Everyone wants their first time to be special…but were not sure this is exactly what they had in mind. We’ve all heard the perfect how I lost my cherry stories, but what about when it goes wrong? These first time fails are sure to be unforgettable.
Ready when you are.
“I held out until after college to lose my virginity, and it was definitely not the orgasmic event I was hoping for. My less-than-endowed boyfriend and I decided we’d do the deed one night, and during a heavy petting session, I told him I was ready. His response? ‘I’m already in you.’ Oops!”
Petting the Kitty
I had never seen a penis (in person) in my entire life and had no idea how to handle one. During foreplay he whipped it out and I was afraid that if I gripped it with my fist I would squeeze too hard and hurt him. Instead, I patted the top of it with two fingers (like the way you would pet a small kitten) for a few minutes until he asked me if he could show me how he liked to be touched. We somehow managed to have totally normal sex after that but when I think back on that I’m glad he wasn’t weirded out.
Missing You
Well basically I was fucking the space between her and the bed or against her vagina, but never made its way in. The worst part is I thought I was a total stud because my friends told me your first time you’d only go a few seconds. So in my head and bragging to my friends I was hot shit because I could go forever. My girlfriend never said anything, and I did that way 3-4 times. Finally one night were in the back of my car after a concert and I’m doing my usual and somehow I make my way into the actual hole I already thought I was in. My mind exploded, and so did my penis a second later.
Do you have a funny or awkward first time story? We would love to hear about it!
