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Author's Notes

"Jay learns about Julie’s gambling past while she spends the evening with her second boyfriend Brad."

Jay hopped into his Jeep Cherokee and made his way towards the gym for his daily workout. He was still smiling from the long session of sex he had just had with Julie.

When he got to the gym, he grabbed his bag and made his way through the main entrance, past reception and into the main weight room.  This was a nice gym, not some ratty old dungeon.  There were big windows everywhere letting in light, and along the wall a long row of treadmills looking through the glass down onto the city street below; it was bright and clean.  In the background was the sound of music and the distant clanging of weights typical of a gym.

As he approached the dumbbell rack, an attractive woman wearing tight spandex shorts with fake boobs gave him an admiring look; she was hot.  Her eyes scanned his body first and then met his dark eyes.  She flashed him the small, subtle smile that women use to let a man know that they’re interested but Jay didn’t give a damn.  He had zero interest in other women.  He was over the moon for Julie Koop and only Julie Koop. He no longer found other women attractive.

As he placed his gym bag down on the ground, getting ready for a hard set of dumbbell curls, he heard a familiar voice next to him.

“What’s up, Jay?”

It was his friend Kaden, one of the regulars at his local gym and a fellow personal trainer. He was a good guy and Jay liked him.  Sometimes after a workout, they would hit up a local pub and have a few drinks.

“Hey Kaden, what’s up?” Jay replied.

“Not much.  It’s leg day, so what can I say? Everyone hates training legs, right?”

Jay nodded in agreement.

“My day's off to a great fucking start. I just got back from pound town.  Just spent the last hour hammering my girlfriend’s pussy,” Jay said.

Jay could be cocky and arrogant around other men, but had a sweeter disposition around women.

“Sweet! Are you still dating that girl with the big ass?” Kaden asked.

“Yeah.  I can barely keep up with her, she’s horny as fuck, but I’ll die trying.”

Jay picked up a pair of forty-pound dumbbells from the rack and began performing a set of curls.  His 18-inch biceps were looking good. He was wearing a tank top and his arms were on display for all to see. His triceps were bulging with the triangular shape that well-developed bodybuilders display on the back of their arms.  His biceps were long, extending down from his shoulder to the elbow. When he flexed them, they contracted into a nice sexy peak that would drive any woman crazy with desire.  He had a physique that would place very high in a bodybuilding contest.

Kaden didn’t interrupt Jay and let him finish his set.  He watched Jay push through to the point of failure, that moment when another repetition is impossible.  His intensity in the gym was admirable.

“So hey, did that girlfriend of yours ever get that little gambling problem of hers under control?” Kaden asked.

Jay looked slightly startled.

“What??” He asked.

“Julie Koop right?”

“Yeah…”

“She used to hang out at Cascades Casino a lot, quite the regular. Always had men throwing themselves at her.  I doubt she’s ever paid for a drink in her life.  I used to see her there all the time, used to sit with her at the Glacier Bar, she likes her tequila, that chick.  Always the expensive stuff too.  Personally, I fucking hate Patron.”

Jay stood listening to Kaden speak, feeling slightly miffed.  He was waiting for Kaden to continue.  Kaden was getting ready to perform some dumbbell curls as well.  He grabbed a pair of thirty-five-pounders and placed them down on a bench in front of him.

Kaden continued, “In the end though, she cut herself off, she self-excluded which was probably a good thing considering how much cash she used to throw down at the roulette table, you know I always wondered where she got her money.”

“How do you know her?” Jay asked.

“I used to work with her at the Hook And Ladder Pub, I was bartending and she was a server there at the time.  Good one too!”

Kaden picked up the dumbbells that he had placed on the bench, banged out a hard set of dumbbell curls and placed the dumbbells back down.

Jay was standing with a blank expression and staring off into space. He looked deep in thought.  Julie had never told him much about her past, and up until this point in time, he didn’t care. He always believed that somebody’s past was in the past, but for some reason, this news was bothering him.  He had lost interest in his workout.

“A heavy gambler, huh?” Jay said quietly.

“Seemed like it.  We’d go to the casino after a shift at the Pub, we always had a good time, but she threw the cash around.”

Jay suddenly changed the subject.

“Are you still dating that crazy little blonde?” he asked Kaden.

“Nope.  Too crazy for me, brother. She wanted to peg me, man. You know what that is, right? It’s when a chick wants to bang you in the ass with one of those big strap-on dick things.  Your worst nightmare, right?”

Jay laughed instinctively, but his mood had changed.  His newfound knowledge about Julie’s past gambling problem had rattled him.

“No, my worst nightmare is waking up without my penis.”

Kaden had a good laugh.

“Fine then, your second-worst nightmare.”

Jay had completely lost his desire for conversation and his workout. He grabbed his gym bag and gave Kaden a fist bump.

“It was good to see you again, bro.”

And with that, Jay abandoned his workout and left the gym.

*********************

When Brad got home from work, he was happy to see Julie’s red Mustang sitting in his driveway. He had no problem at all with Julie letting herself in whenever she liked, that’s why he had given her a key.

At thirty-eight-years old, Brad Rossi had a net worth of ten million dollars from a construction company he and a friend started when they were twenty-one-years old. Brad was a hard-working man, and as a result, he owned a large, beautiful house and a small fleet of expensive vehicles.  He lived alone and loved it. He had no desire to marry or have children.

He opened the massive double oak doors to his home, walking across the marble floor of the foyer. He passed through the large, spacious kitchen and made his way onto the back patio where the pool was.  The first thing he saw was Julie Koop suntanning in a blue thong bikini.  The warm sun had caused her to doze off, so Brad stood admiring her for just a moment or two.

First, he admired her bronze skin, which was getting darker and darker as spring progressed.  Julie had some Latin blood in her family, and because of that, she tanned extremely quickly.  Usually by late summer her skin was so dark that she almost looked African-American,  except of course for the blue eyes.

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Next, he let his eyes drift up to the oversized breasts that had gently sunk into her body since she was lying on her back.  A skimpy blue bikini top held them in place.

“What a gorgeous young woman she is,” he thought to himself.

It was obvious to Brad that she had recently gained some weight.  At this point, he didn’t mind because she tended to hold it so well.  Julie was one of those women who was blessed with a physique that seemed to store fat in all the right places.  Even though she had gained ten pounds in recent months, most of it was evenly distributed across her ass, thighs and boobs, her stomach remained relatively flat, although even that was starting to show a few signs of weight gain.

Brad attempted to sneak up on her, but before he made it to the sun lounger, she opened her eyes and smiled.

“Hi baby,” she said with that soft, sexy voice she was known for.

Brad grabbed a small deck chair and sat next to her.  He briefly looked out at the sprawling green fields on the other side of the pool that stretched into the distance, and at three small horses gently nibbling on the grass.

Brad had built his dream house on a large lot with no other houses in sight. He owned ten acres on which he had built two small barns and several small fenced-off paddocks for horses; of which he owned three.  He had bought the horses for an ex-girlfriend, and while he didn’t care so much for them, he loved the country feel they added to his estate.  His swimming pool had a diving cliff and a large waterfall that could be turned on with the flick of a switch, but he rarely used it.  He worked too much and too hard.

“How was your day, babe?” she asked.

“Stressful.”

“Aww, I hate to hear that.”

Julie stroked his biceps.

“We’re building a skyscraper right now in the heart of the city, thirty stories of steel and glass.  It’s the biggest project I’ve ever worked on, for sure, and to make matters worse, there’s a massive shipment of steel girders that's been delayed. Don’t get me started on the problems I’m having with the union either.  These lazy fucks that don’t wanna work, they’re pushing for a sixty-minute lunch break right now and to make matters worse, there’s a possibility of a strike coming up.  Their union wants a ten percent increase in pay, that’s on top of the five percent they got last year.”

This is what Julie loved about Brad, and this is something Jay couldn’t offer her. Jay was a fuck boy plain and simple, he spent most of his time tanning, lifting weights and playing video games.  Brad, on the other hand, was an intelligent and well-read entrepreneur who worked like a mule and was very ambitious.  His money didn’t hurt either.  Brad had a way of bringing out Julie‘s more intellectual side and she liked that.

“How was your day?” he asked her in return.

Her mind immediately wandered back to the sex she’d had with Jay earlier in the day and felt her clit tingle. She quickly made something up.  Julie hadn’t told either Jay or Brad that she was sleeping with both of them.  Dating two men at the same time was a beautiful thing and she loved it, but having to constantly tell small white lies to keep both men in the dark could be stressful at times.  Still, she felt minimal guilt.  It would be ridiculous for any one man to satisfy her either sexually or emotionally.  Lately, she had been considering taking on a third lover.

“Just hanging out here.  I’ve been here all day.”

“Keeping an eye on the horses for me?” he asked.

“Mmhmm…”

Both Jay and Brad had beautiful cocks and Julie loved them both equally. Jay was seven inches and circumcised, and he got rock hard and stayed that way.  Brad's cock was slightly shorter but thicker, and he was uncut.  She had the best of both worlds and enjoyed pleasuring both men.

While Brad‘s work had afforded him a beautiful big house, and all the trappings of wealth like swimming pools, tennis courts and sports cars, he was often too stressed out and tired for sex.  Sometimes Brad would experience mid-session letdowns where his cock would start to soften halfway through lovemaking.  Julie could usually get him hard again by bringing her lips down onto his cock for a few minutes and giving him a slow erotic blowjob, but he didn’t have Jay’s stamina.

What she did like about Brad was his ability to engage in deeper conversations, whether it be about politics or philosophy, or even running his business. Brad was an older soul than Jay.  He was more romantic, and would often hold her in his arms for an hour or more after having sex while Jay, on the other hand, had a hyper-unfocused mind and couldn’t stay in one place for long.

Brad's wealth made him more attractive as well.  His house was Julie‘s house too, so in effect, she had a mansion of her own.  Often when Brad was away for business, she lived there and had the place to herself for weeks at a time.

“Alright. I’m gonna leave you to soak up some more rays.  I’m going to take a shower and have a power nap. I’m fucking beat,” he said.

Julie just smiled.

After his shower, Brad walked into his bedroom just as Julie was coming up the staircase that led to the upper floor.  Brad was naked and Julie was still wearing her blue thong bikini.  They spoke no words, they had an effortless chemistry that could speak for them. She pressed her lips to his, and for a moment or two, they enjoyed some deep romantic kissing before collapsing on the bed. And for the second time that day, Julie had a hard dick in her pussy.

It was a short fuck session, a quick twenty minutes, but it was enough for Julie to cum three times.  She finished Brad off with a slow teasing hand job that brought him to orgasm and emptied his balls, leaving hot white cum all over his stomach and Julie’s right hand.

As Brad’s orgasm subsided, Julie made sure to squeeze the head of his dick a few final times to make sure every last drop of his seed had been squeezed clean out of his dick. She could feel his cock starting to gently soften in her hand. She brought her warm mouth down on his softening shaft, making the most of his post-orgasmic sensitivity, and giving him that final little twitch of pleasure.

Julie rolled over and lay next to Brad, her heart rate was starting to slow down.

“I so needed that after a long, stressful day,” he said.

“Mmm.  Me too, babe.”

For Julie, it had been a day that had seen her have fifteen orgasms!  Eleven of those orgasms had been with Jay, three with Brad, and one from a vibrating car seat.

Julie spent the rest of the day at Brad‘s house, and the two of them sat next to his pool watching the sun go down, casting a red glow across the evening sky.

Published 
Written by Jade_Pillow
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