Jesse's Girl

by Ann Douglas

Copyright© 2005 by Ann Douglas. All rights reserved.

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

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.

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..."

"Hi Sean, it's Angelina," the familiar voice said from the speaker, "I was hoping to catch you at home but it is after all Friday night and you probably have a lot better things to do than chat with an old friend..."

"Angie, it's me," Sean said, using her old nickname as he grabbed the receiver, "I just walked in the door."

Listening to her say how glad she was that she caught him, Sean wondered why he felt the need to lie to her about what he was doing. It wasn't as if he was ashamed about the life he led.

" ... so I was thinking," Angelina went on, "if you don't have any plans, maybe you'd like to come over for a late dinner and we could catch up. I understand that it's really short notice and you must already have..."

"No, that would be great," Sean interrupted her.

"Are you sure?" Angelina asked.

"Absolutely," Sean insisted. "I didn't have anything planned that couldn't wait until tomorrow."

This time he was telling the truth. It wasn't like the movie he was planning to watch wouldn't be on at least a dozen other times in the next week.

"Would eight o' clock be all right?"

"That would be fine," Sean answered.

Angelina quickly gave him her address, which he recognized as the apartment that she and Jesse had been living in when they were married. It was a great home for the kids, so it made sense that she'd kept it.

"Can I bring anything?" Sean asked.

"Just your appetite," Angelina assured him.

Hanging up the phone, Sean picked up his plate and headed for the kitchen. He scraped the plate into the trash, thinking that it was a pity that he hated rice when it was heated up as leftovers. Not wasting food was something his mother had repeatedly drilled into him when he was growing up.

Deciding a shower and a change of clothes was in order, he stripped off the pants and shirt he'd worn during the day and turned on the water. Dropping his clothes into the hamper, he was surprised to discover that beneath his briefs he had suddenly grown hard.

"I guess she still has that effect on me," he laughed as he considered how silly that sounded after all this time.

Pausing before he stepped under the hot water, Sean reached down and ran his fingers along the length of his seven-inch cock. Seeing the effect just talking to her on the phone had on him, it might not be a bad idea to dampen his hormones before heading over there. Given his recent dry spell, it had, he remembered, been over four months since he'd gotten laid, it didn't take long at all for him to take care of business. That out of the way, he stepped into the shower. As he washed the after effects off his body, he only felt a little guilty that it had been Angelina's face he had visualized as he jerked off.

Soon enough he was dressed and out the door and as he headed over to the avenue to catch the bus, he decided to stop at Freedman's Ice Cream Pallor and pick up some dessert. Despite what Angelina said, he could hardly show up empty handed and somehow bringing the cookies from Valducci's didn't seem right.

It took a few minutes to recall, but he remembered all the kid's favorites and got a pint of each, as well as one of pistachio that he knew Angelina loved. Hopefully the bus would be on time and nothing would melt.

It was on time for a change and fifteen minutes later he was standing in front of the six-family building he used to visit like a second home. Ringing the bell, he only had to wait a few seconds before he was buzzed in and he walked up the familiar stairs to the second floor left apartment.

"I hope I'm not too early," Sean said as Angelina opened the door.

Seeing her standing there in a T-shirt and shorts, Sean was glad he'd dressed just as casually, having tossed on a polo shirt and jeans. One thing hadn't changed over the years he was glad to see. Because of her small bust size, Angelina hardly ever bothered with a bra.

"You're right on time," Angelina said as he stepped inside, "I was just about to take dinner out of the oven and ... what are those?" she asked, taking note of the bags in his arm.

"I stopped at Freedman's for dessert," Sean smiled. "I hope I remembered what everyone liked."

"Oh Sean, I should've told you," Angelina said in an apologetic tone. "This is Jesse's weekend to have the kids, he picked them up an hour ago to take over to his mother's."

"That's okay," Sean replied, trying to hide his disappointment. "We can just put it all in the freezer and they can have it during the week."

"I know they're going to be so sorry to have missed you," Angelina continued as she picked up the bags and headed for the refrigerator. "They all really like you."

"It's okay, I'm sure there'll be another time."

"Look on the bright side," Angelina smiled as she closed the freezer door, "with no little kids around you can tell me all the sexy details of your love life. A cute guy like you must be getting laid just about every night of the week."

"Only if you count in my dreams," Sean laughed, remembering how open Angelina was in her conversation.

"I find that hard to believe," she laughed as well. "While I'm here, would you like a beer to go with dinner?"

Sean said that would be fine and Angelina took two bottles from the refrigerator. Setting them on the table, she insisted that he take a seat at the table and let her serve the dinner, brushing aside his offer to help.

"Nonsense, you're my guest," she said as she removed a casserole dish from the oven. "This is all very last minute so I hope you don't mind macaroni and cheese."

"That happens to be one of my favorite dishes," he assured her.

"You're a liar and you know it," Angelina grinned as she set it on the center of the table, "but I'll let you get away with it this time as not to hurt my feelings."

"This is really good," Sean said as he took his first mouthful of macaroni.

"Thank you," she said as she took a taste of her own. "Do you know that when I first met you, the only appliance I knew how to use in the kitchen was the phone to order take out. With three kids, that was the first thing that had to change."

"Yeah, I remember," Sean replied, thinking that the woman across from him had been a real Italian Princess back then.

"So tell me, what are you doing now?" she asked.

It didn't take long for Sean to recount the story of his life, such as it was. Then the conversation shifted to people they both knew, which of course included her now ex-husband, Jesse.

"Jesse had mentioned that he'd run into you a few months ago," Angelina said as she took a long drink from her beer. "So I guess he gave you the lowdown on what happened between us."

"Well his version at least," Sean said, trying to be diplomatic. It would hardly be polite dinner conversation to refer to his hostess as 'that cheating bitch', which was the nicest of the terms Jesse had used.

"I'll bet," Angelina laughed, "and you know what, I'll bet part of it was even true."

"Truth is sometimes a matter of perception," Sean noted as he finished up his meal.

"So now you're a philosopher," Angelina noted in return.

"Well you know I like to read a lot," came his reply.

"I remember," Angelina grinned as she cleared the last of her plate. "I think you used to read more in a week than I did in a year."

"Not everyone is a reader," Sean offered in the way of a balm, "especially not in the age of video."

"That's one thing I always liked about you," Angelina countered as she cleared the table. "You always said the nicest things to a girl."

Sean just laughed.

"Why don't you get us some fresh beers and I'll meet you on the couch," Angelina suggested as she put the dishes in the sink. "We can continue the sad story of Jesse and Angelina."

"It wasn't all sad was it?" Sean asked as Angelina joined him on the couch, taking one of the cold beers he had gotten from the fridge.

"No, not all sad," Angelina said as she took a long pull on the bottle. "There were some good times too, especially in the beginning. They just seemed to be less and less as the years went by. Toward the end, it seemed like all we had in common was great sex. Then at the very end, we were having it with different people."

Not wanting to comment on that aspect in case there was something Jesse had told him that Angelina still didn't know, Sean just drank his beer and let her go on. Which she did for the next ten minutes, telling him all the details of her own affair and what she knew of Jesse's.

"You know, I really missed this," Angelina said as she got up to get two fresh bottles. "You and I just sitting and talking. I could tell you anything and I know you would never tell anyone else."

"Well, I think it's important to keep someone's trust if they give it to you."

"There are few guys like you left, Sean," Angelina said as she handled him another bottle, even though his was only half empty.

They drank together in silence for a few minutes, then Angelina picked up almost where she'd left off.

"You're also a lot more understanding than most men," Angelina went on. "Jesse would've had a shit fit if he ever knew about that fling I had with Ms. Johnson back when I was modeling clothes in high school. He can be really homophobic at times you know, and she was most definitely a dyke."

"Well he wasn't an angel back then either," Sean pointed out, "and anyway, that was before the two of you met."

"You're not telling me that Jesse had some dark skeletons in his past that I don't know about, are you," Angelina exclaimed, her face lighting up, "maybe a little boy/boy play somewhere way back when?"

"No, at least none that I know of," Sean answered, realizing a few moments later that she was pulling his leg.

"Too bad," Angelina said, making a face as she did, "if he had it might've changed the course of our marriage."

"I don't understand," Sean said, more than a little confused.

"Well I didn't share every secret with you back then," Angelina smiled, "but I guess there's no reason to keep this one anymore."

Filled with curiosity, Sean took another long drink and waited for Angelina to again continue her story. It turned out to be one well worth waiting for.

"Back when things began to fall apart, not long before you stepped out of the picture, Jesse and I did make one last attempt to put it all back together," she began, pausing twice to take a drink. "Unfortunately, we did that by concentrating on what did work in our marriage - namely our sex life. Somehow, we got the foolish idea that if we spice up that, everything else would sort of fall in place."

"Spice it up how?"

"Well it was little things at first, playing games and then later we also started using toys," Angelina answered.

"Can I ask what kind of toys?" Sean wondered.

"Vibrators, sometimes restraints, eventually even dildos," she answered.

Sean let out a loud sigh as not to let out that he'd already heard some of this before.

"Then we got a little kinky..." Angelina continued.

"Then they got a little kinky?" Sean thought, totally enthralled by the additional revelations.

" ... We had a three-way with another woman."

"Anyone I know?" Sean asked automatically, then apologized for asking.

"No reason why I shouldn't tell you now," Angelina countered, "it was Wendy."

"Wendy," Sean repeated, "Wendy Harris?"

"The one and only."

"Wow."

Wendy Harris was to Angelina what Sean had been to Jesse, best friends. The two had been inseparable for most of their lives, until Wendy finally met the guy of her dreams on a European vacation and moved to London with him.

"It turned out that Jesse's aversion to same sex contact didn't extend to a ménage-à-trois with his wife and her maid of honor," Angelina laughed. "He got so turned on when he saw me go down on Wendy that he pretty much came right then and there. But of course he was able to get it right up again at the prospect of fucking Wendy."

Remembering how hot Wendy looked the first time he had met her at the rehearsal dinner, Sean could well understand Jesse's reaction.

"It was funny when I thought about it later, but he never even stopped to consider why it was so easy for me and Wendy to make love to each other," Angelina said. "It was like he just assumed that every girl was automatically into each other."

"Some guys are dumb enough to think that," Sean grinned as he finished off his beer, then thought to ask, "does that mean that you and Wendy had..."

"Not like me and Ms. Johnson," Angelina explained, "but we had made out a few times when we were in school, just kissing and stuff. Nothing really heavy."

"Oh," Sean replied, declining with a wave of his hand Angelina's offer of another bottle. "But I'm getting a little confused here. What did you and Jesse sleeping with Wendy have to do with what you said before about it might've been better if Jesse had played around with a guy?"

"I'm coming to that part," Angelina explained, putting her own bottle down and deciding that she'd had enough as well.

Sean, meanwhile, wished she hadn't mentioned coming, seeing as the images her revelations had filled his mind with had also given him one hell of a hard on. Like Jesse in her story, it wouldn't take much more for him to stain his underwear.

"After we'd had our little fling with Wendy," Angelina started again, "I wanted to do it again. Only this time, I wanted the third party to be a guy. I'd never been fucked by two guys at once and really wondered what it was like."

"And Jesse had a big problem with that," Sean concluded, knowing his friend as he did.

"Not at first," Angelina said surprisingly. "I guess the idea of watching me and another guy kind of turned him on. I've heard a lot of guys get off on watching their wife or girlfriend service another guy, I was just a little surprised that Jesse would be one of them."

"Then what happened?"

"Well, I guess I made the mistake of... , no it wasn't a mistake since I was just speaking my mind about it."

Sean was confused again.

"I simply pointed out to Jesse that if we were going to have another three-way, I expected it to be a real three-way and not just him and another guy fucking me," she explained. "After all, it wasn't just Wendy and I doing him."

"Now I understand," Sean said as the cloud in his head cleared.

"I mean, I didn't expect him to bend over and let the other guy fuck his ass," Angelina said, her tone suggesting to Sean that despite what she said, that was something she would indeed have liked to see, "but I did expect him to at least go down on him, and vice-versa."

"And then it was downhill from there?" Sean asked.

"Well, not right away," Angelina replied. "In fact, we did talk about the possibility for a month or so. But once we started fighting about that, the floodgates opened and all the other arguments came pouring out as well. Then we both turned to other people and you know the rest."

Sean sat there for a few moments, wondering what do you say after a story like that. Then he realized he still had a question he was curious about.

"Angie," He said hesitantly, "if you don't mind my asking, I'm just curious about who you were planning to have as the guest star in your second ménage? I mean, if you were talking about it that long, you must've had someone in mind."

"I thought you might be curious," Angelina laughed, picking up her bottle and despite what she had decided a few minutes before, drained the last of it.

Then, picking up Sean's bottle as well, she walked over to the garbage pail next to the kitchen counter and dropped both in. Turning back, she started to give him an answer.

"Well obviously, we couldn't ask our best man," she said, "not with it having been Jesse's brother. That would've been a little too kinky even for me."

That was a relief, Sean thought, because Scott Cassidy had indeed been one of the names that, improbable as it might seem at first, had flashed through his mind. He now wondered if he was right in the other name that had popped up with Scott's. Jonathan Armstrong was almost as close a friend to the two of them had he'd been, and he was the one that Angelina had the affair with.

"I bet you think it was Jonathan, don't you?" Angelina said as she sat down next to him.

"Actually yes," Sean admitted, thinking now that had to be wrong from the way she said it.

"That's a pretty good guess, especially since I did fuck him later on," Angelina said, "but he would've been all wrong for a ménage. I could never imagine Jesse ever getting comfortable enough with Jon to ever just get naked with him, much less play around."

"Then who?" Sean asked, figuring that since she was talking about it, it was a question she was willing to answer.

"I can't believe you can't guess."

"Was it someone I knew?"

"Yes, you knew him quite well."

Mentally, Sean tried to run down the names of people from their circle of a few years ago. He even reviewed what he remembered of Angelina's neighbors, thinking that they might've been more comfortable with someone who actually wasn't that close. But who in that category would he have known that well?

"All right, it's obvious that you're not going to get it so I guess I'll just have to tell you," Angelina grinned. "It was you, silly."

"Me?" Sean said in disbelief.

"Yes, you," Angelina repeated. "Do you find that so shocking?"

"I ... I'm not sure."

"You can't tell me that back then, you didn't want to fuck me in the worst way," Angelina added.

"Yes, I mean no, I mean I wouldn't have," Sean babbled.

"It's okay, Sean, I always knew how you felt about me," she said, moving closer and taking hold of his arm to show it didn't bother her. "In fact, I later realized that most of that was my fault. I must've sent you home more times that I could count with a case of blue balls, parading half naked around the apartment and sharing my most intimate secrets."

"You knew?"

"Well eventually," Angelina said. "but not until after you disappeared from our life. I mean I guess I always knew, but didn't know what I knew."

"I understand."

"So can I ask a question now?"

"Of course."

"If I had asked you, what would you have said?"

"I'm not sure I understand what you're asking," Sean said in reply, unsure if she was still talking about the ménage-à-trois or just sleeping with her in general.

"Me and Jesse," Angelina clarified. "If we had asked you, what would you have said."

"I guess I would've said yes," Sean replied, wondering if that would've indeed been his answer.

"Even with what I said about my wanting Jesse and the guy we were with to play around as well?" she added. "I'm just curious about your reaction to something like that. Or is that something that you've actually done?"

"No, I haven't," Sean answered. "Not that I think there's anything wrong about what anyone does with someone else. It's just not something I've ever been in a position to try."

"So you would've been cool about being with Jesse and me?" Angelina repeated, extremely curious about the might have been.

"I guess I would've been okay with it," Sean said, now more sure about his answer. "After all, with you in bed with us, it wouldn't be like it was just me and another guy."

"That's exactly what I tried to get Jesse to see," Angelina exclaimed, "but he couldn't see it that way."

 
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