Author's Notes: Probably my darkest fanfic I've ever written and there's no death characters here. This is also the one I had a lot of revisions. I'm a die-hard GinTae shipper and writing this is very experimental to me. There would be explicit stuff but it doesn't involve GinTae but don't worry it will be a happy ending. If you're not comfortable reading some parts, you can skip those or go straight ahead on Chapter 3. But still, I would like all of you to read the whole thing. Chapter two is where the main story happens. (Please forgive me for writing Otae in this version. I know she's strong but I want to explore her vulnerable side.)

"I think he's following you." A sunglasses-wearing madao was seen hanging out with the number one hostess of Kabukicho.

"What do you mean? I'm not seeing him here".

"That's not what I meant. He's trying to date for real also."

"Oh, why now?" Otae was shocked to hear the news. She knew Gintoki is the type of a guy who doesn't want to settle with anyone. So to hear that news was a shocker to her.

"I think he feel pressured seeing you dating someone else." Madao said. Apparently, Otae is dating Kondo for a year now. She also felt pressured when everyone at Snack Smile were getting into relationships. No one ever dared to court her except the gorilla. She saw him changed for the better so she thought she will give him a chance and the rest is history. Despite of his stalking past, he never took advantage of her that they are now together plus he's cooking her delicious meals. He doesn't even hide in her closet anymore and he enters now thru the front door. Shinpachi was surprised at first but he took it lightly. So far, she's happy with him.

"So, who's the unlucky girl?"

"Is that jealousy?"

"I'm dating someone already, Hasegawa-san. I don't want you to attach me to that lazy samurai." She gulped another drink. Madao just stared at her, smirking.

"One month after you started dating, he tried to date Sa-chan." Otae was bewildered. Gintoki dating Sa-chan?! She doesn't want to believe it but maybe Madao was right, Gintoki was following her.

"But as you know how Sa-chan acts, they only last a month. It was a miracle that they last that long if you ask me."

"So, is he dating someone new? I don't think any girl would want to date that NEET…"

"You forgot one. He's now dating Tsukuyo-san." Upon hearing that name, she can't control the emotions from her face. Unlike Sa-chan, Tsuki is way more decent. She's a perfect package. If she compares herself to Tsuki, Tsuki seems more compatible to that guy. She has big boobs and butt. She's also destructive when it comes to drinking. She is also on par with him when it comes to fighting. She even heard they have the same tragic story. To think that they can relate to each other in that sense, Otae felt out of place. She remembers those times she shared drinks with Gintoki on the porch. Now that they are dating other people, its quite hard to imagine that they will share another drink like that. 'What am I thinking? We're just friends'

"Are you okay Otae-san?" Madao's question distracted her thoughts.

"Yeah. I'm fine." She took another drink.

Soon, she finished her work. As she walked along the street of Kabukicho, a familiar tall guy was approaching the other way. "Where's your gorilla boyfriend?"

"Is that the proper way to greet someone you know? I just want to remind you, he is an amazing boyfriend. He's just busy at work. He has a job, a fact that you're not familiar with."

The man, Sakata Gintoki, smirked at her being smart mouthed. "I have work you know. It just so happens that work is in Yoshiwara. If he's really a nice boyfriend, he should give you some bodyguards to ensure your safety."

"He knows that I'm a strong woman, Gin-san. He knows me well."

"Of course, he knows you well. He's your stalker."

"He changed Gin-san. And unlike you, he's pampering me like a princess. He's a great cook and he doesn't even insult me especially with my chest."

"It's very obvious he's making you fat. You gain some chest-" His talk got short when he was thrown into the ground.

"Don't start with me with that talk. I've heard you dated Sa-chan".

"Yeah. She has big butt and boobs. Plus, she can cook." The truth is, he felt something weird when he heard the news that this girl started dating her fellow gorilla. Some people around him began teasing him and encouraged him to date as well. As usual, Sarutobi presented herself so he took the chance. At first, he was shocked that Sarutobi can be a decent girlfriend. She suddenly acts tsundere, which he's not used to seeing her. He regrets asking her why she acts like that because all of a sudden, she unleashed her Masochist side. Sa-chan was waiting for him to give him a signal. That same day, he broke up with her.

"But I heard you have another girlfriend?"

"Are you jealous? Why did you become interested when it comes to my love life?"

"I just felt sad for those women who will get involved with you..."

"Just to let you know, Tsukuyo is a nice girlfriend." She is also a decent girlfriend. She gives him foods as well. As long as she avoids alcohol as she promised, they are good. So far, the relationship is going well.

Upon hearing those words, she felt a prick inside her. "Why we have this conversation in the first place anyway?" She turned around but before she walked away, she said, "Gin-san…are you happy with her?"

Her question made him wonder, "I think so…In fact, I'm going there and spend the Valentine's Day there tomorrow."

'So they already have that kind of relationship', she thought. 'Well, that's Yoshiwara for you'. Without facing him she said, "I'm glad you finally met someone Gin-san." Something from that sentence made him anxious. "How about you? Are you happy dating a gorilla?"

Before she can answer this question confidently but now that he's the one asking her, she felt something stuck in her throat, "Yes, I am. And stop calling him that please."

"I'm glad that you're happy with that stalker."

"He's not a stalker anymore Gin-san."

"If you say so, still be careful. He still has some pervert side."

"Don't talk like that! You're pervert as well." He looked at her as she finally walked off.

Next day is Valentines' Day and Kabukicho was busy. Another well-known red-light district named Yoshiwara is having the same experience. Most of them were men who are single. Some wants to experiment and getting into extra marital affairs and some were heartbroken who seeks comfort. And none of those applied to Gintoki.

Hinowa demanded him to stay for the night before. A day with Tsukuyo yesterday went well. Just a typical date like a normal couple would do. He might be a pervert like Otae declared but he's gentleman when it comes to the women he knows. So far, Tsukuyo is way more tsundere than Kyubei. They're dating for over 6 months now and yet, nothing happens between them physically. One time, he simply tried to drape his arm over her shoulder and he was given a German Supplex instead. What's more if he tries to hold her hand.

Tonight, he was escorted by a courtesan. He has enough drink for tonight that he let her pushed him until they reached a room. Just then the lady closed the door, leaving Gintoki behind. He found himself alone in this violet-lighted room with none other than…

"What's going on?" He's drunk but he is still aware of his surroundings. In front of his eyes is none other than Tsukuyo, wearing some makeup and a kimono that a high-end courtesan usually wears. He knows she's pretty but that night she is way more beautiful. He just wonders he doesn't feel anything at all. He's supposed to be the boyfriend. Well, he doesn't have any romantic relationship prior to this if he doesn't count the one with Sa-chan so he doesn't know how to really act.

Tsukuyo stood up and approached him. "Are you drunk?" He asked. He doesn't want to encounter her signature fighting style at the moment.

"No worries I'm not drunk."

"Are you using love potion to me?"

"Why should I use love potion when I already got you?" Suddenly, she grabbed his collar and kissed him. He felt anxious. He has some experience with courtesans and prostitutes before but right before him is his close friend. His girlfriend. And he felt this is not the right place and time to do it. He could feel she was nervous kissing him. He stopped her and saw her getting teary eyed. He's not used to seeing her like this. "Are you sure about this? Did someone force you to do this?"

"No. I want to do this. This special day with someone I love." She kissed him passionately this time. She was happy that she's now in a relationship with the Hero of Yoshiwara. She was feeling high the day he asked her on a date because she thought her love is one-sided. But her being shy doesn't help with their dates. She wants those physical touch that she saw with everyone in Yoshiwara. Tsukuyo was encouraged by Hinowa and others when she asked them for some advice. She decided to give herself to him tonight.

'If you say so', he thought. They kissed back and forth until she pushed him down on the futon. He wants to take a breather but Tsuki won't stop kissing him as she straddles him. She took his hand and he felt something squishy. He opened his eyes and saw that his hand was on her breast. He was flabbergasted. He was too focused on the kissing that he failed to noticed she stripped her kimono, leaving her completely bare. It's been a while since he saw a naked woman. He knew this is her first time.

"What's wrong Gintoki? First time to see a woman like this?"

"No…just I'm not used to seeing you like this."

"You should from now on."

"You really want to do this?"

"Yes…"

"If that's what you really want…" He switched their position and he discarded his upper clothing. Tsukuyo can't stop her heart from beating so fast. She cannot believe Gintoki was here, getting ready to be intimate with her. Gintoki on the other hand, even though she looks ethereal underneath him, he felt something was off. 'No…it's been a while since I did this. It will be over' he thought. Tsukuyo quickly locked her arms around his neck, losing his balance and she started making out with him. The kiss went deeper but Tsuki noticed that Gintoki never made a move. She noticed he suddenly stopped moving his hand. His one hand was just on top of her breast, motionless. He did not even try to kiss the other parts of her body. She learned that at this point men get hard but Gintoki was not. She expected way too much. She should not listen to them in the first place. She was even encouraged to use Love potion but she refused.

She stopped their kiss, "What's wrong Gintoki?"

"What do you mean?"

"You're not making a move. Don't tell me you are a virgin?!"

"I'm not. I have experience with a lot of women."

"I'm going to be frank. Are you not excited? I'm ready to show the real me, my soul. Don't tell me those stories of you having ED (erectile dysfunction) is true?"

"No, I'm not". That was a lie that spread around Kabuki and Yoshiwara. No one knows who started it.

"Well then show me." He can't believe this is Tsukuyo he's dating. He knows that later in their relationship it would get to this point but he was just stupefied at this moment. He decided to make a move on her so they could just finish this over. He felt uncomfortable when he tried to move his hands around her breast. He was supposed to enjoy this opportunity to touch her without getting beaten up but he felt hesitant. When she tried to get rid off his pants, he stopped her. He took her hands off from him and he sat up far away from her.

Tsukuyo felt ashamed. She was left there naked laying on the futon. For the first time, she felt she's like one of those courtesans and not as his girlfriend. She took up the courage and hugged his back.

"I'm sorry Tsukuyo."

"I'm sorry if I was being aggressive. It doesn't look good on me, isn't it?"

"It's not". Just then, he covered her with her discarded kimono. He dressed himself as well. "I'm sorry I ruined our first Valentines Day".

"No, you did not." She turned into a tsundere again, "But I really want to give myself to you…"

He just ruffled her hair and walked away, not able to respond back. Back in the room, Tsukuyo shed some tears.

For the first time in his life, he doesn't know what he really wants. Somehow, some men were jealous at him, having a hot girlfriend. He was supposed to feel lucky. He was already there in that room with Tsukuyo and he can't deny he feels flattered knowing that she wants to give her body and soul to him but he really felt something was off. Someone was hindering him in doing it. He was too distracted thinking of these things when he failed to notice that his feet automatically dragged him to a familiar place. A house of that certain someone.

"Gin-san…" He was frozen when she saw Otae crying outside their dojo. Then, she ran towards him and hugged him tightly. "Gin-san, please. Take me away. Take me anywhere, please." His chest was getting wet from her tears. A lot of questions running through his mind and yet he did not dare to ask her. He held her hand and took her away.