High School Reunion

***All characters are over 18 and are fictional. Any resemblance to any real-life persons or situations is purely coincidental.

...

Connor's phone had been blowing up all day, all about the upcoming 10-year high school reunion. Half the texts were from all of his friends from high school, including his twin sister, Sarah, all talking about how excited they were for the reunion. Half of them haven't seen each other in years since they moved away for work or family mostly; the only time they see each other these days is through social media posts. Everyone was sharing old pictures from high school, asking who else they might see at the reunion, sharing gossip about others, and so on.

The other half of the texts that Connor was receiving were in a separate chat group, mostly between all the guys. The reason this chat group was separate was because they didn't want their female friends in the main group to read what they were talking about. Connor was OK with this because, according to his sister, the women had their own side chat group as well. As far as Connor knew, both sides had their own chat groups going about the reunion, and possibly other groups were going that other people didn't know about as well.

The main reason that Connor and his guy friends were using their own chat group was to talk about the women they hoped to see again at the reunion. It was mostly about the girls they dated back in high school, the ones they hoped to see again. Some of those who aren't married hoped to hook up with an old girlfriend during the reunion, or even just someone they used to crush on.

One main woman that kept coming up was Ruby Warden, probably one of their most successful classmates. Right after high school, she went off to Los Angeles with the dream of becoming an actress. Unlike some people who failed in that dream and went back home with their tales between their legs, she actually made it.

Ruby was best friends with Sarah throughout middle school and high school, who Connor always had the biggest crush on. He did ask her out a few times over the years, but she always made a polite excuse to turn him down. He was OK with it because, over time, they had become good friends themselves.

Ruby was a few inches shorter than Connor, with shoulder-length red hair and an athletic body. She was on the school's swim team with Sarah and always kept in good shape. Despite eventually becoming friends with her, Connor could never get over how good she looked in a swimsuit. She had decent C-cup breasts, a small waist, and a great ass.

Ruby was in the drama club and featured in all of the high school plays. On the side, mostly in the summer, she did some modeling and even managed to do a few TV commercials over the years. She wanted to do more, but her parents insisted she finish high school first, much to her dismay. But right after graduation, she went right off to Los Angeles. She was already 18 by then, so there was nothing to stop her from going out to pursue her dreams.

Her parents hoped she would at least consider going to college while she tried to be an actress, but the only classes Ruby was interested in were acting classes to improve her skills. They did convince her to at least stay with her aunt in Hollywood, who was also an actress with a decent career. Ruby liked that idea because she got a free place to stay and got to live with someone who could mentor her in her career.

Her early years were off to a rocky start, doing mostly extra work or low-budget independent films, but she eventually got some good TV appearances and a few supporting roles in some smaller films that often went straight to video or Netflix. She also did some plays on the side, and was briefly part of a traveling improv group. To keep herself financially secure, she continued modeling and did a few more commercials.

Eventually, she got her big break in a drama series on HBO where she played the paralegal for a criminal defense lawyer. Her character was funny and sweet, and she had a lot of good lines. It was a shock to the audience that her character was murdered near the end of the first season when she found evidence that the defendant who was featured throughout the first season was guilty all along. That role earned her an Emmy nomination for best supporting actress in a drama.

After that, she got a lot more work in film and television. She never got to A-list status, but she was consistently getting more work and a lot of other famous celebrities. She even had a decent social media following; just under a million followers on Instagram alone.

Despite how well Ruby had been doing for herself, Connor's friends didn't seem to care much about her acting talent as they did about how hot she was. Mostly, they seemed to care about the nude scenes that she had done over the years. Ruby appeared nude in three movies and in one episode of the TV show she got famous for. All but one of those scenes were tasteful and essential to the plot.

Her only gratuitous nude scene was from her early years when she was still trying to make it as an actress, and it happened in a straight-to-Netflix movie about a college frat party gone wild. The movie was in the vein of most college movies about fraternities, with a humorous plot, ridiculous but loveable characters, and the fraternity trying to stay on campus despite the college Dean trying to shut them down. Despite how it was just no different than any other kind of college movie like that, it was still a lot of fun to watch.

Ruby was a supporting character in that movie. She played a strait-laced nerdy type who learns to put away her books and have some fun. Her character gets drunk and does a striptease on a pool table during the party scene. That scene was all anyone could talk about when it came out. Connor's male friends made a lot of sexist comments in the chat group after that came up. Connor never participated in those comments, just stating that he did enjoy the scene. He didn't want to admit that he actually rewatched that scene more than two dozen times.

But Connor didn't care about those nude scenes, despite how he secretly enjoyed them. He saw everything she had done since she left for L.A. and thought she was a wonderful actress. He always thought that if given the right role, she could easily become an A-list celebrity.

Connor made sure to mention that in the chat group with his guy friends. They all agreed that despite what they were saying about how hot she was, they still thought she was a great actress and mentioned some of their favorite roles she had done, before going back to commenting on her ass again.

Connor was excited to see everyone at the reunion, especially Ruby. They followed each other on social media and had commented on each other's posts over the years, but they hadn't seen each other personally in ten years.

The main reason he wanted to see her was not just because of an old crush he had on her, but to apologize to her for an incident that happened between them all those years ago.

TEN YEARS EARLIER

Connor remembers that date exactly. It was the first Saturday of June; just a few days earlier, everyone had graduated from high school. One of their rich friends had a lake house nearby, and he convinced his parents to have a party there to celebrate. It was going to be an all-nighter, so everyone had to be prepared to stay over or make plans to get rides home. There was going to be alcohol, despite how mostly everyone there was going to be under 21. All the parents were made aware of this, but were OK with it because arrangements were made to supervise the guests to make sure nothing got out of hand and nobody would be driving home themselves since this was a few years before Uber or other rideshare companies came into existence.

The music in the lake house was getting too much for Connor, so he went out to the porch. That's where he found Ruby with his sister Sarah and some of their other friends. Ruby was wearing a black summer dress with a red floral print. They all had a beer or something alcoholic in their hand, and each one was discussing what they were planning to do during the summer and what they'd be doing in college.

When it was Ruby's turn, she let everyone know she would be leaving in less than a week for L.A. She talked about staying with her aunt and how she planned on fulfilling her career goals. Everybody raised their drinks Everyone in that small group raised a drink as a toast to wish Ruby good luck, and she thanked everyone for it.

Over the next hour, the group dissipated as everyone went off to dance, drink more, or hook up with someone. Soon it was just Conner, Sarah, and Ruby alone together.

"So, you're not going to even consider college?" Sarah asked.

"I just don't think it's for me," Ruby answered. "I may consider it down the road if it doesn't work out for me, but for now I want to focus on being an actress."

Connor chimed in. "At least you have a rent-free place to stay when you get there. So, you're already doing better than most people who run off to Hollywood."

Ruby laughed and found that positively encouraging for her career prospects already.

A song that Ruby loved started to play inside the lake house, and she insisted that the three of them go back inside to dance together. They danced through a few songs before Sarah left them alone together.

Connor and Ruby had another drink together, then danced some more, then another drink and more dancing. Eventually, they found themselves on the couch making out together. They weren't drunk, maybe a little buzzed, but they knew what they were doing at that point of the night. When they were done, they danced for a couple of more songs before Ruby grabbed Connor by the arm and dragged him away.

"Where are you taking me?" Connor asked.

"It's a surprise."

Ruby took him upstairs to the third floor and down to the end of the hallway. Connor had no idea what she was planning, but he let her lead the way to see what happened. Ruby found the room she was looking for, made Connor go inside, and locked the door behind them. It was one of the guest bedrooms in the house.

Connor now had an idea of what Ruby had in mind for them. Before he could say anything, she kissed him again, more passionately than when they were making out earlier. She guided Connor to the bed, and they fell onto the mattress while still holding each other in their passionate embrace.

Everything was going well until Ruby started going for Connor's pants. He knew she really wanted to have sex with him right then and there, but he suddenly got nervous about the whole situation. What Ruby didn't know about Connor, and many other people didn't know about him, was that he was still a virgin.

He had never had the opportunity with some of the women he had dated in the past. He always dated women who some considered to be "good girls" who didn't do those kinds of things. There were some girls who were, as some might say, very easy, but he never liked those types of girls. He did get the occasional blowjob, but never went any farther than that. He did convince them to at least let him tell his friends that they slept together, so nobody would know he was still a virgin. They were OK with it because, despite wanting to save themselves, they still got societal pressure to have sex and didn't want people to know they were virgins as well.

Connor really wanted to sleep with Ruby at that moment, but was suddenly afraid that he wouldn't be able to perform as well as she might have liked. He knew of a few guys she had slept with, all of them jocks and most likely to show her a good time in bed.

Connor stopped Ruby from trying to take off his pants and sat up on the edge of the bed.

"What's wrong?" Ruby asked as she sat up herself.

"I just think we should take it easy."

"Why?" she asked with a quizzical look.

"I just think we're going too fast, that's all."

She gave him a quizzical look; she didn't expect him to say something like that. Connor couldn't believe it himself; this was his dream girl and he was asking to take it slow. He suddenly felt like the girl in the relationship right now.

"Are you gay?" she asked.

"What? No, of course not."

"It's OK if you're gay," she said. "I always wanted a gay guy friend."

"Trust me, I'm not gay."

"OK, that makes sense from what your previous girlfriends told me about how good you are in bed."

"I'm glad they spoke so highly of me," said Connor.

"So, if you're not gay, then why do you want to take it slow?"

"I just think we're moving too fast, that's all."

Connor was too embarrassed to say he was still a virgin. He was sure most 18-year-olds were still virgins, but it was still a hard thing to admit to. He thought about admitting it to her, but after hearing what she said about what his ex-girlfriends said about him, he couldn't admit that it was all a lie.

"Maybe we should just go back to the party," said Connor.

Ruby stood up from the bed and faced Connor as she quickly unzipped the back of her dress and let it fall to the ground. There she stood, wearing a sexy black bra and matching thong. It was the sexiest sight he had ever seen in his young life.

"Are you really going to turn this down?" She asked with a sultry smile.

Connor didn't say anything, but his face told Ruby all that she wanted. She got back on the bed with him and they started making out again. Ruby got Connors' shirt off as he took off her bra and began fondling her breasts. Despite being a virgin, he did get to feel a couple of his ex-girlfriends' breasts on a few occasions, but they didn't hold a candle to how wonderful Ruby's breasts were.

Again, Ruby went for Connor's pants, managing to rip off his belt; but when she tried to go for the zipper, he got scared again and stopped her.

"What's wrong?" she asked, feeling very annoyed. "I'm on the pill if that's what you're concerned about."

"That's not it," he told her.

"Then why don't you want to fuck me?"

Connor just couldn't admit out loud that he was a virgin. He considered that she would understand, but was just too embarrassed to say it.

"I just think we could hold off on this for a while," he told her.

"I'm leaving for Los Angeles in less than a week," she replied.

"Then maybe we could wait until you come back for a visit."

Ruby was shocked by that response, and Connor was not proud of it either.

"You know what, forget it," she told him.

"Are you sure?"

"Yes, let's just go back to the party."

Connor was relieved, but at the same time, upset with himself for turning down this opportunity. And he could tell that Ruby was way more disappointed in the situation than he was, even if she wasn't admitting it.

They got dressed without saying anything to each other, except when Ruby asked him to zip her dress back up for her. They left the room and went back downstairs to the party. They didn't see each other for the rest of the night. At one point, Connor sought her out to talk to her about what happened between them, but Sarah told him she had left a while ago.

They didn't even say goodbye to each other when she finally left.

THE PRESENT

Over the next ten years, Connor learned to mostly let go of what happened that night, and he hoped that Ruby didn't think too much about it either. He hoped to finally explain himself and apologize to her for being such a dumbass.

He was sure she would forgive him. She accepted his follow request on Facebook and occasionally commented on each other's posts and reacted to them as well. It was a small thing, but he felt it meant things were moving in the right direction in their friendship.

Conner, of course, eventually did lose his virginity in his first semester in college to the first girlfriend he had. It didn't last long, but he had a great time with her. He then slept with one more woman he dated in his second semester, and after that he slept with several women throughout his college life. He eventually learned to stop caring about only dating women he sleeps with and instead enjoy the occasional hookup with women who just wanted to have fun.

After college, he learned to settle down and date women on a regular basis before sleeping with them. He was almost married several times, but it never worked out.

On the night of the reunion, he went with his sister Sarah in the same Uber in case they had too much to drink. They spent that time reminiscing about their high school days and who they hoped to meet. They even shared some juicy gossip about what some of their old classmates have been up to since graduation. When Sarah mentioned Ruby's name, he tried to change the subject to another classmate.

The reunion was at a banquet hall of a five-star hotel. From what they understood, many of the rooms were booked by the returning senior class who were coming from out of town. When they got there, they got their name tags that had their old senior photos on them and cringed when they saw how dorky they used to look back then.

In the banquet hall, they immediately ran into many of their old friends, and everyone began hugging each other and catching up on what they've been up to. Over the years, Ruby and Sarah remained friends, often visiting each other. When Sarah had to briefly stay in Los Angeles for her job for a few months, she stayed with Ruby, and they had a spectacular time together.

It wasn't long before Ruby showed up and she and Sarah ran into each other's arms. They jumped around as they hugged and squealed like they were high school teenagers again. Ruby greeted everyone she recognized, some of whom mentioned how much they loved her movies and what their favorite roles were.

She finally got around to Connor, who was still very nervous about seeing her after all these years. When she saw him, she gave him a big hug and said how much she missed seeing him, which made Connor feel more relaxed when she said that.

"It's great to see you again, Ruby," said Connor. "I'm sure you've heard this enough tonight, but I also need to say it. I've seen everything you have done since you went off to L.A."

"Thank you," she said, smiling. "And I've been following your career as the youngest person to become a CFO for a major tech company. You've done really well for yourself."

"Thank you."

They spoke for a little longer before more people she recognized came by and insisted they have drinks together. She went off with them, and Connor smiled, knowing she didn't seem to hold any grudges against him.

Throughout the night, there was a lot of dancing, drinking, pictures being taken and, of course, reminiscing about the good ole days. Connor even got to dance with Ruby for a few songs before they went their separate ways again.

Later in the night, when Connor was sitting at a table, having a drink while watching everyone having fun. His feet were tired from all the dancing, so he took a much-needed break. It wasn't long before Ruby came by and sat next to him.

"Having a good time?" he asked.

"Yes, I am," she said with a tone of sorrow.

"Something wrong?"

"Nothing really," she began to say. "It's just that everyone keeps saying they're proud of me, but I just don't feel like they should be."

"Why do you say that?"

"Besides that one show where I got an Emmy nomination, I don't feel like I've made it in Hollywood," she began to say.

"Maybe you have imposter syndrome," said Connor. "You feel like you're undeserving of your success even though you should be. I went through the same thing when I became a CFO, but you'll eventually get over it."

"Never thought about it like that," she replied. "But still, I feel like I should be doing more in my career."

Connor felt compelled to say something else to help her feel better about her career.