This was initially written as a short story for a cuckolding anthology but I’m thinking of turning this into something a little larger. It’s not intended to be anything even remotely serious, because let’s face it – Sex should be fun.
Any feedback greatly appreciated.
Chapter One – In His Father’s Footsteps.
Tom unhitched his bike from the rack on the back of his Volvo and scanned the assembled crowd for his intended target. There! He would recognise that face anywhere. Ben was the spitting image of his father Lee. Tom and Lee had been the best of friends before Lee’s untimely departure. They had shared almost everything; houses, cars, girlfriends and eventually wives. Now Lee was gone, right when he needed him the most.
Ben had been cycling with the Hawks Cycling club for three years now and knew all of the regulars, as well as some of the “fair weather” riders. Since starting university however, his time with the club had been relegated to the holidays plus the odd weekend when he could get home. He recognised Tom almost immediately from his childhood.
“Hey Tom, over here!” Ben thrust out his right hand. “You may not remember me. We’ve not seen each other for some time but you look the same as ever, what’s it been? Fifteen years?”
“Benny? I thought that was you. I think you were what, seven or eight the last time I saw you? You look so much like your father. But you’ve got your mother’s eyes. How are you my boy? It’s so nice to see you. How’s Bronwen? Sorry, how’s mum?”
Ben and Tom talked about old times, about Ben’s university studies and what he wanted to do once he finished his degree. Ben forsook his usual workout to keep pace for Tom, noting that the older man was struggling.
“Tom, are you alright? You look wiped out and we’ve only done a few miles.”
“I’m just really out of shape. My doctor says that I need to get some exercise so I got the old bike out of the garage. I used to cycle with your dad for hours but I forgot how bloody steep these hills are.”
“I don’t really remember that much about him. I can’t even remember his voice.”
Tom answered, “It’s quite understandable Benny. Tell you what. Why don’t you come to our place and have dinner with us tonight? We can talk about old times, about mum and dad. I might even have some old photographs around somewhere.”
Ben was a little edgy. He hadn’t seen Tom or Rebecca for such a long time. Tom sensed Ben’s reluctance and decided to change tack. He didn’t want to lose his opportunity as he had been planning this for some time.
“Better still, let’s go out on the town, my treat. Rebecca will be jazzed to see you again. You know she had a real thing for your dad when we were younger, and you look so much like him. Meet us at Guido’s at eight p.m. tomorrow night. You do know where that is right?”
“Yeah alright then, eight p.m. tomorrow it is. Race you back to the pub.” Ben replied.
Ben was late. Ten minutes late. He was never late. He hated making people wait. He was better than this.
When he entered Guido’s, Tom and Rebecca were already there. Tom was propping up the small bar ordering another drink. Man, he looked old. Was it the several drinks that he had already had or was it something else? Ben tried to do the maths in his head. How old was Tom? He can’t be more than forty-five. Fifty at most and Ben couldn’t help thinking how tired Tom was looking. Their earlier workout wasn’t that strenuous, was it?
Tom greeted Ben with a handshake and a fatherly arm around his shoulder. At 6”4’ Ben seemed to tower over the older man. Sure, Ben was a big man and he worked out a little. He rode at least 50 miles a week and played a little tennis but he didn’t consider himself ‘buff’, just healthy.
“What’s your poison Ben? What’ll you have?” Tom gestured to the barman waiting to take his order.
“Just a bottle of Bud please Tom.” Ben wasn’t much of a drinker, but since someone else was paying, why the hell not.
Tom led Ben over to their table, to Rebecca. She was more beautiful than he remembered. Ben had always been a sucker for redheads, especially ones with long hair and Rebecca was his ideal of a woman. Tall, svelte, auburn haired with alabaster skin, perfect teeth and pouting lips. Tom was one lucky guy. How he landed such a catch was a mystery.
Ben’s reaction to seeing Rebecca again was obvious. His smile broadened, his back stiffened and his cock twitched like never before. As Ben poured on that infamous O’Donilly charm that had served both Ben and his father before him so well, Rebecca was now certain that Tom had made the right choice. ‘Tonight’ she thought to herself, ‘tonight, I’m taking that hunk to my bed and I’m going to devour him like the man-candy he is.’
Ever the gentleman Ben took Rebecca’s hand, slowly bringing it to his lips and gently kissing her delicate fingers. Fingers that he desperately wanted exploring his body.
“Rebecca, you remember Ben?”
“Where are my manners? Ben, here have my seat.” Tom pulled out the chair opposite Rebecca and then took his place to Ben’s left. The small circular table was only really meant for two but Tom had booked late and the maître d had squeezed them in last minute. For a small fee of course.
Tom ordered a bottle of champagne from a passing waiter.
“Why the champagne?” Ben looked at Tom and then Rebecca quizzically.
“It’s my birthday.” Replied Rebecca. “Twenty-nine again.” She smiled at Ben as she slipped off her shoe and gently ran a stocking clad foot up Ben’s left leg. Ben could feel his cock unfurling, a tinge of embarrassment flushing his cheeks. Right in front of Tom too. This woman is incorrigible and hot as fuck. Ben’s thoughts betrayed him.
Her mind made up, Rebecca stopped, collected her purse and excused herself from the table.
“Excuse me, I need to go and powder my nose.” She leant in to whisper in Tom’s ear, “Hurry up and ask him.” It was not so much a whisper, more of a quiet order. She continued much quieter now,
“Do you think he bought your hurt puppy act? I really want this.”
In answer, Tom whispered back, “I know so. Just a little more and I think he’ll be ready.”
Without another word, but a playful knowing smile and a sly wink at Ben, she left the room.
Tom’s voice broke Ben’s stare, snapping him back into the room.
“Benny, it’s good to see you again. I just can’t get over how much like Lee you look. Does Bronwen ever talk about us?”
“Mum doesn’t really discuss Dad much. Or her life before. I know that the four of you were pretty much inseparable. But no. I haven’t heard her mention either of you in a long long time.”
“Tom, I don’t’ want to appear rude but are you going to tell me what the fuck is really going on? You didn’t ask me to join you to talk over old times did you? What does Rebecca want you to ask me?”
“Ben, Lee and I, we used to be real close. Closer than brothers. We shared everything – and I mean everything.” Realisation struck Ben like a hammer to the face. How did he not see this coming?
“Lee’s gone Ben. I need you to take his place. To take my place.”
“Take his place. What do you mean take his place?” Even when Ben said it he knew exactly what was being asked of him. It was a dream come true. Here was this stunning woman who obviously wanted him and her husband was handing her to him on a silver platter.
“Ben, don’t look so shocked. Your dad and I… well, we used to swap partners. Lately, I’ve not been up to the task and Rebecca, she needs you.”
“Tom, you’re shitting me! There’s more to this than you’re telling me; your sick aren’t you, I thought you looked off colour.”
Tom avoided Ben’s gaze, a far-off look in his eyes.
“It’s the chemo. I just don’t have it in me at the moment. I love my wife Benny, I want to see her happy. In the past I would have asked Lee but, well he’s not here and you are. I’m hoping that you’re a chip off the old block. I knew that the moment Rebecca saw you that she would be hot for you and I can see it in your eyes; you want her too don’t you?”
Ben wasn’t a teenager anymore but he was still horny all the time. The thought of taking Rebecca to nirvana was seriously turning him on.
Tom turned his head towards his approaching wife, as did most of the male clientele. As she came closer, Rebecca and Tom exchanged a glance that told her all she needed to know.
“Screw dinner Tom. Let’s go. I want to fuck.”
“Can I have the bill please?” Tom waved the maître d over. “I’ll catch you two love birds up. Rebecca do you have your car keys?” Ignoring Tom, Rebecca took the bottle of champagne in one hand and Ben’s arm in the other not stopping as she walked them to the car. Her quickened pace betraying her eagerness for what was to come.
When Tom caught up with them they were already on the back seat necking like teenagers and drinking straight from the bottle sharing the bubbles between their open mouths. He just sighed and opened the driver’s door, silently dropping into the seat, slipping the key into the ignition as Ben slipped his fingers into Rebecca’s panties, totally oblivious to Tom’s arrival.
Tom avoided looking in the rear-view mirror as he drove to the hotel chosen for the night’s activities; there would be much better things to see once they were somewhere more private; the room had already been prepared, and everything had fallen into place exactly as planned. “We’re here.” Tom turned towards his wife and her lover. He smiled when he saw Rebecca had wasted no time. She had slipped off her panties and was using them to stroke Ben’s shaft as she fisted his cock, her lips engulfing his tip. Ben’s head was thrown back, enjoying the sheer pleasure she bestowed.
“Rebecca gives amazing head doesn’t she.” Tom said, snapping them back to reality. “Let’s take this up to our room.” Tom flicked his head in the direction of the hotel.
Tom led the way. Like a good cuck, he just stood there and pressed the lift call button as his wife and her admirer locked lips in full view of the lobby, his wife and this man young enough to be her son. Tom could feel the stares of disbelief from the night porter and the other guests waiting to check in. He allowed himself a slight smile, knowing what was to come. Their fantasy was finally going to happen.
As they exited the lift Rebecca almost ran through the door to their room, pulling Ben by the hand and into the bedroom, leaving it wide open for all to see as she pulled at Ben’s shirt, popping off several of the buttons. Tom casually followed them in, taking his time in closing the door before he sauntered over to the armchair positioned at the end of the bed. He carefully disrobed before taking his seat. Closing one of the handcuffs Rebecca had so thoughtfully placed at each wrist.
“A little help here, I can’t reach to do both.”
Ben stopped for what seemed an eternity to him to secure Tom’s other wrist. There was no going back now.
Rebecca sank to her knees and once again undid Ben’s fly. In contrast to her earlier efforts, she deliberately undid his belt as slowly as she could, gently lowering his trousers and then his underwear to the floor, teasing him now after being so needful in the car. She wanted this to last. She wanted him to last. With a glance at Tom she smiled and took Ben’s cock in her hand, bringing it to her waiting mouth once more, sucking him in, marking him as hers for the night with her lipstick.
“Look at how hard he is Tom. Bet you wish you still got this hard.” Rebecca taunted before she took Ben’s cock back into her mouth.
“You’re going to have to stop that or I’ll come too soon.” Moaned Ben, reluctantly pulling her off his cock and back up into his arms. He savoured the scent of her perfume before tugging the straps of her dress from her shoulders, dropping it to the floor in one swift movement.
Rebecca stood before them in just her hold-ups and bra, her panties carelessly discarded on the back seat of the car. Again Ben pulled her to him, burying his face between her breasts, nuzzling each breast in turn as he felt his way to the clasp behind, desperate to release his prize. The clasp now free Rebecca allowed the bra to fall to the floor to be with her dress. Ben grabbed at her thighs forcing her to jump in to his powerful arms. Her legs wrapped around his waist as he slowly lowered her to his waiting shaft. Already so very wet with anticipation, Rebecca offered little resistance as Ben entered her, fulfilling the needs of all three of them.
Ben lowered Rebecca onto the bed slipping his cock from her perfectly trimmed pussy, rearranging her so that Tom could get a direct line of sight. Ben dropped his head to the apex of her slit and started making broad strokes with his flattened tongue, lapping at her juices, flicking her sensitive bud and then placing his mouth over her clit, sucking it in hard; only to repeat it again and again until Rebecca’s breathing started to quicken as she started to groan loudly.
“Oh my god, just don’t fucking stop doing what you’re doing. Fuck that feels good. There, just there.”
Rebecca bucked her hips in rhythm with Ben’s tongue strokes. She grabbed at the back of his head, pulling him closer, mashing his face into her cunt, riding his face to an orgasm that made her see stars.
“Ooh baby. Fuck me. I need it. Fuck me.” She moaned as the pleasure soared through her; Ben could hear her moans and muted screams despite the pressure of her thighs to his ears. He introduced a finger into her, first one, then two and then three fingers, each one working in unison, stroking her G-spot, bringing her already intense orgasm to new heights. He could feel her Kegel muscles clenching around his fingers and he knew that she was close again. He carried on, relentlessly stroking and squeezing with his fingers all the while sucking and flicking her clit.
Rebecca suddenly lifted her head and rose up on to her arms.
“Oh god, here it comes. Here it comes baby!” the next wave of pleasure hit her hard as she gushed, covering Ben’s face. Her fulfilled fantasy making her orgasm all the sweeter.
Tom was in tortuous rapture. He desperately wanted to touch his cock. The sight of his precious Rebecca coming so hard was almost unbearable but try as he might his hands were held steadfast to the chair. Rebecca looked up at him, a mischievous smile on her lips.
“Look at him Ben. Look at my husband. See what we’re doing to him. That’s the first erection he’s had in months and I’m going to make him beg for release before the night is out. Come up here and fuck me. Fuck me hard. Show him what I’ve been missing.”
Ben hauled himself up the bed, teasing Rebecca with little nips and nibbles, stopping to pay homage to her dark nipples, sucking on them one by one.
“I love your wife’s tits Tom. Sooo delicious. The perfect handful.”
Ben carried on up, kissing Rebecca’s collar bone, around her neck and up to her right ear, gently whispering
“Let’s give him a good show.”
Rebecca raised her still stockinged legs, resting them on Ben’s shoulders, opening herself fully to him. Without hesitation, Ben plunged his fully engorged cock into her making her slide further up the bed with the force of each penetration.
“OOOH YES! OH MY GOD. Don’t you dare stop!” howled Rebecca, pushing back against him as he slammed into her again and again.
Her hazel eyes rolled back as she began to quiver, her body shuddering as she scaled the heights of orgasmic pleasure.
Ben pressed his mouth against hers, pushing his tongue into her mouth, their tongues dancing and weaving together, making her taste herself on his lips. For long moments she quivered and shook, her body responding perfectly to this tireless, virile young man who’d loved her so well, and pleased her so perfectly. When she finally opened her eyes, her gaze fell on her husband, still cuffed to the chair, his expression that of mingled lust, love and agony at the scene just played out before him.
“I think Tom has had enough Ben.” murmured Rebecca.
Ben looked over at Tom and took pity on him. Spying the key on the nightstand, he rolled off and made his way over in what he hoped was his cockiest strut releasing one of the handcuffs, dropping the key into Tom’s lap allowing him to free his other hand.
“Don’t worry Tom, I’m not done with her yet.”
Ben re-joined Rebecca on the bed this time lying on his back. Rebecca smiled slowly, a naughty, devilish smile.
“Let’s give him the best view in the house. I want him watching your cock splitting me in two.”
Rebecca got up on all fours, straddling Ben’s legs, and facing Tom. Her back to Ben, she slowly sank onto his cock once more.
“Can you see what he’s doing to me Tom? You can stroke it now. You can cum now baby,” she taunted, rising and falling as she worked herself off on Ben’s cock.
Rebecca brought herself upright, slowly rocking back and forth. Tom could see everything. He could see Ben’s rigid cock effortlessly gliding in and out of his wife’s labia. Faster and faster she rocked, working herself up into a frenzy. When she came again it was though an intense bright white light burned through her, driving away all thought and reason. Ben sensed Rebecca’s orgasm, sitting up to catch her fall as she slumped back against him, while her rhythmic tightening brought him to his own release, his world momentarily disappearing in a misty haze as his pulsating cock spat stream after stream of thick sperm deep inside the beautiful older woman.
Tom’s hand was a blur for a few seconds more before he stood and deposited his own tribute onto Rebecca’s breasts as she was momentarily blacked-out.
Rebecca regained consciousness a few seconds later to see Tom’s beaming smile.
“Did you enjoy that darling?” Tom said as he looked down on his beautiful, sexy wife.
Rebecca returned the smile, her eyes alight with love for her man.
“I certainly did. Did you manage to cum?”
“Yes I did babes. Yes I did.”
“Then you had better clean me up. Ben, can you give us a minute alone?”
“Sure… erm. I’ll go take a shower.”
Completely spent, Ben rolled over to the side of the bed, and studied Rebecca and Tom for a few seconds. A tinge of jealousy crept in as he watched Tom lovingly cleaning his wife of all the sweat and semen from her body, as well as that now dripping from her vagina, with a clean white towel. The look on their faces betrayed nothing but the love they had for each other. Ben wearily stood and walked towards the bathroom, suddenly aware that he was no longer needed or wanted.
Ben took his time showering, not sure how to face them after what they had just done but eventually had he to come back out. He shut off the water and towelled himself off, realising that all his clothes were still on the floor in the bedroom. Reluctantly he re-entered the bedroom to find Rebecca quietly dozing in Tom’s arms, a look of sheer bliss across her pretty face. Tom’s eyes slowly opened as Ben strode into his pants.
“Thanks Ben, I’ve called you a cab home. Should be here any minute.”
“Tom, this was a setup all along wasn’t it? How’d you know where I would be this morning?”
“Bronwen told me. She and Rebecca met up for lunch a few days ago and you know how women are when they get talking. Rebecca told her about her fantasy and, well… You’ve probably guessed by now that this was all just roleplay. Sorry about the subterfuge. We weren’t sure that you would go along with it otherwise.”
“Pimped out by my own mother. Damn.” Ben Smiled. “Tom, you cunning old bastard.”
“It was your mum’s idea and you’re over twenty one, plus, we all enjoyed it so where’s the harm.”
“Oh, I enjoyed it alright.” Ben responded.
Rebecca dreamily opened her eyes and addressed her lover.
“Goodnight Ben. Same time next week?”
Ben’s heart leapt as if all his Christmases had come together.
“Same time next week then.” Ben whispered in reply as he stepped out of the hotel room and quietly closed the door behind him, cheerfully whistling to himself as he made his way out to the lobby making a mental note to have a quiet word with his mother.