That is the true fuck up part, should have dumped em and called it a day rather than awkwardly going through them like that.

Communication is key in a healthy relationship. He done fucked up, but he came clean about it. Fucked up after coming clean too, but thats a separate issue. He breached trust and opted to take the L rather than add to it.

Every hear of the fappening? Or any celeb icloud hack? His password gets snagged in a phishing incident or a data breach on another site puts anything backed up to the cloud at risk. Technically more secure on the device, because of outside of it being stolen, he can directly restrict access, although as long as it has internet access it too is vulnerable, people just don't consider that aspect.

Plus it takes a certain level of trust in sending nudes, simply because you have to have complete trust that they won't send em to buddies, putting them on the internet, or if a bad split sending them to friends and family.

Sounds like you need a lesson in internet security and empathy. She isn't making him feel bad out of malicious intent, she is coping with significant insecurities being triggered, and is justified, because even if the risks are microscopic, they aren't 0.

Yeah, kinda shot yourself in one foot trying to act big because it's a negative stigma to be a virgin, then shot the other foot by trying to salvage an "alpha" image, not to mention your face shot, which probably could have been salvaged with good humor if you hadn't tried to act more experienced than you are.

You could try to talk to her about it, which goes one of three ways, depending on her. Either you add fuel to the laughingstock fire, get ghosted or goes nowhere, or finally honesty might buy you some goodwill and as long as you don't keep trying the alpha nonsense, might even get another shot.

Ha!

Very true, only silver lining there is big bro is weeding out the ones who are easily disloyal, but damn that's not healthy to their relationship, cause even if OP pulls someone who won't give his brother the time of day, that seed of paranoia is already well rooted.

Reminds me of when my buddy and his wife were at the hospital having a baby and they asked me to take their daughter to cross country practice. No big deal, dropped her off, hit up the local Walmart for breakfast and went back to wait, not thinking that this practice was at a local park until I got the dirtiest look from a lady walking past my car with her small child right when I cracked open a Monster. Thats when I realized I was an unshaven (murder hobo is the best description) man alone at a park cracking open a cold one with a bunch of little kids and high schoolers running around. Not exactly a good look, and ended up messaging a coworker going if I go radio silent the cops are probably talking to me lol