I have previously written about the spankings my three sisters and I received from our parents while growing up, and about a spanking I received from a friend’s parents. I think the idea of receiving a spanking from someone other than my parents has always fascinated me, and I imagine this is true for many of us.
Perhaps one of the most interesting and controversial non-parental spankers is the babysitter, partially due to the presumed younger age of such a figure and the resulting smaller age gap. Until my older sister was almost 15, our parents insisted on getting a babysitter for any significant absence on their part.
My older sister could be a bit irresponsible, but they were more concerned about the challenge of handling me and my two younger sisters than her lack of ability. Our sitters came from a mix of family friends and a nearby college, with the latter recommended by one of the college chaplains, who was friends with our parents. Yes, they had permission to spank, but they all approached the task differently.
This incident occurred one summer when I was 12 and my older sister left for camp earlier than me, leaving me with my younger sisters Leah, seven and four-year-old Emily. Naturally, I considered myself far too old for a sitter, and I protested when Mom and Dad informed us that we would be left with a new sitter while they took a weekend vacation from dealing with us (though they put it in much kinder terms).
This was a new sitter, Grace, who they told us was a sophomore at the college, studying anthropology. She was from another region of the country, so when she arrived on Friday afternoon, I was taken aback by her accent.
I was also somewhat dumbfounded by her appearance. In retrospect, looking at her Facebook photographs from her college days, she was neither my ‘type’ nor the most stunning among her sorority sisters, but I was almost 13 and it really did not take much to make me fall completely in love.
Grace had long, straight dirty-blonde hair, average proportions and a kind, cute face. At around 20, she was on the taller side, while I had not yet hit my growth spurt. She had in tow a small pink suitcase that was a bit childish for her age, probably a relic of earlier years, and was wearing a light knit sweater and solid colour calf-length skirt. Oh, and a halo as far as I was concerned!
The afternoon started off quite delightfully, with all of us playing outside in the mud and fields. Grace simultaneously threw a lovely tea party for my sisters while challenging me, her knight errant, to complete various adventures and projects with her aid. She wasn’t afraid to get a bit dirty helping me gather kindling for a fire, and she treated me with the respect I imagined I was owed due to my impending manhood.
Well, all this idyllic fun ended in an instant when Leah, probably jealous of the momentary attention Grace was paying me, scooped up a nice fistful of runny mud, and threw it at our new babysitter. The dirt splattered all over Grace’s skirt and sweater, and her jaw dropped as she looked first at the damage and then at Leah.
In a moment, everything changed. Grace’s pleasant smile was gone, and her accommodating demeanour had given way to an almost military firmness. She politely asked me to escort my sisters inside and wait in the living room while she cleaned up.
Grace retreated to the guest bedroom, and I heard the muffled sound of her speaking on the phone, presumably with my parents. In around 20 minutes, she joined us back in the living room. The first thing my sister Leah noticed was the Jokari paddle in Grace’s hand.
But the first thing I noticed was that Grace had changed into a light flannel top and a pair of print leggings, presumably her pyjamas. I could not help but fixate on how the leggings traced her legs from her ankles to her hips, outlining both her bottom and (very noticeably) her pubic mound and labia, two features I could both neither name at that age nor avert my eyes from.
Grace instructed me and Emily to sit on the couch, which we instantly did. Turning to Leah, she informed her that in light of her violent and disrespectful actions, our parents had asked her to administer a ‘good whuppin’, as she put it in her drawl.
“They told me that they normally use a belt or strap for these things but where I’m from, I’m used to my daddy bruising my hiney with a paddle, so that’s what I’m gonna do for you. We have the same paddle at home that I got when I was a lil’ girl, so I won’t have any whinin’ or tryin’-a get out of this.”
With that, she put down the paddle on the big arm chair and firmly pulled Leah’s dress over her head, leaving her in a pair of dirty white panties printed with cartoon animals. Between the panties and her still-stained hands and feet, Leah looked more than a little grubby, even by my own lax standards. Grace murmured: “You are absolutely disgusting, little one! After this, there will be a bath.”
With that, Grace peeled the briefs off my sister’s bottom, discarding them with the rest of her clothes in a pile on the floor. She then led Leah by the wrist over to the armchair, bending her body over the seat so that my sister’s hips sat right on the edge. The angle forced her to arch her back, sticking her lily-white rear end up in the air and stretching out her grass-stained thighs.
Grace wasted no time in deliver the first smack with the paddle, and it seemed to me that she used a surprising level of force. The paddle covered most of Leah’s seven-year-old bum and left an immediate pink colouring. Grace raised the paddle for the next whack and continued to bring it down again and again squarely in Leah’s poor little bottom.
Naturally, this sent my little sister into an immediate flurry of real tears as between her sobs and cries she begged ‘Miss Grace’ to please stop spanking her. Needless to say, these pleas were ignored and Grace’s paddling reduced my little sister to utter submission in a minute.
Emily tried to hide her amusement at her older sister’s torment. Meanwhile, I sat with my eyes rapidly switching between Grace’s tightly wrapped posterior and my sister’s now cherry-red butt that framed a protruding pair of puffy lips. Not only was I enthralled by these sights, but I quickly realised how aroused I was, although my understanding of this was rather basic.
Furthermore, I realised that I had a strange desire to swap places with my sister – something which under normal circumstances I would do everything to avoid.
As Grace wrapped up the paddling, I began to involuntarily formulate a plan. In a moment, Grace had finished and briefly hugged Leah, who was now clutching a crimson behind with a mild bruise in the centre of each cheek. Leah then scrambled away, hopping from foot to foot while clutching and massaging her sore rear, giving all of us a delightful view. While I would normally have been preoccupied with this, my thoughts were elsewhere.
Smiling, Grace then instructed me to go set the table for dinner. This was my chance: I had resolved to refuse the first request image issued. In a dead-serious monotone, I look up at her and simply said, “No.” She giggled at first, assuming I was joking, and told me to go and set four places. I repeated myself, with a bit more emphasis.
“Now, Cal – stop being silly, I have asked you twice.” It was too late to reverse course – I was all in, and my heart was racing. “No, no, no!” I shouted, stamping my foot, probably releasing the pent-up anxiety over my mission.
“Cal! This is not like you. What’s gotten into you?” Grace demanded. Well, things declined from there. I began throwing a tantrum quite unbefitting my age, and after the afternoon’s events, she was having none of it.
Finally Grace picked up the paddle again. “Well, I have this out, and if you are going to behave like your sister, I might as well give you the same,” she said in a firm but patient voice. With that, she grabbed my wrist with one hand and stripped my shorts and underpants complete off with the other. My heart beat so fast I thought it would burst.
To my surprise, Grace didn’t lead me over to the chair. Instead, she tucked my head down between her legs, forcing me to bend over and shoving my butt up in the air in the perfect position for the paddle, which she immediately put to work on my bare bottom.
I had been correct: Grace paddled very hard. I was crying real tears in a matter of swats, in far too much pain to care any more about being almost a man. While my throbbing little friend had initially stood at full attention, pressed to my stomach, it quickly soften and jiggled around with the violent strikes of the paddle.
I am sure I pleaded for mercy and promised her lifelong servitude, but I have little memory of how long the spanking lasted or how it proceeded except for the searing pain. Then it was over, and she was hugging my tightly. Grace held my undies open for me to step back into, carefully pulling them up, although her care did not avert the pain of the rough cotton against my bruised bum.
Without further instruction I set the table, then returned to the couch as she cooked. Dinner was pleasant, and she made sure to cheerfully engage Leah and I as we sat rubbing the seats of our undies to ease our bruised bottoms. After she washed the dishes, she tucked in my sisters and read us all a story, allowing Leah to curl up in her lap.
After we both bid my sisters goodnight, she walked me to my room, where I began to get into my bed. I must have been less than eager or looked a bit off because, almost jokingly, she asked if I needed to be tucked in like my sisters.
I didn’t answer, but something about the face I gave her must have constituted a ‘yes’. Grace sat down towards the head of my bed, and eased my head into her lap. I had not been expecting this, but I immediately decided this was heaven. I was acutely conscious of the warmth, and although I had no idea what it was or what it meant, I smelled something unusual yet strangely enticing.
I pulled up the covers to hide the erection that ensued, and we remained like this for a few minutes. Eventually, Grace told me how she had enjoyed playing earlier in the day, and how she was sorry that she had to ‘whup’ my ‘bum-bum’.” She further remarked that she thought my change of behaviour was unexpected, but that being a pre-teen could be rough. She added that she had been the same way when she was my age, and that her mommy and daddy would ‘whup my bum till my panties caught fire’.
With that, she laid my head on my pillow, turned out the light and left. That night, I furiously rubbed myself as I thought of Grace spanking my sister, Grace spanking me, Grace’s parents spanking her, and even what lay under Grace’s leggings and panties. I was still unable to get any results from this masturbation – but that changed within a year.
I now realise that Grace probably suspected the motivation behind my strange behaviour. She sat for us a few more times before I was old enough to be responsible for my younger sisters.
Years later, Grace and I found ourselves living in the same small city while I worked a summer internship and she was in graduate school. We decided to get coffee and catch up, which led to some walks and museum visits over the following weeks, which led to some dinners and then some drinking.
I was still mesmerized with her as my childhood sitter, and to be honest, I think she was a combination of bored and kinky, because we started hooking up. It was purely a summer fling but we had some fun, including spanking each other. She married a fellow graduate student a few years ago, and by all accounts is enjoying motherhood.
Contributor: Cal