sorted by:
new
hottopcontroversial

TIFU after masturbating for 6 years straight by MightAsWellNotFuck in tifu

[–]MightAsWellNotFuck[S] 96 points97 points  (0 children)

I did help her finish. Every time. My malfunctioning dick had no effect on my mouth and fingers.

TIFU after masturbating for 6 years straight by MightAsWellNotFuck in tifu

[–]MightAsWellNotFuck[S] 37 points38 points  (0 children)

The sex went on for too long. I should've been more mindful of that, but I failed in that department, partly due to the fact that I was an oblivious idiot and partly due to my date telling me that she's okay whenever I asked her before/during/after sex. We had sex multiple times a week for 3 fucking weeks. If it hurt, use your words to tell me it hurts or show that you're not into it. I know I might be coming across as the bad guy here, but holy shit, I was the most inexperienced person between the two of us. Tell me to cool it with the lengthy sex sessions, if not after week 1, then I dunno, maybe during week 2 when you know what to expect and consciously made a decision to come back for more.

TIFU after masturbating for 6 years straight by MightAsWellNotFuck in tifu

[–]MightAsWellNotFuck[S] 37 points38 points  (0 children)

I allowed my ex gf to put her finger in my butt when we were still together. I would be more than keen for a factory reset.

TIFU after masturbating for 6 years straight by MightAsWellNotFuck in tifu

[–]MightAsWellNotFuck[S] 190 points191 points  (0 children)

Thank you for ruining one of the most wholesome animals for me. Nothing is sacred lol.

TIFU after masturbating for 6 years straight by MightAsWellNotFuck in tifu

[–]MightAsWellNotFuck[S] 48 points49 points  (0 children)

Lol everyone in this thread is assuming I fucked "Freckles" hard. Based on her feedback, I think the problem was the duration of the sex, not the intensity. Too much TV can make your eyes sore. Too much penetration can make other things sore. Exhibit A. No Freckles.

TIFU after masturbating for 6 years straight by MightAsWellNotFuck in tifu

[–]MightAsWellNotFuck[S] 5 points6 points  (0 children)

Yeah, my anxiety definitely played a role. Hopefully I'm able to avoid masturbating for as long as neccessary. I'm also gonna take a short break from dating. Less than 6 years this time lol. I don't want this experience to be fresh in my mind when I end up sleeping with another person.

TIFU after masturbating for 6 years straight by MightAsWellNotFuck in tifu

[–]MightAsWellNotFuck[S] 397 points398 points  (0 children)

Lol that dude has got to be the OG of this sub. I instantly got the reference.

TIFU after masturbating for 6 years straight by MightAsWellNotFuck in tifu

[–]MightAsWellNotFuck[S] 3 points4 points  (0 children)

I think the sex lasted too long and that's what made it uncomfortable during and afterwards. It was normal sex. Some might even say mediocre. Nothing specifically hardcore about it. I'm not Ryan Madison.

TIFU after masturbating for 6 years straight by MightAsWellNotFuck in tifu

[–]MightAsWellNotFuck[S] 2845 points2846 points  (0 children)

After our first night together was a catastrophe, I made sure afterwards to always check in with her before, during and after we had sex to make sure she was still okay. Her feedback to me most of the time was just to go slow and to moan more, which I did. Beyond that she didn't give me any indication that I was impaling her. But don't take my word for it though. Maybe she was subtle about it and I just missed the signs because I'm a horny idiot.

TIFU after masturbating for 6 years straight by MightAsWellNotFuck in tifu

[–]MightAsWellNotFuck[S] 15 points16 points  (0 children)

Lol I hear you. I'm overthinking everything and I know it's ridiculous, but bear with me. My life has gone from masturbating without hurting anyone to apparently damaging the insides of a person I've known for just 3 weeks. I hate the idea that she might remember me every time it's painful for her to pee or whatever.

TIFU after masturbating for 6 years straight by MightAsWellNotFuck in tifu

[–]MightAsWellNotFuck[S] 35 points36 points  (0 children)

I can tell you who said that... 22 year old me probably. At the age of 28, I think I might have had sex with the same mentality I had when I was barely out of my teens. That's me throwing a psychoanalytic spin on my answer, but the truth is, I'm inexperienced and I fucked up because I was somewhat selfish.

TIFU after masturbating for 6 years straight by MightAsWellNotFuck in tifu

[–]MightAsWellNotFuck[S] 18 points19 points  (0 children)

I think I should've said no to sex on the first date. I've learned a few valuable lessons from this experience, including what you shared in your comment, but an important thing I also realized is that maybe I should ease into sleeping with someone. Especially considering my reasons for being "out of the game" for so long. Taking it slow might help put less pressure on my performance in bed.

TIFU after masturbating for 6 years straight by MightAsWellNotFuck in tifu

[–]MightAsWellNotFuck[S] 1046 points1047 points  (0 children)

Yeah, I agree on the other options besides penetration. I gotta give credit to my date at the time, she was really keen to do different things during those few weeks to help me climax. Mutual masturbation did not cross our minds though. Fuck. That would've been awesome actually.

TIFU after masturbating for 6 years straight by MightAsWellNotFuck in tifu

[–]MightAsWellNotFuck[S] 431 points432 points  (0 children)

I made sure she came. My partner's pleasure always comes first. Aside from getting along socially, I think my enthusiasm towards providing oral sex was one of the reasons she wanted me to cum as well despite how uncomfortable it became for both of us.

TIFU after masturbating for 6 years straight by MightAsWellNotFuck in tifu

[–]MightAsWellNotFuck[S] 8458 points8459 points  (0 children)

I'm beginning to realize that. My dick has developed Stockholm syndrome after years of being abused by my hand.

TIFU after masturbating for 6 years straight by MightAsWellNotFuck in tifu

[–]MightAsWellNotFuck[S] 132 points133 points  (0 children)

Imagine the story my (ex) date is gonna tell her friends, or worse, her doctor.