking lot trying to get a feel for how busy the store would be based on the number of cars. *Much to Sam’s chagrin the lot is about half full, he lets out a sigh as he heads into the store. Sam felt sick to his stomach as he stepped through the sliding glass doors. *He felt a little bit of relief when he looked around and saw that it wasn’t nearly as full as he had thought. He grabbed a basket and started making his way through the aisles, as non-chalantly as he could. He hoped that no one would pay him any attention. After pretending to look in other aisles, Sam worked up enough courage to finally step foot into the incontinence aisle. He wasn’t exactly sure what he was looking for. In all the stories he had read the characters frequently used attends or cloth diapers. But here in the store all he saw was Depends and store brands. He had at least heard of Depends so he decided to go with that brand, but that hardly narrowed down the selection. He wasn’t sure if he wanted briefs which looked like a giant pull-up, adjustable briefs which he would have said was a standard diaper other than having four tabs instead of two, and then something called fitted brief which had six tabs and said offered the most protection. But they looked like they were made of plastic, not the softer cloth looking material of the adjustable briefs. *

********Sam must have lost track of time pondering over what kind to get, the selection was just so overwhelming. Before he knew it there was a store employee standing behind him. “Can I help you find something?” The sound of a question being asked so close behind him made him jump. “Oh! I’m sorry I didn’t mean to frighten you. Is there something in particular you are looking for or any questions you have regarding our adult incontinence supplies?” Sam slowly turned around trying to think of what to say, when he saw who the voice was coming from he simply wanted to die.

********Standing before him was a beautiful woman with a smiling face. *Her dark mahogany hair was pulled back in a ponytail. She had a light skin complexion with stunningly green eyes, and a very warm smile. *She was bent over with her hands on her knees as she spoke to him. This enabled Sam to see down her shirt into cleavage that was struggling to be contained by the tight white tee and dark blue Rite Aide vest she was wearing. *Her name tag read Jenny. Sam didn’t know what to say, he just didn’t want her to know he was shopping for himself and he didn’t want come away empty handed. He tried to compose himself but he could feel the heat in his face from blushing and his voice cracked when he went to answer. “I was uh wondering if you guys carried goodnites?” despite his voice cracking, Sam felt like he dodged a bullet, certainly she would think he was buying the goodnites for a sibling.

********“Why yes we do. You will find those over here in our baby aisle. If you follow me I can show you.” With that she stood up and took Sam by the hand to lead him to the correct aisle. Sam was taken back by having the gorgeous woman lead him around the store by the hand, how young did she think he was. Moments later they were standing in front of several shelves stacked with diapers. *There were several young mothers in the aisle who only paid Sam minimal attention. “Here these should fit you.” Jenny stated as she took a package of XL boys goodnites from the shelf.********

********Sam could feel himself blushing again, obviously his plan failed and Jenny thought it was he who needed the goodnites. “Actually, uh, they are for my kid sister.” Sam said, his voice cracking again as he spoke. He knew he was blushing harder than ever, but he was hoping Jenny would believe him in spite of it.

********Jenny gave him a quick glance and then smiled. “Okay, what size does your sister wear?” Sam thought she said sister with a slightly incredulous tone, but what out of there quickly so he didn’t push the issue.

********“Umm she is about my size.” He responded still blushing. He met her gaze for a second before looking away.

********“Right” said Jenny with a knowing smile. “Well is there anything else you need, baby bottles, pacifiers, lotion, wipes, perhaps?”

********“No, just the goodnites.”

********“Okay then lets grab them and ring them up.” Jenny grabbed a package of girls XL goodnites from the shelf and once again took Sam by the hand to lead him up to the checkout. Jenny opened up a cash register that wasn’t in use and rang Sam up. “So you out running errands for your mom?” Jenny asked as she was printing the receipt.

********“Uh, Yeah.” Sam replied emphatically, happy that she finally seemed to believe him.

********“Your mommy must be so proud of her big boy.” Jenny said in a baby talk tone as she bagged the goodnites, causing a fresh wave of blushing from Sam. “I double bagged them to help hide what they are for you. Come back if you have anymore diaper questions and have a nice day.” Jenny said with a smile while she handed the bag over.

********“Thanks.” Sam quickly took the bag, paused ever so briefly to look at the Jenny’s girl next door beauty one more time before bolting out the door. *Once he was in his car he breathed a sight of relief. The trip hadn’t gone anything like he planned but he came away with something close enough to diapers to be happy and the interaction with Jenny had left him very excited. It was two thirty when Sam got home. The trip had taken much longer than he expected but at least he didn’t have to explain being home half a day early. Sam was surprised to see his mom’s car missing from the drive as he pulled in. Must be out shopping he thought. This would mean he could a smuggle his purchase in safely and hide it in his room before she got back.

********Once in his room Sam immediately stripped and slid one of the goodnites up his legs. *They fit perfectly thanks to his small frame. He felt snug and secure in them. They were everything he hoped for and more. He was so contented with them that he didn’t even mind the pink flowers and butterflies on the front. He pulled his pants back on and stashed the package under his bed. Just in time too, he thought as he heard his mother’s car pulling in. *He quickly checked himself in the mirror for any tell tale bulge. Finding none he went to his bedroom window to look out and see if his mom needed any help with groceries. What he saw turned his stomach.

********Getting out of his mother’s car was the next door neighbor. Who quickly disappeared across the street into his own home. Sam felt like crying. He knew both his parents cheated on one another but he had never actually seen the evidence. He had heard them fight over it at night though. His mom accusing his dad of working long hours on purpose to be with his secretary and his dad accusing her of having numerous boy toys. Sam heard the front door open and walked into the living room just in time to see his mom step in.

********“Sam!” she said in a surprised tone “what are you doing home? I didn’t see your car in the drive”

********“It’s in the garage. I got let out early, but I am not feeling good so I think I am just going to go to bed.”

********“Ok sweetheart.” Sam’s mother kissed him on the head before disappearing into the kitchen, presumably for a drink. Sam walked back to his room feeling like crap. His phone was glowing from a text message. It read:

Sam can you come into class at eight on Tuesday. I have a project I want you to work on Ms. E.

Sam didn’t know what Ms. Easterfield needed help with and was too distracted to really care. He replied back with a simple “Sure” before crawling under his covers. He fell asleep clutching his knees to his chest, with his school clothes on. His face was red from crying.


Across town Ms. Easterfield was on her computer researching Sam’s online activities. She had a legal pad she was taking notes on. So far she found Sam spent the most time on a site called SissyKiss and one called Dailydiapers. His searches revealed that he liked to read stories about strong women taking care of helpless males in their lives. Not a true Oedipus complex, she thought as all the women served as surrogate mothers and not actual blood relations. *She also noticed that alot of the stories involved female dominance beyond just babying as they included a phallic symbol of some sort that was thrusted upon the male, whether it me a vibrator, enema, or even a abnormally large pacifier. Seems he has a deep need for complete trust and intimacy in addition to someone taking control . Ms. Easterfield took of her reading glasses and closed her computer. She was starring off into the distance contemplating her next actions. Her thoughts were interrupted by a female’s voice calling out to her from the front door. “Amy, honey, I’m home.”

“In the living room love.” Ms. Easterfield called back.

Chapter 4

********Ms. Easterfield woke up bright and early Tuesday morning. *She wanted to make sure she had plenty of time to get things set up at the school before Sam arrived. *She had spent the whole weekend shopping both in stores and online. *She was bummed that the online stuff would take awhile to arrive but she had more than enough supplies to last until they got delivered. She found herself distracted as she took her morning shower, as she thought about the coming day, which brought a ever present smile to her face. Amy stepped out of the shower and wrapped a towel around her body as she walked to the master vanity. She got ready for the day applying her usual makeup and doing her hair. An hour after Amy had woken up she was finally ready to go. Amy was just about out of the room when she heard a stirring coming from the bed.

********“Amy, honey why are you leaving so early? Its only 7:15 and you don’t have a class till nine.” asked a groggy voice that was still hoarse from just waking up.

********“Sorry babe, I didn’t mean to wake you, but remember I told you I have some special preparations to make today.” Ms. Easterfield replied as she walked over to the bed to give her partner a goodbye kiss. She bent over and kissed the soft lips. “Sorry again for waking you so early.” Amy whispered.

********A long slender arm reached up from under the covers and wrapped around Amy’s neck. When the kiss broke the arm pulled Amy’s head lower and the soft lips now free from the kiss whispered into Amy’s ear, “I know how you can make it up to me.”

********Ms. Easterfield smiled pulling away, “I wish I could but I don’t have the time right now.”

********A soft “bummer” escaped the lips before they and the arm disappeared back under the covers and rolled over escaping the light that was pouring in through the bedroom door. “I expect a detailed report of how this special project that is taking my lover away from me, goes.” The lump under the covers called after Amy as she left.

********Amy was glad she had loaded the car up last night because the unexpected exchange in the bedroom had taken up about five minutes she wasn’t planing on.


********Across town Sam tossed and turned in his sleep. He had had a miserable weekend and spent most of it in his room not wanting to face either his mother or father. The only good part about the weekend was he finally had his own diapers to wear even if they were just girl’s goodnites. He spent the entire weekend in them and especially enjoyed falling asleep in them. Drifting off, feeling the extra padding around his hips and crotch, it made Sam feel safe and secure. He had been getting wonderful sleep in them but for some reason Monday night/Tuesday morning was a different case. He kept dreaming that he was in school trying to complete something but he didn’t know what it was he was supposed to be doing in his dream. Finally at 7:45 he bolted awake, Oh No! he thought he was supposed to go in early today. Sam looked over to his clock great, ten minutes to get ready and five to get there.

********Sam threw back his covers and raced through his morning routine. *He didn’t even bother to change boxers as he threw on a pair of jeans and a tee. Not having time for a shower he just rinsed his long hair under the sink. He wore it in a style reminiscent of Jim Morrison. He combed it out and the shook it dry in order to achieve that purposely messy look. After brushing his teeth he grabbed his bag and went out the door. Sam didn’t even remember he was still wearing the goodnite till he was sitting at a red light, it was also at this time that he realized he didn’t take his morning pee. *Great this is just what I need after my bad weekend he thought. Even though he was enjoying wearing diapers, he hadn’t wanted to use one yet. Just a few more blocks, I can make it, Sam told himself.

********Sam breathed a sigh of relief as he pulled into the school’s parking lot. He was mentally running through his game plan as he climbed up the stairs to his classroom. I’ll drop off my bag in Easterfield’s room and then go to the restroom and because it is early enough I should have enough privacy to dispose of the goodnite there.

********Ms. Easterfield had just finished putting away the last of the supplies when she heard Sam’s footsteps outside the door. *The classroom had cabinets that ran the length of the room on the far exterior wall and the back wall. All the cabinets had locks on them so that teaching supplies could be locked up at the end of the day. The cabinets were high and came up to most students’ naval if not higher, a fact that Amy greatly appreciated because it meant they were at about her waist. *The top of the cabinets were a forest green formica counter top. *Amy had spent the morning clearing out the two cabinets directly behind her desk so that she could lock the new supplies in them.

********Amy opened up the key logger program on her computer just as Sam stepped through the door. *“Good morning Sam, are you feeling better after your long break?”

********“Uh, yeah, thanks.” Sam replied slightly sheepish over cutting class so early in the year.

********“Will you go ahead and shut the door, I don’t want any distractions because we need to get this done, before class.”

“Sure.” Sam closed the door behind him as he walked to the back of the classroom and set down his book bag. “So what’s this project you got for me?”
********Ms. Easterfield minimized her computer screen, she was planning only using it as evidence if Sam tried to deny it. “Well Sam pull up a chair I want to talk to you about something.”

********Sam started to get nervous as he pulled over the extra computer chair that was in the room. He wondered if he was in trouble for cutting out early on Friday, but that had been Ms. Easterfield’s idea, so it couldn’t have been that. Maybe some student was accusing him of unfair grading on a test. *Either way Sam was pretty sure he had not done anything major wrong.

********Ms. Easterfield leaned forward in her so that she was both closer to Sam’s face and so that she was closer to his height. “Sam I want to talk to you about your internet activity this past week.”

The moment she said internet Sam went rigid in his seat. *How much did she know? Did she just see the screen on Friday? Why hadn’t she said something then? No he must have forgotten to clear the browsing history earlier in the week. Sam forced himself to remain silent so he wouldn’t give her more information than she already had.

Amy would have had to been blind to not see, the immediate change in Sam. He looked like a deer in the headlights. She felt bad for him as he turned ghostly pale. “Sam, I’m not mad.” She said while placing a hand on his knee. She could feel how rigid he was under her touch. Her words did nothing to ease him. She pressed on in a motherly voice. “Sam, it’s okay, really I’m not judging you. From what I’ve seen of you around the school, honestly I’m not all that surprised. I’ve watched as you have hung out in all the different circles, from the in crowd to the stoners, the jocks to the nerds, but I’ve never seen you actually develop friendships. You have closed your self so far off and only subsisted on shallow acquaintances. They’re enough that you always have someone to talk to in class but I’ve also witnessed as you have eaten lunch alone every day while you listen to your ipod. You long for closeness but don’t trust anyone so you escape into this fantasy world.” Ms. Easterfiled gestured at the computer. “If I had to guess I would say you have a strained relationship with your mother and an even worse one with your father.” Amy stopped suddenly, as she saw Sam’s eyes starting to mist up.

At some point while she was talking Sam had switched from being a statue with a scared look to small hurt little boy. She opened up her arms to embrace him. “Its okay Sam, come here, it’s okay.” Sam slowly got up from where he was sitting and walked over to hug Ms. Easterfield. He was shocked when she didn’t just hug him, but picked him up and held him in her lap. Sam buried his face in her shoulder as the tears came faster. Amy had only been meaning to get him to open up, she hadn’t expected all this. She had apparently hit the nail on the head and in doing so driven it through the thin protective crust that Sam had been hiding behind. “Ssshhh, its okay, little one.” She whispered as she stroked the back of his head and hair with her right hand. “It’s okay.” She continued whispering. She was rubbing his back with her left hand, while Sam cried into her shoulder. Sam was aware at how infantile he was acting, crying into this beautiful woman’s shoulder whilst she held him and rubbed his back. He was sure the size difference would make him look like a small child, but he didn’t care. He was feeling like someone actually cared for him for the first time, in a long time. Ms. Easterfield’s hand felt good as it moved up and down his spine.

She held him like that for probably five minutes. Her constant rubbing had caused Sam’s shirt to ride up. Instead of pulling it back down she simply slipped her hand underneath it and continued soothing him. Sam didn’t mind the added warmth of her hand being directly on his skin. It only made him feel more secure. Amy noticed an odd fabric texture just above Sam’s waistband. She lifted her head from where it had been resting against Sam’s and looked down. She immediately recognized the waist band of the diaper Sam was wearing. “Sam honey, are you wearing a diaper?” Amy asked in a hushed voice.

She could feel Sam tense up in her arms, he held his breath for a moment before a fresh round of tears burst forth. Sam just wanted to disappear, he could not believe this was happening to him. He tried to bury his head deeper into Ms. Easterfield’s shoulder and block out reality. Ms. Easterfield continued stroking his hair. “Hey, hey, it’s okay, it’s okay. I already told you I’m not upset. Okay?” Sam just continued to cry. Amy gently pulled Sam off her shoulder so she could look him in the eyes. Sam kept his head down and stared at the floor. Amy ducked her own head to meet his gaze, but he shifted his eyes away. “Hey look at me, Sam.” Sam slowly raised his head and met her eyes. “I’m not upset, do you understand?” Sam nodded. “Now are you wearing diapers.” Sam dropped his head but nodded again. Ms. Easterfield lifted his chin with her hand. “Look at me sweetie and use your words.” Sam held her gaze. “Now are you wearing diapers?”

“Yes” came the barely audible answer.

“Yes, what?” Ms. Easterfield pressed.

“Yes, I am wearing diapers, Ms. Easterfield.” Sam burst into tears as he said the last word.

“Ssshhh, ssshhh” Ms. Easterfield cooed as she clutched him back to her shoulder. She brushed his hair back over his ear and began whispering to him. “Hey, it’s okay, Sammy. See you’ve now said your deepest darkest secret and I’m still here. It’ll be okay.” She continued to hold Sam for a few more minutes until he quieted it down. “There now aren’t you glad that you have said it out loud?” Amy could feel Sam shake his head yes into her shoulder. “Are you feeling a little better?” Again she felt her shoulder shake with Sam’s confirmation.

“Ms. Easterfield?” Sam pushed himself off her shoulder so he could look at her.

“Yes honey?” Ms. Easterfield looked at the small boy she had been holding in her arms. Sam’s eyes were bloodshot and his faced was stained with tears.

“I need to use the bathroom.” He said breaking his gaze.

“Okay honey. Its all right.” Amy lifted Sam up off her lap and stood him on the ground in front of the chair. She got up and kneeled down in front of Sam. Sam was confused when she started taking off his shoes.

“What are you doing?” He asked in a meek voice.

Amy stopped and looked up at him. “Do you trust me Sam?” She asked looking into his eyes. He nodded. “Good” She reached into her pocket and produced a pacifier. Which she placed in Sam’s mouth. He didn’t resist the pacifier but rather took it and began sucking on it. “Now its obvious that something vital is missing from your life right now, so I am going to give you that. Okay?” Sam nodded his again. “Okay” Amy resumed undressing Sam. She removed his shoes and socks, followed by his shirt. Next she began to take off his jeans. She was surprised when she undid his fly and found a girl’s goodnite around his waist. “Interesting” she muttered.

“I can explain” Sam said around the pacifier.

“Quiet honey, you don’t need to explain anything. Now come here sweetheart.” Ms. Easterfield picked Sam back up and sat him down in her lap. She was sitting in her computer chair with Sam in her lap, facing outwards. Sam could feel Ms. Easterfield body heat radiating off her. It felt nice on his bare skin. “Sam can you do me a favor?” Sam turned his head so he could see Ms. Easterfield’s face. “I want you to wet your diaper for me.” Sam’s face took on a worried look. “You, need to do this, honey it will help us build trust.” Sam nodded agreement.

Amy placed one hand on top of Sam’s diaper. “Go ahead honey.” Sam relaxed his bladder and almost immediately he started peeing. A quiet hissing sound could be heard as Sam filled his diaper. Amy could feel the warmth spreading under her hand has the diaper soaked up the pee. Her hand was cupping the front of the diaper, she noted the way it felt as the diaper expanded in her grasp. “Good baby, now as a reward, I’ll help you de-stress.” Ms. Easterfield began moving her hand over the front of his diaper. Sam immediately felt himself getting hard. He let out a small moan as he grew inside of his diaper. Ms. Easterfield continued to rub the front of the diaper up in down with her right hand as her left arm held Sam in her lap.

Sam felt himself slipping into ecstasy, his hands grasped onto the arm rests of the chair and he used them to hold himself tight against Ms. Easterfield. He rolled his head over his left shoulder till his cheek was resting on Ms. Easterfield’s breast. Sam began to lift his hips up increasing the pressure being put on the front of the diaper. He also began to suck furiously on the pacifier in his mouth. Amy slowly built up speed as she listened to Sam’s breathing increase. When she sensed him reaching climax she quit rubbing and squeezed his head through the diaper. Sam all of sudden went rigid in Easterfield’s lap, his arms locked at the elbows as his pelvis hoovered inches off her lap. He let out a prolonged moan before collapsing back down onto Ms. Easterfield.

Amy sat there with Sam on her lap, listening as his breathing returned back towards normal. Soon she felt him breathing slow deep breathes and heard a soft snoring sound coming from his throat. She kissed him on top of his head as she whispered, “you poor baby you must have been exhausted, it’s okay though you can sleep tight now.” She gently repositioned him so his head was resting on her shoulder and his stomach was against her. Deciding Sam was out cold and likely to remain that way most of the morning she gently stood up while holding him tightly to her so he didn’t slip. Amy walked over to the counter top and reached into one of the cabinets to get out and extra long changing pad. It was the kind with foam padding inside, it was meant to be on top of the main changing table. She laid it out on the counter with her left hand and then gently laid Sam down on top of it.

Amy tore the sides of the goodnite open and slipped it out from under him. She then cleaned him up with wipes and placed a new diaper from one of the packages she bought under him. Pulling it snug, she fastened it into place. Amy was grateful Sam wore his jeans loose as the diaper was quite a bit thicker than the goodnite he had been wearing. She proceeded to dress him. Not once did Sam stir from his heavy sleep, he just kept sucking on the pacifier in his mouth. He even slept through having his shirt put back on. Finally Ms. E had all of Sam’s clothes back on and she couldn’t help but think he looked so cute as he sucked on his pacifier. She glanced at her watch, 15 minutes till first hour would end. She decided she better hurry up and get him to the couch in the teacher’s lounge and get all the baby supplies put back away before the kids started to fill the halls.

********Picking Sam up proved to be the most difficult part of the whole process but thanks to her size on him, Amy was able to lift Sam back up off the counter and carry him across the hall. Once in the teacher lounge, she gently laid him down on the couch that was there and covered him with a blanket. She had decided that if anyone asked she would tell them Sam had went to lay down with a headache and must have fallen asleep. The last thing Amy did before heading back to her class was remove the pacifier. She was kneeling down beside Sam as she pulled it out. Then she brushed his hair back and kissed him on the head. “Sleep tight baby.” She whispered, “I’ll be back to check on you in a bit.”

********Without opening his eyes Sam muttered back “Thank you mommy, I love you.” Amy smiled at his subconscious word choice.

********“Mommy loves you too baby.” With that Ms. Easterfield got up and headed back to her classroom.

Chapter 5

********Sam woke up to someone gently rubbing his shoulder. At first he was extremely groggy and disoriented, he had been having the most wonderful dream about his teacher. He dreamt she had found out his secrete and accepted, no embraced him rather for it. Now he struggled to keep his eyes closed not wanting to lose the dream and face reality. He wished his mom would just let him sleep so he could go back to dreaming Ms. Easterfield was his mommy. “Sammy honey, it’s time to wake up.” Came the hushed whisper of his angel. That voice, that glorious voice burst through into his mind like a sunshine after a long cold winter. Was it possible that it wasn’t a dream. “Come on Sammy.” The rubbing became a little harder. Sam slowly opened his eyes and was greeted by Ms. Easterfield’s face smiling down at him. She was sitting on the edge of the couch beside him, and rubbing his shoulder. Sam looked around and realized he had no clue where he was. He was about to speak when he realized there was something in his mouth. He felt it with his tongue, it was bulbous and had a rubber taste to it. He soon remembered it was the pacifier from earlier. *

********“Sorry to wake you, sweetheart, but there isn’t a lot of time between classes and I wanted to get you cleaned up and see how you are feeling.” Amy pulled the blanket off him and then reaching down, picked Sam up. It was much easier this time as he wasn’t just dead weight. Standing she held Sam to her chest with one arm under his butt. He wrapped his legs and arms around her like a small child, as she carried him into the faculty bathroom that was inside the lounge. She locked the door behind them as she sat Sam down on the toilet. Ms. Easterfield took a cloth handkerchief from her purse and wetted it in the sink. Then she set to work cleaning the tear stains from Sam’s face.

********Sam sat on the toilet in a daze as the woman he so often fantasized about lovingly cleaned his tears with gentle wipes. “Sammy honey, are you feeling better?”

********Sam nodded, not wanting to speak thinking his voice would sound hollow and tinny next to her angelic soprano. “You slept through first and second hour, do you want to continue sleeping or would you like to come and watch while mommy teaches?”

********Sam was briefly taken back by Ms. Easterfield referring to herself as mommy, but then he thought he could remember calling her that earlier when he was sleeping. Either way he liked thinking of her like that. “I want to watch mommy teach.” Sam said around his pacifier.

********“All right Sammy, but before we go back out do you need to be changed?”

********Sam shook his head no and with that they both left the restroom and headed across the hall towards class. Sam took his seat at Easterfield’s desk, while she stayed at the front of the room preparing and overhead with notes. Sam already missed the feeling of the pacifier in his mouth even though it had only been minutes since Amy had removed it in the restroom. Sam watched as all the students filed in and he couldn’t help but smile to himself at the fact none of them had a clue as to the new relationship between him and Ms. Easterfield.

********“You must have had one terrific weekend if you are still smiling on Tuesday morning.” The voice snapped Sam out of his thoughts. He turned to see Kayla in her seat looking at him.

********“Actually no, it was pretty crappy. In fact it was crappy enough that I now look forward to school. How about yours?” Sam asked hoping to keep *the spotlight off of himself.

********“Well originally I would have said crappy, but some how I don’t think it would even come close to being as bad as yours, so I’ll go with boring. I pretty much unpacked all weekend. Do you want to talk about why yours was so bad?” Kayla asked looking concerned.

********“Thanks, but no thanks, I kind of just got over it a little bit ago, let’s just say things have been better between my parents and leave it at that.”

********Kayla kept the conversation light out of respect for Sam’s wishes as they waited for class to start. *She found it was easy to talk to Sam and he wasn’t like most of the other guys she had known.

********“All right class let’s begin.” came Ms. Easterfield’s voice a few moments later from the front of the room.

********“In all seriousness though Sam I hope you have a better day today.” Kayla said before turning around and opening her binder.

********“Thanks” Sam whispered back trying to be considerate of Ms. Easterfield.

********Once class was under way Sam’s thoughts turned to what had transpired that morning between him and Ms. Easterfield. The last thing he remembered was collapsing on her chest in exhaustion after she had given him that wonderful reward. *He wondered when Ms. Easterfield had changed him and how on earth could he have slept through that wonderful experience. He wondered what she had changed him into. Had Ms. Easterfield found the extra goodnight he had been keeping in his backpack. He had stashed one there when he first bought them so he would have easy access to at least one if he couldn’t get to his main stash. *Now that he thought about it, whatever she had put on him was also thicker than the goodnites he had been wearing. Sam pondered these things and others as class continued on. It wasn’t until he heard Kayla’s voice again that his mind re-centered on the present.

********“Here you go Sam,” Kayla was holding a scrape of paper towards him with numbers scrawled on it. “If you ever want to talk about what’s going on with your folks give me a call and we can get coffee or go for a walk or something.”

********“Hey thanks, I might have to take you up on that.” Sam said not able to contain his excitement as he took the paper scrap from her. *It was the first time he had gotten a girl’s number and he was bursting with joy. Kayla couldn’t help but smile at the stupid grin on Sam’s face.

********“Have a good day Sam, I’ll see you tomorrow.” Kayla said as she headed towards the door.


********Amy smiled at Sam from the front of the class, while she watched the exchange transpire between him and Kayla. Once all the students left she reverted back to her mommy role with Sam. “Care to stay here and have lunch with mommy, sweetheart?” She cooed at him. Sam eagerly shook his head. “Kay, then you wait right there while I go get it from the teacher’s lounge.” Sam wondered what he would be having for lunch as he watched Ms. Easterfield leave the room. He didn’t have to wait long as she returned shortly with a cooler.

********Amy shut and locked her classroom door, a practice not completely unheard of, when faculty didn’t want their lunches interrupted by students popping in. *Ms. Easterfield placed the cooler on top of the cabinets behind her desk and began unlocking one that contained Sam’s baby supplies. *“Mommy, where did the diaper I am wearing come from?” Sam asked while he watched Amy unlocking the cabinets.

********“See for yourself honey” she said as she opened up the one of the doors. *Sam’s eyes went wide as he looked in and saw several packages of diapers, along with baby wipes and other changing supplies.

********“Is all that for me?” He asked not willing to trust what he was seeing.

********“Yes, and we will discuss that while we eat.” Amy said hopping up so that she was sitting on one of the counter tops. The counter top immediately behind her desk had a cushion that was as wide as the counter top and and about eight feet long. Amy had purchased it so that the students could sit up there and read when they completed their work. Now it would serve an entirely new purpose. “Come here Sammy.” Sam got up and walked over to her. Amy leaned forward and lifted Sam up and sat him next to her. “Go ahead and lay down with your head in Mommy’s lap so I can feed you.”

********Sam immediately complied. Ms. Easterfield cradled his head in one arm and removed a baby bottle of milk from the cooler with her other hand. “For the baby we have to bottles of protein powder mixed with milk. You will find it quite filling I imagine. *Also the nipple has been modified so that it will actually flow at a descent rate, that way baby’s jaw doesn’t get tired. And for mommy a nice yogurt parfait.” Amy pulled out a parfait she had made earlier at home. “Now drink up baby, while mommy goes over some ground rules.” She said as she placed the nipple in Sam’s mouth.

********“First I am more than happy to be your surrogate mommy as long as you need me to be, but that means I expect you to start getting here at 7:45 each day so I can diaper you before my first class. *When you are diapered I expect you to wet them just like a baby. From now on you will eat lunch with me and take a nap during your free period, since that corresponds with my prep hour there will be no issues with you taking it in here. All this treatment must remain a secrete though for obvious reasons. Finally I don’t want you keeping any more secretes from me. So what do you say, do you want me to be your mommy?”

********Sam nodded yes as he continued to drink his bottle. *“Good I am so glad to hear that. Now why don’t you tell me why you were so sad this morning.” Sam then began to recount what had happened that weekend and how he didn’t sleep well that night and woke up late. He ended with how this morning was the first time he felt love in a long time. “Why were you wearing a girl’s goodnite and not a guys?” Amy asked as she took the now empty first bottle from Sam. Since she had finished her lunch she was going to feed Sammy the second bottle.

********Sam told her about his shopping trip. Amy would remove the bottle so he could talk and put it back when he was thinking or she was talking. “But that’s not all of it is it Sammy?”

********“What do you mean?” He asked slightly confused.

********“A lot of the stories you read online have males either being forced to dress in girls clothes or choosing to dress that way themselves.”

********“I guess part of it is because of this whole thing with my parents. Since I’m a guy I feel like I am not allowed to show any emotion over it.”

********“So you feel that role playing as a girl you would be able to break that taboo then?” Sam nodded. “Well then Sam, I think that it is important that you get to express that side of you, but we will figure that out latter. For now I want you to just finish your bottle and take a nap, you must still be tired from last night.”

********Sam couldn’t argue with her, even now as he finished the last quarter of the bottle he felt his eye lids getting heavy. *Amy began to humb a lullaby to Sam, and with in minutes he was asleep. He continued to suck on the bottle even after he closed his eyes, and when it was empty Amy replaced it with his pacifier. She sat there with Sam sleeping in her lap for a long time, as she thought about her new baby and what the school year would look like. Amy not having any kids of her own loved her new found role, but wanted to help Sam more than anything. When her next class was getting close to beginning she gently lifted Sam’s head off her lap and slid down. She told her class that Sam hadn’t been feeling well and that’s why he was laying down. Luckily her next two classes were both watching movies so the room stayed quiet and dark. It was the end of the school day before Sam woke up again. Amy reminded him to be back in time for first hour tomorrow as he grabbed his stuff to leave. Sam drove home thinking about how awsome this year really was turning out to be.

********When Amy got home she was greeted with a surprise of her own. Her partner was waiting in their bedroom in a black silk robe. “I thought you might have time to make it up to me now.” She said as she let the the robe drop, revealing a emerald green lace bra and pantie set. Upon seeing her Amy could only smile.

********“So this is what you do all day when I’m at school. Lay in wait to ambush me dressed like that.” Amy asked grinning.

********“Would you rather I do something else?” Her partner asked with an impish smile.

********“Not at all.”

********An hour latter, and the lace undergarments and Amy’s work clothes were long since forgotten and both girls were spent and laying in bed cuddling. Amy had opted for little spoon this time and was enjoying the feeling of her partner’s ample bosoms pressed against her back.Amy felt very loved in her partner’s expert hands, which were currently cupping Amy’s own ample breasts. “You promised to tell me how it went today.” She whispered in Amy’s ear. So Amy filled her in . “I think I would like having her as a little girl.”

********“Me too,” Amy agreed, “If only.”

Want to read more?  The full 31 chapters (and counting) can be found on my blog by clicking the link : Ms. Easterfield's Baby  Actually the rest can also be found throughout this post but a glitch has distributed it all over the place (no really the remaining chapters are on like 5 different pages and they are out of order). 
The Next Page
Last Post
405 posts
These lovely people support all the features in Sissy Kiss to contribute to our community! So it would help so much if you could check them out, and say your from Sissy Kiss. Some even give discounts, or free gifts by mentioning it!
Add your message here..
0 - 25 of 398 posts
Page 1 of 16
Go to the page:    
'Lil Melissa
I just luv this story! It was up a month or so back; what happened? Please keep going!
All right ladies just added another chapter, hope you enjoy. And seriously if you see mistakes let me know. Thanks
Besides some spelling errors which were little mistakes I can't wait for the other chapters.
Please add more soon!
great story so far feep it going
I want to quickly address a common question I'm seeing alot in the comments, that is why was the story pulled briefly. It wasn't Christie Luv's doing it was my own. I had some outside stuff going on and I yanked all my posts when I was upset. I guess baby had a tantrum :) Then when I went to repost it, I saw it as a perfect opportunity to tweak some things. Sorry for anyone I may have upset.
You made me cry when you tuck this story, but now that it is back up I am happy again.
You made me cry when you tuck this story, but now that it is back up I am happy again.
 You made me cry when you tuck this story, but now that it is back up I am happy again. 
dreamer of frilly
Its been a while since a story that has made me laugh so much. Probably because i identify with the things he's going through. Will keep this one marked i can't wait to see the rest
So glad to see this story back. It was shaping up to be an all time classic :)
I can't wait to read more, im loving it 
Mina Silverwind
You have an excellent writing style, your stories get better with time, please keep up the good work, and your stories bring a smile to my face.
success is not how many times you win but is instead our ability to learn that we win by never giving up when times are tough.
Just added the latest installment, and I know it doesn't contain what most of you guys want but some character development is necessary every once and a while.  Plus I really enjoy writing for Patrick and Chloe
Just put up another chapter. Hope everyone likes it
Best chapter yet keep up the great work
'Lil Melissa
Luv it! Everyone should have someone like that in their lives - wish I did - to help smooth out the rough patches. Curious to see where Kayla fits in with things. ;) Great work!
I just read Chapter 4 and I love it! I can't wait to read the completly new chapter :)
Lots of tight and long hugs!
Positively love it
Chapter five will go up tomorrow girls. Then after that it will be completely new material, Yay!
0 - 25 of 398 posts
Page 1 of 16
Go to the page:    
What kind of post would you like to make?
To post certain kinds of posts, like images, audios, or videos you need to be signed in first.