The Errant Schoolgirl

The Errant Schoolgirl — A Roleplay

For some reason I have been thinking of this lately, it was a roleplay that my play partner at the time and I had done a few years ago. We only played over the summer of 2004, but it is perhaps my favourite partnership that was founded upon spanking. Raven was an amazing person and a wonderful play partner and I remember her fondly.

During the weeks of conversation, this was something that we had both agreed upon that we would both like to try, and probably very much enjoy. Raven was going to be the bratty schoolgirl and I her Professor. We saved this for Saturday night and we also both agreed afterwards, this was the best play session that we have had to date.

After a fun filled day we had relaxed for a while and talked about our plan. Raven excused herself into her room while I changed in the living room. After traveling all I could really dress in was a black shirt and black pants that was the closest I could get to be a professor this time around. Raven on the other hand had a full wardrobe at her disposal.

So I waited patiently on the sofa with the TV on, until I was treated with the delight that was soon to come. After several minutes, Raven entered the room, not as one would expect though. For some strange reason, wearing the catholic schoolgirl outfit put her into toppy mode. She entered with an 18 inch ruler tucked under her arm like she was some kind of drill sergeant, pacing up and down making all kinds of threats towards me, was this Mistress Raven in her younger days, I thought to myself.

Before we began we both decided that we wanted a smoke. This allowed me to talk Raven down and out of her toppiness, which was quite the task as the outfit had provided her with some power. As we sat there we started a rehearsal role-play, it wasn’t planned, we went straight into it and I think it helped the ‘real’ scene once it started. The funniest part of the whole night happened during that time as well. As we bantered, Raven was sat sideways to me. Now one of the things we played with was her attire and how it was not regulation, it was an adult schoolgirl after all, I am sure that it was because of the short length of her skirt that this happened. Trying to focus my attention away from the upskirt shots I was getting, I tried to reprimand her on her huge platform shoes, only, it came out like this.. “And what is with these sh-sh-sh-sh-sh-shoes” I just couldn’t get the darn word out. Well that was it, the combination of the nerves and the stuttering comment and we were both toast, the pair of us began to laugh until our sides were hurting.

More cigarettes followed as we composed ourselves, and then we were ready to begin.

Miss Gallagher stood up and moved around the table. I began what was to be a long discussion. “So, Miss Gallagher, you find yourself in my office one more time. What are you here for this time young lady?”

“I don’t know” she replied, “You must like me or something”

“Well of course I like you Miss Gallagher, but that is not the reason that you are here today, is it?”

“How should I know”?

“There is a little matter of a poem that you wrote”

“I have no idea what you are talking about”

“You have no idea what I am talking about huh, I am talking about this young lady”

I then gave the young lady a printed copy of the poem. The poem was actually something Raven had written in response to one of my posts, so there was an air of truth to the scene. Undeterred however, Miss Gallagher played her part to a tee. We discussed the poem and I was met with replies such as “It’s not mine”, “I’ve never seen it before”, “I don’t know who’s it is” But I had a little trick up my sleeve, and now was the time to use it.

“So you say this is not yours do you young lady, well come with me” I sternly remarked.

In a huff, and with her arms still folded, Miss Gallagher followed me into the bedroom, even making a sassy comment about WHY we are going into the bedroom, such a little minx. As we entered the bedroom I turned and asked Miss Gallagher the screen name that she uses when online. Perhaps sensing trouble, she tried to look disinterested and blurted out Raven before focusing on the computer screen.

In preparation for the upcoming scene, while Raven was changing I had brought up the offending poem on the computer screen, MUCH to her surprise. “Well then Miss Gallagher, would you like to explain this to me?”

With her mouth open, the young lass read the offending poem and quickly scrambled to find an excuse. “That’s not mine, I didn’t write it,” She offered.

“You didn’t write it? Whose name does that say right there girl”?

“Doesn’t matter, I didn’t write it!! I was set up”

“You were set up?” I asked, intrigued “Set up by who”

“I don’t know, must’ve been one of my friends”

This answer shocked me, the look on my face must have said it all as I repeated what she had just said to me, but she continued.

“Yeah, one of them must have got my password”

“If one of your friends got your password then you are just as much to blame for letting them get it my girl”

“Well all I know is that I didn’t write it”

The patience of a saint was now being tested, taking Miss Gallagher by the wrist I lead her back to my ‘office’ with a stern “Come with me girl”. Upon entering the room I stood and looked up and down at the brat, her blouse tied in a knot and half undone, the skirt a minuscule size against her long legs, the high heeled shoes, arms folded and chewing gum. I started to reprimand her on her appearance, beginning with the open blouse. “What made you wear your blouse like this young lady, all unbuttoned and tied at the waist, look, I can plainly see your bra, well, what there is of it, it hardly would seem worth wearing one”

With a deep sigh and a flick of the head she replied “It’s HOT, besides, I like the fashion”

“We are not a catwalk young lady, now put those arms to your SIDE and stand up straight”

Miss Gallagher complied but not without a defeated shrug of the shoulders.

“And what is with this skirt, could it get much shorter?”

“I like it this way!”

“Miss Gallagher, we have many young men at this school, we can’t have you walking around like this, you only have to bend over slightly and they will be looking at your panties. We need these young men to be able to keep their concentration while they are studying”

“They do concentrate sir, they concentrate on me,” She said with a big grin.

“Well I am not going to let you parade around this school flashing your knickers to everyone”

“You never seem to mind… Sir”

“And just WHAT do you mean by that young lady?”

“I see you always checking me out, trying to find reasons to spank me, just so that you can get your hands on my butt”

“Miss Gallagher, the only interest I have is in your well being young lady, and if that means spanking you then I will do it”

“You perv!!”

“It has nothing to do with being a pervert missy. I care very much about ALL the girls in this school, in fact, you can ask them and they will ALL tell you that I have had to spank them from time to time”

“Yeah, that doesn’t surprise me at all” She said in a mocking tone “Like I said, you’re a pervert”

I approached the sassy girl, as she stood firm with a challenging look in her eyes, her willful determination was quite apparent. As I stared her down I watched her mouth chew the gum rapidly, cupping my hand I thrust it out in front of me for her to deposit the gum into it. Pushing the final button, Miss Gallagher spat the gum at me, landing it on my shirt. Holding one of her wrists, I told her sternly that she was not leaving until we got to the bottom of the poem. In a somewhat surprising omission, Miss Gallagher blurted out “Alright, I wrote the stupid poem, I thought it would be funny… sheesh”

“Ok then, we will see how funny you think it is by the time I’ve finished spanking you”

“Like I said, any reason to get your hands on my bottom”

I chose to ignore this last comment of hers and led her by the arm to the waiting couch. Sitting down I pulled the brat over my lap, watching her tiny skirt flip up briefly, it gave me a quick glimpse that she actually was wearing two pairs of panties today, obviously she was prepared for this spanking.

Raising my hand I started to apply it to the seat of her plaid skirt, going from cheek to cheek while admonishing her about the number of times that she has been over my lap in the past few weeks. All this brought was a deep heavy sigh and a comment that it was because I enjoyed spanking her. Ignoring the comment I continued to spank the seat of her skirt with little effect. I paused in the spanking and remarked that this seemed to be having little effect on her, almost as if she was wearing two pairs of panties! Caught you, you little minx, I thought to myself and grasped the hem of her short skirt. Pulling it up, I was expecting to confront her on the multiple pairs of panties, however, I was the one disappointed. There weren’t two pairs of panties, just a singular pair of light blue cotton panties that had pink elastic leggings, I had been fooled, and I had made the error of out thinking the brat.

On the back of the panties was a cute caricature of a couple of bees flying around and the saying written on them ‘Buzz Off’. Smirking at the incorrigible young lass I commented on how cute the panties were, but that she was the only one who was going to feel the sting. Pretty good comment I thought.

At this point I produced from my pocket two printed copies of the poem, one for her, and one for me to follow. I handed her a copy of the poem and informed her that I was going to continue to spank her bottom until she read the poem out loud for me. With a mock disdain, Miss Gallagher threw the piece of paper away and said “I’m not reading that stupid poem, I didn’t write the damn thing, spank the person who wrote it”

“I am spanking that person Miss Gallagher, remember, you just told me that you wrote it before I started to spank you”

“Err, well, SO, I’m still not reading the stupid thing”

Shaking my head I returned to the seat of the problem and began applying my hand to the blue cotton panties beneath me, making sure that I covered every inch and also being quite liberal with swats to her sit spot. There was still little reaction though; obviously this was going to take a while. Perhaps I spanked the seat of her panties for 5 to 6 minutes before I grabbed Miss Gallagher around the waist and lifted her body, and then somehow managed to reach over and pick up the thrown away poem. As I picked it up I also took that time to pick up the cracker barrel paddle off the coffee table. Once more I handed her the poem and demanded that she read it aloud. The only response I got was a repeat of her earlier comment about not reading it, and then watched her screw the poem up into a tiny ball.

With little said I grabbed the waistband of her panties and drew them quickly down to her knees, then continued spanking her now glowing pink bare bottom. I told the brat that I was not going to stop spanking until every last word was read, and told her she had better keep still. This brought out the funniest comment of the night when Miss Gallagher said “It’s hard to keep still with that ‘THING’ poking into my ribcage all the time”

With a slight blush I thought quickly and said “That ‘THING’ is my blackboard eraser young lady, and that should be the least of your worries right now”

With that I picked up the small paddle and started to spank her with it, telling her that if she didn’t start reading soon, I was going to spank her until she read it in full with this paddle. I put the paddle down and resumed with my hand and warned her that she had better start reading. Miss Gallagher’s bottom was now glowing red, I was a little surprised at how much she was taking, especially as not one word of the poem had yet to be read. Pausing once more I again returned to using the cracker barrel paddle, and this time I saw it was beginning to have some response from her. I gave her a final warning, she had better start reading the poem otherwise the rest of the spanking was going to be with the paddle.

So now I had given her a last chance, putting down the paddle I began once again with my hand, asking her to pick the poem up. By this point the young lady was beginning to squirm a little under my hand and I was a little concerned about having to use the paddle for the rest of the spanking. I wanted to make sure that she fully understood where I was coming from and that I was serious about this, so I picked the paddle up and applied it firmly to her glowing bottom, and said to her sternly “You pick up that poem right now young lady, otherwise the rest of your spanking will be with this paddle”

Well the paddle did the trick, obviously it ran through the girls mind that this really was it, could she really take the rest of the spanking with the paddle. A few sharp swats to her sit spot convinced her that no, she couldn’t. So without further ado Miss Gallagher roughly picked up the poem and started to unscrew it. Me on the other hand, I wasn’t waiting. My copy was already sat in the middle of her back and my hand was already in full spanking motion.

One of the problems in screwing the poem up, was that it became clear that this would be a lot harder to read as some of the creases smushed some of the words. Nonetheless, Miss Gallagher gave it a valiant effort:

“—Presently his soul grew stronger; “OUCH” hesitating then no longer, “ow ow” “Sir,” said he, “or Madam, truly your forgiveness I implore; “Ooh, ouch”

“But the fact is I was napping, “OUCH, damn it” and so gently you came rapping, “OUCH OUCH OUCH” And so faintly you came tapping, tapping at my chamber door, “Owwwww, ouch”— “

And so it continued, for 5 very long verses, Miss Gallagher repeated the written words in front of her; I tried to follow them with the copy pinned to her back. Each third or fourth word would be accompanied by an ow or an ouch, perhaps a vigorous kicking of the legs. The longer into the poem we got, the firmer and quicker the spanks landed upon her blazing hot bottom. Miss Gallagher had been in this spot before, she was fully aware that the spanking was going to build into a crescendo for the final verse and she was ready;

“—Then this ebony bird “OW OW” persuading his sad fancy into smiling, “Ooh, OUCH, OW” By the grave and stern “OUCH, OW, STOP” decorum of the _expression she wore, “OWWWWWW” “Though-thou-art-a-small-bird” he said, “thou-art-sure-no-coward, Gothic-black-and-brazen-raven-wandering-from-the-southeast-shore Tell-me-what-thy-bratty-name-is, bird-from-the-southeast-shore!”

“Quoth the raven “You’ll be SORE.” — “OUCH OUCH OUCH OUCH”

And with that we were done!! The last verse of the poem had been said at lightning quick speed, all the words meshing into one long word as Raven struggled to complete the poem with her body flying all over the place, and the temperature rising quickly in her bottom region. Miss Gallagher had made it through, perhaps very thankful that she had reconsidered taking the cracker barrel paddle for the duration of the spanking.

The young lady laid in position for a while as she caught her breath with deep intakes of air, all the time with one of my hands resting on her bottom, while the other cleared the sweat from my brow. Grabbing the panties from her knees, I eased them up as far as they would go to the top of her thighs, letting her lift her hips so that I could finish the task and draw them over the tender orbs, listening to the young lass wince as the elastic scraped over her tender bottom. Patting the pantied seat I told Miss Gallagher that she could now stand, then told her to go back to her class and that I hoped not to see her again in the near future.

From my seated position, I watched the pretty seat of her skirt swing as she sashayed away from me. While I was impressed at her stamina this time around, I got the biggest treat when the naughty schoolgirl almost departed from sight. It was only a fleeting moment, but she could no longer resist, in full stride Miss Gallagher reached behind her and began to furiously rub her very well spanked bottom. The sights do not get much better than that for a top.

This was the first of perhaps many sessions between Miss Gallagher and her Professor. Each time that I go down to visit Raven we will add an additional chapter to this story, the next one being a naughty drawing that Miss Gallagher has drawn of her favorite Professor.

In all the play sessions that Raven and I shared that weekend, I think that we both agree that this was both our favorite. The role-play ran so smoothly, the communication and the banter were perfect, and the fun was second to none. As a reminder of this session, I took home with me the screwed up copy of the poem that Raven had wrote, it is something that I can look at years from now, and be able to have an immediate smile brought to my face.

Richard Windsor.

2 thoughts on “The Errant Schoolgirl

  1. I find role play is boring I enjoy spanking girls for real at my house in school st llanbradach south Wales uk

  2. I’m glad to hear of your preference. That is the wonderful thing about our lifestyle though, each person has their own interpretation of what they find exciting.

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