“Jimmy! Your babysitter’s here!”
I heard the familiar words from my Mommy–actually, my wife of three years–who was busy getting ready for her date in the other room. I was in my nursery, sitting on the floor, where I’d been told to wait for my babysitter’s arrival.
It still drove me crazy with jealousy to see Denise getting ready for a date with another man, dressing in her sexiest clothing, while I was destined to spend another long, lonely night in my crib. The unfairness of it grated on me constantly and not for the first time did I strongly resent our unequal relationship. On evenings such as this, I was inclined to put up a fuss and be a pest with her, so increasingly, she had relied on the services of Auntie Brigitte, our current babysitter to keep me out of her hair.
I saw the door to my nursery was soon being pushed open and Auntie Brigitte towering over me as she looked down upon me.
“And how’s mommy’s little girl?” she asked solicitously, although her tone of voice couldn’t mask her amusement.
Auntie Brigitte was a distant French relative of my wife. Despite my age, Auntie Brigitte treated me like a four year-old child and Denise had given her the task of babysitting me when she was too busy to put up with me herself.
Auntie Brigitte had taken to the job like a fish to water, enjoying her power over me and Denise had given her full authority to discipline me as needed. And despite the fact she’d been babysitting me for over a year, I still burned with humiliation whenever she came over and saw me dressed as I was.
It certainly wasn’t helped by my wife’s choice of attire for me. I was wearing a frilly pink gingham Sunday dress, anklets, and glossy black Mary Janes looking little different from a precocious toddler girl.
It looked like Auntie Brigitte had just left from work as she was wearing a no nonsense business suit and her hair was tied back in a pony tail.
“What a pretty dress you have on, Jimmy,” she exclaimed as she came over and felt the eyelet lace trimming the short hem, “Is that a new one?”
“Uh-huh,” I mumbled as I blushed with renewed embarrassment.
My wife had made it clear to me when we got married that she would be the one in charge and even gone to the extent of making me sign a prenuptial agreement/contract which established our very different roles. Basically, I was to do as she told me, whenever she told me, and without question. I had been so awed with her incredible beauty and statuesque body that I was willing to agree to anything, so long as it meant living with her. What I hadn’t counted on was her plans to gradually feminize me and lower my effective age to that of a pre-schooler.
Our first argument had ended badly for me.
She’d settled it by yanking me over her lap and giving me a blistering spanking with her wide backed hairbrush, reducing me to tears in just a matter of moments. Not satisfied with my childish display of defeat, she continued to soundly paddle me, driving home her absolute authority over me and forever relegating me to secondary status.
After that, she gradually threw out all my underwear, replacing them with lacy panties and putting me in girly dresses to wear around the house.
But it was when she caught me masturbating that things took a turn for the worse. After another painful and humiliating spanking (this time in front of my Mother-in-Law), she produced a chastity device that she locked around my shriveled penis. She had never been happy with my equipment down there and this was just another way for her to take control over me.
Initially, she was allowing me to cum once a week but that soon turned into increasingly longer stretches between my moments of (brief) relief. One week turned into two, and before long, I was only getting unlocked once a month to get a perfunctory, impersonal handjob before she locked my little wiener back into its restrictive, plastic prison.
We had only been married four months when she happily brought home her latest purchase, a stout wooden paddle with numerous “air holes” drilled in the face for extra sting. Even though I had been on my best behavior that day, she still insisted on “breaking it in” upon my pantied bottom. I was sobbing like a baby by the time she finished, and since that first day, I’ve felt it’s sting many times, often, for only the slightest of reasons.
It was not long after that, that Denise hired some workers to come in and redecorate our spare room as a baby’s nursery. A large, oversized crib dominated the room and the walls were papered with pink cartoon characters. This became my room and I was told the master bedroom was now off limits to me.
Soon, Denise began seeing other men and she made no secret of her weekly liaisons. Her mother fully approved of her plans and she would often come over to babysit me, happy to treat me like an infant and it was her idea to change my bedtimes to 7:30 every night. I knew better than to argue with her since she had shown no hesitation in blistering my bottom with Denise’s paddle. It was also her idea to extend my monthly chastity sentence to three months at a time. She assured her daughter that a big sissy like me didn’t need to cum any more than four times a year and Denise quickly agreed.
“Okay let’s put away your coloring book, Jimmy, it’s time to get you ready for beddie-bye now,” Auntie Brigitte said as she summarily closed the page I had been drawing on and began putting away my crayons without waiting for my approval.
“Aw, is it time already?” I whined miserably. I couldn’t believe it was already after seven but since my nursery had no clocks in it, I never had any way of knowing what time it was.
“Yes it is, Sissy, its time to get you changed and ready for bed,” she explained in her motherly tone, “Let’s get that dress off and then it’ll be be time for nite-nite.
I pouted as she pulled the frilly ensemble over my head and outstretched arms before hanging it up in the closet. She returned almost immediately with a pink and white fuzzy fleece diaper shirt, decorated with a Disney Princess theme. No sooner was it pulled into place than she presented me with my nightly bottle.
“Here you are Jimmy, drink up your num-nums,” she sang merrily.
I accepted the 32 ounce baby bottle with blocks and giraffes and reluctantly began nursing the warmed milk. I had begun to suspect it was laced with a mild sedative and diuretic to better control me and it wasn’t for nothing that my crib mattress had a waterproof sheet covering it.
Taking my hand, she led me over to the changing table, a low, padded and vinyl covered surface six inches above the floor to sit me down upon.
“I see your mommy has begun putting plastic panties over your trainers during the day,” Auntie Brigitte observed with a trace of surprise in her voice, “Are you wetting during the daytime too, now?”
Her pointed question made me blush furiously but she seemed oblivious to my discomfort.
“I…um, had an accident, the other day,” I mumbled as I stared down at the pink carpeted floor, unable to look into her pretty green eyes.
“Well, I’m not surprised,” she said casually, “A big sissy like you really should be in diapers all the time–not just for bedtimes. I’ll bet Denise will be making a few changes around here before too long.”
I winced inwardly at the idea of losing my last connection to adulthood, however pathetic it was.
“Please-please don’t tell her to do that,” I pleaded with her.
“Everyone knows what a bedwetter you are. If you can’t keep your trainers dry during the day, she’ll have no other choice,” she quipped.
“Now drink up Sissy,” she insisted as she put the bottle back to my lips, effectively ending our conversation, “we don’t have all night.”
I pouted helplessly as Auntie Brigitte snaked my yellow plastic panties down from my thick cotton training pants and put them aside for later use.
“Still dry for now,” she mused aloud, “Oh well, not for long.”
Down came my trainers, exposing my bald, shaved crotch and my embarrassingly minuscule penis, securely locked within its CB6000s chastity device.
Auntie Brigitte giggled as she looked down at my caged member, incapable of growing past the frustrating inch and a half limitation of its tube.
“You didn’t really think you were going to be able to satisfy Denise with this, did you?” she asked as she held my tiny package in the palm of her slim hand and gently squeezed my swollen balls.
Not sure if her question was meant rhetorically, I shrugged lamely and continued nursing from my bottle while my cheeks burned with shame.
“This is so small, it’s of no good to anyone…I think its just as well she decided to lock it up.
“How long has it been now, since you last came?” she asked as she began gathering the thick cotton diapers next to her.
“Um…two months,” I said in barely a whisper.
“Well, only one more month to go, Sissy. That shouldn’t be any problem,” she said with confidence she couldn’t possibly feel. More likely, she just didn’t care.
“No…this is where you belong,” she said as she slid a tall but soft stack of pre-formed diapers under my raised rump, “Securely pinned into a thick, thirsty set of baby diapers with some snug plastic panties to keep your childish wetting under control.”
I wanted to get up and run from the room but I was forced to sit there and endure her humiliating comments.
“Just take a look at these,” she said brightly as she held up a fluffy white diaper, “So soft and comfy, with a nice soaker strip sewn through the middle for heavy wetters like you.”
Just then, Denise strolled into the room unannounced, looking as if she were almost ready to leave.
“Hi Auntie Brigitte, how’s it coming in here?” she asked, completely ignoring me.
“Just changing the sissy into his diapers for the night,” she replied with crisp efficiency.
Looking over the top of my upraised bottle, I drank in the awe-inspiring sight of my wife, framed within the doorway. She hadn’t yet put on her dress and her fabulous body was impossible to ignore. Her tall, five inch stiletto heels lent her a commanding presence and her skimpy black thong intimated at what she had planned for later on. She certainly had never worn underthings like that when we were first dating, I reflected with gloominess.
Her tremendously big breasts were pushed up in the ultimate display of femininity, mocking me with their soft curves and deep, sexy cleavage. Only once had she ever deigned to let me touch them but that was three years ago and it seemed like an eternity now.
I felt my penis struggling to become hard within my chastity device, only to be brought to a quick and effective stop by the short confines of the tube. I bit back the groan on my lips but my heart was thumping within my chest. I was so horny I couldn’t even think straight and these two babes were totally unaware of my need.
Looking down on me with an enchanting smile on her face, I could plainly see Denise was excited about her date. It was equally clear she was pleased to see me under control–out of her hair, being put into my sissy diapers and readied for bed like an incontinent toddler.
Denise turned on her heel and I was briefly treated to one momentary view of her delicious derriere as she returned to her bedroom.
“Your mommy seems very happy with her new boyfriend,” Auntie Brigitte said as she drew one side of my diapers up and pinned it to the other corner at my hips, “I think this is date number three.”
My spirits sank as I imagined her having wild, passionate sex with some strange man while I was confined to my nursery.
“Don’t look so grumpy, Jimmy,” she chided me as she drew up the other side and pinned it in place, “You should be happy for her that she’s found a man that can finally satisfy her–we both know you were never going to be able to do that.”
My eyes moistened with tears and I looked away, too ashamed to look my pretty babysitter in the face.
Taking a pair of shiny white nursery print waterproof panties, she shook them out with a flourish as she held them up before me.
“What do you think, Jimmy? Do you think these will look fashionable with your Disney Princess top?”
I squirmed with embarrassment as she smiled down on me in anticipation.
“Or would you prefer these cute pink panties with the lace?” she asked as she briefly picked up a polka dot pair of vinyl panties with white lace around the legs and waist.
“Personally, I like the white nursery print so I think that’s just what we’ll dress you in tonight,” she told me without waiting for an answer, “And anyway, it’s not like you’ll be showing off for anyone tonight in your crib. These plastic panties are good because they have nice snug elastic around the legs and waist –that’s an important feature for bedwetting sissies like you.”
Gathering them together in her hands, she began snaking them up my skinny, hairless legs. With some effort, she worked them around the considerable bulk of my diapers, ensuring that none of the soft cloth was exposed outside the elasticized seams.
“There you are, Babykins,” she said brightly, “All safe and secure now in your sissy panties. That should keep your crib dry.”
I whimpered and fidgeted, fussily nursing my milk as she made a few adjustments and checked around my waist. I hated wearing diapers and plastic pants but like everything else in this house–I had absolutely no say in the matter.
After briefly powdering between my legs, she patted the thick, shiny smooth face of my crotch with satisfaction.
“All ready for beddie-bye!” she announced, “Come on–hurry up and finish your bottle, it’s time to brush your teeth and then it’s into your crib for the night.”
I gulped the last of the tepid milk and I could already feel the drowsiness beginning to wash over me. Soon, I reflected miserably, I would be asleep in my crib, helplessly wetting my diapers while my wife was being ravished by some other man.
Awkwardly, I stood up and waddled toward the door, my bulky diaper preventing me from completely putting my legs together. Auntie Brigitte followed me out, slapping the thick seat of my diapers as a way of hurrying me to my task before going to meet Denise in the bedroom.
Dutifully, I did my business, wishing I could make use of the toilet like an adult before returning to the nursery. But I was only allowed to brush my teeth and I knew Auntie Brigitte would be impatiently waiting for me when I finished. I knew from experience that pulling my diapers down or fiddling with them in any way was grounds for a spanking so it wasn’t worth the risk.
A few minutes later, I waddled back to the nursery to see her talking with her boyfriend on the phone.
“Hey–gotta go,” she told him when she looked up to see me in the doorway, “But I’ll see you soon, I’ve just got to tuck the baby in.”
I also hated having to go to bed so early when everyone else’s evenings were just beginning.
“Can’t I stay up a little longer?” I begged her.
“Sorry Sissy–Mommy’s orders. You’re to be in your crib no later than 7:30,” she said as she glanced down at her watch, “Looks like we’re about 20 minutes early tonight but that’ll be just fine.”
“But–” I pouted crankily, “It’s not even bedtime yet.”
I stamped my feet in protest at her apparent indifference.
Auntie Brigitte scooped up the big pink rubber pacifier on the dresser and brought it over, pushing it against my lips.
“Open up for your paci, baby,” she said in a sing-song voice, ignoring my point completely.
“Uh-uh,” I refused petulantly, angrily pursing my lips together.
“Now Jimmy, you can either go to bed with–or without–a hot, stinging bottom. What’s it going to be?” she said in a firm, demanding voice.
Balling my fists together in frustration, I hesitated, but only briefly. Auntie Brigitte had no qualms about putting me over her lap to teach me a lesson as I’d already learned the hard way previously. Acknowledging her superiority, I obediently opened my lips and she pushed the thick rubber nipple into my mouth, ended the discussion once and for all. My cheeks reddened with humiliation at being defeated by this young hottie but I let her remove my Mary Janes before guiding me to the open side of the crib. She pulled back the soft pink coverlet and as I crawled in, I heard the waterproof vinyl mattress cover crinkle audibly beneath my weight, a sound all too familiar to a bedwetter. She pulled up the blankets and handed my teddy bear to me, tucking it in under my arm.
“That’s a good baby,” she said, once more in her pleasant mood. Reaching down, she kissed me on the cheek briefly and I inhaled her wonderful perfume. This one fleeting kiss was as close I got to having any kind of sex and I savored the instant, wishing somehow to make it linger.
But Auntie Brigitte was already closing the side of the crib, latching it in place before she turned and made for the door.
“Nighty-nite, Jimmy,” she said as she gently closed the door behind her.
After the door closed, the lights went out and the nursery became dark, save for the dim light put out by my Dumbo nightlight on the far wall. Denise had designed it that way so that the lighting could only be controlled from outside of the nursery. The door was also only lockable from the outside and I heard Auntie Brigitte gently turning the knob to make sure I was secure for the night. It would be another twelve hours before someone came in to check on me and by then, my diapers would be thoroughly and completely soaked.
In my utter frustration, I was tempted to spit out the pacifier and let loose with a string of colorful curse words but even with that, I knew better. A baby monitor stood on the dresser top, a permanent way for Denise or Auntie Brigitte to listen in on my nursery activities when I wasn’t being supervised. Among my other restrictions, I was forbidden to swear and it wasn’t worth a spanking and mouthsoaping just for a few words said in haste.
Except for the crinkling and rustling of my plastic panties and the mattress cover, the
room was quiet, and I tried to listen to see what was going on in the rest of the house. Denise was saying something to Auntie Brigitte; I heard the two of them giggle at something, and before long, I heard her heels clicking followed by the front door closing. A moment later, I heard the sound of her Lexus pulling out of the driveway and fading away down the street.
Without realizing it, I suddenly felt a slight warm wetness seeping between my legs and a trickle of pee flowing against my skin. With a panicked gulp and a cry of despair, I managed to shut off the flow but the damage was already done. Now I’d have to try and go to sleep with a distracting wet spot in my diaper.
It was going to be a very long night.
Last week, my mom took me up to my auntie Brigitte’s home for Thanksgiving gathering. We got there and gave aunt Brigitte a hug, she was wearing a red sexy dress that made her butt look amazing.
After dinner my cousin Jack and I went down to the basement to play ping pong. We started getting bored with that and decided to start wrestling. It was so funny, we were jumping off couches onto eat other. Jack picked me up and slammed me on the couch. I got up and ran away but he chased me, I stopped and flipped him over my shoulder and he landed on the coffee table and broke through it.
We stopped in silence and didn’t know what to do. Before we could do anything we heard someone coming down the stairs. It was my aunt.
She asked sternly: “What did you do?”
She grabbed Jack by the ear picked him up and said “I just bought this coffee table a month ago.”
Jack replied: “I know mom im sorry it wasnt my fault.”
She said “Oh really then who was it?”
Jack said “It was Charlie he flipped me into it.”
Aunt Brigitte looked at me very angry and asked me if it was true.
I said “Yes aunt Brigitte, I am sorry, we were wrestling and things got crazy”
Aunt Brigitte replied: “WRESTLING?! Jack you know there is no wrestling in this house. That’s it. Both of you upstairs now.”
We went upstairs and were lead by my aunt to my mother. My aunt told my mom what happened and my mom went to the basement and looked at the coffee table. She came back up and said” Brigitte,, you can punish him how ever you want, and Charlie I hope that your aunt spanks you hard, cause if it wasn’t Thanksgiving and I wasn’t in such a good mood, you would be getting a second spanking when we get home.”
Before i could say anything my aunt told her “Kristine, I would like you to join this spanking”. My mom was honored and accepted the invitation. My Aunt said “follow me everyone.” We followed her outside and I knew we were in for that chair spanking bench.
Just before we got into the shed, auntie Brigitte told my mom “I have a new bench to show you”
We got in the wood shed and my Aunt made us strip completely naked. Then she made Jack go under the chair and into position. Jack was naked tied upside down on a chair basically.
Jack’s naked bottom sat high on the edge of the chair. His balls and penis tucked on the underside of his thighs which meant they were visible in his position since he was upside down. Aunt Brigitte pulled a leather strap of the wall which was probably .5 inches thick, about 20 inches long and was cut into 3 long strands. The handle was wooden and the leather itself was very thick.
Aunt Brigitte told me to turn around so i couldn’t see the pain Jack was getting. I stood in the corner facing away as I heard loud cracks and cries from Jack. I felt bad for him but knew I was in for it. His spanking felt like it went on forever. Finally my aunt untied him and told me to come over.
I laid on the pillow under the chair. I put my legs up on the seat and felt my knees get tied to the back frame. Then my arms were tied under the chair. The chair was on an elevated platform that was at perfect position for bring down licks. My bare bottom, penis and balls were all in the air. My aunt then gave me the first lick
I couldn’t see it coming and I was in such a easy position for a lick that it hurts me really bad.
Crack CRACKK Crack
One stroke hit my penis which made me jump
Crackk Crack crackkk
I yelled and cried, another hit my balls which made me scream very loud
CRAck Crack crack CRACKK
Each stroke hurt more and more, I knew my bottom was burning red
Crack Crack CRACKK
Aunt Brigitte gave me about 20 strokes which was 20 less than what Jack got.
but then she handed the strap to my mom and said “Would you like to add your touch?”
My mom rubbed my bottom as I jumped from the pain of her touching it. She said “His bottom is perfectly done” I was glad to hear that and thought my punishment was over. Then my mom said “but lets add some red to his thighs.” Then my mom laid the strap on my thighs, got into a good position and started striking my thighs with the leather strap.
Crackk Crackk Crackk
Thigh spankings hurt a lot
Crack CRACk CRAck
I cried loud
The leather bounced off my thighs and sit spot
My mom turned my thighs as red as my bottom.
She then undid me and told me to put my clothes on. aunt Brigitte said “Next time I spend 300 dollars on a coffee table, I expect it to stay perfect or you will be held accountable” We both sniffled and walked back into auntie Brigitte’s house and tried to enjoy the rest of the day. I still cant sit today from that strapping.
“What did you say there Tony??????????? ………… Repeat that if you dare!!!!!!” A fuming Auntie B stood right in front of Tony. He looked at her, made a big judgmental mistake about the situation and repeated: “Wow, are you getting bitchier lately Auntie B?” Hardly had he spoken those words or she slapped him in his face which left him a stinging red spot. “Ouch, crazy woman. Are you nuts?” Tony said angrily while rubbing his cheek.
“Calling me nuts? Calling me a crazy woman??? First insulting me because of my attitude and now calling me names as well? How dare you speak to me that way bratboy? Even though your in your forties, still haven’t learned to show any respect at all for the opposite sex, do you?” Auntie B was a nice built woman, who was in her prime. She always dressed modern but casual, and three times a day she passed Tony’s room while collecting reports from the reproduction room. Most times Tony said timidly hi to her, while she waved cheerfully to him or looked playfully stern. Until now that was…… Auntie B, raged with anger by his behavior, made her decision. She pushed Tony back into his room, followed him closely and carefully shut the door behind them. Then she said sternly: “I think it’s time for a little discussion, don’t you agree young man?” Tony started blushing, knowing that this was the moment he longed for but at the same time was afraid for. While he sheepishly looked down, he remembered exactly when he had heard her use that sentence before.
Three months ago he had a received a call from Marc, a colleague, who complained about a problem of logging on at the server. Tony had checked everything on the server, but couldn’t find anything strange. In the end he decided to check out the computer of Marc in the hope to discover there something. The door was closed, but being his usual self, Tony rushed in without knocking the door. There he saw Auntie B in the middle of the room sitting in an armless chair with Marc draped over her knee. Tony was completely astonished and stammered “Ehh.. I just wanted to check the client-software on your computer Marc” “Marc doesn’t have time at the moment as you can see” Auntie B said sharply. “We are having a little discussion right now! And didn’t you learn to knock before entering?” Auntie B ended her lecture with a stern: “Close the door on your way out, you rascal and quickly before I spank you as well!!”. After that, she payed her full attention to the jeans of a pleading Marc. Totally flabbergasted and completely flustered Tony walked out of the room and closed the door at the exact time Auntie B ’s hand with an echoing smack contacted Marc’s bottom.
Marc had left the company a few weeks after the incident and both Tony and Auntie B hadn’t spoken a word about it to each other. Since that day though, Tony had dreamed about Auntie B, strong lectures, lots of spankings, and those lovely knees to lay over. But how to get in that situation…. he had no idea, or better said, no courage. Auntie B also had since her little discussion with Marc lots of ideas about Tony, and especially about that naughty bottom of his deserving her special attention. She thought of him bawling over her knee, while she would paint his buttock a nice mix of scarlet red and purple with her hand or leather paddle. Mmmmmmm, when she walked by and saw him greeting her clumsily, she secretly hoped to find a motive to put him over her lap.
That moment had arrived now. In deep thoughts, she had passed his room on the way to the repro and back and had forgotten to greet. Tony was annoyed big time and had tried to catch her attention with this crude remark. That worked, she was very upset now, and determined to teach him a lesson. Carefully Auntie B rolled up her sleeves and snapped to him: “You still haven’t realized what I do with naughty brats, have you? But my little rascal, you will suffer soon the consequences. Because of this insult you will go over my knee and get the spanking of your life!! And on your bare bottom!!” Then I am going to play with your prostate before I bend you over and give you a taste of my strapon. When we are finished, you are getting a golden shower from me and I have a lot of shower to give. We’ll swap spit but not the way you like it. If you are lucky, I’ll straddle your face afterwards and play with your nipples as you act as my toilet paper. I haven’t decided whether to give you a release or not. What I can promise is that I will stroke your cock through the entire punishment and make you beg for an orgasm.
She took the armless-chair and put it in the middle of the room. Then she walked resolute to Tony, took him by his ear and guided him to the chair. She sat down, hiked up quickly her skirt and unbuttoned Tony’s trousers. Then she pulled him in one swift movement over her left knee and pinned him down by putting her right leg over his legs. Without words she peeled the undies from his bottom and without further adue she started to spank those naughty buttocks hard with her hand.
Tony, though having dreamed of this little scene, slowly felt the heat on his bottom build. Stoic he tried to bear his punishment, but her skillful hands got after a short period some painful moans out of him. Auntie B smiled, hearing this, and got out of her leather paddle, took it from the ground, and started now really to put an fire on Tony’s ass.
“You naughty little brat, after this spanking you won’t sit for a week…. Smack slap spank, from the left cheek to the right, smack, spank slap, let’s give that bottom it’s well deserved scarlet red color!!”
Tony started crying “ooooooooohh I.. I am so sorry Auntie B, I was only joking.. r.. really, p… pleaaase, I will behave!!!” “Yes, you certainly will, my naughty boy”, Auntie B said while painting every inch of white skin on Tony’s buttock’s red, “Because if you don’t, from now on we will have just as much little discussions until you do!”
Although Tony pleaded in tears to be good, Auntie B was deaf for his pleas and didn’t stop spanking him until she decided he had enough. When that was the case he laid sobbing over her leg and softly whispered “Thank you for correcting my behavior Auntie B ” She softly caressed his scarlet bottom and said, “you’re welcome Tony, be prepared for lots of little discussions of mine in which you can admire the carpet frequently from now on!! We are not finished yet.”
We still have more S’s to go through.” She leaned over to pick up something and heard the snap of a leather glove, followed by her strong hand separate his ass cheeks. After a cool liquid was applied, her fingers were deep inside him probing his prostate. He tensed up only to feel a hard spank on his bottom. “Sit Still or it will be a lot worse. We have a long way to go.”
“Y.. yes Auntie B, I will “, Tony sobbed.
Here is a story that my slave Tony wrote for this journal
Auntie B had just finished a very long over the knee spanking. My cock was hard as a rock from all the tease and denial Auntie B likes to do during my punishments. She had a smile on her face when she looked down at my member. Of course, the penalty for not staying hard is an automatic 100 extra strokes with whatever she is using at the time.
“Get up and stand in that corner hands on head” she commanded and still crying freely I rushed to comply. As I stood displaying my well spanked bottom and trying to control my tears, I heard the punishment drawer open and the leather paddle was placed on its hook. I trembled visibly as I heard Auntie B withdraw something else from the drawer.
“Turn around” Auntie B ordered. She was holding the lubricant in her hand. “You’ve earned a release before bedtime but you will earn it, or there will be more punishment. Right now, I need to use the ladies room and make sure my panties are nice and soiled when I am finished. When I return, those moist panties will be wrapped around your face so you smell my scent during your orgasm. I want to see you kneeling in front of the spanking chair as I enter the room.” SLAP! “Now face the wall again please. Will you never learn that in the bathroom every time I find the toilet seat up, I will spank you again after dinner as another reminder? It’s a simple rule seat up, pants down.”
When she returned, she came and stood in front of me with a satisfied smile on her face. “I just took a nice long pee and wiped myself thoroughly with my panties. Don’t worry though, I made sure all of my scent is all around my panties. Here, see for yourself.” With that, she removed her panties and wrapped them around my face, making sure the most pungent part was right in front of my nose. Then she sat down in front of me and leaned forward. She placed her hand on my cock and began to stroke it a little. When I was ready to explode, she pulled away.
“Put some lubricant on your cock and start stroking your cock.” She began to rub and squeeze me nipples. HARD. “Here is how this is going to work. I am going to continue to work over your nipples. You will have 30 seconds to cum when I tell you to get started. If you don’t cum in 30 seconds, you go back over my knee for the same amount of time and I will get in as many hand spanks as time allows. After that, the seconds go up 15 seconds at a time. In other words, if you don’t cum in the first 30 seconds you will have 45 seconds in the next segment or its 45 seconds over my knee and so on. How bad do you want to cum pet? You better get it done quickly. Remember, you have another spanking coming after dinner before you go to bed: Her smile went right through me. “Get started!”
The big day had finally arrived. I was about to meet Auntie B. I hadn’t slept in three nights in anticipation. Was the build up too much? Would the wait really have been worth it? I couldn’t get her pictures out of my mind as I walked up to the door. When I heard the locks tumble and the door knob turn, all my questions we answered in the next five seconds. There stood Auntie B. As intimidating as I thought she would be, but much prettier than I ever could have wished for. She had written me through the weeks with some fantasy choices. I thought they were meant to be just a fantasy.
Choice number one. I will take you over my knee and spank you very soundly for 35 minutes with my hand, or you can have a 15 minute spanking with the instrument of my choice and you will count. I knew that either meant the hairbrush or the strap and I hate counting out loud. It breaks my concentration. This was an impossible choice. She told me her hand is like iron but her instruments can be very painful as well. Then she added another twist as she looked me right in the eye. If you choose my hand and I feel you are wiggling too much or getting out of position, I have the option of getting the round leather paddle, locking you over my knee and adding another ten minutes. I knew I was making a mistake when I chose her hand and saw her face light up with a huge smile.
Choice number two. I will squeeze, bite or pinch your nipples for thirty minutes or you can choose to wear clamps during your entire punishment. If you choose the first option, that doesn’t necessarily mean I will do the entire thirty minutes at once. I might choose to bind you to a table and just do ten minutes while I tease you. Then I might decide to do five minutes four more times. Auntie B was loving every minute of this. I told her I absolutely hate nipple clamps. I can’t concentrate when those damn things are on. I knew it was a mistake but had little choice when I chose not to have the clamps. Good boy, she affirmed.
Choice number Three. When I am through spanking you, it’s time for a little humility. I can both keep you over my knee and violate your prostate for as long as I want, or I can take a butt plug covered in stinging ointment and be much rougher for 10-15 minutes. If you choose the first option, I have the choice of putting a butt plug inside you before dinner tonight and making you use it all through dinner. I didn’t know what to say. I wanted this to be over and not worry about it all day but that ointment can be very harsh as well. Plus, what if she inserts more than one finger? BTW, if you select the first option, we will come back here after dinner, I will remove the plug and you will be spanked by my hand harder than I have ever spanked you before. I was beside myself. Auntie B had her hands on her hips as she tapped her foot. Well!! I guess I’ll take the first option, I softly said as I was staring at the ground. She walked toward me, grabbed my chin and put her face right in front of mine. That was your first mistake!! Now open your mouth. She gave me another cup of coffee.
Choice number four.The choices wouldn’t be complete without my fucking your little ass. Here I have two strapons. I will you bend over the bed or fuck you doggie style with the smaller dildo until I am tired, or I can use the larger one and fuck you very hard for 10 minutes. I was spent and didn’t know what to say. I figured by this time she might be tired so I chose the first option. This was a no win choice. I just hoped that by then she remembers it is my birthday.
“Hello Tony. Please come in.” Her voice went right through me. I gingerly stepped in to the room as she came closer to me. SLAP! There it was a slap right across the face. Not too hard but just enough to get my attention. As she moved closer, she grabbed my chin and put her face close to mine. “You have been having a lot of fun lately haven’t you? You have been looking at my pictures choices and masturbating too” “Yes, I mumbled.” “Well honey, the party is just beginning. Open your mouth and put your head back.” As she spit in my mouth, she said, “that’s the only spit swapping you will be getting for awhile.” With that, she grabbed me by the ear and led me into the room where there was a small foot stool. As we moved closer, in one fell swoop, she put her foot on the stool, pulled me over her thigh, and held me tightly by my hip. She then began spanking me very hard over my pants.
As I stared down the back of her leg, I couldn’t believe how strong she was. My face was sore but all I could think about was the spanking I was getting. Are you kidding me? I’ll never be able to take this on my bare bottom. She continued to spank and scold me. Just when I thought I couldn’t take anymore, she stopped and stood me up. She had my full attention and she knew it.
She grabbed me by my hand and walked me over to a chair that was in the middle of the room. As I stood in front of her, she began to unbutton my shirt. After she had taken it off she moved her head t my chest. Her hair smelled wonderful. She began to pinch my nipples and then I felt a great deal of pain. I almost buckled. She smiled and then sat in down front of me. . “I have had a long day and I am hungry Tony, so here is what we are going to do. I am going to put you over my knee and give you a very hard spanking. THEN, we are going to dinner so I can watch you try and sit comfortably while eating. When we are done, we are going to come back here. This way, I can take as much time as I want giving you the discipline and training you deserve as we go through all the choices that I sent you. Before each scenario, you will go back over my knee so I can make sure your ass is sore through the entire session. Any questions?” I didn’t know what to say. “No.” was all I could think of. “Good. Let’s get started.” As my pants fell to the floor and my underpants followed. Then she gave my manhood a very hard squeeze. It’s funny how things always seem more pleasant in a story, than when they actually happen. It certainly didn’t feel funny when she stopped squeezing to pull me across her knee for the first of many bare bottom spankings. True to her word though, she did give me a warmup with the proper scolding and concentrated on my cheeks. I couldn’t help but think how such soft hands could hurt so much. “Whew, I’m hungry. Let’s go eat.” she said.
The restaurant played out just as she thought it would. She was beaming with confidence and was quite the lady. She was very bright and wonderful to talk to. I couldn’t take my eyes off her face. No one else in the room knew that I was completely hers. My bottom was sore and kept reminding me that the person across from me was going to be giving me the punishment of a lifetime in about another hour and I didn’t care. Although I tried not to show it, I was nervous and a little afraid. At the same time though, I was at peace with this woman. It was like no one else could do me any harm as long as I was with her. I was hers to punish and no one else could.
When dinner was over, we did exactly what she said we would. We went back to her place and covered every choice. Plus, my bottom was spanked between every event.
We were both very spent by then and I went and took a shower. When I came back out, she had a sinister smile on her face. “Tony, I have one more choice of my own.” “What’s that?” I inquired. “Would you like to spend the night with me? I’m not talking about sex, even though I might have you please me at some point. What I am talking about is spending the night together while spooning and cuddling.” “That’s an easy choice.” I said. “Well that’s the tricky part.” She came over and held me to her chest. “There may be a bedtime or morning spanking in it as well.” I knew I couldn’t take much more spanking but as I had her arms around me, I knew which choice I wanted. After the punishment I received, the thought of being in her arms for a night was too much to bear. I would do anything for her. I felt sense of security and protection with her that I haven’t felt in a long time. “Yes. Please Sage. I want you to hold me all night.” “Ok Tony, let’s go by the hotel and get your things.” She patted me bottom as we broke apart.
The rest is up to your imagination.
Longing and Deception
Jo, was spending a rare weekend alone with his Aunt Nancy. His uncle and cousins had just left for bible camp. Jo finally had the chance to try and experience Nancy’s treatments that his cousins had told him stories about and he so much wanted done to him. When Nancy sat down on his bed to tuck him in for the night wearing only a silk nightgown, he complained that he had a tummy ache. She acted concerned. She slipped her fingers down under the waistband of his pajamas and while innocently brushing against his rapidly swelling penis she pressed around on his abdomen.
While giving him a big bosomy hug she told him she knew exactly what she needed to do to make him feel better. However, they would have to wait until she returned from her hospital shift the following afternoon. While he felt her hard nipple press against his cheek thru the sheer silk fabric, his anus twitched in anticipation of the unknown. Once the door shut, Jo pulled out his flashlight and ogled thru the big envelope of porno pages his cousins had loaned him.
The following day, at the hospital, aunt Nancy’s supervisor informed her that she would have to stay for the night shift. Not wanting to leave Jo alone, she called Auntie Brigitte, who introduced herself at church last week as having just arrived from France to serve at the local Catholic girls boarding school as Headmistress and School Nurse.
Brigitte immediately offered to watch Jo overnight at her apartment. Nancy thanked her profusely, but added he had a tummy ache and she was planning to give him his first enemas. Brigitte explained she would evaluate his condition and the academy clinic was well equipped in that area of treatment… (and she was secretly eager for the chance to work with some male anatomy for a change…).
Nancy told Brigitte that if Jo gave her any trouble, she should sternly discipline him. She then proceeded to call Jo from her wall phone and instructed him to pack a small overnight bag and walk the 2 blocks to her new friend’s on-campus residence and arrive at 6pm sharp.
Jo was soooo disappointed!! Oh well, he could just watch the Seahawks game. He threw the big envelope into his overnight bag for some later nocturnal reading. His treatment from aunt Nancy would just have to wait another day.
When Brigitte heard the doorbell ring, Tom offered a disinterested hello, dropped his bag in the hall and immediately went over to her TV and turned on the game.
She moved his bag to the clinic guestroom where an envelope fell out. Her curiosity tempted her to take a peek.
OH MY GOSH!! Another boy just waiting to poke one of my girls on a first date!
Both embarrassed and angry, she marched out to confront Jo:
”Tell me what is in this envelope, young man…”.
Without turning his head from the screen, he told her not to interrupt him until halftime. Now at the end of her patience, she slammed off the TV, grabbed a handful of his hair and struggled to drop his pants. He soon found himself stretched across her lap with his penis trapped between her strong thighs. This wasn’t her first rodeo
”I will ask you again, Tell me what is in this envelope, young man?…”.
When he answered that he had never seen it before, the spanking began and continued for several rounds of repeated questioning and increasing intensity until he could take any more and confessed to having naughty pictures in that envelope.
She stood him up and looked at him straight in the eyes while squeezing his cheeks. She explained to him that he had a choice:
she could either show the envelope to Aunt Nancy tomorrow, or he could let Auntie Brigitte discipline him right now and Nancy would never have to know.
Not wanting to get his cousins in big trouble, Jo agreed to let what happens in Brigitte’s apartment stays in Brigitte’s apartment. How bad could that be, anyway?
Seduction and Discipline
Knowing she couldn’t ave sex with him, she was still relishing the opportunity to torment Jo with her seductive touch and posturing that would arouse his emerging sexuality interspersed by humiliating and uncomfortable medical procedures in a revolving cycle of intensely confusing erotic sensations.
She was well experienced in leveraging the power of the prostate and ready to lead him past the societal humiliation and onto accepting anal bliss…. But first she had to soften up his male machismo for him to be ready to make that surrender.
Sensing his uncontrollable curiosity in the mysteries of a woman’s body she seductively removed her dress.
Picking up her cane and tapping it on her palm, she asked Tom if he liked what he saw; auntie Brigitte now standing defiantly in front of him wearing only a silk bra, panties, garter belt and stockings.
Arranging a stack of pillows on the bed, she grabbed his arm and positioned him spreadeagled over the hump widely spreading his legs. He lets out a yelp as he felt a stinging soap covered butt plug being relentlessly pressured up his anus and lodged into his rectum.
“Don’t you dare let that come out until I decide to remove it”
Picking up the envelope, Brigitte sat down next to him and pulled out a page and showed the first image to him.
And so began his discipline, as she retrieved her favorite cane, paddle and strap and began delivering some strokes before taking a break to show him the next page’s revelations and starting the next round of gradually intensifying strokes. This continued in several cycles before ending with a crescendo of stinging rapid fire impacts that left him whimpering in a fetal position. He was now ready to move on.
Changing her demeanor to mothering care, Brigitte cuddled Jo in her arms, smothering him tight against her chest and asks if he had learned his lesson.
Like a needy dependent child, his bottom stinging with pain, he clamped his arms around her and quietly thanked her. Asking if he could now go back and watch the game. She said NO and explained that they still had more important business to attend to. She told him that aunt Nancy had voiced her concerns about his tummy ache.
Jo answered that after aunt Nancy pressed on his belly she told him she knew what would make him feel better. He expected her to take care of that tomorrow.
“No need to worry about that tonight, Auntie Brigitte! “
To which, Brigitte retorted that she is the academy nurse and Rosie had requested that she evaluate his condition. …..She wouldn’t pass up this opportunity for the world…..
With an ominous smile, Brigitte said:
“Let’s check out Tummy tummy…”
and proceeded to straddle Jo’s face backwards, smothering him with her butt and introducing him to the overwhelming scent of a woman through her silk panties as well as holding him down while sensuously pressing around his abdomen and meandering her hands down to tease his genitals, lightly stroking him, cradling his testicles and pulling on his emerging recent growth of pubic hair.
Returning attention back to his abdomen she mused:
“I can understand why Nancy was concerned”
She got off him as he found himself gasping for air and ordered him up onto his hands and knees, face down on the bed. Snapping on a rubber glove in front of his face, she moved back out of sight and he felt the first-time delicate teasing touch on his virgin anal opening and perineum.
HOW HUMILIATING! He tried to get up but she pushed his head back down
“We aren’t done yet, young man…..”
She firmly grabbed his testicles with one hand and while pulling back for leverage, she slided a finger through his pencil tight opening and deep into his rectum. Working over his prostate for some time and adding fingers, he heard her disturbing results
“this is not good, not good at all…another case of teenage constipation…..”
Pulling off the soiled glove she had him sit next to her for a little talk. Hugging him affectionately she explained
“Jo, I need to leave for a few minutes to prepare some medicine. It will be easier to take if you spend the time trying to relax”
and she disappeared into the bathroom. He figured he knew what would be next. A spoonful of castor oil and a plate of prunes to be eaten during the second half instead of the potato chips he brought.
He couldn’t understand what was taking her so long and started playing with his erection curious about how the anal stimulation had powerfully aroused him. He hears water running…and running….and running and still couldn’t understand what was going on……until……his attention became riveted onto Auntie Brigitte as the bathroom door opened and she emerged wearing only a garter belt stockings and heels.
The elusive mystery of a woman’s triangle was finally revealed accented by a thick patch of curly black pubic hair. But within a blink of his eyes, his attention moved to what she was struggling to carry… A huge bloated wet dripping red hospital enema bag with a flared nozzle that will surely never fit!!
Ordering him to stand, she pressed the warmed wet rubber up against his tummy and genitals and muttered:
“just the right amount”.
Which he noticed, matched the “one gallon” line marked on the bag.
OH MY GOD, NO!!!
She rolled an IV stand next to the bed and was barely able to lift the swaying heavy apparatus onto the hook. Some medicine! Auntie Brigitte sternly ordered him to assume the humiliating position of lying on his back with legs spread wide and drawn up on the edge of the bed while she towered over him testing the flow and temperature on her wrist and dripping down onto his bare skin.
Positioned between his legs leaning over him with her breasts erotically swaying, she lubed up the nozzle, ordered him to take a deep breath and separated his buttocks. She drove the flared form up through his sphincter to fulfill it’s purpose of not falling out and keeping the water in. With a tone of motherly empathy she explained to him this would unfortunately be an uncomfortable but necessary experience while secretly looking forward to watching him squirm and struggle as she controlled the flow of the large enema draining from the bag and meandering relentlessly up the path of his expanding colon .
Sitting down next to him she snapped open the hose clamp and he flinched with the first new sensation of the warm enema entering him and the ominous hint of the building pressure to follow. She grabbed her bottle of baby oil and explained how she would be massaging his abdomen to help distribute the volume as she traced with her fingertips the hardening taught skin while the water moved up the path of his expanding intestine.
Having witnessed many female orgasms from similar treatments of her students, she was curious to watch how erotically arousing the internal warmth and pressure would be for Jo and so, she enjoyed gently caressing his genitals as the water flowed past his prostate.
But unlike women, there becomes a point for a male where the erotic pressure moves the attention from sexual pleasure to surviving the deep discomfort of the remaining bag and as a result.. Old Glory falls to half mast…..
She felt him holding her hand and eventually reaching out to bury his face into her breasts for reassurance and comforting as the bag (now all too slowly) flattened. He winced and panted. Taking pleasure in her opportunity to offer mothering support, Auntie Brigitte whispered softly to him and coached him to take deep breaths and try to relax as she started to stop the flow. She sensed his condition and waited for the cramps to pass and his colon to gradually expand before adding more flow. He struggled with all his bravery to gain the approving touch and motherly gaze from Auntie Brigitte for his attempt to empty the contents of her treatment. Together they watched the bag go flat and the last column of water move down the tube and she clamped it shut for the last time. A motherly hug follows and she helped the bloated boy struggle off the bed and mercifully walk to the toilet for a loooong and welcome enema release.
Returning to the bedroom he asked:
“Now can I watch the game, Auntie Brigitte?”
Totally confused, he was surprised to see her demeanor change back to the earlier punishment. “Now that you are well cleaned out, Jo, I think it is high time for you to experience what these young girls experience when you poke them”.
She revealed a collection of dildo probes from small to terrifyingly huge. A series of erotically deep insertions of graduated size left him glassy eyed staring at the ceiling and humiliated by the arousing and pleasurable effect it was having on him. She buckled up her most challenging strap-on dildo which she affectionately called her “sissy mouth stuffer” and after the thrill of gagging him, repeatedly drove it deep up his rectum over and over while restraining him with a sensuous hold on his genitals.
Pulling out of his now well relaxed orifice, she knew he was ready for the ultimate surrender
“I need to verify the enema accomplished the intended results”
and slowly worked her gloved fist up against his willing sphincter. With some cooperative effort, she felt her knuckles pass through the most difficult place as he sucked her fist up into his rectum. Overcome with emotion and the ultimate arousal, he collapsed onto the bed as she blanketed her warm form over his totally spent body. So much time had passed, the football game has ended
The next morning when he ran out to aunt Nancy’s waiting ride, she asked him how the evening went..
Oh, it was a good evening,
with a reflective smile staring out the window back to a waving Auntie Brigitte…..
“the Seahawks beat the Redskins……”
-with a wink to auntie Brigitte