Me (26m) and my gf(26f), Which we can call O, are getting married this May after About 8 years of dating. We started late senior year of highschool but I started to have feelings for her sophomore year. We had classes together often and I would try my best to get the courage to ask her out but I had low self confidence. Well one day junior year in class I noticed my friend Jay and Olivia talking and getting along very well. I noticed that Jay kept reaching around O's chair grabbing her ass and she would giggle but not ask him to stop. I was instantly jealous because Jay knew I liked her and he was a player that already Could have any girl he wanted. At lunch I talked to Jay about their relationship and if he could back off. He initially looked like he felt bad but soon into the conversation he tried to turn it into a positive. He said that he flirted with her and learned what she liked it would help me. That if he put in the hard work of knowing what she liked and didn't I would have a leg up when I asked her out. He sounded convincing and he promised that it would only be casual and not a serious relationship so I agreed to let them continue.

     The biggest mistake I ever made. A week after agreeing to allow Jay to flirt with O I saw them making out in the school parking lot. My heart sank I was mad he had gone beyond flirting but calmed because it was only a kiss. I also felt bad about how turned on it made me ( start of my cuck kink). Later that Friday while at home Jay sent me a message with some pictures attached. The message read "Dude you'll love these". Attached were pictures of O naked posing in front of a mirror. I was devastated. She look so hot but was posing for one of my best friends and I couldn't believe. I told myself that when i say Jay next I would tell him to cut it out before things escalated. I was too nervous to do it over the phone and I was also too busy masturbating to the photos all weekend to think clearly he sent. Well that Monday before class I met Jay to talk about O but before I could say a thing Jay blurted out "sorry dude I think I went too far". Internally i was thinking it was the nudes he sent me but then looking me dead in the eyes he said he fucked her. My heart stopped and I couldn't even process what he had said. O had mentioned to us before she was a virgin and was waiting for the right guy and my friend took it from me. I had dreamed about being the one to taking it from her and Jay new this. But instead of being angry I was just turned on by the idea of her being fucked. And instead of asking him to back off I tell him that it's okay as long as he backs off if I ask her out. After this he seemed confused at first but I think he understood.

For the next 7 months Jay would send me her nudes and tell me stories of them hooking up. This lasted until prom and I finally asked out O and he got a serious GF. For the first couple years of me and I relationship I returned his favor by sending nudes. I haven't seen Jay in 5 years but I do send him O's nudes occasionally for being my first bull