The Continuing Adventures of Baby Bobby

[Anonymous]

My mom, rather than sending me back to public school, decided to enroll me in home schooling, much to my relief. My nanny Tiffany was particularly well suited to administer the studies as she used to be an elementary school teacher several years ago and was quite familiar with how to maintain classroom discipline. Her rules were very simple; for every problem I missed on a test, my diapers would be pulled down and I would be given a harsh swat from the paddle. During the first couple of weeks, I received numerous painful lessons everyday and I was made to sit on a stinging bottom, uncomfortably shifting in my seat while I corrected my errors.



   It didn't help matters that I was hopelessly distracted by Tiffany, with her tight skirts and tops. Since masturbation was strictly forbidden by her, I was constantly horny as hell with no way to relieve myself. I couldn't do it in bed because my crib had really old, squeaky springs in it. Any movement within it sounded like an earthquake on the baby monitor that was kept in the nursery. If I were to begin to establish any kind of rhythm, my mom would be up immediately to check on me. And Tiffany made a point of ensuring that I was never alone, unless she let me outside to play in the front yard, and I could hardly diddle myself there.



   I often wondered if she had been a model previously. She was certainly pretty enough to be one, but of course, she never talked to me about herself. She was tall enough that when she was in her heels, which was just about all the time, my eye level would be at the height of her tremendous boobs. There wasn't a day that went by that I didn't fantasize about suc-kling from those huge, perfectly shaped bre ( " at " ) sts but I had to be careful about staring. If she was in the mood and she felt I had been leering at her, she'd give me a harsh slap on the face and threaten worse if I didn't behave myself.



   However, there were times like today when I just couldn't help myself. I was sitting at the table while she was discussing the finer elements of geometry to me. She'd bend over the table to explain a point and I'd gaze hungrily down her partially unbuttoned top, her big bosom threatening to burst out of her lacey bra. As she breathed, I noticed that her chest would rise and fall, and I caught myself on the verge of drooling. Her heavy bre ( " at " ) sts pressed together forming a deep cleavage that was sending me to the brink of orgasm. The perfume she wore surrounded me and a strand of her long sensuous hair fell down and tickled my cheek.



   My pen-is grew rock hard in the soft folds of my thick diapers and I could tell the tip was slick with pre-c-um. My heart was beating rapidly and my mouth was dry from sexual tension. I waited until she turned around and then the second she walked back to the blackboard, I rubbed my wee-wee furiously through my diapers and plastic pants, hoping to achieve climax before she turned back around. However, before I could make good on my plans, she spun around when she heard the crinkle-crackle of my panties and caught me red handed.



   "What do you think you're doing!?" she demanded angrily.



   "I-I-I...I was just..." I stammered in a panic.



   She walked the few steps to stand before me and put her hands on her hips, her massive bre ( " at " ) sts thrusting out proudly before me.



   "You were masturbating again, weren't you?!" she said accusingly.



   I knew there was no talking my way out of it, I had been caught again.



   "Y-yes Ma'am," I mumbled as I stared at the floor.



   "Well I know just the way to clean those dirty thoughts out of your head," she assured me as she grabbed my wrist and yanked me to my feet. She pulled me along towards the bathroom where she retrieved my enema bag and she sat me on the toilet while she filled it as far as it would go with warm soapy water.



   "Come along," she said after sealing the top and donning her plastic apron. She pulled me into the nursery and unceremoniously pulled my plastic panties down, taking me over her lap. After flipping up the hem of my dress and petticoats, unpinning my diapers and pulling them back, she dipped the dripping rubber dil-do nozzle into the petroleum jelly and inserted it into my quivering anus. I moaned helplessly as she released the clip and the first surge of water gurgled into my backside.



   "A nice long, soapy enema is just the thing to purge those nasty thoughts of yours," she explained as she allowed the water to flow uninterrupted into my rectum. I whimpered helplessly as the cramps set in and I fought to keep out the water. I pinched my cheeks but that did nothing and all I could do was lie there and take it.



   After five minutes, I lay gasping from the pressure and finally I heard the last bubble filled stream gurgle into my bottom. Thinking I was done, I struggled to get up but Tiffany held me in place.



   "Not so fast Bobby," she warned me, "we need to have a little discussion."



   I felt her extract the enema nozzle but then felt a blunt, greasy object being pushed firmly into my hole. I squirmed in an attempt to escape the rubber invader but no sooner was it taken away when I felt the stinging impact of the paddle on my fanny. I yelped in pain but it came crashing down again and again, leaving its harsh red signature on my tender cheeks.



   Tiffany paused and I felt the butt plug once again being pushed into my hole.



   "Spread your legs and open wide Bobby, that's it, wider...wider...that's it, just relax and it'll go in easier. I know it's big but a big sissy like you can handle it. Just relax..."



   The butt plug felt tremendously large and even though I tried to obey and relax, I was sure it wouldn't fit. I moaned in pain and anguish but Tiffany just kept pushing insistently on it.



   "Ooohh...OOHH!!" I squealed as it finally popped into place inside me.



   I had never had a butt plug in me and I soon learned I was helpless to push it back out.



   "Now, we're going to have a little discussion, you and I," Tiffany told me as she rubbed the wooden paddle slowly across my bottom.



   I immediately tensed up in fear of what was about to happen. The only way this was going to end was when she had blistered my bottom and reduced me to a bawling crybaby. Crocodile tears formed in my eyes and I whimpered anxiously, praying for respite.



   "You've been acting very childish lately, doing things you aren't supposed to be doing. Like staring at my bre ( " at " ) sts."



   I felt the paddle crash down on my derriere fiercely, and I bellowed out in pain.



   "And today, you thought you could masturbate right in front of me."



   Again, the paddle seared itself on my bottom.



   "What have you been told about masturbating?" she demanded impatiently.



   "I-I I've been told that i-it's naughty," I quaked uncertainly.



   SMACCKK!!!



   I wailed in pain and kicked my legs.



   "That's right little boy, it is naughty. And you've been told that a thousand times, haven't you?" she continued.



   "Y-yes M-Ma'am," I answered shakily through sobs.



   SMACCKK!!!



   I howled loudly, flailing wildly on her lap.



   "Then why do you keep doing it?!"



   "B-because...because I'm so horny," I blurted out tearfully.



   SMACK!! SMACK!! SMACK!!



   She spanked me hard and furiously for several seconds.



   "Don't you EVER say that word in this house again, DO YOU UNDERSTAND ME?" she demanded angrily.



   "Y-yes Ma-Ma'am!" I blubbered. My acknowledgement was cut off by another flurry of stinging slaps from the paddle. I cried out, the tears flowing down my face freely now and my breath coming in short, ragged gasps. I kicked my legs but as usual, they were tangled within my plastic panties and my mary janes beat out an uneven rhythm on the floor. Looking down, I saw Tiffany's white high heel pumps and her sexy calves but their image was lost on me as she fiercely paddled away at my poor fanny. My stomach had been churning previously but now my bottom was the stinging priority.



   Again and again, my nanny smacked my behind, each swat with the paddle carefully designed to redden my cheeks thoroughly and cause maximum sting. It felt like a blow torch was being held to my rump and I sobbed and cried like a baby. With professional thoroughness, she spanked evenly all over both blazing red globes, making sure every square inch received it's just punishment and was properly reddened.



   At last, she relented, helping me up and taking me to the bathroom. I staggered uncertainly, my panties forming a ring around my ankles and the butt plug still buried in my rump. Tears streamed down my face and I sobbed loudly as I tried to remove it.



   "When you're finished in there, come back in here and I'll re-diaper you," she directed me.

[Anonymous]

When I came out of the bathroom ten minutes later, Tiffany was waiting with a fresh diaper and plastic panties on the changing table. Pushing a warm bottle of formula into my mouth, she sat me down on the triple thick diapers and busied herself powdering my bottom and genitals. I tried desperately to ignore her incredible bre ( " at " ) sts as they were displayed in front of me, pressing tightly against her partially unbuttoned top. To keep from getting an erection, I tried to think of something else, so I concentrated on John's coc-k instead, thinking that just the opposite would keep me limp. Unfortunately, for some reason, the thought of his big hard coc-k pumping in and out of my mouth and stretching my cheeks to accommodate him caused my own powdered wee-wee to immediately harden. Tiffany noticed it and grabbed its tiny shaft roughly, pinching it between her manicured fingers and causing me to cry out in pain.



   "What's going on here?" she demanded.



   Without waiting for an answer, she grabbed the paddle, held my ankles up over my head and exposed my freshly powdered but still red fanny. I cringed as I tried to steady myself with my hands on the plastic surface of the changing table. I could do nothing but watch as the paddle swooped down again and again on its avenging mission, smacking my bottom and reviving the sting while bringing forth a fresh torrent of tears.



   She stopped when she saw that my erection had gone down again and I lay on my back, blubbering like a baby.



   Tiffany set down the paddle and continued with my diapering as if nothing had happened and she pulled the thick, baby soft cloth between my legs and pinned it on either side with oversized pink ducky pins.



   "Maybe that will teach you a lesson," she admonished me as she shook out my nursery print panties and pulled them over my feet. I suc-ked on my bottle and watched with tear filled eyes as she pulled the panties down my upraised legs and wrestled them over the thick, bulging diapers.



   "There," she said as she hung up the paddle, "mommy's little baby's all diapered again. Why don't you go outside and play for awhile."



   Still sniffling and whimpering, I waddled out of the room and went outside, deciding to play on the swing in the backyard. Tiffany saw me and stuck her head out the window, giving me a look that said she didn't approve.



   "No, I want you to play in the FRONT yard Bobby," she told me.



   Pouting and muttering under my breath, I trudged around the house to the front yard, now completely exposed to whoever should be passing by, not to mention our neighbors. As I played idly with the dollhouse set up on the grass, passing cars would slow down and stare at me, unsure if I was a girl or a boy but certain I was too old to be wearing diapers and plastic panties. They would honk and whistle at me and I blushed with embarrassment. To make matters worse, my bottom was still stinging and it hurt to sit down. It was better if I played on my hands and knees but that pose made my thickly diapered fanny stick out even more.



   A few teenage girls were driving by and they slowed down to get a better look at me. I couldn't hide behind the dollhouse because it was far too small and the girls teased me mercilessly.



   "Hey sissy boy, you better get your mommy to check those diapers."



   "You look like a big baby."



   "Nice plastic panties, little boy."



   "Where's your mommy, Baby?"



   I sniffled and pouted, unable to say anything in my defense and eventually they tired of teasing me and drove off. I had just set up Barbie's tea set when Dixie's car pulled into the driveway. She stepped out with John and what looked like a body builder, a hunky man wearing a muscle shirt. I blushed as they walked toward me and I noticed a distinctive bulge in the tight bicycling pants the body builder was wearing.



   "Hope you're hungry, Bobby," Dixie said mischievously, "I see you eyeing Hank's coc-k."



   "Oh no, Ms. Dixie!" I denied, blushing furiously, "I wasn't!"



    "Don't worry, he'll let you suc-k it, if you're a good sissy," she chuckled, "Today's your big day and I've got a big surprise for you."



   I wondered what it could be as I saw Tiffany step outside, her keys in her hand.



   "Thanks again for agreeing to baby-sit on such short notice, Dixie," she said as she unlocked her car door.



   "No problem, Tiff," she replied, "I've got your little sissy all under control."



   The look she shot at me told me I better not argue with her.



   "See you in a couple hours," Tiffany said as she closed her door and started the engine.



   Ignoring me, Dixie and the two men went inside and later I spied them through the window drinking beer and laughing. Thinking I could sneak inside and get past them, I went through the backdoor but Dixie saw me and stopped me, blocking my path with her arm against the fridge. I stared at her big perky bre ( " at " ) sts that filled her thin pink top, every curvy detail apparent in the stretchy fabric.



   Why don't you come into your nursery Bobby," she said with a devious but ravishing smile that took my breath away. I followed behind her and found the other two already waiting for us.



   "Our pampered princess has decided to join us," she announced to them.



   Both men looked at me lustfully and my heart began beating like a bass drum. Dixie led me to the center of the room where Hank began peeling his snug fitting pants off. He was definitely ALL man, with huge muscular arms and a barrel chest, his legs like two huge tree trunks. Under his pants he had on thin, Speedo type underwear which barely contained his large, growing erection. My jaw dropped when I took in the hardening pole that was rapidly straightening out from his crotch. It looked bigger than a long, fat cuc-umber and Dixie guided me to my knees before him.



   "Hank tells me he hasn't c-um in a week so I hope you're prepared for a mouthful," she told me.



   I barely had time to lick my lips when he pushed his gargantuan coc-k into my mouth, stretching my cheeks to try and take him all the way in. Of course, I could only get about half of his long shaft in me before he bottomed out, his thick pulsing head pushing against the back of my throat. I tasted salty pre-c-um as I swirled my tongue around his head and suc-kled the massive fleshy lollipop.



   He moaned and put his hand on the back of my head, taking hold of my pigtails and guiding me into a slow sensuous rhythm. My mouth was so full of big meaty coc-k sliding in and out that I almost missed the fact that someone was peeling my waterproof panties down. When I felt my diapers being unpinned and folded back, I started to get nervous and my eyes widened in panic. Soon, I felt John's huge finger, slippery with vaseline as he pushed it into my virgin hole. I squealed and squirmed but Hank's firm hold of my pigtails, prevented me from escaping. I waved my hands and tried to say no but with a huge coc-k thrusting down my throat, all I said came out muffled and wimpy sounding.



   Dixie came around to where I could see her and she smiled down at me, immensely satisfied.



   "Now you're going to find out what happens to sissy little coc-ksuc-kers, Bobby," she said huskily.

[Baby_Bobby]

I whimpered helplessly as the big stud held me in place, his gigantic coc-k gagging me and my diapers pulled down, leaving my just recently spanked bottom vulnerable. Suddenly, I felt the head of John's huge coc-k pressing urgently against my greased sphincter. I squealed again in panic as he pulled my rosy red cheeks apart, hoping to pry my hole open. Slowly but firmly, he pushed in his head first, letting me try and get used to his massive girth before pushing the rest in. I screamed in shock at this anal invasion just as John pushed forward, filling my back passage with eight inches of his mighty coc-k. I was certain he was splitting me in two and it felt like a baseball bat had been rammed into my rectum.   

   Soon, John settled into a slow rhythm, pumping my bottom with long deep thrusts. When he pushed his giant coc-k all the way in, he'd hold it there, gripping me firmly by my hips to make sure I took in every inch. Then he'd pull it out far enough to just keep the head inside before sliding it all the way back in until he bottomed out. Each time he did so, I'd squeal like a little girl and flail my free hand.

   Dixie was thoroughly enjoying the show and from her purse, she produced a camera. She took several close ups of my face as Hank's thick coc-k slid in and out, shiny and slick from my saliva. Then she backed up a couple of feet to get shots that clearly showed my red sissy bottom being humped by John. Each click of the shutter brought new color to my blushing cheeks which were stretching wide to be able to fit Hank's titanic phallus in my mouth. Dixie was giggling with each shot and making humiliating comments to me.

   "Now you know what it means to be a COMPLETE sissy Bobby. Hope you're enjoying it because this is the only sex you're ever going to get."

   Hank was smiling down on my bobbing head, still holding me by my pigtails as he rammed his big coc-k down my throat.

   I had to admit, in my secret heart of hearts, that after the initial pain of John's rear entry subsided, his massive coc-k was starting to feel pretty good as it slid in and out. I had never felt so full and I imagined that this must be what it was like for a woman to be ravished.

   To help brace myself, I cupped my hands on Hank's firm buttocks, stroking them gently as I worshipped his coc-k with my lips and tongue. Soon, I felt his buns tense up and I knew my moment was at hand. Similarly, I sensed an almost imperceptible change in John's rhythm and his coc-k seemed to swell even larger.

   With a roar that filled the room, Hank rammed his coc-k against my throat and began pumping great quantities of his creamy semen into it. Like a good sissy, I swallowed immediately and then again and again. Despite my best efforts, excess c-um still spilled out of my mouth and dribbled down my chin. While Hank was c-umming enthusiastically in my mouth, John slapped my bottom and buried his coc-k inside, filling my rectum with a warm, creamy enema. The experience was too much for me and I felt an earth shaking orgasm of my own, the waves of pleasure sweeping through me and making me dizzy. This was the first time I had ever c-um without masturbating and the thought made me blush again.

   Slobbering and licking, I greedily cleaned Hank's slick pole of his juices while John kept his own coc-k still buried inside me. Reluctantly, he pulled it out of my tight hole and stood up shakily. I could feel his gooey c-um leaking out my stretched sphincter but Dixie quickly came to my rescue and re-pinned my diapers, pulling up my plastic panties as well.

   Both men looked vastly pleased and they congratulated Dixie on training me so well.

   "You were right about him being a great coc-ksuc-ker," Hank said to John, "That was mind blowing."

   "Well, he's certainly had a lot of practice," he grinned as he stepped back into his underwear.

   "Must be because he enjoys it so much," Hank suggested.

   I looked down at the floor in shame but the damp spot in the front of my diapers belied the truth of what he said.



The End