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Best Summer In HS
Male - 34, fair warning, this confession has a sad ending.
When I was in HS I wasn't a jock or super popular but I was apparently good looking enough to have my pick of plenty of cute girls. I had several girlfriends over those four years and even more fuck buddies and all of them were really attractive, some of them were even amongst the popular girls at school. Honestly though, the most attractive girl during my teenage years was my little sister's best friend Lilly. She was very shy but the only reason I hadn't pursued her was because of my sister and I didn't want to make things awkward.
Lilly was a skinny girl but was really beautiful and friendly and I later found out she had really nice, ample tits despite her skinny figure.
The summer of my 18th year my sister let slip that Lilly had had a huge crush on me for years. They were both 16 that year but decided to talk to Lilly about it anyway and she admitted it was true and then I told her I'd been attracted to her for a long time. That peaked her interest and we started hanging out more and discovered there was a spark between us and things started getting physical pretty early on and then one afternoon she let me pop her cherry.
Lilly and I fucked a lot after that for the rest of the summer. I used condoms as I normally had with most girls before that but Lilly wasn't on birth control. One time we were going at it pretty passionately and the condom broke but we didn't notice until I withdrew later and my cum was leaking out of it. We got scared but didn't know what to do without our relationship coming out and she was technically a minor. She ended up getting pregnant.
Lilly refused to tell anyone I was the father despite her parents grilling her about it repeatedly. My sister also kept her mouth shut. Lilly's parents wanted her to get an abortion but she refused because she didn't feel it was right to kill the baby. I had suggested she could put the baby up for adoption after it was born and she thought that was a good plan. I felt really powerless to help her openly because people would've gotten suspicious but I gave her every cent of what little money I made at the time incase she decided to keep it. If she did keep it I was going to come out as the father and support her openly but she told me not to because of the legal implications.
Sadly things never got that far. Despite her having a really smooth pregnancy something went horribly wrong during the birthing and she and the baby both died.
I was totally devastated. I blamed myself so hard that I was going to fess up because I wanted to be punished. My sister actually talked me out of it though, saying it wouldn't help anything and Lilly wouldn't have wanted that. That didn't stop me from beating myself up for years after that. I'm married with kids now and to this day only me, my sister and my wife know the truth.
I'll never forget Lilly and I still blame myself at times but I just try to stay focused on my wife and kids that I have now.
BWAHAHAHAHA!!
Funniest damn story ever! Turns out Lily was a fucking whore behind your back!
Turns out she had a set of black twins but didn’t want you to find out so her rich dad paid a large sum of money to have Lily shipped off to a different state and put the babies up for adoption.
I remember reading that story and laughing my ass off!
The hell are you talking about?
Wow. That's tough, but it's definitely not your doing that led to that. You both did what young people do and even if you had fessed up, it wouldn't have changed the outcome. Not sure if it helps or will mean anything, but they say we plan our lives out before birth, so all of this was just a part of a cosmic plan that your soul and her soul mapped out... Almost as if life is really a stage play. But on another note, you might have material for a good book or script on your hands.
Thanks. It's also really tough because I know Lilly's brother and I still see her parents from time to time and they have no clue what really happened. It's hard not really being able to talk about it openly plus the constant wonder of what could've been if she and the baby had lived. I honestly think Lilly loved me.
Just remember her for the positive memories and be grateful for the gift of having her in your life for that moment. You'll see her again on the other side and it'll all be okay.