Swinging 60s Cuckold

  • cuckold
  • sissy
  • oral
  • pregnant

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Section 1


Peggy downed the last of her daiquiri and took a long drag of her Salem cigarette. She eyed her lover Norm through the haze of cigarette smoke as he sat on the couch across from her in his boxers and his tank top t-shirt, his broad tanned arms with the bulldog tattoo standing at attention on his bicep and his big cock standing at attention under his shorts.

“I wanna suck that cock” she slurred, her heavy lidded eyes showing the effects of the alcohol, “and then I want that cock buried deep in my pussy.”

She crawled across the floor to him, her black negligee showing her huge tits swaying to and fro, her wide hips moving with each thrust. She pulled his cock out and buried deep in her throat almost choking on it but accommodating all nine inches. He grew rigid in her warm mouth and he loved it there. He drained the rest of his beer as she sucked him and couldn’t help but think this was the life.

Sure Jimmy and her were his only friends after his wife had gone and died on him, they were always at his house; Peggy bringing him casseroles and dinners and Jimmy helping him drink his loss away. Jimmy couldn’t hold his liquor for shit and that one night he just plain passed out in the other room on the couch. Norm and Peggy were listening to records by Ray Price and she asked him to dance.

Her hands roamed freely over his massive shoulders and back and down to his ass. His hands reciprocated. Soon they were kissing as they made their way to the back porch where he fucked her silly. The next morning Peggy fed Jimmy Norm’s leftovers and have him a hand job and sent him off to work and he seemed to love it.

She crawled up him like a cat crawls into its master’s lap. She impaled herself on his rigid beautiful cock. She was so wet every time she fucked him, not like with Jimmy whom she referred to as her “two pumps and a squirt hubby” to her closest friends. Ah but Norm, he knew how to fuck.

She bit his neck as he pummeled himself into her, biting her tits and running his fingers through her hair. Norm picked her up with his cock still inside her and carried her to the bedroom. He threw her onto the bed she shared with Jimmy the wimp and fucked her hard. She ground her hips into him and whispered in his ear, “cum inside me!”

Later, as they lay exhausted on the bed in their post coital bliss, Peggy shared secrets with Norm. “I mean don’t get me wrong, Jimmy’s a good provider for me and the boys, but Jesus he can’t provide what I need between my legs like you can! I wish I had known that before we were married. All that good Catholic stay a virgin shit can kiss my ass!

The first time I saw that puny cock on our wedding night I almost burst out laughing. And then his pathetic attempt at making love or trying to fuck me, Christ I had to reach down and put it in for him and then when I did is when he earned his nickname, two pumps and a squirt!”

Norm laughed. “Oh don’t be so hard on the poor guy!”

“Hard is the last thing he is! I mean I feel sorry for our boys. I swear to God our oldest Mitchell is queer! He’d rather play with dolls than boys' toys and my clothes fascinate him. And my poor youngest, Steven, he was cursed with his father’s cock size. I see a lot of oral sex in that poor boy’s future and always on the giving end! Speaking of giving oral sex…” Peggy closed her mouth over the tip of Norm’s huge mushroom head and began to suck.

Jimmy came home later that night to find the boys asleep in their beds and Peggy passed out on the couch. He began to clean up the house and noticed the empty Budweiser can on the end table. He was furious and woke Peggy up.

“Who was here today? Who was drinking Budweiser?”

Peggy awoke from her slumber embracing the old adage never wake a sleeping lion or lioness in this case. She lit a Salem and blew the smoke in his face.

“Norm stopped by and I offered him a beer! Why? What’s it got to do with you?”

“Well I just don’t think it looks right for a man to be here alone with a woman when her husband isn’t home.”

“Ha! Give me a break! First of all, even when you’re here there’s not a man here, just a wimp! And second of all Norm’s a friend who lost his wife and sometimes he needs comfort.”

Jimmy threw the beer can in the trash. “Comfort? Just exactly what do you mean by comfort?”

“Comfort is what ever the hell I mean it to be. You want to hear the truth? You want me to say I sucked his cock and he fucked me? Okay, I did and he did!! And if you don’t like that mister two pumps and a squirt you can pack your bags and get out! There’s plenty of men, real men out there who would want a woman like me in a minute, so if you’re not happy with what I do then leave! Right now I’m going to bed, do the dishes and clean up this place.” With that she staggered away into the bedroom.

Jimmy stood there shaking not knowing what to say or do. He went to the kitchen, put an apron over his head, tied it around his back, rolled up his sleeves and began to do the dishes. He was angry, jealous, sad, but at the same time the thought of Peggy and Norm together aroused him. Washing the dishes the thoughts of the two of them flooded his already aroused mind.

Soon he felt his tiny cock growing in his trousers. Looking up he saw himself in the mirror; he looked like Jimmy Backus in Rebel Without A Cause, cleaning up his wife’s mess wearing an apron. A tear ran down his face as the thoughts of her and Norm flooded his mind.

He reached his hand inside his pants and began to finger his tiny penis which by now was soaked with pre-cum. He moved it back and forth between his thumb and forefinger, thoughts of Peggy and Norm swirling through his brain, three strokes and he could feel the orgasm building and before he knew it, he was shooting his load inside his pants. He looked up once again and saw his reflection, a single tear rolled down his cheek. He cleaned himself up, finished the dishes, and turned out the lights and wen to the bedroom.

Peggy was splayed across the mattress wearing her black slip, which rode up exposing her big beautiful ass. Her feet with their cute wrinkles, which he had massaged a thousand times, faced him. He changed into his baby blue pajamas, which Peggy had picked out for him and sat on the bed. He lit a cigarette and set the alarm.

He had read and heard on the news all about the swinging sixties, but he wondered if this is what they meant. The terms ‘free love’ ‘be free’ and such slogans were bandied about more of a punch line than a reason for behavior.

He drew deeply on the Lucky Strike and watched the smoke rise in a blue haze, which was where his mind was at this point. He knew when he met Peggy she was a wild filly and he knew then and knew now he could never tame her.

What then was the alternative? Leave her or put up with her behavior. The former was out of the question as he loved her too much and the latter was somehow buried in his psyche becoming more and more attractive to him. Jimmy knew he was no lothario; in fact Peggy was the first woman he had ever been with.

He was inexperienced and very excitable, and he knew after being in the service how tiny his cock was compared to other men. Unfortunately his cock size was a hand nature dealt that couldn’t be changed. He grew so excited every time he looked at her he wanted to cum immediately hence his ejaculating so soon each time they were together. He stubbed his cigarette out in the ashtray and pulled the covers over himself as Peggy awoke.

Section 2

“Mmph did you get everything done?”

“Yes dear. The dishes are all done and the house is picked up.”

She started to drift back to sleep but he brushed her raven black hair back from her eyes to keep her awake.

“Dear I’m so sorry we argued before. It’s just that I get so jealous thinking of you and other men.”

His face turned crimson with shame as the next words came.

“Honey I know I’m not much good to you in bed and I’m forever sorry for my shortcomings so to speak, but I’d like to think that I can provide other things for you, a house, a car, a nice life for the boys, and well if you need something extra in the bedroom, something like Norm can give you well I guess I’m okay with that.” He lay back feeling relieved until she spoke.

“You guess you’re okay with that?”

Throwing the covers back she stood and lit a cigarette and downed the last of the highball in the glass on the nightstand. She brushed her hair back from her face and for a moment she looked like a cross between Elizabeth Taylor, Jane Russell and Bonnie Logan the famous sixties pin up model.

“Listen Jimmy I have needs. I don’t need you to ‘guess’ you’re okay with my needs. I need a man a real man and you’re not it, so in the absence of a real man I need a man who fully supports me having a real man. One hundred percent supports MY needs, wants and desires. I need a man who doesn’t ‘guess’ he loves his wife, but knows he loves her with all his heart and soul and will do ANYTHING to please her and make her happy.

Just like in the animal kingdom there are alpha males and beta males. You clearly are a beta male and Norm clearly is an alpha male and beta males always defer and serve alpha males and their needs. Now if you can do that, fine; if you can’t then I suggest as I said earlier you leave. The choice is yours!”

Jimmy hated when she got like this but he knew she always twisted his words around to please herself and make him look like a fool and he always acquiesced as he would this time. He watched her grind the cigarette butt into the ashtray and climb back into bed. Jimmy got out of bed and went around to her side and knelt in his baby blue pajamas and held her hand.

“Peggy I love you more than the world itself. My only goal in life is to make you happy. I’m sorry if I don’t always know how to show it or say it, but I promise you, I vow to you from this day forward that your happiness will be the main goal of my life.

And if your happiness means being with Norm so he can give you things I can’t I support and encourage that. I will do everything I can to make sure you are blissfully happy. You can’t imagine how sad and inadequate I feel that I am a failure as a husband and can’t provide the husbandly duties you need to feel sexually satisfied, but I promise I will do whatever I can to make up for that, just please let me stay.”

Peggy reached out and caressed his cheek and his tiny cock twitched.

“My sweet darling husband, of course you can stay.”

She spread her legs wide. “Now as your first duty, make me feel good so I can get some sleep.”

Without question, Jimmy dove into her pussy with his tongue knowing that he was eating Norm’s leftovers. As he licked and sucked he wondered where this fantastical journey would end.


The company picnic was full of beer, barbeque, and good times. All the families were there with their kids and if last year were an indication the party would run long into the night. Peggy looked sexy as always, her skintight black pedal pushers accentuating her thick thighs and big butt, she wore a low-scooped top showing ample cleavage in her push up bra and her bare midriff. Jimmy tried to watch how much Peggy had to drink but that always ended up being a losing battle.

He watched the boys and went into the lake with them and couldn’t help but notice Peggy drinking and chatting Norm up on the shore and occasionally whispering in his ear and giggling. He made his way out of the lake and dried the boys off and got them something to eat and as he scanned the crowd he couldn’t spot Norm or Peggy anywhere.

As he fed the boys and listened to the chatter an hour had gone by when we saw them coming out of the woods. Peggy was staggering a bit and Norm was holding her by the arm.

“Hey honey! Norm was just showing me the wild life in the woods. I’m not sure but I think I saw a huge snake in there!” She burst out laughing as heads turned all of them getting the metaphor.

The night wore on and most of the partygoers gathered around the big bonfire near the lake. Kids slept on blankets huddled near their parents feet, the older ones who were still awake roasted marshmallows while the adults continued to drink and smoke. Despite the fire, Mitchell had been too cold to stay outside so Jimmy had put him in the back of the station wagon to sleep.

When he returned he saw Peggy sitting between Norm’s legs by the fire and in the darkness he swore he saw his hands roaming freely under her shirt. Despite almost twelve hours of humiliation in front of his co-workers and buddies as his wife openly flirted with another man, his tiny cock was hard and ached for relief. On the way home in the car, the boys slept soundly and Peggy put her legs out the window and laid her head in Jimmy’s lap and felt his growing hard on.

“Who’s excited? My my my!! I have to tell you I think that snake might’ve bit me in the woods and I think you’re gonna have suck all the venom out when we get home. Is that alright with you?” She purred.

“Yes dear.” Jimmy said, turning crimson as he looked at himself in the mirror.

As time went by Jimmy became more and more submissive and subservient to Peggy’s needs and wild ways. It started in the bedroom, but soon he was donning and apron and cooking and cleaning in addition to the yard work and soon, he had taken on every household chore there was to be had. Part of him resented Peggy for it, and part of him was excited about how she had taken control of his life.

Sometimes if they boys were at their aunt’s house which was often, she’d insist he wear something frilly around the house while he did his chores. Many times while he knelt scrubbing floors or doing laundry he could hear her on the phone with Norm talking about some encounter they’d had or were going to have. Inside he would rage, but then he’d feel his tiny cock twitching in his pink panties she made him wear and the world would be alright.

one Friday night, Jimmy got home late because Norm told him he had to finish the job they were working on and he’d get paid overtime, so Jimmy acquiesced and stayed on the job site by himself. When he finally got home, he found a note on the table in Peggy’s scrawl, Boys are at their auntie’s I’m heading out with the girls, be back later.

Be a good boy! He cringed when he read the last line. Be a good boy! As if he could possibly do anything to be a bad boy! Looking around the kitchen it was a disaster, plated piled high in the sink, countertops a mess, the garbage overflowing, the stove covered in grease. Rolling up his sleeves and donning his frilly flowery pink apron he began the cleanup process. After the kitchen was spic and span he moved from room to room but not before putting on the pink teddy and panties Peggy always insisted he work while doing housework.

Section 3

As he pulled the panties up his slender white legs, he marveled at how effeminate he had become. Peggy had insisted he shave his legs, chest, underarms, and virtually anywhere else hair grew except on his head. She said it turned her on knowing he was totally shaven for her while no one else could see it!

He worked his way through the house cleaning the boys room and stripping all the beds and tasing the sheets. Vacuuming and dusting was next. Finally with all the chores done and the house spotless, he made himself a cup of tea and a piece of toast and sat down on the couch. It was late, almost 10:30 and usually Peggy was home by then. He was going to go change into his baby blue pajamas, but decided to close his eyes for just a minute. The next thing he knew he heard voices and woke to find a very drunk Peggy and Norm standing in front of him. He attempted to jump up but Peggy pushed him back down on the couch.

“Well look who’s been wearing mama bear’s clothes while she’s been gone!” Norm and her both laughed uproariously as Jimmy’s face turned a crimson burning red. He checked the clock on the wall which read 1:00. Peggy attempted to stand straight without staggering her heavy lidded eyes almost falling into sleep.

“I was out with the girls and Norm showed up and we got to talking and he offered to give me a ride home. Wasn’t that nice of him?” She stared at Jimmy. “Well? Wasn’t that nice of him? The least you could do is thank him for bringing your wife home safe!”

Jimmy stammered, “N-N-Norm thank you for bringing Peggy home safe.” With that Peggy bolted for the bathroom slamming the door behind her. They could hear her wrenching and vomiting into the toilet. Jimmy scurried to the bathroom door and knocked. “Honey are you ok? Baby? Peggy? Are you okay?”

The door opened and she brushed past him and towards the bedroom. Jimmy followed her and watched her strip off her clothes and collapse onto the bed naked. He turned to escort Norm out when the big man appeared in the bedroom doorway.

“I think she’s a bit under the weather, Norm, but thank you for bringing her home.”

“That’s okay little buddy.” Norm said. Jimmy hated when he called him that, which he often did, making him feel like that dork Gilligan on that tv show.

“Well thanks again, I’ll walk you out.” Jimmy said to the unmoving Norm.

Norm reached out an placed his massive paw on Jimmy’s shoulder. “We got us a little problem here little buddy. You see your wife promised me she’d take care of me tonight and by the looks of things it appears she’s out of commission. Now someone’s gonna have to pinch hit for her and who do you think that’s gonna be?” He swung Jimmy around in his pink teddy and placed his other hand on his shoulder and began forcing him to his knees. Jim knew it was futile to resist.

Norm unzipped his pants and pulled his massive flaccid cock out. “Now I’m gonna stand here and look at your wife’s pretty naked body while you get to work on my cock.” He gave Jimmy no choice as his pushed the flesh stick into his mouth. Jimmy took it without hesitation and sucked. Norm grabbed the back of his head and thrust his big cock in and out of Jimmy’s feminine mouth while Peggy lay naked and passed out oblivious to the scene unfolding inches away from her.

When he had ejaculated into the back of Jimmy’s throat and Jimmy has swallowed ever last drop he patted him on the head the way one pats a good dog. “Good boy. He murmured. “Good boy.” And turned and left the house. Jimmy stayed kneeling on the floor, taking his tiny wet member between his thumb and forefinger and looking at his gorgeous wife drunk, naked and passed out on the bed and stroked himself until he came a tear running down his cheek.

Their lives went on like this day after day, month after month, with Jimmy become becoming more submissive and subservient to both Norm on the job and at his home and Peggy all the time. Peggy seemed to revel in the new lifestyle. She drank more, expressed her freedom with increasing regularity pushing the boundaries of the sexual revolution. Norm would often find a secluded area on the job site when no one was around and make Jimmy give him a blowjob. Peggy began to require him to wear panties under his work clothes each day.

The more they had him under their thumbs the more they both reveled in the power and the more Jimmy reveled in serving each of them. He began to really enjoy making sure his “swinging 60’s couple” was always happy. Aside from bringing them drinks and lighting their cigarettes when Norm visited he always made sure the house was clean and the boys were out of the way when they wanted to have sex.

Peggy soon discovered this newly introduced way of buying things called credit. MasterCard had just been touted as the quintessential ‘buy now, pay later’ model. And Peggy was one of their best customers. She bought the kids stuff, she bought things for the house, she even bought Norm stuff, all the while telling Jimmy that he would ‘just have to find a way to pay for it.’

Sunday morning Jimmy awoke alone in their bed, he felt next to him to see if Peggy had come home last night but she was noticeably absent. He stood and stretched noticing his reflection in the large mirror over the dresser.

His pink teddy hung on his pale white body, his face had just the slightest bit of makeup on it, which Peggy had decided would be fun for him to wear while she was out, another piece of his humiliation. Sadly he made his way to the kitchen. He stopped short when he saw Pegging sitting at the kitchen table drinking a coffee, her hair a mess, her makeup showing signs of wear. She work a flimsy black slip and nothing else.

“Good morning, my pretty sleepy head. Don’t you look nice!”

“Good morning dear. I didn’t think you had come home last night when I woke up and you weren’t there.”

“I got in late. You were passed out. I assumed correctly by looking at the whiskey bottle that you’d drowned yourself in your sorrows cause your pretty wife Peggy was out having fun. Sound familiar?” She put a pout on her face and laughed.

“Yes dear, pretty much so.” Jimmy hung his head embarrassed and poured himself a coffee hoping maybe the strong black liquid would pull the cobwebs out of his head. “Did you have a goo time last night dear? Where did you go? What did you do?” He stammered not trying to sound too demanding.

“Well not that it’s any of your business, I went out with Norm. We went to his place and fucked like rabbits. Then we went out dancing and drinking and then we went back to his place and fucked like rabbits all over again. And then I came home and slept like a baby.”

“Honey I’m glad you had a g-g-good time.”

Peggy held up her hand and cut him off. She moved the kitchen chair, spread her legs and said, “Me too! But for right now why don’t you stop your yammering and get down here and lick my pussy. I need to cum again.”

Jimmy feeling a mixture of embarrassment, jealousy, anger and arousal, knelt and gently kissed his beautiful wife’s swollen pussy lips and then dove his tongue deep inside tasting the tangy mixture of her and Norm’s love juices. As he licked he kept telling her how much he loved her and wanted her to be happy.

“Oh that’s it hubby lick me. Lick me clean.”

“Oh baby I want to make you happy. I want to make you and Norm happy. I’ll do anything for your!” Jimmy was fumbling with this tiny cock between his thumb and forefinger as he licked her.

“Good, baby cause that’s what I want to have happen. Our lives are going to be just wonderful! I went to the doctor last week and I’m pregnant!!”

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