“What do you think you’re doing?” I knew the voice and I could feel the blood drain from my face. I was standing in her bathroom wearing a terry towel pinned like a diaper, some plastic pants I’d tried to sew from an old shower curtain, and a pair of her pink panties over the plastic showing beneath a mini skirt that belonged to my older sister.
Having struck what I thought was a cute pose with my hand between my legs I remained frozen.
“Stephanie! Come in here! You have to see this! And don’t you move even a muscle!” She said to me when I started pulling my hand away.
“Holy shit!” Stephanie said as she came to a stop in the door. “That’s my cheerleading skirt from high school!” She began to laugh.
“You should know that I found the plastic pants you made and checked my panty drawer. I knew something was going on. No! Don’t you dare move that hand!”
“Mom!” I said, feeling my face turn crimson.
My stepmother was tall, big boned, and about the most beautiful woman I’d ever seen. Dad married her after the death of my mother in circumstances that scarred me for life. But she’d come into my life when I was three and I’d loved her from the first moment I saw her. Stephanie, her daughter from her first marriage, was almost a mirror image.
It didn’t seem fair to me that I’d been caught this way but there was nothing to say. Tears filled my eyes and overflowed down my cheeks.
“Take it all off.” My stepmother said, her green eyes dancing with laughter.
“Not in front of Stephanie!” I wailed.
“Right now! Take it all off.” She said, her hands going to her hips. My face flushed with shame I removed the skirt, panties, plastic pants, and terry towel. I could feel my penis growing hard, despite my efforts to control things.
“Run a bath, a bubble bath, and get in the tub. Then I want you to drink this.” She went to the sink while I was drawing the water and pouring the bubble bath. I slipped into the tub and she knelt beside me. I drank the water.
“Did he just pass out?” Stephanie asked.
“I’m going to shave him.” My stepmother said with mischief in her eyes. She proceeded to shave what little hair I had, all of it in the pubic region. I was one of those rare blonde men who grew almost no hair.
I woke up so relaxed and feeling so light I wanted to giggle. The sight of Stephanie and my stepmother silenced me. Mom rinsed me off, drained the tub with me standing in it, and poured and rubbed a scented baby oil over my entire body. Stephanie helped dry me.
“Now go in my room and lay down on my bed with your head and feet to either side. Let your legs dangle over the edge of the mattress. Go!”
I went, like a whipped puppy dog, passing my stepsister with a face that felt as though it might burst into flame. Her gentle pat to my bare bottom didn’t help.
“What are you going to do, Mom?” She asked following her out of the bathroom and into the bedroom.
“I’ve been waiting for this.” My stepmother had a triumphant tone to her voice. Walking around the bed she went to her dresser and pulled out the bottom drawer. I’d never ventured beneath the panty drawer on top and had no idea what horrors she hid there. I closed my eyes.
“Open your eyes, Sissy Baby!” I didn’t know what to say, and was sobbing.
“Mommy, please!” I cried, then bit my lip when I realized I’d called her Mommy instead of Mom.
“Oh! I like when you call me Mommy, sweetie! Open your eyes.” Her voice was pitched in the way that always made my heart melt. I loved her so deeply I had been her slave from the first moment she spoke. My eyes popped open and tears dropped wetly.
“I’m sorry! I’m sorry!” I sobbed. Then my voice failed me as I saw the stack of diapers in her hands, the baby powder perched on top, and bright yellow rhumba pants with white frilly laces and yellow trim. There was white silk at the legs and waist, and a pretty white bow in front.
For a moment everything around me seemed to be closing in on me, growing dark at the edges. Then darkness took me.
“Did he just faint?” Stephanie asked.
“I think so!” My stepmother said.
I came around just as she finished pinning one side of the three diapers she’d stacked, slipped beneath my bottom, and powdered liberally. All I could smell was baby powder, lotion, and something elusive, something that stirred my memory. She pulled the other side tight, pinned it, and then slid the rhumba pants over the diapers.
The silk, gently rubbing over the vinyl pants beneath, and on my skin was exotic. Mommy gently smoothed her work, working both hands gently from between my legs up and the release was wild as she put her lips to my tummy and tickled me with her nose.
I was at the same time intensely excited, more than ever before, and filled with shame. Mommy let her hair tickle my tummy and then stood up with laughter in her eyes and on her lips.
“Did that feel good Sissy Baby?” Stephanie asked, sitting beside the bed and taking my hand in hers. I couldn’t speak so I simply nodded my head. “Good.”
“Sweetie, you should never be ashamed of what just happened!” Mommy said gently. “I think it will happen often, and it is merely a natural reaction to your fantasy world.”
Stephanie helped me to a sitting position and Mommy slid the powder-blue cheerleading skirt over my head, and then a matching silk teddy top, feeding my arms into the openings and settling everything. Then she pointed to her oval mirror where I could see myself. To say I was fascinated would be an understatement.
Both of them moved to the door of the room and waved for me to follow. When I stood and took a step I looked down at my feet in surprise. Heavy weights were strapped to each ankle with a bar between them. A strap from each weight was also attached to a heavy square pad that slid over the floor.
The purpose of the pad was immediately clear as I plopped to my well-padded bottom squarely on the pad. To get up I had to pull my feet right up against the diapers. Twice more I fell immediately upon taking a step and knew suddenly that if this continued I’d end up with my balance vastly altered.
I held up my arms and Stephanie and Mommy took a hand and lifted them above my head. Whatever mommy mixed in the glass I drank before the bath still had my head feeling as though it were filled with fluff. When I fell again they laughed and mommy suggested crawling.
Crawling was much easier but still cumbersome with the weight at my ankles and dragging behind.
“We’ll have to redecorate his room.” Mommy said when I’d been helped onto my bed. My hands were exploring the exotic feel of the rhumba pants and mommy slapped them away. “Only we get to touch those!” She said sternly, pushing me over on my tummy and swatting my bottom hard.
“From now on you wear baby girl clothes when you’re at home, and I’ll dress you for going out.” Mommy said, pulling me back and hugging me. “Don’t move. We have to get some things ready for you, Sissy Baby.” She added, kissing my hair.
Together they tethered my hands to the sides of my headboard and my ankles to the foot of the bed. I had some movement, but not much. Still, it felt so good laying there in thick soft diapers and silky rhumba pants I thought I might have another explosion of pleasure. Things were certainly progressing that way as I discovered that certain movements caused gentle tickles to help things along.
My eyes had been closed but I opened them when I felt the bed move. Stephanie stood above me, her legs straddling me so that I could see right under her short skirt. She wore bright red panties beneath the skirt. Suddenly she folded to her knees, her bottom just touching the front of my rhumba pants. That was all it took to sweep me away once again.
Someone thrust a nipple in my mouth and passed an elastic strap over my head. The nipple was snuggly held in place and gallons of liquid began to pour into my mouth. Because I was so excited I gulped it down and discovered I couldn’t stop. How much liquid I drank was something I couldn’t begin to fathom but at last the sounds of air coming through the nipple indicated an end.
Almost immediately the urgency to pee rose to a fever pitch and my bladder suddenly seemed to explode into the diapers. Warmth spread between my legs, spreading up my bottom, running around the sides. The rhumba pants didn’t leak!
“That worked pretty fast.” Stephanie said.
“Two liters of liquid with some special herbs and chemicals will do that.” Mommy answered. The nipple was still in my mouth and suddenly more liquid was flowing in so fast I had to gulp it down to keep from choking. After two more liters I fell fast asleep and soaked the diapers twice more until they were sodden, heavy, clammy. It all felt wonderful.
I had to walk into Mommy’s bathroom for cleanup and changing. They kept my hands above my head as I waddled with the cumbersome weights at my ankles. Once in the bathroom I was untethered, undressed, and helped into the tub.
“I think he’s eating up this attention.” Stephanie said as she washed my hair with baby shampoo. I was so dizzy I couldn’t have reacted to all those ministrations if I wanted to. Whatever herbs mommy mixed were certainly having an affect.
“Come on Sissy Baby. Time to get some diapers on that cute little bottom of yours.” Mommy said after rubbing in baby lotion. I hadn’t even realized I was dried and out of the tub!
“What’s that for?” Stephanie asked as Mommy clipped the reservoir from a condom.
“He’ll rub himself raw if we don’t protect him. I want him to enjoy every moment in diapers.” I watched as she carefully attached the condom. When I began to swell she flicked me hard down there. “Not yet!” She said when I winced.
This time I was as passive and relaxed as a rag doll. I felt the thickness of the diapers between my legs, and the sensations of the rhumba pants stretched almost to capacity to cover them. When mommy smoothed her work I was suddenly panting, the pressure mounting, until I released it all into the diaper, feeling the warm sticky ooze spread.
“I think he likes it!” Mommy said, pulling her face away from my tummy where she’d been nuzzling me as I giggled and kicked in delight. As my suddenly limp appendage shrank to normal size I began to pee. It lasted a long time and felt so good. My eyes closed and I slept.
After a week I no longer felt strange trying to walk or crawling with the weights attached. The excitement of diaper changes was something to look forward to. Wearing pink, yellow and milky white vinyl pants, rhumba pants, silky clothes and cute girly things never ceased to please me.
Each morning, after my first bath, Stephanie applied makeup, curled my eyelashes, and put pink lipstick and clear lip-gloss on my lips. I spent hours sitting in Mommy’s bedroom in front of that oval mirror just looking at the thick diapers between my legs, my pretty made-up face, and the wonderful clothes I wore.
My room slowly changed around me. It became a nursery filled with yellows, lavenders, pinks, blues, and other pastel colors. Above my bed a mirror had been attached to the ceiling so I could see myself in my sissy baby clothes.
Weeks turned into a month, then another, as I celebrated my summer break between high school and college living my most intimate fantasy. The weights came off one day and I did indeed walk very much like a toddler, much to my delight. Every other day I wore the weights, to keep training was the reason Mommy gave.
The sexual stimulation of diapers and vinyl pants seemed to grow, rather than fade as I became used to wearing sissy baby clothes. There were days when I would squat down in front of the full-length mirror on my wall, my skirt riding up my thighs and revealing the thick diapers and vinyl pants or rhumba pants beneath. Just the sight of them turned me on. I would plop down and move my legs in just the right way to bring myself to a delightful tickling conclusion.
“What’s that for?” Stephanie asked one day while I lay stretched out on mommy’s mattress, three thick diapers already under my bottom. My eyes were closed so I was very surprised when something coated with Vaseline was thrust into my rectum.
“It’s a butt plug.” Mommy said. She was smiling as I grew hard.
“Interesting reaction.” Stephanie said. As soon as the diapers were pulled between my legs I came in sweeping abandon, spraying the diaper and part of mommy’s arm as I panted and made mewling sounds. Perhaps thirty seconds passed before I was spent, slicked with sweat, and swallowing hard.
The butt plug was unfair. Every time I sat it spread wider making me jerk to hardness instantly. If I peed it was a turn-on! Then, as the day passed, I felt the need to empty my bowel, but I couldn’t. Within half an hour of that first sensation I could feel the need growing, and with it my helplessness.
In the late afternoon mommy changed me, removing the butt plug and ordering me to hold it. As she smoothed her hands over the front of my vinyl pants and I climaxed my bowel released too, soft poop pushing the diapers out and then spreading up the back and front when there was no more room.
I was panting with pleasure. Then they lifted me from the bed, and I took a step and fell plop onto the pad, spreading the mess further, wondering if it was going to leak out the top of my vinyl pants.
Neither of them seemed to mind the bother and cleanup. Both wrinkled their noses at the horrible smells coming from the diapers but cleaned me without comment. After a bath I begged for the plug again and with an understanding smile mommy inserted it before pinning the diapers.
Biting my lip and arching my back I held everything back until her hands moved over the rhumba pants. She flipped me to my tummy and gently rubbed my back, with just the tips of her fingernails until I moaned, made mewling sounds, and helplessly kicked my feet. She kept it up until I was sound asleep.
“We’ll take you out tomorrow.” She said softly, patting my bottom as I dreamed sweet dreams.
My blonde locks were much longer now, naturally curly, and I looked at myself in the mirror when I was dressed to go shopping. My diapers peaked out from beneath a pleated mini-skirt. The top I wore left my tummy exposed. I looked like a girl, almost pretty, mostly cute.
Because I was only five feet tall, and slender of build, without removing the diapers no one would ever guess there was a boy hiding beneath it all. The thrill of being taken into public dressed this way was almost more than I could bear!
Stephanie came in and stood behind me. I felt small as I looked at her reflection, head and shoulders taller, beautiful and shapely. She leaned down, put her face next to mine, and wrapping her arms around me put her hands gently between my legs and patted me. Laughing at my suddenly weakening knees she followed me to the floor, still patting.
“I have power over you, sissy baby.” She said softly when I was spent. “I think I like it almost as much as you do!”
We didn’t just go for a short jaunt. All day we shopped, with me sitting in a stroller made for adult babies. Mommy said she ordered it online from the same place she bought my diapers and baby things. The stroller was a surprise, and I felt wonderful being pushed about.
Sitting on the butt plug didn’t disturb me in the least. Nor did wearing increasingly wet diapers. I drank three bottles of liquid from a “big baby” bottle before lunch. Mommy took me out to the car to change me and pushed me back inside wearing nothing but diapers, rhumba pants, and a cute top.
Then we were driving home and Mommy was telling me what a good sissy baby I was. I had to poop, but said nothing. Mommy wisely sat me on the toilet seat before removing the plug. My disappointment in not messing my diapers was a tangible thing. She smiled at me and wiped me with baby wipes.
“Let’s get you bathed and into diapers, sissy baby.” She said softly.
As a reward for being such a good girl she added a diaper, making me very happy. Thicker was always better in my mind.
While Mommy and Stephanie watched television I sat in the playpen and played happily with my toys. If I wanted a bottle I would ask for it appropriately.
“Baba mommy, pwease?”
As they put me to bed that night Stephanie ruffled my hair. “I’m having some friends over for the weekend. They’ve been begging to come see my special little sissy baby sister. Won’t that be fun?”
I giggled at the thought. She smiled gently moved her hand through my soft curls until I was sound asleep.
Stephanie and Mommy planned the weekend carefully, making it very special for me. I never asked them why they loved to keep me in diapers and treat me like a baby girl, nor did I question their absolute control. They certainly seemed to enjoy my eruptions of pleasure and almost complete dependence on them for everything.
Stephanie was part of a group of girls who called themselves the Green-eyed Gang. All of them had pretty green eyes and every one of them turned every male head on the college campus. Most of them had been elected as homecoming queens, community queens, May queens, or won beauty pageants. Yet they were as different as girls could be.
I secretly thought my mommy was the most beautiful woman in the world, and Stephanie a close second. Perhaps mommy knew how I felt about her. At times she would catch me staring at her and raise an eyebrow as though to question what I was thinking. All too often I was wishing I could nurse from those too tempting nipples on her beautiful full breasts.
The girls were gathered in the great room, talking about their summer, laughing and sharing the funny experiences, and treating me as a special guest. Every one of them bent over the playpen to tussle my hair and talk baby talk to me. It surprised me that I was the smallest person in the room, and secretly pleased me.
Mommy and Stephanie lifted me out of the playpen and let me plop to the floor where I began to crawl, following them up to the bathroom for a change. All of the girls came and watched, filling the bathroom with laughter and girl-talk, as if what was happening to me was normal every day stuff. I’d had a bottle before coming up and my head was full of fluff, a pleasant foretelling of delights to come.
Suddenly I was standing in a bathroom full of girls while Mommy rubbed in scented baby oil, baby lotion, and diaper rash cream. I loved the smell of Desitin diaper rash cream. When I’d been cared for I walked with toddler steps to her bed naked and unashamed.
My eyes were closed and my lips parted in anticipation as the diapers were slid under my bottom. Mommy poured powder on me and I knew the plug was next. Right away I could feel it was different, but I didn’t know how. Feeling myself grow hard my toes curled and stretched.
Mommy tapped me, calming me and telling me it wasn’t time for that yet. I blushed deeply and when Stephanie put a pacifier in my mouth my tongue was hungry for the pleasure of suckling the nipple. Once the diapers were tightly pinned in place Stephanie pulled the rhumba pants up.
Her fingernails were long and she used them to make me suddenly tingle all over as she gently trailed them along my inner thighs. Something happened to the butt plug. My eyes popped open and the pupils dilated as the motion began. It felt like something inside the plug was pushing out against me, and deep inside me, pulsating slowly. Then the vibration began inside me.
The mewling sounds coming from behind the pacifier were urgent as my breath caught, then came in faster and faster gulps. Mommy lowered her head to my tummy and began to nuzzle me and I came in sweeping waves as never before, while something tickled that special place on my penis and the gentle thrusting and vibration in my rectum took my breath away.
Even when it was over I trembled, goose bumps covering my body now slick with sweat and smelling sweet as the oils released their scent. Mommy held me then, patting my bottom while I nuzzled her and breathed her in.
“I wuv you mommy.” I whispered in her ear. “I wuv you so much! I wish I could be as beautiful as you. I wish I could nurse fwom you.” Never having put it in words like that I was surprised when she unbuttoned her blouse, removed her bra, and gently guided my lips to her nipple. Stephanie knew. I’d told her once how much I wanted it. I wept as I suckled, and felt warm milk flowing, sweet mother’s milk.
“He’s very gentle.” She said in a quiet whisper to Stephanie.
“He’s also out!” Stephanie said with a smile.
“Let him nurse.” Mommy said. They were the last words I was aware of.
During my nap I soaked the diapers twice, unaware of the pleasant warmth flooding against my skin. When I woke up I lay like a rag doll in Mommy’s bed, my nose buried in one of her breasts, my lips still locked around the nipple. She was sound asleep too.
It was Stephanie who broke the suction by inserting a finger between my lips and that precious nipple, and pulled me away. She motioned for me to be silent and carried me into the bathroom easily. There she undressed me, removed the butt plug and the device that had tickled me in just the right place, the condom, and wiped me clean before putting me in the tub.
Two of her friends helped diaper me while all the sensations that were so new had me giggling and kicking my feet helplessly while Stephanie nuzzled my tummy. Mommy remained asleep but smiled when she heard me.
Later in the playpen I sat quietly, playing with some plastic rings of various colors when the plug began to move inside me. I giggled and lost my pacifier, sitting there drooling down my pretty pink dress, while the girls watched in fascination. I could feel my breathing quicken and I kicked my feet, making the still dry diapers tickle me just so.
The tickling began so gently I couldn’t really tell if it was just the diapers and powder or the device, but I suddenly squealed in delight as the butt plug seemed to expand and push inside me, and the tickling got stronger and stronger until I my feet had a life of their own and my body throbbed with pleasure. It lasted a long time and then I peed, while the tickling kept going and the plug kept moving inside me.
“Oh honey! You’re all wet in front!” A girl named Zoey said, wiping away the drool. She pulled off my pretty dress and left me in my diapers and rhumba pants. She gave me a bottle and watched me fall backwards and kick lazily as I drank.
“How did you get him so docile?” She asked Stephanie.
“She’s always been easy to manage.” Stephanie said, and then laughed. “I mean he. But he isn’t really a he anymore. I think “she” is the appropriate term. Am I right sissy baby girl?” I giggled and squealed and kicked my legs.
Later that night the girls undressed and paired up on air mattresses all around me. I’d had several bottles and my diapers were very wet. Before going to bed herself Stephanie helped me up the steps and Mommy and she bathed me and talked baby talk to me. When I was diapered again I put a gentle hand on Mommy’s breast.
“You are such a baby!” Mommy said with a sigh, pulling her T-shirt up so I could nurse. It was some time before she brought me down to the playpen where I was to sleep for the night. She put a bottle in my mouth and smiled at me, then patted my vinyl pants twice before going up to bed.
I guess the girls were turned on by what they’d seen happen to me because as I drank the bottle they began to please each other. Never having seen this before I was riveted. Some bit their lips in ecstasy, some kissed passionately as their bodies released, and some shrieked in waves of pleasure.
One girl rose to a climax and when her partner kissed her passionately seemed to explode in ecstasy, making soft whimpering sounds while her breathing quickened to yet another climax before she was spent.
Another bent over her lover and nipped an ear as she came beneath her, while her lovers hands groped and moved until they were both moaning together in delight. I lay placidly, patiently waiting, for I knew that Stephanie would not forget me.
When they lifted me out of the playpen a blonde with enormous breasts tossed her hair and pulled me to her breast. They massaged me gently while I suckled, being careful to be gentle, while gentle hands rubbed over my vinyl pants.
Stephanie smiled at me, kissing my cheek and tussling my hair, showing me the remote control she’d been using. When she pressed one button the motion in the plug began. I was, by that time, flat on my back, my legs moving in and out with the motion of the plug.
One of the girls appeared with a large jar of Vaseline that she opened and scooped a huge handful from. Her hand went down the front of my diaper and began to smear the jelly everywhere. When one jar was empty another was opened until my diaper was coated front, back, and sides.
Then the tickling began in that special spot and the butt plug seemed to thrust deeper into me, stretching wider and wider. Sometimes the climax would build quickly. This time it was a gentle tickle that just got better and better and better until I came and came and came. Somewhere in the middle Stephanie pulled the butt plug out and my bowel and bladder both emptied.
They laughed as I tried to move in the playpen. The vinyl pad had been coated with Vaseline, along with my body, so that I could neither stand nor crawl. The mess in my diaper spread up the front and the back but did not escape the diapers despite their slippery condition.
Befuddled by the drug in the bottle I was soon so helpless I could not even roll over, though I tried for some time until another climax swept me away. Sometime late in the night I was bathed and changed and put to bed with all the gentleness and sweetness any baby could desire.
“These girls are going to care for you when you go to school.” Mommy whispered to me as the girls hugged her and filed out one by one after their amazing weekend. She was holding me in her lap and when the last girl left and the door closed I lay placidly against her, feeling the rise and fall of her soft breasts as she breathed.
She and Stephanie walked me up the steps to be bathed and changed and I sat between them as they watched TV that evening after dinner. After four bottles it was time for another change before bed.
“We have a new surprise for our sissy baby girl!” Mommy announced as she pulled the plastic pants over my diapers. She’d used four again with lots of baby powder. They pulled me to a standing position and helped me to my room. From the beam in the center of the room something new hung.
It was a baby swing, but made for adult babies. They helped me into the harness. It was thick and had a silk lining on the inside. My legs were spread wide as the electric winch lifted me from the floor. The swing was designed so that my head was supported and I lay back slightly. Attaching a strap to both sides another electric motor was engaged and the swing began to move back and forth at a gentle pace.
I held a two-handle baby bottle to my mouth and suckled passively until the butt plug was activated. The delightful motion of the swing, the tickling, and motion of the vibrating and thrusting butt plug sent me into a dizzy orgasm. Almost as soon as it was over I wet my diapers, giggling as it all started again.
Each back swing moved my bottom so that each forward swing was like a gentle thrust. By the third climax my eyes were closed, my head to the side, the bottle held by one hand as I continued to suckle.
Half asleep I was lowered to the floor and helped into bed where my gentle kicking swept me away once again. Twice that night I dreamed of trying to pee while one or all of the green-eyed gang looked on. Those were always the wet dreams and were followed by actual wetting.
In the morning the diapers were heavy and my legs weak. I loved waking up with soaked diapers, and crawling to the bathroom to be changed. School was coming soon, and I wanted to enjoy every moment of time with mommy. She sensed my desire and kept me close.
“You were four when I potty trained you, little one.” She said that morning as I rested against her in the living room. “I’ve regretted doing that all these years. So I’m just going to keep you in diapers now.” There was no possible way she could understand just how much I wanted that or how deeply I enjoyed those words.
I didn’t want to be anything else. Sighing with pleasure I let my head rest against her soft breasts, breathed in the fragrance that was her, and smiled.
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Caught! (a Story For All My Sissy Baby Friends!)
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