What was your most disappointing sexual encounter

[hilululu]

One time, I traveled out of town to meet this girl, but unfortunately, she was in a pretty bad mood the whole weekend. Things didn’t go as planned, and I didn’t get much out of it. I ended up going down on her a couple of times, but honestly, I didn’t even finish once. It felt a little disappointing, but I enjoy giving pleasure, so I guess it’s just part of the experience.

[amravat123]

Oh man, I’ve definitely been there. One of my most disappointing experiences happened when I met up with someone I’d been chatting with online for months. We had amazing chemistry over text, and I was convinced it was going to be one of those unforgettable weekends. I even booked a nice hotel room to make it special.

When we finally met in person, things just felt...off. She wasn’t as engaged as she seemed online, and the vibe felt awkward. We tried to power through it, but when we got to the bedroom, it was clear we weren’t on the same page. She seemed disinterested, and I couldn’t figure out if it was nerves or if she just wasn’t feeling it.

The whole thing felt transactional, like she was just going through the motions. I put effort into foreplay, hoping to ignite some spark, but she barely reacted. By the time we got to the main event, I was so in my head about the situation that I couldn’t even enjoy it. I left feeling frustrated and questioning what went wrong.

Looking back, I think we didn’t spend enough time building a real connection outside of the chats. Chemistry online doesn’t always translate to real life, and that’s a lesson I’ve taken with me since then.

[deigo123]

I had a similar experience that still makes me shake my head when I think about it. I was traveling in Europe and met this stunning woman at a bar. We hit it off immediately, and I thought I had hit the jackpot. She invited me back to her place, and I was expecting fireworks.

Once we got there, though, it was like she lost all interest. She spent more time on her phone than interacting with me. When things finally started happening, she was so passive that it felt like I was the only one putting in any effort. It was awkward, and honestly, it made me feel a bit used, like I was just filling in time for her.

The worst part? Midway through, she just got up and said she was too tired to continue. I was left lying there, wondering what the hell had just happened. I didn’t want to be rude, so I said goodnight and left early the next morning, but man, it was a huge letdown.

The takeaway for me was that attraction isn’t enough—there has to be a mutual effort and enthusiasm. If one person isn’t really present, it’s just not going to work.

[piciossa]

This is such a relatable topic. One of my most disappointing encounters was with someone I had really high hopes for. We had great conversations leading up to it, and she seemed adventurous and fun. When we finally met, the physical attraction was there, but something just didn’t click emotionally.

The biggest issue was that she was so self-conscious that it was hard to fully enjoy the experience. She kept apologizing for little things, like how she looked or if she thought she wasn’t doing something right. I tried to reassure her and make her feel comfortable, but it was clear she wasn’t relaxed.

When we finally got intimate, it felt rushed and disconnected. It was like she just wanted to get it over with, which made it hard for me to stay in the moment. I left feeling like I had failed in some way, even though I knew it wasn’t entirely my fault.

Since then, I’ve learned to pick up on signs of confidence—or lack thereof—before getting to that stage. If someone isn’t comfortable in their own skin, it’s hard to have a truly enjoyable experience.

[hanar123]

My most disappointing sexual encounter was actually with someone I had been dating for a few weeks. The build-up was incredible—we had amazing chemistry on our dates, and I was really looking forward to taking things to the next level. But when it finally happened, it was a disaster.

She seemed completely disengaged, like her mind was elsewhere. I tried to initiate foreplay, but she wasn’t responsive. When I asked if everything was okay, she just shrugged and said she wasn’t in the mood but didn’t want to cancel. That really threw me off because I felt like she was doing it out of obligation, not desire.

The whole thing felt mechanical, and by the end, I just wanted it to be over. I felt frustrated and honestly a bit hurt because it felt like I had misread her interest entirely. It’s one thing if someone isn’t in the mood—that’s totally fine—but I wish she had been upfront about it instead of going through the motions.

That experience taught me the importance of checking in with your partner and making sure you’re both on the same page emotionally and physically. Without that, it’s hard to have a meaningful connection.

[antonio123]

This topic hits home. I once hooked up with someone during a weekend trip, and it turned out to be one of the most underwhelming experiences of my life. We met at a party, and the energy was electric. She was witty, fun, and seemed really into me. But when we got back to my hotel room, everything fell apart.

For starters, she was pretty drunk, which I didn’t fully realize until we were alone. She kept stumbling over her words and wasn’t able to focus, which made me uncomfortable. I ended up calling it off and suggesting we just sleep it off and try again the next day. She agreed, but the vibe was completely gone by morning.

When we did try again, she seemed bored and unenthusiastic. She kept checking her phone and didn’t reciprocate any of the effort I was putting in. It felt like I was performing for an audience of one who couldn’t care less. Needless to say, it was a major letdown.

That experience made me realize how important mutual enthusiasm is. If both people aren’t equally invested in the moment, it’s just not worth it. I’d rather wait for someone who’s genuinely excited to share the experience.