It was sometime in the fall of 1985 and Kelly and I were both twenty-five. Kelly and her mom had always been close. Almost sister-like close, which struck me as odd since she had an older sister, although the age difference left them with little in common, plus Kelly was the youngest of four in the family and her mom was twenty-seven when Kelly arrived. She wasn’t a teen mom (to Kelly) with only a few years age difference.

Nonetheless, Kelly shared nearly her (our) entire life with her mom. Within a few months of losing her virginity, her mom knew the story. While still in high school, Kelly had shared that she’d had multiple sex partners. It was sometime later before I knew all of this. In retrospect though, things added up.

Her folks seemed almost too cool to the fact that as teenagers we fucked like bunnies in their house. Her parents actually thought I was the best bet they had for keeping Kelly on a path away from becoming a drop-out, addict, teenage hooker. While it said little for Kelly (which will be addressed here shortly), it did explain why they liked me so damn much.

Kelly was pretty, not model-freak gorgeous, but a Midwestern pretty girl at five-two with super long, straight, dishwater-blonde hair that hung to the backs of her knees. She hadn’t cut off any length since she was seven. Everyone saw her tits coming before they saw her. They were 34F jugs that stuck straight out with nice pink nipples which, when aroused, would darken and look like red peanut M&M’s. She shaved her bush while still in high school and had kept it that way ever since. And no one filled a pair of low-rise bell-bottom jeans like Kelly with her firm little bubble butt jutting out just above her hips.

Kelly had a smile that was half-smirk. You always knew there was more going on inside her head than she let on. While half was a smirk, the other half of her smile was raw sex appeal. It was nearly impossible to look at Kelly and not have a sexual thought, regardless of your gender.

That lead to one of life’s big questions for Kelly: Was she the way she was because the 1970’s culture and her body caused everyone around her to sexualize her, so she just went with it, or was the true Kelly a deeply sexual person that God had graced with a body to match?

It was a Saturday afternoon while I was out of town that Kelly was at her mom’s. Her dad was off to another bowling tournament. They did what they always did: talk as though they had to cover every topic imaginable. Kelly had popped a bottle of wine and they sat out in the backyard.

The mood and moment seemed right and Kelly brought up her nagging question of whether she was born to “think with her pussy”, as she put it, or did the expectations of those around her mold her to who she was. Her mom, to Kelly’s surprise, reacted with a hearty belly laugh. It took her a few minutes to compose herself.

“We should talk. Hit me,” as she passed her wine glass to Kelly. “You remember grandma?” Kelly knew she meant ‘Mags,’ as everyone called her father’s mother Margaret. Mags lived with the family for about a decade starting around the time Kelly was born. She passed when Kelly was ten years old. Kelly remembered that Mags (which is what she insisted even the grandkids call her) had a huge mane of red hair. She had seen her after her bath and her wet hair hung down to her waist. When dry it almost looked like a giant Irish wig it was such a bright, huge mane. Kelly thought her hair was beautiful and was always disappointed with her own.

Mags liked to drink. It usually took two bottles of vodka to get through a week. Mags also had, apparently, never owned a bra. That fact was pretty obvious. Since Mags usually only wore a robe, or house-coat as she called them, at home, it was hard to not notice that she had two giant cantaloupe-size melons wrestling around inside.

“You know, that for years, everyone has said that you remind them of Mags.” Yes, Kelly knew that, but was also never quite clear what was meant? It usually carried a chuckle, or a knowing glance between others, that told her there was more to the story.

“Yes, and why is that?” Kelly asked.

“It started with your fiery spirit when you were little. You always knew what you wanted to do and what you were willing to do and cared not one bit what others said or thought. And then by the time you’d grown up, the physical resemblance was incredible.”

Kelly interrupted, “But she had that beautiful red hair!”

“Which was very long," as she made eyes at Kelly’s mane, some of which was lying on the grass, "She also had huge boobs and a very curvy figure which looked exactly like yours. Mags also loved sex. Especially when she was a young woman. She was a very wild child. Your father and I were always scared to holy hell that you’d turn out just like her. In many ways you have. I guess we’re the ones that had to figure out that it’s not so bad.”

Kelly popped her fists on her hips, “Oh really? But, how would you know that she loved sex?” That comment had Kelly intrigued and seeing that the wine bottle was empty, Kelly excused herself to grab a second. With another glass of wine and plenty of instigating by Kelly, her mom saw that Kelly was serious, and more than that, probably deserved to hear the stories. They spent the next four hours covering as much ground as her mom could remember from the stories that a juiced-up Mags would tell her during their time in the house alone while Kelly’s dad was at work and the kids were in school.

Kelly shared this one with me…

Mags was a bored sixteen-year-old in a little shit-hole town in northwest Illinois which consisted of a railroad crossing, a church, and two former bars. One had been converted to a general store and the other sold ice cream. Mags would hang around there after school just looking for anything to do.

She said it was his black slicked-back hair that caught her eye. He made pretty clear that it was her bosom that caught his. She had seen him once or twice before late in the afternoon at the ice cream store, in the back with the owner, and then leave out the front door, but without ice cream.

That day he said, “Those are some jazzy B’s” to her as he walked past. She felt the redness swell in her face. She was embarrassed to have a grown man call out her boobs. Yet, at the same time, she felt that familiar dampness form between her legs. She rode her bicycle back home and squished herself around on the seat as much as she could to find that special feeling.

“Jazzy B’s” stuck so hard in her head she could think of hardly anything else that week. Mags had let a couple of the guys at school feel her up. She loved how it felt to have her nipples pulled and tugged. Yet, once they got themselves hard all they wanted was to shove her face into their crotch and squirt their juice into her mouth. She’d spit it out as soon as they finished. But those were just stupid high school boys. This was a grown, good-looking, man who actually commented on her boobs.

He was back the following week, on the same day, she noticed. Mags had worked hard with a hairbrush to get her hair under control and not looking quite so wild. She was sitting on the front stoop. He winked as he approached her, then walked past and into the store. She thought it odd that he parked by the back door but walked in through the front door.

A short time later he exited the store, turned around, and spoke to her boobs. He asked if she’d like to go for a spin in his car. She demurred but he promised he would stay close. It was only when she said “yes” that he noticed she had eyes.

She jumped into the passenger seat and as he drove his eyes spent more time staring at her jugs than at the dusty excuse of a road. “What do you do for fun?” he asked.

“Nothing,” she replied, “this is the most boring place on earth.” He pulled off the road and stopped near a stream. He leaned over and one hand reached behind her neck pulling her in for a kiss. The other flicked a couple of buttons open on her shirt and pawed at her huge tits. Mags had messed around with a couple of classmates but had never been taken by a man. She melted and kissed him back, perhaps too passionately, perhaps too needy.

He flicked a couple of more buttons and had her shirt wide open. He broke their kiss, stared at her boobs, and softly whistled. He enjoyed the sight of her large pink areola. He also seemed to like how her nipples had quickly come to attention. He lunged his mouth onto one and then the other. He sucked them in as hard as he could and then pulled his face away keeping the nipple in his mouth and watched as it lifted her heavy breast as he tugged. The suction would finally let go and he smiled mightily at the erect and elongated nipple that was left to entice him to do it again.

Mags started to feel something familiar, yet completely unknown at the same time. Her cunt was wet, of that she was sure. Yet, the special feeling she could get rubbing it on her bicycle seat was happening without her rubbing on anything. He was ravaging her boobs with his mouth and both hands, quickly from one to the other. Her breathing became difficult. She felt like her vision was closing in, blackness closing off everything except what was straight in front of her. She thought perhaps she was fainting. But it all felt so incredibly good. Her arms unwittingly held his head tight to her chest. She heaved hard, gasped, heaved again, and then moaned too loudly. Her legs shook. She started to hyperventilate, having no idea what that even was.

It finally hit a crescendo and she moaned loudly again and then was immediately embarrassed as she thought she had peed her trousers.

“Son of a bitch! Did you come off?” His grin was wicked.

“I, I'm not sure what happened?”

As he quickly opened his slacks he introduced himself as 'Jack.' Mags' mouth dropped open. She had played with those two boys from school. She had sucked their cocks. She even let one push just the tip of his cock into her slit just one time and then he tugged it himself until it spit his sticky mess onto her butt. She made him wipe it off with his shirt. She had even walked in on an older brother tugging on his cock in the barn and watched until he noticed her and screamed for her to get out.

Mags thought she knew something about hard-ons. She had never seen anything like what Jack had laying on his thigh. Many times, in later years she would say, “A sausage like that needed a bun.” Jack’s cock was much longer than her hand and as he pulled her down toward it, she found her fingers could barely wrap all the way around its girth.

Jack stroked his cock as he pushed her mouth onto its head. He didn’t last but a moment in her mouth. Again, her past experience was of no help. His cock started to throb and shot, forcefully, one stream after another, after another, after another, after another into her mouth. His hand had her head pushed down past the head of his cock. She felt her lips stretch as the ball-bat was shoved further into her mouth.

Jack kept her there until his cock stopped throbbing. She could feel it start to contract a small bit. “Have you ever done that before?” he asked. She shook her head slightly, indicating no. And it was truthful. Nothing ever like that.

It contracted a bit more. The hand stayed in place. “Swallow it.” Her brain couldn’t even comprehend. She shook her head again to indicate no. “Swallow it.” The hand pushed her head further onto his cock. It was by then perhaps only three-fourths of what it had been moments ago. “Go on! You ain’t getting up until it’s gone and you’re not making a mess on my slacks.”

His tone was severe and she knew he meant what he said. She took a gulp. She didn’t die. She took a second, followed by a third. She didn’t even throw up. It wasn’t peach cobbler, but it wasn’t horrible either. Jack moaned softly as her mouth moved on his cock as she swallowed his jizz.

He released the pressure from her head. She didn’t raise her head. She found herself enjoying the feeling of his cock in her mouth. It continued to release small drips which she cleared with her tongue and swallowed without thought.

Eventually his cock shrunk to the size of the other boys’ hard-ons. Convinced she had captured every single last drop, she suctioned her lips over his cock, as he had done with her nipples until it released with a pop.

“You have honestly never done this before?” Again, she shook her head no. “Well, you are a fucking born natural.” Jack put away his cock and started up the car. He was on the road and Mags' boobs were bouncing all over as she struggled to get her shirt buttoned and tucked in. He dropped her off at the ice cream shop. “I’m here every Thursday,” although Mags had already figured that out.

She rubbed her wet pussy onto the bike seat through her wet trousers as she rode home. She had another one of those shuddering feelings she could sometimes get with her bike, but it was nothing compared to what Jack had done with her boobs.

She met up with Jack every Thursday for weeks after that. He taught her how to really suck cock. He talked her through how to open her throat and get past her gag reflex. She absolutely beamed with pride the first time she shoved her nose into his curly black pubes as his sausage erupted straight into her throat. Jack was in seventh heaven and she didn’t even have a mouthful of mess to swallow. He kissed her so hard and deep that his tongue nearly tickled her tummy from the inside.

For once, her boring life had some excitement. Mags felt like a woman. Proud of how she was pleasing a man who said he was twenty-eight years old. Proud of knowing that she could suck and swallow a massive cock and a huge load (she believed Jack when he confided that his cock was, in fact, much larger than other men's.) She had also admitted that she had let those other boys dribble their little loads in her mouth, but clearly wasn’t lying when she said she’d never done anything before like taking Jack’s mammoth cock. Jack had to take her word that his loads were ten times the amount of her school chum’s.

The following week, after she had deep-throated him, Jack was very interested in her crotch during their petting session. She had her tits out and Jack was driving her close to orgasm again just by playing with her nipples. He had found the spot, over her trousers, and was rubbing it hard with his hand. Mags knew it felt great but after a few minutes, her lube had made her trousers so wet that they started to hurt a bit.

Clearly, it would feel better with her pants out of the way. She unbuttoned them. Jack lit up like a kid at Christmas. He quickly helped her tug them to her knees and then push them off, onto the floor of the car. As he brought his head back up he suddenly stopped and exclaimed, “Holy fucking firecrackers!”

Mags was caught off guard. What was so wrong with her cunt that made this man, whose cock she’d come to adore, shout out at the sight of it. Unconsciously, she pulled her knees tightly together hiding access to her slot.

“You’ve got a firecracker for a cunt!” Jack seemed elated rather than disgusted. Again unconsciously, she let her knees relax and her cunt opened wide. “I’m so stupid. With the red hair, I shouldn’t be surprised at all. It’s the prettiest cunt I’ve ever seen.” Jack shifted her around sideways on the small car seat. He lifted one leg behind his head and spread her thighs as far apart as they could go.

He spent the next half an hour playing in her pussy. Tugging on her long red hairs, which while long, compared to the black-haired cunts of Italians, Mags had much, much less hair. Her pussy hair was more like a Mohawk. It was easy to view her bright pink pussy lips that became even pinker as Jack played with her. Jack was absolutely enamored with her pussy. Considering how she felt about his cock, she understood.

Jack was Italian. Had never hung around with an Irish girl. Even at his age, he had discovered something new. He wanted the whole package and helped Mags struggle out of her shirt. It was the first time she’d ever been completely naked in front of a man. She was flabbergasted when he opened the car door and tugged her hand pulling her out of the car.

Jack’s slacks fell to the ground around his ankles. He turned Mags around so that she leaned inside the car door with her hands on the car seat and her butt aimed at Jack. She couldn’t believe how wet Jack had made her cunt. His cock was at full hard-on, she bent down and looked through her legs as he rubbed his huge head against her gash, getting his head slicked up. Then he held it against her hole and slowly pushed forward. Mags gasped.

That was nothing like a schoolboy dipping his cockhead into her wet hole. She felt her cunt stretch as it never had in her life. She could hardly breathe. Jack kept pushing forward, slowly, but without pause. She felt his huge ball sack touch her slit. She was shocked. “Is it all in?”

“Yeah.”

She felt her face redden with pride. Again, her body had done something she wasn’t convinced was possible. Jack paused for a moment and then started making small in-and-out strokes. She couldn’t believe how good it all felt. Her cunt kept making lube, so much that it started to drip, making strings until they got caught by Jack’s hairy balls.

Within a couple of minutes, Jack was bashing his body against her ass with a great deal of force. His strong hands gripped her waist. Mags felt that feeling rise again that only Jack could bring her. She dropped her face to the car seat and moaned, loudly, over and over and Jack made her come, and come, and come. The last come was so strong that she felt a blast of wetness blow out of her pussy. Jack felt it hit his balls. “Fuck!” he roared and Mags felt throb after throb after throb as his long fat cock pumped squirt after squirt of come into her cunt, replacing all the liquid she had just blasted out.

Jack collapsed onto her back after his balls had emptied. He stayed there until Mags sneezed from the dust in the air and squirted his cock out of her red hole. She felt a huge flow of come slide out and fall with a splat onto the dirt.

Jack helped her stand up. She faced him as he pulled up his slacks, put his cock away, and straightened his shirt. Jack smiled as he studied her nude body. “You’re the sexiest dame I’ve ever seen.” Inside, Mags just melted.

They continued to meet every Thursday, even after school had let out. Mags caught holy hell for not being around to do chores but didn’t give a single shit. Jack only had about an hour after his visit at the ice cream store before he had to head back to Chicago. Both of them made sure they spent as much of that time fucking as possible. Conversation was fine, as long as his cock was in her pussy while they had one.

Jack’s small amount of information spoke volumes. Mags was no dummy. She pieced together the bits and pieces from around town. Jack was the weekly liquor/cash contact. The ice cream parlor had a speakeasy in the basement that operated on Friday and Saturday nights. Coming from Chicago meant he was, of course, part of the Capone organization. To sixteen-year-old Mags, it all just made him even more exciting and sexy.

By July she had decided to say goodbye to her family, a final year of dreadful high school, and move to Chicago to be with Jack as his girlfriend. She was in Chicago for the next three years and had tales to tell for the rest of her life. Nearly all of which she had told to Kelly’s mom and many of which had been shared that afternoon with Kelly.

Kelly’s question had, for the most part, been answered. As her mom said, “You come by it honestly,” meaning she was born with the genetic history of Mags. It gave Kelly a bit of peace knowing that she was living her life, in some ways, as destined. She stopped her questioning and continues to live in great comfort and confidence knowing she is who she is meant to be.