Unlike a Virgin - A Private Discipline Session for Emily

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Obviously I am no longer in school. As a matter of fact, I just earned my Bachelor's degree. If you want to hear about how I was punished in school, I'll have to disappoint you. I never did get spanked there, it was against the law, thank God. No, I discovered the pleasure of spanking much later, in my third year in college. That is when I learned to become a proper schoolgirl. That is when I learned to bend over and pull down my panties. And I learned to say "Thank you, Sir" for each smack that landed on my bare naked virgin ass. But I'm getting ahead of myself.

It was out of utter boredom that I found myself browsing the personals section of an online bulletin board. One of the ads got my immediate attention:

Young Professional Schoolmaster looking for Professional Schoolgirl to love and discipline online. Must be naughty and adventurous. Punishments will be strict and severe.

Initially I laughed out loud when I read this. But I found my hand under my skirt while reading the ad again. About a year ago I did have a boyfriend who liked to take me over his lap. The spankings were playful and never failed to turn me on. Even though we broke up soon after that, the memory of his hand roaming over my bottom stayed with me. I've spent many nights since then fantasizing about getting spanked. Yes, I do touch and please myself, why shouldn't I? I prefer to sleep naked, in case you wonder. On my back with my legs spread wide I first gently rub myself until I get wet. Then I push my fingers inside and dream my fantasy. It's like a movie playing in my head.

Sometimes I turn over on my stomach. I put a couple of cushions under my belly to get the feeling of lying over somebody's lap. Lately I found myself wishing to get caught masturbating like that. I get interrupted by a stern voice telling me to stop at once. When I turn my head a see a middle aged teacher-type man with old fashioned glasses looking at me very seriously. With one hand he points at my hand between my legs. In his other hand he holds a spanking strap made of thick leather.

He tells me to grab the headboard with both hands. My face is burning, red with shame. Cold air brushes over my exposed bottom. "Twenty lashes, Emily!" he announces matter of factly. From the corner of my eye I can see him taking the first swing. The strap lands on my ass with a loud smack. "One!" I manage to say. The pain is not immediate, it gets worse with every second that passes. The next smack explodes on my bottom. "Two!" I already have tears in my eyes and can hardly keep still, but there are eighteen more lashes to endure. By the time I imagine the last lash ringing out I already had an orgasm.

Sorry, I digress. I've always had a short attention span. That's another good reason to look for someone to discipline me. I am kind of bubbly. Often I say things I later wished I hadn't. You know the kind of girl. So, I looked at the ad again.

Young Professional Schoolmaster looking for Professional Schoolgirl to love and discipline online. Must be naughty and adventurous. Punishments will be strict and severe.

I sent him an email telling him about my fantasy. I assumed it was a guy, that's what he claimed. I waited for an hour. Two hours. No answer. Typical. Often online information is old and outdated. This person placed the ad and nether bothered to check again, I figured. I turned off my machine and went to bed. At least I could dream about a schoolmaster teaching me good girl manners. Teaching me with that strap I talked about. Dreaming with my hand between my legs. And yes, I do moan out loud when I come.

The next day I was surprised by getting an email from Schoolmaster Brian:

"Dear Emily, thank you for your email. I noticed numerous spelling errors, but we can talk about that later. If you are serious, you'll have to get yourself a proper uniform: A white blouse. A red checkered schoolgirl skirt, the shortest you can find. The lower part of your bottom should be visible even when you don't bend over. A half dozen white thongs that leave your bottom bare. To be worn under the skirt. Three pairs of white knee-high socks. A pair of black stomper shoes. I expect you to wear your uniform when you answer me."

I was excited and went shopping right away. The skirt was impossible to find at the mall. I finally went to a sex shop and asked for it. The guy behind the counter was nice and didn't seem to be surprised, but I was red-faced once again and hurried to get home. I put on my new outfit and looked at myself in the mirror. Looking at my backside I kept wondering whether Brian would ask me to go out dressed like this. I was probably going to be arrested as a street slut if I did. But the thought of men staring after me did of course turn me on. I've seen women staring after short skirted girls too. It was time to answer my schoolmaster.

"Dear Brian, sorry for the delay. Took me a while to get my uniform. Have it on right now. The skirt is so short that I'm actually sitting on my bare ass in my leather chair. Feels good. Typing with one hand now. I'm rubbing my slit and I'm all wet. Got a full dozen of white thongs instead half. They'll get wet all the time. Wondering whether you want me to go out like this? Let me know."

What I wrote was actually true. Just after I finished and hit the send button I had a wet orgasm. The thong was too tiny to soak it all up, my inner thighs were glistening wet. I petted the sopped little thong and kept it on out of spite. I sent Brian another email.

"Thong all wet and soaked. Sorry. Couldn't help it. Emily."

The answer came the next day. Brian did not disappoint me. He was strict, alright.

"You nasty little brat! I'll take you by your ear and drag you to the punishment block. You will bend over the block, your backside to the classroom for the other twenty girls to see. You will reach back and pull up your skirt. The other girls gasp at the moment they see the tiny thong that leaves your bottom bare. I take your wrists and cuff them to a hook in front, with your arms stretched out. Ankle cuffs will force you to keep your legs together, but I also use a belt just above your knees. Lastly, the belt that goes over your waist. Now you are forced to stand with your legs straight, bent over, with your ass pointing up in the air. You are practically asking for a merciless punishment. One that will leave your bottom welted and blistered and glowing in all shades of red."

Wow! Strapped over a punishment block. I saw one of those online. There would be no escape. I got on my hands and knees to imagine it. I ran my hand over my ass, trying to feel every curve. Then I read on.

"I'll choose a slim cane made of rattan and soaked in water for maximum flexibility. I instruct the girls in the class to keep count. They are staring at your helpless bottom and they listen to the practice swings I take with the cane. Then it is quiet. So quiet, you could hear a pin drop. For a splitsecond you'll hear a whistling sound when the cane cuts through the air. Followed by a terrible smack that echoes from the classroom walls. Your whole body arches involuntarily. You are trying to breathe. The pain makes you burst into tears. Finally you let out a scream, a scream that comes from the top of your lungs. The vivid red stripe that crosses both halfs of your bottom has tiny ruby dots of blood on the right side. The girls are watching mesmerized. Finally they stutter "One!" They all have pearls of sweat on their foreheads, and they are wondering what is still to come."

My God! I was wondering what was still to come myself! I forced myself to take a break and take in the scene of my punishment. This was not a regular spanking, it was torture. A cane, soaked in water! That must be pain beyond imagination. And all the other girls watching! Wow!

"I will wait exactly one minute between each stroke. That gives you time to recover, to cry and to ask for mercy, before the cane cuts into your schoolgirl ass again. Can you hear the cane whistle through the air? The other girls almost jump in their seats every time the terrible smack rings out and paints another welt across your bottom. You will get ten strokes like this. And that's just the beginning.

Your classmates are watching with horror while I put the cane back on the rack and select a snakeskin pony lash for the next part of your discipline. I put it on the block next to you so you can have a good look at the slick, single-tailed whip. You turn your head and our eyes meet while I take my time rolling up my sleeves. Tears are running down your face and you are drooling a little. But bear with me. I pick up the whip and run my hand over your sweet schoolgirl behind. I point out the wet spot on your thong to the other girls. If they had any empathy for you before they will surely loose those feelings now.

Imagine the sound of a pistol shot. Because that's what it sounds like each time the pony lash bites into your bare ass. Ringing smacks of cracking leather. The single-tailed end leaves looping and curling whip prints on your bottom. Your ass cheeks are twisting, trying to escape the lash. You scream uncontrollably, drool is running out of your mouth, yet one lash after the other whips your bare bottom flesh. And I am no longer taking extra time between lashes. To do your bottom honor you will get at least fifty with the pony lash. For each one I will measure my distance exactly. I will use all my strength to thrash your behind as hard as I possibly can. There will be no spot on your little schoolgirl ass that is not marked with an imprint from the whip. By the time I finish I will be covered in sweat from the exercise. The narrow tail of the pony lash will be bloody, of course."

Good grief! My mouth was wide open with disbelief while reading my punishment. I imagined what my bottom would look like, but it was hard to believe that would be sexy. Maybe to Brian it would be. He certainly knew how to discipline schoolgirls.

"You will be left tied up over the punishment block for an hour afterwards. The stripes of the cane will slowly turn purple. It is obvious to the class that your entire ass must be burning like a wildfire. The girls nod approvingly when I spread soothing Aloe gel over your behind. That will cool it down, but it will also bring out the radiant colors of the whip marks for all eyes to see. Then I will lead a discussion on how many days it will take before you can sit on your bottom again. Estimates might vary from one week to two weeks, but the whole class agrees: As soon as you can sit, you must be whipped like this again. Because you are a naughty schoolgirl. And this is the only way you'll learn!"

I emailed him back that he might be right about that learning part. But for now I had to go. I met a guy a few weeks ago and he was to come over to my place. I had slept with him last week, and I told Brian that after reading my punishment I felt like I needed some real sex.

So I waited for Andrew like this, on my hands and knees. Of course he was surprised, but pleasantly so. Then I started bubbling about me being a bad girl and told him about my virtual punishment. Andrew took me over his lap right away and slapped my ass. Between spanks he rubbed my slit and scolded me for my wet panties. Those got more wet by the minute, of course, how could I help that?

I was wide open when Andrew plunged into me from behind. I love it that way, it's deeper, with his loins slapping against my ass cheeks. He pulled my hair and scolded me while he fucked me. He called me a brat. A bad girl. Once in a while he slapped my ass. He made me come three times that night.

I think my uniform was an excellent investment. But I'll have to get us a cane for future punishment. I am rather curious now. Anybody know where to buy a pony lash?