Risk Taker

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Status: In Progress  |  Genre: General Erotica  |  House: Stripping and Humiliation

The risks of taking a risk

They say that if you want to feel superior to your boss when talking to him the best thing is to imagine him in the nude, completely in the nude that is, not a stitch on.  Imagining him in the nude though, that’s not much fun.  Actually seeing him completely in the nude without a stitch on, that’s much better.  You find out that he has secrets you never dreamt of.




It was one of those things the company had decided would be a good thing.  It was always having these bright ideas, dredged up by some management consultancy somewhere no doubt.  Smart objectives, matrix management, client investment and so on and so on.  It never did any good, but it didn’t stop them.  The next bright idea was Bonding Weekends.  Ha ha!  The girls said.  Bondage weekends, in your dreams!  But of course it wasn’t kinky bondage they meant, it was a weekend for staff to bond.  To get to know each other, to develop a rapport.  We had to see each other as a whole.  That was the idea of my Boss Monica anyway.  She was always saying she liked to see men as a whole.  She was a very forceful woman.


"When shall I arrange the Bonking Weekend for?"asked Tracey, my secretary.


"Freudian slip," I said, "I think you mean Bonding Weekend!"


"I know what I mean," said Tracey, "everyone bonks each other silly the whole weekend.  If the high-ups only knew what goes on!"


"Well there'll be none of that on our weekend," I said.  There was only me, and the eight girls who worked for me, and it wasn’t as if I was going to be bonking anyone.  


"Chance'd be a fine thing," said Tracey.


No, no chance of a bonk for me.  It didn’t stop me thinking about it though.  There's nothing wrong with that, is there?  Nothing wrong with fantasising about which one I would bonk if I got the chance.  Of course I never would get the chance, I was far too shy for that.  Eight girls in the department and I would of course have willingly bonked any of them but...  


Tracey arranged the weekend. She was good at that sort of thing - arranging weekends I mean, not bonking, I mean she was probably a good bonk, she certainly looked the sort,  but I mean she arranged the weekend.


"It’s at The Grange," she said, "nice rooms, good conference facilities.  I’ve arranged for you to give a keynote speech on the Saturday."


"Oh.. um..." I said.  I’m not very good at speeches.


"Don’t worry.  I'll write it for you.  I know how busy you are."


"What do we do the rest of the time?"


"Oh, there'll be plenty of time for bonking, don’t worry..."


"I wasn’t meaning..."


"Oh yes you were...  I can see you’ve got your eye on Sharon."


Sharon.  Sexy Sharon of the short skirts and big tits.  Reckoned to be the office bicycle, ridden by everyone except me.




"No buts, she likes a man with a big one..."


"But I don’t.."


"Don’t you?  I’d have thought a man like you would have..."


"I don’t mean that..."


"You mean you have got a big one!  I thought as much."


"I meant...  I meant..."


"Well, come on, how big is it?"


"It’s...  its..." what on earth could I say?  Tracey had a way of teasing me like this and I always fell for it, "its.. average...  I think.." I said lamely.


"Average?  You think?  You don’t know?"


"Well....  I...". I couldn’t think what to say and was blushing furiously.


"Well why don’t you show me?  Demonstrate?"


"I can’t do that!"


"Why ever not?"


"Well..  I wouldn’t be right.  It wouldn’t..."


"Wouldn’t what.  What’s wrong with a man showing a girl his...  what should we call it...  wit, intelligence, startling personality?"


"Oh..  that...  I..."


"Why?  What did you think I meant?  You didn’t think...  yes you did!  Naughty boy.  Well I’ll let Sharon know yours is average.  Might be enough.  You never know."


And she went off winking.  She was always teasing me like that.




He'd said he’d got a 'average' one, whatever that meant.  I’d wheedled that out of him.  It was fun teasing him like that, he was just so teasable, and so easy to manipulate as well.  Hadn’t a clue really, so I’m not sure How he'd ever got to be the boss, licked arse probably.  I mean I did all the work after all, and doing all the work I  deserved some reward.  The reward I gave myself was to tease him, unmercifully.  And as for the Bonking Weekend, a golden opportunity to tease.  I mean that was the whole point.  Bonking Weekend indeed!  Nobody called it that, but it was a good tease.




I’d written quite a good keynote speech.  Tracey had had a hand in it of course, but I had polished it up.  It had just the right note I thought for out department.  The girls listened attentively, though the giggling from time to time was a bit distracting.  I mean there was humour of course, but I’m not sure if giggling was appropriate.


It was entitled 'Who Dares Wins'.  I explained how I had reached my position by not being afraid to take risks.  I didn’t get where I am today," I said, summing up, "by taking the safe course.  I dared...  and I won!"


The girls were suitably impressed, especially Sexy Sharon.  She put up her hand.


"Are you really somebody who would take a risk," she said, "I mean I like a risk taker, but you always come across as the cautious type."


Sharon liked a risk taker!  Bonking Weekend and Sharon liked a risk taker.  In truth she was right.  The speech was for the girls' consumption.  I never took a risk in my life.  I didn’t get where I was by taking risks, I got there by dedicated arse licking, mostly metaphorically of course, the speech was just to make me look good in front of the girls.  But Sharon liked a risk taker and it was Bonking Weekend.


"Absolutely," I said.


"You get a kick from risk taking?  I mean you come over as a bit of an arse licker...  " she added.


I blushed scarlet, but I had an answer to that one.


"Other people," I said, "Can lick my er...  arse."


"Ooooooh," said Sharon grinning, "promises, promises!" I’d made an impression there.


I was just about to impress Sharon a bit more when a young slip of a girl barged in with the tea things.


"Do you mind," I said to her rather sharply.  It’s best to let servants know there place isn’t it, "I was just impressing the girls...  I mean I was just impressing on the girls the importance of risk taking."


"Well you’re taking a risk now if you don’t stop for tea now, coz if you don’t I’m taking this lot back."


Cheeky thing.  I gave a scowl.


"You should know your place young Miss," I said, "I've a good mind to report you to the management."


"Don’t mind him," said Tracey, "he’s in charge."


"Him in charge?" said the girl sneering.  What sort of staff are hotels employing nowadays!


"I am in charge, and more word out of you and I'll show you my..."


"Your what?" She sneered standing hands on hips.  Stupid girl.  There was only one word for her.


"Arsehole," I said.  Strong language but she deserved it.


"What!  Show me your arsehole.  That would be a real treat."


"Yes..." I said...  "No...  I didn’t mean...I meant..." I had been going to say "...my way of dealing with people like you" but all the girls burst out laughing and before I could say it she marched out.


"Chance would be a fine thing..." she said and left me spluttering red faced.




Of course he hadn’t a clue what to put in his speech, but I knew exactly what I wanted him to say.  I mean I had to back him into a corner, one he couldn’t get out of without losing face.  I’d already dropped the hint that he might get a bonk if he impressed the girls, and I’d written a speech which he would think made him look impressive.  After all, above everything else he was a show-off.  He loved to show-off in front of the girls and this set just the right tone for a show-off.


And he’d fallen for it.  Set himself up as the great risk taker.  And Sharon had pushed him just far enough.  He was going to have to take a risk or lick arse, and I reckoned I knew just which one he’d choose.




"Great speech," said Tracey, "Coming to the party tonight?" 


"Party?  What party?"  I didn’t know anything about a party.


"It’s Bonking Weekend,"said Tracey, "there’s always a party.  How do you think people get the excuse to bonk?"


"But just me and eight girls...  I mean..."


"Don’t look so worried.  You won’t have to bonk everyone..."


"I didn’t  mean that..."


"Just teasing," said Tracey, "it’s just a party.  A few drinks.  A few naughty games - wink wink.  We'll all be there.  Including Sharon...  she was impressed you know."


"Was she?"


"She likes a risk taker," said Tracey winking.  I didn’t know if she was still teasing or what, but I felt my face go all red anyway.


Sharon would be there!  Naughty games!  Oh my gosh!


"Right," I said, "what time?"


"Ten o"clock.  Room 243."


"Isn’t that the Luxury Suite?"


"I believe it is.  Must have got an upgrade."


"Oh," I said.  I should have had the upgrade not Tracey.  I had an attic room on the fourth floor.




We were all waiting for him in my suite when he knocked on the door.


"Come in.  Come in," I said.


He stepped in nervously carrying a bottle of wine.


"Oh, Prosecco," I said, "never mind, we’ve ordered half a dozen bottles of champagne."


"Is everyone here?" he looked round quizzically.


"Don't worry.  You’ve got your choice of the girls," and I gave him a conspiratorial wink, just so he wouldn’t know if I was teasing or not.


"Oh," he said, “I see..." though he didn’t.  Not at all.


"Right," I said, "Play time girls.  The first game.  The Big Risk Game."


"Big Risk?" he swallowed nervously.


"Yes, you said how you liked taking risks.  So here's a game.  It’s a variant of the three card trick."




"Yes, simple really.  Three cards.  One of them is the Ace of Spades.  If you pick that one you..."


"Yes, I know, I have to pick the ace to win..."


"Not in this version.  If you pick the ace you lose.  Only a one in three chance of losing."


"Um... well... I er..."


"You said you were the great risk taker and you won’t even play with a two to one chance of winning?  What do think of that Sharon?"


"Told you he was an arse licker," said Sharon, "a real toe sucker."


"Perhaps you’d prefer to suck my toes?" I said.


"No...  no..." he blushed bright red.


"I've got bare feet.  You can give them a good suck..."


"No... no... I'll play."


"Good boy.  Now what do you think would be a good stake?"




"Of course.  There has to be a risk.  Not much of a risk taker if there’s nothing at stake is there?  You did tell Sharon you were a risk taker didn’t you?"


"Of course.  Yes..   perhaps er...," how much could I risk, "er...  five pounds..."


"Five pounds!  That’s no risk.. .  I mean a real risk...  something that will cause the loser real embarrassment...  I know...  loser takes all their clothes off!"




"Loser strips naked.  Spends the rest of the evening in the nude.  That’s the sort of risk a real risk taker would take!"


"But really...  I mean I don’t think I can..."


"You mean you’re not willing to take the risk.  After that speech..."


"Yes...  the speech... but..."


I took him aside and whispered, "You could always tell them I wrote the speech," I said, "you could explain that you're just a stick in the mud...  what did Sharon say... arse licker.  Tell you what though.  You get down on hands and knees and suck my toes, and I’ll get you out of it."


"But I can’t..." he blubbed.


"What?  Take a risk or suck my toes?"


"Take the risk?"


"Of course you can.  It’s only a one in three chance. .


"But...  But..."


"Or get down in all fours and start sucking.  The girls will enjoy watching that...   Girls..." I said out loud, kicking my shoes off, "instead of taking part in the game he's going to..."


"No no..." he said, "I'll take part.  I'll take part."


I knew he would.  And he might get to suck my toes still.




The girls were all there.  And they were going to play party games explained Tracey.  Naughty party games.  She hadn’t been teasing.  They really were going to play games.  She suggested a sort of three card trick.  The loser was to be naked, yes completely in the nude, for the whole of the party.  It seemed well a bit risky to me, but of course I had said I was a risk taker in the speech, and then Tracey had said I should Well... suck her toes instead, so I agreed to take part.   Couldn’t be seen to be a prude could I?  I mean suck her toes, I couldn’t do that could I?  


Tracey set out the cards.  


"Do you know which one it is?" I asked.


"Of course..."


"Well...  er..." despite the fact that the odds were in my favour my heart was beating ten to the dozen, "that one...".  I looked a Tracey's face.  There was a smile...  No!  She was smiling!


"That one!" She grinned.


"No...  I meant that one..."


"This one...."


"Yes...  I mean no...  I mean...  this one... definitely this one..."


"I tell you what!" said Tracey, "I'll help you out.  This one isn’t the ace..." and she turned the middle one over.  The four of diamonds."


"Now... do you want to change your mind?"


"Change my mind...  I er..." then I remembered, it was in that book I read.  It was always better to change!  You always won when you changed...  it had been on some old TV programme with goats and cars and things.  Tracey wouldn’t know that, only being a secretary, she'd played right into my hands.  "Yes, I'll change," I said, "that one.  Definitely that one."


Tracey turned it over.  It was the Ace of Spades.




He looked like a frightened rabbit in the headlights.  Of course he'd lost.  You could fool him into anything.  Candy off a baby!


"Off, off, off..." chanted the girls.


"Strip naked or go on...  suck my toes if you'd rather," I said.  I mean I’d never really meant for him to strip naked, I just fancied him down on all fours sucking my toes.


"But..." he just stood there blushing scarlet.


"Right!  Bare feet for you," I said.  He still stood there petrified.  It was the golden tease of all teases.  He wouldn’t strip naked of course, but he was going to have to lick my bare feet to get out if it.  The girls would laugh about it for months.




I looked at the card.  How had I lost.  Surely I'd been certain to win...


"Off, off, off..." chanted the girls.  My face was burning.  My head was in a whirl.  I couldn’t think.


"Bare feet for you," said Tracey.


Bare feet?  What did she mean?


"Bare feet, bare feet, bare feet..." chanted the girls.


Bare feet...  I had to have bare feet...  


"Yes...  yes..." my head was still spinning.  I took off my shoes and socks and stood there barefoot.  There was a moments silence.  Then Sharon started up...


"Bare chest, bare chest," and the others joined in, "bare chest, bare chest..."


I took off my shirt.


"Bare legs, bare legs..."


And before I knew it I was standing there in my underpants.


"Off...  off...  off...". I didn’t know what to do.  I just stood blushing and trembling.  I couldn’t take off my underpants.  They would see..  would see... it...


What should I do...  what should I do... "Off... off... off...". The chanting got louder and louder.  And I just stood there petrified as Sharon came and she...


And I could do nothing to stop her.




 I hadn’t reckoned on the sheer force of the willpower of a group of girls when they have the bit between the teeth.  He had taken his shoes and socks off.  When I said bare feet for him I had meant for him to lick my bare feet, but he had taken off his shoes and socks.  And when the girls had seen that they scented weakness, they weren’t going to let him get away with that.  Now he stood there in his unders, red faced and trembling.


"Off... off... off..." chanted the girls, and they weren’t going to stop till they’d seen everything.


It was inevitable.  I knew it, the girls knew it, and he knew it.  I’d only meant it as a tease.  I’d never meant him to actually strip naked.  On the other hand nobody had made him.  He’d taken part voluntarily, he’d taken his clothes off voluntarily, and after all he was a show off.  It was a fitting punishment for a show-off.


He stood there in his underpants petrified.  And then Sharon walked up to him.  I didn’t stop her. I should have done, but I didn’t.  I thought he would stop her but he didn’t.  He didn’t stop her.  He didn’t do anything as she got hold of his pants and pulled them sharply down to the ground.  Oh my gosh!  Didn't he know what average was?  Hadn’t he ever measured it?  It wasn’t average.  It was the biggest I’d ever seen!


And under the end of his penis was a small brass ring.  He’d had his cock pierced.


Who'd have thought it!




What had I done.  My mind had been in such a whirl since the girls started chanting.  And now they were laughing and I was standing there with no clothes on.  It was then that the embarrassment hit me.  I had no clothes on and the girls in the office were all looking at me.  My face was burning and I stood frozen to the spot, completely nude, my penis with... with...   Oh why had I had that done!  All could do was let them look and laugh.


"How...  why..." asked Tracey.


"It was last year..." I gabbled, "when I was on that business trip...  you know the one..."


"I thought you were wriggling about a bit when you came back..."


"I went for a er..."




"I mean massage..."


"That’s what you get up to is it!"


"No...  I thought it was all respectable and...  the girl said I had to take all my clothes off...  and she said I had a big one...  and I did I want er... a...  er...


"Wank?  You thought you were going to get a wank!"


"Well...  I suppose so... but she said I should have one of these.  She said it would...  would..."


"Improve your performance?"


"Er..  well... I suppose so."


"And does it?"


"I don’t know.  She..  she..."


And the girls started laughing again and my face was burning.


It was then that the knock came on the door.  I looked at it in horror.


"Well go and answer it then," said Tracey, "it'll be the champagne we ordered."


"But I’ve got no clothes on," I whimpered, "can I put my clothes back on please."


"Of course not.  Naked for the whole of the party.  You're our naked slave.  That’s the whole point of the game.  You took the risk.  You lost.  And now you have bear the consequences."


"That’s not all he’s bared," chortled Sharon.


Knock at the door again.


"Go on," said Tracey, "or have you forgotten the meaning of the word slave?"


"But they'll see me with nothing on."


Sharon spoke up, "That is the whole point.  To cause maximum embarrassment. Go on...  obey your Mistress."


Sharon knew how to get me really obedient.


"Yes Mistress," I said and with the girls' laughter ringing in my ears I crept to the door and opened it.  I peered out.  A girl was standing there with a trolley on which were four bottles of champagne and eight glasses.  The same girl who had brought us tea during the meeting.  The one I’d had to be a bit sharp with for interrupting us.


"Well, open the door wide," she said, "I’ve got to push this in."


"But...  But..."


"Well go on then," she stood with her hands in her hips, "I haven’t got all day."


"Yes Miss," I opened the door and she flounced in.  


She looked at me and a broad smile appeared on her face.


"Ooh!  Have I come at an awkward time," she said.


"Not at all.  I just thought that show-offs should be taught a little lesson," said Sharon.


"A little lesson in what?"


"In humility.  He doesn’t want to be quite so much of a show off when he's got no clothes on!"


"You’re right there," said the girl, "he looks really embarrassed."


"That’s the whole point.  Go on.  Have a good look."


She walked round me looking at every inch of my body while I stood there completely nude trembling with embarrassment.


"Well you’re a dark horse," she said, "never thought you’d have one of those."


"Hidden depths," said Tracey, "he was about to tell us what happened after he had the cock ring fitted."


"You say he needs to be humiliated?"


"Well, I said humility, but don’t let me stop you."


"It’s just," said the girl looking at me with her hands on her hips, "this little show-off reported me to the management.  Showed me up in front of everyone.  So do you know what I’m going to do?"




"Show him off to everyone.  With no clothes on.  A suitable punishment for a show-off don’t you think."


I should have done something.  But I had nothing on.  I was in the nude.  A naked slave.  I couldn’t resist.  I just couldn’t.


"You know why men get those things?"


"To show off?"


"It’s like a bull with a ring through its nose."


"A what?"


"You can lead a bull anywhere  by the nose.  Just tie a piece of string to the ring."




She moved up close to me.


"You can lead a man anywhere by the cock ring.  I bet she did this..."


I felt a tug on my penis.  I hadn’t even noticed her tying the string on.




Honestly!  Why do men do these things.  We wheedled it out of him eventually.  He’d gone to this shady massage parlour, he might have pleaded innocence but we know better, and the girl had persuaded him to have a cock ring.  It’s an old scam.  She'd leashed him with a piece of string and threatened to pull him out into the street if he didn't pay up.


And now he was at the mercy of the hotel girl.  Well he deserved it didn’t he?  For being such a fool.  He deserved a little punishment.  She'd fastened a length of string to the ring and was tugging on his cock.


"Come on... round the room with you..."


She tugged his cock and he followed.


"Yes Miss..."


"Faster, faster..."


"Yes Miss."


It was the funniest thing I’d ever seen.  She tugged him round and round the room, faster and faster, and he pranced after her, holding onto the string trying to prevent his cock being yanked, his cute little bottom wiggling as he ran.


How we laughed!  Our little tease had developed into something much more... well... stimulating.  But even more was to come.




"Open the door," she shouted, tugging on my willy again.


"You can’t pull him round the hotel!" yelled Tracey.


"Oh yes I can.  He got me sacked, so I’ve nothing to lose.  Along the corridor!"


"In that case..."


The ring was fixed through my penis in the underside just below the head.  The girl doing the massage had pinched the skin so as I didn’t feel it being inserted and once it was there she said I would have to pay or be pulled out into the streetand now...  oh no...  the door was open and I was being pulled through it...


Along the corridor being pulled by my willy with nothing on.  What if someone should come!  What if someone should come!


"Please Miss.  Please..."


But she was merciless.


"Faster, faster..."


"Yes Miss"






"Prance.  High stepping."


"Yes Miss."


And I pranced.




She was merciless.  Up and down the corridor in the nude.  And he had no choice.  When you have a man by his cock he's at your mercy.  And back into the room.


"Please..." he said, "I'll do anything."


"I know," I said, "down on all fours and suck my toes."


"Yes..  Yes..." and before I knew it he was on hands and knees, bottom high in the air, my big toe in his mouth.




I sucked and I sucked.  I had to.  It was the only way.


"Well he keeps his promises," the cheeky hotel girl was sneering again.


"His promises?" said Tracey.


Oh no.  I was on all fours, bottom high in the air.  I knew what she was going to say.


"He promised he'd show us his arsehole.  And I must say.  A very nice one it is too."

Submitted: February 03, 2020

© Copyright 2021 Joex. All rights reserved.

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