20+ Confessions So Crazy They Could Only Be Shared Anonymously

11. The Tape


Well it is a complicated story but the gist of it is that I took video of my best friend’s girlfriend naked, but that isn’t even the half of it. That girl who I videotaped naked happen to be the sister of my girlfriend of three and a half years. This was years ago but it took almost two years to come out into the open. My (ex) best friend told everyone I knew what I had done. I lost all of my friends and am now alone and depressed. I was forgiven half a year later by the (ex) best friend, but this stupid choice by me has cost me so much. I’m all alone in a new city afraid my past will follow me the rest of my days.

12. Best Friend


I’ve been in a relationship with my boyfriend for over 3 years. It’s pretty serious, I suppose. Since the beginning of it, I have been devastatingly attracted to his best friend. In fact, I’ve been attracted to his best friend longer than him. And I haven’t gotten over it.

I know it’s just hormones and lust, but it hurts sometimes to know that I might have made the wrong choice and that can never be changed. Please note that I do love my boyfriend, I really do. I just can’t get over this stupid attraction to his best friend. ?

13. Virginity

Universal Pictures

I lost my virginity to my first girlfriend when I was 19. I didn’t want to have sex yet, but she was 17 and threatened to tell her dad and have me arrested for statutory if I didn’t go along.

I told my next girlfriend, when I was 24, that I was a virgin, and have been pretending that lie ever since.

14. GF’s Sister


There’s not really a whole lot to say. I’ve been fantasizing about my gf’s sister. I don’t know if it’s the taboo nature of it that turns me on or if it’s that she appears to have a great set of breasts. Sometimes, when I’m alone, I go to her facebook and jerk off to her photos, especially the bathing suit shots. We’re all going on a tropical vacation in a few months, and I’d really like to try to get the group interested in a nude beach (we’ve just joked about it so far). It’s probably a terrible idea, but I can’t help myself.

15. Serial Dater


A little over a year ago I found a site where guys bragged on the dating fortunes using CL. I tried and ever since I have become addicted to posting ads. I have dated close to 55 different woman, almost 1 per week and sometimes, two to three per week. Of the group, I had relationships with about 12, most a one time thing.

16. Toyboy

Universal Pictures

My mums friend (A milf) comes onto me in a jokey way every time she sees me, grabs and slaps my ass if I’m near or walk past her, makes sexual references about me and her even with others around, and calls me “her toyboy”

17. …is this real?


I was drunk and a homeless guy asked me for money. I offered to buy him dinner instead. We went to a nice restaurant and he ordered macaroni and cheese and a Heineken of all things. I mean, this was a 4 star restaurant and that’s all he wanted. We almost didn’t get served because of the way he was dressed. I had to give the waitress my debit card in advance.

Universal Pictures

Anyway, after my new friend I left he asked if I wanted to drink a little. I agreed because I was losing my buzz so I bought a 12 pack of beer at the liquor store for us to split. We sat and drank it. Afterwards, it was late so I said my goodbyes. He then asked me if I would give him some money.

I don’t know why but this infuriated me. After everything I’d done for him, he had the audacity to ask me this. I said “no you ungrateful piece of sh*t”. So he pushed me. I pushed him back and we skirmished in the alley for a minute till we fell together. I was on top of him and started choking him. I choked him and kept choking him until he stopped hitting me and then until he went limp. I got up and left him lying there dead in the alley.

I think about it every day and it haunts me.

18. What? Why?

Instagram, dwyguy_22

Sometimes when I’m drunk I pee on the faucet in the bathroom. So when someone else finishes washing their hands and turns the water off, they now have my piss on their hands. I feel bad about it sometimes, but I just can’t help myself.

19. “I want to experience as many as I can.”

Instagram, mikeolenick

When I was around 10 years old a friend of mine showed me his mom’s porn. It was a Hustler magazine (pretty hardcore to see first IMO) and it fascinated me. Obviously they focus pretty intently on the vagina in Hustler and it created this weird fascination/addiction in me.


I became fascinated with vaginas and promptly started reading/learning everything I could about them. Down the line this has turned into a full blown obsession with pleasuring women. During sex I no longer care if I even cum as long as they do. I’ve perfected my skills to the point that several women have told me they can’t even masturbate themselves as well as I can for them. The negative part to all of this is that I have become obsessed with sleeping with as many women as possible simply for the fact that all vaginas are different and I want to experience as many as I can. Sadly this has resulted in me stacking up a rather embarassing list of previous lovers that kind of eats me up inside a little. I always wonder if I’m some kind of freak…

20. F*cked up

Warner Bros.

21. Sexual Tension


So, this has been going on for a while. My wife has this totally hot friend and she comes over frequently. Usually my wife drinks too much and passes out wherever she sees fit. This leaves me and the friend to our own demise.


There has always been a sexual tension between us. One night when this happened I took the friend upstairs. To fuck her. When I got up there I couldn’t do it, felt too guilty. So I told her she was amazingly pretty and went to bed.

She came over again one night and the usual happened, wife got too drunk and passed out. Sexual tension started building and before I knew it, my finger was in her pussy. It was awesome! It made me feel alive again. I have never even kissed her, but I’ve finger banged her. Totally rad! I don’t know if I would want to make out with her, I don’t want to be with her at all, I just want to satisfy my lust for her I guess.

I would totally do it again if the opportunity presented.

22. Stereotypes


I am a black high school student living in a majority white town in New England. I have lived in this town all my life and I guess you could say I “talk white”, whatever the hell that means. In my school, there is only a few black kids that live in the town. They’re all good kids. All the other black kids that attend my high school get bused in from a large city 15 miles north of us. There is a program that allows inner city kids to attend school in rich suburbs with good school systems. Most of these kids are dumb, loud, obnoxious trouble makers. They accentuate the black stereotypes soooo hard. Most of them are bad kids, but then again, there are a couple that I’m pretty good friends with who were all raised in good, hardworking families. I just hate most of the kids from the inner city because they make me look bad just because they’re the same color as me. It makes me really mad that I get instantly grouped in with them just because we have the same skin color. This has rolled over outside of school too. I just try to avoid black people in general because I always assume that they will be ghetto, loud and rude. Ugh.

22. Flashing


I sometimes flash my father and pretend that it was an accident. I pretend to “accidentally” drop the towel I wrap around me after showers, and “accidentally” lose my bra in the pool. I deliberately leave my door room open when changing in hopes of him catching a glimpse.

23. Sexual Blackmail


Nothing would make me happier than a very attractive member of the opposite sex track me down and blackmail me into having sex with them. And then developing mutual stockholm syndrome feelings for each other.

I read a fucking lot of feminist literature. I am super pro-women’s rights. But still. I want to be desired by someone I find desirable to the point where they are willing to break a lot of societal rules to have me.


via didyouknowfacts

Written by Laura McNairy

Laura is a freelance writer for TFLN. She likes to write about what she knows best — dating, sex, and being awkward, but usually in the opposite order. She is the Assistant Editor and videographer for Peach Fuzz, a sex-positive nudie magazine in ATX.