This is a true story. The dialogue took place over seven years ago, so it’s reconstructed here, rather that transcribed. But it’s pretty close.
I was in Dallas to see a client. I was with an account executive, a woman named Lorraine.
The first night we were there, we had dinner with the client at the Atrium restaurant of the hotel. The client is a runner and he has to leave us at 9:30. He wants to get to bed early so he can do about 5 miles before our meeting in the morning. Glad I’m not a runner.
The client is very good looking and obviously he’s fit. I mean, for one thing, the guy can run five miles. Despite these awe-inspiring pluses, on an off day I’m be willing to admit that I find him about as interesting as a Hollywood Squares re-run. But then, it occurred to me (this was not the first time) that I’m not a woman. Out of curiosity, I ask Lorraine if she found him attractive.
“No. I mean I guess he is technically. But he’s dull.” Right answer.
Lorraine’s skinny, very bright, 28ish, freckles, full of energy, has an amazing mound of red hair, pretty, looks a bit like Julia Roberts, but spoken of as “a slut” around the office. (I might say that it’s always other women who call her that and by that they seem to mean that she is fairly open about liking sex. I, personally, don’t see this as a big negative. But then that’s me.) I’ve worked with her for about eight months so far and, as you can tell by my description, I like her. Some fairly candid discussions with her in the past and we’ve laughed some together, but I’ve never laid a finger on her to this point.
Drinks throughout.
“Now you … well,” she says, “certainly not dull. You make me laugh. But … now don’t take this the wrong way, it’s a compliment really … but I could never think of you sexually because you remind me of my father.”
Well, an interesting way of putting me off. Effective too.
I laugh, but am maybe just a bit stung.
Still, it gives me an opening to have an open discussion about sex – and her sexual experiences -- without her having to feel I’m making a pass. We know each other well enough and she has told me things about “Got my brains fucked out last night” or “He’s hung like a horse.” That kind of thing. So there’s not really a chance that she’ll think I’m stepping out of bounds. The boundaries were already pretty far out there.
(I tell myself that I like these kinds of discussions because they teach me about how women really see these things. How they really think about their experiences. How differently they see it all from the way men see it. Because, after all, getting women to open up (!) and tell their real feelings and attitudes is the only possible way I would ever find out about these things that are – by definition – outside of a man’s experience. Makes sense right? Of course there just might also be the tiniest bit of a turn-on for me in these talks. But that’s hardly my prime motivation, right?)
“First time?”
“Intercourse?”
“Yes.”
“In a car. He talked me into it, he thought. But I was very ready. If it hadn’t been that night it would have been the next or within the week. Not very satisfactory from my point of view, which I guess is too much of a cliché. Still it wasn’t his fault. I was just caught up in the sort of technical task of getting rid of my virginity. Getting myself off was probably about tenth on the list of things going through my mind.”
“Did he enjoy it?”
“What a dumb question!”
“Why?”
“Men always enjoy it as long as they get off. And he shot his wad after about four strokes. But I’m being unfair. He was only about 18: might have been a virgin himself, though he said he wasn’t – maybe just to give me confidence.”
“How old were you?”
“18 years, 107 days.”
“Late bloomer.”
“In some ways, I guess. In others no.”
“Meaning?”
“Well, when I was 13, I had an experience that really opened my eyes to all that. We had a summer place in the Hamptons and that year, one of my brother’s friends had come out to stay with us. His name was Jamie and he was about to go off to Boston University in the fall, so he must have been 18, maybe 19. I used to spy on the two of them in sort of a casual way. But one morning – there was a shared bathroom that opened on two bedrooms: mine and theirs – I heard someone go in, and I went to the keyhole to look. I had already seen both of them nude through this keyhole a number of times … seen them taking a piss, caught them taking showers, you know. It was a bit of a turn on, but it was as much educational as anything. This time though, Jamie locked both doors, turned on the tap to fill the bath (this was a bit strange, because the guys always took showers) and then took all his clothes off. But this time was different than the other viewings, because I was surprised to see that Jamie had a hard-on. It was the first “stiffy,” as we used to call them, I had ever seen. It so surprised me that it even took a moment for my mind to register exactly what it was. Remember I was only 13. Anyway he got in the bath while it was still running and lay back with his head at my end of the tub, facing the other direction. I remember all of this vividly; I can still picture it clearly even as we sit here. I couldn’t see his head because of my limited viewing range, but I could see most everything from his waist down. And with the tub filling up, he started to stroke himself. He was left-handed. His cock was sticking straight up and was very, very hard (the way high school boys cocks get). And then he reached for the soap and got his cock totally lathered up and started really pounding himself off. Then suddenly I could hear a sort of groan/whimper and he shot his cum into the air – straight up – and then again and a third time. It’s a good thing the water was running because I was panting so hard, I’m sure he would have heard me otherwise. I was so excited I could have come right there kneeling at the keyhole. I thought this was the most amazing thing I had ever, ever seen in my life.”
“But you didn’t come?”
“Not for at least another minute! I kept watching during his come down, but I reached down to my cunt and felt that it had just sopped my panties. And then I lay down on the floor, on my back, right by the door – I remember feeling my heart which was violently pumping – scrunched my panties down, not even bothering to take them off and jiggled myself off in record time. One of the best orgasms I’ve ever had.”
“You already knew how to do that at thirteen?”
“Oh yes, I certainly did.”
“Did you ever tell this Jamie what a big role he’d played in your life? You know, like years later?”
“No, but I wasn’t finished telling you about that summer.”
“You saw him again?”
“Shhh. Quit asking questions and let me tell it. God, I can feel myself getting wet right here just thinking about all this stuff again.”
“Are you really?”
