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Sis Helps Out With My Promotion

Category: Group Sex
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I hadn’t seen my sister Karen for about four years and was quite shocked to see how much she had changed; not only in her appearance but also in the way she talked and acted. Karen is three years younger than me that makes her 23 now, she stopped living with mom and dad about six years ago, dropped out of school and travelled around for a couple of years. When she returned home she got mixed up with some very unsavoury characters and eventually took off again with this guy, a real low life who was into everything…drugs, prostitution, you name it, he was into it.

Karen when young was a very sweet, beautiful girl, looking at her sat opposite me I realised she still was beautiful only now the look of innocence was gone and was replaced by one of streetwise hardness. Her bleached blonde hair was cropped short, she was wearing a very short skirt and the thin, tight vest showed she was bra less as her nipples could easily be seen. My name is Stuart; I’m 26, single and was doing alright for myself. I had a great job, a nice apartment and car. I worked for a promotions and advertising agency. Karen had phoned me, she said she wanted to talk and well…this is where my story starts.

Karen took the drink I offered her and sat on the couch, we made small talk for a while, I asked her what she had been up to. She told me the guy she had been living with had been arrested for supplying drugs and was serving a prison sentence, apparently when they were together he paid for everything, she never had to work, then when hw was not around money dried up and eventually she got evicted from her apartment because she had not paid the rent. She got a job in a club as a waitress… “The money was crap, then I met up with this girl who worked as an escort”

“You mean call girl… prostitute don’t you!” I butted in, “Call it what you want, anyway… she told me I could earn real money and gave me the phone number of the guy she worked for, I met up with him and, well…that’s it I guess. For the last six months I’ve been working for him, and then…two weeks ago something terrible happened! I don’t want to go into details but I had to get away, I’ve been staying with friends since then” Have you seen mom or dad since you’ve been back?” I asked, “No, not yet…I will though, soon. Stuart, the reason I wanted to see you is, well…could you let me stay here for a while? I need to get some things sorted out and then, well…I’m thinking of going to Europe or Australia, you know, start a new life. I’ve been thinking a lot recently and I guess I’ve screwed up my life big time. I think it would be best if I could start over, get a good job, meet new people…decent people! I’ve saved up some money, I’m owed some, they have promised to let me have it within the next couple of weeks so I wouldn’t be here long, two, three weeks tops…”

Of course I agreed, it would be nice having Karen staying. She called a cab and went to fetch her things and was back a couple of hours later. That night we stayed up late talking, we ordered a take away, drank a few bottles of wine but as much as I tried she would not tell me what happened to make her decide to leave. I was a bit shocked when she had first told me about her becoming an escort, “You mean to tell me you actually went with guys for money?” I asked her. “Look Stuart, I’ve done many things I am not proud of but truthfully, it wasn’t that bad, I had to get money…it was as simple as that.” She went on to tell me that in the past six months she had put away about 10 grand.

“You’d be surprised at how many rich old men are out there just itching to part with money for the company of a girl” she laughed. Karen had my room, I slept on the couch, I didn’t sleep very much though, I kept thinking of Karen selling herself, the more I thought the more it excited me, I actually got myself off that night with the thought of my sister firmly in my mind. Karen thought nothing of walking around my apartment in her skimpy clothes; she would take a bath and sit around with a towel wrapped around her and one night she actually gave me a hard on by casually strolling from her room to the bathroom wearing just her flimsy bra and panties. She joined me later while I was watching TV, now she had on a short robe over her underwear but did not bother to tie it, she sat with me on the couch, the robe gaped open again revealing her bra covered tits, as I handed her a glass of wine I couldn’t help myself staring at them, the darkness of her nipples showed through the thin, gauzy material and again I felt my dick start to harden. I felt myself blush when upon looking up our eyes met and Karen smiled, she knew what I had been doing but made nothing of it, she made no move to cover herself, just sat back and watched the TV. Christ! What was happening to me, I have lots of girlfriends, dates are no problem and sex is always there when and if I want it so why was I acting this way over my sister!

Next day at work Bill, my boss invited me to a party he was giving the following Saturday evening, this was a first for me, I knew then that in order to get on in his firm getting invited to one of his parties and making a good impression would be a step up the ladder so to speak. I knew that he sometimes invited people who were in line for promotion to check them out, socially. Another thing I heard was that Bill and his wife were ‘swingers’, a guy I know at work told me that he had been invited to one of Bill’s parties once. He said that Bill had openly come on to his girlfriend, apparently Bill had took her to one side and told her of his and his wife’s ‘open’ marriage, he said his girlfriend told Bill to ‘fuck off’ after Bill had tried to ‘feel her up’. While he was there he told me he saw plenty of couples separate and disappear with different partners, “Bill’s wife Joan had plenty of guy’s to choose from that night I can tell you, they were all over her” he went on, “Bill knew what she was doing but he was busy chatting up any woman he though he stood half a chance with” He told me that he was sure he did not get the promotion he was expecting down to the fact that his girlfriend didn’t play up to Bill’s advances. If he was telling the truth or trying to ‘wind me up’ I didn’t know. I phoned and invited a girl I knew called Debbie, she would be perfect for such a party, I knew that she wouldn’t let me down, a very classy girl who was great fun to be with. I knew that if I asked her she would go along with whatever I wanted, even if that meant getting chatted up by Bill.

When I got home and told Karen about my invite to my boss’s party she was a bit put out that I had not asked her, “I would have gone with you” she said, “Why didn’t you ask me, did you think I would have embarrassed you? Is that it Stuart, do you think I’m not good enough!”

“It’s not that Karen, I would have loved to have you with me, really, but…” I went on to tell her about what I had heard about Bill’s parties. “So you see Karen, if this is an opportunity to get promotion, well…how would it look if I introduced you as my sister, what would that make me look like, a guy who couldn’t get a date, someone who had to rely on his sister to accompany him to his boss’s party, and another thing, if Bill is a bit of a dirty old man who gets his kicks by chatting up and trying to get off with young women, well…do you honestly think I could sit back and watch that, watch him mauling and slobbering over you. I’d end up hitting the guy and then – ‘Goodbye job!’ Christ! What sort of a brother would I be if I was to ask you to ‘be nice’ to my boss, go along with whatever he wanted or whatever he did?.”

“Look Stuart, I know how to handle dirty old men…I’ve made a lot of money out of it! I’d have Bill eating out of my hand by the end of the night and as for promotion, I could just about guarantee it! If what you’ve told me is true it would be his wife, what’s she called – Joan wasn’t it? Well…she’s the one you’d probably have to take care of if you know what I mean” she said, smiling a mischievous smile.

“Are you sure Karen? I mean…You’d do that for me?…You know, probably it’ll turn out to be a boring, ordinary party…ordinary people. I reckon what I’ve been told about Bill is a load of crap, that guy who told me…he was just winding me up, trying to make me nervous” Karen leaned forward and kissed my cheek, “You’ve been good to me Stuart, you have not judged me on how I’ve lived my life, of course I’d do it for you, you just wait, whatever happens I’ll make sure Bill knows how good a guy you are and if there’s a promotion going I’ll try my best to make sure you get it” she smiled. “I won’t let you down…I promise!”

I gave Karen a wad of money, “Why don’t you go shopping tomorrow, get yourself something nice to wear” I phoned Debbie and cancelled our date. Saturday Karen spent ages getting ready, when she eventually emerged from the bedroom I was stunned, she looked gorgeous, beautiful…so sexy! Her black dress clung to her like a second skin, it was fairly short, low cut and just a little bit see through. I could just about make out the darkness of her stocking tops through the thin material. Evidently she was not wearing a bra as I could see her nipples jutting out. “Wow!…you don’t think it a bit, well…too revealing do you?” I asked then added, “Are you wearing ‘any’ underwear?” as I took in the fact that I could not see any sign of panties at all. Karen twirled around and struck a model’s pose, a very sexy pose indeed! “With this dress…do me a favour!” Karen smiled, “It clings so tight that even a thong would be visible, and no…I think it reveals just enough!.”

“Are you sure you want to do this Karen?” I asked, “C’mon, let’s go and meet your boss” she replied, picking up her coat. Twenty minutes later we were greeted by Bill and Joan, on her insistence I introduced Karen as my fiancée. We mingled with the other guests; my first impression of Joan was that of a very classy, beautiful woman in her early forties. She, like all the women present was wearing a very nice outfit and my thoughts of Karen’s dress being too revealing soon disappeared. As we chatted to other guests Karen really got into our loving, couple to be role, she held on to me tightly when we danced and it was as we finished a dance that we were approached by Bill and Joan. We went with them to a quiet corner, “I’ve been hearing good things about you Stuart” Bill smiled, “I invited you tonight to check you out for myself and I like what I see” his eyes went to Karen then back to me, “Yes..I like what I see! I’m going to fix up a meeting for us next week, ok with you?” he grinned. I told him that would be great. We made small talk for a few minutes, I could see him eyeing up Karen constantly, Joan must have realised it but didn’t seem bothered. Then he just matter of factly said “Ok…how about swapping partners” I spluttered on the drink I had just swallowed, “Sorry…I didn’t quite catch that”

“For the next dance…If you don’t mind that is” he smiled at Karen. Karen stood, “Not at all Bill, I’d love to” she told him. He took her hand and together they went to the dance area. Now I was left sitting with Joan, I offered to dance with her but she told me we’d dance later, “Let’s just sit and talk” she smiled. “I think Bill’s got big plans for you Stuart, he’s been watching you for some time now, he told me… and if you play your cards right who knows how far you’ll go in his firm, he’s always on the look out for liberal minded executives” As she told me this she put her hand on my thigh and rested it there. “Bill’s the type of man who knows what he wants and when he’s made up his mind on something he normally gets it” I decided to play along with her, “And how about you Joan…how would you describe yourself…what type of woman are you?”

“Oh…I’m very alike Bill in a lot of ways!” As she smiled her tongue dipped out and she ran it suggestively around her lips, she looked towards her husband dancing with Karen then back to me, “He seems to be enjoying Karen’s company, she’s a very beautiful woman, have you two been together long?”

“Yes, we’ve known each other for many years” I replied. She gave my thigh a squeeze and rubbed her hand over it, “Ok Stuart, I think I’ll take you up on that dance offer now” she grinned. A slow record was playing and as we danced she pressed herself tight up against my chest, I felt her tits push into my chest as she draped her arms over my shoulders, I held on to her as she rested her head on my shoulder. Bill held Karen tight as they danced, she too had her arms draped around him and I saw him squeeze her ass a few times, they were talking to each other as they danced and every now and then I would hear Karen laugh out and saw her playfully slap his arm as if rebuking him. The smell of Joan’s body and perfume close to me and the feeling of her tits against my chest made my dick start to harden, she must have felt it as she ground her hips forward, she looked into my eyes and smiled a knowing smile. It seemed that even though no words were spoken we communicated with each other just by eye contact! The record stopped and we parted, Joan took hold of mine and Bill’s arms and I held Karen’s hand as we returned to the seating area. It was getting fairly late, a few of the guests had left, Bill handed us drinks, “You both wait there, Joan and I will get rid of the others as soon as we can…back soon”

As soon as they were gone I asked Karen what they had talked about, “Well…you were right about him that’s for sure” she grinned, “Christ! He’s a sex maniac, he just didn’t stop trying it on with me, how about Joan, I saw her talking to you, what did you two chat about?” she asked. I told Karen what Joan had said, “Well, it looks like they both want the same thing then” Karen grinned, “Sex!”

“What if we’re wrong Karen, maybe they are just being friendly!”

“Yeah…sure friendly! Look… trust me Stuart, just remember, tonight I’m not your sister, right! Bill knows we love each other but I’ve told him that we are not the jealous type, we respect each others feelings but we are a modern, liberated couple who like to have fun. Let’s just go along with whatever happens…ok!”

Twenty minutes later after the others had left and Bill and Joan returned, “C’mon you two, we’ll go into the den, we can carry on our talk there” Bill told us. There were two large sofas, I sat on one and Joan sat next to me as Bill took Karen to fix drinks. Joan turned to me, “Stuart, I think you know why we asked you and Karen to stay, Bill and I, well…we have a close, intimate circle of friends and we were hoping you two would want to join that circle” she reached out and took hold of my hand. “Do you find me attractive Stuart?” she asked, “Of course I do” I replied, “What man wouldn’t!” Joan went on “Bill feels the same about Karen, he thinks she is very sexy, he’s taken quite a shine to her… how would you feel about you and Karen, you know…getting on a more intimate level with Bill and me?” she asked. “I can’t speak for Karen Joan, I would have to ask her”

“Would it surprise you Stuart if I told you that Karen had already been asked the same questions, would it shock you if I told you that Karen had made it clear to Bill that she was well…more than keen shall we say!”

“No…I guess it wouldn’t surprise or shock me at all” I replied. “Good, that’s what I wanted to hear” Joan said with a smile, with that she leaned forward and kissed me on my lips. As we were kissing Bill and Karen returned, Bill made nothing of seeing me kissing his wife and then after handing us our drinks Bill and Karen sat opposite us on the other couch. “So…it looks as if you two have got to know each other, have you enjoyed our little party Stuart?” Bill asked, “Very much Bill, thank you for inviting me” Joan had now slid up close to me and held my hand as it rested in her lap. Bill openly slid his arm around Karen’s shoulder his hand casually hung at the side of her tit, Joan turned to me and speaking quietly she said “Kiss me Stuart” I did as she asked and within seconds we were deeply, passionately kissing, sensing my hesitance she took hold of my hand and guided it up to her tits. She rubbed her hand along my thigh until it rested on the bulge in my pants, gently squeezing and stroking my dick as it swelled in the confines of my trousers.

Everything was happening so quickly, her nipples hardened as I played with her tits through the thin material of her dress, I glanced across and saw Bill and Karen kissing, he had his hand up under her dress, she had her legs spread wide open and I heard her moan and it appeared he was fingering her pussy. Joan undid my belt and unzipped my trousers, she pulled out my hard dick and started to play with it then, lowering her head she took my dick into her mouth and slowly began to suck on it. Karen was now laid back on the couch, her dress was up around her waist and Bill had his head between her legs, his tongue licking at her smooth pussy, his hand was busy playing with her tits, Karen saw me staring at her and just smiled at me.

This was weird, here I was getting my dick sucked by my boss’s wife and my sister a few feet away having sex with some guy she had only met a few hours ago, the weird thing was I was getting turned on, not only by the blowjob I was receiving, no…It was the sight of my own sister having sex! Joan stood up and pulled me to my feet, as we kissed she unbuttoned my shirt and soon I was naked, she slipped the straps of her dress off her shoulders and it dropped to the floor, she too was now naked apart from her black stockings and sexy suspender belt. Joan lay back on the couch, one foot on the floor, and the other draped high over the back of the couch, her legs wide open, her glistening pussy lips wet from her juices.

Her pussy was shaved smooth apart from a tiny tuft. Her large tits with their big, brown nipples beckoned me to play with them but Joan wanted me to lick her pussy. I kissed her, then slowly working my kisses lower and lower, over her tits, her stomach I reached her pussy, she moaned loudly and gripped my head with her hands as my tongue flicked over her pussy lips, I dipped my tongue deep inside her wet cunt licking at her juices, I used my fingers and my tongue as she cried out, her body shook and her she pushed her hips forward to meet the thrust of my fingers.

Again I looked over to Karen, they both were also naked apart from Karen’s black hold-ups, she was knelt in front of Bill and was sucking on his dick, he held her head as he fucked her mouth deep. I positioned myself in between Joan’s legs took hold of my dick and rubbed it over her pussy then slowly I entered her. Although she was wet her cunt was very tight and she moaned with pleasure as I buried my hard dick deep into her cunt, I could feel her cunt muscles grip the shaft of my dick, a sort of pulsating sensation. Joan was a very vocal lover, she moaned and groaned loudly as I fucked her, I kept looking across, Bill was now sitting on the couch and Karen was facing me as she bounced up and down on his dick, he had both hands cupping her tits, tweaking on her nipples. Again Karen smiled at me as she saw me looking at her.

I fucked Joan deep and hard for some time, eventually I felt my dick start to swell and seconds later I emptied my cum in her cunt, I stayed inside her, my dick twitching and throbbing as she contracted her cunt muscles, milking out every drop of my cum as it dribbled out. Karen was now laid on the carpet, Bill was fucking her hard, my dick softened and I pulled out and sat back on the couch, my eyes fixed on my sister as she got fucked. Joan rolled off the couch and crawled over to Karen and began to feel her tits, she lowered her head and sucked on her nipples then she kissed her. Fuck! It looked so erotic seeing them kissing each other.

Bill fingered Joan’s cunt as my cum dribbled out of her, Joan turned to me and waved me over. I knelt beside Karen’s head as Joan took my now hardening dick back into her mouth, I couldn’t resist it, I knew I shouldn’t with Karen being my sister but I reached out and cupped one of her firm tits in my hand, again Karen looked up to me and with a little nod of her head she smiled. I rolled her hard nipple between my fingers and watched Bill’s dick slide in and out of her smooth pussy. What happened then I’ll never forget as long as I live. Bill pulled out of Karen and quickly slid his dick into his wife’s cunt as she sucked on my dick, Karen got onto her hands and knees and swivelled around so her pussy was facing me, “Fuck me Stuart!” she panted, without a second thought I pulled out of Joan’s mouth and I plunged my dick deep into my sisters sopping wet cunt.

Bill fucked Joan for a while then he knelt at Karen’s head for her to suck on his dick I as fucked her, Joan lay on the floor with her head under Karen and played with her tits as they hung beneath her at the same time she fingered herself. We all swapped around, Karen sucked my dick, I and Bill fucked them both in various positions, Joan licked and played with Karen’s pussy and she in return did the same for Joan. I was amazed at Bill’s staying power, he had been at it for ages and eventually he shot his cum into Karen’s eagerly waiting mouth, I saw her swallow his cum and lick and suck him dry. Joan received my second load of cum in her mouth also.

After a couple of drinks and a bit of a breather we were all at it again, both Karen and Joan took our dicks in their cunts and asses, it was actually Karen who told me to fuck her ass while Bill was fucking her cunt, eventually we were all exhausted, Bill invited us to stay the night, I slept with Joan, he with Karen. Over breakfast I had mixed emotions, I had serious pangs of regret but on the other hand the sex I had last night had been the best sex I had ever experienced, it truly was a night I would never forget.

I made small talk, I tried to act as normal as possible but avoided eye contact with Karen, Karen and I did not really discuss what had taken place till we got home about midday Sunday, truthfully I didn’t really know what to say, we hardly spoke during the drive home, my head was spinning, it was Karen who bought it up. “So, c’mon…I think you and I need to talk” she said, “Yes, I suppose we do” I replied. “Didn’t last night turn out as you hoped it would, did you not enjoy what happened?” she asked “Yes…No…, I don’t know, that’s just it really, how it turned out, what we did…you and me, things just seemed to happen, Christ Karen! You’re my sister…we shouldn’t have…”

Karen sat back in her chair, “So that’s what this is about, you’re on a guilt trip, you regret what we did, No!…I don’t think so Stuart, why can’t you just admit it…admit that you enjoyed it, go on…admit that you enjoyed fucking me!” she shouted.

“Ok Karen…I admit it…I enjoyed it, I enjoyed fucking you! There…does that make you happy!” I shouted back. It went quiet for a couple of minutes, then Karen said “You know something Stuart, I’ve had sex with loads of guys, I can’t remember most of them and truthfully I don’t want to but last night, last night I can honestly say I felt something that I have never felt before. Sure…sex with Bill was great, he certainly knows how to treat a girl but when…, when I had sex with you it was different, I don’t know how to explain it but, for the first time I felt loved! So what if we are brother and sister, big deal! I can handle it, I’ve always loved you as a brother and now, well now I love you as a lover as well! I could leave now Stuart and there would be a good chance that you would never see me again, is that what you want, is that what you really want?”

I turned to her, “No…No Karen, I don’t want you to leave, I want you to stay” I held out my hand, Karen took it and I pulled her up, we stood facing each other looking into each others eyes and we kissed. We didn’t speak as hand in hand we walked to the bedroom, seconds later we were both naked and we spent the afternoon making love – No, I couldn’t call it sex…this was all about love!

True to his word Bill gave me promotion; I am now a marketing director. Karen and I saw Bill and Joan a lot over the next three months. Karen and I slept together and we enjoyed great sex but then one day she told me she was going to leave, she wanted to follow her dream of tripping around Europe. I was shattered and begged her to stay but her mind was made up, she promised me she would keep in touch and told me that if and when she returned we would see if we still both felt the same way about each other, then take things from there.

I introduced Debbie to Bill and Joan and still to this day get together with them fairly regularly. I have received many letters from Karen, she seems to be having a great time, she writes that she misses me and I hope and pray that one day soon she will return.

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