TIFU by trying to last longer in bed with an old high school flame

There was a girl in high school that transferred in halfway through 10th grade. Let’s call her Kimmy. We hit it off immediately and progressed with our flirtation until summer break. For whatever reason we didn’t talk much during the summer even though cell phones and myspace were a thing (summer of 2006; no Facebook yet). When we returned to school in 11th grade things picked up right where they left off but it almost seemed like the time apart did something to us because it progressed rapidly. By the end of the first month of 11th grade I was feeling her up in math class, undoing her bra from behind so that I could reach up from under her shirt and fondle her boobs whenever the teacher was at his desk and couldn’t see us. We 100% would have started fucking within the next couple weeks, however I ended up getting myself expelled due to an unrelated incident and everything came crashing to a halt. We originally were texting for the few days afterwards but the incident was so notorious in my school that it actually resulted in a letter getting sent to all of the parents as well as an automated phone call, and her parents promptly forbid her from having any further contact with me.

We reconnected just before my 21st birthday. She came to my birthday party and we ended up making out in my room while the party was going on in the living room, but she stopped things a bit after her bra came off. She said she didn’t wanna fool around too much while there were people literally just outside the door. We agreed to meet up in a few days when we were both both available again, but something came up and then I got into a relationship right afterwards, and by the time I was single again she was dating somebody new, and so it continued for years with one of us always being in a relationship whenever the other one was single. We maintained an arms length level of friendship for the next several years with the main punchline of our friendship being that every year on my birthday I would message her to ask if this was the year she was going to give me birthday sex and she would playfully respond “maybe next year” and then we’d mildly flirt back and forth for a few texts. There were a few years where the only contact we had all year was our annual birthday conversation where I would reach out about birthday sex and then we wouldn’t talk again until the following year, rinse and repeat.

Then on my 30th birthday I was about nine months into a new relationship however she had recently decided to open it up, and I messaged Kimmy with my annual birthday text. At this point it had just become a joke that I no longer actually even thought was serious so I was very surprised when she responded back to let me know that her serious relationship had just ended and she was ready to finally make this happen. I ended up actually calling her because I was so surprised, we talked for about an hour, and we agreed to meet up the following Wednesday. We spent the next several days exchanging pictures back and forth and I felt like she had only gotten hotter as time had gone on. At this point I hadn’t seen her in person in nine years since the last time we had actually been around each other was my 21st birthday, and she didn’t post much to her Facebook so I actually didn’t know how attractive she had gotten. It was around here I began to panic because the buildup of a decade and a half plus all of the hot and heavy talk for the past week had me feeling insecure. I was concerned that this would wind up being an instance of there being so much buildup that the actual performance would end up being underwhelming because it had been built up too much. I got into my head and my performance anxiety manifested into a specific fear of not being able to last long enough. This was partially fueled by my worry that because I had been wanting this for so long that I would bust the moment I entered her because I would be so happy to have finally got it in. Mind you I had never had an issue of finishing too quickly and had always lasted a reasonable amount of time with all of my partners throughout the years, so this was a completely unwarranted fear that came out of nowhere. But I became fixated on it, and ended up getting advice from a bunch of my boys and the Internet about how to last longer. The number one thing everybody said was to bust one out before meeting up with her in order to take the edge off so it would take me longer when her and I actually were doing it.

Wednesday rolls around, I do as instructed, and then head over to pick her up for our “date“ before we would be heading to a hotel. We grabbed dinner down in the tourist area and then impromptu decided to go mini golfing. That led to us just walking around catching up and talking. We actually had a blast, but it ended up being several hours before we were in the hotel. I became concerned that so much time had gone by that any benefits I had gleaned from popping one off before leaving were long gone, as I’d now had more than enough time to recharge. Almost as soon as we were in the room she started undressing and pushed me onto the bed and I quickly said I had to pee really fast. Rather than peeing, as you can probably guess I instead popped one off again real quick. I then came back into the room and it started getting hot and heavy. Go time, and… little dude will not stand up. Now I’m panicking, which only makes things worse, and I literally can get zero movement out of him whatsoever. I realize it’s because I just finished a few minutes before and need some time to recharge, so I play it off by eating her out, the entire time playing with myself trying to get anything to happen. I end up doing oral for way past the point of enjoyment for her, to where she actually stopped me and asked me if I’m ever going to fuck her. At this point I’m still as flaccid as can be, but I think maybe if I rub my dick on her vagina, it might jumpstart it. So now I’m straddling her while essentially limp dick massaging her vagina. I’m a grower not a shower so the option of just fucking her soft was literally not an option, but I tried to push as much of myself as I could into her hoping something would happen. Eventually I ended up getting just the head inside of her, and essentially gyrated on her for about three minutes without really doing anything at all, then pulled out and just stared at her in complete defeat. She was actually very nice about it, but it was very obvious that she was incredibly disappointed. I told her I was having performance anxiety and that if we maybe watched TV or something for a little bit and then tried again in about an hour I would probably be fine, but she was visibly turned off at this point and politely told me that she was tired and thought maybe we should just go ahead and end the date. At this point I practically begged her to let me try again, and somehow in one last Hail Mary effort was able to achieve a semi and at least get into a sort of sex like rhythm. I ultimately did the worst performance of my life but figured it was at least better than nothing. We got dressed, hugged goodbye, and went our separate ways. I think the most humiliating part of it all was going home afterwards and having to act like everything was perfectly fine around my girlfriend, because even though we were in an open relationship we definitely didn’t talk about our escapades and I damn sure wasn’t going to be telling her about this monumental failure. A few days later I decided to reach out to Kimmy to explain myself and found myself blocked.

It’s been 4 1/2 years and I’m now happily married to someone else but today I was made to think about this night because a mutual friend of ours created a group chat on messenger, and apparently even if people have each other blocked on Facebook they will still see each other on messenger if they’re both added in a group chat. As soon as I saw her name and pfp in the chat I felt my face go red. The worst part of it is that I know she absolutely cooked me to some of our mutual female friends, a few of whom are also in the chat. I know for a fact that she essentially told everybody that I couldn’t get it up for her and went on to talk about how it was a huge disappointment and I was the reason she decided she was never going to hook up with anybody else that she’d ever had a thing for in the past. Kind of a “better in mind than actuality“ situation and I made her decide to never do it again. My first thought was to remove myself from the group chat, but I decided to stick around since I doubt anything embarrassing will come from it. But who knows, maybe I’ll have to write another one of these in a few days depending on how thing end up going.

TL;DR: I thought if I popped one out right before sex I could last longer, but ended up limp dick flaccid while trying to have sex with a woman I’d been wanting to hook up with for 14 years.