The Haircut Encounter

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An older man has a fling with his female barber.
4.7k words
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Part 1 of the 2 part series

Updated 06/10/2023
Created 11/02/2020
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John had never regarded haircuts as anything but a regular necessity. However, as he neared the age of 60, he was growing tired of the chit chat that was required during the 30 minutes he spent in the chair.

In particular, the male barber he had visited for years began to get on his nerves. He was a nice guy but came off as a bit of a rube. Even though he knew John wasn't an outdoorsman, his barber would frequently prattle on about his hunting and fishing exploits. John decided to make a change.

He decided to try one of several national clip joints where he invariably was in the chair of a woman who was an immigrant and whose accent made it difficult to understand when she asked him questions about how he wanted his haircut. He was far from being a right winger or anti-immigrant, but he struggled to understand, and he felt bad having to ask the hairdresser to repeat herself.

Finally, he decided to try a high-end business he had heard about through radio spots. It was more expensive, but that wasn't a deal breaker. For his first appointment, he requested that whoever cut his hair would keep the conversation to a minimum. Making that request made him feel like a jerk.

He showed up for his appointment and waited briefly in the front lobby, which was tastefully appointed with leather chairs and a couch. He was informed that "Susan will be with you in a moment." He knew from the radio ads that most of the employees were female.

When Susan walked up and introduced herself, he was immediately impressed. She was tall (he guessed about 5-foot-9) and slender. Her brunette hair was full and flowing beyond her shoulders. Her eyes were dark and lovely. She was dressed in the "uniform" -- white blouse and black slacks. And it was apparent that she had been blessed with a full bosom.

John walked to her chair. She asked how he wanted his hair cut and then she went to work. No small talk. He realized that his request to limit conversation was, in this instance, pretty fucking stupid.

+++

For the next several months, John had regular appointments with Susan. On his second visit, he initiated conversation and was pleased to discover she was intelligent and had a sense of humor. During ensuing appointments, they continued to discuss mundane topics. As the visits continued, he began to imagine and wonder that if he was 30 to 35 years younger if he would have the courage to ask her for a date.

Then he got a text from Susan on his cell phone. She apologized for getting his number from the front desk, but she wanted to inform him that she was moving to a new employer. John loyally followed. After another six months or so, Susan informed him that she had saved enough money and planned to open her own one-chair shop.

"I hope you'll continue as a customer," she said with a lovely smile.

"You can count on it."

In her own shop, Susan dressed casually, and John's eyes approved. She often wore cleavage-revealing and loose-fitting tops that revealed hints of her full mounds; she always wore a bra but when he stole glances, there was always an enticing view. During spring, summer, and fall, she usually wore shorts, sometimes jean cut-offs that displayed her long, slim, tan legs. Her dark hair came down to her back and had a wild, uncombed look.

During one of his appointments, Susan off-handedly made a comment that included the words "my 44th birthday."

"Whoa, timeout," John said, looking at her in the mirror. "You're forty-four? Are you serious?"

She smiled. "Yes. What, you want to see my ID?"

"Well, I'm just surprised. Seriously, I would have guessed you were in your late twenties, maybe early thirties." He stopped short of saying anything about how young and beautiful she was because he thought that could be stepping into a minefield.

"Well, thank you, sir," she answered, still smiling. "I'll take that as a compliment."

Shortly after that revelation, John turned 61. He and his wife were set financially so he decided to retire. Their son and daughter had finished college and started their careers.

Then, his wife died of an aneurysm.

When he made his next haircut appointment, it had been a couple of months and he had gotten a bit shaggy. John explained why, telling Susan about his wife. He had never been the emotional sort so he didn't cry but she could hear the sadness in his voice.

"John, I'm so sorry," she said, moving a bit in front of the chair so they could make eye contact. "Are you doing OK?"

"I still haven't gotten over the shock, of course. And it's difficult to get used to the silence and being alone in the house..."

There wasn't much else to talk about and Susan finished doing her work. After he paid her with his usual generous tip, she placed her hand on his cheek and said, "Take care of yourself." He felt a slight shiver up his spine. "I'll be fine. Thanks."

+++

For the last three or four years of their marriage, John's wife had become less interested in sex. After her death, he found his libido was strong. And, with lots of spare time and privacy, he spent hours on the Internet, watching porn and stroking his cock. It was enjoyable exploring his fantasies but more and more it made him wish for the intimacy of being with a woman.

The next time he was due for a cut, he texted Susan. Her only available appointment was 4 p.m. the next Saturday. John had nothing else to do so he set it up.

It was early August and the temperature had been in the high 90s, low 100s for over a week. When John arrived, he was not surprised to see Susan dressed to stay cool. She wore a pair of cutoff jeans and a loose top that was low cut and had large armholes. He could see the straps of her tan bra. She had her hair gathered at the back of her head in a ponytail, the thick strands hanging down but not directly on her back.

She asked how he was getting along, and they made small talk. He told her about a comical adventure his son had gone through on his job and she laughed several times. When she finished, he paid her and was about to leave.

"You're my last appointment of the day," she said. "I'm gonna take a few minutes to close up. Would you buy a girl a drink?"

John felt a fluttering in his chest he hadn't felt in years. "Sure." He sat on a bench on a hallway outside her shop while she swept and tidied up the shop.

"There's this cool bar in my neighborhood, about 15 minutes from here. Why don't you drive and follow me there."

About 20 minutes later, they were seated at an outdoor table for two. There were misters and fans that kept the heat down. John ordered a beer and Susan ordered a cosmo. He toasted, "To better days." She responded, "To better days with more fun."

They ordered a sampler platter of appetizers. John finally found his courage and asked the question that he had thought about since he had first gotten to know Susan.

"So, you're a lovely, intelligent woman. Do you not have a significant other? Are you anti-men."

Susan laughed. "Oh, dear. No. I'm not a lesbian, if that's what you're thinking. I've had a number of serious relationships over the years, but I've never felt the urge to marry. Not really interested in being a mom. I enjoy being free to decide what kind of a relationship I want, how long it's gonna last and who it's with, man... or woman."

She then took a sip of her drink and her dark eyes sparkled as she gazed across the table. John felt his face flush. Not from embarrassment but from... what? Excitement? Lust?

"Your face is red," she teased. "Did my blunt explanation upset you? Did my admission of being bi shock you?"

After a pause, he answered. "No, not at all. I think it's hot."

"Do you now? Is your mind imagining me with a series of different men, with women, maybe in threesomes?"

"I'll be honest. After a few times having you cut my hair, I started daydreaming, asking myself if I was 30 years younger if I'd ask for your number."

"Really, now?" Susan took another sip of her drink. "Well, now you know I'm older than you thought, would you still want to ask for my number?'

"Hell yes." He blurted the words out and immediately wanted to take them back. He still considered himself a married man. It took a few seconds for him to recalibrate and realize he was a widower, a single guy, even if he was past what many would consider his expiration date.

Susan then steered the conversation to their private lives. John admitted to the fact that his marriage had been largely sexless over the last few years his wife was alive. Susan discussed a few of her longer relationships, explaining what she liked about the men she had dated, hinting at her sex life without being specific or graphic. John was left with this image: Susan was a woman who enjoyed sex, who didn't get bogged down in the entrapments that "love" can create and she called the shots. She was sexy and independent, a confident woman.

It had been a few hours -- for John, a few very enjoyable hours -- and dusk was approaching. Susan suggested it was time to go and John signaled for the check. "My treat. Thank you. This has been wonderful getting to know you better."

"What, is it almost past your bedtime, old man?" That dig was accompanied by a sexy smirk/smile. "It's not even dark yet. Would you like to come over? My place is just a couple of blocks from here. We can walk."

It was more of a demand than an invitation. John didn't even answer verbally. He shrugged and then they were walking down the street.

+++

As they walked, Susan was making small talk, but John wasn't really paying attention. His heart was thumping, and he felt short of breath as his mind imagined what might happen when they reached the privacy of her apartment. He had never had heart problems but in the back of his mind he wondered if he might be having a heart attack.

When they reached her front door, Susan punched in the pass code and entered, John following. She let the door close.

"I've always been attracted to older men," she said, turning to put her hand on the back of his neck and pull him to her face. Their lips locked, her soft full lips feeling satiny against his. Their mouths opened and their tongues tangled, each of them moaning as the kiss enflamed their passions.

When they broke the kiss, she whispered, "I thought you'd be a good kisser." He didn't answer but his hand grasped her hair and pulled her head back, exposing her long neck. He kissed, licked and nibbled her soft skin, covering her neck, moving from side to side to nip and tongue her ears.

"Mmmmmm, lover," she hissed. "That's it ... I love it."

They were hugging each other tightly and he could feel her full breasts mashed against his chest. His hands roamed up and down her back, then slipped down to cup her ass and pull her crotch hard against his. His cock was fully erect, and he assumed she could feel its hardness. She ground her mound against his bulge, a low purr coming from her throat.

Then she wiggled free of his embrace and started walking down the hallway. No words were needed. He followed her, watching the sexy sway of her ass. She turned into her bedroom and then stood at the foot of the king-size bed. Susan turned to face him.

"Undress me."

Her fingers pointed to the draw strings on each side of the bottom of her blouse. He pulled each one free, then grabbed the hem and pulled it up and over head, freeing it from her flowing locks and then tossing it aside. Her beige bra had delicate lace cups and he could see her nipples poking against the fabric. He leaned around her to unhook the clasp, then his index fingers hooked the shoulder straps and tugged the bra down her arms and off.

Susan's large natural breasts sagged but that was because of their size and gravity's pull. Her dark, button-like nipples were thick and prominent and were a perfect complement to her mounds.

John's breath hissed through his clenched teeth. "My gawd, I've wondered what your breasts looked like. They're ... beautiful."

"Why, thank you, sir." He started to reach for her mounds, but she grabbed his wrists and pushed his hands toward her shorts. "You're not done."

He quickly unsnapped and unzipped her shorts and pushed them off her hips. They slipped down her legs to her feet and stepped out of them and kicked them aside. Her beige thong barely covered her mound. Susan turned around and wiggled her ass before hooking her thumbs in the thong and slipping it down her legs. She turned around to face John.

"Your turn. Get naked."

He kicked off his deck shoes and pulled his golf shirt up and over his head. He unbuckled his belt, unsnapped the button, slid the zipper down his shorts. He skimmed his boxers down and off, his erection bobbing free.

"Mmmmm. Nice cock." John was just a bit above average, about 6 inches when hard. But it was a nicely formed penis with a round knob and a slight curve to the left. When he and his late wife had made love, that curve had always provided her with a special stimulation.

Susan crawled on the bed and John followed. They were soon entwined, kissing deep and passionately. John "mmmmed" when his hand cupped one of her large mounds, the nipple hard against his palm, then moaned as her fingers encircled and started stroking his rod.

John finally broke the kiss and started to lick and kiss his way down her neck and upper torso until he was able to capture one of her hard nubs in his mouth. It was Susan's turn to moan as his tongue flicked over the sensitive bud. He opened his mouth wide and took as much of her breast into his mouth as possible, his tongue still lapping at her nipple.

"Gaaaawd, that is sooooo nice."

He pushed her on her back so he could have access to both boobs. His hands pushed them together and his tongue licked at the deep cleavage, then moved to each nipple, flicking back and forth. Her hands cradled his head, moving through the hair that just a few hours earlier she had clipped.

"That's it, love my titties," she whispered. "Bite my nipples, slap my boobs, be a little rough."

John consented to her commands. His teeth captured one nipple and his tongue flicked over the smooth flesh. His fingers grabbed the other breast bud, squeezing it hard and twirling it. He pulled on it, lifting that breast as far as it would stretch before letting go to let it bounce and pool on her chest.

He got on his knees and grabbed her breasts in his hands, squeezing and kneading the flesh in a hard and possessive manner. Then, as she had asked, he lightly spanked and slapped her mounds, making them bounce and shake.

"YEESSSS. Loooove that. Treat me like your slutty whore."

John's cock was throbbing. He straddled her torso and leaned forward so that his dick was bobbing close to her lips. "Suck my cock. Spit on it, get it slick."

Her tongue lapped his cock knob and John thrust his hips so that his length slipped into her hot mouth. She gurgled and slobbered around his shaft. Spit dribbled from the corners of her mouth. His fingers collected that moisture and rubbed it on her nipples. Satisfied that his cock was lubed, he pulled it free with a plop and leaned back. His hands pushed her breasts together and he spit a glob into her cleavage. His cock slipped into the soft, slick valley between her mounds and he began to titty fuck her, his fingers twirling, twisting and teasing her nipples.

"AAAHGGGHHH, you naughty man. Fuck my titties."

John's cock wasn't big enough and Susan's breast flesh was too plentiful for his cock to fully clear the passage when he stroked toward her face. Susan craned her neck to try to get her tongue on his knob but couldn't reach. She contented herself with her finger rubbing his cock head on its forward stroke.

This was a new experience for John. The excitement and passion of this encounter had his balls stirring. Holding back his orgasm was already a challenge but he wanted to extend his release as long as possible.

He released his hold on her breasts and leaned back. He fisted the base of his rod and rubbed the slick, swollen nob over one of her nipples. Susan purred with delight.

John then climbed off her torso and positioned himself between her spread legs. Susan kept her patch, which was a couple of inches wide, trimmed tightly, almost like a burr haircut. His fingers rubbed over the hair until he moved a bit lower so he his face was close to her mound.

Susan's labia were meaty and prominent, a dark pink. He could already see some moisture seeping from between them in the slit of her pussy. John started his exploration by rubbing his fingers along her pubic bone, coming close to the lips at the top of her mound but not touching them. Her hips jerked in response to his teasing.

His index finger then traced around the edges of her mound, just touching the edges of her labia. "Mmmmmm, you're a devil," she whispered.

John grinned slightly. She had no idea how he loved teasing foreplay. Presented with this lovely mound, he intended to submit her to an extended session.

He moved his index finger to the top of her slit and lightly traced down her slit, just barely separating her labia. He repeated that journey a few times and each trip his finger became a bit more slickened by her juices.

Next, he used his thumbs, this time pulling apart her labia to fully expose the lighter pink flesh in the cup of her pussy mound. Her tender flesh glistened from her arousal. He could see the round bud of her clitoris exposed at the top of her mound, peeking out from its hood.

John leaned forward and the tip of his tongue made contact with Susan's vaginal lips, sliding up one side and down the other. She responded with high-pitched little whimpers as her hips writhed in pleasure.

He ran his long tongue softly and expertly along the furrow of Susan's vagina, swirling about the little rubbery mouth of her channel itself before sweeping on to flick and tease at the tingling bud of her clitoris.

Her hips bucked and rose off the bed, pushing her crotch against his face. "GAAAAWD, YESSSSS. That's the spot," she hissed through clenched teeth.

"Yeah, I know," he said, withdrawing his face that was wet with her juices. He grinned at Susan as her head snapped up to return his stare.

"You ... bastard," she whispered. "Are you gonna tease me when I'm so close."

"As a matter of fact, yes."

He lifted her left leg, so it was at a 90-degree angle to the bed and started to lick and nibble behind her knee. She shivered and her head moved from side to side, her long hair tossed back and forth. John then slowly kissed and nibbled down the soft flesh of her thigh until he reached the crease where it joined her abdomen. Her leg collapsed on the bed. Then his mouth ignored her pussy and moved to the opposite inner thigh. His lips and tongue worked on that flesh until he reached her leg, lifting it so that he could tease the flesh behind that knee.

Susan's eyes were closed, and her body was writhing. "Now that you've had your fun... would you please... eat my pussy so I can cum."

John's answer was to quickly return to her mound. Her needy pussy entrance was pulsing, and his mouth clamped on that succulent spot, his tongue diving and twirling as deep as it could. Susan's thighs clamped around his head, joined by her hands that pulled his mouth hard against her. "EHRRHHHGGAAAAHHH, eat my pussy, lover. I'm so ready to cum."

He slightly moved his mouth to the top of her slit and his lips closed on her clitoris, which had become more swollen and prominent. He lightly grasped it between his teeth and the tip of his tongue flicked back and forth over the smooth, sensitive flesh. John sensed that mouthing her clit would be the move that would push his partner over the edge.

Susan arched her back off the bed as her orgasm raced from her tingling pussy around her nervous system. "Aah-ah-ah-ah-aaahhhhhh. JJJeeeeeeesssssssuuuuusssss!! I'm ccccuuuummmmmmmmiiiiii-nnnnnngggggg! GGGGGGGGGGAAAWWWDDDDD!''

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