***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."
