Rough Trade
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Before you start...this is quite a long story, but please have patience. Thanks.
Cindy’s ice blue eyes stare deep into mine, a rock solid, unflinching gaze. I get the impression she is not going to deliver good news.
“Rob, I won’t hold back, you’re a dear friend and I care about you. I think your accounts are a wreck, and your projected figures for the next year do not inspire confidence at all. If I am brutally honest, your business might not even be around for that long anyway.”
Talk about not sugar coating the pill, the words chill my spine and cause me to perspire at the same time. I know things hadn’t been going swimmingly, but I didn’t expect to hear my livelihood might be falling apart all around me.
Cindy is my accountant, not to mention a former partner. I know she has my interests at heart, so I can’t disregard her opinion or bury my head in the sand. I have worked so hard to get this business up-and-running, and it fills me with despair to face failure.
“What do you suggest then, Cindy?”
She raises her eyes skywards for a moment then back on to me.
“I don’t know. Let a few of your staff go, reduce your prices, advertise more. Common sense really.”
I muster a smile from somewhere and tell her I could always get a cheaper accountant.
“You could, Rob. But I bet they wouldn’t stand for you staring at their legs or breasts all the time.”
Her glowing smile melts me, it never fails. I feel she might have a point as well.
“Guilty as charged, but you know what your legs and tits do to me.”
Casting aside my worries for a minute I stand and approach her casually unzipping my jeans and letting them fall, my erection standing proud in my boxer’s. Her eyes move from my face to my crotch and her painted nails stroke my cock gently through the material.
“I see the merchandise is still good quality, some things don’t change.”
I move her hand away for a second and ease down my underwear, my erect penis inches from her face.
“Go on, please Cindy. I could really do with something to ease the tension. Just this once, for old time’s sake. Please?”
She sighs deeply, giving me a look somewhere between pity and admiration for my bare faced cheek.
“Every time I fall for this. Every damn time. Oh and I haven’t forgotten, you still haven’t paid me for last month’s visit, let alone this one.”
Her fingers gently ease my foreskin back and she leans forward. Her mouth devours three quarters of my length in one go. My hands grasp her head and push her deeper onto my girth. This isn’t going to take long.
Cindy returns from the bathroom, suitably freshened up and looks relieved to see I have made myself respectable again. I was right, it didn’t take long, truth be told it never did. Her sweet mouth and swirling tongue always work for me, coaxing my orgasm within four or five minutes as a rule.
“You do realise times are hard for accountants too, Rob. I do normally draw the line at sexual favours you know. It’s only because we have history and...
She breaks off, not finishing her sentence.
“And what, Cindy?”
“You do have a nice cock, but don’t get big headed.”
I thank her for the compliment and tell her to send me her invoice.
“Rob I have a little idea for you. I know how much your business means to you and I would like to help. My mother is something of a commercial networker, as I’m sure you remember?”
I nod, recalling her formidable mother.
“Well, she’s having one of her get-together’s at the old house. I know that there are usually a lot of players in the local business world there. Why don’t I try and swing you an invite? It might help you out a little.”
I tell her to get me on the list at any cost.
“I’ll do my best. You will owe me big time if I get you in, agreed?”
I smile and tell her it’s a deal.
“I’m too good to you, Rob. You better be ready to thank me some day real soon.”
Her words are still in my head as I hear the door slam shut and I’m left standing alone.
*
Three days pass without a word from Cindy. I try my best not to think too deeply about my plight, but I feel the weight of guilt on my shoulders. The people I employ have come to be more friends than just people I pay a salary to. I would feel an enormous sense of failure if I have to make these people redundant as they have all worked so hard for me.
Three years it has taken to establish my business. It had started as a part time money earner based in a friends garage, but I stuck at it and steadily made it a success. Eventually many independent shops were stocking my men’s underwear range. I expanded the business and moved into expensive new premises, things were going well until the global financial crisis took hold and I find myself looking at the possibility of going under.
Finally, the next day Cindy calls. She has twisted her mother’s arm and managed to get me an invite to her meeting the following evening. I thank her for her help, she laughs heartily down the line, reminding me that I am forever in her debt. It doesn’t give me much time to prepare, but I have to grasp my chance.
I can’t say that I ever really saw eye to eye with Sylvia. In the short time that I officially dated her daughter, she never looked upon me with anything other than mild indifference. It was the classic case of not being good enough for her precious Cindy. On the occasions I had met her since our split she had always managed to belittle me and inform me what a lucky escape her daughter had when we decided to break up. I would never entertain the idea of being civil towards her but she does hold a certain power within the local business fraternity, having been a leading light in the local Chamber of Commerce for several years. I have to swallow my pride and bow to her superior networking and powerful contacts. It’s a dog eat dog world, and I have to survive, by any means necessary.
I approach the old house with trepidation, memories flooding my brain. I climb the steep, never ending steps and across the courtyard to the front entrance. I am greeted at the door by Chambers, the ageless butler who I remember from yesteryear. He seems to recall me, smiling faintly before taking my coat and the package containing a sample of my merchandise. He leads me through the grand hallway and into the ballroom; yes Sylvia has a ballroom! The room is already full and I feel severely underdressed in just a shirt and casual trousers, nearly everybody else is in formal dress.
Chambers announces me to Sylvia, who greets me with an uncharacteristic kiss and embrace, I suspect she has already had a few refreshments as she is usually not an advocate of any physical contact.
“Robert, my dear boy. How the devil are you? It’s been such a long time.”
She clicks her fingers and ushers over a devastatingly pretty black haired girl with the most amazing soft brown eyes and warm smile. I stare at her, not meaning to gaze for so long, but I can’t stop myself. She looks at me, but doesn’t seem to take me in.
“Evie, could you get Robert a drink please? Vodka and lime, plenty of ice if I recall.”
I nod and tell her that would be lovely. Evie swishes past me, her eyes catching mine this time, returning moments later with a crystal cut glass full to the brim. She holds it out to me with a very steady hand. I thank her and gulp back half of the drink in one go, needing the Dutch courage.
Evie walks away and I admire her firm rear, and the wiggle in her walk. I may just try my luck later. My daydream is shattered abruptly by Sylvia’s heavy sigh.
“Oh Robert, my dear Robert. You always did have an eye for the ladies, Cindy always complained about that. I see you haven’t improved with age.”
Suitably reprimanded I decide to make forced small talk with boring people who, by and large are of no use to me at all. Only one woman, a buxom mid forties blonde called Pippa seems to think she had a contact who might be able to sell my product, but there is nothing definite. She leaves me with a business card and tells me to call her in a couple of days. I sigh inwardly and tell myself it’s better than nothing.
After an hour I’ve had my fill. I grab a bottle of beer from the kitchen and make my way to the terrace for a cigarette. The night air is cool and the light is beginning to fade. There are a handful of people outside including Evie who is collecting glasses, balancing them skilfully on a tray. She glides past me, once again we share prolonged eye contact, before I ask her if she has a bottle opener.
Evie places the tray down, takes my bottle and dispatches the top, handing it back to me with a sweet smile. I light my cigarette and ask if she would like one. She tells me she shouldn’t as Sylvia wouldn’t approve.
“Maybe later then, when you’ve finished?”
“Maybe yeah.”
She leaves me enjoying my smoke, and the peace of the sunset. My solace is quickly shattered by Sylvia, who seems to delight in getting under my skin.
“Ugh, you still persist with that filthy habit. I’m so glad Cindy saw you for what you were. What you still are for that matter.”
My patience snaps, I have had enough.
“Well to be honest Sylvia, having you as a mother-in-law would put all but the bravest man off anyway.”
She looks at me in disgust, not used to anybody talking back to her.
“Well, thank you for that glowing tribute. I came to tell you that Pippa seems to like you, thinks she can help you. God know quite why she would want to. You’re just an ignorant little shit.”
We stare at each other, full of mutual contempt.
“She is coming here next Tuesday for lunch, wants to meet up with you to discuss a possible business link up. I’ve shown her the samples that you left and she is impressed. You’re incredibly lucky that I agreed. However, I am aware that you owe my daughter money, so it’s in my best interests to help you, however much I loathe you. So next Tuesday at mid-day. Do not be late.”
She turns and walks off, stopping at the doorway to address me once more.
“Oh and Robert, forget about Evie, she is off limits. Not up for discussion I’m afraid.”
As she disappears I tell myself we’ll see about that.
*
Tuesday eventually comes around, it’s been an edgy few days spent trying to drum up new business without much reward. I can only hope that Pippa will be my salvation. I make my way to Sylvia’s house telling myself not to rise to her bait today. I’m going to have to be on my best behaviour.
Chambers shows me in to the reception room and tells me to take a seat. I feel a little nervous as I wait, needing this to go to plan. I need some positive news as business is still poor. After what seems like a lifetime Chambers beckons me to follow him, and leads me ponderously into the cavernous lounge. I am surprised to find it is unoccupied, I was expecting to see Sylvia looking down her nose at me. Chambers tells me to take a seat and he will inform Madam that I have arrived. I take in his features, the usually unflappable servant seems ruffled and ill at ease for some reason. He hurries away leaving me in solitude. I hear his footsteps on the creaking stairway, maybe Sylvia had one too many Gin’s last night and is taking a nap.
Five minutes pass and I’m still sat alone, this only adds to my nerves. Perhaps this is some ploy by Sylvia, nothing would give her greater pleasure than to make me suffer.
Finally I hear two sets of descending footsteps and then Sylvia’s booming voice telling Chambers that he wouldn’t be needed for the rest of the day. Her entrance isn’t full of it’s usual bombast, in fact she too looks flustered, and most unusually her hair looks quite dishevelled, and her clothing untidy.
“I’m sorry to have kept you Robert, I was a little distracted, lost track of time completely. Why don’t you come upstairs? Pippa is already here, she’s taking a look at the samples that you left behind in greater detail.”
We make our way up the grand staircase without speaking before she shows me into a plush bedroom. The sight which greets me near enough knocks me off my feet. Pippa is naked on the giant bed, legs spread wide apart, knees bent. Her hands are clasped around the head of Evie who is also naked except for a pair of boxer shorts, which bear my logo. Neither acknowledge my entrance, both engrossed in each other. I admire Evie’s beautifully tight buttocks encased in the tight cotton. Her fingers frantically sawing in and out of Pippa’s glistening pussy. Pippa’s moans increase as Evie’s tongue swirls against her clit, lashing it back and forth.
“Fucking hell.”
Not clever, but that is the only thing that I can say. The sheer enormity of what I was trying to digest was too much for my brain. I stand just engrossed for at least two minutes as Pippa’s orgasm approaches, then rips through her body, Evie’s skilled tongue doing it’s work. I can feel my erection growing quickly, no way can I restrain it. Evie continues, her tongue and fingers reducing in intensity, bringing Pippa down slowly.
“My my, don’t your boxer shorts look divine on Evie?”
I had even forgotten Sylvia was in the room, such was my concentration on the bed. Even now she cannot crack a smile or show emotion.
“Tell me Robert, do you wear your own produce?”
Lost for words I just nod, my mouth hot and dry.
“Well, let’s see shall we?”
Without another word Sylvia undoes my belt and unbuttons my jeans, yanking them down to my thighs, revealing my shorts. My erection is now almost full stretch, making a huge bulge, straining to be kept confined. Three pairs of eyes are now fixed on me. Sylvia calmly pulls the shorts down exposing my aching cock, standing proud.
Sylvia’s slender hand caresses me, pulling back my foreskin then gently stroking me back and forth. After a minute or so my dick is pulsing and impossibly erect.
“Cindy always said that this was the best part of you.”
Her technique is good. Slow long strokes along my lengh, thumb brushing against my sensitive glans. Evie and Pippa are watching intently.
“You like Evie don’t you Robert? I saw you the other night, you couldn’t take your eyes off her. You’d like to fuck her wouldn’t you? Like to fuck her tight little pussy?”
“Fuck yes, I really want her, Sylvia.”
“She wants you too, she told me. Heaven knows why, but she does. Don’t you Evie darling?”
Evie smiles sweetly and acknowledges with a delicate nod.
“Well I will allow you, even though you are mine. You have been a good girl lately, and it must get boring trying to coax anything from Chambers. The man has gone to seed.”
“Thank you, Mistress.”
“But not before I’ve sucked his cock. I’ve wanted to do that for so long. Pippa, get my girl ready for him. Make her nice and wet.”
It’s hard not to laugh hearing Sylvia talking dirty with her clipped accent and sophisticated tone. So despite the hard faced image, she has always wanted to suck my cock, what a revelation. I don’t have much time to reflect on this nugget as Sylvia is busy stripping me off, her nails raking my skin as she tears off my shirt, her tongue briefly sucking at my nipples. She has me naked within a minute and is on her knees sucking me off with gusto, taking my length with consummate ease, coating my length with her saliva. Her left hand massages my sac and it’s all too much, her skill is immense and I can’t hold back, spilling my come deep down her throat before she pulls me out of her mouth and allows the last of my load to splatter all over her nose and cheeks. I’m breathing heavily, savouring the moment.
Syliva scoops my semen from her face and licks it off her fingers, not wasting a drop. She must like it as she squeezes the huge droplet of cum from my dick onto her waiting tongue and swallows it down.
“Mmmm, your cum tastes so much nicer than Chambers. That will be all for now, Robert. My Evie is waiting for you.”
And that was it, just as if it was a transaction, no emotional attachment whatsoever.
Pippa certainly seems to have got Evie in the mood, judging from the noise she is making. Her eyes shut tightly as she is fingered hard by the more experienced woman. Sylvia picks up the discarded boxer shorts and takes in the aroma of Evie’s scent. Her eyes flicker and I swear that she shivers ever so slightly.
“Pippa, that’s enough now. I want to see Robert fucking her. Awfully well done though, she looks like she is sopping wet.”
Pippa moves off the bed, almost forlornly. I sense that she wanted to make Evie climax. Sylvia is right though, her pussy is glistening and swollen, and looks delicious. My flaccid penis is soon making it’s way back to full erection, I want Evie so badly, and the thought of Pippa and Sylvia watching makes the whole situation so much more erotic.
“Go on then Robert, fuck her, right now. I want to see her on all fours, and I want you to fill her tight little cunt.”
I sigh inwardly, so I’m going to be fucking her as per Sylvia’s instruction then.
“Spank her ass first, she loves that. You do want that don’t you Evie sweetheart?”
“Yes Mistress. I do.”
I roughly grasp Evie and push her onto her knees before giving her time to think my outstretched hand crashes against her pert derriere. She gasps and takes a sharp inward breath. I quickly repeat my action, and then again. Her wimpers are half pain and half pleasure. A couple more blows and my hand mark is imprinted on her flesh and it gains a ruby red hue.
“Enough. Fuck her. Fuck her now.”
I decide to defy Sylvia and spank her once more, causing Evie to yelp.
“I won’t tell you again, Robert. I want you to screw her hard.”
I crudely push Evie’s knees further apart and then tease her puffy lips wide, causing her to gape a little. She has such a neat and pretty shaven pussy, truly adorable. I gently hold her hips and guide myself inside her, slowly at first as she takes my bulbous head. She gasps a little as I penetrate her.
“HARD I SAID. FUCK HER HARDER.”
Sylvia is beginning to piss me off now.
I thrust hard and bury my bone hard cock deep inside Evie, making her cry out, her fingers digging into the bed sheets, a contorted look on her face, teeth gritted. I think she isn’t enjoying it, but it seems I’m mistaken.
“Fuck me, really give it to me. I’m so gagging for it. Fuck me like the slut I am.”
Sylvia pipes up, telling me to do as I’m told.
I redouble my efforts, now gripping her hips with force, pushing her hard onto my dick, then pushing her off, then back on harder still. Her juice slathered all over my length as I make the bed rock and creak with my motion. Evie is loving it, now hollering the walls down, especially now my thumb is circling her clit rapidly, clockwise, then anti clockwise. The incredible slap of my balls against her ass adds to the ambience of our fucking.
Possibly due to Pippa’s ministrations earlier, Evie comes quickly, violently. The bed, the walls, the whole room shakes as she reaches a tumultuous orgasm. She spurs me on and I fuck her even harder as she rides out her climax. I shift position and move forward, cupping her breasts, touching her stubby nipples as I feel my come rising again. I can’t hold back, her vice like grip makes it impossible. I grunt loudly and spurt another huge load, deep inside Evie.
The feeling is like nothing else, so bloody good. I’m spent, collapsing on top of her, both of us breathing heavily. I hold her in my arms, kissing her neck and ear, before she tilts her head and gives me a breathless kiss deep on my lips, her eyes burning into mine. She deftly wipes tiny beads of sweat forming on my brow, affording me a stunning smile.
The intimacy of the moment is shattered, unsurprisingly by Sylvia.
“That’s enough thank you. No kissing. I didn’t say you could kiss did I?”
I notice that Pippa is no longer in the room, she must have gone to freshen up.
I kiss Evie’s forhead and withdraw myself from her, my semen trickling out of her as I do. I go to retrieve my clothes, my path suddenly blocked by Sylvia.
“Did you enjoy that, Robert? It certainly looked that way.
“Evie is beautiful. It was wonderful. Thank you.”
I bend to pick up my garments, Sylvie’s hand pushes against my chest, blocking me.
“Where do you think you are going, Robert? Your afternoon isn’t over yet.”
I stare at her, puzzled, nonplussed.
As if on queue Pipa reappears, naked. I say naked. Naked except for a striking black shiny strap-on. The penny drops.
“Oh no, no. Absolutely no fucking chance, Sylvia.”
“Well, how can I put this. Be fucked, or you’re fucked. Without Pippa’s contacts, well you’re screwed anyway. Pardon my crudity.”
A sinister smile plays on Sylvia’s face.
“Take it like a man. Who knows, you might like it. Chambers does. He positively loves it.”
I’m beginning to think whatever she pays Chambers, it’s not enough.
“One word, Robert, lubrication. You’ll barely feel it. I promise.”
Without another word she pushes me back onto the bed, with Evie’s help I’m manoeuvred onto all fours. I feel the cold splurge of lubey against my anus, and then Evie’s fingers gently probing me, pushing her thumb deeper inside me. This doesn’t feel too bad at all, in fact I could get to like it. Sadly it doesn’t last and her fingers are replaced by the cold ruthless rubber of the strap-on.
Once again Sylvia is directing operations.
“Give it to him, Pippa. Fuck him hard. Make him work for the business you’re giving him.”
The incredible pain as Pippa attempts to push the head of her appendage inside me brings tears to my eyes. Fuck, is this worthwhile? Is money worth the pain? Thankfully Pippa does go a little easy, sensing my reticence. She slows and nudges slowly against me, eventually I yield and the cock is inside me. I grit my teeth and come to terms with the girth, thanking my lucky stars for the lube. Evie creates a welcome diversion, reaching under and stroking my cock gently, bringing it back to life.
Now two inches inside me, Pippa decides that’s enough of the gentle touch, seemingly trying to get the whole six inches inside me in one go, it’s just not going to happen. I try and tell her to stop, but I find Sylvia’s hand covering my mouth, muting me. Pippa thrusts deeper and finds my g-spot. The pain subsides a little and is balanced by pleasure. My dick jolts, instantly hardening, aided by Evie now taking my veiny shaft into her mouth, swallowing me deep.
I’m being fucked hard now, starting to enjoy it a little. Pippa strokes my sac as she pounds me, giving me increased pleasure. The enjoyment just about outweighing the pain, and to see Sylvia now seated by the bedside, legs apart, panties pushed to one side masturbating with wild abandon just tops everything off. Her pussy is hairy and unkempt, her fingers wildly strumming her clit. Her stuffy image is kicked into touch as she orgasms violently, squirting a huge arc of liquid into the ether. I feel I’m going to wake up any second and realise this is all a dream.
The proximity of three aroused women is too much, the smell of sex fills the room. Assorted gasps and sighs meld into one huge sound and a final thrust of the rubber cock makes me explode, my length fully inside Evie’s pretty mouth. Spurt after spurt of creamy cum spills out out me. It’s too much volume and my cream trickles out and onto her lips, she withdraws me at the same time Pippa leaves my anus empty. Once again I crash onto the bed, totally expended this time.
I must have crashed out for a few minutes. I’m revived by a glass of water...thrown into my face courtesy of Sylvia. The emotion and sexuality she showed earlier, definitely was a one-off.
“Time for you to go. You have served your purpose here. Goodbye Robert.”
*
Four weeks later and I’m snowed under. Orders are flying in from all corners of the world. I’m selling underwear quicker than I can make it. New premises and more staff are in the pipeline. Every time I see a pair of my trademark boxers, in a white, small size I can’t stop myself thinking about Evie and our amazing time together. I have contacted her and look forward to meeting up, if she can escape the clutches of Sylvia.
A knock on my office door, I’m not expecting anyone. I open up and find Cindy looking at me. I usher her inside and take the envelope from her. An invoice for her services.
“I trust my mother was able to help you out then?”
“Oh you know, she has her uses.”
Cindy moves forward, a wry smile on her face.
“So she tells me. Evie and Pippa too. Sounds like you all had a fabulous time.”
I’m shocked. I didn’t think Sylvia would divulge such information.
She moves closer, her face inches from mine. I feel her hand unzipping my flies, working it’s way inside my shorts. She gently coaxes my dick to life. Looking me square in the face, her piercing eyes glinting.
“So, how is your ass? Can you sit down without a rubber ring yet?”
I smile and tell her I’ll survive.
“Oh, and by the way, Cindy. There’s something I need to ask you.”
“Go ahead. What do you want to know? Only make it quick. I’m expecting sex. You owe me, remember?”
“Please tell me Chambers didn’t have you as well? That man seems to be very active for his age.”
Cindy’s gaze leave mine. Her smile fades and her eyes lose their lustre.
The silence is deafening.
Cindy’s ice blue eyes stare deep into mine, a rock solid, unflinching gaze. I get the impression she is not going to deliver good news.
“Rob, I won’t hold back, you’re a dear friend and I care about you. I think your accounts are a wreck, and your projected figures for the next year do not inspire confidence at all. If I am brutally honest, your business might not even be around for that long anyway.”
Talk about not sugar coating the pill, the words chill my spine and cause me to perspire at the same time. I know things hadn’t been going swimmingly, but I didn’t expect to hear my livelihood might be falling apart all around me.
Cindy is my accountant, not to mention a former partner. I know she has my interests at heart, so I can’t disregard her opinion or bury my head in the sand. I have worked so hard to get this business up-and-running, and it fills me with despair to face failure.
“What do you suggest then, Cindy?”
She raises her eyes skywards for a moment then back on to me.
“I don’t know. Let a few of your staff go, reduce your prices, advertise more. Common sense really.”
I muster a smile from somewhere and tell her I could always get a cheaper accountant.
“You could, Rob. But I bet they wouldn’t stand for you staring at their legs or breasts all the time.”
Her glowing smile melts me, it never fails. I feel she might have a point as well.
“Guilty as charged, but you know what your legs and tits do to me.”
Casting aside my worries for a minute I stand and approach her casually unzipping my jeans and letting them fall, my erection standing proud in my boxer’s. Her eyes move from my face to my crotch and her painted nails stroke my cock gently through the material.
“I see the merchandise is still good quality, some things don’t change.”
I move her hand away for a second and ease down my underwear, my erect penis inches from her face.
“Go on, please Cindy. I could really do with something to ease the tension. Just this once, for old time’s sake. Please?”
She sighs deeply, giving me a look somewhere between pity and admiration for my bare faced cheek.
“Every time I fall for this. Every damn time. Oh and I haven’t forgotten, you still haven’t paid me for last month’s visit, let alone this one.”
Her fingers gently ease my foreskin back and she leans forward. Her mouth devours three quarters of my length in one go. My hands grasp her head and push her deeper onto my girth. This isn’t going to take long.
Cindy returns from the bathroom, suitably freshened up and looks relieved to see I have made myself respectable again. I was right, it didn’t take long, truth be told it never did. Her sweet mouth and swirling tongue always work for me, coaxing my orgasm within four or five minutes as a rule.
“You do realise times are hard for accountants too, Rob. I do normally draw the line at sexual favours you know. It’s only because we have history and...
She breaks off, not finishing her sentence.
“And what, Cindy?”
“You do have a nice cock, but don’t get big headed.”
I thank her for the compliment and tell her to send me her invoice.
“Rob I have a little idea for you. I know how much your business means to you and I would like to help. My mother is something of a commercial networker, as I’m sure you remember?”
I nod, recalling her formidable mother.
“Well, she’s having one of her get-together’s at the old house. I know that there are usually a lot of players in the local business world there. Why don’t I try and swing you an invite? It might help you out a little.”
I tell her to get me on the list at any cost.
“I’ll do my best. You will owe me big time if I get you in, agreed?”
I smile and tell her it’s a deal.
“I’m too good to you, Rob. You better be ready to thank me some day real soon.”
Her words are still in my head as I hear the door slam shut and I’m left standing alone.
*
Three days pass without a word from Cindy. I try my best not to think too deeply about my plight, but I feel the weight of guilt on my shoulders. The people I employ have come to be more friends than just people I pay a salary to. I would feel an enormous sense of failure if I have to make these people redundant as they have all worked so hard for me.
Three years it has taken to establish my business. It had started as a part time money earner based in a friends garage, but I stuck at it and steadily made it a success. Eventually many independent shops were stocking my men’s underwear range. I expanded the business and moved into expensive new premises, things were going well until the global financial crisis took hold and I find myself looking at the possibility of going under.
Finally, the next day Cindy calls. She has twisted her mother’s arm and managed to get me an invite to her meeting the following evening. I thank her for her help, she laughs heartily down the line, reminding me that I am forever in her debt. It doesn’t give me much time to prepare, but I have to grasp my chance.
I can’t say that I ever really saw eye to eye with Sylvia. In the short time that I officially dated her daughter, she never looked upon me with anything other than mild indifference. It was the classic case of not being good enough for her precious Cindy. On the occasions I had met her since our split she had always managed to belittle me and inform me what a lucky escape her daughter had when we decided to break up. I would never entertain the idea of being civil towards her but she does hold a certain power within the local business fraternity, having been a leading light in the local Chamber of Commerce for several years. I have to swallow my pride and bow to her superior networking and powerful contacts. It’s a dog eat dog world, and I have to survive, by any means necessary.
I approach the old house with trepidation, memories flooding my brain. I climb the steep, never ending steps and across the courtyard to the front entrance. I am greeted at the door by Chambers, the ageless butler who I remember from yesteryear. He seems to recall me, smiling faintly before taking my coat and the package containing a sample of my merchandise. He leads me through the grand hallway and into the ballroom; yes Sylvia has a ballroom! The room is already full and I feel severely underdressed in just a shirt and casual trousers, nearly everybody else is in formal dress.
Chambers announces me to Sylvia, who greets me with an uncharacteristic kiss and embrace, I suspect she has already had a few refreshments as she is usually not an advocate of any physical contact.
“Robert, my dear boy. How the devil are you? It’s been such a long time.”
She clicks her fingers and ushers over a devastatingly pretty black haired girl with the most amazing soft brown eyes and warm smile. I stare at her, not meaning to gaze for so long, but I can’t stop myself. She looks at me, but doesn’t seem to take me in.
“Evie, could you get Robert a drink please? Vodka and lime, plenty of ice if I recall.”
I nod and tell her that would be lovely. Evie swishes past me, her eyes catching mine this time, returning moments later with a crystal cut glass full to the brim. She holds it out to me with a very steady hand. I thank her and gulp back half of the drink in one go, needing the Dutch courage.
Evie walks away and I admire her firm rear, and the wiggle in her walk. I may just try my luck later. My daydream is shattered abruptly by Sylvia’s heavy sigh.
“Oh Robert, my dear Robert. You always did have an eye for the ladies, Cindy always complained about that. I see you haven’t improved with age.”
Suitably reprimanded I decide to make forced small talk with boring people who, by and large are of no use to me at all. Only one woman, a buxom mid forties blonde called Pippa seems to think she had a contact who might be able to sell my product, but there is nothing definite. She leaves me with a business card and tells me to call her in a couple of days. I sigh inwardly and tell myself it’s better than nothing.
After an hour I’ve had my fill. I grab a bottle of beer from the kitchen and make my way to the terrace for a cigarette. The night air is cool and the light is beginning to fade. There are a handful of people outside including Evie who is collecting glasses, balancing them skilfully on a tray. She glides past me, once again we share prolonged eye contact, before I ask her if she has a bottle opener.
Evie places the tray down, takes my bottle and dispatches the top, handing it back to me with a sweet smile. I light my cigarette and ask if she would like one. She tells me she shouldn’t as Sylvia wouldn’t approve.
“Maybe later then, when you’ve finished?”
“Maybe yeah.”
She leaves me enjoying my smoke, and the peace of the sunset. My solace is quickly shattered by Sylvia, who seems to delight in getting under my skin.
“Ugh, you still persist with that filthy habit. I’m so glad Cindy saw you for what you were. What you still are for that matter.”
My patience snaps, I have had enough.
“Well to be honest Sylvia, having you as a mother-in-law would put all but the bravest man off anyway.”
She looks at me in disgust, not used to anybody talking back to her.
“Well, thank you for that glowing tribute. I came to tell you that Pippa seems to like you, thinks she can help you. God know quite why she would want to. You’re just an ignorant little shit.”
We stare at each other, full of mutual contempt.
“She is coming here next Tuesday for lunch, wants to meet up with you to discuss a possible business link up. I’ve shown her the samples that you left and she is impressed. You’re incredibly lucky that I agreed. However, I am aware that you owe my daughter money, so it’s in my best interests to help you, however much I loathe you. So next Tuesday at mid-day. Do not be late.”
She turns and walks off, stopping at the doorway to address me once more.
“Oh and Robert, forget about Evie, she is off limits. Not up for discussion I’m afraid.”
As she disappears I tell myself we’ll see about that.
*
Tuesday eventually comes around, it’s been an edgy few days spent trying to drum up new business without much reward. I can only hope that Pippa will be my salvation. I make my way to Sylvia’s house telling myself not to rise to her bait today. I’m going to have to be on my best behaviour.
Chambers shows me in to the reception room and tells me to take a seat. I feel a little nervous as I wait, needing this to go to plan. I need some positive news as business is still poor. After what seems like a lifetime Chambers beckons me to follow him, and leads me ponderously into the cavernous lounge. I am surprised to find it is unoccupied, I was expecting to see Sylvia looking down her nose at me. Chambers tells me to take a seat and he will inform Madam that I have arrived. I take in his features, the usually unflappable servant seems ruffled and ill at ease for some reason. He hurries away leaving me in solitude. I hear his footsteps on the creaking stairway, maybe Sylvia had one too many Gin’s last night and is taking a nap.
Five minutes pass and I’m still sat alone, this only adds to my nerves. Perhaps this is some ploy by Sylvia, nothing would give her greater pleasure than to make me suffer.
Finally I hear two sets of descending footsteps and then Sylvia’s booming voice telling Chambers that he wouldn’t be needed for the rest of the day. Her entrance isn’t full of it’s usual bombast, in fact she too looks flustered, and most unusually her hair looks quite dishevelled, and her clothing untidy.
“I’m sorry to have kept you Robert, I was a little distracted, lost track of time completely. Why don’t you come upstairs? Pippa is already here, she’s taking a look at the samples that you left behind in greater detail.”
We make our way up the grand staircase without speaking before she shows me into a plush bedroom. The sight which greets me near enough knocks me off my feet. Pippa is naked on the giant bed, legs spread wide apart, knees bent. Her hands are clasped around the head of Evie who is also naked except for a pair of boxer shorts, which bear my logo. Neither acknowledge my entrance, both engrossed in each other. I admire Evie’s beautifully tight buttocks encased in the tight cotton. Her fingers frantically sawing in and out of Pippa’s glistening pussy. Pippa’s moans increase as Evie’s tongue swirls against her clit, lashing it back and forth.
“Fucking hell.”
Not clever, but that is the only thing that I can say. The sheer enormity of what I was trying to digest was too much for my brain. I stand just engrossed for at least two minutes as Pippa’s orgasm approaches, then rips through her body, Evie’s skilled tongue doing it’s work. I can feel my erection growing quickly, no way can I restrain it. Evie continues, her tongue and fingers reducing in intensity, bringing Pippa down slowly.
“My my, don’t your boxer shorts look divine on Evie?”
I had even forgotten Sylvia was in the room, such was my concentration on the bed. Even now she cannot crack a smile or show emotion.
“Tell me Robert, do you wear your own produce?”
Lost for words I just nod, my mouth hot and dry.
“Well, let’s see shall we?”
Without another word Sylvia undoes my belt and unbuttons my jeans, yanking them down to my thighs, revealing my shorts. My erection is now almost full stretch, making a huge bulge, straining to be kept confined. Three pairs of eyes are now fixed on me. Sylvia calmly pulls the shorts down exposing my aching cock, standing proud.
Sylvia’s slender hand caresses me, pulling back my foreskin then gently stroking me back and forth. After a minute or so my dick is pulsing and impossibly erect.
“Cindy always said that this was the best part of you.”
Her technique is good. Slow long strokes along my lengh, thumb brushing against my sensitive glans. Evie and Pippa are watching intently.
“You like Evie don’t you Robert? I saw you the other night, you couldn’t take your eyes off her. You’d like to fuck her wouldn’t you? Like to fuck her tight little pussy?”
“Fuck yes, I really want her, Sylvia.”
“She wants you too, she told me. Heaven knows why, but she does. Don’t you Evie darling?”
Evie smiles sweetly and acknowledges with a delicate nod.
“Well I will allow you, even though you are mine. You have been a good girl lately, and it must get boring trying to coax anything from Chambers. The man has gone to seed.”
“Thank you, Mistress.”
“But not before I’ve sucked his cock. I’ve wanted to do that for so long. Pippa, get my girl ready for him. Make her nice and wet.”
It’s hard not to laugh hearing Sylvia talking dirty with her clipped accent and sophisticated tone. So despite the hard faced image, she has always wanted to suck my cock, what a revelation. I don’t have much time to reflect on this nugget as Sylvia is busy stripping me off, her nails raking my skin as she tears off my shirt, her tongue briefly sucking at my nipples. She has me naked within a minute and is on her knees sucking me off with gusto, taking my length with consummate ease, coating my length with her saliva. Her left hand massages my sac and it’s all too much, her skill is immense and I can’t hold back, spilling my come deep down her throat before she pulls me out of her mouth and allows the last of my load to splatter all over her nose and cheeks. I’m breathing heavily, savouring the moment.
Syliva scoops my semen from her face and licks it off her fingers, not wasting a drop. She must like it as she squeezes the huge droplet of cum from my dick onto her waiting tongue and swallows it down.
“Mmmm, your cum tastes so much nicer than Chambers. That will be all for now, Robert. My Evie is waiting for you.”
And that was it, just as if it was a transaction, no emotional attachment whatsoever.
Pippa certainly seems to have got Evie in the mood, judging from the noise she is making. Her eyes shut tightly as she is fingered hard by the more experienced woman. Sylvia picks up the discarded boxer shorts and takes in the aroma of Evie’s scent. Her eyes flicker and I swear that she shivers ever so slightly.
“Pippa, that’s enough now. I want to see Robert fucking her. Awfully well done though, she looks like she is sopping wet.”
Pippa moves off the bed, almost forlornly. I sense that she wanted to make Evie climax. Sylvia is right though, her pussy is glistening and swollen, and looks delicious. My flaccid penis is soon making it’s way back to full erection, I want Evie so badly, and the thought of Pippa and Sylvia watching makes the whole situation so much more erotic.
“Go on then Robert, fuck her, right now. I want to see her on all fours, and I want you to fill her tight little cunt.”
I sigh inwardly, so I’m going to be fucking her as per Sylvia’s instruction then.
“Spank her ass first, she loves that. You do want that don’t you Evie sweetheart?”
“Yes Mistress. I do.”
I roughly grasp Evie and push her onto her knees before giving her time to think my outstretched hand crashes against her pert derriere. She gasps and takes a sharp inward breath. I quickly repeat my action, and then again. Her wimpers are half pain and half pleasure. A couple more blows and my hand mark is imprinted on her flesh and it gains a ruby red hue.
“Enough. Fuck her. Fuck her now.”
I decide to defy Sylvia and spank her once more, causing Evie to yelp.
“I won’t tell you again, Robert. I want you to screw her hard.”
I crudely push Evie’s knees further apart and then tease her puffy lips wide, causing her to gape a little. She has such a neat and pretty shaven pussy, truly adorable. I gently hold her hips and guide myself inside her, slowly at first as she takes my bulbous head. She gasps a little as I penetrate her.
“HARD I SAID. FUCK HER HARDER.”
Sylvia is beginning to piss me off now.
I thrust hard and bury my bone hard cock deep inside Evie, making her cry out, her fingers digging into the bed sheets, a contorted look on her face, teeth gritted. I think she isn’t enjoying it, but it seems I’m mistaken.
“Fuck me, really give it to me. I’m so gagging for it. Fuck me like the slut I am.”
Sylvia pipes up, telling me to do as I’m told.
I redouble my efforts, now gripping her hips with force, pushing her hard onto my dick, then pushing her off, then back on harder still. Her juice slathered all over my length as I make the bed rock and creak with my motion. Evie is loving it, now hollering the walls down, especially now my thumb is circling her clit rapidly, clockwise, then anti clockwise. The incredible slap of my balls against her ass adds to the ambience of our fucking.
Possibly due to Pippa’s ministrations earlier, Evie comes quickly, violently. The bed, the walls, the whole room shakes as she reaches a tumultuous orgasm. She spurs me on and I fuck her even harder as she rides out her climax. I shift position and move forward, cupping her breasts, touching her stubby nipples as I feel my come rising again. I can’t hold back, her vice like grip makes it impossible. I grunt loudly and spurt another huge load, deep inside Evie.
The feeling is like nothing else, so bloody good. I’m spent, collapsing on top of her, both of us breathing heavily. I hold her in my arms, kissing her neck and ear, before she tilts her head and gives me a breathless kiss deep on my lips, her eyes burning into mine. She deftly wipes tiny beads of sweat forming on my brow, affording me a stunning smile.
The intimacy of the moment is shattered, unsurprisingly by Sylvia.
“That’s enough thank you. No kissing. I didn’t say you could kiss did I?”
I notice that Pippa is no longer in the room, she must have gone to freshen up.
I kiss Evie’s forhead and withdraw myself from her, my semen trickling out of her as I do. I go to retrieve my clothes, my path suddenly blocked by Sylvia.
“Did you enjoy that, Robert? It certainly looked that way.
“Evie is beautiful. It was wonderful. Thank you.”
I bend to pick up my garments, Sylvie’s hand pushes against my chest, blocking me.
“Where do you think you are going, Robert? Your afternoon isn’t over yet.”
I stare at her, puzzled, nonplussed.
As if on queue Pipa reappears, naked. I say naked. Naked except for a striking black shiny strap-on. The penny drops.
“Oh no, no. Absolutely no fucking chance, Sylvia.”
“Well, how can I put this. Be fucked, or you’re fucked. Without Pippa’s contacts, well you’re screwed anyway. Pardon my crudity.”
A sinister smile plays on Sylvia’s face.
“Take it like a man. Who knows, you might like it. Chambers does. He positively loves it.”
I’m beginning to think whatever she pays Chambers, it’s not enough.
“One word, Robert, lubrication. You’ll barely feel it. I promise.”
Without another word she pushes me back onto the bed, with Evie’s help I’m manoeuvred onto all fours. I feel the cold splurge of lubey against my anus, and then Evie’s fingers gently probing me, pushing her thumb deeper inside me. This doesn’t feel too bad at all, in fact I could get to like it. Sadly it doesn’t last and her fingers are replaced by the cold ruthless rubber of the strap-on.
Once again Sylvia is directing operations.
“Give it to him, Pippa. Fuck him hard. Make him work for the business you’re giving him.”
The incredible pain as Pippa attempts to push the head of her appendage inside me brings tears to my eyes. Fuck, is this worthwhile? Is money worth the pain? Thankfully Pippa does go a little easy, sensing my reticence. She slows and nudges slowly against me, eventually I yield and the cock is inside me. I grit my teeth and come to terms with the girth, thanking my lucky stars for the lube. Evie creates a welcome diversion, reaching under and stroking my cock gently, bringing it back to life.
Now two inches inside me, Pippa decides that’s enough of the gentle touch, seemingly trying to get the whole six inches inside me in one go, it’s just not going to happen. I try and tell her to stop, but I find Sylvia’s hand covering my mouth, muting me. Pippa thrusts deeper and finds my g-spot. The pain subsides a little and is balanced by pleasure. My dick jolts, instantly hardening, aided by Evie now taking my veiny shaft into her mouth, swallowing me deep.
I’m being fucked hard now, starting to enjoy it a little. Pippa strokes my sac as she pounds me, giving me increased pleasure. The enjoyment just about outweighing the pain, and to see Sylvia now seated by the bedside, legs apart, panties pushed to one side masturbating with wild abandon just tops everything off. Her pussy is hairy and unkempt, her fingers wildly strumming her clit. Her stuffy image is kicked into touch as she orgasms violently, squirting a huge arc of liquid into the ether. I feel I’m going to wake up any second and realise this is all a dream.
The proximity of three aroused women is too much, the smell of sex fills the room. Assorted gasps and sighs meld into one huge sound and a final thrust of the rubber cock makes me explode, my length fully inside Evie’s pretty mouth. Spurt after spurt of creamy cum spills out out me. It’s too much volume and my cream trickles out and onto her lips, she withdraws me at the same time Pippa leaves my anus empty. Once again I crash onto the bed, totally expended this time.
I must have crashed out for a few minutes. I’m revived by a glass of water...thrown into my face courtesy of Sylvia. The emotion and sexuality she showed earlier, definitely was a one-off.
“Time for you to go. You have served your purpose here. Goodbye Robert.”
*
Four weeks later and I’m snowed under. Orders are flying in from all corners of the world. I’m selling underwear quicker than I can make it. New premises and more staff are in the pipeline. Every time I see a pair of my trademark boxers, in a white, small size I can’t stop myself thinking about Evie and our amazing time together. I have contacted her and look forward to meeting up, if she can escape the clutches of Sylvia.
A knock on my office door, I’m not expecting anyone. I open up and find Cindy looking at me. I usher her inside and take the envelope from her. An invoice for her services.
“I trust my mother was able to help you out then?”
“Oh you know, she has her uses.”
Cindy moves forward, a wry smile on her face.
“So she tells me. Evie and Pippa too. Sounds like you all had a fabulous time.”
I’m shocked. I didn’t think Sylvia would divulge such information.
She moves closer, her face inches from mine. I feel her hand unzipping my flies, working it’s way inside my shorts. She gently coaxes my dick to life. Looking me square in the face, her piercing eyes glinting.
“So, how is your ass? Can you sit down without a rubber ring yet?”
I smile and tell her I’ll survive.
“Oh, and by the way, Cindy. There’s something I need to ask you.”
“Go ahead. What do you want to know? Only make it quick. I’m expecting sex. You owe me, remember?”
“Please tell me Chambers didn’t have you as well? That man seems to be very active for his age.”
Cindy’s gaze leave mine. Her smile fades and her eyes lose their lustre.
The silence is deafening.
Elouise
- 21.10.2022
- 5
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- Category:
- Group Sex
