I was 18, and in was my freshman year of college. I’d been dating the guy for a couple months. We were both virgins, and I thought he was the one . . . Anyway, we had tickets to see Les Miserables in Charlotte a week after the winter break. Campus was a bit over an hour from there, and I suggested we get a hotel, so we wouldn't have to drive back so late. I obsessed over what to wear, bought new lingerie . . . I even wore actual stockings, which I freakin' hated (and still do).
The play was wonderful, and afterward we came back to the hotel. He sat on the end of one of the beds and turned on the tv. Nothing was on but the Jerry Lewis telethon. I thanked him for the lovely evening, and kissed him. His eyes didn't leave the screen. I asked if there was anything special he wanted to do . . . he said no.
So I decided maybe he was nervous . . . And asked him to unzip my dress for me . . . He did, then went back to the tv. I made a point of slowly removing the dress . . . and nothing. I removed my slip . . . still nothing. I went into the bathroom, primped a bit, and tried to give myself a pep talk.
I came back and asked to see the remote. He said, “There's nothing on, “ and handed it to me. I tossed it to the corner of the room and asked if that's all he’s gonna' do tonight. (Mind you, I had no idea what I was doing, and it took a boatload of nerve to do this .) He just gaped at me . . . and said, "like what?"
You know those moments when you wish you could freeze time so you can break things and slap the stupid out of someone without getting caught?
I took a deep breath, and borrowed a line from Bull Durham. “I'm trying to seduce you, for God's sake, and I'm doing a damn poor job of it... Aren't I pretty?” He didn't get the reference (sigh), but he did at least say, “Oh. I didn't know you wanted to do that.”
What I wanted to say was, "No, I always dress like this when I do tv repair work."
What I did say was, "Well, yes. I thought that would be a nice way to cap off a romantic evening."
Him: Uhm, okay.
Me: (thinking--gee, don't get too excited there, fella) Well, if you don't really want to . . .
Him: It’s not that . . . I just didn’t know you were thinking about it tonight. I’m not exactly prepared.
Me: Lucky for you, I am.
I got out the candle I brought, lit it, and put a couple condoms on the night stand. Then I stood in front of him, and he just gave me a deer in the headlights kinda’ look. I suggested we start making out first, and go from there.
Eventually, we got down to business. He put on the condom, and entered me. But when he drew back, he popped all the way out--and he didn’t notice!! He just kept pumping away, with his cock between my legs. I was too mortified to say anything. So I laid there and waiting for him to finish. Once he did, he laid on top of me, and I start thinking, “This could only happen to ME ,” and “Well, at least I know he wasn’t lying about being a virgin.”
My warped sense of humor kicked in, but I had just enough tact to know that laughing just then was a bad idea, so I held it in. It got so that I was literally shaking, and tears began to stream down my eyes. My boyfriend lifted himself off me and looked down at me with concern. “Are you okay? Did I hurt you?”
Oh. My. God. That was it. I could not hold it in any longer, and literally laughed ‘till I fell off the bed. I laughed until my sides split, and all my makeup had run from the tears flowing down my face. When the laughter subsided, I caught my breath, and explained to my very perplexed boyfriend what had happened. He was doubtful, but I assured him it was true, and apologized for the laughter. I then asked if he would like to try again, so that we could cure ourselves of this pesky virginity.
The second attempt was technically successful, but I was still left thinking, “Is that all?” That feeling lasted pretty much the rest of the time we dated.
My first non-waterpik-induced orgasm happened about a year later, thanks to Mr. Sweet. He was 19 as well, and I was his first (but I didn't know that at the time).
=)