Story: Chrissey’s Summer in Diapers – Part 3

By | February 22, 2016

After a short while, I found myself upstairs, moving down the hallway in the general direction of Ms. Johnson?s bedroom. I felt full of nervous, sexual tension and my little wiener constantly twitched within the encircling bonds of my chastity device. Up ahead, I could faintly hear the sounds of Ms. Johnson?s voice, filtering out through an open crack in her doorway. Inching forward as silently as possible in my mary janes, I snuck up to investigate the situation better.

As I peeked around the edge of the door, I saw Ms. Johnson sitting on her bed with Timmy laid across her lap. Once again, I was mesmerized by the erotic scene before me.

Ms. Johnson had unbuttoned her halter top and it hung loosely from her slim arms, leaving her fantastic chest nearly fully exposed. Her two massive breasts were supported by a white lacey bra that held her two curvy melons in an alluring double cleavage, due to the fact that they pushed up and against each other in the most exciting way imaginable.

I gasped in utter awe at her beautiful boobs and watched with burning jealousy as my rival Timmy, suckled from her right one like a baby. She was cradling his head in the crook of her arm while her other hand was reaching over and softly stroking the front of his fat diapers. Apparently, she had dressed him in some sort of thin, stretchy panties because they were tangled around his ankles, just above his pink Keds sneakers. His smooth, feminine looking legs gave him a particularly childish appearance and his shiny plastic covered diapers completed the scene.

Nonetheless, the humiliated sissy looked distinctly uncomfortable in his position. He was whimpering with embarrassment as he suckled from the gigantic nipple filling his mouth. Her big breast dwarfed his little head and he had his mouth full, sucking and nursing while he fidgeted nervously.
Ms. Johnson was gently encouraging him, as she had when she was administering our enemas.

??Sh-shhh?there you go?that?s a good little boy?drink all you can?that?s it?that?s a good baby??

I bit my lip and felt my penis growing stiff within its little prison and I stifled a gasp of pain as it fought madly to break free of its bonds. Unconsciously, I reached down to try and move it as one might do when your wiener is trapped by some part of your underwear. The only problem was, now my underwear was a big, thick pair of diapers, covered by plastic panties, and there was no amount of re-arranging that I could do to relieve the pressure on my throbbing wee-wee.

I cursed silently to myself but I couldn?t force myself to move away from the enrapturing scene taking place before me.

Ms. Johnson was alternating between stroking Timmy?s head, then the front of his thick diapers, helping to stimulate the emasculated sissy further. From time to time, she?d hold her big breast up to his mouth when he tried to back off, to make sure he couldn?t escape this most babyish of feedings. The poor sissy whimpered and mewled, squirming in her lap and desperate to escape his predicament but she was determined to make sure he got his full share.

?Come on Sissy, suckle from that nipple?I know it?s a lot but you?ll just have to try?there you go?that?s mommy?s baby?such a good little sissy.?

Timmy squirmed some more in her lap, trying weakly to rise up but Ms. Johnson held him in place.

?What?s the matter Timmy?? she asked innocently, ?Is mommy?s little baby going to wet his diapers? Is that the problem??

With his face mashed against her massive breast, Timmy was entirely unable to articulate any kind of response. All he could do was to fidget and whimper in weak protest.

?Ahh, I know,? she exclaimed suddenly, ?You?re finished with the right side and you want the other one??

Timmy shook his head no but she easily pushed his head between her breasts and then towards her left one. With deft movements, she tucked her big right boob back into its lacey cup and then pulled the other one out to position it before Timmy?s trembling mouth. He moaned babyishly but kept his eyes shut, apparently because he found the situation so utterly overwhelming to his senses. Ms. Johnson smiled down on him and forced her swollen nipple in between his lips, making him suckle from it as he had the other one.

?There you are?that?s my baby,? she said soothingly, ?You?re getting quite a feeding today, aren?t you??

I bit my lip hard and pushed against the cushiony surface of my crotch, desperate to relieve the strain being imposed on my balls and wiener. My little member was straining furiously in its prison and the pain was almost unbearable.

Suddenly, I heard footsteps down the hall and I tore myself away from my voyeuristic ambitions to run and hide.

Late that night, as I lay in my crib listening to the sound of Timmy sleeping, my mind was consumed with trying to find a way to defeat Ms. Johnson?s chastity device that she had secured me in. Every time I thought back to the scene in her bedroom where she was pushing her beautiful, massive breasts into Timmy?s squirming face, my heartbeat doubled and my little penis fought against its bonds determinedly. It was just so frustrating! I wanted to kiss her sexy boobs in the worst way but even more than that, I wanted to be able to stroke my little member without restriction.

Whereas before, the soft cushiony cloth of my diapers had served to assist my masturbatory misadventures, now, they mocked me with their caressing, tempting embrace. And pretty Ms. Johnson only added to my frustration with her clinging blouses and tops that showcased her fabulous bosom. She was so beautiful, but yet so strict!

With absolutely no way to relieve myself, all I could think about was sex. Would she ever release me from my bonds? Would I ever get to cum in my diapers again? I could think of little else as I drifted off to a troubled sleep.

The next day, after having our diapers changed and fed breakfast, Timmy and I were left in the nursery to amuse ourselves. With little else to do, we soon found ourselves playing with Barbies and after a while, I totally forgot that I was dressed in diapers and a short dress, and I gradually started acting more like a little girl of six, rather than the fifteen year old guy that I actually was. Timmy too, was soon giggling like a sissy and we seemed to lose all our inhibitions with each other.

As a young sophomore back in school, I was used to maintaining a certain false masculinity to keep the bullies from constantly picking on me. But here, I felt like I could just be myself and relax, letting my true self come out. Timmy certainly wasn?t judgmental and if anything, he seemed to be the epitome of a sissy, with his childish giggling and feminine mannerisms.

We were playing and laughing, having forgotten the outside world, when all of a sudden, a pair of gorgeous young women walked through the door unexpectantly. I dropped my Barbie in stunned silence as I gaped up at the two hot babes dressed in skimpy cheerleader?s outfits. One was a brunette and the other was blonde but both were dressed identically in pink shimmery, form-fitting halters and bouncy short skirts. The latter barely managed to cover their panties and I imagined that if they were to turn around and bend over, their perky bottoms and panties would be revealed to us in all their glory. Their halter tops were very low cut and the scoop style in front showed off their wonderful round brea$t$ to my roaming eyes. These girls were both very pretty and the brunette had her long, silky hair pulled back showing her high, model-like cheekbones while the blonde had curls and curls spilling over her soft, bare shoulders. They looked down at us with a mixture of surprise and amusement but I felt I sensed a trace of cruelty in the brunette?s eyes.

?I found them, Julie,? she called out over her shoulder in the direction down the hall, ?they were in their nursery, playing with dolls.?

I blushed three shades of red as I looked up at the statuesque girls in their sexy high heels, staring down at us and laughing at our appearances. Here I was, dressed in a very short party dress and diapers, caught in the act of playing with Barbie dolls when any other guy my age would have been out raising hell and getting into trouble. In my extremely agitated state, I suddenly felt the front of my diapers growing wet and warm, as I uncontrollably wet myself. Instinctively, I squealed with panic and my hands went down to as if I could staunch the flow by pressing against my crotch. This only served to bring everyone?s attention to me and they laughed all over again as they realized I was wetting my diapers like an incontinent toddler.

Just then, Ms. Johnson strode into the room and taking in my infantile display, she frowned and shook her head.

?I see you?ve met my two sissies,? she said disdainfully as she crossed her arms over her very impressive chest.

?Yes,? the brunette giggled uncontrollably, ?And I think he just peed his diapers.?

Ms. Johnson regarded me sternly and she reached down to put her hand against the warm surface of my plastic panties. As she did so, I stared down the cavernous gap of her cleavage, seeing the delicate lace cups of her bra hidden beneath her blouse. With her bending down so close to me, I inhaled deeply from the subtle feminine scent of her skin and I felt her undeniable superiority overwhelm my senses. Feeling the wetness in front through my vinyl panties, she reached around and felt my bottom while I squirmed in uncomfortable silence, my face glowing a bright red.

?Well, his diapers can still take some more if you?d like to wait to change him,? Ms. Johnson pronounced authoritatively, ?Chrissie is used to wearing wet diapers so he can go around like that for a while and it?ll be fine.?

My humiliation knew no bounds as she discussed me in the same terms and tone of a helpless two year-old.

?He often wets himself like a baby whenever he?s startled,? she explained to the pretty cheerleaders who were shaking their heads in amazement, ?but I keep him in very thick diapers which can really hold a lot. Just keep an eye on him and check him from time to time and when his seat becomes saturated, that?s usually when I change him.

?I?m going to meet Crystal for lunch,? she continued as she checked her watch, ?but I?ll be back in time to tuck the sissies in for their afternoon nap.?

I bit my lip nervously and kept my eyes downcast but I couldn?t stop blushing from the circumstances. I was so ashamed to be spoken of like an infant, especially since I was sitting in front of these hotties in my now very wet diapers, looking and acting like a helpless baby girl.

?You go ahead and take off Julie,? the brunette assured her, ?Barbie and I can take care of these two sissies.?

?Oh, I almost forgot,? Ms. Johnson said as an afterthought, ?their paddle is hanging up there on the wall. Make sure to use it if they give you any trouble?any at all.?

The two girls smirked at each other and suppressed their giggles.

?Oh believe me?we will!? Barbie exclaimed.

?I like to paddle their bottoms until I see real tears?and then I really lay into them,? Ms. Johnson added with determination.

The girls were nodding their heads in complete agreement.

?Don?t you worry, I?ll make sure they cry if they even think of misbehaving,? the brunette replied.

I shrank in fear as I contemplated the steely will of these pretty vixens that held total power over us in Ms. Johnson?s absence.

?Good. Thank you Alyssa,? Ms. Johnson said as she walked out, ?I?ll see you two later.?

The cheerleaders said their goodbyes and then turned their attention back to us.

?I just can?t believe it,? Alyssa said, her tone of voice suddenly becoming very disparaging, ?I remember when you were still going to our school?I knew you were a wuss then but I had no idea!?

I felt my face and neck growing hot from my blushing and I could hardly look her in the eye. Casting my eyes down at the shiny surface of my pink plastic panties, bulging out from the thickness of my cloth diapers, I realized just how infantile I looked. It was absolutely mortifying to be seen in this situation by my former schoolmate.

?I should put you over my knee right now,? she said menacingly, ?but I have a better idea.?

With that, both she and Barbie pulled a pair of big rubber dildos out of their purses and my heart skipped a beat as I saw that they were mounted on a harness of some sort.

?If you two don?t do exactly as we say?we?re going to bend you over and fuck you in the ass with our strap-ons,? she threatened us as she waved the monster sized dildos at us.

Timmy was quivering like a leaf and I saw his lip trembling with fright as Barbie looked down on him with an intimidating glare. I could hear the faint hiss of pee as he began helplessly wetting himself, breathing in short gasps as he looked around, hoping desperately for some kind of escape.

?I think we?ll have you two little fairies pose for us,? Alyssa announced, ?I brought my digital camera and I want to take lots of pictures of you two to show everyone what sissies you are.

?But first, why don?t you paint your sissy boyfriend?s nails, Chrissie,? she ordered me as she walked over to the vanity and snatched up a bottle of bubble gum pink nail polish.

Both Timmy and I were too terrified of the girls, to try standing up to them. I took one look at the fat, ten inch strap-on dildo she had in her hand and I quailed at the thought of refusing her. With perhaps a little more eagerness than I would have preferred, I took the nail polish from her and sat next to Timmy who looked like he was about ready to cry. Barbie got into it as well, dividing the effeminate sissy?s fingers with wads of Kleenex while I applied several coats of glossy pink lacquer to his nails. He sniffled and whimpered but sat there submissively while I added coat after coat to each of his fingertips.

I knew Timmy had little more control of his bladder than I, and sure enough, while he was getting his nails done, I heard him wet himself once again. He began shifting in his seat as the soggy cloth began to surround his crotch and buns and he fidgeted as the minutes ticked by, while his diapers became more and more soaked. Finally, he couldn?t stand it anymore, the warm, wet cloth clinging to his sensitive little bottom.

?Barbie–? he started to whine.

??That?s Miss Barbie, to you, Sissykins,? she snapped.

?Miss Barbie,? he began again meekly, ?Do you think I could please get um, changed?I kinda um?wet myself,? he said lamely, still keeping his eyes downcast on the floor.

?Too bad, Panty-waist,? she retorted, ?you?ll just have to get used to it.?

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