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The next day I didn't chicken out, but instead told him what time he needed to pick me up to go to the train station. I told him to bring anything he might be interested in playing with, and hinted that I would be doing the same.
Friday night, the first Friday in March (the night before my birthday, actually), was going to be the night. If I had ever thought of going the corporate route, I probably would have lost millions of dollars over my lifetime by my utter failure to get any reading done that week. Lord forgive me, I was thinking of it as a wedding night; I had intimated as much to Charles on the phone, saying I think (I had stiffened my resolve with several glasses of wine before making this call), "One last question, Mr. Smith: are you prepared to deflower a virgin anus?"; "Oh. . . um. . . sweet Jesus, Emily, are you trying to give me a heart attack?" was his reply, which did indeed sound weak, as if he were having a cardiac episode, at which I broke down into giggles, unfortunately. At any rate, I was not going to lose the chance to indulge my thing for white lace thongs.
We agreed that we wanted to concentrate on getting the scene right, so we wouldn't try to have dinner beforehand (well, he agreed when I said that was what we should do). We would just take the train down to New York, and go straight to the hotel room I had reserved. (Yes, it was the Waldorf; why the fuck not, I thought. It was not the bridal suite, as it's allegorized in EXPLORATIONS: Books 1-5; I'm a very fortunate girl, with respect to my socioeconomic background, but I'm not that fortunate.) This is probably the time when you're realizing, reader, that I'm terrible about topping from the bottom. I'm very lucky, though, that most of the time that's exactly what Charles needs: I made all the arrangements, even told him what he was going to wear. Hearing his breathing become labored over the phone when I told him these details was. . . exciting.
The most difficult part of the whole thing (if you except the welcome difficulty of taking Charles' cock in my ass for the first time) turned out to be not having sex on the train. I had already discovered my tendency, which continues to this day, to cling to him, physically at least. I clung to him on the train, and I put his coat over us, and I took his hand and put it under my skirt. That was when he actually discovered that I had shaved down there. I hope I never forget the look on his face.
"Tell me how naughty I am," I murmured. He looked around nervously, and then gave in.
"You are a very, very bad girl, Emily Tilton," he murmured back. I realized that I was in danger not just of soaking through what I was thinking of as my "warm-up" panties (white lace mesh), worn in case Charles decided to change the script, haul me into the train bathroom, and take me, but of leaving a stain on a nice blue skirt that I'd worn for the subtle schoolgirl effect. The thought made the problem even worse. "You're going to get a spanking tonight."
He made a circle around my clit with his forefinger at that moment, and I came, to his and my delight, astonishment, and mortification, because I had made a sound somewhere between a shout and a grunt, and even biting the collar of his coat hadn't muffled it much. Also, I undoubtedly looked like I was having a seizure of some kind and had, I believe, turned bright red. Heads turned.
"Oh my God, Charles," I said. "This is. . . new." I put my hand on his lap and felt something so, well, authoritative, that at first I drew my hand back in something like alarm. He, though, took my hand and put it back on his cock.
"This is for you," he said. "But you're not going to get it until I'm ready to give it to you, you naughty little slut."
"Oh. No," was all I could say, because the problem--the warm, wet, aching problem--had begun all over again. And then, I couldn't help it. . . I said "I love you, Charles."
And he said, not missing a beat, "I love you, too."
The next day I didn't chicken out, but instead told him what time he needed to pick me up to go to the train station. I told him to bring anything he might be interested in playing with, and hinted that I would be doing the same.
Friday night, the first Friday in March (the night before my birthday, actually), was going to be the night. If I had ever thought of going the corporate route, I probably would have lost millions of dollars over my lifetime by my utter failure to get any reading done that week. Lord forgive me, I was thinking of it as a wedding night; I had intimated as much to Charles on the phone, saying I think (I had stiffened my resolve with several glasses of wine before making this call), "One last question, Mr. Smith: are you prepared to deflower a virgin anus?"; "Oh. . . um. . . sweet Jesus, Emily, are you trying to give me a heart attack?" was his reply, which did indeed sound weak, as if he were having a cardiac episode, at which I broke down into giggles, unfortunately. At any rate, I was not going to lose the chance to indulge my thing for white lace thongs.
We agreed that we wanted to concentrate on getting the scene right, so we wouldn't try to have dinner beforehand (well, he agreed when I said that was what we should do). We would just take the train down to New York, and go straight to the hotel room I had reserved. (Yes, it was the Waldorf; why the fuck not, I thought. It was not the bridal suite, as it's allegorized in EXPLORATIONS: Books 1-5; I'm a very fortunate girl, with respect to my socioeconomic background, but I'm not that fortunate.) This is probably the time when you're realizing, reader, that I'm terrible about topping from the bottom. I'm very lucky, though, that most of the time that's exactly what Charles needs: I made all the arrangements, even told him what he was going to wear. Hearing his breathing become labored over the phone when I told him these details was. . . exciting.
The most difficult part of the whole thing (if you except the welcome difficulty of taking Charles' cock in my ass for the first time) turned out to be not having sex on the train. I had already discovered my tendency, which continues to this day, to cling to him, physically at least. I clung to him on the train, and I put his coat over us, and I took his hand and put it under my skirt. That was when he actually discovered that I had shaved down there. I hope I never forget the look on his face.
"Tell me how naughty I am," I murmured. He looked around nervously, and then gave in.
"You are a very, very bad girl, Emily Tilton," he murmured back. I realized that I was in danger not just of soaking through what I was thinking of as my "warm-up" panties (white lace mesh), worn in case Charles decided to change the script, haul me into the train bathroom, and take me, but of leaving a stain on a nice blue skirt that I'd worn for the subtle schoolgirl effect. The thought made the problem even worse. "You're going to get a spanking tonight."
He made a circle around my clit with his forefinger at that moment, and I came, to his and my delight, astonishment, and mortification, because I had made a sound somewhere between a shout and a grunt, and even biting the collar of his coat hadn't muffled it much. Also, I undoubtedly looked like I was having a seizure of some kind and had, I believe, turned bright red. Heads turned.
"Oh my God, Charles," I said. "This is. . . new." I put my hand on his lap and felt something so, well, authoritative, that at first I drew my hand back in something like alarm. He, though, took my hand and put it back on his cock.
"This is for you," he said. "But you're not going to get it until I'm ready to give it to you, you naughty little slut."
"Oh. No," was all I could say, because the problem--the warm, wet, aching problem--had begun all over again. And then, I couldn't help it. . . I said "I love you, Charles."
And he said, not missing a beat, "I love you, too."
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