Skip to main content

TIFU by getting flustered as I was about to lose my virginity

I (m 28) have moved to Colombia for work. It came with a promotion for the IT company I work at and it is also the first time I have left the US.

Now one thing that I was desperate to lose while in Colombia was my virginity. I figured a change of scenery would definitely help with this.

Over the weekend a friend invited me to a party where I hit it off with this attractive girl (f 25). It has been a while since I felt chemistry like this with someone of the opposite sex, and as the night progressed soon we found ourselves at her place.

I was playing it cool and trying to go with the flow, we went down on each other...so far so good. Then I was about to stand up and get the condom from my pants when she opened her drawer and pulled one out. I reached out to take it but she said "dont worry I can help you" and proceeded to open it and roll it on me.

This really threw me off my game. I had envisioned this moment many times and it always involved me handing the condom and putting it on. I even practiced this on my own during my alone time.

As she rolled it down she look up and smiled...I was overwhelmed in that moment and to my dismay I freaking popped right into the condom as she was rolling it down!

I was mortified and blurted out a "oh no no" and she sat there with a look of shock on her face. She stood up to get some paper towels to wipe me off as she took the condom off.

Ended up leaving after about an hour later. She mentioned that she had an early morning. I have not stopped thinking about it all morning. Reddit, any advice for me here?

What surprised me was how much of the lead she took, and it threw me off my game.

TL;DR - Thought I was going to lose my virginity but instead came when the condom was rolled on

Labels:

Comments

Post a Comment

Popular posts from this blog

TIFU almost so bad by not unlogging from this Reddit account

I use this Reddit account to mod r/hearhimfuck , watch my porn and answer NSFWAMA when I feel like it. I religiously log off completely after every time because I don't want my partner or anyone knowing about this account. It's the holidays and we are all busy so I had a quick session with myself and ran to get a shower and leave for another family Christmas dinner. My phone stayed in my purse the whole evening. By the end there's 6 of us left and we're sitting in the living room, having mellow conversation. Pets are discussed and photos shown. Someone asks about my dogs so I go fetch my phone and sit back on the couch. As soon as I unlock it, there's a full blown ANAL clip playing. Fortunately, the sound was off. I manage to turn the sound all the way down and shut the app without anyone seeing. TLDR; Iwas THIS close from having hardcore porn blasting surrounded by my parents, my partner, an aunt and a two cousins. I can't imagine the aftermath of what could...
Post a Comment
Read more

TIFU by fucking my coworker

Happened a couple of days ago, but yeah, as the title says... Oops... We've worked together for about a year now; we've always been friendly, but I never really clocked her as a potential romantic option; she's my coworker, she had a boyfriend when we started working together, and to be honest I just thought she was completely out of my league: I'm a schlub and she is gorgeous So when she texts me asking if we want to hang out after work, I genuinely thought nothing untoward would happen; I thought we were just going to chill and watch cartoons; and for a while we were just having a nice platonic hangout. But we got very drunk, and eventually she was giving me the bedroom eyes and saying we should make out. I very emphatically said that was a bad idea, but she kissed me anyway, and at that point I really lost any semblance of self-restraint.. I am not proud of myself, at all. I can tell myself that she came onto me, but ultimately I also comepletly let it happen. No...
Post a Comment
Read more

TIFU by shopping on Amazon

So I have an Amazon account, and a family. Anyhow, the person I'm seeing likes to do things with me... try new things if you know what I mean 😏 Recently I've ordered a few packages with adult toys, swing, etc. And... clone a willy. It came in yesterday while I was out. While I was out I got a notification that the cloning kit came in. I sent my son a text asking him to bring my Amazon package in. He said he had already. I didn't think much of it. Until last night when I went to go... use it. I asked my son where the package was on my way out the door. He asked "The plant stand or the cloning kit?". Mind you, the boxes DO NOT say what the contents are, nor were they opened. He must have realized what he said because my face is a goddam story book. I just stood there silent and shocked. He pointed towards the closet. This has been going on for ages, but he has NEVER indicated knowing what's in the packages. So now my teenage son knows his mom is a freak. ...
Post a Comment
Read more