I Hate Costume Parties!

I don’t like dressing up; I never did. Even as a kid at Halloween, the only good thing about the day was wandering around with friends at night and getting free candy! I usually tried to avoid adult costume parties, partly because of the costume aspect of it, but also because there’s inevitably a lot of drinking going on. I don’t drink liquor; it makes me sick, so wine and beer are my only alcoholic beverages, and even those I don’t drink more than one or two, beyond which I’m impaired, which I don’t like, and I hate being around a lot of drunks with all the BS, silly drinking games and flirtatious attitudes.

I wouldn’t have come to this one except a friend told me it was usually a great party, good hosts, reasonable guests and the important one, lots of girls, often dressed in sexy or revealing costumes. So, I went. Dressed only in a suit, I could claim to be any one of several things depending on whom I was talking to, a doctor, lawyer, etc. Given the number of naughty schoolgirl costumes I saw, perhaps Headmaster would work out? There are always the predictable costumes; monster, zombie, bum, cop, stripper (male or female), French maid and then a few good ones; funny ones. There was a couple, one of whom was peanut butter and the other jelly, prompting endless jokes about when they’d make a sandwich. There was a woman dressed as a brick, and her husband was a bricklayer.

Given my love of spanking, it was logical that the naughty schoolgirls would be the most interesting to me. I counted at least four at the party and thought I’d seen a fifth, but it might have been one I’d already counted. Three of them were dressed scantily, that being the naughty part; cleavage bursting out of an unbuttoned blouse, ultra-short skirts that bending over even slightly revealed the requisite white panties, thigh highs, crop tops, etc.

One, however, looked much more authentic. She had a nice body, but she let the tight clothing stir the imagination rather than openly displaying her wares. Her blouse fully closed to the neck, with one of those short ties, which cross over at the ends. Her skirt was short, a little above mid-thigh but not up to her crotch. She had a cute face that wasn’t overly made up and her nerdy glasses (part of the costume) and ponytail again looked more authentic than the others whose makeup bordered on a prostitute’s. Add white knee socks and proper black shoes and she looked like she’d just gotten off the bus from Catholic school.

She was standing by herself near the entrance to the living room, with an occasional short encounter which couldn’t have been much more than saying ‘hi’. I was partway through my second glass of wine, so with a little false courage I decided to talk to her. She smiled as I approached.

“Hello! I must say that your naughty schoolgirl outfit is the best here tonight! Very realistic!” I added.

“Thank you!” she replied. “But I’m just a schoolgirl, not a naughty schoolgirl … at least not yet!” she added with a cute, little smile that was meant only to be funny, not sexy.

“My name’s Mark,” I said holding out my hand.

“Hi, Mark! I’m Erin,” she replied taking my hand with a firm handshake. “What are you dressed as?” she asked with mild interest.

“I don’t know!” I said with a laugh. “I’m not a major fan of costume parties, so this can be whatever it looks like! With all the schoolgirls here maybe, I should be the headmaster!?”

“Mmm!” she said with seeming interest. Just as it was starting to get interesting somebody came along and dragged her away saying there was someone she just had to meet. I went back to the living room and found the only place to sit, which was on the fireplace hearth. I had short conversations with a few people who were usually intoxicated, which is why they were short.

Alone again, I was thinking of how I should make my exit. ‘Should I just leave or make some excuse to the host?’ I asked myself when Erin showed up and sat right next to me.

“Hey!” I said, genuinely happy to see her.

“Sorry about that! Some guy they thought I’d like. I didn’t. So, where were we?” she asked with an impish smile.

“I was about to ask you when you’d become a naughty schoolgirl?” I replied trying to measure her interest. Are her suggestive comments just teasing conversation or was there some interest?

“Well, I guess that would be when I’ve done something I need to be punished for!?”

“Hmm,” I said stalling for time and an answer, “and who would be the one punishing you? Would it be:

A- Your daddy who puts you across his knee and spanks your bottom to teach you a lesson? OR

B- The Headmaster of the school whose uniform you’re wearing who spanks and paddles his students to instill discipline? OR

C- A teacher who suggests he give you a spanking in exchange for the improved grade you were looking for?”

“B”, she says.

“B?” I ask.

“B – the headmaster,” she replies with a sexy smile.  “Of an all-girls school.  You know, a couple hundred teenage girls with raging hormones and no boys around to take care of them,” she adds with a naughty smile.

“Okay, so what kind of headmaster is he?” I ask ready to present another multiple-choice question.  “Is he:

A-  A by-the-rules headmaster who has the girls raise their skirts and bend over his desk for a good paddling, and whether he takes their panties down depends upon the severity of their behavior? OR

B-  A lecherous headmaster who considers the permission to spank his students one of the benefits of his job while he takes his girls over his knee for bare-bottom spankings and the prettiest or shapeliest girls find his hands and fingers wandering? OR

C-  One who’s in between those two who takes discipline seriously, but is occasionally taken in by that rare girl who enjoys receiving his punishment and encourages his wandering fingers as she lays bare-bottomed across his knee?”

“Ooo, definitely C!” she says emphatically.  “So, are you:

A-  My friend trying to console me with encouraging words of ‘You’ll be alright’ or ‘You can take it’ as I make my way to the headmaster’s office at the end of the day as ordered by my teacher? OR

B-  My brother who delights in my predicament and tells me I deserve it; that it’s about time I got seriously punished for the behavior that got me into this school to begin with? OR

C-  My headmaster?”

“C of course!” I said both of us now smiling. “And what have you done to deserve this punishment? Is it:

A-  Clowning around and disrupting your English teacher’s class? OR

B-  Talking back to the teacher and disrespecting him in front of the class OR 

C-  Who cares? I just want to get punished!”

“D!” she says leaning closer to me. “All of the above!” she clarifies. So, do you:

A-  Write me off as some kinky, weirdo tease who you won’t get anywhere with? OR

B-  Think this is interesting, but not your thing? OR

C-  Want to take me over your knee right now and give me a good spanking with my panties down?”

“C! Definitely C, though I don’t think you really want it ‘right now’, but is there somewhere better nearby?”

“My apartment is in the building across the parking lot,” she says, putting her hand on my thigh, and adds, “Sir!” We left the party at once without saying a word to anyone and walked over to Erin’s apartment. Unlocking the door, we both stepped into a living area that was a mirror image of the one we’d just come from.

“I use the second bedroom as my office which should suit your purposes, sir. Call me in when you’re ready for me!” she said and added, “Oh, and look in the bottom right drawer!” I walked down the short hallway, easily found the room, and went in. Her large wooden desk was in the center of the room with a high-back executive chair behind. There was one small armless chair in the corner, which I moved in front of the desk for Erin.

Taking my seat behind, I looked in the suggested drawer and found her cache of sex toys including the normal vibes and dildos, but also some handcuffs and several paddles. I chose two; a small round leather paddle good for over-the-knee use and a long school paddle of thick, light-colored wood with the requisite holes drilled in the paddle’s face. Ready! I went to the door and peeked out.

“Miss Erin?” I called out not seeing her.

“Yes, sir? Here I am!” she said coming out of the bathroom.

“Get in here right now, young lady!” I said as sternly as I could manage. Erin followed me into the room and sat in the chair I motioned to while I took my seat behind the desk. “Well Miss Erin, you seem unable to get through even a few days without getting in some kind of trouble. Mrs. Henry this time?”

“Yes, sir. I like Mrs. Henry and I’m sorry I made a scene in her class.”

“Why don’t you tell me what happened?”

“I was goofing around with my friends, I guess kinda making fun of what she was trying to teach us. When she yelled at me for it, I told her to ‘fuck off’.”

“Well, at least you're honest about it. That is what she told me as well. You realize this is a serious issue and will require considerably more severe punishment!”

“Yes, I know it’s serious, sir. How much more severe?”

“In addition to a much longer spanking, you will also be punished with both of these,” I said pointing to the paddles sitting on the desk. “Also, most of it will be on your bare bottom! I will start with a hand spanking across my knee on your panties, but they will quickly come down for more spanking with my hand and the small paddle. Then you will bend over the desk for a dozen swats of the school paddle and if you give me any trouble at all I won’t mind increasing the count on any of them!”

“Holy shit! Please don’t …”

“Such language! Now it’ll be eighteen with the school paddle! Want to try for twenty-four?”

“No sir!” she said quickly. “I guess you want me to ask for my punishment like usual?”

“Yes, please,” I said, liking her suggestion.

“I have behaved horribly, sir. I’m deeply sorry. Please give me a spanking and a paddling on my bare bottom.”

“As you wish. Stand up,” I commanded and walked around the desk to sit in her chair. “Lift your skirt!” I added recognizing that as tight as it was, it would be difficult to get out of the way once she was on my lap. She left her skirt banded about her waist, revealing a pair of bright red and very tight panties that covered most of her lower cheeks where I tend to concentrate my swats. “Over my knee!” I said pulling her down by her left forearm to her position on my lap.

Without warning, I began spanking her on her tight panties, getting lots of ‘Oh’s’ and ‘Ow’s’ as I did, but she was also showing signs of enjoyment. Even after a long flurry of spanks on one spot, she raised her bottom up inviting more. I wasn’t counting but I’d guess we were nearing a hundred when I decided to take her panties down.

“Pleeeease, sir! Not on my bare bottom!?” she cried as my fingers slipped under the elastic waist. Dragging the tight elastic across her red cheeks got a positive reaction. Once below her cheeks, I had to peel the damp fabric of her panties away from her moist crotch and leave them just above her knees.

Perfectly round, squishy cheeks came into view that some might say showed ‘a few extra pounds’ but I thought were magnificent. I could already picture them jiggling around like a bowl of Jell-O when spanked. I couldn’t see much of her pussy, just a shiny, slick slit that I hoped I’d get a taste of!

“This is the first time I’m spanking you on your bare bottom, young lady, but it won’t be the last if this behavior doesn’t change. Do anything like this again, and you’ll be naked from the waist down and bent over my desk from the outset! Do you understand?”

“Yes, sir,” she replied with a small voice.

Her cheeks were every bit as entertaining as I had expected when the spanking resumed. Bouncing and jiggling with each spank I was truly enjoying myself … and Erin was showing similar signs of pleasure already. Spanking with just my hand for almost ten minutes with a few short breaks had her moaning and almost writhing on my lap as the spanking continued and intensified!

During the short rests, my hands would be all over those beautiful buns, caressing and squeezing gently. At each rest my hand would stray a little further down her curvy thighs, closer and closer to her magic place, her reaction being to spread her legs as far as the panties around her thighs would permit.

It was almost time for the little paddle, but I so enjoyed touching her sexy ass, I didn’t want to stop spanking. When I did finally stop, she didn’t know I’d be changing to the paddle, but this time my middle finger slid very gently up through her wet slit to the tight, little hole between her cheeks where I pressed a fingertip hard just short of inserting it. A low, soft moan while my finger slid through her flooded slit, and an ‘Oh sir!’ when I pressed on her tight rosebud.

“Do you have to paddle me, sir?” she asked when she saw me reach for the small, leather paddle.

“Do you think I should just let you off now?” I said making the proposition sound ridiculous.

“No, sir. I’ll take my paddling.”

“Yes, you WILL!” I said emphasizing the word with the first hard swat. Feeling she was well warmed up, I started with a fast-paced, alternating cheeks pattern, concentrating on her sit spots. Her face and body were giving away just how much she was enjoying it, with long extended moans and lifting her bottom up to meet a long series of swats on one cheek alternated with her grinding her crotch into my thigh.

The paddling continued turning her bottom gorgeous shades of deep pink and red, which I made sure was spread all over her bouncing butt. Loving each and every swat, I finally got a few more ‘Ow’s’ out of her with much harder, repeated spanks on one spot of each cheek in turn, getting her to moan and squirm on my lap.

“I’ve got a feeling you’re enjoying this a bit too much, young lady!” I said accusatorily.

“No sir! I’m not! Please!” she protested unconvincingly. I repeated the last series of swats even harder, getting the same pained reaction during and pleasured reaction after. I repeated it once again before I decided it was time for the school paddle. I hoped to get her to admit she liked it after the hard paddling, knowing that we would be finished I had a feeling she’d want more. “Alright, get up! Time for the school paddle!”

She got up looking at me with a small smile escaping. Pushing her towards and then down over the desk, she allowed me to put her in position. Hoping she’d spread her legs more if given the chance, I pulled her panties down to the floor and off and was rewarded with an excellent view of her sopping wet pussy when she spread her legs just enough!

I picked up the wooden paddle and it was heavy! It was her paddle; she bought it! Even so, I decided to take it a little easier than originally planned as a beating with this thing could easily put her off anything else, let alone another spanking.

“Eighteen swats, young lady! Are you ready?”

“Yes … yes, sir,” I tapped the paddle a few times across both cheeks, taking aim, pulled the paddle back, and landed a perfect swat evenly across the fleshiest part of both cheeks. “Oof!” was her only reaction. The second identical to the first got no reaction, so the third was a little harder. “Ow!” she said as though she was expected to say it. Okay, three swats quickly in a row in about the same place! “Oh god! Ooo!” this time with more feeling. I liked that pattern … three slow and three fast … and decided to continue with it for the remaining twelve. “Ow-ow-ow-ow!!!” she cried convincing me I had the right formula after the next six.

“Six more! Do NOT get up or rub your sore bottom until I say so! Understand?”

“Yes, sir!” she said with desire in her voice. The final six got a similar but somewhat more pained response as they were harder. I put my hands on her very warm cheeks, caressing and rubbing them both identically, which had Erin moaning again. Circling her sore butt, my hands gradually made their way closer and closer to her glistening, wet pussy eventually running fingers from both hands repeatedly through her slippery slit in succession which got her both moaning and squirming on the desktop.

“Okay, you can get up now,” I said as I abruptly stopped fingering her slit leaving her wanting more. She stood up looking confused but managed to rub her sore cheeks in a perfect imitation of a freshly spanked schoolgirl! “I hope you’ve learned your lesson!?” I asked and got a little nod in response. “I don’t think you’ll want to get paddled again anytime soon, will you?” I asked, getting a head shaking ‘no’. “But you did enjoy it didn’t you?” A nod. “… and you want more, don’t you?” Another smaller nod.

“I think you need another spanking! Over my knee!” she nodded to the first statement, but not the second. Instead, she found the zipper at the side of her skirt, opened it, and let the skirt drop to the floor. Her blouse was the next to go followed by her bra, allowing two small, but perfectly shaped tits to escape. Before I could fully react to this arousing strip tease, she turned and bent back over the desk.

“Please spank me, sir!” she said in the cutest, little voice with an even cuter smile. Lowering her body fully onto the desktop, her tits pressed into its solid surface, she looked back at me, spread her legs widely, and repeated, “Please?”

Putting one hand on the small of her back, I resumed smacking her fleshy orbs which immediately got a raised bottom invitation to continue the spanking and, with her legs spread wide I thought, the fingering of her wet cunt. Slipping the fingers of my left hand down her crack, over her rosebud: a little jerk there and into the flooded valley of her pussy. I spanked around my left hand letting it do what she really wanted with the smacks as added stimulation.

After a minute or so of teasing her pussy, I pulled my hand up again and stepped up the spanking to fill the gap. Testing a theory, I slid my middle finger down her crack again and with the spanking in full swing, I pushed hard on her tight, little hole which got another immediate reaction, pushing her hips up seemingly wanting my finger inside. Pressing harder, my fingertip teased the opening and pushed in to the first knuckle. “Oh fuck!” she cried pushing up harder wanting more of my finger. I stopped spanking to allow my other hand to slide into her gushing pussy.

“No! Don’t stop spanking!! Please!?” she cried, and I resumed as my finger slid slowly but steadily into her bottom, wriggling all the way, which had her wriggling on the desktop as well. “Oh my GOD!” she yelled.

There was no way I wasn’t going to get a taste of her pungent pussy, so kneeling behind her, with one finger in her ass, the other hand spanking away, my mouth found her slit, and my tongue her clit and with the combined stimulation she was literally shaking as she approached her climax. Seeing her reaction, I stepped up everything. Spanking repeatedly in one spot on her right cheek, plunging my finger as far as it could go into her ass, and nibbling and licking her clit she came like an eruption, her body quaking on the desk as she squirted copious amounts of her pussy juice all over me.

As I watched her shaking from her explosive orgasm, I started pulling my finger out of her bottom, but was stopped by her hand pushing it back in. She looked back at me through tears of joy and asked, “Fuck me? Please?” she begged as I again started to pull my finger out only to be stopped again. “In my bottom, Mark! Give me a good fucking in my ass!” she pled, raising her bottom up again in invitation. This time she didn’t stop me when I pulled my finger out.

I’ve only had a little experience with anal but loved it the couple of times I got to do it and I knew we needed more lubrication if I was going to get my thick cock in that tight hole. Borrowing some juice from her pussy and surrounding drenched areas, I fingered her ass again to get as much as I could inside, Erin moaning all the while. Teasing her asshole open with my finger, I managed to open my pants and get them and my underwear down around my ankles with just one hand. Holding my stiff rod in my hand, I pulled my finger out and pressed the tip of my dick against her little hole.

“Oh yeah!” she said as she reached back and spread her cheeks with her hands as much as possible. That only made the target easier to see, not penetrate. I teased with the tip of my dick, pushing, and rubbing all around the area, at one point seeing her sphincter relax just a bit, I went for it … pressing hard into a vise-like grip in her butt! She slowly relaxed enough to get full penetration, where I just stopped for a moment, wiggling a little in her ass. “Oh god! Fuck me! Fuck my ass, Mark” she commanded as I slowly moved a little further in and out with each gentle thrust and I could feel her loosen up more with each stroke.

It wasn’t long before my cock was like a piston in her cylinder, and a spark at the top of each stroke had us both grunting, groaning, and moaning as I slammed into her hips harder and harder. Somehow, in her tight grip, I managed to hold on long enough to see her cum again with a similar shuddering climax, just before I emptied my load into her ass feeling her squirted juice running down my leg.

She remained lying on the table enjoying a light back massage from me as we both calmed down. Finally standing up, she turned, threw her arms around me, and gave me a big, sloppy, wet kiss. “That was amazing!” she said as our lips separated. I mumbled an ‘I agree’ as we kissed again, this time tongues entwined and hands exploring each other’s sensitive areas.

Wanting another taste of her delicious pussy, I picked her up and sat her on the edge of the desktop. Spreading her legs, I dove in for a proper pussy licking, my tongue, and fingers in overdrive from the start. Sucking her meaty lips into my mouth, my tongue darted about her slit and up inside her as she was writhing on the desk.

Grabbing my head, she pulls my face hard into her dripping wet crotch and groans when she feels what happens when you encourage me to lick harder. Finally able to pull my face away, both of my hands get in the action with fingers of one hand in her pussy and the other in her ass, while my tongue concentrates on her clit, soon after which she reaches another shattering climax drenching my face and falls back on the desk to recover.

Having returned to full erection while feasting on her cunt, her dripping, slippery, swollen pussy calls to me begging for its own penetration, and pulling her knees further apart, I slide in easily much to Erin’s pleasant surprise. Nearly completely spent, she contributes to the motion as much as she can while yelling ‘Oh my god!’ and ‘Yes!’ repeatedly as we both rocket towards the precipice again.

Taking hold of her hips, I pull her off the desk just till her butt is clear, and grabbing those sore cheeks I pound her pussy, with an occasional hard slap on her bottom! Panting and gasping for air, we go over the edge almost simultaneously, shaking uncontrollably. Once stable, I fall forward on top of Erin, kissing her tenderly before helping her to get up and off the desk.

“Wow!” we both say in unison as we stand facing each other. I pull my pants back up and fasten them.

“Have you learned your lesson, young lady?” I ask as I take her in my arms again.

“Oh yes! Yes, sir!” she says as we kiss briefly and then turn to leave the room making our way out. She goes into the bathroom briefly returning with a towel she hands me to wipe ‘her’ off my face. Heading for the door, we know we’re not going back to the party. Erin, still naked, wants to stay that way and I make a play to stay and enjoy that, but she’s tired and going to bed.

“Well, I hope you’ve learned to control your behavior better! If not, I’ll be seeing you in my study again, won’t I?” I say standing in the doorway.

“Oh yes, definitely, sir!!” she starts with an impish smile and bitten lip. “SEEing me! SPANKing me! PADDLing me! LICKing me! … and FUCKing me!!!” she says with emphasis on each action and a pause before the next. Then after a little kiss through a small gap in the doorway, she closes the door behind me.