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Fresh off the heels of some, uh, fascinating stories about the worst sex people ever had comes yet another riveting set of tales sure to make you squirm a little.

Over the weekend Redditor ilyaimyfix asked the masses, “What’s your biggest sexual regret?

Needles to say, that question combined with the anonymity Reddit affords led to some very funny, odd, and in some cases, disturbing answers.

Ready? Hold on, here we go…

Dropped a girl off at her front door after a successful date. Said goodnight, kissed her, and said “I’ve always wanted to do that”.

She responded “was there anything else you wanted to do?”

“Nope. Good night.”

I drive away into the night, grinning like the stupid 19 year old I was. It wasn’t until a couple of years later I realized I’d missed an opportunity. ~ harplaw

 

Similarly, I was at a girl’s place, hanging out and having a few drinks before heading out. I’d kissed her previously and knew she was interested.

I walked in on her getting changed, and said “Oh shit, sorry”, to which she said “well, maybe you should get naked too”. I took a second, then said “What? No, I’m already dressed to go out.”

I didn’t realise what I’d done until about 2 weeks later. ~ dspm90

An ex-girlfriend invited another couple over to have a four-way. Except, it was a threesome because I wasn’t in town at the time. ~ Link-to-the-Pastiche

 

A girl I was sleeping with stayed over at my place, her friend stayed too due to drinking. They slept in my bed and invited me in, I said I would sleep on the floor so they’d have room to sleep. I hate myself. ~ Overly_obviousanswer

 

Banging my friend’s sister. We’re still friends, best friends even, but his mom hates the shit out of me. ~ burnSMACKER

When I was 8 I put my dick into a soap bottle. Dear god I can still feel it burn sometimes. ~pineapple_entspress

 

I stuck a eyeliner applicator in my dickhole. ~ HITLERS_SEX_PARTY

 

I lost my virginity to someone who turned out to probably be related to me. ~ fff_philip

A couple years back I discovered my girlfriend at the time was cheating on me. I confronted her, and we broke up, but it wrecked me. I was all over the place.

She convinced me to go over one night, and I was so depressed I just wanted to get back to normal, and stupidly thought somehow we could get back together.

Anyway, things escalated. Bad decisions were made, and we started having sex. The sex itself was pretty standard, considering the situation, until at one point, just as I was about to finish, I noticed several hickies/lovebites on her neck and shoulder that I hadn’t given her.

That one really hurt. And took a while to get over.

(And for anyone wondering, yes I continued to fuck her, and because it was fueled by anger or whatever, it actually felt pretty great). ~ DenryNayr

 

Banging my ex’s mom. Said mom was single and had been drinking, and decided that this was her chance to be really horny and seduce me.

I had been drinking and i needed absolutely no encouragement to bang someone who looked like a clone of my then-girlfriend but with bigger tits.

The sex was fine, and my ex never figured out. It’s just weird that her mom still texts me when she’s lonely. ~ benyellow

Trying to give myself head. All I got was a week worth of neck pain. ~ rosenpin

 

Letting my best friend at the time convince me to sleep with his wife while he watches. ~Old_stories

 

There was this new girl who transferred to run track at my college (I ran, as well). I was immediately infatuated with her. She had THE nicest body I had ever seen.

Long story short, after going to a lame party together and getting bored, I said I was gonna get out of there. She came with me without me even implying she should. She stripped down to a fucking THONG, in my room, and we made out for like 10 seconds. I’m sure it was so brief because at this point in my life I had never made out with anyone before and was super nervous, so she probably thought I wasn’t interested. I said we should probably just go to sleep, so she rolled over, pulled my arm over her and put my hand right on her tit. I went to sleep. I WENT TO SLEEP. In the morning, I made her breakfast and then took her back to campus. We never hung out again. What. The. Fuck.

If I had been as experienced then as I am now, there is no doubt in my mind we would have fucked like animals multiple times that night. What’s more is one of my better friends from college, who also ran track, started dating her. And he told me about all the crazy shit she was into. Then I REALLY felt stupid.

The end. ~ Snaab

A girl invited me over for a blow job but I said I was sick so I could stay home and watch the Chappelle show. ~ joelpyro

 

Rubbing toothpaste on my penis when I was a kid. Thought I was going to die. ~ silencerider

Alrighty then. I think that’s enough for now.

SOURCE

 

REDDITORS REVEAL – Their Biggest Sexual Regrets And They Are A Case Study In What NOT To Do

 

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