At first I tried to back out of it, but Caroline was determined that the party would happen just as she’d planned, and she had answers for every excuse I offered.
Of course I didn’t have to be in love with the guy, she argued, it was my duty to explore and experiment first so that when I did find a guy I loved, I could appreciate him. And no, we weren’t exploiting her friends by planning it in advance. After all, wasn’t it a time-honored tradition for an experienced relative to take a young man to a brothel where he learned his first lessons in pleasure? Why couldn’t women do it, too? Besides, she’d bet her new car that whichever guy I chose would welcome the exploitation.
Finally I confessed my real fear. ‘Suppose he freaks out when he discovers it’s my first time?’
‘Most of them will probably be flattered, but I guess there could be the odd throwback who still thinks the first time should be special. So, if he asks—and he probably won’t—you should just lie.’
‘But he’ll be able to tell, won’t he?’
‘Absolutely not, Lydia, because you’re going to do “homework.” And we both know what a good student you are.’
‘What do you mean?’
‘I mean that the next time you play with yourself—and I know you do, so don’t try to pretend you don’t know what I’m talking about—you should put something bigger than a finger inside. That way it won’t hurt much at all when the guy puts his dick in.’
‘Caroline,’ I said, a nervous laugh bubbling up in my throat, ‘I don’t think I can go through with this.’
But the truth was, the more we talked, the more I wanted to do it. Caroline was offering me more than an A-list group of Ivy League boys from a rich D.C. suburb, a keg of beer to put them in the mood, and the free run of her house, with Aunt Jean and Uncle Bob tucked safely away in a country inn on Maryland’s Eastern Shore for the weekend. She was giving me something even more precious—the freedom to travel to a foreign land where I could do anything and be anything I wanted, if only for one night.
It was a gift I’d have to travel halfway around the world to find again.
CHAPTER FOUR
Caroline was clever to call it ‘homework.’ She knew I couldn’t resist the chance to get an ‘A,’ even if it was in the art of masturbation. And so I told my mother I had to study for a test and retired to my bedroom early that night.
I lay in the darkness, my hairbrush beside me, the handle carefully washed with mild soap and dried with a clean towel. My heart was pounding in my throat. I played with myself all the time, but I’d never put anything inside, not even a finger. Would there be blood? Would I scream out in pain? Would my hairbrush respect me in the morning?
My hands wandered under the covers, and I slowly hiked my nightgown up to my waist. I slid my hands down over my belly, tracing feathery circles with my fingertips as I went. My right hand dipped between my legs, the left settled on top, protectively. This was my usual position for self-pleasuring, but it suddenly seemed funny, as if one hand were trying to keep the other from escaping. This time maybe it was.
I touched my middle finger to my clit. I was already wet, and in fact, I’d been tingly down there since my talk with Caroline. My heart was a taiko drum, hammering louder and faster, and I feared for a moment that I might come in a few strokes and blow the assignment.
I took a few deep breaths and forced my finger into a lazier rhythm, teasing flicks rather than a desperate, home-stretch strumming.
And then, suddenly, I knew I was no longer alone. My eyes were closed, but I could feel him walk into the room. I smelled him, too, Old Spice aftershave and a hint of male sweat. He didn’t visit me every time I touched myself, but he’d been coming regularly almost from the beginning. I never saw his face, but I knew he was an older man from his voice, a bit hazy, as if he were calling through a door, but deep and smooth and utterly confident I would do everything he commanded.
‘Pull down the covers, Lydia,’ he said softly. ‘You know I like to see your naked pussy when you play with yourself. Much better than watching a twitching little lump of hand jiggling away under the blanket.’
I felt a sweet stabbing sensation low in my belly, lust and shame all twined together. Obediently I pushed the blanket down so that anyone standing at the bottom of my bed would have a fine view of my lower half, thighs parted, vulva exposed.
‘What’s this I see beside you? Are you going to do something naughty with that brush?’
Reluctantly I nodded, my eyes squeezed shut.
‘You have become a bad girl since you started listening to your cousin. But of course I’m very glad you’re taking her advice. The world would be a happier place with more women like her.’
‘I’m not sure I have the nerve to do what she said,’ I confessed. My lips weren’t moving, but I knew he understood.
‘Of course you do. I want you to do it, and you don’t want to disappoint me. Why don’t you pick up that brush and press it against your virgin hole?’
With a quivering hand, I reached for the brush and held the rounded end of the handle against my secret lips.
‘Very good. Now push. Gently. Very gently.’
Ever the star student, I probed myself gingerly with my makeshift dildo. There was a mild stinging sensation, but with steady pressure I managed to coax it in a few inches. I pressed my other hand to my chest to keep my heart from jumping free of my rib cage.
‘A little farther now,’ the voice urged.
‘I don’t know if I can.’
‘Try, Lydia. For me. Show me how brave you are.’ I pushed. The entire handle slipped inside.
‘Very good. I knew you could do it. Now move it in and out slowly. I know you want to open yourself for your lover. And for me.’
This is indeed exactly what I wanted. Somehow he always knew just what to make me do, as if he could see desires inside me I myself didn’t understand. He knew when it was time to stop the fucking movements and ease the brush out, knew I could soothe the lingering soreness by touching my clit again and coming on my hand, while he watched and murmured words of approval and even snapped a few photos for his collection along the way. And then, as quickly as he’d come—and I’d come—he vanished into air.
Afterwards, I curled up under the blankets, hugging my extra pillow to my chest like a lover. Could any real man know me so completely? Especially if, as Caroline said, I had to lie to him to lie with him?
Sex and honesty didn’t fit together so easily. Even as a virgin, I seemed to know this was true. Which is why it was so funny that I ended up telling the guy who popped my cherry the truth from the beginning.
CHAPTER FIVE
Mike wasn’t even on Caroline’s list. He was the cousin of her boyfriend of the month and stopped by before the party to help deliver the keg. Caroline told me he was cool enough to put the deposit required by the liquor store on his credit card so she didn’t have to pony up the cash.
I could tell he was older—twenty-three, I found out later, a Brown graduate, already working at a non-profit ‘saving the world,’ as his cousin put it with a good-natured sneer. Mike wasn’t cute in the good cheekbones way Caroline liked, but I liked his dark curls and the way he filled his jeans. What really got me were his sturdy hands clutching that keg and that suggestive grimace of exertion as he bent over to set it down. Lust made me bold, and after I thanked him for his help, very nicely, I asked