I had just turned 19, she was 18, both freshman virgins.
We had been dating for 5 months, had a failed attempt around the 3 month mark
We decided to rent a motel room in town, so we didn't have to deal with the stress of having a roommate try to come into the dorm. We went to dinner in a restaurant connected to the motel, kind of awkward as we both know what was "supposed" to happen afterward.
So we get to the room, do our usual foreplay and then I reach for the condom, aaaaand I go soft trying to put it on. No matter what she did I was staying soft. So were both laying there for a few secs, it's kinda awkward but not so much as we had been together awhile.
I think to myself "I"M DOING THIS" so I hop on top and start eating her out until I get hard again, I penetrated and entered her vajajay WITHOUT a condom (seeing as it was the condom that was messing with my mind).
After a few thrusts my gf opens a condom and slips it onto my dick as I pull out, and then I continue thrusting.
Was very painful for my girl, as she was a virgin, but she told me to keep going (as she's crying), this kept me from finishing my first time. But we banged again in the morning and it was great until......
I SEE THAT THE CONDOM BROKE AFTER I PULL OUT
She freaked out but we got plan b and went on with our lives.