These People Lost Their Virginities In The Most Awkward And Hilarious Ways

The one with the condom struggles

“After fooling around with my GF for a few weeks she finally hints that she’s ready to go for it tonight and that I should buy some condoms. I run to the chemist after work and am faced with 20 different types of condoms, I just grab the normal type and try not to seem too nervous while paying.

“We get to her place that night and things start getting hot, we finally strip naked and I get the condom out. Having never used a condom before but not wanting to show it I casually try to keep up conversation while I’m struggling with all my might to put the damn thing on. After breaking the first one I kinda excuse myself and walk into the bathroom with a second condom and the instructions.

“After a few minutes I am panicking because the fucking condom will not go on and am mortified that I look like an idiot who can’t even put on a condom.
She finally walks into the bathroom confused and suggests I try a condom she had in her purse just in case. That one is not going on either and I’m standing there with a boner in one hand, unrolled condom in the other muttering apologies and feeling absolutely ridiculous. ‘Maybe the condoms are too small,’ she comments, ‘we should buy XL one’s. I thought that was nice of her but I never had thought my penis was above average.

“So she convinces me and we get in my car and drive to the nearest chemist, and then came the second most awkward part, this was a different chemist and this one did not have any condoms on display, so I had to ask an elderly lady for condoms for gentlemen with extra girth. The lady smiles and looks at my girlfriend waiting in the car outside. She goes to the back of the store and hands me the box with a wink and told me to have a nice night. Later we sexed and it was glorious.”