For context I had just turned 18 at the time of this story and was still a virgin. I hadn’t even had my first kiss yet. So you’ll have to bear with me if I sound dumb or clueless throughout this story. And yes, I’m aware 18 is a bit late to be experimenting with condoms but I was a virgin and had never really talked to girls so I never really bothered until the time of this story. I’m now in my early twenties and no longer a virgin and this is a story I look back and laugh at quite often.

Prior to trying on a condom I had no idea that I had a thick penis. Quite the opposite actually, as I all the time considered myself average more or less. The event that led me to find my less than common girth was when I first tried a condom on. I was in my late teens and just had a major glow up (acne went away, started shaving, started gonna a reputable barber for haircuts on a bi-weekly basis). After I had this little glow up I started gaining attention from the girls at my college which was nice. I wanted to learn how to use condoms just in case a situation called for it. I texted a friend of mine who I knew would have them and he gave me some the next day at college. They were Trojan brand, and not the MAGNUM kind either, they were the ones in the blue packaging and they were the most common I would see at the gas station or pharmacy.

So I go back home from college and take the condoms out of my bag and open one. After watching a tutorial video to ensure that I’d be able to put it on correctly I take one out of the wrapper. I hold the condom in the grip that the video told me to and to my shock the condom won’t go any further than halfway down the tip of my penis.. In my head I’m like “what the fuck? the video made it seem like it was supposed to roll down relatively easily”. So I spend about 15 minutes trying to force the condom onto my penis finally giving up and trying on another one thinking maybe the one I had was defective or something. So I pull out another one and try again and it’s more of the same. I give up on trying to roll it down and instead just force my fingers into the condom to stretch it out onto my penis. Even doing this was damn near impossible but after about ten minutes I was finally able to get it on. Keep in mind during all this BS I’m trying to maintain an erection which is constantly coming and going due to the absurdity of this whole endeavor.

After about 10 minutes of trying to stretch the condom onto my penis I finally get it about 3/4 of the way on and let me tell you it was PAINFUL! The condom was so tight that I could only keep half an erection and even then it was excruciating. I remember thinking “how in the hell am I supposed to have sex with this thing on?”. So I call my friend in a huff and said something to the effect of “hey man, what’s up with the condoms you gave me?”. I remember him being silent over the phone for a second and then asking “what do you mean?”. Explaining to him the situation I say “dude I can’t have sex with these, it took me damn near half a decade to get the fucking thing on 3/4 of the way”. He then asked me if I put them on correctly and I said yes, I even watched a how-to video. He ended the call by saying that I needed to buy magnum condoms and that he didn’t have any. Keep in mind that I’m a broke teenager at the time so I then had to ask my dad to buy them for me which was awkward because I didn’t really talk to my dad about that sort of stuff. He was really cool about it though and told me he could grab some on the way home the next day.

So I get from college and wait for my dad to show up with the goods. He arrives home and opens my bedroom door and tosses them to me. I tell him thanks and he tells me he has errands to run. I was glad he was leaving so I could try my new gear on. As soon as I hear him leave I open the package. There were three condoms inside and I hoped I’d be able to do this in one try so I could save the other two. So I rewatch the condom tutorial just to be sure and then I open one. I take it out and it seems a fair bit bigger than the ones my friend gave me. So I take one out and begin to unroll it onto my penis. I get to the end of the tip and then I can’t go any further. I try to roll it down forcefully and it’s painful. I remember audibly saying “motherfucker” and throwing the box of condoms at the wall. I was able to get the condom over the head this time but no further without significant pain and discomfort.

I had to stretch this condom on as well, although it only took me about 5 minutes compared to the 10 minutes it took the typical one. Let me tell you, it strangled my dick all the same. Couldn’t keep a full erection with it on and it was still just as uncomfortable as the other condom. So I took it off and laid in my bed for about 20 minutes thinking, “I’m fucked, I’ll probably have to risk getting STD’s now”. But just as I wondered all hope was lost, I found Reddit. I remember seeing people who had the same issue. I was taught how to measure via picture tutorials and was actually able to get a tailor tape from my friend. That’s when I discovered I was a whooping 6.2 inches in girth. A measurement that I later found out was quite uncommon. It all made sense after that and soon I was able to buy some MySize 69mm condoms online with a visa gift card given to me from a family member, thanks Grandpa. This was also the time when I was able to find calcsd which was a big help as well. I still hate condoms to this day and tend to not use them unless I’m having sex with someone I don’t know that well.

NSFW: yes