*So, the winner of the tie breaker is Ruler Jeanne D'Arc. Seriously, she easily beat Mordred and Nobu in the comments. Anyways, let's get this chapter started.*

Ryan had to admit something: he was starting to get jealous. While he had many of female servants fighting for his attention, he had stated to notice one of them spending more time with one of his male servants. This servant was his first Ruler class servant Jeanne D'Arc. When she first appeared during the first anniversary, she was determined to keep Ryan away from her counterpart Jeanne D'Arc Alter. The two Saints of Orleans could be found fighting over the boy several times a day over who would get to spend time with him. Eventually, Jeanne confessed she had feelings for her master and the two started have a romantic relationship. While Jalter was possessive of Ryan, Ruler was ok with sharing as long as he made time for her which he did as they would go to church on Sundays and go out for a nice lunch date after.

However, things started to change when Caster Sieg arrived in Chaldea after helping the dragon boy keep the Greater Grail away from a crazed master named Darnic. It turns out that the homunculus was Jeanne's boyfriend...well at least from a different reality. Still Ryan wasn't happy when the two servants would go off and spend time together. Heck, Ruler had invited Sieg to come to church with her and Ryan last week. The brown haired boy was starting to feel that he may lose Jeanne to her past lover. Luckily, Astolfo was jealous as well as he wanted Sieg for himself. So he and Ryan came up with a plan to get their love interests back. So as the pink haired trap went to seduce Sieg, Ryan made his way to Jeanne's room.

As soon as he arrived, he knocked the Saint of Orleans's door as the door swung open to reveal Jeanne D'Arc herself who greeted him with a beautiful smile. "Oh! Good morning Master. Is there something that can I do for you? Do you need to me to get ready for battle?"

"Actually, I came to ask you if you wanted to go on a date with me today.," Ryan admitted. "I was hoping we could spend the whole day alone together."

Upon hearing this, Jeanne blushed lightly as she gave her master a soft smile while giving him a nod. "I would love to go on a date with you. Just give me a few minutes to get ready."

With that, she closed the door behind her as the brown haired boy got a text. He looked down to see he had a message from Astolfo that said: HI Hi! It's me Astolfo! Just wanted to let you know that I got Sieg preoccupied, but you and Miss Ruler need to get going because Miss Avener is looking for you! Anyways, I hope you have fun on your date because I'm having fun on mine!! Talk to you later!

"Ok. I'm ready to go.," Jeanne said as walked out of the room in casual clothes before noticing the boy looking at his phone. "What are you doing, Master?"

"Nothing. Just checking my emails.," Ryan lied as he took the holy maiden's hand in his as they began to walk towards the Rayshift room together. "Let's just enjoy our time together."

XXXXXX

After leaving Chaldea, the young couple rayshifted to Paris where Jeanne was impressed on how much had changed since she was alive. The two spent the majority of the day sight seeing as Ryan was glad Ruler could actually speak French and translate for him any time he didn't know what to say. However, he really just loved spending the day with her as he loved seeing Jeanne's beautiful smile and how kind she was to others. She truly was a Saint even if she didn't feel like she was one at times.

Currently, the couple were sitting down at a small nice and quiet cafe chatting while drinking some coffee. Ryan was had he got to spend time with Jeanne, but in the back of his mind, he wondered what exactly Astolfo was doing to Sieg in their date. Knowing the Rider class servant, it could literally be anything, but at least it gave the brown haired boy time with Ruler.

However, he wasn't expecting the holy maiden to suddenly ask, "So, Master.....I have enjoyed our time together, but I was wondering why you suddenly wanted to go on a date with me today?"

"There's no special reason. I just wanted to spend time with you.," the Master of Chaldea stated nervously.

"Really?," the holy maiden said with a raised eyebrow. "So you didn't ask me out because you're jealous of Sieg? I mean you did ask Astolfo to keep him occupied today."

The brown haired boy's jaw dropped in shock. "How long have you known?"

"I knew the entire time.," the Ruler class servant admitted. "Astolfo isn't the best person to keep secrets. He was skipping up and down the halls last night telling anyone he came across your plans."

Ryan immediately facepalm in annoyance. "Great....so why did you agree to go on a date with me today then?"

Jeanne sighed. "Really? You have to ask that? It's because I love you. Yes....I did love Sieg once, but I've been with you for past two years. I'm not just going to dump you because he's now."

"Then why have you been spending more time with him than me?," Ryan asked.

"Because you have been busy with the other girls. Also even though Sieg and I aren't dating anymore, doesn't mean he and I can't be friends.," the blonde haired girl stated. "At least you're know how I feel when you spend time with Jalter now......though I have to admit, it's nice to see you get jealous over me. It shows just how much you love me."

The brown haired boy immediately blushed a dark shade of red. "I get what you mean....I'm sorry that I didn't just talk to you about this. Is there any way I can make this up to you?"

Ruler thought for a moment before smirking at her lover. "Well....I know one way you can make it up to me."

XXXXXX

After finishing their tea, the couple immediately checked into a hotel where as soon as they enter the room, the young couple meet in a passionate kiss with their tongues wrestling for dominance. While they continued to make out, the lovers made their way to the bed. Once they got there, Jeanne D'Arc removed her skirt showing her master the white lingerie she had on underneath.

"I had a feeling this might happen....," Jeanne admitted with a blue. "So I came prepared....do you like it?"

"I love it.,," Ryan stated as he gave the girl another kiss. "However, I would love to take it off of you even more."

With that, the couple relieved each other's clothing until they had nothing left on. Ruler immediately moved in front of her lover's hardened member and gave it a kiss before taking it into her mouth. She immediately began to bob her head up and down as fast she could as swirled her tongue around her master's rod. The brown haired boy bit his lip in pleasure as he couldn't believed how skilled this holy maiden was. He soon couldn't help himself as he put his hands behind her head and began to thrust into her mouth. The blonde haired girl girl moaned in pleasure as she allowed her lover to take the reins on the loving making. It didn't take long before a thick stream of mana flowed down her throat as the Ryan collapsed onto the bed as his member came out of Jeanne's mouth with a loud pop.

"That was delicious.," the Saint of Orleans stayed with lewd smile and hearts in her eyes. "But now its time for the main course."

She immediately crawled on top of Ryan as she began to grind on his member while the two met in another passionate kiss. As soon as he was hard enough again, the Master of Chaldea lifted his first Ruler class servant slightly before slamming her down on his member. With his hands on her plump bottom cheeks, he began to thrust into the holy maiden's womanhood while Jeanne began to try to match his rhythm. The entire time they were going at it, the lovers continued to French kiss as their tongues explored each other's mouths.
At some point, they flipped over with Ruler on her back now as her master spread her legs further open to allow him to thrust even deeper into her womanhood. Jeanne felt so much pleasure that she could think straight as her eyes began to roll into the back of head.

Eventually, the two climaxed together as Ruler felt her womb being filled with a powerful surge of mana. The couple took a minute to catch their breathes before meeting once more another loving kiss.

"So...have I made it up to you yet?," Ryan asked as he breathed heavily.

"Maybe after a few more rounds.," Jeanne said with a lewd expression on her face. "I want make sure you've learned your lesson."

"As you wish.," the boy said as he went to begin another round with the holy maiden.

Suddenly, the door to their hotel room bursted open as a familiar angry Alter servant walked into the room. "Finally!!! Do you have any idea how long I've been looking for you?!"

That's when Jeanne D'Arc Alter noticed who her "boyfriend" was with. "Oh you just want to die...cheating on me with this damn holy woman while I was looking frantically for you. Time for you to be taught a lesson...move over Ruler...I'm joining you!"

I hope you all liked this particularly long chapter of Second Chances. Now as usual, let me know in the comments which girl you want to go next. The remaining girls are:
1.) Mashu
2.) Okita
3.) Mordred
4.) Artoria (Lancer)
5.) Nobu
6.) BB