Story: Chrissey’s Summer in Diapers – Part 4

By | February 22, 2016

Timmy obviously didn?t like that response and he sniffled in silence, fighting back the tears that threatened to overwhelm the chastised sissy.

Finally, I finished his nails and a part of me took a measure of pride in how well they came out. Timmy looked even prissier than he did before, if that was even possible, and he looked down on his feminized hands with a sob of resignation.

?Now it?s your turn,? Alyssa said as she pushed me roughly.

My pride and subtle sense of superiority evaporated as Timmy gleefully took the nail polish from me and began doing my nails. I could only imagine what these two knockouts must think of us, submitting submissively to their orders like docile sheep when any other guy would never have stood for it.

As I sat down while Timmy painted my nails, I saw Barbie snapping pictures of me, taking humiliating shots that made me look totally sissyish and compliant. After my nails had partially dried, the two girls made us apply glossy lipstick to each other and then pose in the most humiliating ways, holding hands, kissing each other?s cheeks and leaving pink lipstick impressions all over each other, then hugging like pansy lovers, all while the digital shutter clicked away repeatedly to capture our shame on film.

?I was just going to show this to our friends but now I?ve decided that I?m going to post these all over the internet so everyone can see what a pansy-ass sissy you?ve become, Chrissie,? Alyssa promised me.

?Please don?t!? I begged her pathetically but she just crossed her lithe arms over her perky breasts and smirked back at me, nodded in confirmation of my fears and daring me with her eyes to oppose her.

?Okay. Now for the crowning shot,? she said wickedly, ?I want you two sissies to kiss each other, right on the lips.?

Barbie giggled at the cleverness of her friend?s wicked plans, slapping Timmy on his diapered bottom for good measure.

?Go ahead, Panty-waist,? she sneered, ?Kiss your little boyfriend.?

?Please, please don?t make us!? we begged her again but she picked up her strap-on in her small hands and thrust it in our faces.

?Do I need to use this on you?? she said threateningly.

We shook our heads violently in fear and then looked at each other with apprehension.

?Then plant your pink lips all over your boyfriend?s there,? she said as she rudely pushed me again, ?do it now or I?ll make you French kiss him too.?

I gasped in shock at her suggestion and choked back a sob as I turned to see Timmy wiping a tear from his face. Holding him in my arms, I drew him closer but at first, he was afraid to face me. He looked fearfully at our two sexy tormentors and then back to me, realizing we had no choice but to do their bidding. As Barbie kept snapping the shutter on the camera, I pulled Timmy slowly towards me and kissed him tenderly on his lipstick covered lips. He gasped and blushed as no doubt I was as well but Alyssa wasn?t satisfied.

?Make it a longer kiss?reach around and squeeze his butt while you do it. I?m going to time you and if you stop kissing before I tell you to, I?m going to hump your little ass with the strap-on ?til you can?t walk straight.?

I gulped hard and threw my arms around Timmy, kissing him hard as my hands went down to fondle the thick, pliable seat of his plastic baby panties. Even though I had never kissed a guy before, nor had I ever wanted to, I felt a strange mixture of emotions swirling around inside of me. Timmy?s lips felt soft and warm against my own and his bottom felt cushiony and erotic. I could feel the wetness that had seeped up into his seat and I pulled his panties up by the waistband, so that his diapers wouldn?t sag so much. A tear trickled down Timmy?s cheek but I kept kissing him passionately, afraid to let go. At the same time, my own little wiener was fighting against its bonds within my diaper as it struggled to become hard. For some reason, I was getting tremendously turned on by forcibly kissing Timmy and I couldn?t have been more surprised.

Meanwhile, Barbie was getting countless shots of our lusty embrace, my hands squeezing Timmy?s thickly padded rump while he did the same with mine. Oddly enough, I began to feel Timmy?s tiny little penis beginning to grow within his diapers and as I opened my eyes, I could see that his were half closed, surrendering to my advances. His lips began to part, as if he wanted my tongue and without thinking, I accommodated him. His mouth was hot and he moaned like a girl as I tentatively explored with my tongue, shocking myself with my own lack of inhibition.

At last, Alyssa gave us the signal and we were allowed to stop. Standing there breathlessly, we both blushed profusely at each other, deeply ashamed at having committed the ultimate act of sissihood. What have I done, I demanded of myself. I had just French-kissed the biggest sissy I had ever met and now everyone who had ever known me would see the pictures of it!

I saw the two girls wink at each other and they stepped aside, taking their miniskirts down in unison. I stared openly at their smooth, sexy legs and upper thighs that were now completely revealed to us and for a fleeting moment, I thought we were about to be rewarded for cooperating with their cruel demands.

But my hopes were quickly dashed as I saw them stepping into the strap-on harnesses, a look of evil glee on their pretty faces.

?Bu-bu-but I thought?I thought you said if we did what you wanted?that-that you wouldn?t use those on us,? I stammered nervously.

?I lied,? Alyssa said simply, as she snugged down the wide straps that held the monstrous dildo in place. I gulped with fear as I looked down at the intimidating device, jutting out menacingly from each of the slim, fit, cheerleader?s pelvises. My anus twitched nervously as I contemplated what was about to happen. Judging by the look on Timmy?s horrified face, I don?t think he even knew what a strap-on was but I could tell he didn?t like it. My mind raced as I tried to think of a way to escape our horrible fates but I couldn?t imagine any way out of it. Unlike myself, these girls were in excellent physical shape and neither one of us was any kind of match for them.

Alyssa was facing away from me as she cinched her strap-on up snug against her crotch. I gazed in admiration at the sheer panties she was wearing that stretched across her firm, shapely buns but when she turned around, I was greeted by the incongruous sight of a huge rubber cock jutting out from in front.

?We?re going to help out you two sissies by preparing you for your future boyfriends,? she said as she pushed me down onto my knees into a kneeling position, ?And the first thing you need to learn, is how to properly suck a cock.?

Staring at the massive head of her dildo, inches in front of my face, I gulped hard and shook my head frantically, hoping to dissuade her from her humiliating plans. Reaching forward, she placed her hand on my head, to guide it towards her dildo and I was afraid to struggle against her.

?Oh yes Chrissie, this is just the first of many cocks you?ll be sucking. Better get used to it because no woman is ever gonna have anything to do with you.?

Her biting words stung me, making me want to cry and I looked up at her with a sad, pleading expression. By contrast, she looked down at me with an evil smile of smug confidence and power, a woman fully in control and used to having her way.

She pulled my head closer until my pink lipstick covered lips were pressing against the big, bulbous head of her dildo. Refusing to submit any further to this degradation, I kept my lips tightly closed to deny her the satisfaction.

?You want to suck a nice big cock, don?t you Chrissie,? she taunted me cruelly.

?No?? I responded, but the second I opened my mouth she shoved the dildo past my pink lips, cramming it all the way in until it bottomed out against the back of my throat. I squealed in shock, gagging desperately but both girls laughed at my plight with great amusement.

?That trick works every time,? Alyssa chuckled as she began slowly pumping the dildo in and out.

Kneeling before her, I was forced to su-k on the fat rubber cock as she held my head in place and moved back and forth with her sexy hips. I heard another squeal of surprise and out of the corner of my eye, I could see Timmy getting a similar treatment.

?That?s right, suck the big cock Chrissie,? Alyssa said from above me, ?This should come very natural to you.?

I blushed deeply as she kept up a steady stream of humiliating comments about my performance.

?Use your tongue Sissy?that?s right, suck it like it was you wittw ba-ba?your future boyfriend will really appreciate all the practice you?ve made?.there you go?that?s it, take it all the way in?wrap those pink lips around my cock?that?s it??

I could see a pink ring around the base of her dildo representing the farthest extent that I had been able to take it in. Her dildo filled my mouth completely, stretching my cheeks wide as it plunged in and out.

?If only your little friends could see you now,? she said as she placed one hand on her curvy hip and left the other one on the back of my head to guide my rhythm, ?but then?they will see you?just as soon as I make prints of these photos.?

Looking up, I saw Barbie snapping a shot of me with my mouth full of fat rubber cock and my faced blushed bright red again.

?Smile for the camera, Chrissie,? Alyssa laughed, ?but then, it must be a little hard when you?ve got a big cock stuffed in your mouth.?

The girls laughed again and I wondered when they would ever stop tormenting us.

?You see?this is what you?ll be doing to get your boyfriend all nice and hard. That way he can bend you over and ram it in your ass so you can cum like the big sissy you are,? she said caustically.

My jaws were getting sore from having been stretched for so long and at last, Alyssa pulled it out of my mouth.

?Okay, that?s enough fun for you Chrissie,? she remarked as she picked up the jar of vaseline from the top of the dresser.

Barbie had brought two straight backed chairs into the nursery and they bent us down over them, pushing our heads through an opening in the backs that I could just barely squeeze my shoulders through. This left me on my hands and knees, my stomach supported by the seat and my bottom exposed while my torso was trapped through the back of the chair. They had cleverly arranged the chairs so that both of us would be forced to look at each other?s face, now only inches apart. I thought I would try and be tough about the situation but when I saw Alyssa take the oak paddle off the wall, I began crying crocodile tears of fear. Barbie was pulling our plastic panties down and unpinning our wet diapers, exposing our damp bottoms to these merciless vixens while we both whimpered in terror.

Alyssa had positioned herself behind me and because of my restricted position, I couldn?t see her. Nonetheless, I could feel Barbie tugging my wet diapers down, leaving my bottom both helpless and defenseless to their cruel intentions. No sooner had my damp buns felt the chill of the air when I felt the searing impact of the paddle across my tender cheeks. I howled out loudly and tried to move but the chair held me in my awkward position, preventing me from getting up.


I wailed out in pain and grabbed the chair legs as Alyssa delivered several stinging wallops to my soft, round bottom, quickly bringing me to real tears. I sobbed and cried helplessly as she delivered a series of harsh, angry swats with that dreaded instrument of discipline, aiming careful and applying as much force to each slap of the paddle as she could. Those holes in the paddle really added to the sting and that, combined with the dampness of my bottom, made each swat feel like I was being spanked with a red hot frying pan.

As I lay there sobbing, she handed the paddle to Barbie who took up a similar position behind Timmy. The poor sissy didn?t even wait for her to start spanking him, he burst into tears immediately and began crying like a baby.

?Keep that pretty little bottom right where it is,? she said wickedly as she raised the paddle up and behind her, ??cause I?m about to give you something that?s really gonna make you cry.?

Through the tears in my eyes, I saw her bring down the paddle in a blistering swat at poor Timmy?s defenseless bottom. His eyes widened like saucers and he howled out at the top of his lungs. I watched with perverse fascination as my sissy companion had his fanny paddled without pause or mercy. He beat his little fists on the floor and kicked his legs as the paddle slapped his helpless cheeks in blistering, angry succession. His youthful buns jiggled miserably with each punishing swat and I looked into his face to see the tears streaming down his distraught face.

Before long however, Barbie finished and she set the paddle down with casual disregard, taking the time to coat her dildo with a thick, sticky layer of vaseline. As I contemplated what was about to happen to him, I felt Alyssa?s own strap-on, pushing firmly against my back hole, probing for entry. I moaned weakly but the fight had already been spanked out of me. Submissively, I lay there while she pried my stinging cheeks apart with her long, manicured fingers, attempting to gain entry to my virgin back hole. I looked to Timmy for support and saw that he was whimpering with fear, crying softly while Barbie slowly and tauntingly rubbed the thick head of her dildo up and down the crack of his red, hot and stinging bottom. His moans were coming in shorts squeals now, more out of fear than any real pain. Barbie had an evil gleam on her face as she positioned the fat dildo against Timmy?s hole, making him squirm with terrified apprehension. Pushing firmly, she forced the rubber phallus past his pouting sphincter and deep into his anus, making him savor the fullness of a giant cock.

Timmy squealed loudly, his face a picture of shock and distress while Barbie drove the big dildo deep inside him, holding it in place to make him feel every humiliating inch of it. She smiled with smug satisfaction as Timmy squirmed helplessly, his body trapped within the chair. Just then, I felt Alyssa?s own strap-on push past my rim and it slid deep inside me, making me cry out with a loud squeal. I felt like I was being split in two as she pushed it farther and farther, forcing me to spread my legs in abject submission.

I had never felt so emasculated in my life as these two sexy babes began to slowly and methodically hump us. At my young and tender age, I hadn?t given too much thought as to what it would feel like to have a big, thick cock pumping me in and out but I was surprised by the sensation. It had initially hurt quite a bit as I struggled to accommodate the massive invader in my little hole but as she slowly slid it in and out, I felt another sensation starting to take hold?that of sexual pleasure.

Looking back up at Barbie, I saw her reach down and switch something on, followed by a low buzz. Alyssa must?ve had the same thing because I could feel a slight vibration around the dildo sliding inside me. It appeared that the vibrating device was connected to a part of her strap-on that was intended to provide stimulation to the female wearer and I could see the effect of this when I looked up to see Barbie, her eyes half closed as she savored the waves of passion flowing through her curvy, sensual body. She looked utterly ravishing, her long blonde curls swaying back and forth as she drove the strap-on deep into poor Timmy?s bottom while he squealed like a schoolgirl. Her round br.easts, which were the size of two ripe cantaloupes, jiggled in her snug, form-fitting top with each thrust she made into my helpless, hapless companion. From time to time, she?d bite her lip as she held the dildo as far in as it would go, which also had the effect of pressing the vibrator hard up against her sex. Both she and Alyssa were now moaning with pleasure as they ground their dildos into our sissy holes. I looked at Timmy?s face which was still covered with my lipstick kisses and even he was starting to get tremendously turned on. He was moaning freely with each thrust of Barbie?s strap-on, and breathing deeply from the pounding he was getting.

Both girls picked up their pace and the dildos slid in and out, faster and faster, as they gripped us tightly by our hips. Timmy?s moans were coming closer and closer together and all of a sudden, I heard him cry out as he came uncontrollably in his wet diapers. I too, would have liked to cum, but my chastity restrainer prevented my efforts to get hard. Despite the intense stimulation my hole was receiving, by tiny little wiener was still held with implacable bonds that refused to allow me to enjoy any sort of sexual activity. I could only cry tears of frustration as Alyssa pounded my back passage thoroughly, digging her long nails into the soft skin of my hips as she sought to get the best grip she could. I wailed and squealed while Alyssa enjoyed every tantalizing vibration of her device, sending her to the brink of orgasm.

At last, both girls seemed to peak at the same time and with one last hard push, they jammed their dildos in as far as they could go. My hole was stretched to the limit and I could feel the fat rubber head pushing furiously against me. Alyssa used all her body weight (all 120 pounds of it) to keep the dildo crammed up inside me, while I moaned like a helpless little girl. With a room deafening cry, both the girls came with great exuberance, spending themselves as wave after wave of orgasm roiled through their slim, youthful bodies. I watched with fascination, Barbie?s face reddening as she gasped from the strength of her climax. Her curly hair was spilled over her pretty features in a picture of wild dishevelment as she ground her dildo against Timmy?s backside. He whimpered and squirmed, trying to get away from the monster cock buried inside him but there was nowhere for him to go. I too, struggled to escape my tormentor?s determined assault, but I could do nothing to alleviate my suffering. My poor back passage was tired and sore from the intense reaming it had taken and I waited impatiently for Alyssa to free me.

When the girls had finally spent themselves, they reached down and clicked the vibrators off, slowly easing the fat dildos out of our bottoms. I breathed a deep sigh of relief and when I looked into Timmy?s eyes, I saw that he was smiling sheepishly back at me.

?There,? Alyssa said breathlessly, as she began undoing the straps to her strap-on, ?Let that be a lesson to you sissies. Now you know your place in this world. Only next time, I?ll have my boyfriend come over and cum in your mouth. I?ll bet you?d like that, wouldn?t you Chrissie.?

She emphasized her question with a harsh slap to my still red bottom.

?OWWCHH!!? I cried out, still immobilized by my position within the chair.

After cleaning up their dildos, the girls re-pinned our wet diapers and pulled our plastic panties back into place, leaving us to endure the cool, clammy embrace of the wet cloth. Frankly, at this point, I was afraid to ask them to change us and I shuddered to think what else they might have in mind for us. After putting their strap-ons back into their purses, the girls stepped back into their miniskirts and zipped them up, an act that was extremely arousing all in itself.

Just then, Ms. Johnson came back home and it appeared we would saved from further torment at the hands of these totally hot, yet cruel cheerleaders.

?Hi girls, how did it go with the sissies?? she asked as she set her car keys down. I saw that another woman had come in behind her and much to my relief, she smiled warmly at us.

?Well, after they started playing with their make-up, they kinda got carried away with each other,? Alyssa remarked with a smirk directed at Barbie.

Ms. Johnson came up and stood over me, her pretty features creasing as she looked down at the lipstick kisses all over mine and Timmy?s face.

?What on earth have you two been up to?? she said with exasperation.

My mouth dropped open and I wanted to relate the entire humiliating hour that had just transpired but a stern look of warning from Alyssa who was standing behind Ms. Johnson told me that there would be hell to pay if I did. For a moment, I struggled to find the words as I looked around, first at Timmy, who was now biting his lip guiltily, and then at Alyssa who was regarding me coldly.

?Um?I guess um, we were just?you know, kinda havin? fun, Ms. Johnson,? I mumbled meekly.

She shook her head in obvious disapproval but said no more of it, apparently thinking that it was only natural that two sissies left alone would sooner or later begin kissing each other.

Reaching down, she squeezed the seat of my diapers and felt the soggy cloth within my vinyl panties, confirming her suspicions of my condition.

?Looks like these two sissies are due for a diaper change,? she told her friend that had come in with her, ?Would you like to help me, Crystal??

?Sure,? Crystal replied brightly, ?I?ll take this little cutie here.?

I blushed as she began tugging my clinging plastic panties down without any prompting, as if she were my own mother. Nonetheless, I couldn?t help but notice that she was totally sexy with a thin, clinging sweater she was wearing that hugged her immense br.easts closely. She appeared to be in her late twenties, tall, and she had her dark hair swept back in a sassy pony tail. Her manner was warm, yet firm, and I could tell she was quite used to dealing with helpless babies who wet themselves. She treated me as if I were just another one that couldn?t do anything for himself and she made me hold the hem of my party dress up while she worked my panties off my diapers and down my legs. After putting my soiled baby pants in the diaper pail, she sat me down on the changing table and proceeded to unpin my soaking wet diapers.

?My, my?? she tsked me, ?This one?s quite a little wetter.?

My face reddened and I bit my lip with embarrassment.

?Yes, he has no more control of his functions than any baby,? Ms. Johnson told her as she stood towering over me, ?Personally, I?m doubtful that he can even be potty-trained.?

Crystal shook her head but she smiled down at me nonetheless.

?That?s okay Chrissie,? she said as if she were addressing a two year-old, ?We?ll get you all fixed up in some nice thick diapers before your nap.?

My face reddened some more and as I glanced over, I saw Timmy smiling down at me and I suspected some part of him enjoyed seeing me humiliated.

Crystal pulled the wet diapers out from under me and she noticed the distinctive, red oval marks that had been left by the paddle.

?Well, it looks like someone?s been a very naughty boy,? she said, half smiling at me, ?Did you get a wittw spanky-wanky??

I couldn?t stop blushing from her babyish treatment of me and I nodded in acknowledgement.

?Awww?does baby?s little bottom hurt, hm?? she asked with mock concern, ?Aunt Crystal?s gonna make it feel all better, just you wait.?

Grabbing a big handful of diaper rash cr?me, she smeared it across my entire backside, coating it liberally with the sticky stuff while her other hand gripped my ankles and held them up over my head. I held onto the sides of the changing table desperately, blushing furiously as this stranger ran her soft slippery hands across my punished buns, working the greasy emollient thoroughly into my skin.

Barbie and Alyssa watched us in silence, shaking their pretty heads at my babyish routine. After setting me back down, Crystal took a stack of three thick diapers and slid them under my rump, positioning them evenly on both sides.

?Here you are Sissykins, a nice big diaper for our big baby,? she said brightly. Taking the baby powder, she began shaking it all over my crotch and stomach, humming a nursery rhyme as she did.

I bit my lip with embarrassment as everyone stared down at me, a young man being pinned into his diapers like a helpless child.

After snicking them closed, she patted me on the thick front and said, ?Now just you wait, Chrissie, while I find you a nice pair of plastic panties for you to wear.?

I sat waiting in silence, my face and ears burning with shame while she sifted through the drawer looking at various baby pants, holding some up and commenting on them.

?Now these are cute,? she said admiringly, ?such soft ruffles around the leg and waist?they?re perfect for a sissy like you who?s still in diapers!?

I wilted under her humiliating treatment as she gathered the leg openings in her delicate hands and began pulling them up my legs.

?Hopefully, these will fit over your thick diapers, Chrissie,? she said as she slowly drew them upwards.

?They should be fine,? Ms. Johnson offered helpfully, ?those are all full-cut to accommodate thick, thirsty diapers like these sissies wear.?

Sure enough, as Crystal began snaking her long fingernails around the waistband, she worked the shiny pink plastic panties up and over the bulky circumference of my diapers, sealing them up fully and completely.

?There,? she said satisfied as she patted the smooth, vinyl covered front of my bulging diapers, ?you?re all set for your afternoon nap.?

The cheerleaders shook their heads once more and then said goodbye to Ms. Johnson and Crystal. While Timmy got his diapers changed, I sat in uncomfortable silence, still trying to come to terms with the intense humiliation I?d suffered today. I?d never felt like such an emasculated sissy in all my life.

At the same time, Ms. Johnson went and filled a jumbo sized baby bottle with milk and warmed it up, bringing it in right as Crystal was finishing up.

?Well Julie, here you are; two sissies, diapered, changed, and ready for beddie-bye,? Crystal said as she slapped my thickly padded bottom.

?And now it?s time for the babies to get their milk before their naps,? Ms. Johnson said with an evil gleam in her eye.

Taking our hands, the two sexy women led us out into Ms. Johnson?s spacious living room and sat us on the expansive couch next to them. I meekly submitted as Crystal sat down and pulled me up onto her lap, cradling my head against her big, soft breasts. I was filled with sexual excitement as my cheek touched the fuzzy, comforting material of her thin sweater that was wrapped tightly across her swollen bosom. I was positive that my moment had finally arrived?at last, I was going to get to nurse from a bare breast! I had hoped for Ms. Johnson, of course, but this woman was exciting in her own different way. Her big, round boobs had captured my attention from the moment she had walked in the room and now I was about to get the chance to suckle from them. My tiny little penis began to immediately harden, only to be painfully restrained by my chastity harness.

I was facing the other end of the couch where Ms. Johnson had positioned Timmy, evidently to give him the same treatment. I smiled across at him, even as he became apprehensive of another humiliating session at our guardian?s big breasts.

?I?m so glad you were able to help me out with my?you know, situation,? Crystal said to her.

?Oh, don?t mention it,? Ms. Johnson replied with a waving dismissal of her finely manicured hand, ?Its good experience for a sissy to nurse from the breast again.?

?Its just that with my baby being unable to take mother?s milk, I was forced to use a breast pump to get rid of all of it?it just seemed like such a waste.?

?Oh yes, I totally agree,? Ms. Johnson said as she began unbuttoning her straining blouse, ?And this little sissy needs all the milk he can get to be a big, strong boy.?

She said the latter part in her mocking voice which left no doubt about how she felt about Timmy.

?Looks to me like you?ve got quite a bit to feed him, just by yourself,? Crystal remarked as she admired the mammoth size of Ms. Johnson?s right breast, now visible that her blouse was fully open. I felt my temperature rising as I stared past the twin mountains of Crystal?s, at the soft, plump skin of Ms. Johnson?s mammary now revealed. I licked my lips in excited anticipation of what was about to happen.

The latter chuckled at Crystal?s observation.

?Yes, well, I?m sure we can count on little Timmy waking up from his nap this afternoon with a very wet diaper.?

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