Story: Chrissey’s Summer in Diapers – Part 5

By | February 22, 2016

The two of them laughed as Ms. Johnson carefully lifted her heavy breast out of the lace cup of her push-up bra, positioning it before Timmy?s brightly blushing face.

?Here you are Sissy,? she said soothingly, ?Time for baby?s milk.?

Timmy squirmed uncomfortably and made a half hearted attempt to move away but Ms. Johnson easily held him in place and she ran her erect nipple across Timmy?s quivering lips.

?Open up Timmy, time for num-nums!?

Timmy closed his eyes and shook his head no but before long, he acquiesced, taking the erect nipple in his mouth and submissively suckling on the tremendous breast being pushed against his face.

?Thaaaat?s it,? Ms. Johnson said in a whisper, ?suck like a good little baby.?

I was whimpering now with jealous impatience, fidgeting while I waited my own turn to nurse from Crystal?s fantastic chest. She smiled down on me warmly and looked me directly in the eye.

?Don?t worry Babykins, I haven?t forgotten about you.?

With that, she brought the warm bottle of milk up to my mouth and pushed the rubber nipple against my lips. I whimpered in protest but she slid it across my lips until I surrendered to her efforts. Looking deep into her pretty eyes, I was forced to suck from the bottle, taking in mouthfuls of warm milk and swallowing it while she kept the bottle firmly in place. I moaned in protest but the big rubber nipple filling my mouth prevented anything intelligible from coming out. Meanwhile, Crystal?s hand wandered down to softly stroke the smooth surface of the front of my diaper, sending electric shivers through my body.

?That?s mommy?s little baby,? she cooed as she smiled down at me, ?Drink your ba-ba like a good little baby.?

I blushed deeply as I submitted meekly to her ministrations, yet I felt intensely frustrated that I wasn?t being allowed to nurse from her breast directly. They were so close, yet I couldn?t see underneath her thin sweater that was stretched tightly across her ample bosom. Looking across at Timmy, I saw that his face was dwarfed by Ms. Johnson?s titanic boob, and I watched with fascination as he sucked obediently from her. She was cooing down at him, softly encouraging him while still treating him very babyishly. I had to admit, he looked rather cute with the pink lipstick kisses still covering his blushing face. His legs were slightly apart, due to the thick bulk of his naptime diapers, which Ms. Johnson was also slowly stroking. Even her hands were sexy, with her creamy skin and long manicured nails. I watched as she softly rubbed the front of Timmy?s diaper, making him mewl like a kitten. His legs were bare except for his usual pink Keds and anklets he was wearing and I noted the smooth, hairless skin of his thighs. His feet were fidgeting slightly as he tried to cope with the raw sexuality of Ms. Johnson and my heart beat faster just watching him. He looked so completely babyish that I couldn?t ever imagine him growing up.

After finishing off one breast, Ms. Johnson, tucked it back into its lace cup and pulled the other out, forcing it into Timmy?s pouting mouth, much as she?d done before. I squirmed in frustration as I sucked helplessly from the warm rubber nipple in my mouth. Looking up at Crystal?s pretty smiling face, I whimpered in protest but she merely smiled back at me, holding the bottle firmly in place to prevent me from refusing it.

When Ms. Johnson finally finished with Timmy, after ten maddeningly long minutes, I thought my chance had finally come. But rather than producing one of her delicious breasts for me, she instead buttoned up her blouse and we traded positions over the two women. Now Timmy was being cradled by Crystal and Ms. Johnson was holding me. I began whimpering louder, desperate to get my lips around one of her gorged nipples I saw poking rigidly through her blouse but she looked at me determinedly and firmly placed the bottle back in place for me to drink from. I didn?t want any part of it, especially as I watched Crystal begin to slowly unbutton her sweater from the front, revealing two massive melons, restrained only by her lacy white bra.

?No?? I whimpered weakly to Ms. Johnson, ?No, please?I want? I want??

She cut off my protests by pushing the wet rubber nipple between my quivering lips, forcing me to suck again from the large bottle. I choked back a sob but I sucked submissively on the baby bottle, taking more and more of the hated warm milk.

Timmy tried to shake his head no as Crystal delicately offered her big, bare breast to him but she reached behind him and pulled his head forward, forcing him kiss her dark nipple. Her breasts were so bursting with milk; I could see it already starting to dribble down from the tip of her nipple where she slowly, tantalizingly rubbed it across Timmy?s lips. Whimpering like a girl, he finally submitted and took her breast into his mouth where he began suckling in defeat.

During this time, I was kept prisoner in Ms. Johnson?s arm, my head resting against her big, soft bosom while she made me drink the remainder of the bottle. With each frustrating moment that passed, I became angrier and angrier that Timmy was getting sexually pleased and I wasn?t. I wanted to fight back but when I looked up into Ms. Johnson?s beautiful but stern features, I got butterflies at the mere idea of rebellion. Finally, I finished the bottle of milk and she slowly withdrew it from my mouth, a line of drool connecting the nipple to my lips as she pulled it away. I thought she?d let me up but with a cruel smile, she produced another baby bottle, also full of milk!

?No?no?? I whimpered again but with a confident smile, she brought it down and coaxed it between my lips and held it there, forcing me to submit once again. I felt the warm liquid trickling into my mouth and I sobbed with defeat. My tormentor knew how weak willed I?d become and her gorgeous smile was filled with victory for dominating me so fully.

?That?s it?? she coaxed me, ??That?s mommy?s baby?Drink your milk Chrissie, and then it?s naptime for my little panty princess.?

I sucked miserably, even though my stomach was completely full of the babyish drink. Meanwhile, Timmy was looking back at me with half closed eyes, his mouth sucking greedily now at the massive breast pressed against his face. He was breathing hard through his nose and Crystal?s sexy hand was stroking the front of his diapers which had the obvious effect of making the sissy giddy with excitement. His face and chest were bright red and although I knew he was tremendously embarrassed by the whole situation, I also knew he was deeply turned on by it all too. Crystal?s deep cleavage was only an inch in front of his nose and I knew he had a perfect view of her other bountiful melon, held delicately by the half cup of her bra. I heard him mewling with unbridled passion and Crystal was saying sweet things as he sucked her big br.east for all he was worth. Suddenly, he moaned out loud and his head rolled back as he came forcefully in his diapers. Gasping for breath, Timmy gazed back at me placidly, overcome by the intensity of his climax. Crystal smiled and brought his head between her two huge mammaries, allowing him to snuggle in her deep cleavage while he slowly recovered.

And that was when something inside me snapped. My tiny little wiener was sore and painful from trying to become hard within my own diapers and with all the sexual stimulation I was being forced to endure, I just couldn?t take it any more. I jumped off of Ms. Johnson?s lap and grabbed Timmy by the shoulder, jerking him away from Crystal?s comforting bosom. With a sudden impulse of anger I didn?t realize I had within me, I slapped Timmy on his groggy face, as punishment for an orgasm that had been denied me.

He immediately burst into tears and began crying like a baby, holding his cheek in his hands while the two women looked at me in utter shock. Ms. Johnson however, quickly recovered, and she jerked me around with a jolting grip of my wrist.

?You?ve just earned yourself a nice, hard spanking,? she said tersely, and she stood up abruptly, towering over me fearfully with her high heels.

?It?s not fair!? I cried vehemently in frustration, ?it?s not fair!!?

Reaching down, she swatted me harshly on my diapered bottom, landing her hard hand with a loud thud and causing me to buck forward.

?That?s right Chrissie. And now everyone?s going to watch you cry like a baby when I put you over my knee and paddle that sissy bottom of yours.?

She jerked me along as she strode down the hall and into the nursery, the other two not far behind us. Ms. Johnson has very long legs, and I struggled to keep up with her as she pulled me along behind her. Looking down, I saw how shapely her calves were and the confidence with which she walked in her five inch sandals. I began crying softly, knowing the terrible punishment that was awaiting me, just moments away.

As we entered into the warmly lit room, Ms. Johnson reached over and picked up the wooden paddle before sitting down in the straight backed chair next to us. Hitching up her skirt, she pulled me over to her, ordering me to hold up my dress so she could reach underneath and pull my plastic panties down. By now, Timmy was in the room and he was watching me with grim satisfaction, still rubbing his sore cheek. With several sharp, angry tugs, Ms. Johnson yanked my pretty panties down my legs and around my ankles.

?Chrissie. Before I pull you over my lap for your spanking, I want you to apologize to Timmy for your behavior,? she told me, her eyes blazing with fury.

I was blubbering with fear as I looked from her strong, dominating features, to Timmy?s.

?I-I-I?m s-sorry, Timmy,? I sobbed pitifully.

?Timmy, if you?d like, you may slap Chrissie the way he slapped you,? Ms. Johnson told the effeminate boy.

Without hesitation, he stepped forward and slapped me as hard as he could, although that wasn?t very much given what a weak sissy he was.

?OOUCHH!? I cried nonetheless and I held my hand to my own stinging cheek.

?And now it?s time for you to pay the piper,? she said as she pulled me over her firm lap. I struggled weakly as I fell forward, squirming over her smooth, bare thighs while she reached for the pins holding my thick diapers in place.

?No?no?I don?t want a spanking,? I wailed as she drew back the soft cloth covering my rump.

?You should have thought about that before you started misbehaving,? Ms. Johnson snapped as she pulled my diapers back, pushing them between my flailing legs.

I squirmed in terror as I looked up to see Crystal, her thin arms crossed over her massive bosom with a look that said I was getting exactly what I deserved.

The first slap of the paddle landed squarely across both cheeks, right in the middle of my still pink buns and I howled with pain, kicking wildly.


Ms. Johnson swatted each cheek individually with great force, using her strong, toned arms to deliver a harsh, resounding impact. I wailed helplessly, the tears streaming down my face as she kept up a steady, punishing rhythm, slapping each round, tender cheek, once, twice, then both at the same time. The sting was incredible and I slapped the floor in anguish, wishing I could somehow alleviate the pain.


She wielded the hard oak paddle mercilessly, bringing it down again and again on my soft, pliable bottom. It jiggled and yielded miserably to each punishing slap as I bawled my eyes out, kicking and thrashing each time the paddle blistered my youthful fanny. Finally, I surrendered and lay there in abject defeat, passively taking my spanking while Ms. Johnson turned my scalding bottom into two cherry-red globes of fire.


I could barely make out Crystal through the tears filling my eyes but she looked immensely pleased, seeing a babyish sissy like me crying and getting a good, hard paddling.

Finally, the painful ordeal at last ended. I lay over her lap, my breath coming in ragged sobs, as she slowly brought my diapers back up and pinned them back into place. I was too ashamed to look at anyone as she helped me to my unsteady feet while I bawled like a baby in front of everyone.

Ms. Johnson looked over at me severely, the paddle still clutched tightly in her hand.

?Have you learned your lesson, Chrissie?? she challenged me.

I couldn?t speak coherently but I blubbered an acknowledgement and nodded my head, tears streaming down my face in profusion.

?Good. Because I won?t have any fighting in my house?is that understood??

I was afraid to look into her stern eyes but I nodded my head again, trying to answer her through my crying.

?You?re a little sissy who wets his diapers like a little baby,? she scolded me severely, “And I?ll decide when, and if, you ever deserve to have an orgasm?is that understood??

I sobbed again in agreement as she began roughly tugging my plastic panties back up my legs.

?You?re going to be in diapers for a very long time, so you might as well get used to being treated like a baby.?

I cried openly, feeling full of self pity and I think even Timmy felt sorry for me because he came over and hugged me, kissing me tenderly on the cheek.

?Its okay, Chrissie,? he whispered to me.

I threw my arms around him and hugged him, crying hard on his shoulder as the stinging in my diapers continued to make itself painfully felt.

Crystal smiled and came over to put her arms around both of us.

?That?s much better. Now why don?t you two sissies kiss and make up.?

Wiping the tears from my face, I leaned forward and kissed Timmy softly on his warm mouth, even as I sobbed in defeat.

?Alright babies,? Ms. Johnson said as she stood up, ?let?s get you two into your cribs–you?ve had quite a day already.?

Tearfully, I stood there while Ms. Johnson unbuttoned my dress and removed it, hanging it up in the closet while she brought out a pink and peach colored onesie, decorated with Birdseye lace. She put the soft garment over my head and brought it down over my outstretched arms, lowering it over my torso and down to my waist. I winced as she pulled the front and back of it tightly across the fat thickness of my diapers, since it rubbed my blazing bottom closely, and snapping the row of three snaps between my inner thighs. The onesie had an elastic waistband that hugged my middle section and gave me a distinct bell shape as it hugged my embarrassing diapers. Looking down at the big bulge around my hips, I could see the Birdseye lace that surrounded my legs and waist, giving me a very babyish look.

Ms. Johnson removed my mary janes and lowered the rails on my crib, guiding me onto the vinyl covered mattress with soft words of encouragement. She tucked me in and then pulled up the soft pink baby blankets around my chin, after she handed me my teddy bear.

Looking across to Timmy, I saw that busty Crystal was doing the same to him and Ms. Johnson finished by pushing a big pink rubber pacifier between my lips.

?Nightey-nite, babies,? she said as she turned out the light but left the door open.

I sucked desperately on my pacifier as I shifted onto my stomach, still crying softly to myself. My bottom felt like a five alarm fire and I knew for sure that I?d never act up in Ms. Johnson?s house again.

…Three months later…

I sat at my vanity, carefully applying my make-up as I waited for Ms. Johnson?s summons. Today was the day when my mom was coming back from Europe and she would be finally taking me back home. Ms. Johnson wanted me to look very proper for her arrival and I was very careful in the way I did myself up. After a light layer of foundation, I had put on a soft blush and just a hint of pink eye shadow. Lastly, I put several glossy coats of bubble gum pink lipstick across my full lips which added considerably to the illusion that I was a girl.

Smacking my lips together, I sat back and looked at myself in the mirror, evaluating my efforts.

My longish hair was tied up in two sassy pigtails, the base of each being secured with a big pink floppy bow of its own. Ms. Johnson had picked out an Alice in Wonderland dress for me to wear and the short puffy sleeves accented my skinny arms, while the short ruffled hem would keep me busy ensuring it didn?t creep up in back to expose my pretty rumba panties. After changing my diapers in the morning, Ms. Johnson had dressed me in some glittery white tights and Mary Janes, after which she made me step into a lacey pair of pink rumba panties, silky and delicate, yet large enough to stretch over the fat bulkiness of my diapers. The three rows of bouncy ruffles across the seat added to the babyish feeling that was never far away anymore.

Just then, Ms. Johnson appeared in the doorway, looking beautiful, yet stern and imperious at the same time.

?Your mother has arrived, Chrissie. Stand up and let me take a look at you,? she ordered me.

?Yes Ma?am,? I replied submissively, as I stood up and held the edges of my dress delicately.

?Turn around, Sissy,? she told me, and I bashfully rotated to show her all sides of me.

?Have you wet yourself?? she asked bluntly, without offering any compliments on how I had prepared myself.

?No Ma?am,? I said quietly.

?Come along then,? she said as she reached down to take my hand.

She pulled me along down the hallway, her high heels announcing our presence as we made our way out to the living room. With her superior height, and quick, confident gait, I felt like a little girl being led out to be shown off to her mommy. As soon as we turned the corner, I spied my mom standing in the middle of the room, with an attractive, well endowed woman beside her. Despite my best efforts, I found myself blushing hotly as I bent down to give them my best curtsy.

?Hi Mommy,? I said respectfully, keeping my eyes respectfully downcast and demure.

My mom smiled at me and came forward, holding me closely and hugging me warmly.

?Well!? she exclaimed, ?You certainly have changed?and much for the better!?

?Thank you, Mommy,? I replied.

I felt her hand reach down and squeeze my thickly diapered bottom, confirming her suspicions about me.

?Chrissie, go fetch us some tea while your mother and I discuss things,? Ms. Johnson said dismissing me.

?Yes Ma?am,? I answered as I bowed to her and quietly left the room. I made a surreptitious sidelong glance at the other stranger in the room as I went to the kitchen to look at the pretty female that I hadn?t been introduced to yet. She looked to be in her late twenties, with a fantastic body and long, luxuriant, auburn hair. I found her to be stunning in every way and although I was extremely ashamed to be exposed to her in this way, I looked forward to finally meeting her.

While I was preparing the tea set for the three of them, I did my best to listen in on their conversation out in the living room. Ms. Johnson was telling my mom about my progress under her tutelage, making no attempt to leave out any humiliating details.

?When Chrissie first came here, he had a big problem with masturbation,? she was explaining, ?But I?ve got that all taken care of now. He wears a chastity restrainer underneath his diapers that prevents any sort of mischief from the little sissy. Of course, young boys being what they are, I knew it was necessary for the sake of his health that he should get some kind of relief from time to time. So I?ve taken the step of milking him once every week?that eliminates the nasty semen he?s built up while still depriving him of any kind of orgasm.?

?Frankly I?m amazed that you were able to achieve so much,? my mom said in obvious admiration, ?He was such a stubborn boy before I left.?

Ms. Johnson chuckled with amusement.

?Oh believe me?that kind of bluster doesn?t last long around here. You?ll find that he?s a changed boy?docile, obedient, polite, and respectful. I think you?ll be very pleased with the results.?

?I saw that he?s still wearing diapers,? my mom pointed out, ?does he still need them during the daytime too??

?Yes, unfortunately so,? Ms. Johnson sighed wearily, ?We made a try at potty training him but he just couldn?t manage to stay dry, even during the day. I?m afraid some little boys just can?t be without their diapers and plastic panties and Chrissie is one of them.?

?Well, I guess I really didn?t expect any different from him, he?s always been such a sissy,? my mom admitted.

?Yes, he certainly is,? Ms. Johnson agreed, ?I could tell that right off, from the first time you brought him in?he seemed like such a prissy, delicate, immature little boy, still wearing diapers like a little toddler. I?m afraid his prospects for landing a girl some day are remote, at best. What he needs is someone who can give him the discipline he so badly needs?a firm, maternal hand that?s not afraid to blister his bottom with the paddle when he misbehaves.?

As I stood in the kitchen, my face, ears and neck were blushing a bright red as the two of them discussed me in such belittling terms. It was as if they were talking about a three year-old, rather than a young man nearly sixteen. However, the tea was ready to serve and I didn?t dare dawdle?I knew all too well the consequences for making Ms. Johnson angry. Placing the cups and saucers on a tray, I minced back into the living room, the bulky thickness of my diapers preventing me from walking with any kind of grace.

?Have you had to use the paddle frequently?? my mom asked, ignoring me as she took one of the cups I silently offered her.

?No, not as much anymore,? Ms. Johnson said as she studied my service to them with a critical eye, ?He gets spanked once a week now, on Sundays, whether he?s been good or bad. We review his behavior for the past seven days and then I take him over my lap to correct his errors.?

?Does he always warrant a hard spanking?? my mom asked curiously.

?No, not usually. But I feel a good paddling helps clear the air and helps him to know his place. I also think a good cry is good for him, as it is for all sissies. He doesn?t like his spankings–believe me, but he?s a much better little boy for them?aren?t you Chrissie?? she said as she faced me.

?Yes Ma?am,? I immediately replied. I knew better than to contradict her, especially since I feared she might feel tempted to give my mom a demonstration of the power of her paddle.

?I?m sure you?re right,? my mom said in agreement, ?which is why I?ve hired Jordan here as Chrissie?s tutor and nanny.

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