High School Reunion

"Let me ask you something, do you enjoy what you do?" he asked.

"Of course, I do," she replied.

"Do you look forward to it every day?"

"Yes."

"And are you consistently working? No long breaks between jobs."

"Yes, I have a lot of work and plenty coming up over the next couple of years," she said with a gleeful smile. "What's your point?"

"What I'm saying is that maybe that's all that matters. Some people hate the jobs that they have to go to every day, and they are miserable because of it. If you love what you do and have fun doing it, then that's all that matters."

"I guess that's true," she said, feeling a little better.

"And for what it's worth, you've done much better than most people have when they run off to Hollywood. Some of them are lucky enough to get jobs as extras in a movie, but you've made it far enough to always be working and enjoying the work you do. Even if you're not doing Oscar-worthy films, you still made it."

Ruby was very happy after hearing all of that.

"You're right, what the hell am I complaining about?" she began to say. "I'm doing great, so I should be happy about it."

"That's right."

"So, what if I'm not winning big awards. If it was that easy, then every actor would be getting them."

"Precisely."

"Thanks, Connor," she said giving him a big smile. "I'm so glad I had this talk with you."

"I'm glad to help."

One of her favorite songs began to play, and Ruby insisted that they go back on the dance floor. Connor's feet were still a little sore, but he did it anyway to make her happy.

They danced for a little while before they sat down with some of their old friends to hang out and talk about their lives. They occasionally went back to the dance floor again, but mostly everyone just hung out with each other. People kept asking Ruby questions about her movie career and the celebrities she met or dated. Whenever it looked like she was getting a little flustered by the questioning, Connor stepped in to change the subject, which Ruby appreciated.

Sometime after midnight, the reunion began to die down and the guests began to leave little by little. At one point, the front of the hotel was lined up with taxis and Uber cars waiting to take people home. Those who already had a room reserved at that hotel stayed at the reunion longer since they could just take an elevator.

By 1am, nearly everyone was gone. Those who remained joked about who was leaving with whom for a reunion hook up. There were plenty of signs that some of them were indeed going to hook up. Sarah tried to stick around a little longer, but she had to go home to relieve the babysitter. Before she left, she said her goodbyes to the few that remained, including Connor and Ruby.

"Ruby is looking a little tipsy. Make sure she gets back to her hotel room "OK," Sarah told Connor.

"I'll make sure she's alright," he replied.

Sarah gave Connor a wink before she walked away, insinuating to him that something could happen between him and Ruby. He wondered if at any point in the last decade, Ruby had told Sarah about the incident between them after graduation; Sarah never signaled it in any way, but she may have been good at keeping secrets.

"Do you mind walking me back to my room?" Ruby asked Connor.

"Sure."

In the beginning, Connor thought he was just escorting an old friend back to her place. By the time he got to the elevator, he started to consider whether this was going to be one of those reunion hook-ups. He decided to just hold off and see what would happen when they got to her room; the last thing he needed to do was to misread any signals that weren't there and make a fool of himself with her again.

Either way, that was not going to be his focus. If he was going to be alone with her, he hoped he could finally apologize to her for what happened between them all those years ago. Even if she had forgotten about it or simply let it go, he felt it still needed to be said in case there were any old grudges between them.

"You want to have a nightcap with me on the balcony?" she asked.

"That sounds like a lot of fun."

They got to the top floor of the hotel, where the penthouse suites were. Connor had never seen one of those rooms in person and was curious if it was like in the movies, and sure enough it was. It was basically like a small apartment, compressed to the size needed for the hotel. There was a large sitting area for the big screen TV, a decent sized bar by the entrance to the balcony, a small dining area, a kitchen, and unlike most hotel rooms where the bed is in the same area as everything else, it was in a separate room from the rest of the suite.

"You must be doing very well for yourself," said Connor, in awe of what he was seeing.

"I know it's a bit much for one person, but I've been enjoying the fruits of my labor," she replied. "But this is still just the third biggest penthouse suite they have here. The others were far too extravagant for me."

"At least you recognized that would be too much. I know rich people who would waste more money on that kind of stuff."

"Would you like a drink with me on the balcony?" Ruby asked.

"Definitely."

Ruby made them both cocktails from the bar, and they took them out to the balcony, which was basically like a little deck. There was a large glass table in the middle with several chairs, and they sat next to each other as they looked out at the night sky and the city.

"Amazing view," said Connor.

"Do you mean me or the city?" she asked.

"Both."

She smiled when he said that.

"Did you really see every movie or TV show I've done?" she asked.

"Every single thing, including the commercials."

"What did you like best?"

Connor thought for a moment and decided to have a little fun with her.

"College Party Mayhem," he told her.

Ruby laughed really hard at that. Connor was only joking because that was the straight-to-video college party movie where she did that striptease and got fully naked.

"I'm sure there was a big reason for that," she said.

"I was just joking, but it was a funny movie, and I saw it a few times."

"And how many times did you watch my striptease?" She said, smiling.

"You don't want to know that answer," he told her.

They both had a good laugh at that.

"A lot of famous actors had to do a lot of crazy stuff before they got big, and that was mine."

"Now you're a star," said Connor.

They clinked their cocktail glasses together as a toast. They then sat there for a while, enjoying the view and having casual chit-chat. After a while, they had nothing else to talk about and sat in silence for an awkward amount of time.

"I remember the last time we were on some kind of balcony together was back at the lake house party for our graduation."

"Yes, I remember."

Connor didn't want to kill the mood between them, but he needed to talk to her about that night. He felt there was no other time to do it besides now.

"Listen, Ruby, I was hoping to talk to you about that night," he began to say. "In particular, about... well..."

"Let me stop you right there," Ruby interrupted. "There's something I've been wanting to say for a long time now, and I need to do it now before I lose my nerve."

"What do you want to say?"

Connor saw how nervous she was, much like he was at that moment. He wanted to apologize to her, but she wanted to talk first. He considered that she was going to say how disappointed she was in him that night or say that there was no need for an apology from him. A number of scenarios were running through his mind, and the longer she took to say something, the more scenarios he kept coming up with.

"I'm sorry about what happened that night," she finally said.

"What?" said Connor, shocked by what he had just heard.

"I said I was sorry."

Connor didn't know what to say. Out of all the scenarios he was running through his head, he didn't think it would involve her apologizing to him. He felt that he was the one that needed to apologize for everything, not her.

"What do you have to apologize for?" Connor asked.

"I was upset for a while after that night when you turned me down, but I realize now that I was coming on to you way too strong. In fact, I would say I came off pretty slutty, and that's probably what turned you off from me."

"I, um..." Connor was very much at a loss for words.

"I realize that not all guys are into that kind of thing from women, and some are even turned off by that. So, I'm sorry for acting like such a slut that night. I hope you can forgive me."

Connor saw how sad she looked after saying all of this. He couldn't believe that she thought she was the problem after all these years.

"Ruby, you got it all wrong. That's not why I didn't want to sleep with you that night."

"It wasn't?" she asked, looking very bemused.

"No, it wasn't. I mean, you did come on to me a little strong that night, but you weren't being slutty."

"I wasn't? Then what was the problem."

Connor took a big gulp of his drink and told her everything. He confessed that as much as he wanted to sleep with her that night, he got nervous because he was still a virgin back then. When he told her that part, her eyes shot open, amazed by that revelation. Connor continued to say how he was nervous about not being able to satisfy her that night because of her experiences with other guys before him and that she was going to be disappointed with how it went.

Ruby asked about how a few of his ex-girlfriends told her and other people that they did have sex and how good Connor was in bed. He had to tell her that it was all a lie that they came up with so everyone wouldn't know that they were all still virgins at the time.

When Connor was done explaining everything, he waited for Ruby's response. She sat there for a long time in silence, contemplating what Connor had just revealed to her. All of a sudden, Ruby started bursting out laughing.

"Hey, why are you laughing?" Connor asked.

"So, you were a virgin back then?" She asked. "That was the problem."

Connor felt offended. "I don't think it's that funny. There's nothing wrong with being a virgin at 18."

"No, don't get me wrong, I'm not laughing at the fact you were a virgin back then," she assured him as she settled down from her laughter. "I'm sure most guys haven't had sex at that age, but just don't admit it like you did."

"Then why were you just laughing?"

"Because I was a virgin too," she revealed.

What?!"

Ruby explained that she never had sex with any of the guys she dated in high school, and just like Connor, she and those guys just told people they slept together to make themselves look good. A couple of them were jocks, so it was important for their reputation, and she didn't want to seem too much like a prude to her friends, especially Sarah, who by then had already had sex with a few guys.

Connor wished she hadn't included that last part about his sister; he really didn't need to know that about her. But he kept his focus mainly on Ruby's revelation.

"So, why, after all that, did you want to have sex with me?" Connor asked.

"Because I didn't want to go off to Los Angeles as some naïve virgin. I felt I should have some kind of experience like that before I moved out into the real world. I felt if I didn't, I would feel like a child trying to play grown up instead of actually being one. So, I decided to just have sex with someone, rather than be taken advantage of later on by some Hollywood douchebag."

"Did you date one of those guys when you got to L.A.?"

"No, thank God, my first boyfriend after I got there was very cool and an excellent lover when we slept together," she revealed. "The second guy I dated was a douchebag though. I wish I had never slept with him. But at least I learned my lesson with him and went after better guys after that."

"We all have that one person we regret hooking up with," said Connor.

They both agreed and had a good chuckle about that.

"So, why did you choose me that night?" Connor asked.

"I felt if I was finally going to do it, it should be someone who I like and who likes me for me and not as some piece of meat to fool around with."

"That's always good," said Connor.

"And I chose you because I always had a thing for you, and I knew you had a thing for me, and you were always so nice to me. I thought you would be the perfect guy to take my virginity."

"So that's why you wore that sexy underwear that night," Connor said, smiling from that realization. "I thought it was all random, but you were planning that all along."

"Guilty," she replied with a giggle.

They both laughed and drank some more of their cocktails.

"Either way, I still need to say how very sorry I am that night," he told her. "Sorry for ruining your plans. Sorry for being such a dumbass with you. And I'm sorry if I made you feel ashamed for trying to have sex with me."

"Thank you," she replied. "At least I know I wasn't being a slut. That's a relief."

"Until you did College Party Mayhem," said Connor.

They both had a good laugh at that comment. Ruby punched him in the arm in a fun way, and Connor pretended that it hurt him.

When they were done drinking, they went back inside the penthouse, with Ruby following him from behind.

"I guess I should get back to my place," said Connor.

"Or, you could stay a little longer and we could finish what we started all those years ago," said Ruby.

Connor was perplexed by that statement and turned around to ask her about it.

"What do you mean by... oh?" he asked, taken aback by what he was witnessing.

Ruby was standing before him, completely naked. He had seen her naked before from the nude scenes she did, but he thought her naked body was way more beautiful in person.

"Wow," he finally said. "You got undressed pretty fast."

"I've had experience, let's just leave it at that," she said.

"Did you plan this too?"

"No, just felt like the right moment for it, that's all," she said with a sexy smile.

They came at each other very fast and went straight into a passionate embrace. They kissed each other with an intensity they've never had with any other person they've been with before. They were slowly moving towards the bedroom in that embrace before Connor stopped them from going any further when he suddenly had a major concern about what they were planning to do.

Connor had to force the kissing to stop so he could speak with her.

"Listen, Ruby, just one thing--"

"Oh, please don't tell me you're going to turn me down again," she said, worryingly. "I can't go through that again."

"Oh, no, I definitely want to do this," he assured her. "I was going to say I don't have a condom with me."

"Oh good," she said, feeling very relieved. "But don't worry about it; I'm on the pill. My career is going very well right now, to slow it down with a baby."

"Wonderful."

They began kissing each other on their way to the bedroom, with Ruby helping Connor get all of his clothes off before they both fell on the mattress, completely naked in each other's arms. They spent some time just holding each other during that long, passionate kiss, letting their hands roam each other's bodies.

Connor began kissing her neck as he put one of his hands between her legs and began to play with her clit. She began to get wet instantly and was taking deep, rapid breaths.

"Oh yes, keep doing that!" she cried out.

She got really close to cumming from what he was doing to her with his hand like that. Other men have fingered her many times over, but none of them were this good.

Connor decided not to draw this out any longer; he wanted her as badly as she wanted him. He got right on top of her body, guided his dick right to the edge of her pussy, and shoved it all in. He held it there for a moment to enjoy the feeling of being inside of her. He could see from the look on Ruby's face that she also enjoyed that incredible feeling.

"That feels amazing," she whispered in his ear.

He started fucking her slowly, enjoying the moment of finally being with the woman of his dreams. Soon, he began to gradually pick up the pace and pushed into her harder and faster.

"Oh yes! Oh yes!" she cried out.

Ruby held him close to her body, letting out loud moans every time Connor pushed himself into her body. She begged him to go faster, and he complied as best he could. Her body arched up as she screamed as an orgasm surged through her body.

When Ruby got the chance, she made Connor get on his back so she could have her turn with him. She began by stroking his dick, teasing him with what was about to come next. She moved down on his body and took his dick into her mouth and began to give Connor the best blow job he ever had. Ruby didn't suck a lot of dicks over the years. Until now, she had only done so with men with whom she was in a relationship. But with those men, she developed some oral skills in order to keep the men she was with happy. She was now doing this for the man she wanted for so long and was enjoying every moment of satisfying him in this position.

When she was done sucking him off, she positioned herself on top of Connor and began riding him like a mechanical bull. He was loving every moment of watching this sexy woman have her fun with him like this. Connor reached out and gave Ruby a couple of smacks on her ass as she continued to ride him. She liked it and basically ordered him to do it again, which he was happy to oblige.

Ruby started to go faster and with greater intensity than she ever did when she fucked a guy in that position. Soon, she came to a sudden stop as she looked up at the ceiling and let out a scream as she experienced another orgasm. The scream was so loud that Connor was afraid one of the other hotel guests was going to call hotel security on them.

Connor took the opportunity to turn her over to be on top of her again. He held her tightly as he started fucking her more intensely as she screamed into his ear to fuck her harder. It wasn't long before Connor felt it was all going to be over. Ruby could easily tell from his expressions that what was going to happen soon and braced herself for it. Connor thought about pulling out before he remembered that Ruby had told him she was on the pill. With one last thrust into her body, he shot every drop of cum into her. Ruby felt the cum gushing into her pussy and loved how it felt in her like that.

When he was done, he got off of her and plopped himself beside her. After a minute of relaxing and catching their breath from that intense love-making, Ruby moved in closer to Connor and laid her head on his chest.

"Now I'm glad we didn't have sex all those years ago," said Ruby.

"Why is that?"

"We were virgins then. Our first time together would not have been this good."

They both giggled and fell asleep holding each other.

The next morning, they woke up almost at the same time. They talked a little before deciding to have sex again. Afterwards, they ordered breakfast through room service, and while they waited for it, they decided to take a shower together. Connor tried to fuck her in the shower, but she didn't want to take the risk of slipping and hurting themselves. She made up for that by letting him fuck her again when they were done, and they finished just in time for their breakfast to arrive.

They ate their breakfast out on the table on the balcony, both of them wearing hotel robes that came with the suite. They had a good time eating, enjoying the fresh morning air, and just talking with each other about anything they could think of. But soon Connor had to consider what was going to happen next between them. He was having a lot of fun with Ruby, but that fun was going to end soon when she had to go back to her life in L.A.

"I don't want to spoil the moment, but I need to talk to you about something."