Charlie and Karen - Cover

Charlie and Karen

Copyright© 2009 by MisterE

Chapter 16

Erotica Sex Story: Chapter 16 - When Karen learns that Charlie has handed in his notice she makes him an offer he can't refuse and they begin a roller-coaster ride of hot, kinky, sexual adventures. He ends an on-off relationship with a boring lover who wants him back and she goes to some extreme measures to split them up. Join the ride as they team up with a virgin and her twisted parents, a porn film maker and other sundry characters. Story codes do not apply to all chapters. Specific codes are included in each chapter.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Consensual   Heterosexual   MaleDom   Oral Sex   Anal Sex   Fisting   Size  

Codes for this chapter - MF FF MM bi cons cd mult Mdom Msub oral anal rubber fist toys creampie SM needles ws

After getting the new staff settled in on Monday Karen arranged another visit to Luke's SM studio. Charlie wanted to go to see if he could learn Luke's technique and Helen wanted to be punished by him again. She fixed it for Wednesday night but asked if he could get more guests there. "Especially men, there'll be two of us to be used this time." Karen wanted to set off early so they could have some fun with Helen on the way but Charlie said no.

"It's not fair to leave Gilly to do all the work."

"I don't mind," said Gilly, "and there's not that much to do at the moment."

"Helen said that Cyril was having a week's holiday," Karen said. "She wanted him to come along as well but when I said Luke didn't do men she suggested he come around here and keep Gilly company."

"I don't need him to keep me company, I've arranged to do some rubber investigation with Gary. But he could come round and keep Roberta company, Al is going to join me and Gary."

"Why do I get the feeling you've already planned everything?" Charlie asked. "Is this a conspiracy?"

"No it isn't and we haven't," Karen said pouting, "but it does make sense. In fact I think I'll ask Roberta to give Cyril a session. I doubt he'll discover that she's not a woman until it's too late, we didn't spot him 'til he got undressed."

Charlie knew that he'd lost and gave in gracefully, "Okay, you win. We'll set off early. Gilly, you can stop work when Karen does and make the most of the rest of the day."


"I'm doing an honesty check on the new staff," Charlie said to Karen on Wednesday morning. "I know it's not a nice thing to do but I'm doing it anyway and I'll be repeating it every time we take on someone new."

"I agree with you, they've all got reasonable references but we can't be too careful. Are you going to tell me what you're doing?"

"I'm leaving small amounts of cash around in various places and increasing the time frame for the security system. I don't enjoy doing it but I can't afford to take chances, there's a lot of valuable things here."

"Yes, I know. And I'm the most precious thing you've got but no-one will steal me away from you."

"You are, I wouldn't swap you for all that I own. This is just to ease my mind."

"It's a good idea, if they're honest they won't know anything about it."

"I'll tell Gilly what I've done before we set off."

"No, don't say anything to anyone. I trust her as much as you do but this has to include everyone. I don't think you should have even told me."

"You have to know, I don't want you to disturb anything that I set up."

"Okay, I see. So if I find cash lying around I should leave it alone."

"Yes please, none of it is well hidden and most is in plain sight."

"I've told Roberta about Cyril coming over, she's eager to have some fun with him. She says she's going to dress him up as a maid and make him do some cleaning. You know she prefers to be thought of as a woman."

"It's not hard is it, she's very pretty when she's dressed up."

"She was thinking of having the sex-change op but she's put that on hold for now and just wants a pair of tits to start with. She's going to get the hormone treatment to make them grow."


Gary prepared a late lunch of sandwiches which he served in the breakfast room. Al joined them but Roberta continued his cleaning duties. Cyril and Helen arrived shortly after and were introduced to the staff. Karen took Cyril to meet Roberta. "Don't let appearances fool you," Roberta said, dressed in a conservative maid's outfit of long skirt and heavy white blouse that reminded Cyril of the clothes Gilly wore when she was a waitress. "I'm going to have some fun with you today. Now get on your knees."

"I'll leave you two to get to know each other," Karen said, giving Roberta a wink. "I'm sure you'll get along just fine."

"Follow me worm," Roberta said, walking around the balcony that overlooked the entrance hall. "Miss Karen wants me to turn you into a maid." She took him to her bedroom on the top floor and told him to strip. "Urgh! That's disgusting. You can't be a maid with all that hair. There's a razor and stuff in the bathroom next door. Go and shave, everywhere. The only hair that I want see left on your pitiful body is on your head. Go on, get in there and don't come back 'til your skin's as smooth as mine."


Al helped Gary clean up after lunch while Gilly went back to the office to finish a few bits and tidy up. Helen and Karen went to get changed into sexy clothes for the afternoon while Charlie set the security system as he wanted it. Half an hour later they set off with Charlie driving, Karen beside him and Helen on the back seat. Both women flashed at the wagon drivers as they passed them on the motorway. Helen was particularly brazen, lying on the back seat with her legs spread wide, her knickers pulled to one side and her fingers dipping into her pussy.

They didn't stop at the services but drove straight to Leeds, pulling off the motorway on the outskirts of the city. "I fancy a drink," Karen said, "take us to a pub will you Charlie. Not a fancy one, let's find a rough place." Charlie found a pub in a run down area and parked in the road close by. Considering the area, Karen was surprised that the pub was fairly empty, she'd expected quite a few unemployed people to be drowning their sorrows.

Charlie waited a few minutes after they'd gone in before following. He didn't acknowledge them as he stood next to them at the bar and ordered a pint. Karen and Helen got their drinks and went to a seat under the window, facing the bar. Charlie leant on the bar, chatting to the landlord.

Karen sat close to Helen with an arm draped over her shoulders. After a few minutes she started to gently rub her fingertips across Helen's nipple. Helen stiffened for a second but relaxed quickly. When Karen leaned closer she turned her head and their lips met. The murmured conversations that were the only sound stopped as the customers noticed what was going on.

"Does this sort of thing happen often?" Charlie asked the landlord.

"Yeah, from time to time but not usually with two smart women like those. I don't mind, it's just a bit o' harmless fun but it keeps the poor sods happy for an hour or so. Usually they just play around a bit and then leave, they don't do any damage."

"Do you think they're whores?"

"Nah, whores don't come around here, not enough money in this area y'see."

Karen had one hand inside Helen's blouse and bra and was swiftly opening the buttons with the other. Helen just sat back submissively and let her do whatever she wanted. When she'd pulled the blouse wide open Karen pushed Helen's short skirt up around her hips and started stroking her bulging mound. Helen opened her legs, putting one over Karen's to give her better access. Karen scooped Helen's tits out of her bra and pulled her knickers aside.

"They don't usually go this far," the landlord said to Charlie as they watched. "I reckon these two get off on doing it in public."


"Do you still want to see my rubber stuff?" Gary asked when he found Gilly in the office. He was wearing nothing but a pair of tight, black rubber pants. Gilly couldn't fail to see the huge bulge of his erection.

"Sure, I'll just finish up here, I'll not be a minute."

"I got a lot of this stuff for my ex-girlfriend," Garry said as he took the stuff out of his drawers. "She loved rubber as much as me but I dumped her when I caught her shagging another guy. I'm not a jealous type, we had an open relationship but we agreed to tell each other before we shagged anyone else."

"I suppose that's fair enough," Gilly said. "Can I try any of this stuff?"

"Go ahead, it's all been cleaned since it was last used. You've got a great body. I hope you don't mind me saying."

"Thanks. You're not so bad yourself. Are those pants padded or is all that you?"

"Look," Garry said, peeling them down, "It's all me."

"Mmmm, very nice. I'll try that as well if you don't mind,."

Gilly tried on a red, rubber bra and matching knickers. "Mmm, feels good," she said, running her hands over the soft shiny surface. "I could get into this stuff."

"It can get a bit sweaty after a while," Garry said, "especially in something like this ... Listen, it sounds like Cyril's in trouble with Roberta."


"Who said you could have a wank," Roberta shouted at Cyril when she went into the bathroom to see what was keeping him.

"No-one Mistress. You didn't say I couldn't though."

"You ask permission in future. Do only what you're told with me. If I catch you doing anything like that again I'll make you sorry. Now come on you lazy worm, I want you dressed and working in five minutes."

Cyril followed Roberta back to her bedroom. Roberta had already changed from her usual clothes into a shiny, red pvc top and short skirt with white stockings and high heeled stiletto shoes. Cyril thought she looked great even though her hips were very narrow and her arse very small. She did have a fair sized pair of tits but the top she was wearing left no sign of cleavage.

"Get that lot on," Roberta said, pointing to the clothes she'd laid out. Cyril struggled with the bra and padding but had no trouble with the stockings, suspenders and french knickers. The short maid's dress didn't even cover his arse but it felt good to him. When he was dressed Roberta put make-up on his face and then stood back to examine her creation. "You'll do," she said, turning and striding away. "Come on worm, there's work to be done."


A few guys came out of the tap room to get a better view of what was happening. A couple of old guys looked over and then turned back to their dominoes, ignoring the display as if they'd seen it all before.

"Fancy a blow job?" Karen asked a scruffy young guy who had come right up to their table.

"Too right," he said, whipping out his cock.

Karen pushed Helen to her knees on the floor, "Here you are, stick it in her mouth." While Helen sucked the guy's cock Karen sat behind her, playing with her nipples.

"Oh yeah bitch, that's it, suck it good."

"Nothing like this has ever happened before," the landlord said. "but what the hell, looks like she's a real good cock-sucker."

"Not bad but I reckon my wife's a damn sight better."

The guy came pretty quickly, he probably hadn't had a decent blow-job for ages. As he stepped away, pulling up his zipper, another guy took his place. Eight more men were queued up waiting for their turn, Helen sucked them all, one after another. "Keep an eye on the bar will you," the landlord said to one of the men as the last one shot his come into Helen's eagerly gulping mouth. "I might as well get a bit of her as well."

When the landlord was done Karen let Helen sit beside her and played with her wet cunt. "If any of you lot has a condom and can get it up again you can fuck her."

There was a mass stampede to the gents as they all searched their pockets for coins for the durex machine.


"Didn't anyone tell you that Cyril's my dad?"

"Hell no. Isn't that a bit embarrassing for you?"

"No, its cool. I think it's great actually."

"So Helen's your mum?"

"Yes, she's off for some fun with Karen and Charlie."

"Sounds like you've got a great relationship with your folks. I guess they know about you as well."

"Yes of course they do, there's no secrets in our family."

While they'd been talking Gary had put on a full body suit of black rubber. "What do you think?" he asked as he zipped it up. The suit covered him from ankles to neck, only his cock and balls, hanging out through a hole in the crotch, were visible. Just above the crotch hole a realistic looking dildo stuck out.

"You could give a girl a great time in that," Gilly said with a giggle. She had added a matching suspender belt to the bra and knickers she was already wearing and was rolling thin, stretchy rubber stockings up her legs. "I love getting fucked in both holes at the same time."

Gary watched her put on a short, clinging rubber skirt and bolero top. "Take those knickers off and I'll give it to you right now." he said as she did a quick twirl.

"Then you can fuck me," said Al who was standing in the door wearing nothing but a tool belt. "I love a good double fuck as well. Roberta's got Cyril cleaning the landing along here but they won't mind."

"Gilly's dad might, we'd better close the door." Gary said.

"No, leave it open."

"Hang on," said Al, "who's your dad?"

"Cyril, like I've just told Gary, there's no secrets in our family so we'll leave the door open. He'll get a thrill from watching me getting fucked. I got a thrill from watching him getting it."

"That's pretty kinky," Al said, "but what the hell, I don't mind if you don't."

Gilly took off the rubber knickers, told Gary to lie on the bed and mounted him so she was facing the door. Al got beside her on the bed and they kissed as Gilly rode Gary and his dildo. "Hi dad," Gilly called out as Cyril appeared on his knees in the doorway, scrubbing the floor.

"Please Mistress, may I talk to my daughter?" Cyril asked.

"Very well but only for a minute."

"Hi sweetheart, it's nice to see you enjoying yourself."

"It looks like you're having fun too," Gilly moaned, slamming down hard on the two shafts. "You'd better not hang around here though, Roberta's looking very pissed off."

"Okay darling, I'll get moving. Enjoy yourself but don't wear that young man out."

"Wait," Roberta said, "there could be some cleaning up for you to do soon."

"No," Gary panted, thrusting up to meet Gilly's descending arse. "I've got to fuck Al next, I won't be coming for a while."

"Okay, move your arse worm. See you all later."

"Oh fuck ... I'm coming." Gilly gasped as Cyril crawled away.


"You didn't really think I'd let that bunch fuck you, did you?" Karen asked as she hustled Helen out of the pub.

"Yes I did," Helen replied, hurriedly putting her tits back into her bra and pulling her blouse together as they walked quickly towards the car. "I was looking forward to it."

"You filthy whore," Karen laughed. "You're too good for that lot. They can think themselves lucky they got a blow-job off you."

"It looks like the entertainment's over," said the landlord as the women rushed out.

"Sure does," Charlie agreed, downing the last of his pint. "I'd better shoot off too. I only came in for a quick one."

"Looks like you missed your chance then," the landlord said with a laugh as Charlie walked out.

"Where to now?" Charlie asked, getting into the car.

"Let's go to a better pub, one with some decent blokes."

Charlie soon found a pub in a smart area and drove into the car park. It was fairly quiet inside with just a few people hanging around the bar and sitting at tables. Soft music masked the quiet conversations but the tinny bleeping of a modern fruit machine occasionally disturbed the peaceful, relaxed atmosphere.

"Okay, here's what you do now," Karen said as they sat together at a table. "Pick out a guy that you fancy and when you're ready go and tell him you want to be fucked and take him to the gents toilet. To make sure you're alright Charlie'll go in just before you."

Helen looked around, picked out the one she fancied, a business type of about her own age, and went over to him.


"Move it you stupid piece of shit," Roberta growled, whipping Cyril's raised arse through the thin knickers. "You're fucking pathetic, I'd've had this floor done in half the time. Here, let's see if this'll get you moving any faster." She pulled his knickers aside and roughly jabbed the whip's handle into his arse. She kicked the back of his leg to get him moving again and made him finish the landing before taking him downstairs. Cyril headed to the dungeon door but Roberta sent him into the surgery while she collected a few bits from the dungeon.

Cyril stayed on his knees while waiting for Roberta, looking at the chairs with their stirrups. He hoped she was planning to make use of one of them. "Get on the chair and put that on," Roberta said, throwing a leather hood at him. The hood covered his head completely but left his mouth uncovered. She fastened the straps around his legs once they were in the stirrups. Further straps held his arms and one across his chest left him with very little movement.

Roberta cursed herself for not making him take off his knickers first but then, since she didn't like them herself, simply ripped them off him. Cyril's cock was rock hard, it had been ever since he'd seen Gilly getting fucked. Roberta grabbed it and the full, heavy balls making Cyril groan, apart from Helen, she was the first 'woman' to actually touch his cock and balls. Roberta stroked the shaft and played with the balls for a few minutes before pulling the whip out of his arse. Then she got some soft rope and tied it around the base of his smooth shaven cock. Slowly and carefully, she wrapped the rope around and around his scrotum, squashing the nuts into a ball of tight skin. Without saying a word to him, she picked up the whip and flicked the tips of the tails against the hard, tight ball of his nuts. Cyril gasped, his cock twitching with each light blow. When Roberta used her sharp fingernails to scratch the taut flesh he groaned and started leaking clear fluid from his knob. She wiped some up on her fingers and fed it to him before smearing the pre-cum around his arse and digging two fingers deep inside.


"Al's turn," Gilly said climbing off Gary.

Al got on her knees and rested her face on the pillow, "From behind please, Gary," she said, pulling her cheeks open for him. Gilly spread some oil onto Al's arse as Gary got into position. Gary wedged his cock and dildo into Al's holes and slowly pushed in, sinking both lengths fully in one long slow movement. Gilly scooted around, pulled the pillow out from under Al's face and sat in its place with her legs wide open. Al dived in and went straight to work on Gilly's clit, sucking and licking it as Gary slowly began to fuck her. "Your pussy tastes so sweet," Al said, raising her head and smiling at Gilly.

"I know," Gilly said, pushing Al's head back down. Gary made Al come quickly but kept on fucking her to two more orgasms before he was ready to come.

"Who wants my spunk?" he asked quickly, holding still in Al's twitching cunt.

"Give it to Al," Gilly said, "I'll clean her out when you've finished.

"Thanks Gilly," Al moaned as Gary began to fuck her with deep, hard strokes. "I love getting filled with spunk."

Gary growled as he came, holding Al's hips tight as he finished off with short sharp jerks.

"Let Al clean your cock while I suck your spunk from her cunt," Gilly said as she got ready for him to pull out.

Al's cry as Gilly started sucking her cunt was abruptly silenced as Gary stuffed his slowly softening prick between her lips. Gary shuddered as Al sucked hard on his sensitive knob, pulling it deep into her mouth to get as much of it clean as she could. When she'd got all she could like that she held it gently and licked all around the base, cleaning her own sweet juice from out of his pubic hair.

Gilly sucked and slurped noisily, thrusting her tongue deep into Al's cunt to get every last trace of spunk out of her. When Al's cunt was clean she moved to the woman's clit and worked on that until Al came again.


"No, I don't want a drink. I want a good fuck," Helen said when he offered to get her a drink. "Do you think you're up to it?"

"I've got a room in the hotel across the road. Come on, let's go,"

"No, let's do it in the gents."

"Whatever you say honey," he said, slipping an arm around her and grabbing her arse.

Charlie was waiting near the toilets. When Helen turned to walk towards them he slipped inside and went into one of the cubicles. A few seconds later Helen and the man entered. "Come on, it'll be cramped but we won't be disturbed." he said, trying to pull her into a cubicle.

"No, right here," Helen said, bending over the wash basin and flicking her skirt up over her arse.

"Well, okay. If that's what you want."

Charlie stood up and looked over the partition. The guy was rolling a condom onto his cock while Helen was holding her knickers aside and fingering her wet slit.

"Come on big boy," Helen groaned, "get it in me. Fuck me."

"What the fucks going on out there?" Charlie called, rustling his clothes then flushing the toilet.

"Hey, calm down pall, me and this lady's just having a little fun," the guy said, slipping his cock into Helen's hot wet cunt. Helen groaned as he sank in but it was only for his benefit, she could hardly feel his little cock which she thought was smaller than Cyril's.

Charlie unlocked the cubicle and stepped out, "Mind if I watch," he asked as he washed his hands.

"Hell no," the guy said, "just don't interrupt okay."

"Do you want ... a blow-job?" Helen asked, panting and pushing back against the guy.

"Sure," Charlie replied, ignoring the guy who was protesting.

Helen turned towards Charlie and unzipped his trousers. "Oh my God!" she gasped when his half-hard cock came out of his shorts. "I don't know ... if I can ... suck all that."

"Just do what you can," Charlie said as she stroked it. "Don't worry, I won't try to force you."

Helen opened her mouth and started sucking Charlie's knob. The guy just stared at the massive length.

"Good thing you're not gonna fuck her," he said, rocking back and forth while holding her hips. "You'd tear her apart with something like that. Shit, you've got a hot pussy baby, you're gonna make me come real soon."

"Come in my mouth," Helen said, "don't waste it in a rubber."

"No way baby," he said shaking is head. "I'm gonna shoot it all over your hair. Everyone'll see what you've been up to then."

"No, please, not that, let me drink it, please."

"Do as the lady says," Charlie said looking straight at him.

"Huh, this is my whore, I'll do what I like with her."

"You'll do what she wants or I'll rip your fucking balls off." Charlie said coldly and quietly.

The guy didn't say anything, he just kept on rutting, working himself closer to coming while gripping her hips tightly. "Here it comes baby," he said, pulling out and ripping off the condom as Helen turned to take it in her mouth. For a second he tried to keep her mouth off his cock but a quick glance at Charlie told him that would be a very bad idea. Helen got the head between her lips just as the first trickle oozed from his knob.

"Do what you like with the whore," the guy said as he zipped up his trousers. Charlie took a step toward him but Helen held him back.

"Don't bother, with such a tiny cock he's got enough trouble," she said. "This is what I call a real man's cock."

"Get out," Charlie said, "go on, fuck off before I change my mind."

"Fuck me Charlie," Helen said. "You owe me one from the other night." Charlie got behind her and slipped easily into her flooded cunt. "Oh shit, that's good," Helen moaned, pushing back until his knob was jammed up hard against her cervix. "Fuck me Charlie, please fuck me."


"Please Mistress, give me more," Cyril groaned as Roberta simultaneously scratched his balls and fingered his arse.

"What? What do you want more of?"

"Anything Mistress, anything you want to do to me."

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