Ryan had finally chosen between Emma and Claire. He picked Claire, however they had allowed each other to fuck other people as long as they didn't try to make a commitment with someone else. Although they had texted and talked a lot since he finally asked her out the previous week, this would be Ryan's first official date with Claire. In case you missed previous stories, Pinky is a nickname given by Ryan's friends for Will's crush Mia.
***
It was Saturday night, a couple days since Ryan had his role playing session with Sophia. Ryan pulled into Claire's driveway, almost across from his own driveway, preparing to pick Claire up for dinner. He walked up nervously to the door. Ryan had met Claire's parents before and they had been really nice, so Ryan wasn't worried about that aspect. He just didn't want to blow a nice evening with Claire. He had definitely become for more confident with girls after all his recent sex, but dating was still alien to him. Ryan barely had time to finish his knock before the door was pulled open by Claire's mom.
"Hi Ryan, come on in. Claire's almost ready." She said in a kind voice and Ryan relaxed. Suddenly Claire's dad came marching into the room.
"So, you think you can just take my daughter out without consulting me, listen here. I've got some rules." Claire's dad boomed at Ryan. Ryan was stunned. "I'm just messing with you." He suddenly said breaking into a smile and turning to his wife. "Did you see his face?" He asked before bending over laughing.
"Come on, don't scare him like that." Claire's mom said in a concerning tone, but Ryan could easily see her suppressing a laugh.
"Are you two finished." A voice asked behind them. Ryan turned to see an absolutely stunning Claire. Clad in a black dress that hugged her body tightly and reflected a little light giving it a deep space kind of feel. The Dress ran to a few inches above her knee. She had her black hair free around her neck versus her normal ponytail. She had heels on, 1.5 inches Ryan guessed. Overall, Ryan had never seen anyone this beautiful before. Not even Emma or Sophia. Ryan was at a loss for words.
"You two have fun." Claire's mom called out after them as they walked to the car. Before getting in, Ryan turned to Claire.
"Claire, you look amazing." He said, glad he had dressed up for the occasion in the same suit from homecoming except this time with the blazer.
"Not so bad yourself." Claire stated, eyeing Ryan up and down once before stepping into the passenger seat as Ryan held open the door. Ryan got in and they drove off. Ryan had picked one of the fancier places in their area, but it wasn't so ornate that it would be overwhelming. Ryan had struggled with a place to go because most places were closed in the winter and besides a movie or dinner he couldn't think of anything. Lucky he had gone to this restaurant a few days ago and felt it would be perfect for a date. He hadn't told Claire were they were going yet, only that it was for dinner and wasn't casual.
"So, where are we going?" Claire asked impatiently as they drove.
"You'll see." Ryan said exited.
"I hate waiting, please tell me." Claire begged.
"Nope." Ryan stated firmly.
"Fine." Claire huffed. When they finally arrived at the restaurant, Ryan got out and opened Claire's door for her.
"Madam." Ryan joked, holding his free hand out for her to grab as she got out. Claire giggled but went along with it, stepping out of the car gracefully and even doing a mock curtsy. They walked into the restaurant and were led to their table.
It turned out Ryan had nothing to worry about. He found it so easy to talk to Claire about anything and had a great night. They split a lava cake for desert, then after Ryan paid the check they walked out to Ryan's car. They drove home, still talking. It seemed they would never run out of topics of conversation. When at last they reached home Claire let herself out of
the car this time and walked over to Ryan.
"I had an amazing time tonight. Thank you." Claire said kissing Ryan. Despite having been naked, in a threeway, and grinded with her the kiss made him blush.
"You're so great." Ryan said looking Claire right in the eyes. This time it was her turn to blush. They kissed again and then Ryan walked Claire to her front door. Claire opened it and thanked Ryan one last time for an "amazing evening" before running inside to tell her mom how it went. "Mom, it was even better than..." was all Ryan could catch before the door closed. Happily he drove across the street and walked in the house, ready to face his own parents questions about how the date went.
***
Ryan's phone buzzed. He had been trying to get to sleep but was still thinking about Claire. He looked at the lit up screen, covering his eyes slightly from its brightness. To his surprise, it was Will texting him, not Luke.
- "I have a question" Will sent.
- "What's up?" Ryan responded, unsure of why he was even bothering to respond at 12:30 on a school night.
- "I was thinking of asking out Mia" Will texted, causing Ryan to immediately sit up in bed, his full attention on their conversation.
- "Mia as in Pinky?" Ryan sent, still startled. Will had been crushing on Mia for almost three years, at least that's what Luke and Andrew had said and Will had never denied it. Why was he suddenly making the jump now.
- "No, as in Khalifa. Come on Ryan" Will texted back, obviously annoyed.
- "Ok, Ok" Ryan sent.
- "Anyway, how should I go about doing it? What should I ask her to go? I know you recently asked out Claire so I was wondering if you could help" Will sent.
- "Well, me and Claire had sex before I asked her out, so it might be a little different. Unless there's something you want to tell me?" Ryan texted jokingly.
- "Come on Ryan, I'm serious" Will replied quickly.
- "Well, as I said, it was a bit different for me. But I know Luke asked Abby to a movie so you could try that" Ryan suggested.
- "Wait, Luke asked out Abby?" Will sent. Ryan suddenly realized there was a good chance Luke had only told Ryan about that.
- "Yes, but back to you" Ryan sent trying to change the conversation. "Does a movie work?"
