The Education of Lisa

A few weeks after losing my virginity to a certain rock star who shall remain nameless (unless you want to go back and read Chapter 3,) I met my future husband on a blind date. I was completely unimpressed.

William was the twin brother of my best friend Carrie's then-boyfriend Bobby. I learned with disappointment, however, that they were not identical twins. Bobby was hot, a real live fireman with ash-blond good looks, gym-pumped muscles and (Carrie assured me) a huge cock. The brothers were a bit older than us, somewhere well into their thirties, but while Bobby was boyishly handsome, William was prematurely balding. He had thick glasses and slight paunch. He was shabbily dressed and poorly shaved.

On top of all this, he was shy to the point of near-silence and I had to work hard to keep our conversation afloat through an agonizingly long dinner. It was a double date with Carrie and Bobby, and when it was finally done, William rather staidly kissed my hand and asked not for my phone number, but my e-mail address. I figured there was no harm in this and surrendered it. William thanked me for a wonderful evening and excused himself, leaving me as Carrie and Bobby's third wheel.

"So," Carrie said. "What do you think?"

"I don't know," I said. "We didn't really hit it off."

Carrie shrugged. "Yeah, we were afraid of that. But Bobby wanted me to ask you if you wanted to come back to our place for a three-way."

I declined as politely as I could, knowing that this would probably destroy our friendship. The fact that Bobby would even ask her such a thing also led me to believe that their relationship was not long for this world. This prediction came true about a month later, after Carrie had agreed to a menage a trois with some girl they picked up at a bar. Bobby, it turned out, liked this chick better and promptly dumped Carrie. I figured that was the end of that, and I wouldn't ever hear from William again.

This was a strange phase in my life. I had recently emerged from a long-term relationship with an anally-obsessed Republican Mormon (long story.) Then I had lost my technical virginity to the afore-mentioned rock star. I was not yet twenty, relatively inexperienced, and looking for love. Sex was the path I chose to this goal, but it turns out that one does not necessarily lead to the other.

Carrie had discovered early on that any reasonably attractive girl could get laid anytime she wanted to, with nearly any man, if she made a direct offer of sex. Carrie would just pick out a guy she liked and ask him straight out if he wanted to fuck. If he said no, she'd just pick out another one. Not very many said no. She had about an 80% success rate with this approach.

I tried that a few times myself, but these encounters left me not only dissatisfied, but also deeply shamed. I don't know. Carrie could, with few qualms, give a blow-job in the parking lot to a guy she'd met ten minutes before, but that wasn't really me. I'm not even sure that was really her, either. Carrie, for all her affected free spirits, wasn't really a very happy person.

Don't get me wrong. I'm no prude. I did have a somewhat repressed Mormon upbringing, but that was something I was bound and determined to shed. I love sex. I love having fun. I saw nothing really wrong with one-nighters or with "hooking up" with a guy the same night I meet him. I didn't expect love from these guys but, and this was the thing, I did expect a bare minimum of kindness. I didn't expect marriage or commitment or anything like that, but why pretend you're not home when I call the next day? Treat me nice and I'll happily fuck your brains out. Be a dickhead and I quickly lose interest. That seems like a simple proposition, but it was beyond most of the guys I met.

Here are some examples of the winners I dallied with in those days:

* Gordon, a bass player in a fairly decent bar band (me and my musician fetish.) Carrie seduced the lead singer and I wound up with Gordon as a "collateral hookup." After a four-minute fuck at his apartment, he asked if I'd please leave because he had to go to work early the next morning. I know it's asking a lot, but I really like a guy to make me eggs the morning after.

* Brad, another bar pick-up, on whom I bestowed a fantastic blow job. His way of expressing gratitude? "Could you blow my buddy Ralph, too? He just broke with his girlfriend and he's depressed."

* Matt and Erin. Yes, a prospective three-way with a guy and his girlfriend. I was up for it in a "what the hell" kind of way (after several tequila shots.) But when we got back to their place, Erin began to sob, saying she couldn't go through with it. Matt got pissed, saying that she'd promised, and Erin locked herself in the bathroom. At which point, Matt turned to me and, predictably, said: "Well, you and me can still fuck." The fact that I went along with this said more about my self-esteem than his charm.

*Mark, who actually took me out to a very expensive restaurant. Afterwards, he said I could either pay my half of the bill or, "maybe we can work out some kind of trade."

* Jordan, a good-looking, charming and friendly man. He took me out several times, treated me well and was great in bed. The problem? Oh, well, he somehow forgot to mention that he was married and had a four-year-old son. Must have slipped his mind.

Add to this list a few very scary near date rapes and you can see why I wanted out of this scene. Plus, if any guys are reading this, let me tell you a personal pet peeve of mine. When a girl says she doesn't want to have sex with you, the line "You could at least blow me," contains zero charm. And, if the girl finally caves in to your whining and wheedling and sucks your little ding-dong, please do not at any point utter the phrase: "Oh yeah, suck it, bitch."

In the midst of these dark days, when I was beginning to lose all faith in the male gender, Will's e-mails began to arrive. At first, I'd actually forgotten who he was and, when I did remember, I thought he was stalking me. I deleted the first several of these messages, not even bothering to read some of them.

Still, they kept coming, every couple days, and my curiosity got the better of me. The messages were brief, witty, thoughtful. He said things like: "I was at the supermarket the other day, and I saw they had a special on orchids. I thought of you, how you'd said that was your favorite flower." Remembering a casual comment I'd made, and forgotten, months before.

It got to be that I looked forward to hearing from Will, and was even disappointed when he didn't write me. Even on a bad day, he made me laugh. Eventually, I began to write him back. Our correspondence went on for weeks. Even in the realm of cyberspace, he was a complete gentleman. He never pushed me for any kind of personal information unless I volunteered it first, never asked me out, never got sexual. I could even ask him for advise on guys I was seeing. His replies were thoughtful and even helpful, devoid of any trace of jealousy.

At that time, I was seeing a guy named Ryan. I say "seeing," but "screwing" might be a better word. The sex was really good, and Ryan was a great-looking guy, but any time I suggested we do anything outside the bedroom, or made any move that he interpreted as indicating any kind of emotional investment, he would get cold and withdraw.

Will told me that the curse of good-looking men was that many of them had learned that they didn't have to give up anything to get what they wanted. As long as they could find women willing to go to bed with them without demanding any emotional investment in return, they would do so because they had no reason not to. Will warned that if I became too demanding, Ryan would simply find some other girl willing to have sex with him, who wouldn't ask for anything else, for a while anyway.

This, of course, turned out to be true. Ryan didn't bother telling me that he was seeing anyone else and Will called that one, too. "If he can get sex from two women, he will do so for as long as he can." Even when I found evidence (another girl's panties tangled in the bedsheets) and confronted Ryan, all he did was shrug. "I never said I wasn't sleeping with anyone else." That, to his credit, was true, but it was at that point that I decided I wanted out. Ryan didn't seem to care one way or the other, and this was what stung me the most.

In the days that followed, I did a lot of thinking. Maybe, I thought, my taste in men was in fact my own worst enemy. The guys I was attracted to, the really good-looking ones in my book, all turned out to be flaming assholes. Then there was Will. Quiet, unassuming, totally lacking in confidence and charisma, unathletic, unfashionable and balding. Point for point running counter to what I found attractive in a man. He was also kind, generous, funny, perceptive and sensitive. All things I claimed to want in a man, but which were conspicuously missing in every guy I'd ever been with.

So, as an experiment, I decided to give Will another try. I e-mailed him and asked him out to dinner. To my surprise, he turned me down.

"We tried that," he wrote back. "I think I'm better with writing words than I am with speaking them in person."

I wrote back a long, confessional letter, pouring my heart into an explanation of my emotional needs, which were not being served by the men I went out with. I expressed cautious hope that he might be able to save me from myself.

"I will only disappoint you," he wrote back. Then he presented a long list of reasons he was not what I was looking for. The difference in our ages, his own emotional baggage (in this message he told me for the first time that he had been married for several years and had had a rather bitter divorce.) His self-doubt, insecurity. "You're a wonderful person and a very beautiful woman," he wrote. "You deserve better than me."

I wrote back that his problems were much like mine, and that if we could each overcome all of our doubts about ourselves, then perhaps we could find a measure of happiness with one another.

We went back and forth like that for a while, getting deeper and deeper into emotional confessions, until the act of electronic messaging turned into a baring of the soul. Then, a week later, I received a very short reply to a very long and very raw e-mail I'd sent him.

"I've just spent the afternoon reading over our correspondence," he wrote back. "Jesus, do I take myself too seriously. I'd love to go to dinner with you. Shall I pick you up at 8?"

I smiled for an hour.

When I opened the door for him that night, his eyes went wide behind his glasses.

"My God," he said. "You look beautiful."

His look was so frank, his words spoken with such sincerity, that I blushed and had to look away. I was wearing a red dress. A bit low-cut and short-skirted but nothing like what Carrie called cock-bait, which was what I usually wore when I went out bar-hopping.

"You don't look so bad yourself," I said. And he didn't. He had on a sweater-vest, a look I normally associated with my Dad, but on Will tonight it looked good. I smelled a hint of nice cologne in the air, too.

"Shall we?" he said, and then he actually took my arm.

He took me to a somewhat expensive Italian place. At first, our conversation was stilted and awkward, but after a few glasses of wine and some effort on my part, Will came out of his shell and we regained the easy rapport we'd developed in our e-mails. We talked and laughed easily, like we'd known each other for years. We kept it light, too, with none of that emotional heaviness of our recent correspondence.

Afterwards, he took me home. We talked for a while longer in his idling car and, when we finally ran out of words, he attempted to give me a good-night kiss on the cheek. I turned my head at the last second, though, and caught him full on the lips. I kissed him, open mouthed, for what felt like several minutes. He resisted at first, but gradually melted into my kiss. I took his shaking hand and placed it on my breast.

"Come inside," I whispered in his ear.

"Lisa," he pulled away. "I don't think I sh. . ."

"Yes," I interrupted. "You definitely should. I want to go to bed with you tonight."

"I don't think we're ready . . ."

"I'm ready," I said. "And if you don't come in right now, I'm going to go to some bar and find some guy and have a cheap, emotionally self-destructive one-night-stand. You don't want me to have to do that, do you?"

"No, but . . ."

"No more arguments, Will. I want you. Come inside."

He grinned then, didn't say another word. He followed me into my apartment.

I'd been planning for this all day. I had candles set up all over my bedroom and I lit them as he watched. I played slow sexy jazz on my stereo, then stood before Will and let him cover my lips and my and my neck and my shoulders with his light fluttering kisses.

"Undress me," I gasped.

Delicately, with shaking hands, he slid the thin straps of the dress off my shoulders and pulled it slowly to the floor around my ankles. I kicked it away and stood before him in silky black bra and panties. He pulled the straps of the bra down and kissed my chest and the tops of my breasts. My nipples cried out for his lips. Will put his arms around me, caressed my back for a while before finding the clasp to the bra. He undid the clasp cautiously, but didn't fumble at it the way a lot of guys do. The bra fell away and was forgotten. Gentle kisses turned my nipples to pebbly nubs.

His light suckling kisses moved like butterfly wings down my belly. Will was on his knees before me, like a man at prayer. He kissed the front of my panties, then slid them down my legs so slowly I thought I was going to go crazy. Will leaned forward and his lips found my clitoris. I arched my back into his kiss. I could smell myself, musky and heavy in the candle-lit air. My own scent made my mouth water.

"Stand up," I said.

Will did so. The confidence he had shown in revealing my body evaporated when it came to exposing his own. He seemed uncomfortable as I pulled off his sweater, and unbuttoned his shirt, and peeled off the t-shirt he wore under that. I couldn't help noticing he was sucking in his gut. I wanted him to relax, so I ran my hands through the hair on his chest and kissed him as he had kissed me. Slow descending flutters. His neck, his chest, his nipples, his belly, his waist, until I was kneeling before him as he had kneeled before me.

I undid his belt, unzipped his pants, pulled them to the ground. Boxer shorts underneath. He stopped my hand as I tugged at the waist-band.

"I'm kind of small," he said shamefully.

I insistently pulled the shorts down and was face-to-face with his cock. He wasn't all that small. In the past several months, I'd seen more than my share of cocks. Will's was maybe at the low end of average, but I'd seen much smaller. Matt, the guy who'd wanted a three-way with his girlfriend, had been downright stubby.

"Looks pretty good to me," I said. To prove it, I gave the partially erect penis a long, slow kiss. I licked away a pearly bead of pre-cum. Will pulled away like my mouth was an electrical socket.

"I don't want to . . ." he said.

I nodded up at him and smiled. Standing up, I grabbed his now fully hard cock and led him over to the bed like a dog on a leash. We laid down together, spooning, naked.

"I haven't had sex since my divorce," he whispered in my ear. "That's almost five years. Would it be all right if I just . . . touched you for a while?"

I was used to guys whose idea of foreplay was jamming a finger in to see if I was wet, and looking around for a bottle of lube if I wasn't. Will, though, held me as his hands explored every part of my body for what felt like hours. He kissed me as he touched my breasts, toyed with the nipples with a child-like fascination. I rolled onto my back to give him easier access, and guided his hand down between my legs. His fingers parted my wet divide, grazed my clitoris, shyly dipped inside. His touch was so light, so tentative, that I actually put my hand on his to make the pressure stronger.

"Can I . . ." he struggled for the words. "You know, with my mouth?"

I nodded enthusiastically. Rare, I'd found, was the man who would eat your pussy on the first date. Will approached this as he'd approached everything else, with utmost caution, kissing around my thighs in gradually decreasing circles until he zeroed in on my pussy, which was by now gurgling with anticipation.

In terms of style and technique, perhaps Will was not as skilled as some other guys who had gone down on me. The rock star, in particular, comes to mind as a cunnilingual master. But you have to give him points for enthusiasm. Will licked and sucked and gobbled and gulped, drinking from my well like a man dying of thirst. Some guys, I know, are put off by the taste and the smell, but Will seemed to delight in getting my juices all over his face. He made all these moaning yummy noises and I even felt his nose dip inside me a few times. I was so wet, I was almost afraid he'd drown down there.

Then something happened that's never happened to me before. I started to shake. My legs, spread out to admit his face, began to shiver and spasm. I grabbed the back of Will's head and pulled him harder into me. He was humping the mattress frantically. The quaking rocked my entire body and I bucked my hips into his mouth. I came so hard it brought tears to my eyes. I felt something spurt out of me into his mouth and he greedily drank it up.

He sat up, smiling at me through lips dripping with my juices. He picked up his undershirt off the floor and wiped his face off. Too bad. I wanted to kiss it away, to lick my own pussy off his face.

"Come here," I said. I wanted him to fuck me.

"Just a minute," he said. He got up and rooted in his pants pocket until he found his wallet. He opened it up and pulled out a condom.

"I bought it just in case," he explained sheepishly. "I didn't really expect to . . ."

"Whatever," I said. "Just hurry."

He fumbled around with the rubber for a few seconds, then climbed on top of me. I could feel him poking around clumsily down there. I reached down to help him guide it in, but found him only partially hard. He shied away, fell back on the bed beside me.

"I'm sorry," he said miserably. "I don't know what's wrong. I really want to."

I could see that he was blushing with embarrassment even in the candlelight. He looked like he wanted to cry.

"It's all right, Will," I said.

I sat up and leaned over him, peeling off the condom and taking him into my jaws. I gave him my slowest, wettest blow-job, stroking him with my other hand. It wasn't long before he was admirably hard once again.

"Thank you thank you thank you," he moaned as I worked on him. Pure gratitude. It beat the hell out of "oh yeah, suck it bitch."

I released him from my mouth and lay back down on the bed. There were a few more awkward moments of condom application and searching for the entrance, but then he was inside me.

I put my arms around his back and pulled him close as he rocked his hips into me, rolling with gentle waves. I reflected then on the phrase "making love," for the first time really understanding how this act could literally create love between two people. Every time Will fell into me, I felt closer to loving him. Other guys might have been better lovers, by that I mean more skilled, but Will was literally loving me, while all the others were only performing the motions of love.

Thinking this brought me to the edge again, and hearing Will grunt and feeling the condom inflate inside me sent me right over the other side. This orgasm was lighter than the first, like a hot flash pumped through my entire bloodstream.

We kissed for a long time as he withered inside me.