Charlie and Karen
Chapter 9

Copyright© 2009 by MisterE

Erotica Sex Story: Chapter 9 - 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 - FF cons bi oral anal toys fist Fdom SM span exhib

Gilly was going to keep her new underwear on for the night but didn't like the way the bra looked under a tight tee-shirt. Karen suggested she go out without a bra and, feeling a quick thrill at the daring idea, Gilly agreed. "Just look at these," she said to Karen, pointing to her nipples which were erect and stood out clearly through the soft, clinging shirt.

"So what," Karen said pulling on her own tee-shirt, "they look great but mine are even bigger."

"Dressed like that, you might as well not bother wearing a top for all it hides."

"Okay, if that's what you think I should do," Karen said, pulling off her shirt.

"That's not what I meant and you know it," Gilly laughed.

Karen wouldn't change her mind so Gilly shrugged her shoulders and said, "Come on then, show-off, let's go."

For decency's sake Karen did wear a short, light jacket that buttoned between her tits. A lot of flesh was exposed making it obvious that she wasn't wearing anything under it but it did at least cover her breasts.

It was well past seven when they got to the Pheasant, Robbie and Bill were at the bar waiting for them. Both made appreciative noises at what they saw. Robbie's were much more coarse than Bill's but the girl's enjoyed the compliments anyway. They stayed in the bar for an hour or so, Robbie was trying to get both women drunk but Karen knew all the tricks and warned Gilly to be careful. Karen put on such a good show of getting intoxicated that Robbie didn't even notice that she swapped the spiked drink with his own. As a result he got drunk while Karen and Gilly only got slightly merry. Robbie suggested going back to his place and, giggling, Karen and Gilly agreed.

"I think you should warn Helen that he only wants to have sex with her." Bill whispered to Gilly.

"What makes you think we're here for any other reason?" Gilly asked with a sexy grin.

"I don't mean to be disrespectful," Bill said carefully, "I could believe that of Helen but not you. You're not the sort of girl who has sex on a first date."

"You'd be surprised at what I do," Gilly said, still smiling. "Anyway, Ka ... Helen can take care of herself, you saw what she did with the drinks."

"So, she's not really called Helen and I'll bet you're not Alice either." Bill said when Gilly nearly slipped, "It doesn't matter at the moment, getting to know you better is more important than knowing what your real name is."

"Apart from that," Gilly said ignoring the issue of names, "Robbie doesn't look in a fit state to take anyone to heaven, not even himself. That's quite a shame really, as Karen might say, 'The gates of heaven are locked but the hinges are well oiled, if you've got the right key they'll open easily'."

Bill smiled, "He just doesn't know when to stop drinking," he said, leading the way out to his car. "Does the thing about the key apply to you or just Helen," he asked, opening the front door for Gilly. Gilly just smiled as Karen got in the back with Robbie. She had to fight him off all the way back to his flat. Fortunately it wasn't far and he was so drunk that his attempts to get a hand inside her jacket were easily resisted. Bill got the keys off Robbie and helped him into the flat, apologising to both women for his friend's behaviour.

"Well, we can forget about Robbie, he's a waste of space," Karen said to Gilly, "How are you doing with Bill?"

"I like him, he's really sweet and considerate. He told me to warn you that Robbie only wanted to fuck you. I said you could look after yourself."

Karen took one look around the flat and said they were leaving. "This place is disgusting," she said with distaste, "I wouldn't bring a dog in here."

"I'm very sorry," Bill said, "I had no idea it would be like this. Come on, I'll take you back to your car."

"Is your place like his?" Karen asked as they got back into Bill's car.

"Absolutely not," Bill said emphatically, "It might not be spotless but it's reasonably clean and tidy."

"In that case why don't you take us there instead." Gilly suggested.

"That's okay with me," Karen said from the back seat.

Bill lived in his own house, a small terrace in a quiet street. It was nothing special but it was clean and fairly tidy. "Would you like tea, coffee or alcohol?" he asked when they went in.

"A glass of wine would be nice," Gilly said and Karen agreed.

While they made themselves comfortable Bill went to the kitchen to get glasses and a bottle of wine.

"I'd offer to take your jacket," he said to Karen, "but I don't want you to get the wrong idea."

"That's so sweet," she said giving him a big smile. "Robbie would have had it off me in the pub if I'd given him half a chance."

"He can be such a di ... such an idiot sometimes. He's got some good lines with girls but I often wonder if he knows how to get beyond a chat-up line without getting the girl drunk. It's pathetic!"

"Ah, I did wonder why such a level-headed guy would hang around with a complete dick-head," Karen said. "He's got the gab but you know how to treat a girl. I'll bet you do very well off him."

"You've got it," Bill said with a wink and a huge grin. "It can be a real pain at times but I do get a lot more second dates than him. I don't think he's ever managed to keep a decent girl for more than a couple of weeks."

"So how come you're still looking," Gilly asked. "It would have thought you'd have a steady girlfriend by now."

"That's the drawback," Bill replied, "The usual type of girl that falls for one of his lines is too much like him, not my type at all." With surprising honesty he continued, "I'm kinda shy by myself, I just don't seem to have the knack of getting girls talking like Robbie does. If I could use his lines I'd be settled down by now."

They talked for quite sometime, Gilly had no trouble at all, her confidence levels were rising rapidly, she found it as easy to talk to Bill as she did to Charlie. Karen took a back-seat, saying very little while Gilly and Bill sat facing each other on the sofa, talking like old friends.

The mutual attraction was obvious, even to Gilly. Karen thought about helping them along by making a few suggestions but held back, they were getting on well enough not to need her intervention. She was sure they'd end up fucking but probably not that night, not even if Gilly hadn't been on her period.

"I'd really like to see you again," Gilly said when Karen pointed out how late it had got. "Can I call you later in the week?"

"That'd be great," Bill said, "I'd like to see you again too."

He took them back to the Pheasant and got a lingering kiss from Gilly before she got in the car with Karen and they drove away.

"He got a hard-on when I kissed him," she said. "It's a good thing we were leaving or I might have ended up giving him a blow-job right there in the car park. It feels like he's got a lot to offer."

"Are you talking about him or his cock?" Karen asked with a giggle.

"Both actually. I like him, I'm going to fuck him."


"Damn, I wish I wasn't on," Gilly said when they got back to Karen's, "I could really do with a damned good fucking."

"I don't have that problem," Karen said, "I don't get periods, it's something to do with a hormone that my body isn't making. Some women would call it a curse because it means I can't have kids but I think it's a blessing. At least I do now that I've accepted it."

"Well I think you're lucky, I hate my periods, I always have. I'd like to have kids though so I'll just have to put up with them."

"I wanted to have children and went through loads of treatments to try and get things working but nothing helped. When I split with my boyfriend at the time I gave up with the treatment. Since then I've given up on the idea of kids entirely and concentrated on enjoying my sex life instead. How long do your periods last?"

"Three days, sometimes four."

"Think yourself lucky then, some women I know have periods that last for over a week."

"I'm going to get changed," Gilly said, "I'm not ready for bed but I'd like to get a bit more comfortable."

Karen got changed into a dressing gown as well. While she was changing she looked out of the window and saw Cyril Stafford watching her from his window. Her first instinct was to shut the curtains but her wicked side won and she left them open. Smiling to herself, she stood in front of her window for many minutes, playing with her tits and nipples.

She decided not to tell Gilly as it would probably upset her. She didn't tell her that she was wearing her strap-on either. Gilly had changed from her tight tee-shirt into a loose one and nothing else, she was sitting on the sofa with her legs tucked up and a hand on her pussy.

"Can we watch your video again," she asked when Karen came down.

Karen switched on the TV and set the tape playing. Gilly cuddled up close to her and continued to stroke her pussy. Her breathing grew heavier as she slowly worked herself towards an orgasm. "I'll do that for you if you like," Karen offered. "Or I could fuck you if you still want to," she added opening her gown so Gilly could see the dildo rising from her crotch like a real cock.

"It'd be a bit messy. I once tried my vibrator when I was on, I had to wash the sheets myself so mum wouldn't see."

"I wasn't thinking of your pussy, I was thinking of your arse. You loved it last night."

"Oh, I forgot about that. Damn, I could have asked Bill to fuck my arse earlier. Okay but use a bigger dildo than last night, I want to get my arse stretched enough for Charlie to fuck it."

"I'll start with a little one all the same. It did hurt you, remember. You tell me when you're ready for a bigger one then I'll swap them over. First though, let's go upstairs and get you acquainted with an enema. It's not so important at the moment since we're only using a small dildo but you might as well get used to it."

Using the enema was a bit messy but it wasn't painful, nor was it pleasurable. "It gets easier with practice," Karen said. "You should try and hold the first wash in for as long as possible. Keep doing it until the water comes out clean. I know it's not particularly pleasant but it makes getting your arse fucked a whole lot more pleasurable for you and your partner. The last thing you want is to find a brown stain or worse on his cock when he pulls it out. I've got so used to doing it that I always have one after a poo whenever I'm at home."

Karen left Gilly in the bathroom and went down stairs to turn off the video, TV and lights. Gilly was lying on the bed naked with the three smallest dildo beside her when Karen returned. "Pass me the first dildo then get on your knees," she said, hanging her gown on the back of the door.

Gilly took up the position, holding her cheeks apart as she'd seen the women do in the videos. Karen laid a vibrator beside her, "It's for your clit if you need it," she explained, "you might want to use it anyway." With the dildo coated with a sheen of oil and a little on Gilly's arse, Karen got behind the girl and slowly pressed the tip into her arse. Gilly stifled a little yelp of pain so Karen waited for a few seconds before carefully pressing in deeper. It took only a few seconds for Gilly to become accustomed to the dildo and start to push back onto it. Karen took it as the signal and started to fuck her young lover with slow, deep strokes.

Karen's motion soon had Gilly panting but, even though Karen went faster, Gilly still didn't come for her.

"Why can't I come," Gilly gasped, humping back hard on the dildo.

"Maybe because you haven't got Charlie in your pussy tonight." Karen said slowing down.

"But I know I was coming in just my arse last night, Charlie wasn't even moving in my pussy."

"Perhaps you need something a little bigger. Do you think you're ready for the next one?"

"Yes, I think so. Let's try it anyway."

The six inch dildo went in easily and brought Gilly to orgasm after only a few deep strokes. "That's it," she panted, "I'm going to come ... Oh yes ... Do it ... Fuck my arse ... Give it to me ... Yessss..."

Karen fucked her to a second anal orgasm before Gilly asked for the next dildo. It took a little longer and a bit more force to get it in her arse but once the tip was past her sphincter, the shaft slid in easily. Karen was surprised to see Gilly's arse take all seven inches without a pause.

"Oh God, it's happening again," the buggered girl gasped. "It's hurting a little but it's a nice hurt, it makes me want more. It's like an itch deep inside that needs to be scratched. Fuck me Karen, please fuck me."

Karen started slowly but Gilly's immediate response of pushing back hard made her pick up speed and was soon working the bigger dildo as quickly was she'd used the smallest. Gilly came in seconds, squealing and gasping while clawing at the sheets and jerking back against Karen as if trying to get the dildo even deeper.

"I've come really good but the itch is still there," she moaned, still pushing back onto the dildo. "I need to have it scratched but the dildo just won't reach it."

Karen eased out but Gilly cried for her to put it back in. "Your body is saying it wants more," she said softly. "This dildo isn't long enough so we'll try one that might be." Karen went to her drawer and took out the eighteen inch double-ender that she'd shared with Leanne.

"You don't think I can take all of that do you?" Gilly asked when she saw the dildo.

"No, of course not, but we don't know how deep your itch is. Now, do you want me to try this or not?"

"Yes, go on. It's not much thicker than the dildo is it."

"No," Karen replied, oiling a good eight inches of the dildo and spreading some more on Gilly's arse. "Are you ready for it?"

Gilly pulled her cheeks apart and Karen saw her arse open a little. The first seven inches went in as easily as the other dildo. "Deeper," Gilly groaned, "I'm still itching for it."

Holding the dildo just behind the oiled section Karen started fucking the rubber cock in and out, pressing a fraction deeper every few seconds. Gilly kept begging for more, "It's not there yet, please push it in deeper." Karen knew just how frustrating it was to have an anal itch that your lover couldn't reach. The dildo was in up to her hand so she moved her hand back another inch and started to fuck it in and out again. Gilly had another orgasm but still cried out for more when it was over.

"You're teasing me aren't you," she said, "please don't Karen, the itch is getting worse, give me more."

Not wanting to frighten the girl by telling her she already had nine inches of dildo up her arse, Karen said, "Okay, I'm just going to push it in slowly, you tell me when it's deep enough." Having moved her hand back another inch Karen oiled more of it slowly pushed in but it wasn't fast enough for Gilly who jerked back sharply and took the extra inch in less than a second. Her humping motions became more frantic as Karen's hand prevented further penetration so Karen let her hand slip back another two inches. 'How much more can she take, ' Karen wondered as Gilly humped back and quickly took the dildo to twelve inches.

"MORE," Gilly demanded, "give it me you fucking slut, shove it all up my arse."

Karen recognised the sounds of desperation. Holding the dildo with just one hand on the sculpted glans she covered the rest with oil and pushed in. Gilly stopped humping when over fourteen inches were inside, "Jesus, it's nearly there, just a little more, please Karen, just a little more." It took another inch to make Gilly gasp and then groan loudly, "That's it, just there, fuck it, fuck it now."

"Oh Jesus," Karen groaned in disbelief as she pounded the dildo back and forth in her lover's arse. It was in up to the limit, she'd have to let go of the head to give the girl even a fraction more. Even though she was only using a very short stroke Gilly started to come immediately. It was, without doubt, the most powerful anal orgasm Karen had ever seen anyone have. From the look and sound of the girl's climax Karen guessed it was even more powerful than the one she'd had with Charlie's fist up her arse.

"Jesus," Karen groaned again when Gilly finally came down from the incredible peak of her orgasm.

"What," the young woman asked some moments later, "What's wrong."

"Nothing, nothing at all. I can hardly believe it but we've found something you can do better than me."

"You mean the orgasm I've just had. Don't be silly, I've seen you coming with Charlie up your arse."

"No, not that. Here, give me your hand but be ready for a shock, a really big shock."

Gilly held out her hand and let Karen guide it. When her finger's touched the end of the dildo and found how far it was up her arse she did nothing but gasp. "Oh Jesus, you didn't swap dildos did you." It was a statement rather than a question, Gilly knew that she had almost eighteen inches of dildo up her arse. "Oh God." she groaned, "How the hell did you manage to push all of that up my arse."

"With ease lover, with ease. In fact you pushed yourself onto most of it. Hold still now, I'd better take it out before you move."

Gilly had another little orgasm as Karen slowly and carefully pulled the dildo out. When the head popped free Gilly rolled onto her side and hugged her belly. "Are you alright," Karen asked with concern.

"I feel empty." Gilly groaned, "totally empty."

"Rest for a while," Karen said, stroking the girl's shoulder and arm. "Let your body recover."

Karen sat and watched her lover carefully, looking for the slightest sign of physical trauma following the extreme anal penetration she'd just taken. There was nothing, not even the slightest sign of discomfort and after only a few minutes Gilly sat up and pulled Karen close. "Please Karen, don't tell Charlie." she begged as they hugged, "I want to surprise him with this. I'm going to take his cock up my arse the very first chance I get."

Karen would have liked some attention herself but Gilly seemed too tired to do anything so she took off the strap-on harness, turned out the light and cuddled up against her lover. Gilly was asleep in seconds and wasn't disturbed by Karen spreading her legs wide and rubbing her clit while jamming four fingers into her arse until she came.

Gilly was first to get up the next morning. While Karen was still sleeping she had a shower then prepared a breakfast of cereals and coffee which she served to Karen on a tray.

"Mmmm, breakfast in bed," Karen said, stretching and yawning. "It's ages since I had this."

"Don't expect to get it like this every morning," Gilly said with a smile. "This my way of saying thanks for last night, I loved getting my arse fucked and I've discovered something new about my body. I'm sorry I was so tired and didn't do anything for you, that's why you've got breakfast in bed ... Is there anything else I can do to make it up to you?" she asked sliding a hand under the covers and up between Karen's legs.

"You can stop that for starters," Karen said in mock annoyance, "I'm trying to eat my breakfast. At least wait until I've finished before you turn me into quivering mess."

"Okay, sorry," Gilly said pulling her hand out. "I'll wait but don't take too long or I might get bored and get myself another lover."

"Wow, that's something to look forward to." Karen quipped, "Just give me a second to get dressed."

"Seriously though," Gilly said sitting back next to Karen and sipping coffee. "Now that I know how much my arse can take I won't be bothered if I can't learn to do deep-throat or take it right up into my womb."

"Does that mean you don't want to learn how to deep-throat?"

"No, of course I want to learn. I'm just saying I won't be disappointed if I can't do it. I've got one hole that can take any length of cock, it might still need to be stretched a bit more but I've got the depth already. I can hardly wait to see Charlie's expression when he feels his cock going all the way into me."

"Yes, that will be something to see won't it."

"BJ's got a pretty big dick, is it bigger than Charlie's?"

"Yes, he's at least an inch longer, maybe two. I wonder if Leanne's got used to him yet."

"Can you take it all in any hole?"

"He's only had my mouth and cunt, my arse belongs to Charlie, you're the only other person that's fucked it since I've been with him. I don't think I could take it all in my arse though, I once tried a twelve inch dildo but it got too painful at about ten inches and I bled a little when I took it out."

"I'm pretty sure your pussy can take at least twelve inches, if your mouth can take that much then, between us, we've got at least three different holes that can satisfy just about any cock in the world."

"Mmm ... maybe. I've heard about a porn star who's supposed to have a fourteen inch cock, they say he still hasn't found a woman who can take it all."

"Well, we know I could take it in my arse and I'm sure you could take it in your mouth and cunt if you wanted to."

Gilly's suggestion started Karen thinking. She was up for almost anything where sex was concerned. Gilly was learning quickly and could easily become just as kinky. Leanne was also very hot and getting into porn. With help from BJ and Charlie they could do something spectacular especially in the mansion. She kept the idea to herself though, there were too many 'if's' to tell Gilly what she was thinking.

" ... do today?"

"Sorry, I was miles away, what did you say."

"Probably dreaming about a fourteen inch cock up your pussy. I was asking what you wanted to do today."

"Hmmm. First I'm going to finish my breakfast. Then you're going to make up for last night. Then I think we'll investigate more of your potential. After that I don't know, maybe we'll go shopping."

Despite demands that she 'hurry up' from the impatient young girl, Karen finished her coffee and got up to go to the toilet while Gilly cleared away the tray.

"Can I lick your pussy now?" she asked as she ran back into the bedroom.

"No, first we're doing an experiment. Charlie suggested you might have sadistic tendencies. Today we're going to find out if you do and how strong they actually are."

"Okay. How are we going to do that?"

"You're going to hurt me." Gilly's smile faded instantly but Karen stopped the protest she felt sure was coming. "I know you think you don't want to hurt me but we discussed this the other day. You told us that hurting my nipples got you excited but that was when you were trying to make me come. You know I like pain so today's test will hopefully answer two questions. The first and most important one is whether you enjoy hurting me when you know I'm not going to come."

"Alright, I'd rather learn things with you than anyone else. What's the second question?"

"How much I can take without having to come. I've never put myself to that test but it's time I found out. Being in the right frame of mind is important for me, I couldn't do it if I wasn't ready for it but this morning I am ready and that's what I want."

"Okay, what do you want me to do?"

"Preparation first," Karen said, opening her 'toy' drawer. She took out the handcuffs, a blindfold, the whips and cane and put them all on the bed. "Put the blindfold and handcuffs on me, they're not strictly necessary for me but they make the situation more ... realistic."

"And then I use the cane and whips on you?"

"Yes but warm me up with your hand first, then use the whips and cane. Use them anywhere on my body but try not to hit may face. Stop anytime you want but at least give it a proper try, remember I'm testing myself as well. If it really upsets you then tell me and we'll do something else instead."

"I get the feeling that you're leaving it all up to me. How will I know when you've had enough or if I go too far?"

"Good question. That's very important and I'm glad you asked it before we got started, it shows you're really thinking about what we're going to do. The answer is called a safeword, if I say the word you have to stop. I'm going to give you three words though, they are 'Come', 'Wait' and 'Stop'. I can see by your smile you've worked out what they mean but I'll tell you just to be certain. If I say 'come' I want you to make me come, just once though. When I've come go back to hurting me. If I say 'wait' then stop what you're doing until I say. If I say 'stop' I've taken as much as I can and we'll do something else. Only respond to the single words though, I might say anything but I'll give you the signal word alone. For instance I might say something like 'please don't stop' it doesn't mean I've had enough."

"Far from it I would have thought. Okay, I understand all that, are you ready to start now?"

"Just one more thing. Take your time, especially with the cane."

Gilly put the blindfold over Karen's eyes, Karen held her arms behind her back so the handcuffs could be put on her wrists. "Where do you want me to start," Gilly asked.

"That's up to you. You're in charge now, I'll do what you say."

Gilly made Karen bend over and gave her bum a light spanking, there was no response at all, not even a sigh so she slapped the soft flesh harder and soon raised a rosy glow. She then made Karen kneel upright on the bed and slapped her tits a few times. Karen's nipples grew fully erect but she still didn't make a sound. With Karen lying face down Gilly got a whip and used it on her arse, this got her a few soft sighs, especially when she swung it a little harder.

It didn't take the young woman long to realise she would have to be much harder on her lover and swung the whip with as much force as she could. Karen's soft moans drove her on and she found it quite exciting to hear the response. She told Karen to roll over and used the whip on her tits. This got even more moans and sighs and Gilly saw the first signs of moisture between Karen's legs. She gave Karen more whipping on her front, moving down to her belly and even on her mound. Both of them were getting more and more turned on, Karen's moans grew louder as Gilly discovered a way to make the very tip of the whip flick against Karen's skin leaving faint red lines on the rosy flesh.

Having told Karen to get on her knees, Gilly picked up the cane. At first she used it too hard and Karen called out "Wait ... Not so hard, at least not yet. Build up to it like you did with the whip."

Gilly started again, giving Karen's cheeks light touches of the cane and an occasional harder slap. Slowly she moved down onto Karen's legs, leaving a couple of faint red lines across both thighs. She stopped at her knees, dropped the cane and went back to spanking the slim, soft cheeks. This seemed to work better for Karen who gasped and raised her hips.

With Karen kneeling up again, Gilly whipped her tits from side to side and up and down. Karen whimpered softly so Gilly struck them harder and managed to make Karen cry out a couple of times. Looking for a little variety for her lover, Gilly dropped the whip and mauled Karen's nipples with her fingers before treating each to a little nibbling and chewing. Building on this change, Gilly told Karen to arch her back and, while still using her teeth on each nipple in turn, began to slap her lightly stubbled mound. This made Karen respond with louder gasps and groans and even an occasional sharp cry.

Fully immersed in and loving her role as a sadist, Gilly picked up the whip again and lashed it hard against Karen's jutting mound. After a few seconds she added more variety by alternating between, tits, belly and mound. Karen's body jerked and shook with each blow and Gilly could see more fluid oozing between the parted folds of her cunt. "Come!" Karen cried suddenly, falling back and spreading her legs wide.

Gilly dropped the whip and dived between her lover's thighs, clamping her mouth hard around the flooded gash and lashing the swollen clit until Karen came with a flood of sweet, sticky cream.

The test continued for another twenty minutes with Gilly using the whip, cane and her hand all over. At one point she had Karen spread her legs wide and used the whip directly on her exposed cunt. Karen demanded another orgasm after the cunt whipping but it was Gilly who called a stop.

"My arm's too tired to do any more," she said as she released Karen's hands and took off the blindfold.

"That was great," Karen said, rubbing her arms. "How did you feel about it."

"I loved it when I saw you were enjoying it as well."

"I thought you would," Karen said with a grin. "It didn't bother you that I wasn't coming when you were whipping me did it?"

"No, not really. To be honest, I didn't even think about it. I saw your pussy getting wet so I knew you were enjoying it and that was all that mattered."

"That confirms it then, you do have a sadistic streak. Do you think you could do something like this to a man?"

"I'm not sure ... I suppose so. I'd have to try it to know for sure."

 
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