Dan

To my great shame I had just graduated high school still a virgin. I had set the goal for myself at about the age of 13 that I would get laid in high school, but never quite pulled it off. Not that I didn’t have grilfriends, but I was always attracted to “good” girls who might go down on me or give me a hand job, but who wouldn’t ante up when it really came down to it. I would usually get frustrated with them, break up with them, and try another one. Once you get a reputation for doing that (advice to those in high school still trying to get laid), it gets pretty hard to get any traction with girls.

So anyway, I was spending the summer between high school and college working as a busboy at the Mount Washington Hotel in New Hampshire. If you’ve ever been there or seen it, you know that it’s a hugely impressive grand hotel, kind of like the one in the Shining. It is massive, opulent, and expensive. And I was the hired help. Lowly help at that. But whatever, I was an 18-year-old kid with a lot of energy and pent-up lust waiting to break free. Even though it was strictly frowned upon, I hit on every good-looking girl guest around my age. Because I worked in the main dining room, I saw them all. I would try to drop suggestions or be cute to get their attention. If I got one who was game, and a surprising number were, I’d ask them to hook up later. I would then, as the guest of a guest, have access to parts of the hotel where I otherwise wasn’t allowed.

I would do my best to romance these girls, walking with around in the grounds at night, with fog coming off the golf course and deer out in the fields. I figured that if this setting couldn’t get me laid, nothing could. Whether or not I was right about that, I did finally get it.

This girl named Donna came through a buffet line I was manning one morning. She had huge breasts, and wasn’t trying too hard to conceal them. She was kind of average looking overall, not stunning, but she did have a fun kind of positive energy, so I made small talk with her.

I saw her again at dinner and asked her to meet me later. She agreed. During the afternoon the waiters were talking about her and joking with me about whether I could pull it off. It was also the 3rd of July. Fireworks were planned for the next evening. Trust me, it’s so cheesy I would never make it up.

I don’t really remember the details of how, but somehow we ended up in her room that night. We were both really nervous, but we were fooling around really seriously and getting close to doing it. Just as it started to seem really possible, she called it off. But she was hooked. We lay there and talked for a couple hours, and tentatively agreed that we might do it the following night.

That day, as I mentioned, was the 4th of July. She had a room on the back side of the hotel, overlooking the pool and the mountains. I saw her at breakfast and dinner again, and we smiled at each other and planned to meet up later. That afternoon while I was off my shift we hung out, and made out a couple times. She gave me totally free run of the huge tits, which was great by itself. They were so firm, like only an 18-year-old’s tits can be when they’re that big and real. Just melony goodness.

That night it was all planned out. I got some condoms and went to her room. In retrospect, it would have all been much smoother if we’d had even just a beer, but we were totally out of luck with getting booze, so we were totally sober. Except that my buddies had gotten me high earlier, so I was kind of high and feeling a little like a deer in the headlights. I was doing my best to be smooth, though. I never told her that it was my first time too, I just acted like I was being really understanding that it was her first time. I didn’t think she would trust me enough to do it if she knew it was my first time too.

I had the idea that we should take a shower together. So we did; we got naked and turned off all the lights and got in the shower. We were both into it, but it was awkward and were also both a little stiff and nervous. But it warmed up and pretty soon we were making out and she was rubbing my dick and balls with her soapy hand. I was trying to finger her, but because I was several inches taller and we were both standing up, I could never quite get to the stretching I was trying to do.

She got me really hard. I finally decided it was time, so we got out of the shower and dried off. She started to get very tense and because I was nervous too we had some bursts of really stupid conversation and cheesy “romantic” lines. Romantic like pulp fiction. Not.

Anyway, we layed on the bed and I put the condom on. She grabbed my dick and started working it with her hand, keeping me really hard. I lay next to her for a while, fingering her. I remember thinking that the water in the shower had washed away a lot of her moisture and wondering if it would be hard to get my cock into her. Finally I got up above her and got my cock into place. For a split second she started to get really scared and I was afraid she’d back out, so I started trying to push it in. It was hard to do. I could tell it hurt her, but she leaned into it and we both concentrated our weight on our pelvises and all of a sudden I burst her cherry and rammed all the way into her. I was so surprised that it had worked, and so psyched that I wasn’t a virgin anymore, I loosened up quite a bit real quick.

She had tears in her eyes and said it hurt but that it was ok. It went pretty quickly. Probably about 8 good strokes before I came. But I sort of tried to hide the fact I’d came and continued to fuck her for maybe a minute. By then my dick was feeling like it might be getting soft, so I pretended to come then. Oh yeah, no joke, there are 4th of July fireworks going on outside the window as all this is happening.

Anyway, I didn’t get to fuck her again because she was leaving the next day. She wrote me some letters afterwards and invited me to come to where she lived to fuck her some more, but I never went. I was sort of embarrassed that it hadn’t been more romantic and that it hadn’t been great sex. I always wished, since then, that I would have told her it was my first time too, instead of trying to act all cool. I think it still would have happened and it would have been a better experience for both of us.

The great p.s. to the story is that eventually I did go on to have great sex with many very cute girls and then, later, women. So for any guys out there who feel like chumps when you’re just getting it for the first time, keep at it guys, you’ll get better. And women, thanks for putting up with us while we learn.

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