tagErotic CouplingsFortune Favours The Brave

Fortune Favours The Brave

byAnnasFriend©

This is my April Fools' Day 2019 competition entry. Everybody is eighteen or older. They also exist in a completely fictional world that doesn't really bear close scrutiny. But I hope you enjoy it.

**

"No," I said firmly. "I'm not going to do it."

"But come on!" said Rory. "This is your chance for immortality! Your name will live on forever."

"So will pictures of your dick," said Jeff, helpfully. "People will be looking at pictures of your dick for like, millennia."

"Exactly," I said. "I do not want that kind of immortality. I want to be a lawyer when I get out of here. You think anybody will hire me if this kind of story gets out about me? I don't think so. Plus... I could get arrested."

"Fortune favours the brave," said Rory. "And we're offering a fortune, remember?"

"Hardly a fortune," I said. "Not nearly enough if you ask me."

There was a whispered conference between Rory and Jeff.

"All right, we'll double the stake," said Rory. "Four thousand."

I hesitated. It was all very well wanting to be a lawyer, but if I couldn't afford to stay in school I wasn't going to be doing anything except flipping burgers.

"Five thousand," I said.

"Done," said Rory, without hesitation.

Damn. I should have asked for more.

"And it has to be tomorrow night?"

"Yes. That's always been the challenge night. That night, and no other. We'll meet around two, OK? That gives me time to get a copy of the first edition."

And with that they departed, leaving me to reflect rather miserably on what I'd just agreed to.

**

I shivered in the cold. It was a dark night, with just a sliver of moon giving a small amount of light over the lawn. The hall loomed out of the darkness nearby, taunting me.

We were waiting for Rory. He was late. It was nearly three when he finally turned up.

"Sorry. Took longer than I thought. But here it is."

It was a first edition of the local newspaper, a breathtakingly dull chronicle of the minor achievements and activities of the local community. But the key thing was the date on the front. The first of April.

"You'd better get ready," said Rory.

"I've been thinking about that bit of it - can't I take them with me?"

"Nope. That's not the challenge. You have to be all in -- no changing your mind half way through me."

Reluctantly I stripped off my clothes, put them in a bag, and handed it to Rory. All of my clothes.

"Take these."

He handed me two little blue pills and a bottle of water. I swallowed the pills, took a swig of water, and handed the bottle back.

"Probably be about thirty or forty minutes before they work."

I nodded.

"Good luck. Got the phone?"

I held it up to show them.

"Good. Sun comes up around five thirty. We'll be waiting here. But if you're not here by six, we'll have to go. Can't risk being spotted. But we'll leave the bag here."

They both shook my hand gravely. I felt like an Allied agent about to be parachuted into occupied France. Then I took a deep breath, and began to slowly walk towards St Agatha's.

Fortune favours the brave, I told myself.

When I turned around and looked back they had been swallowed up by the shadows.

**

St Agatha's was by far the most traditional and conservative of the eight colleges that made up the university. It was still women only, for one thing -- two hundred of them. All lights had to be out by eleven, for another. Men were not allowed to stay on the premises after 9pm, and indeed no men were allowed in any young ladies' room unless the door remained open. It might be the twenty-first century, but St Agatha's was quite happy staying in the nineteenth, thank you very much.

And I was about to break into it, in the dead of night, naked, and take at least half a dozen photographs of me in different and recognisable parts of the college. With the newspaper as proof of the date, just like in hostage photographs.

That was how the rich young men of neighbouring St Luke's amused themselves, by devising April Fools' challenges and pranks like this and then kicking in the money to find some poor sap desperate enough to undertake them. Last year an unfortunate individual called Eustace Harris had climbed to the top of the college spire stark naked. Unfortunately, there his nerve had deserted him, and the fire brigade had to be called to get him down. Eustace was sent home in disgrace and had not been heard of since.

Sorry, did I say the photographs had to be of me naked? That wasn't quite the whole story.

I also had to be fully erect.

**

I had been promised that a corner downstairs window of the library would be left unlocked. They had somebody on the inside, they assured me. That would be my point of entry. As I slipped along in the shadows, teeth chattering, I rather hoped whoever it was had forgotten or changed her mind. Already I was regretting this. Five thousand wasn't enough. Hell, fifty thousand wasn't enough.

But a window was open. I could see a small gap at the bottom of it. I reached over and gingerly raised it. It squeaked noisily and continually as it slid upwards. I froze. I expected to hear the barking of dogs, the wail of an alarm, floodlights clicking on, jackbooted soldiers with rifles running towards me...

I waited. None of those things happened. I breathed again.

The good news was the window was open. The bad news was that I now realised that clambering in would be no simple task. There was a hedge running along the outside of the building, just below waist height, and to get in I would have to get over that and onto the window sill. If I'd been clothed it might have been an awkward few moments, no more, but to do it naked without any injuries or scratches... that was a more formidable challenge.

I placed the phone on the ledge and tossed the newspaper through into the dark room beyond. Then I lifted one leg up and managed to get that onto the window sill. I grabbed one edge of the wall with one hand and tried to pull myself up with sufficient clearance to avoid any potentially unpleasant contact. But it was just too much of a stretch. I found myself stuck with one leg on the window ledge, the other still on the ground, and my groin precariously placed about an inch above some rather unfriendly looking hedgerow. If I'd been found at that moment it would have looked like I was trying to commit an indecent act with the shrubbery.

I cursed the college gardeners. What a stupid place to have a hedge.

I tried bouncing the one leg that was still on the ground a few times. Perhaps I could generate sufficient momentum to rocket myself through.

"One... two.... three!" I muttered to myself. And on the three I sort of launched myself sideways and up and through the opening. Something sharp and thistly scraped against my testicles. The top of my head made violent contact with the bottom of the window. My knee banged violently against the wall and then I hit the stone floor, hard. No carpets for St Agatha's. Of course not.

I spent several moments whimpering to myself and checking my nether regions for any signs of permanent damage. There seemed to be none, though I did feel what felt like some nasty bloody gashes on my inner thigh, perilously close to my ball sack.

But amazingly, when I returned my attention to my surroundings, I found that I was, indeed, inside.

**

You have probably never found yourself naked in the middle of the night in the dark library of a young ladies' college. I decided I didn't like it much. It was extremely tempting to find an exit, chuck the phone into the middle of the nearest lake, and head for home.

But still... I was here now. And five thousand would make a big difference. If I was quick, and lucky, perhaps I could get all this done in less than an hour.

I retrieved the phone and the newspaper. Would the library suffice as my first photo opportunity? I decided it would. The lending desk was the obvious place. I made my way carefully through the maze of desks and book stacks towards the front of the room. I sensed the ghosts of generations of former students looking down on me in stern disapproval.

I reached the desk. It was broad and expansive and looked ideal. I arranged a few items for authenticity -- a finger-wagging sign about fines for overdue items, a small stack of books from the returns trolley. Then I laid myself along the table, arranged the sign and the books and the newspaper, and turned on the camera.

It automatically turned on the light, of course, and I was momentarily dazzled by the brightness. I fiddled with the camera and put it into "selfie" mode. Then I tried to get the shot perfectly lined up. I needed the newspaper in the shot and it also needed to be recognisably the library. And it needed to include my cock, in case you've forgotten that key piece of information. And I was also very keen that my head should not be visible.

It was unbelievably difficult. The only solution I found in the end was to position the newspaper over my stomach and put the sign between my legs. I moved the camera carefully, looking at the screen to make sure everything was just right... perfect!

No. I realised it wasn't. One key element was not in place.

I blamed the cold.

**

I don't know about you, but I've always preferred masturbating in bed. Or perhaps on a couch. At a push, some carpet will do. The point I'm making is I like to be comfortable, and ideally warm. I am easily distracted by any kind of discomfort when trying to focus on my sexual pleasure. Male readers would probably also agree that once you start to worry about not becoming erect, the chances of you becoming erect plummet to effectively zero.

I lay on the cold, unyielding lending desk of St Agatha's library, cock in hand, frantically pumping myself up and down and trying to summon up some favourite erotic memories that would help me along. Surely the Viagra would kick in soon? I thought about Julie, the Canadian exchange student who'd sent me such dirty messages before her arrival the previous summer and then, tragically, had to cancel her trip. I thought about Mrs Cole, the pneumatic wife of one of my father's friends who'd once cornered me at a family barbeque and ten minutes later was sucking me off in the bathroom with surprising skill and efficiency. I thought about Kryssie, the bookish neighbour's daughter who'd surprised and delighted me with her unexpectedly luscious body and her relentless enthusiasm for screwing...

... and still nothing. What the bloody hell was I going to do? From my vague knowledge of Viagra, it only worked if you gave it a head start, so to speak. Once the blood was flowing to the right places, it kept it there. But what if the blood never made it to the right places? I wondered if I could just do photos with my cock in its flaccid, unimpressive state. It wasn't what we agreed, but perhaps they'd decide it was worth a couple of thousand at least. But I suspected they wouldn't. Those guys didn't like compromises. Also, I wasn't sure I wanted my cock to be immortalised like that. I mean, I wasn't massive when erect, but I wasn't bad. What I had at the moment was laughably tiny, more like a baby monkey's penis than that of a supposedly virile nineteen-year-old.

I groaned to myself and redoubled my efforts. I thought about my come dribbling down Mrs Cole's chin. I thought about Kryssie with her long and perfect teenage legs wrapped around me, panting about how much she just absolutely loved fucking. I thought about some of the pictures Julie had sent me.

Not a twitch.

Dammit fucking fucking bollocks fuckit.

A voice came out of the shadows.

"Do you need help with that?"

**

I jumped so much that I promptly dropped the phone and fell off the back of the table, dragging various items with me. I landed heavily on my shoulder - the same shoulder which had taken the brunt of my landing in the library - and I yelped in pain. A second later the overdue books sign landed on my head, proving surprisingly sharp and only narrowly avoiding taking out an eye.

A second or so later the newspaper fluttered down and diplomatically covered my groin.

I lay there, groaning quietly. There was the sound of light footsteps. My phone was picked up and the light created mocking, flickering shadows around the hall as its new owner made their way around the table to where I was.

I covered my eyes as I was illuminated.

"You're bleeding quite a lot," remarked the voice.

"Can you turn that off?" I said irritably. Clearly my night was over now. The police would be called, the college authorities, perhaps even the local press -- though I doubted my story would make the front cover of the newspaper currently enveloping me. They preferred cattle shows and charity gala evenings to perverted young men breaking into respectable girls' colleges.

The light moved away from me and my night vision began to slowly return. All I could make out of the person holding the phone was they seemed to be wearing some kind of dark dressing gown. Probably about five foot six. The voice had been unmistakably female, and probably quite young.

"Rory said you were a bit of a long shot," said the voice. "He said he couldn't see any way he was going to have to pay out the money, but it might be worth it just to see what kind of a mess you made of it."

Well, that was cheering. I made a mental note to shoot Rory next time I saw him.

But... if she knew Rory, perhaps I wasn't completely doomed.

"Are you... their inside person?" I asked. "The one who opened the window?"

I could just about make out her nodding. "God, you made so much noise getting in! I felt sure the whole place was going to wake up."

"It's harder than it looks," I said defensively.

The voice giggled. "Yes... perhaps not the best choice of words at this precise moment."

"It's not normally a problem," I said, a little huffily. "It's just... these are quite unusual circumstances."

"Indeed," said the voice.

I found her slightly mocking tone quite annoying. "Look, perhaps if you'd like to leave me to it, I can still get on and finish this stupid challenge. Thanks for leaving the window open -- and I'll try to make much less noise getting out."

"But what about your, um... dick?"

"I'll be fine."

"You didn't look fine. You were trying to whack off for five minutes and it was still like a piece of string."

"You were watching that whole time?"

"Of course. Wouldn't you? If it had been the other way around?"

I supposed she had a point. Still, it seemed rather unfair somehow.

"I'm sure I'll get everything working, thank you. I just need to find the right... stimulus. Like jump-starting a car, you know?"

"Hmm." The girl seemed to be thinking.

I poked my uncooperative cock again, but more out of hope than expectation. She focused the torch on my groin and we both regarded my limp member.

If anything, it seemed to have got smaller.

"The sooner we get you out of here the better for both of us," said the girl, briskly. "So - how about if I show you my tits?"

I did a double-take. "Sorry... what did you say?"

"I can show you my tits. If it'd help. No touching, but... you can see them. I think they're supposed to be quite nice. The other girls say they are, anyway."

I paused. Clearly I hadn't reached the end of my surprises for the night.

"OK," I said. "Let's try that. And, er, thank you very much."

I lifted myself up from the floor, clutching the newspaper over my crotch. Then I realised it was probably a little late to be bashful. I limped back around to the front of the lending desk. The girl followed me.

I rearranged myself on the desk. The phone torch illuminated me, and I lifted up my hands to shield my eyes.

"I need to see you," I said patiently. "Not much good if the torch is on me, is it?"

There was a slightly nervous giggle. "Oh yes. Sorry. Here -- you hold it."

She passed me the phone. I turned it on her, but angling it down to stop it from going directly into her eyes.

For the first time I saw her properly. I guessed she was a little younger than me, perhaps eighteen. She was dark haired, with shoulder length bobbed hair framing a very pretty, mischievous face. She was wearing a heavy dressing gown that made it very hard to see much else about her, but from the way it swamped her frame I guessed she was quite slender.

She took a deep breath. "Gosh... I've never done anything like this before."

"Me neither," I said, feelingly.

Another deep breath, then she undid the dressing gown and shrugged it off, placing it carefully on a nearby desk. Now she was just in a simple sheer white nightdress with shoulder straps. Her body looked supple and firm and lovely. It gave me hope.

She composed herself again. "Here goes!"

She slid one strap off a shoulder, then the other. Then she slowly tugged it down, revealing a pair of full, lovely breasts topped with slightly puffy pink nipples.

"They were right," I said reverently.

She frowned. "Who were?"

"The other girls," I said. "Your breasts are lovely. And you're... well, beautiful."

"You really think so?" She blushed slightly.

"Absolutely," I said.

"Oh... thank you, that's really nice to hear. Now -- you'd better... start, hadn't you?"

"Er, yes, right," I said. "Good point. Do you think you could... move just a little closer?"

She shuffled forward half a step, no more. Obviously I wasn't completely to be trusted.

I reached down and gave myself a hopeful tug. This would surely get things started. I looked at her chest again. Still breathtakingly gorgeous. Then another tug.

"Oh dear," said the girl.

"Just a minute," I said through gritted teeth. "I'm sure.... Any second now."

But my cock had other ideas.

"Not that lovely after all," said the girl sadly.

"It's not you," I said. "It's me... it's just... thinking about it too much. I'm sorry. I think I should just give up and go home."

"I'm sorry too," said the girl. "But perhaps you're right." She seemed to have warmed to me slightly. "Though I really think we should clean up those scratches before you go though. There's a first aid kit around here somewhere."

She vanished off into the darkness for a few moments, returning with a small plastic box. She brought it to the table, popped it open and rummaged around in it. She'd pulled the straps back up and those glorious breasts were regrettably covered from view again, though I was very aware of them swaying beneath the cotton material just a few inches away from me.

She peered at my various wounds. My shoulder was bruised but there was no bleeding. That was more than could be said for my knee and the cut at the top of my inner thigh.

She examined my knee first, and tutted.

"It's quite deep," she said. "It needs a bandage or I'm afraid it's just going to keep bleeding. And we don't want to leave too many DNA clues, do we?"

I agreed this would be a bad thing. She rummaged in the first aid box.

"You'd think there'd be some bandages," she muttered. "But there seems to be nothing but plasters and tape and some cream."

"I'll be fine," I said bravely.

"No, you really need a bandage. There must be something we can use. Yes -- of course. Be right back."

She darted away into the shadows again. I waited gloomily for her return, watching my blood drip slowly onto the stone floor. I heard some rustling sounds.

A few moments later she was back, slightly pink faced I thought, and brandishing a small handful of white cotton.

"These'll do," she said. "But you owe me a pair of knickers."

She knelt down in front of me and, using the tape and her underwear, did a very respectable job of bandaging up my knee. I was very aware of her head being so close to my crotch, but my crotch still seemed stubbornly oblivious.

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