Chapter 1

Caution: This Cheating Sex Story contains strong sexual content, including Ma/Fa, Consensual, Cheating, Anal Sex, Workplace, .

Desc: Cheating Sex Story: Chapter 1 - I'm the son of a very rich man and I'm determined to make it on my own!

I was just leaving work at 2pm when I noticed my boss's wife in the car park looking very distressed and upset, at first I was wary of approaching her because the other workers had told me she was a bit of a dragon, but she looked almost ready to cry so I just said,

"Excuse me ma'am is there anything I can do?"

She looked as if she was about to chew me out, but she shook her head and said softly,

"No but thank you for offering, I'm supposed to be flying over to Ireland on the 15:50 flight from the airport, but there's no way I'll make it now"

"Do you have any luggage?"

"No, I was just going for a meeting and coming back tonight, why?"

"Excuse me for just a minute" I said and fished my phone out of my pocket"

"All is not lost"

My older brother answered on the first ring, "Yo kid, what's up?"

"Did you say you were taking the 15:50 over to Belfast?"

"Yeah why?"

"I have an important passenger with me, if I leave now, can you wait, I'm talking just a few minutes?"

"Shit you know all about timing slots"

"I'm leaving now, We'll be there in 25 or 30 minutes"

"OK you fucking pain, give me her name and I'll have a word, hey kid?"


"Hurry up"

She looked at me with astonishment in her big blue eyes, but dived into the front passenger seat of my car in a flurry of long legs and tousled blonde hair,

"I don't understand this, I thought you worked for my husband"

"I do"

"You're holding an aircraft up with one phone call?"

"Yes ma'am, my brother's the pilot"

"Yes but, the airport check in and all that, they'll never get me on"

"My dad's company owns the airport ma'am"

"Bollocks, your dad owns the airport and your working for us?"

"That's right"

"And you drive this thing?"

This thing was an Aston Martin DB5, A vintage James Bond car, well maintained by my dad's mechanics and capable of well over a hundred miles an hour as well as being worth an awful lot of money.

"Yes, nice isn't it?"

"There aren't any seat belts"

"No, it's a 1965 model, they were never fitted nor required"

By then we were doing over a hundred on the A50 heading out towards the airport, if we met any law, I was finished, but luck was with me and twenty minutes later, we pulled up outside the terminal.

"I don't know what to say" she said still astonished at the events of the previous few minutes,

"Just run towards that guy over there" and I pointed to another brother frantically beckoning her,

"Thank you, I'll see you in the morning"

"Hurry up" I yelled back as I admired her trim little figure running away from me!

Everything I'd told her was true, my dad did own the airport, my brother was the pilot and another brother was the airport manager, dad had offered me a position as airport facilities manager, but I'd turned him down to work for the largest transport company in the Midlands as a trainee shipping clerk, I wanted my own business and I wanted to know everything there was to know about the transport business first, all my mates told me I was mad, I probably was/am, but at nearly nineteen I'd already learnt a lot about costing and how to minimise running empty, etc, etc, etc.

I was tootling back towards home when my mobile rang showing my older brother's name,

"Hello mate" I smiled,

"The lady says thank you" was all he said and I smiled again.

The following morning, I was working on some figures when the office manager came to my desk and said,

"The gaffer wants to see you"

"OK" I thought he meant the depot manager, but as I stood up, he looked at me and frowned,

"Not the manager, the boss, the man who owns the fucking place, comb your hair, smarten yourself up a bit for fuck's sake"

"Hey" I laughed, "This is how I came to work, if I'm smart enough to work like this, I'm smart enough to see the gaffer"

He sighed deeply and beckoned for me to follow him, he knocked on a door and waited until a voice boomed out, "Come in"

We entered and I saw my boss behind his desk, he looked up and told the office manager he could leave,

"Is this him?" he said and I realised his wife was sitting against the far wall,

"Yes" she said and then "Hi" to me,

"My wife tells me you did her a big favour yesterday"

"I was pleased to help"

"She also tells me you're not what you seem to be"

"I'm a trainee shipping clerk sir, nothing else"

"As well as being a very rich trainee shipping clerk"

I said nothing,

"Why are you here?"

"You sent for me sir" and I heard his wife hiding a laugh,

"Don't be smart lad, you know what I mean, your dad owns four airports, a few dozen hotels, God knows what else and you're here in my firm earning peanuts, why?"

"I want to learn the business sir, the transport business, I want my own company one day"

"Why not ask daddy to buy you one?"

I didn't care for the emphasis he put on the word "daddy"

"And do what? Run it into the ground because I don't know anything about running a transport company?, no thanks, I came here to learn and that's what I'm doing, or at least I thought I was"

"It's a hard game son"


"One mistake can break you"

"Have I made one? It seems as though I might have"

"No, no not at all, first of all I need to say how very grateful I am to you for helping my wife"

"Like I said sir, I was pleased to help, the lady looked a bit distraught"

"Yes my driver crashed on the way to pick her up and the fucking idiot didn't have his mobile phone with him"

I said nothing and waited for him to continue,

"Your car"

I still waited,

"You obviously didn't buy it on the wages I pay you"

"No sir" then I felt cheeky and added, "I couldn't buy a push bike on what you pay me sir"

His wife didn't bother hiding her laughter that time, even the boss managed a grin,

"Well my driver was injured so I'd like you to act as my wife's chauffeur until he's well enough to resume his duties"

"When will that be sir?"

"About a month I should think, why?"

"I came here to learn about transport sir, I won't learn much as a chauffeur"

"You'll learn promptness and civility, you'll learn about driving through the night when necessary and you'll gain experience, but above all, you'll earn my gratitude, oh and you'll earn a good pay rise, night out money, overtime and all that"

"Will I be coming back to my job afterwards?"


"No?" I couldn't believe it!

"No, when the job ends I want you to work alongside me, that's when you'll learn all about the business and I'll also get you through your HGV 1"

"All right sir, I'll do it"

"Good man, good man"

His wife was smiling too and mouthed a thank you at me,

"Right, I'm having a new Mercedes delivered very soon, so I'd like you to go home and change, have you a dark suit?"

"Several sir" I smiled,

"Yes well, get a taxi back here, charge it to the company and when you get back we'll go over your duties"

"Very good sir"

"Oh by the way, you'll be driving to Glasgow tonight"


"Yes Glasgow, it's a little place on the Clyde you know"

"Yes sir, I believe we have a hotel or two there"

"Right then, off you go"

I was back within two hours to find Mrs. Hawthorn waiting for me beside a gleaming new Mercedes,

"Right Thomas" she said pleasantly, "Glasgow please, the Central hotel, I believe it's one of your fathers"

"Yes ma'am"

"It's Mary, Thomas, at least when we're alone"

"Very good ma'am er Mary, any particular route?"

"I'll leave that up to you, well you and the satnav"

I swung out of the car park onto the busy A50 and aimed for the M6 north which took me just half an hour, then it was just over three hours before I hit the M74 north of Carlisle, it took me a further hour and a half to hit the outskirts of Glasgow and another hour to negotiate the traffic to the hotel,

Two rooms had been booked for us, but dad had asked me to look in on the manager just to pay my respects, I asked the male receptionist where I would find him and he looked down his nose at me,

"Why would you be wanting the manager?" he asked snootily, but I couldn't be bothered with the idiot so I took out my phone and punched in the number that dad had given me,

"Hello Frank, it's Thomas, Thomas Green"

"Thomas, where are you?"

"I'm in reception"

"Ah there you are" a voice behind me said cheerfully and we shook hands warmly,

"What's all this about you playing at being a chauffeur?"

"All part of the learning curve Frank" I smiled, "But the lady I've brought up is the wife of an important customer who's business I think we've got, so dad wants even more than your best for her"

"Of course, of course, what room number is she in?"

"Who sir?" asked the receptionist, Frank took a deep breath and excused himself to take the snooty idiot to one side, when he returned it was with a pretty young woman who glanced at the register and announced she was in room 201,

"Upgrade her please to the penthouse suite and if at any time in the future she books, please give it to her again, normal room rates will apply"

"Very good sir"

"Your dad will probably chew me out for that but if it gets us her company's business it'll be well worth it"

"Just then Mary appeared and I introduced them both, Frank told her she'd been upgraded and she smiled her thanks to us both, before asking about dinner,

"Whenever you like madam" he replied, "In your suite or the dining room?"

"Oh the suite I think, will you join me Thomas?"

"Thank you, yes I'd be pleased to"

"Dress casually then please, I can't be bothered to dress up"

The receptionist took her up to show her the suite leaving me to talk to Frank about how the hotel was doing in the recession, but he said it was doing well, "Mind you, any new business is always welcome" he said.

"Can we speak privately Frank?" I asked and he took me into his office,

"Drink?" he asked and I nodded my agreement as I'd finished driving for the day,

"Your eyes only Frank" I said and handed him a letter from dad,

He read it and looked up at me with a smile,

"Do you know what's in this?"

"Yes, he wants your answer as soon as you like"

He reached out for his phone and asked the desk to put him through to head office, then switched on the loudspeaker,

"Clive Green please"

"Green" my dad said in his usual brusque manner,

"Frank Thornton here Clive"

"Frank, how are you? Good to hear from you, did you get my message?"

"I did indeed, the messenger is sitting in front of me now" he winked at me,


"Well yes, of course yes, but a new hotel?"

"Yes, it will be ready to open in two years time, central Paris, a top job Frank but I only want top people running it"

"I don't know what to say"

"Say nothing, that's always best, I'll be in touch" and he hung up!

He looked over at me and smiled when he saw me laughing,

"He doesn't waste words does he?"

"Not many Frank no"

"I'm stunned Thomas"

"Well you shouldn't be, he thinks you're the right man for the job and if my opinion's anything to go by, I think he's right"

We chatted a bit longer then I left him and went up to my room where I stripped naked and got into the shower before pouring myself out another drink,

Mary called then on the house phone and asked me to join her for a drink before dinner, she wanted to go over the following days schedule with me.

The penthouse had it's own private lift with a tiny blonde woman to open the doors for me when it arrived,

"Thank you" I said and then did a double take, the tiny blonde woman was Mary!

She giggled at my mistake and at that moment I thought she looked beautiful, gone was the carefully styled hair, the smart business suit and the high heels, instead she wore an old denim mini skirt that showed off her lovely tanned legs with a little white vest top which didn't seem to hide a bra and flip flops,

"My casual gear" she laughed, "It feels great just to dress down occasionally"

"Well if I may say so Mary, you look sensational"

"Thank you Thomas" she laughed, "This is how I dress when I'm at home, but my husband says I look scruffy"

"With all due respect Mary, he's wrong, you're gorgeous"

"Gorgeous, wow, you know how to make a girl feel good"

"I'm only speaking the truth as I see it"

"OK, let's have a drink to the truth" she smiled, "As you see it and we can look through the menu"

I found it very difficult to concentrate on the menu with her beautiful face only inches from mine, nor did her perfume help and I found myself becoming aroused at her proximity,

"I think I'd like a steak Thomas" she said, "What about you?"

"Yes, a steak will be fine" I said and pulled away from her before I did something that I'd almost certainly regret,

She looked surprised and a little hurt,

"What's wrong Thomas?"

"Nothing" I stammered, but my face gave me away,

"You didn't like me being that close to you did you?"

"No, I mean yes I liked it fine, that's the trouble, you were, er, you know, you were having an effect on me"

She looked down at my groin and then back up at me and smiled,

"Shall I tell you how much younger than my husband I am?"

I nodded,

"Well, he's fifty four and I'm twenty nine, a difference of twenty five years Thomas"

"That's a lot" I agreed and sipped at my drink,

"Yes, you see if I was a stay at home wife, I would probably have a lover, you know a quick shag every afternoon before getting hubbies dinner ready, but I'm not a stay at home wife Thomas, I'm a wife who goes out getting new business and servicing the contracts we already have, I'm a very busy woman Thomas, so fucking busy that I've almost forgotten what it's like to be loved, properly loved, to feel a man's arms around me, to feel his lips on mine, just to feel wanted Thomas"

Her voice broke then and she sobbed, "Just to feel loved"

"I was afraid you'd scream if I did what I nearly did then when we were close" I said softly,

She looked at me through tear filled eyes,

"I wanted to do this" and with one step I took her into my arms and kissed her,

it was a hard kiss, almost brutal, but she melted and made a funny little noise as she moved against me,

Her hands scrabbled at my back lifting my tee shirt, then I felt her nails on me, I slid my own hands up underneath the back of her vest top and discovered I'd been right about the bra, there wasn't one, she moaned into my mouth as I found her breasts and gently squeezed a nipple,

"Yes Thomas, yes" still with our mouths locked together, I lifted her skirt and felt her sexy little bottom clad only in what felt like a very small and very tight thong, we fell on to the couch together her scrabbling at the belt of my jeans, she was like an animal, a wild animal, she pulled my jeans down and I kicked them off, then it was my turn to moan as I felt her full, red lips slide over my rigid cock,

"Oh God yes, oh fuck Mary that feels good"

"It's meant to Thomas" she grinned and went back to her work, somehow I managed to get rid of her skirt and vest top, her thong ripped as I tore it off and we were naked, I had to force her head away from my groin to lift her up where I wanted her and I felt her hand on me, guiding me to where we both wanted me to be,

She let out a long, slow moan of desire as she sank down on my cock, the soft warmth of her pussy felt like nothing I'd ever felt before,

"On top of me Thomas" she hissed, "I want to feel your weight on me"

We rolled over and her legs went round my hips,

"Slowly Thomas" she breathed, "Slow and deep, yes that's it, that's beautiful, oh fuck yes, I can feel every fucking inch of you inside me, fucking me, hold me tightly Thomas and shag me slowly, ooh fuck yes, this is so fucking good, so very fucking good"

I began moving faster, faster and deeper, I slid both hands under her bottom and cupped her cheeks, she squealed and bit my neck as my two forefingers caressed her little rear hole,

"Dirty man" she hissed, "Push a finger in"

I did and it made her squeal, I pushed deeper at the same time as I thrust into her savagely, her squeal became a cry, almost a howl as she climaxed, I felt her nails tearing my back,

"I'm coming Mary" I hissed as I felt the familiar tingling starting in my legs,

"Yes, yes, oh fucking hell yes, fill me Thomas, give me all you've got, shoot it all into my hot little cunt"

"Yes, yes I'm coming" I hissed again as I erupted and held myself rigid, her big blue eyes were wide open, her mouth formed an O and she made an arch with her back until gradually our passion subsided and we collapsed gasping for breath.

"Oh my God Thomas, you're a stallion"

"And you're an amazingly sexy lady"

"Let's order dinner"

"Good idea" I said and passed her the house phone, she did well to ignore me while she ordered, because I kissed each breast in turn, by the time she was ordering the sweet, I was kissing her stomach and I was just kissing my way lower when she replaced the phone and laughed, "Shower" before running into the bathroom,

Showering with her was an erotic experience, but we needed to be out and waiting when they served our meal so we curtailed our activities and made ourselves respectable and when the knock at the door came we were sitting at the table planning tomorrows schedule.

Frank himself oversaw the serving of it making me even more certain that dad had made the right choice for his new hotel.

We took our drinks out onto the balcony after we'd eaten and watched Glasgow at night far below us,

"I love this place you know" she said wistfully, "Did you know that at one time it was the second most violent city in the UK, second only to Belfast?"

"The government should have sent you up here then" I said behind her and slipped my arms around her waist, "They would have all fallen in love with you and they'd have been too smitten to fight"

She giggled and wiggled her bottom against me as I kissed her neck,

"You say the nicest things Thomas"

"Only to the nicest person I know"

Turning round she placed her empty glass on the table and snaked her arms round my neck,

"Will you stay with me tonight?"

"I was hoping you'd ask me"

Her phone rang then and she mouthed that it was her husband, she sat on the couch and answered it whilst gesturing to me for another drink,

I poured out two brandies and put one beside her, her eyes widened as I pulled off one of her shoes and kissed her toes, they got wider when I pulled her other shoe off and kissed those toes, wider still when I slid both hands up over her thighs taking her skirt with them until the sexy white vee of her panties came into view,

"Yes dear" she was saying, "Don't worry, I know exactly what I'm doing"

I didn't know about that, but I knew what she was doing at that moment, she hooked a finger under her panties and pulled the material to one side, she never missed a word as I bent my head and touched my lips to her gorgeous little slit, she placed a hand over her phone and moaned softly as I ran my tongue slowly up in between her hairless cunt lips, I lifted up then to tug her panties right off, she spread her legs wide open in invitation, I accepted the invitation and lifted both her legs up over my shoulders,

Her pussy tasted just as beautiful as it's aroma suggested, Mary laid a hand on my head as she finished the call, "Thomas?"

I looked up at her and saw sheer, naked lust in her eyes,

"Is it, you know, is it all right?"

I took a long, slow lick along the whole length of her slit worming my tongue into her wetness,

"It's more than all right Mary, it's the most beautiful thing I've ever tasted, if I die now, I'll die happy"

"He says it's dirty"

By way of an answer, I pushed my face into her groin and pulled on her buttocks, her wetness engulfed me and I loved it, the juices inside her tasted like nectar and they flowed plentifully over my tongue,

"Ooh yes Thomas" she crooned and moved her hips up against my face, she squealed when I licked her clitoris before flicking it rapidly with my tongue and she sucked in her breath when I ran my tongue gently over her sexy little rosebud,

"Oh fuck Thomas" she moaned, "Let's go to bed, I want to be naked again with you, I want to do things to you"

"Things?" I grinned as I straightened up"

"Rude things" she said and blushed, "Very rude things"

We undressed each other slowly, slowly and sexily, I kissed every little piece of her body as I uncovered it until finally we were both naked, my cock was standing straight up almost touching my naval, she whimpered as I kissed her and whispered that she wanted me to touch her bottom again, '

"You know Thomas, with your mouth, I was nearly coming" she added shyly,

But I suspected that she wanted something else,

"Would you like me to, you know, fuck you there?" I ran a hand down over her lovely bottom and slid a finger in between her buttocks,

"I'd fucking love it" she whispered in my ear as she stroked my cock, "I want to feel every fucking inch of this up my bum"

Kissing hungrily we lay back on the bed with Mary still gripping my cock, eagerly she positioned it up against her rear hole and fixed her eyes on mine,

"Do it Thomas" she hissed, "Put it in me"

I pushed forward gently at first and she screwed her face up, I stopped pushing but she was insistent,

"Keep pushing Thomas"

Suddenly her anal muscles relaxed and my cock slid straight in, she screamed but then gripped me in case I pulled out, I held still until a smile spread over her face,

"That feels beautiful Thomas" she sighed, "It's filling me, oh God yes I fucking love this"

I began fucking her with long, powerful strokes and felt her ankles gripping my back, she pulled my head down to hers and we kissed hungrily,

"Is it nice for you?" she asked and I laughed,

"Mary, everything about you is nice"

"Even my bum?"

"Especially your sexy little bottom"

"My pussy too?"

"I love your pussy you know I do, I'd eat it for breakfast every day if I could"

"Mmm nice thought"

"Yes, you on the table in front of me naked except for stockings"

"Do you like stockings?"

"Love 'em"

"I'll buy some, now fuck me hard"

I did, every thrust made her squeal, it was my first time for anal sex too, but I didn't tell her, I wanted her to think I was vastly experienced in all matters sexual,

I felt her long nails digging into my buttocks, she was biting my neck as she pushed herself back at me,

"Make me cum Thomas" she urged me, "Make me fucking scream"

We found a rhythm that suited us both, with every forward thrust of mine, she pushed too and clenched her buttocks at the same time making her anus even tighter than it already was, our mouths were locked together too exchanging saliva as we kissed wetly,

"Thomas" she gasped, "Oh fuck Thomas" her fingers dug into my buttocks, her head tossed from side to side and she bared her teeth in a snarl like grimace, "Thomas I'm cumming, oh fuck yes, I'm there, I'm FUCKING CUMMINNNNG" she sank her teeth into my neck and I thought she was trying to break my back with her legs, I lunged forward with a growl making her scream again as I erupted, we clung to each other still rutting, both of us still enjoying the after shock of what had been an amazing climax,

"Never Thomas" she whispered softly, "Never did I ever come that hard before, it was amazing, mind blowing even"

"You're a very special lady Mary" I said as I pulled her with me to lie on my side, incredibly my penis was still semi hard and still inside her anus,

"Leave it there Thomas" were her last words as we allowed sleep to claim us!

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Story tagged with:
Ma/Fa / Consensual / Cheating / Anal Sex / Workplace /