Rias's nightmare has come to life. When she finally had her match with Riser and it looks like she was about to win but he managed to blindside her with a couple of his own pieces sneaking up on her. Her whole peerage did and tried their best but it wasn't enough to win the match. After that mess of a match her rules set by the match had to be met, Rias is honorable and she takes her word and promises seriously but for this situation she had to begrudgingly comply and follow the rules even though she hates it. But she still follows her moral code, she just hopes that all this especially being married to a man she doesn't love manages to get over with, she's also trying to think of a way to get out of this marriage on the spot. Especially while getting dressed into her mother's old gown, they had the same body type so her mother lent her old but almost still new wedding dress.
While getting dressed Riser came in and berated her on the match they had, they almost had no man power what so ever, she was basically out maned but also out gunned in a few areas. They also had a new pawn they were still in the middle of training. That new pawn is also the man she does love, after training and also talking with each other Rias had grown more closer to Issei. He may not know it but she does love him, she just wished that she was marrying him and not the third person talking and prideful Riser.
Riser: "I must say, Riser lives your dress, it looks so perfect for you~"
Well he was telling the truth, she did look good in the dress, but she wished that Issei was eyeing her and not this, as Koneko put it Fried Chicken in front of her.
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Rias: "Listen Riser, I just want to get this over with...."
Riser: "Oh Riser can't wait for the honeymoon already."
Riser nonchalantly walked out of the room with a vile and perverse smirk on his face, which it disgusted Rias down to the very cells that build her being. Rias right now looks at the mirror in the room and she's definitely praying for at least something to save her and get her out of this predicament, no matter the cost, even if she could sell her soul she'd do it just to get out of this wedding and back into her Issei's arms. Even if she manages to get out of this, she'll have to compete with Akeno, she saw Akeno looking at Issei before with the same look she had before.
Forward to the wedding everything went perfectly for well Riser. Rias and the Gremories even her older brother who's saddened at her loss. Riser decided to continuesly gloat about how he won the match. Rias's peerage was in the crowd and they were seething with anger not able to save their king. However Issei crashed the wedding and challenged Riser to a rematch, if he won he'd have Rias's hand in marriage, if Riser won he'd kill Issei and the wedding shall continue as planned.
Issei does intend to win for Rias's sake but... also just to finally fondle her but he didn't say it aloud. Let's just say the leader of the Fallen Angel's Azazel gave him some encouragement to pursue forward along with advice from the Dragon within his sacred gear, by literally sacrificing one of his arms for more power which he did.
Riser decided to let Issei have a rematch with him and reclaim Rias, said devil herself was hoping that he does succeed in this fight. Rias's family are watching and hoping that Issei does succeed in this bout and have a better man to be Rias's lover.
But what they all want won't happen. With the absence of one important girl is not here to add in assistance for Issei. Without her, he will fail.