Jesse's Girl


Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Consensual, Fiction, Oral Sex, Anal Sex, Analingus, guy fucks old crush,guy fucks the one that got away,last fling sex story,guy fucks best friend's girl.

Desc: Erotica Sex Story: When Sean ran into an old friend, the chance encounter brought back a lot of old memories. And some fantasies as well

It was a quarter after five by the time Sean Delaney finished up his last service call for the day. The twenty-nine year old photocopier repairman had been on the go since seven o'clock and he was more than happy to call it a day. Thankfully, he had managed to route his calls so that the last one would only be a twenty-minute subway ride from home.

Walking to the train, he remembered that Valducci's Bakery was only a block past the station and decided to take a few minutes and stop there first. Back when he was a kid, his parents would drive out to Bay Ridge every Sunday morning after church for some of their pastries. For Sean, it was always the cookie assortment that got his interest. Some of those cookies, he decided, would go great with the movie on cable he was planning to watch tonight.

That the weekend was upon him and he didn't have a date no longer bothered Sean. He'd become too accustomed to it being the rule rather than the exception. It wasn't that he had some physical or other trait that repelled the opposite sex. On the contrary, most women formed an almost instant liking to him. While not exceedingly handsome, he could be called cute with a clean-shaven face and bright blue eyes. Five foot five with dark brown hair, Sean had a slim hundred and twenty pound build. It was just that he didn't have the confidence in himself to cause a woman to look at him as anything other than just a nice guy. The kind of guy you'd want for your best friend.

When he reached Valducci's, Sean found that it was more crowded than he expected it to be on Friday night. A lot of people evidently had the same idea he'd had. Still, it wasn't like he was in a hurry to get anywhere. He waited his turn and ordered a mixed assortment when his number was finally called. Handing the salesgirl a ten-dollar bill, he barely gave the short haired blonde more than a passing glance. No more than she gave him, at least at first.

He was stuffing the change into his pant's pocket when the salesgirl took a second, longer look at him. This time, a look of recognition filled her face.

"Sean?" she said in a voice just loud enough to be heard over the other customers giving their orders.

It took a moment for Sean to realize that she was speaking to him. Then another for him to really look at her and match up the face with the voice which, now that he was paying attention, was indeed familiar.

"Angelina?" he asked, not totally sure he was placing it right.

"Yes, it's me," she replied, stepping around the counter so that she could get a better look at him. "I almost didn't recognize you."

That was more than he could say about her. If she hadn't said his name, he never would've made the connection. The Angelina he remembered had long black hair and had been more than a few pounds lighter. Not that this woman, standing an inch and a half over him, weighed more than a hundred and thirty-five pounds.

"How have you been?" he asked as she leaned forward and gave him a friendly kiss on the cheek.

"Fine," she replied as she drew back, "but as you can see, there're been a few changes in my life."

"So I see," Sean agreed, indicating her new hair color and style as the safest of things to point out.

"You know that Jesse and I aren't together anymore, right?" Angelina said, jumping right to the biggest change in her life.

"Yes, I'd heard."

A loud cough from behind the counter from the bakery owners reminded Angelina that other customers were waiting. Sean took a moment to look at the tall, graying man and got the impression that he didn't like his employee's taking impromptu breaks during the busiest time of the day.

"I guess I'd better get back to work," Angelina said, motioning to her boss that she'd be right there.

"I wouldn't want to get you into trouble," Sean said, despite wishing the circumstances could've allowed them to talk a little.

"Oh don't worry about him," Angelina whispered as she leaned closer so that only Sean could hear. "His bark is a lot worse than his bite."

"Well it was nice seeing you again," Sean smiled, not wanting to get her in trouble despite what she said about the owner.

"Me too," Angelina also smiled as she turned to head back behind the counter.

Sean started for the door when a hand touched his shoulder. Turning back, he saw that Angelina was still there.

"Why don't you give me your phone number," Angelina said unexpectedly, "maybe we can have coffee or something."

Sean did just that, watching as she scribbled it down on a piece of paper. Then, promising to call him soon, she turned and hurried back to work.

Stepping out of the bakery and walking down the block to the subway station, Sean's thoughts drifted back to years past when he and Angelina had been friends. Friends that never would've been if she hadn't happened to be married to his best friend.

They'd first met when Sean was twenty and Angelina already twenty-two, two months before she had married Jesse Cassidy. It was indifference at first sight, at least in her case. Even Sean had to admit that back then he made even less of an impression on people than he did now. If it wasn't for the fact that he'd grown up with her husband to be, she wouldn't have even given him the time of day. Which would've been quite a shame seeing what good friends they became in the years to come.

Growing up on the same block, Sean had learned one great truth about Jesse Cassidy. Despite good looks and a well developed body that drew the attention of just about every girl in the neighborhood, Jesse also had the undisputed ability to be a total asshole at times. A talent that seemed only to grow after he'd gotten married.

Not to say that all of their problems were his fault. Angelina had a fair share in a number of them. The first of course was the fact that she'd gone to the altar pregnant, the reason being simple carelessness.

Not the end of the world, even back in 1984, especially since they'd already made the decision to get married. Poor family planning and an inability to keep their hands off of each other seemed to be a staple of their marriage, with Scott joining his older brother Jesse Jr. twelve months later. A daughter, Julie, a few years after that, finally led to the decision to have her tubes tied.

But in the end, a hot sex life didn't a marriage make and things began to fall apart after five years. Sean had done what he could to help, becoming as good a friend to Angelina as he had been to Jesse. Then, somewhere along the way, the twenty-five year old realized he was treading on very dangerous ground.

He'd become a confidant to both of them, listening to their problems and learning details of their marriage that an outsider normally wouldn't know about. He'd learned, for example, that Angelina had an affair with an older woman while in school, something she never felt comfortable with telling her husband about. He also learned that, as their relationship began to fall apart, Jesse had developed the habit of relieving his tensions through the oral ministrations of a very willing girl in his office.

That he had been the first to break the marriage vows in no way lessened his anger when his wife followed suit and had an affair of her own. Sean hadn't learned of this until much later because he'd stepped out of their life by that point.

The reason, although not the one he'd told either of them at the time, was that he was losing his impartiality. More and more he found himself on her side of arguments. What was worse, he found himself thinking of her in a way not conducive to just being a friend.

From the beginning, Sean had thought Angelina was pretty, but she was hardly what most guys would consider beautiful. She'd been a little on the skinny side back then, with small breasts that were hardly enough to turn a man's head. What really got a man's attention was her aggressive sexuality. Just listening to her was enough to get Sean hard and he'd lost track of the times he'd gone home and jerked off with her image in his head.

Not to say that Sean had been living the life of a monk, or had even been a virgin. Infrequent as the times had been, he still managed to share his bed with a woman now and then. But none of them, even those more conventionally beautiful, had made him as hot as Angelina did.

Running into Jesse in the old neighborhood one day last year, he'd learned what had happened since he'd seen the two of them. When Jesse told him that Angelina had an affair, Sean knew he'd been right in leaving when he did. If she had turned to him when she needed someone, he wasn't sure he would've made the right decision. At least not the one that would've made him still both their friend. Things like that were important to him, or so he'd like to think.

As the R train pulled into the station, Sean found himself wishing he'd never stopped off at Valducci's. If he hadn't run into Angelina, he wouldn't have been reminded of the downside of those days. It was just as well, he told himself, that she was never going to give him that call. If she really wanted to see him again, she would've given him her number rather than just taking his.

A half hour after walking into his apartment, Sean was sitting down to dinner. A can of chicken a la king over rice might not be gourmet fare, but he liked it. Sitting in front of the television, he had just taken his first bite when the phone rang.

"It never fails," Sean thought as he decided to let the answering machine pick up. "Just when I sit down to relax someone always..."

.... There is more of this story ...

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Story tagged with:
Ma/Fa / Consensual / Fiction / Oral Sex / Anal Sex / Analingus /