Barb at 19

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MILF Barb's early days.
23.4k words
4.52
15.4k
14

Part 1 of the 3 part series

Updated 06/11/2023
Created 11/25/2021
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Author's Note: I've done illustrations of Barb here, on Literotica. Please have a look after reading the story. It may give you an idea of what's to come.

---

"Well, the reception was nice. Certainly, more interesting than the wedding," Barb said as she allowed her husband, Ken, to open her car door.

"Two down, one to go," Ken said as he slid behind the wheel. "Is Evan even dating anyone these days?"

"I think that one girl, Rachel, went after some old guy with money and Evan had his feelings hurt," Barb said. "Maybe some day, he'll figure it out."

Tim, their oldest son, married two years earlier. His wife, Trish, reminded Barb of herself in many ways. Very adventurous. Flirty. Smart. Sexy. At least, what Barb remembered of herself twenty-some years ago.

Roger, their second son and the current groom-of-the day, married an Asian girl he met in med school. While Tammy was attractive in her own way, Barb could easily see her becoming a once-a-week lay for her son. Small tits, but a killer ass and perfect legs. Unfortunate. Tammy seemed to have so much potential. Barb guessed not everyone could be like Trish. Or her.

Her youngest son, Evan, graduated from high school, but unlike his older brothers, had very little drive to make anything of himself. He was cute, but shy, and was comfortable living with his parents a little longer. So, he opted to make coffee for a living while thinking about what to do with his life.

Barb reached over and undid her husband's fly, as was almost customary anytime they were alone, in the car, at night. Sometimes during the day, too, if she felt the need to feel him in her hands. To say her husband, Ken, was well-endowed would be an understatement. He was a big man to begin with, but in addition to being in top physical shape in his fifties, he was blessed with both the equipment and the skills to use it. Even though he was ten years older than Barb, he always outlasted her.

As she leaned over to take him in her mouth, she noticed a dark shade of lipstick about three inches down his shaft - which was about all any woman could get down their throat due to its widening girth. It was the same shade the bridesmaids agreed on.

"Which one?" Barb asked.

"All of them," Ken responded with a grin.

"Tammy, too?" Barb asked, almost expectantly.

"No, not Tammy," Ken sighed. "She's no Trish, that's for sure."

Barb took him in her mouth, sucked for awhile, and then sat back in her seat, letting him zip up his fly.

"How about you?" Ken asked, not at all disappointed that she hadn't finished. He knew there was time for that, later. While she slowed down over the last few years, she averaged three or four blowjobs a day.

Barb slipped off her high-heeled pumps and put her feet with freshly pedicured toes on the dash. She pulled up her skirt, hooked her thumbs on the sides of her bikini panties and slid them down her legs to her feet and then handed them to Ken. They were soaked in come. Ken smiled before throwing them out the window.

"The best man wasn't the best man, this time," Barb said, bringing Ken's large right hand down, between her legs. "But, it wasn't for lack of trying."

"How close did he bring you?" Ken asked.

"Close enough that a few minutes with you should take me over the edge," Barb answered, unzipping her top.

"I guess we're not waiting until we get home, then," Ken smiled.

---

Barb met Ken while working her first job out of high school as a Hooter's girl. She was used to being looked at by men two or three times her age, and she liked to tease. When Ken came in with a few coworkers for lunch one day, she was immediately attracted to him, but he wasn't at her table. She smiled at him every time she walked by, and while she had been told on more than one occasion that she had really nice boobs, she liked to think her ass was just as nice. Ken seemed to think so, too, as she caught him staring at her round butt in the mirror by the bar. He had lunch there whenever he was in town, but it was always with coworkers, which meant Barb couldn't sit and talk with just him. Finally, after dating a few regulars half the Summer, Ken finally asked her out.

"What took you so long to ask me out?" Barb asked.

"I wasn't sure if you were being flirty for you, or for the job," Ken answered.

"I'm always flirty for me," Barb insisted. "You don't have a problem with that, do you?"

"Not at all," Ken answered. "I'm always about people reaching their full potential. If you want to flirt, have at it."

"And if I like to..." Barb said quietly in his ear so the other customers couldn't hear, "fool around...?"

"Then, do that, too," Ken smiled. "I'd like to see that, though."

"So, you're not the jealous type?" Barb asked.

"No, sweetie," Ken answered. "I'm the same way. Life's too short to settle for mediocre. Spice it up."

Barb, however, was not the slut she pretended to be. She dated. She fooled around. But, she was actually on the shy side outside of work. While she might have dated a few guys, they rarely overlapped.

She had moved in with her Aunt Dori - ten zip codes away from home - after graduating from high school, and started paying rent as soon as she landed the Hooters knock-off waitress job. The agreement was that as long as she paid rent, Dori kept what she did and with whom to herself.

Barb thought about continuing school, but wasn't very book smart. She could figure out just about anything, but the idea of sitting in an auditorium, listening to a professor drone on and on did not seem like any kind of life for her.

For the first few months, serving hot wings paid the paltry rent her aunt requested, and covered a car payment. She could afford a gym membership, and clothes that she liked. She had what most men would call "berthing hips," a tiny waist, and full, natural D-cup boobs. The other girls asked her how she managed to keep her stomach so flat while eating whatever she wanted, and she always replied "genetics." She did gymnastics all through high school, so her legs were always a little larger and muscular, but her boobs kept her from doing some of the events that would have gotten her scholarships - not that she would have used them. She kept her blonde hair a little longer than shoulder length, and always went with minimal make-up. She was frequently mistaken for the younger version of Elizabeth Shue - but with more curves - and she took that as a compliment. Her blue-grey eyes captivated anyone that looked into them... if they ever bothered looking up from her tits. At 5' 4" and 130 lbs, she knew she wasn't tall enough to make it as a model, but that didn't keep her from posing for the local restaurant calendar.

Everyone had their favorite girl, and Barb had enough of a following to stay in good standing with the manager.

She spent most of her time off on her own, not really clicking with any of her coworkers. She'd get as much sun wherever and whenever she could, but she seemed to freckle more than tan in some areas. Her Aunt Dori's back yard wasn't particularly private, so she never managed an "all over" tan, but the tiny bikinis she experimented with came pretty close.

When she finally went on a date with Ken, it was on a boat, on a lake. She forgot that the only bikinis she owned were suitable for sunning, and not at all suitable for swimming. When they got around to taking off their shorts and t-shirts a few hundred yards off shore, Ken dropped anchor and let out a whistle.

"You like?" Barb asked as she turned, showing off the tiny bikini bottom. Ken nodded, admiring her incredible ass.

When she pulled off her t-shirt, Ken let out another whistle.

The tiny triangles of the front of her bikini top were just barely big enough to cover her small, hardened areolae.

"Don't stop there," Ken said, grinning and pulling off his shirt.

"You first," Barb laughed. "Besides, it's our first date and you still haven't told me what you do for a living, or where you got this boat."

Ken gave her a "fair enough" look, and reached into the cooler for beer. He offered one to Barb, who let it rub against a nipple, making it stick out almost half an inch.

"You know I'm not old enough to drink, right?" Barb asked.

"But you're old enough to fool around?" Ken asked.

At 29, Ken maintained a heavyweight boxer's build. He was well over six feet tall, but his shoulders were broad, and arms thick and muscular, making him just look like a normal guy, scaled up a size or two. He was hairier than she would have imagined, and wondered what all that hair would feel like against her soft skin.

His Bahama surfer shorts went down to his knees, but what really caught her eyes was the developing bulge that went down his right leg almost as low as his shorts.

Barb hadn't had an orgasm in almost three weeks, and the sight of Ken's bulge made her pussy wet with anticipation. Maybe not for that day. Maybe not for that night. But, eventually, she really wanted to know what it would feel like to have something that big inside her.

"It was favor day," Ken said, bringing Barb out of her trance.

"W-What?" Barb stammered.

"The boat," Ken continued. "I helped a friend of mine clean it up after he bought it at an auction, and in exchange, he lets me take it out once in awhile."

"That's nice of him," Barb said, unable to take her eyes off his crotch. She couldn't help herself, and finally realized how her customers must have felt. "And nice that he lets you borrow it. It's nice." She felt like a dumb blonde saying 'nice' so many times.

"As for what I do," Ken continued. "I do a little of this and that. I don't really have to work, anymore, but we all like our toys, right?"

Barb nodded, not knowing at all what he was talking about. She couldn't pull her eyes from his groin.

Ken took a sip of his beer, looked around, and then jumped off the side of the boat.

Barb stood up, making her boobs bounce and tested the bikini's ability to stay in place.

Ken resurfaced on the other side of the boat, then swam to the back and pulled himself back into the boat. His shorts clung to his legs, perfectly outlining a swollen cock.

"That felt good," Ken said, reaching for his beer. "Want to go for a quick dip?"

"Not quick..." Barb started to say.

"Oh, hell," Ken said, standing up and undoing the drawstring to his shorts. "You're not gonna be happy until you see it." He pulled his shorts down, revealing the largest example of manhood Barb had ever seen.

"Happy?" Ken said as he sat down on a towel on the vinyl cushion bench, just out of sight of any passing boats.

Barb made no attempt to hide the wet spot that formed in the crotch of her bikini bottom.

"Wow," Barb said in a hushed tone. "That's... really big."

"Kinda stating the obvious, aren't we?" Ken smiled, and held his shaft as if inviting her to inspect it further.

"Do you want to, ummm..." Barb asked.

"What?" Ken asked in return. "Do I want to what?"

"You know..." Barb moved closer.

"Fool around?" Ken answered with a question.

"Yeah," Barb said, reaching behind her and untying her bikini top. "But, I normally don't..."

"I don't care what you normally," Ken said. "Agreeing to come with me on the boat for a date led me to believe you might be interested in fooling around, but I didn't know how bad until I saw you in that little bikini. Now that I see how wet your pussy is, what are we waiting for?"

"I don't normally fool around that far on a first date," Barb finished. "I thought you might want to play with my boobs while putting suntan lotion on me, but that was about it."

"I'll play with your boobs, Barb, if that what it takes," Ken smiled. Barb's eyes were glued to his stiffening dick which he released and allowed to bob in her general direction. She couldn't believe it was still getting harder and more erect. "But maybe what you really need right now is a good pussy-licking?"

Ken stood up and motioned for Barb to take his place on the cushioned bench seat. Her shoulders barely cleared the side of the boat. She slouched and spread her legs as Ken knelt between her thighs.

He pulled the strings on both sides of her hips and Barb raised her butt, letting him toss the bottoms aside.

She pulled the top over her head and tossed it in the same direction as her bottoms.

She had recently waxed her labia, leaving just a small runway of short, blonde hair above her clit. He must have approved, and Ken's mouth was on her in seconds.

Barb enjoyed whenever a guy gave it his all when he went down on her. It motivated her to give it her all when it came time to return the favor. But, Ken was taking things to a whole new level. His fingers found their way inside her increasingly wet pussy, turned, and pressed directly on her g-spot.

Barb groaned and Ken looked up to see her closing her eyes and pinching her nipples as her toes curled on either side of him.

It wasn't the most intense orgasm Barb had ever had, but it was certainly one of the quickest.

"Like that?" Ken asked as he stood in front of her and took another sip of beer.

"Couldn't you tell?" Barb asked, covering her nipples with her folded arms, and crossing her legs.

Once again, she was mesmerized by his manhood, now jutting out in front of him, almost perfectly straight, easily ten inches long and as wide as her beer can. The head was wet with pre-come, and she wondered if he had brought condoms. She had, but they would not have fit him, and she wasn't planning on getting fucked, anyway. Plans change, though.

"Do you have any condoms?" Barb asked.

"No," Ken answered. "Do you?"

"Nothing that would fit you," Barb pointed at his cock, which was starting to angle upward ever so slightly.

"You give head, don't you?" Ken asked. He stood there, waiting, and Barb finally understood he expected her to blow him right then and there. She grabbed one of the life vests and put in on the floor of the boat in front of him, then knelt on the vest as she took this shaft in both hands and worked the head into her mouth. His pre-come tasted good. His shaft tasted a little bit like lake water, too, but the reason for that was obvious. She couldn't believe how hard the shaft was. The head was soft and very easy to kiss and roll her tongue over, but the vein-covered shaft felt stiffer than any dildo she had every played with. She fondled his balls as best she could, but his sack was bigger than her hand. She could only imagine how much was going to fill her mouth whenever he did come.

"You on the pill?" Ken asked before taking another sip of beer.

Barb let the head of his shaft pop out of her mouth and said, "No. I really wish I was though."

"Are you gonna get on the pill?" Ken asked, putting his beer down and grabbing hold of his cock and stroking it into her mouth.

He held the back of her head with his other hand, so she could only answer with a nod.

"Good," Ken said, and then pushed his cock in her mouth harder as he came down her throat. Barb swallowed as fast as she could to keep up, knowing if she didn't, she'd either throw up or come would start bubbling out her nose. When she had thought he had finished, he surprised her with another load, and then another.

When he finally finished, her face and boobs were covered with come.

"Nice look," Ken said. "Get used to it or go on the pill."

"I don't mind being covered in your come," Barb said, not wiping any from her face or boobs, but instead reaching for her barely-touched beer. "But, I'm definitely going on the pill."

Ken let her finish her beer before going down on her again. She came even faster the second time, but he opted to not let her blow him again afterward.

Instead, Ken threw her bikini in the lake, and Barb dove in after it. She held the bottoms in her mouth while she tied the top behind her back underwater, then tied the sides of the bottoms. When she pulled herself back inside the boat, she had put the bottoms on backwards so the triangle was in back and the g-string was in front, riding up her pussy crack.

She dried off in the sun, eventually taking off her bikini and putting on her shorts and t-shirt sans underwear or bra. Her boobs bounced freely under the thin material of the shirt, and as the wind picked up, her nipples hardened enough to be clearly visible beneath the material.

She helped Ken put the boat on the trailer, being a fast learner, and Ken drove her to her aunt's house.

"Thank you for a very fun date," Barb smiled, boobs bouncing as she grabbed her bag from the back of the truck and escorted Ken to the front porch.

"And thank you, Barb, for the delicious pussy," Ken said loud enough for Barb's aunt to hear on the other side of the house.

Barb's face blushed, but her pussy also tingled when he said that. She hit him in the arm, kissed him on the cheek, then the lips, and then with an open mouth as she brought his hand under her shirt. His other hand pulled down her shorts... which fell to her ankles. She stepped out of one leg opening of the shorts as his fingers found her wetness. A flip flop fell off as she lifted one foot to the front porch railing. She let him finger fuck her on the front porch for several minutes until she came on his hand.

He withdrew his hand, licking his fingers, and she stepped back into her shorts and pulled them up.

Barb looked at him, hard, and then smiled without saying another word. She went inside, closing the door behind her, and watched through the window as he walked down the steps, got into the truck, and drove away.

With Summer gone and Fall in full swing, Barb hadn't seen nor heard from Ken since their date at the lake. She went on a few dates with some of the customers that she thought could keep their jealousy under control, but the guys were frequently just average and boring. Sure, some were cute, and one or two were well hung, but they always seemed more into themselves than they were into her.

Barb was always good for a handjob following - or during - a date. If her date treated her to dinner, she'd give him a blowjob. If it was a good dinner, she swallowed. If it was dinner and a movie, or a concert, sex in his car. If it was really different and interesting, sex at his place or at a motel, but she never spent the night if she could help it.

She had been on the pill for almost two months, and wondered why she bothered. Her periods were shorter and more predictable, which was convenient. And, her boobs might have felt a little bigger. But all the boys - as that's what she thought of anyone 19-28 years old - almost always used condoms. She wasn't sure if they were worried about getting her pregnant, or were worried she was the type of girl that would pass on a disease.

Her aunt put her in touch with a gynecologist shortly after Barb moved in. The gynecologist was a good-looking woman in her late fifties, and was adamant about STD testing on a regular basis for younger women, especially if they were promiscuous but hoped to have a family some day. That was Barb.

Barb was helping the other girls take down the Halloween decorations at the restaurant when Ken showed up, alone, dressed like he was going on a date. He looked and smelled good.

"Hi!" Barb said, a little too enthusiastically.

"Hey, Barb," Ken replied. "How are you?"

"Great!," Barb replied, eyes going from his face to his crotch uncontrollably. "Where have you been? I was worried about you."

"Oh, I've been around," Ken said. "Busy season at work." Barb noticed he hadn't sat at one of her tables.

"Well, it's good to see you, Ken," Barb said, and walked over to another table full of wide-eyed men undressing her with their eyes.

She found herself being extra flirty with other customers - something she normally kept in check. She looked over at the girl waiting on Ken - for what felt like three or four hours - and she could have sworn the girl put her hand on the bulge extending down his right pant leg. She became sure of it when the girl rubbed her hand up and down the bulge.