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Fancy Dress or Undressed

"Sexy schoolgirl outfits can put a strain on a friendship."

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I shocked myself a bit when I said it out loud. Mostly I’d been attempting to amuse my friend Rob. He had a huge talent for, and interest in, inappropriate comments. But he had perhaps mastered the art of making such comments sotto voce, or at least quietly enough to not be heard by the person referred to. Just for a moment, I hoped that Sarah hadn’t heard, but she turned and approached me. I expected to be slapped in response. When I looked around, it seemed that Rob had also mastered the art of disappearing, leaving me entirely alone to face Sarah.

The student club of the residential university college was hosting one of its legendary annual parties – this one fancy dress. The idea was that you came as something starting with the first letter of your name. Traditionally, people got a little bit wild, since this was the last big party before the end of year exams. However, as a residential tutor, I decided putting on a suit and tie, and being a ‘businessman’ was good enough. B for Brian; B for businessman.

It seemed like a sensible outfit, since I’d drawn the short straw and was ‘duty tutor’ for the evening. This meant that I was supposed to be the responsible adult, even though I was only twenty-three. In particular, I was tasked with making sure that there wasn’t any trouble and that the party closed down on time. But there were a few other tutors around who would help out if needed, and it was a small college – small enough that everyone knew everyone else – so mostly the students watched out for each other. By this time of year, they all knew that the policy was that anyone who ended up paralytic would wake up down the road in the hospital emergency room having their stomach pumped. The nurses weren’t sympathetic to students whose only medical issue was a combination of alcohol and stupidity. So overall, I wasn’t too worried about trouble, and had knocked back a few beers.

Anyway, this particular fancy dress party saw the usual amount of daring dressing from the girls. Well, they were young women really – all between eighteen and twenty. Bianca had come as a ‘bikini model’, with a bikini top, and a short sarong around her waist. Rhiannon had (apparently on a dare) re-hashed her toga party outfit – she was a ‘Roman', except that this time it seemed that she had decided to go without underwear. All the guys were trying to check this out, but I didn’t foresee any problems there, since her boyfriend was almost seven feet tall.

But the girl who really caught my eye was Sarah.

Now, Sarah and I had been friends for a while. Or at least, we’d spoken a lot about books, music and chemistry. She was in her second year of a science degree, and considering majoring in chemistry; whilst I was doing my PhD in organic chemistry. I couldn’t help but think that there was a little bit of chemistry between us. She laughed at my jokes just a little bit more than needed and I smiled like an idiot when she said something nice about me. But that was about as far as it went. Since I was in a position with some tiny amount of authority at the college, I wasn’t really supposed to get up to anything with students. Of course, I wouldn’t have been the first to do so; in reality, the reason I hadn’t tried anything was that I wasn’t very confident around women.

For that one night, Sarah had shed her usual outfit of jeans and loose T-shirts, and instead dressed up as a schoolgirl. Her tartan skirt was very short and her white shirt unbuttoned dangerously low, clinging tight against her breasts. Somehow, pretty-faced, quiet, studious Sarah had become the stuff of fantasies.

So, I had said something rather inappropriate. “Well, there’s a fantasy that I didn’t know that I had.”

As she approached me, I had many thoughts rushing through my head. ‘What did I just say?’ and ‘she’s going to slap me,’ were largely being drowned out by the recurring thought, ‘My god, look at those boobs!’ But I did try to concentrate. ‘I need to think of a way to apologize. I’m sorry, actually, I did know that I had that fantasy... hmmm... maybe not... maybe I didn’t mean it like that, I meant... would you like to read a fantasy novel?’

And the slap never came.

Instead, Sarah just said, “Good evening, Mr Carter. Are you dressed as a headmaster?”

She cast her eyes downwards, as if playing the part of submissive schoolgirl. This was really playing up to my recently-discovered fantasy.

Now my thoughts moved on. ‘Maybe she didn’t hear me... hang on, neither headmaster nor principal start with B... NO... don’t say that!’ I bit my tongue just in time. It took me a few moments, but I did finally realize that maybe, just maybe, Sarah had a related fantasy herself, and that it might be interesting to play along a bit.

“Well yes, young lady. And I think we need to talk about your uniform standards.” I allowed my eyes to wander over her body.

She saw that I was leering a little, and blushed. If I wasn’t mistaken though, she suppressed a little smile.

“Is that skirt regulation length?” I asked.

“None of the teachers have complained!” She placed her hands on her hips in defiance, which only served to hike up the skirt just a little more.

“No, well, I don’t suppose any of the male teachers would. But your shirt is certainly in violation of Regulation 11 of the uniform code.”

“Really? Regulation 11, you say, sir?”

“Err, yes. Umm, that regulation...” Pretending to be a headmaster was not quite as easy as I’d hoped, but I pressed on. “You should be aware of all the rules and regulations by this stage of the year. And given your recent behaviour, I think this time I will have to inform your parents.”

“Oh no, sir. Please, not that. I’d do... anything.” This was accentuated by a shy glance at her feet, and her entire face blushing red.

I wasn’t quite sure whether she meant what I hoped she meant, but my body responded. I shuffled a little in an attempt to hide my erection, which perhaps only drew attention to it, and I thought I caught Sarah taking a quick glance at my crotch.

“Well... I’ll see you in my office at 11:30pm on the dot.” I wondered whether I should have said, “In five minutes.” Certainly, that was what I wanted, but I couldn’t just leave the party so soon after the start. For one thing, I was supposed to be supervising.

“Yes, sir. I’ll be there.” Sarah turned and headed off towards the drinks table.

I stared at her arse as she walked, and a wicked thought crossed my mind. “Miss Fitzgerald.”

Sarah spun around and returned silently, a slight look of worry in her eye.

I wondered if she was worried that I might push for more, or that I might back out of our little deal. ‘Still,’ I thought, ‘having gone this far, I might as well go a little further.’ So I said, “I was just wondering whether you have regulation underwear on under that skirt.”

Again, Sarah’s eyes widened, perhaps shocked at my unexpected boldness. But she didn’t back down, or call an end to our little game. “Er, regulation underwear sir?”

“Bloomers, Miss Fitzgerald.”

She let out a bit of a laugh, and then stopped herself. “Bloomers? What the...”

I could only shrug. I didn’t really know exactly what bloomers were – it was just the first word that popped into my head. She looked me in the eye, and we both fought back laughter.

I tried to get back into character. “Yes, Miss Fitzgerald. Bloomers are to be worn at all times whilst in school uniform. What exactly are you wearing?”

She leant in close, and spoke in a soft, sexy voice. “It’s a G-string, sir. A tiny little black one.”

My cock hardened even more just thinking about it, but I decided on one more push. “Well, you will need to remove that before you come to my office.”

Sarah stepped back and raised her eyebrows. Then, in a very composed manner, she looked me straight in the eye and said, “Yes, sir.”

***

The next hour of the party was relatively uneventful. I thought about the college principal in her underwear (she must have been seventy, and I loathed her enough that I wouldn’t mind too much if I was kicked out for fraternising with the students). Then my erection subsided enough that I could walk around the hall without embarrassment.

I caught a glimpse of ‘Roman Rhiannon’ in the right light, and saw that she clearly was wearing a G-string, even if she had left off the bra. A few of the guys were clearly disappointed, but for me, it just reminded me of what Sarah had said.

I checked in with the student club president and made sure that he understood the 11pm curfew for the party, explaining that our neighbours would complain to the police if the amplified music went beyond that time. Of course he did understand that, but I had become very interested in everything going smoothly at the end of the party. I knew most of the students would be heading straight off to the nearest bar, but I hoped Sarah would not be.

Meanwhile, I watched her dancing – she was a good dancer, but mostly I was admiring her long legs in that short, short skirt. Many of the male students were obviously keen to attract her attention (including quite a few who had probably barely noticed her in her usual outfits), but she seemed happy dancing with a couple of her female friends.

My watching was interrupted by some shouting from outside, and I went to investigate. A couple of first year students were exchanging insults, but some senior students had already separated them. I checked that there was nothing seriously wrong, told everyone to calm down or else we might have to call an end to the whole party, and that was about it.

When I came back inside, my eyes searched the room for Sarah, but she was nowhere to be seen. Then I felt someone behind me – one hand grabbing my arm, and the other hand pushing something into my pocket.

“A gift for you,” said a voice I recognized as Sarah’s. I reached into my pocket, but she whispered in my ear, “Don’t take it out here.”

So I ducked into the men’s toilets, locked the door in a stall, and reached in to my pocket. I pulled out a tiny black G-string. My cock hardened again, as I thought of Sarah in that short skirt with no underwear, and then even more as I realized it must mean she was still intending to make our 11:30pm date.

I took the G-string back to my room – I didn’t think that I could carry it around all evening. I quickly cleared some dirty clothes off the floor and then looked again at the tiny piece of fabric that Sarah had stuffed in my pocket. I felt some dampness, and wondered if Sarah was as excited by our little game as I was. I couldn’t resist a quick sniff. The scent seemed to bypass my conscious mind and go straight to my cock, which was now as hard as it had ever been.

I was desperate for a quick wank, but I felt that I needed to rush back to the party in case I had been missed. At that stage, in my view, the most important thing in the whole world was that the party shut down on the dot of 11pm. Then the senior students could pack away, most of the others would head straight to the pub, and I could get back to my room.

I just hoped that Sarah wouldn’t back out in the couple of hours remaining.

***

Those hours seemed very, very long indeed. The party went by as most of them do. I slowed my drinking quite a bit – in theory, I was supposed to be more sober than I was, in case anything went wrong. I spent most of my time chatting with fellow tutors, and a few students. I did get dragged out onto the dance floor for a few minutes, but dancing is far from my forte, so I took the excuse to go and help serve drinks. That wasn’t really my role, but did mean that the student club helpers could have their turn on the dance floor.

During a quiet moment, I sat down on a chair and Sarah came over and sat down on the drinks table in front of me.

“Thank you for your little gift,” I said.

“Just showing that I’m willing to do anything that you ask.”

Again, she put an emphasis on ‘anything’ which made me catch my breath.

“I was just thinking, sir,” she said.

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“Have you ever seen the movie ‘Basic Instinct’?”

Just for a moment, I had thoughts of icepicks, but then I thought of perhaps the most infamous scene. I looked down at Sarah’s long legs, dangling off the table just in front of me. Her knees were pressed together, and her school skirt sitting on her upper thighs. When I looked up to her face, she was smiling broadly.

“Yes, I saw that,” I said.

“Oh, did you find it... exciting?” She slid forward on the table, the skirt riding higher and higher.

“Well...”

I think I just sat there, with my mouth half open, as she slowly lifted her left leg and crossed it over her right. In truth, in the dim lighting, I didn’t see much, but just the thought was enough to make me want to suggest that we forget about waiting until after the party, and head straight back to my room. Hell, I wanted to do her there and then on that table.

Sarah just smiled and looked up at the clock. “I’ll see you in an hour. I hope you won’t be too hard on me. I don’t mean to be so naughty.”

I gulped, but I wasn’t going to stop playing my part. “Well, you might be surprised how hard I can be. I think I’ll have to teach you a lesson.”

“Yes, sir. There was just one more thing I was going to ask. Do you think this bra meets uniform standards?” She let her shirt fall from her shoulder a little, showing the top of her lacy white bra.

“Hmm, no, I don’t believe it does. You’ll need to take that off before reporting to my office.”

“Yes, sir.” She headed back to the dance floor, wiggling her arse just a little more than she would have needed to, even allowing for the heels she was wearing. I chuckled a little, thinking that her shoes were certainly not school uniform wear, but that wasn’t what she’d be taking off next.

***

I made it back to my room at 11:25pm. I had hoped to see Sarah there already, but since she wasn’t, I went in and tidied up a little more. I got the idea to move my desk to make it a little bit more of a ‘meeting with headmaster’ environment, although I imagined we’d drop any pretence of that soon enough.

Then I sat down, planning to wait patiently. But my mind was racing with the events of the evening, and images of Sarah in just a shirt and short skirt, so I found myself pacing back and forth. Then I noticed that 11:30 had ticked by, and there was still no sign of Sarah. I sighed. ‘Did I push things too far?’ I thought. ‘But she pushed for the bra to be off... hmmm, maybe she’s just lost her nerve. I’m certainly nervous, and I’m the man... she’s just a nineteen year-old girl.’

Knock, knock, knock.

I was startled. It was 11:33pm. ‘Christ, three minutes late’, I thought, ‘and I was about to give up hope.’ I took a deep breath. ‘I’m supposed to be the confident headmaster about to take advantage of a sexy young student.’ I straightened my tie and opened the door.

I drank in the sight for a few moments. Looking down, I could clearly make out Sarah’s breasts through the shirt. She was carrying a backpack – the straps over her shoulders just seemed to draw even more attention to her breasts. As she had promised, the bra was gone. And as I had dreamed, her nipples were poking through, clearly showing her excitement.

She shuffled a little from foot to foot, and I could see nervousness in her eyes.

“You... er... wanted to see me... sir?”

I snapped out of my trance, and slid back into character. “Come in. You’re late young lady! Can you explain yourself?”

Sarah took a quick breath as she stepped past me into the room. “Well, I...” She turned to look at me, then cast her eyes downwards. “No, sir. Sorry I’m late. Are you going to... punish me?”

“Punish you?” I’d never done anything like this before, and suddenly felt completely out of my depth. I wasn’t sure exactly what she wanted, but I knew what I wanted to do. “Yes, perhaps I should spank you for such a lack of respect.”

When she looked up, she was blushing and had a fairly neutral expression on her face. But her eyes flashed with excitement. “Yes, sir,” she said enthusiastically. “And you won’t tell my parents what a naughty girl I’ve been?”

“No, not if you hop onto my lap.” I sat behind my desk, and slouched down in the chair, sliding my hips forward a bit. As I’d hoped, as she leant across me and put her hands down on the floor on the opposite side of me, my throbbing erection was pushed against her stomach. I wanted her to know the effect she was having on me.

She wiggled around on my lap.

“Are you comfortable?” I asked.

“There’s something hard pushing into my stomach, sir. Maybe I could help with that.”

“I think I’d better punish you for your lateness first.” I only narrowly resisted the temptation to give up the pretence and fuck her silly.

I lifted the back of her skirt, and admired her arse. Of course, her underwear was long gone. She had her legs slightly apart, to help balance, but the result was that I could see her pussy lips, perfectly framed by her arse cheeks. What I couldn’t see was any hair – she had shaved her lips, at least, totally bare.

I let out a low moan – amazed at the perfection on my lap.

“Are you okay, sir?” Sarah asked.

“It’s just... your ar... um... wow...”

“Please, let’s just get this over and done with,” she said, although the way she wiggled her bottom at me suggested she wasn’t offended by the remark.

I raised my hand, and gave her arse a moderate slap. I was surprised at how loud the smack was, but Sarah’s, “ooohhh” sounded like it was more pleasure than pain.

I gave another slap, and counted out, “Two.” I realized that I hadn’t even decided how many I was doing.

“Please, sir,” said Sarah, “only ten this time.”

“I think that given your flagrant disregard for uniform standards, it had better be twenty.”

I counted out each slap, alternating between cheeks, and each time Sarah moaned a bit louder, and the smell of her excitement grew stronger. At ten, I stopped briefly to stare at her inner lips, swollen and poking out from her outer lips. I could see them glistening damply, as she shuffled her thighs across each other.

“Oh god, I can’t take any more of this,” I found myself saying out loud.

“Sir?”

“We’re going to do this differently. I want you to bend over the table.”

“Yes, sir,” said Sarah, somewhat awkwardly getting up from my lap. Her skirt fell back down, just covering her arse again. She looked down. “Shall I take it off?”

“Hike it up, and bend over that table, now!” I said. I had no idea if I was still acting the role, or just desperately horny.

Sarah did as she was told, putting her head down on the table and turning to watch me. Meanwhile, I was frantically undoing my belt and trousers.

“What are you doing, sir?” Sarah asked, with wide-eyed ignorance which I thought was entirely feigned.

“You’ve turned me on so much with all your teasing, that I’m going to teach you a lesson, by fucking you.”

“Oh god.” Her voice still had a slight note of concern, but she just spread her legs a little wider.

I pulled my pants and boxers down to my knees and, with them still on, lined up my cock at Sarah’s entrance. I hesitated for a moment, briefly wondering whether I had somehow pushed her into this, but I thought this must have been what she came to my room for. All the other games were just an elaborate form of foreplay, which I was short-circuiting a little, but I couldn’t wait any longer.

And neither, it seemed, could she, as she pushed back against me. I pushed forward, and in a moment, I was buried deep inside her. The heat from her pussy was intense, and it was all I could do to fight back an initial urge to spurt inside her immediately. I had to hold myself still for a few moments.

Sarah let out a whimper of frustration. “Fuck me. Please, just fuck me hard,” she whispered. She wriggled on the table slightly, pushing one hand down beneath her to play with herself.

I knew I couldn’t hold out long, but had a sudden thought. “We only made it to ten, young lady.” I smacked her hard on the arse, with my cock still buried deep inside her.

She screamed in shock for an instant, but then moaned, “Oh god, yes.”

I counted out, “Eleven,” and then started to thrust into her.

She was moaning incomprehensively by this stage, and I was sure I was about to explode.

I think I counted ‘fourteen’ twice, as my ability to think was tested. I think it was on ‘eighteen’ that she tensed, and moaned beneath me, her pussy clamping hard on my cock as she came. I gave up all hope of lasting much longer and after two more quick, deep thrusts, pumped my cum into her.

She collapsed onto the desk in front of me, still breathing hard.

***

Soon after I had slipped out of her, the college’s mobile phone rang. The one that the duty tutor had to carry and that the students would call in case of emergency. The one that I really could not ignore.

All I could say was, “Fuck, who could that be?”

But I answered it – it was one of the first years, who had locked herself out of her room. As I got off the phone, Sarah was sitting, slightly gingerly, on the desk.

“I will be two minutes, I promise.” I finished doing up my pants, grabbed the master key, and leant across to kiss her, intending a quick peck on the lips.

She pulled me back in for a much longer kiss, our tongues gently dancing together.

When we broke contact, she simply said, “I figured our first kiss should be a bit more than a peck.”

I stared for a moment – I hadn’t even realized it was our first kiss. “Sorry. I’ll be one and a half minutes if I run up the stairs...”

***

When I returned, Sarah was crying. I also noticed that she had changed into a T-shirt and jeans, but mostly I noticed that she was crying.

She sniffed, and tried to blink away her tears.

“What’s wrong?” I asked.

“Sorry – I should just go.” Her voice dropped to a mumble as she reached for the door. “Thank you... er, oh...”

“No!” My voice was sharper than I intended. “I mean, please don’t go. Stay the night with me.”

“Sorry, I just always screw up.” She turned away from the door, but crossed her arms in front of her. “Usually, guys think I’m just into study, and reading, and stuff. Now you think I’m into all sorts of weird shit, and... and...”

“Sarah, there were two people playing our little game tonight. I’m sorry if I pushed you too far.”

A thin smile crossed her face and she shook her head. “Hang on. You think you were the one pushing? It was a fantasy I knew I had.” She looked me in the eye with an eyebrow raised.

It was my turn to blush a little.

She sighed quietly. “But I just... I just let you see too much.”

I looked down her body, and raised an eyebrow.

She smiled slightly. “Not like that – I wanted you to see my body. Well, not that I think it’s that great—”

“I do,” I added, entirely truthfully.

Sarah blushed a little, but at least there was a hint of a smile again. “I mean, I hoped... I dreamed that maybe I could finally... well, seduce you, but...”

“You did?”

“Of course. You must have noticed I was keen on you.”

“Well, I wondered once or twice. I guess I’m a bit slow...”

“You could say that!” Sarah smiled fondly at me, but then her face started to cloud over again, and she sighed. “What I meant, was that you saw too much of my dark side, or whatever you might like to call it. It was just easy to pretend to be confident, ‘sexy schoolgirl Sarah’. But that’s not really who I am...”

“Well, usually people spend a while doing it in the missionary position before exploring fantasies, but I bet everyone has them. Some of us might even have wilder ones than that.”

“Oh, anyone I know?” Finally, she unfolded her arms and smiled. “Isn’t there a rule though - ‘No spanking on the first date’?”

We shared a laugh, before I said, “Actually, technically, we haven’t been out on a date yet. Would you like to go out with me?”

“Yes, well, if you still want to. Although maybe not right now...”

“No, well, right now, I have one really wild fantasy that I wanted to tell you about.”

“Oh...kay.” There was a hesitant tone in her voice and she folded her arms again.

“It involves the two of us in that bed. No fancy dress; in fact, completely undressed. I want you to be you, and I’ll be me.”

So, that’s exactly what we did. And it was wild.

 

 

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Written by PhilU
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