It had been a year since Alex and Rias started dating. In that time her curiosity of him had only grown, but she was unable to figure out anything about him. What Rias didn't realize was that the more time she spent with Alex, the less she wanted to make him her servant, and the more she started actually caring about him. To everyone else, she was Rias GREMORY, not Rias the girl. Alex didn't treat her like that, so she started to genuinely care about him, to the point that after a few months together she gave him her first kiss. She was worried though, as she would have to deal with her engagement sooner or later and break off this relationship.
Alex however was well aware of the situations that were concerning her. He could tell that though Rias started to care about him, she wasn't completely open to him. The reason being that she still didn't act like she did in the series once she developed her feelings for issei, she still had her air of composure. He had also gotten a bit closer to Akeno, and when their second year started, Kiba. They all still tried to keep their identities from him though, as even though he was Rias's boyfriend, he was still "human".
Alex's attention was taken by something else though, as he once again met issei. It appeared that issei had completely forgotten about how Alex could use ki, and stopped training like how Alex told him to. As he already decided, Alex was going to leave him alone since he didn't take the branch he offered to this world, but apparently issei had other plans.
"Um Alex, those three are causing trouble again. Could you please help us?" The young girl asked him. She was a member of the kendo club, the frequent victims of the perverted trios peeping. Alex only shook his head, and went to follow the girl to the kendo club. The girls knew that issei and the other two were waiting for them, and so they waited outside the changing room for Alex to show up. After the incident that led to him dating Rias, Alex had become the go to guy for when someone was bugging you.
The kendo club in particular, as they were the ones who almost suffered the most during that incident. Alex had also developed a closer relationship with the club, from occasionally going to learn swordsmanship. It was a far cry from actual battle techniques, but it was as good a starting point as he could find. He had quickly picked up the concept though, and within a week there wasn't anyone in the club that could match him, only raising their opinion of him higher.
As he approached the building, he could see the three of them fighting over the hole. Alex once again shook his head, and cleared his throat. Hearing him, the three slowing turned their heads and saw him standing there. They were about to run when he said,
"As of this moment I'm talking to you, if you run then I'm going straight to punching." The three quickly kneeled in front of him. He looked at the three of them, each were calculating the best way to get out of this mess.
"Day after day, why? If you guys acted civilized then there would be girls willing to be with you, you know? Instead you creep them out and push them away, then you cry into the air about how you all want girlfriends." Almost everyone in the school had been able to hear them crying out about the "injustice", yet as far as he could tell none of them actually tried to do anything about the situation.
The three then did the usual, they talked about how he wouldn't understand them, and about how they will never try to hide their true desires. As they continued their speeches, the kendo club girls just became more disgusted with the three of them. However, issei added a new part in his that was his last mistake.
"-and I will get to fondle those great tits of Rias Gremory!" Alex's eyebrow twitched at his words, while the kendo club went silent even the other two started becoming scared. It took a moment, but issei seemed to realize his blunder. Alex however, had a giant smile on his face that didn't seem to have any bad intent whatsoever. He very discreetly used his Devils charm on the three.
"You know, I think I've been too hard on you three. How about this, I'll look up a few girls I know about, and I'll introduce you. If I'm lucky then each of you might even get two girls each!" They each became excited as Alex's words, and didn't doubt him at all due to his charm. He then arranged with them a place to meet the girls later, and walked away to go find them. He knew that the person he wanted should be in this area, but he would have to try to find them.
It took him a while, but using magic he managed to find the person he wanted, and she agreed to meet the men he wanted to introduce her to. She had even agreed to call five of her friends to meet with them. He brought them to the place he arranged with issei, a karaoke lounge/hotel. They booked three rooms for each of the men they were going to meet, and Alex told them to go ahead and wait in the lounge for them to arrive.
"And remember, they are very shy when they're actually in front of a girl, so you might have to be a little forceful. I'll send them in when they get here, and you enjoy yourselves with them tonight." A few minutes later the perverted trio arrived.
"Alex, thank you for setting this up for us!" Issei said. Alex couldn't help but think 'you were declaring you wanted to fondle my girlfriends tits earlier, and now you've completely forgotten about it?' But he didn't say anything and simply said,
"It's alright, you know I might not have been to understanding, having a girlfriend and all. Hahahahahahaha. So there are six maidens waiting in this room for you three, and they are very eager to meet all of you. Issei, make sure you ask for Mil-tan. She seemed very interested in you when I told them about you." Issei and the others seemed very excited, until Alex opened the door.
"ARE THESE OUR DATES TONIGHT?!" A very deep voice sounded from the open door. The looks of excitement on the perverted trio turned to horror instantly. Alex swiftly stood behind them so none would be able to escape, and said,
"Yes they are, remember I said they'd be shy, i mean look they're all speechless. Now enjoy yourselves tonight." After finishing his words Alex pushed the three horrified boys into the room, and walked away. 'I try to help you get a harem, I try to help you live out your fantasy, and you declare you want to molest my girlfriend right in front of me?' Alex didn't fell even a shred of guilt at his actions.
A few days later he convinced himself he was imagining it when he saw the three walking awkwardly in the school, and when they started massaging their butts. Unsurprisingly, there weren't any more harassment issues after that.