First, my first time. Not hers, but mine. So I was giving her a ride home from my house, which is about a half hour drive. We'd been dating for about three months at this point, and I was ready to get beyond just groping. As we were passing the local CVS, she said "You know, we should probably keep some condoms on hand, just in case..." Me, being the calm, cool, collected guy I am, cut across a lane of traffic, cutting some very upset person off, just so I wouldn't miss the parking lot. I dashed in, like a kid at Christmas, and ran back to the condom aisle, took a moment to get over the initial shock of how many there were, and just grabbed a box. I paid for it, dashed back out, and quickly got back on the road. We got back to her room, spending the remaining 20 minutes in mostly silence. We got back, got into her room, and I was ready to just get down to it. She, on the other hand, stuck the box in her dresser, and said "We'll just leave these in here for when we need them." I moped to the bed, and sat down as she turned on the TV. Flipping through the channels, she kept trying to strike up a conversation, but all I could think of was "I just bought condoms. I'm supposed to be making the sex right now." More importantly, my dick was at attention, wondering when the fun was going to start. Finally, the gf settled on Scarface, since I'd told her it was pretty good, and she'd never seen it. So she laid down in bed and managed to get me in a horizontal position. I was watching the movie, and my mood started improving. Eventually, my train of thought went something like "Y'know, this is a pretty good movie. Al Pacino's a badass, can't beat the tacky shirts, they're running around with a chainsaw, I have a hand on my dick, Al Pacino's accent is pretty coo...wait...hand on my..." at which point, I glanced back to see her smiling at me. We commenced with the kissings, the gropings, the strokings, and finally, she told me to go get a condom. I jumped up, sprinted across the room, grabbed one out of her dresser, and dashed back, ripping open the wrapper, and putting it on. She positioned herself accordingly, as did I, and it happened.
Now, up to this point, she had sworn that she had been with two guys, and I had believed her. What it felt like, though, was that she made a habit out of being fisted by the Hulk. I continued though, getting no traction whatsoever, but I was playing the good sport, and she seemed to be enjoying herself.
Cut to an hour later. She's still having the time of her life, and can't believe I'm nowhere close to finishing. I didn't have the heart to tell her that it felt like I was thrusting into an oversized hole in the wall. Finally, I let out a grunt, tell her I just finished, then removed the condom and threw it away before she could investigate. I felt REALLY bad afterwards, since she was singing my praises, but I was getting seriously winded, and she wasn't all that interested in getting on top. And thus, Dan lost his virginity.