TIFU by sending my girlfriends mom a picture of my dick.

Long one here, feel free to skip to the bottom. After reading a story on this sub I was reminded of something from my past that I think is now laughable. It wasn’t then. In high school, my brother passed. This happened at the beginning of the school year, and the fucks quickly went out the window. I skipped class, school, faked doctor’s notes, etc. One day this girl was staring at me, and despite being a gorgeous girl, my brain decided that “what the fuck are you looking at” was the appropriate response. And due to my state of mind at the time, I didn’t much care. A week later, she comes up to my locker and hands me a picture of two eyes delicately drawn in absurd detail. She said “I just wanted you to know you have beautiful eyes and I can tell there’s something special behind them”. Huh. Last week I told you to fuck off. This week you made me smile for the first time since my little brother died. I asked to take her on a date, and boy did I have no idea what I was getting myself into. Her parents were STRICT. Long story short, after MONTHS of really committing to taking things slow, spending time with her family and pretty much only getting to be with her at school or once I was finally allowed to drive her home (they’d time us). Our “dates” were her family dinners. One day, I go over early as always, and dad gives me the go ahead to take her on a date. I was blown away. The following months were bliss. I was genuinely happy for the first time in a long time. Her and I had been together for a year and everything was going great. Her family loved me, but also thought their daughter was the most innocent thing on God’s green earth. Well, after a year of being together at that age, you get a little freaky. Especially since she’d never really been allowed out and I was her first real boyfriend. One day, as any other, she left school early for a tennis match. By some act of god, her car battery died and her mom had to pick her up. Coincidentally, she dropped her phone and while she was at her match her mom went to Apple to get it fixed. Well, I knew she was at the match, and knew it was past time. It had been hours and I hadn’t heard from her. We had a date planned for that night and I was pretty eager to get out if you catch my drift as we’d been teasing each other between classes. So I sent a few playful texts. No response? Huh. When she lost a tournament she’d go into a SERIOUS funk. And a combo of fruit baskets and being sexually comical could always cheer her up. So. The texts got progressively more provocative. I won’t get into detail, but I pretty much sent the most pornographic shit you could imagine, handcuffs that we kept in my car, what we’d be doing that night, and finally with no responses, but them being read, I called in my last line of defense. A dick pic with her name written on it and a smiley face(we were some serious weirdos), and said we’d be eating sushi off of each other on my families sailboat for dinner. This was the check mate of, stop pouting and let me come cheer you up. HOURS go by and now I’m seriously worried. I called her mom. No answer. I then get a phone call from her dad telling me to meet him at the garage of their second residence by the beach. Oh boy. We were legal in our state so I wasn’t worried about that, but I didn’t know what he did for a living other than I know he traveled to Venezuela and Mexico weekly and was only present on weekends. Turns out, she gave her mom her password so Apple could fix the phone. And she was reading everything I sent. Saw the dick pic and all. Her father told me he best never see me near his daughter or their house again if I was to be acting in my best interest. I told him, with all due respect, your daughter is my life, and that won’t happen, you can have the time you need to understand that, I’m not going anywhere. I guess part of the issue was they scrolled through and read our earlier messages and thought I was turning their innocent daughter into a sexual deviant. But it was mutual and I always let her lead the way. I explained this, and he decided their family would be spending the entire summer traveling and got her a new phone with my number blocked. For 4 months we’d maybe speak 15 minutes a week. If that. No contact. They gave her a flip phone with no camera. Finally, school started again, and her dad had taken her car and dropped her off the first day. I went up to him, shook his hand, and said let’s grab dinner and discuss this, still here, not going anywhere. He had respect for that. A year from there we were back to normal. It was referred to as “the incident”.

TL;DR my girlfriends phone broke and without me knowing, her mom took it to get it fixed. She wasn’t responding, so I sent a dick pic and talked about how we’d eat sushi off of each other on my boat for date night. Date night didn’t happen.