The Resort-Initiation

This is a different sort of story. Please let me know if you like it. If you do a sequel may follow.

Two owners of the resort were talking.

"The new waitress Jenny is even more of a promiscuous slut than I hoped. Last night she fucked 2 men. Jason from the band stood her against the storeroom wall during interval, one of their roadies had her in the men's toilet".,

"Which is Jenny what does she look like?"

"She's blonde no more than 20, pretty, with a slim nicely shaped body, huge tits usually has her blouse half undone to show them off."

"Alright so she's a bitch on heat but is she ready for what we want, can we use her to make money. How far will she go? You know our plans we are already making a good deal from the girls who put themselves out for little holiday parties. Is she ready for this?. Maybe we could get a few fellows, have this girl or one of those we've already broken in dressed up in uniform and left handcuffed over a chair for a good caning first. The opportunities."

"Leave it to me."

It was two nights after that conversation and Jenny was bored and more than half drunk. Her night off and in the staff amusement room there were only five stupid boring men who she'd never seen before and never wanted to again and one of the resort's supervisors Caitlin a fat low class big auburn haired bitch about 28 years old. Caitlin worked out with weights every day. Caitlin bossed Jenny around never missing a chance to humiliate her, to force her to do something dirty such as cleaning the toilets. Jenny hated her but was more then a bit scared of her.

Tonight Caitlin seemed high on some drug. Perhaps thought Jenny she'd drunk too much. Whatever it was, Caitlin was very excited. She was talking to the two best looking guys there, though Jenny thought that wasn't saying much. "Muscle bound idiots" she muttered. The two men were tickling Caitlin, trying to touch her breasts giving her little kisses. Caitlin pushed them away every so often but she was laughing along with them.

Jenny turned back to play pool. She heard Caitlin giggle and looked up to see her sitting on one man's lap. The man's hands were disappearing inside Caitlin's sweater. Caitlin said "No Troy don't do that, you naughty boy, we've got company" but made no attempt to stop him.

Jenny finished her game and glanced at Caitlin now sitting on one mans lap his hands under her tight sweater, one fondling her big breasts, the other slowly slipping down between her fat thighs. While being worked over by this man, Caitlin had taken off the second man's shirt and unzipped his jeans and was rubbing his cock with her hands.

To torment the other three men Jenny had removed her bra in the ladies toilet and undone most of her blouse buttons. Her tits almost fell out of the blouse each time she bent forward to play a pool shot. She knew that three pairs of eyes focused on that display. "Let the jerks look" she thought "that's all they'll ever do. Never a feel much less a screw" She looked at Caitlin who was spreading her legs as the man on whose lap she sat slipped his hand inside her panties.

Caitlin gasped "Oooooh, that feels so good Troy" as he rubbed her clit till her cunt was sopping then repeatedly stabbed her cunt with three fingers while still rubbing her with his thumb. Panting for breath the fat slut spread her legs wider yet and moaned "Ooooh, ooooh, yes, yes, finger fuck me Troy fill me, ooooh yes, Wayne come here so I can suck you off"

Jenny stared in disgust muttering "At least I've got a body worth men seeing and feeling unlike that tub of lard, Caitlin. Doing her best to get a gang banging. Not that I'd mind that with a few hunks"

Wayne, the man Caitlin had been masturbating moved, pulled off her sweater and undid her bra. Freed from their constriction Caitlin's breasts fell forward into the waiting mouths of the two men. Caitlin moaned and shuddered, her hands groping for Troy's cock, pulling it free of his trousers. Wayne's hands groped under Caitlin's skirt till he too found her cunt taking turns with Troy to finger fuck her. Caitlin's eyes glazed, her head rolled back, her mouth hung open her body shaking as she stroked a cock with each hand. Her skirt rode up showing all in the room Wayne's hand holding her panties down as his other hand alternated with Troy's hand in shafting Caitlin. Panting harder she croaked "Ahhhhh, Troy yes, more, Ahhhh, Troy, more, faster, ooooh, yes, Troy fuck me Troy fuck me"

"You don't even know who's doing you, there's two of them but you don't care. You're out of it. You're happy just so long someone is screwing you. You huge obese whore, look at the roll of flab around your gut. You two guys must be pretty desperate if you can't find any thing better than those droopy udders, fat arse and huge thighs" jeered Jenny "Be careful you stay on top or the fat slut will squash you." She took another swig of her coke and bourbon before putting her head down to play another pool shot.

Brushing aside her two tit suckers Caitlin rose and walked quickly over to the pool table her breasts wobbling as she moved. With one hand she picked up a pool cue one of the men had left against the table. With her other hand Caitlin grabbed the back of Jenny's neck, pushing her face and body down hard onto the pool table. Jenny yelped with surprise then cried in pain as Caitlin brought the cue down hard onto Jenny's butt twice. Jenny squirmed and tried to stand up but now learned that while Caitlin's body might be flabby she was strong enough to hold her still with one hand.

"Jenny don't struggle, I am much stronger than you. You won't get away. You thought I was having my brains fucked out but I heard what you said. You were rude to me before. I don't like junior staff who are rude to me. First I think you should apologise" so saying Caitlin brought the cue down again another stinging blow.

"what the fuck?" cried Jenny as she squirmed, trying vainly to break Caitlin'' grasp and to avoid the blows raining down on her ass. After a few moments she humbled her pride saying through clenched teeth "I'm sorry Caitlin"

"Now Jenny" said Caitlin, lightly tapping the cue on Jenny's butt "you need to learn a few lessons about the rules here. The first is to be polite to the other staff especially supervisors and managers. You've broken that rule in a big way and I must punish you" Two more savage blows on Jenny's butt made her squirm. She tried to stand pressing her hands on the table as if doing push ups but could not break Caitlin's grasp. Caitlin seeing what Jenny was trying to do smacked her knuckles with the cue. "Jenny you'll not get away till you learn to behave. Do you understand the first rule? Jenny I'm not hearing you" With that Caitlin gave Jenny already sore butt another two stinging swipes. "Jenny, I'm still not hearing you- what do you say"

There was a lot Jenny wanted to say as she lay there twisting , trying to get out of Caitlin's grasp and away from the cue that hurt so but nothing would do any good. All she could do to escape was to meekly say "Yes Caitlin, I'll be more polite in future"

"That's a good little girl. You have broken the Second rule a lot too already so I'm going to have to punish you now" and with that Caitlin beat her twice again "The rule is junior staff like you do what they are told when they are told to do it"

"Yes Caitlin, I'll do what I'm told when I'm told"

Caitlin smirked; punishing pretty young sluts like Jenny was as good as watching them have sex and that would happen very soon. She would have obeyed her Master's orders for tonight even without the $1,000 she had been promised if she broke Jenny in properly. After what Troy and Wayne had done for her on the couch a few moments ago and now this Caitlin felt herself coming for the first time tonight. "I knew you'd begin to understand. You do know that I'm teaching you all this for your own good don't you? Jenny, once more I'm not hearing you"

Jenny fought back tears as Caitlin hit her with the cue twice again. "Yes Caitlin, I know you are teaching me to help me"

"Well then be polite, I hope you haven't forgotten the first rule. What should a scrag like you say when someone helps them"

"Thank you Caitlin" Jenny muttered through clenched teeth. What she would do to Caitlin if she ever had a chance.

"Louder please Jenny so the men here can hear you and tell us all why you are thankful"

"Thank you Caitlin for teaching me how to behave at the resort"

Caitlin's smirk widened, her breasts and belly shook with her orgasm. "Jenny another rule you've broken is don't try to be clever, don't backchat people" The cue slashed down twice more.

"Yes Caitlin, I won't act up anymore"

"Just one more rule now, I don't think your little mind could cope with too much at once. But before the rule some advice; actions have consequences. You do something you have to be prepared for the result and you might not like it. So for example, last week you fucked two strangers in the one night

Jenny tried to speak. Again the cue sliced down. Two more welts on her butt.

Caitlin tittered "Speaking out of turn Jenny? I don't think you've learnt the first lesson well enough"

"Please Caitlin, I have learned that, don't hit me again"

"This is great" thought Caitlin she knew she had dominated Jenny at least for the moment then continued talking to Jenny "I suppose you were going to ask how I knew about that little episode. Word gets around and these guys here heard too. So they know just what a little nympho whore you are. So the result is that when men see you with your tits hanging just about out of your clothes, they expect you're ready for some serious screwing. Now I know that you just wanted to tease them, you think they're not good enough for you, you get your fun from tormenting men. Well here's the rule which you've broken" Caitlin slashed the cue on Jenny's butt yet again. "Don't be a tease, don't torment anyone especially my friends here. The consequence of your reputation as a filthy slut and your actions here are that there are three very horny men here. You caused it you have to bear the consequences. Stand up whore and face me". With that Caitlin let go of Jenny's neck.

Jenny, glad that at last the worst seemed over stood. Caitlin grabbed the collar of Jenny's blouse tearing it off her, then knelt before her pulling Jenny's skirt and panties to the floor. Caitlin's hand reached behind Jenny drawing her closer while Caitlin's other hand groped at Jenny's breast. Now Caitlin's tongue began to lick Jenny's cunt in long oval movements.

Jenny gaped her mouth hanging wide in astonishment. Never before has she even thought of any lesbian activity but here is Caitlin, whom she feared and hated and who has just hit her till Jenny's tail was a mass of red welts licking her out and fondling her breasts. To her surprise Jenny felt her body respond, her tits becoming sharp points, her pussy juices flowing. Within a few minutes Jenny's knees began trembling, her body started to shake.

Jenny looked around; all five men are staring at her and Caitlin. The two who'd been entertaining Caitlin sitting on the lounge half stripped, the other three with hard ons showing through their jeans, stood together, drinks in their hands, at the pool table.

Caitlin stopped, stood up. Placing her hands on Jenny's shoulders she walked Jenny back till Jenny stood her back touching the pool table. With one hand pushing on Jenny's breasts, the other between Jenny's legs Caitlin lifted Jenny sending her sprawling on the table on her back.

Caitlin turned to the three men. "Here is one girl who won't tease you again. Suck her breasts, rub her cunt and she'll be begging you to do her over in a few minutes. Go on boys." Saying this she walked over and unzipping their pants quickly fondled each mans cock before returning to her two friends on the lounge.

The three men needed no further encouragement falling on Jenny like wolves on a fallen deer, two sucking a breast each the other at her cunt masturbating her with one hand, fingers of the other exploring inside her. Jenny groaned, muttering to herself "that bitch Caitlin left me before I came properly. What's happening to me, that dyke belted me, then got me almost boiling, I need these men to finish me off That whore's done this before. She knew I'd be like this –putting myself out for three strangers. I hate her. I want a fuck so bad." Her hands searched for the tit suckers cocks and began jacking them off. She orgasmed screaming "Fuck me! O fuck me now! Please! I need a cock in me now! Let me feed on your cock! Tit fuck me too! She wriggled diagonally so her butt was on one side of the table her back arched, her breasts pointed upright at another edge her head hanging low. Spreading her legs as wide as she could she guided one of the men inside her with one hand. Impaled with one thrust Jenny felt her moist pussy walls expand to accommodate the thick cock pumping in and out of her while the man's fingers continued to stroke her swollen mound. Jenny's other hand took the cock it was holding to her mouth. Her head bobbed rhythmically as she began sucking. The third man pushed her breasts together and did as he was asked too.

Caitlin smirked, her eyes closed as she listened to the soft squelch of one cock thrusting in and out of Jenny pinning her to the pool table, to Jenny's louder slurp as she sucked steadily on a second cock, to the slam of the third mans balls as his shaft pressed against Jenny's breasts and to the grunts and groans of the three men as they fucked Jenny senseless. Caitlin knew she had her thousand dollars, though that wasn't up most in her mind. When she had left Jenny to the three men Wayne had taken off her skirt and panties and shoved her naked on the lounge. Fat legs spread wide, belly shaking; Caitlin watched the three work Jenny up to the boil. Troy and Wayne resumed sucking Caitlin's breasts and both had a hand in her cunt both masturbating her while together jabbing two fingers each in and out of her slit. "Mmmm soo good, both of you finger fucking me, yes, yes, harder Troy faster Wayne fill me Ahhhh, yes, Ahhhh".

A few minutes after Jenny showed herself to be the whore she was by calling out to be fucked, Caitlin too climaxed, throwing her head back and yelling "Yes, Yes" then slumped forward. Wayne and Troy roughly dragged her off the lounge on to the floor where she knelt on all fours panting "Troy let me suck you" Her mouth closed round his fat cock her tail grinding in the air till Wayne took her doggie style and her body rocked back and forth as two hard cocks drove in alternately from either end of her.

One by one the men climaxed and soon left. Jenny lay on the pool table her sides heaving, sticky from sweat and semen, thoughts running through her head "I've never had anything like that before, I must be the slut Caitlin says I am because I liked it, I'd do it again. What's Caitlin done to me, Hell she's a bitch. God, I'm not finished yet, I still need more". She started masturbating.

Caitlin walked up. "Jenny let me solve your problem. Spread your legs" Parting them herself Caitlin knelt and licked Jenny expertly, her big tongue caressing every part of Jenny's cunt, pleasuring her till it was almost painful. Jenny orgasmed again "Oh God, Oh yes, Caitlin you bitch, you whore, I hate you, you're a witch".

Caitlin stood "Well Jenny now your first lesson is over. Did you enjoy it? And to think you called me a whore. I saw you -being done by three strangers. You don't even know their names. Even that wasn't enough for you. I had to help you out".

"Caitlin, you are a whore the biggest, fattest whore I've ever met. Who licked me so I had to have those men to finish me off? Who started it all off with those two men? You did you fat ugly slut and you've done it all before haven't you".

"Temper, temper" Caitlin chuckled "sounds like you've forgotten the first part of the lesson. Perhaps I need to remind you with this" Caitlin brandished a cue before Jenny's face. "And your whole lesson is all on video too. Perhaps I could send a copy to your parents at 270 Robin Avenue Camden New Jersey. I'm sure they'd like to see their daughter was so turned on by a bit of discipline and a quick leso lick that it took three men and then me again to satisfy her".

Jenny lept up horrified. "Oh shit you bitch you can't do that. You made me do this. You set me up. You had the video all ready. You loathsome shit. You'd break my parents' heart. Anyway what about yours, you're on this video too".

Caitlin's hand lashed out one stinging slap on Jenny's face. Then one contemptuous shove brought Jenny to her knees. Caitlin picked up the cue and brought it down three times on Jenny's butt. "you haven't learnt your lesson at all. Yes I did have this all planned but you set yourself up by fucking those five men last week. As for my parents well my mother would be pleased, she starred in a lot of C grade porn films. She'd be pleased to see I was calling the shots in my own films. And she never knew who my father was. Could have been one of a dozen or so men she screwed 9 months before I was born. I think you need a lot more punishment and I was so nice to you too, licking you off again".

"No. Caitlin. Please don't hit me again. I'm sorry. I didn't mean to be rude".

"Aright I forgive you this time. Don't let it happen again. But since you asked, yes I did start it off. Wayne and Troy are my friends. We often have little threesomes. Yes I did lick you clean and yes I did it so that you would have to have those three men. They're my friends too But all I did was show you what you have always wanted. I helped you realize your fantasies. You should thank me. You're a prize slut alright and you'll do it again when I want you to won't you?"

"Yes Caitlin. I have wanted group sex. Thank you for showing me that. Yes, I'll do it again when you want me to."

"That's better then. And let me answer your other question. Yes I have done this before. Several times in fact. You'll meet some of the girls I've trained soon. They sometimes get paid to do what you did tonight. If you are good you might get paid too. Naturally, you'll pay me half of what you get. They do. After all I trained you all. And I've got videos of each of them, just like I have of you, to send to their parents or friends if they don't behave. You might be interested to know I also get paid for breaking you in tonight. Now clean up this room and go back to your own room." Caitlin dressed and left.