Chapter 2

After the night of the conversation with Tori in which she asked me how many women I’ve had sex with, I did a lot of thinking and a lot of soul-searching. I tried several times to come up with “the number,” just keeping track of the women with my fingers and my brain. I was all over the place at first and got nowhere. So, I decided to be more methodical and take it chronologically, and only count the women I’d had actual intercourse with, not just oral sex or messing around. There had to be actual penetration.

What about girls with whom I only had anal sex? Should I count them? I determined that anal sex did count, but there were a few cases of girls that I’d had threesomes with, but never penetrated. I ruled them out. So, with my new criteria, I started over again.

And, yes, it was only women on the list. I’d never had sex with a man. There was one questionable encounter with a girl from the Philippines that I met at a bar in Tokyo. She was very shy and would only blow me and let me fuck her in the ass. In my mind, she was a girl, and I’m sticking to that. I never saw anything that would have made me think otherwise.

I struggled with the list. I would count out the girls, naming them, and once I was in the double digits, my mind would wander, like a stream of consciousness, jumping from one thought to the next, one girl to the next. I would lose count and have to start over. Then, about the third or fourth time through, another name would pop up between two girls I’d already counted, and I’d have to start again.

Finally, I decided that I would get a notebook and try to trace back through my life and record the names, dates, locations and other pertinent information about every girl I’ve ever had sex with if I could remember them. I had no idea how many there were. But, based on the several aborted attempts I’d already made, I knew the number was pretty high.

Tori and I had been married only about three months when she asked the question. We had dated exclusively for nearly a year before we got married. We both knew pretty early on that we wanted to be together. I resisted the idea of marriage as long as I thought possible. It wasn’t that I didn’t love her; I did. It was just that I had been quite active, sexually, before she and I dated. A part of me wasn’t sure I wanted to be monogamous. Hell, a part of me wasn’t sure I even could be. I’d cheated on several prior girlfriends. That’s another reason why I was dreading discussing the list with Tori.

I wasn’t proud of my infidelity, but I wasn’t exactly ashamed of it, either. There were reasons for everything. I believed we should live our lives with no regret, no remorse. However, I also thought you shouldn’t do things to hurt other people intentionally. I had cheated, but I never did it when I was in a relationship with someone who didn’t deserve it. I concluded that if I were committed to making my marriage work, I would need to be totally honest with Tori and tell her everything about my past. More importantly, I realized it was time that I was honest with myself, too.

I sat down and started at the beginning. I knew who was the first person with whom I had sex. You don’t forget your first time. Her name was Julie, and we were in love. As I thought about Julie, though, I realized that my story didn’t begin there. I may have been a virgin when Julie and I got together, but sexuality was already a huge part of who I was. Not only that but the relationship I had just before Julie changed me profoundly and had a major role in making me who I am. It was painful to think about it. I had put most of it out of my mind for a long time. But, I couldn’t understand myself if I didn’t spend some time and recollect on my pre-intercourse life.

I remember that I always loved girls. From a very early age, I was always crushing on one girl or another. I grew up in a house with three older sisters, with a father who was never home. So, I was constantly surrounded by women, and it gave me a unique perspective on the “fairer sex.” I understood them and could relate to them. That gave me the ability to woo them. And, woo them I did.

Until I started working on the List, I had never really thought much about my ability to relate to women or the many relationships I had. Growing up, I was reasonably good looking and had natural athletic ability. I had dirty blonde hair, brown eyes and a boyish face that meant I was often told I was “cute.” However, it wasn’t just my looks that made me popular with girls. I was smart and well spoken, always at the top of my class. That helped, as well. I was a natural leader and often the alpha male in any group I was in, whether or not I wanted to be. That also contributed to my popularity.

But, the thing that I believe attracted girls and women more than any other factor was how I was able to talk to them, to relate to them, to understand them. I listened. I was confident and exuded maturity and sexuality that acted as a magnet. I wasn’t born that way, I suppose. I never even realized I was popular with girls at the time. If you had asked me, I’m sure I would have said “no way.”

But, as I worked on the List, the more I thought back and remembered, the more I realized that my relationship with females was due to my childhood and formative early years. Inadvertently, I learned so much about what girls wanted from hanging around my sisters and their friends. I was an honorary girl scout, which meant that I was always socializing with girls two to four years older than me. They all loved me, thought I was adorable, and included me in all their activities. I heard and saw everything, recording it all in my brain. I had no male friends back then, no male role models. I developed strong feelings of caring, sensitivity, and vulnerability that made me attractive to women.

That may sound like a horrible childhood for a boy. Trust me; it wasn’t. I got to experience things that other boys would never get to enjoy. For example, when the girls would have slumber parties, I was in the middle of them. When they started talking about kissing boys, they would demonstrate on me. As we got older, things became more daring, and I was always the guinea pig. I played “doctor” and “show me yours, and I’ll show you mine” many times.

I was also exposed to sexual situations early on. My parents were swingers. They hid it from my sisters and me, as much as they could. I was always perceptive and curious, so I figured things out long before my sisters did. Over the years, I caught them in many compromising situations.

My dad ran a “head shop” in the middle of the red light district of a military town that was frequented by strippers, hookers, and the occasional tranny. I would hang out at his store on weekends, and the ladies of the night found me deliciously cute and would tease me. They would flirt with my father, too, but you could tell it was different. With me, they were just being playful and teasing me with glimpses of tits and ass. With Dad, they would be much more aggressive, eventually going into his office while I was left to “watch the shop.” Fifteen minutes later, they’d come back out, and the girl would adjust her clothes or touch up her lipstick. He would give them gifts of merchandise, and they’d leave, blowing him a kiss and flashing me their boobs.

My mother was just as philandering as my father. She was a looker, knew it and knew how to use it to her advantage. When my mother enrolled me in Cub Scouts, the other boys shunned me. They all were friends and lived near each other. I was an outsider. Mom wanted me to have a male role model, someone to fill in for my father, to teach me manly things. She fucked one of the scout leaders, and in exchange, he took me under his wing. That lasted until his wife found out and I had to quit Boy Scouts. So, mom enrolled my sister and me in the 4H and started banging the guy in charge of that. We would spend many days at his farm, doing archery while she was in his house getting boned. How did I know? Remember I said I was curious and perceptive? Well, I thought something was up, so I spied on them and saw them having sex.

She wanted us to learn how to ride horses, so she found a guy with horses and would bang him in exchange for lessons. I got free classes, teachers, and mentors on a wide array of topics and suspected she was giving sexual favors as payment. Mom also never once paid for repairs and maintenance on our house, well not with money.

For a period of a few years, my parents always hung out with this other couple. We even called him Uncle Don and her Aunt Angela, even though they were not related to us at all. They were my parents’ swinging partners, and they would come over on weekends every few months. They would all drink heavily and send us kids to our rooms, and then they would swap partners. Dad and Angela would go to the master bedroom, while Mom and Don would go to the guest bedroom. How did I know? I spied. I saw things. Also, we would have to listen to the sex off and on all night.

That all came to a screeching halt one Sunday when Dad caught Don trying to fondle my sister. It was the first time I ever saw my father literally beat the shit out of someone. He punched Don so hard and so many times, he shit his pants. We never saw Uncle Don and Aunt Angela again.

I found my parents’ collection of dirty magazines, erotic books, Super 8 reel-to-reel porn movies, and sex toys. I didn’t know what half of it was, but I was intrigued enough to find out. I also found in a nightstand next to their bed three books: Sexual Behavior in the Human Male and the corresponding version for the female, otherwise known as the Kinsey reports, and Masters and Johnson’s Human Sexual Response. I would sneak them into my room and read them cover-to-cover.

So, my parents never needed to have “the talk” with me. Dad tried once, and I just told him he didn’t need to. I told him in exacting detail that I already knew how babies were made. The knowledge I had acquired came in handy when I experimented sexually with girls. I was able to do things to them that completely blew their minds. Some people might think that I was doomed to sexual addiction, but I’ve never once felt it was an unhealthy obsession.

When I was in the fifth grade, I had a massive crush on this beautiful blonde-haired girl from the seventh grade, named Shirley, who lived in a mobile home behind my house. She played a game with the boys her age, and older, called Seven Minutes in Heaven. The game was basically that the boys spun a bottle and whoever it pointed to got to spend seven minutes, alone, in a dark storage shed with Shirley and do anything she’d let you. Even though I’d kissed many girls when I was used as a guinea pig by my sister’s friends, Shirley was the first to really kiss me for pleasure.

I was in love with her, and she thought I was cute and harmless, so she would let me play the game with her. She took her time to teach me the fine art of French Kissing. She taught me how kissing can be used to drive a girl insane and how to do it.

Apparently, some of the older boys weren’t quite so harmless, as a few years later Shirley ended up pregnant, strung out on drugs, and working the streets for her pimp, Carlos. I know this because when I was a teenager, she would come to my dad’s shop to spend some time with him in his office in exchange for bongs, crack pipes and cosmetic jewelry.

All of that came later. Back when I was in love with Shirley, hanging out with her made me “cool” with a lot of the girls my age, and even some of the older ones. I got a reputation for being a great kisser and great to make out with. So, I had to make out with all of them.

There were three sisters in one family, all stunningly gorgeous. One was my age, one a year older and the third two years older. One summer evening, I’d been outside hanging out with all of them, and some other friends. After I went home, I was in my bedroom and heard a tapping at the window. I look out, and it was Melissa, the oldest of the three girls. She wanted to kiss me, so, I made out with her through the window. After fifteen minutes, she left. No sooner had I laid back down and someone was tapping at the window again. I opened the blinds, expecting Melissa to be back, but it was Meghan, her younger sister. I made out with her for a while, then she left. Again, after a few minutes, someone tapped, and this time it was Madison, the youngest of the three sisters. She climbed in the window, and we made out on my bed until she realized how late it was.

That summer was often crazy like that. Sometimes, the neighborhood girls would sneak me into their sleepovers, or they would sneak out and climb in my window. We would have big makeout parties, just all these girls and me. I would “go with” one of them for a week or so, then we’d break up, and I’d move on to another, then another, then another. While all the guys I knew were busy playing little league baseball and Pop Warner football, I was having makeout parties with their sisters and girlfriends.

It wasn’t all that long before the makeout sessions advanced to light petting parties, then heavy petting. I had opportunity after opportunity to go all the way, but for some reason, I didn’t. For me, it was more like a game. I was so into playing it, that I failed to finish the game.

Then, I got severely playing football and was nearly paralyzed. I spent a year rehabilitating and during that time, life went on for everyone else. All of my friends completed their Junior year and went on to be seniors. When I was finally allowed back in school, it was determined that I’d missed too much and had to repeat my Junior year. All my friends would graduate a year ahead of me and go off to college without me.

I hated it. I was depressed and miserable. All my life, I’d hung out with friends who were at least my age, if not older. Now, I was stuck, surrounded by little kids and girls I had no interest in. I didn’t want to date anyone and stayed home, alone, for months.

Until I met Doreen.

She had just moved to our neighborhood, having transferred from a different school on the far side of town. She was different than most of the girls my age. She seemed more mature. She had massive boobs, the hair of a shampoo model and the body of a Goddess. I pursued her hard and heavy. We lived near each other, and we would walk home every day together. But, she had secrets. There was a hidden darkness to her. You could see it in the backs of her eyes and in the way she carried herself. She didn’t like to go home and would almost never let me near her house. So, instead, we’d go by my house and hang out. We talked and talked every day. Eventually, we started making out.

She would not let me get her clothes off. We did a lot of things that are almost impossible to do with them on, but we managed. We made out every day and would get very hot and bothered. But, she had to be home by a fixed time daily, and she would cut things off and leave, often abruptly and always leaving me with blue balls. She told me it was church related and I didn’t question it.

I quickly fell in love with her, and I told her so. She didn’t believe me, which was frustrating me. I did love her. But, every time I told her, she would ask me why. I would come up with a reason, something romantic or flowery. She shot me down and told me that I didn’t love her, that it was just lust.

This went on every day after school. We’d make out. I’d try to get in her pants or under her bra. She’d stop me, but would let me do anything I wanted through her clothes.

Then, at some point, I’d tell her that I loved her.

“Why do you love me?” she would ask. I’d come up with another reason, Something poetic or artistic, or something that I saw in a movie.

“Nope, that’s not good enough,” she would tell me. “That doesn’t mean you love me. You’re still just in lust.”

We didn’t have sex, but we would get very hot and bothered. Doreen would leave me sexually frustrated every day. While we weren’t having sex, we did talk about it. One day I got quite a shock. I told her I wanted to have sex with her, but she said no.

“I get it,” I said to her as I was rubbing her pussy through her jeans, which were warm and damp against my hand, “You’re a virgin, too, and you want to do it with someone who really loves you and that you love.”

“Oh, I’m not a virgin,” she said directly.

I was stunned. Doreen was not a virgin. She’d had sex with at least one other person, but she wouldn’t have sex with me. I realized that there were ways a girl could have lost her virginity that might not have been positive experiences. I hesitated, concerned that maybe she had been raped or molested.

“Did something bad happen?” I asked her, genuinely concerned.

“No, “ she said, “It was great. I love sex. But, you’re right, I only want to do it with you if we really are in love.”

“Wait, so you did it with some other guy, but you won’t do it with me?” I asked, trying to understand the situation.

“That’s right,” she said, offering no further explanation. Well, that pissed me off. What the fuck was wrong with me?

“Don’t get mad,” she said, sensing what I was feeling. “If you love me, you’ll be happy to wait for me to believe you and to love you back.”

“Did you do it more than once?” I asked.

“I don’t really want to talk about it, but yes, we did,” she replied.

“Did you do it with more than one guy?” I asked.

“No, Doug,” she replied looking forlorn, “Just with one guy.”

“When was this?” I asked, starting to pry into her personal history.

“You’re not going to stop asking me about this, are you?” she asked, staring at me with a strange look on her face.

“Probably not,” I admitted.

She let out a long sigh, then told me as much as she was willing to share. She had been in love with this guy for a long time. He was older and no longer in high school. I assumed he was in the military, as it was a common thing for some young GI to seduce a high school girl.

For a long time, she had a crush on him but didn’t think he was interested in her at all. Then one day, he confessed to her that he loved her and they started kissing. One thing led to another, and they had sex. He would pick her up every day after school, and they would go to his place and have sex. Then her father found out and threatened to have him arrested for having sex with an underage girl. They stopped seeing each other. Word got out at her school about it and to make a clean start, her dad moved to their neighborhood, and that’s when we met.

“So, I like you,” she told me. “I could love you. I want to be sure that you love me before I give my heart to you. If you get my heart, you get all of me. So, when I believe you love me and I love you back, I will happily have sex with you. Until then, we can dry hump, if you want?”

“It’s like having sex, but we have our clothes on. You put yourself in the same position, and we move like we’re doing it. But, we just kind of grind and rub against each other.”

“Would you enjoy doing that?” I asked, nervously. I was pretty sure I would.

She nodded, blushing.

And so that became our new ritual. We’d make out, then “dry hump.” Every day, I’d profess my love, and she’d challenge me for why. My answers were never good enough. I didn’t know what she wanted to hear. I gave her every fucking answer I could think of. You’re smart. Nope. You’re sexy. Nope. You have a kind heart. Nope. You’re great at dry humping. No.

One day, while her Dad was away on deployment for two weeks, she let me come over to her house. Her mother and father were divorced, so there was no parent around. I thought maybe this would be the day. Nope.

Her sister Wendy was there. Wendy was twenty-two and worked at a local grocery store. She looked so much like Doreen it was scary. She was a little thicker, with even bigger boobs, which I found hard to believe. The most significant difference was her hair was a dark brown compared to Doreen’s blonde waves. She was not terribly friendly to me. At one point, Doreen excused herself for a few minutes and went to her room, leaving me with her sister. During that time, Wendy started interrogating me.

“How long have you been seeing my sister?”

“Three months.”

“You boyfriend and girlfriend?”

“Yeah, we are.”

“Really? That’s weird. You guys have sex yet?”

“What?”

“That’s a no.”

“Uh, no we haven’t.”

“I already figured that out. You’re not so smart, are you? You know she’s not a virgin?”

“Uh, yeah. I know.”

“Did she tell you who she did it with?”

“Yeah, some older guy from where you used to live.”

“That’s all she told you?”

“Yeah, more or less.”

“She told me you’re brilliant.”

“I do ok.”

“Apparently not.”

Doreen came back in the room, looking nervous or upset about something. “What have you guys been talking about?” she asked.

“Oh, Doug and I were just getting to know each other,” Wendy said, smiling. “He has a lot he would like to know about my baby sister.”

Wendy stepped over to me and took my hand, pulling me to my feet. “Doug, I’m sorry, but you have to go home.”

“Oh, is something wrong?” I asked. Wendy chuckled.

“No, nothing is wrong,” Doreen explained. “I just was talking to Pastor Mike, and he needs me to come down to the church to help with a Bible Study Day Care. I said I would.”

“Oh, ok,” I hated to interfere with her religious duties. I was not religious, but I knew some people were.

We walked to the door and realized it was pouring rain. “Shit, I’ll be soaked by the time I get home.”

“Hold up,” Wendy said, grabbing her keys, “I’ll give you a ride home.”

“No, he only lives one street over,” Doreen explained to her sister. “He can run. He won’t get that wet.”

I didn’t like that Doreen was deciding for me and sending me out into a downpour when her sister was graciously offering to drive me. What the hell?

“No, it’s cool,” I said, ignoring Doreen’s suggestion. “I’d appreciate a ride.”

“Let’s go,” Wendy said and headed through the house to the garage.

I kissed Doreen, and she hugged me tightly. “Don’t let her seduce you,” Doreen whispered in my ear, “I’d never forgive you if you fucked her.”

“What?” I exclaimed. “I’m just getting a ride from her. Sheesh, Doreen, she’s your sister. I wouldn’t fuck her.”

She nodded. “Okay. I don’t trust her.”

“Come on, goddamit!” Wendy shouted from the garage. I kissed Doreen again, then left and joined Wendy for the short ride around the block. We got in the car, and as she pulled out of the driveway, I said, “Turn right, I’m just around the corner.”

Instead, she went left. “Uh, Wendy, I live that way.”

“Yeah, we can’t go that way. We’ll go around.”

She could go the way I told her. She would have to go out on the main highway and make a U-turn, and a left across the traffic. I guess she didn’t want to do that. So, instead, we would drive the long way around the neighborhood and come to my house by surface streets.

The drive was awkward and uncomfortable. Finally, we arrived on my street at the far end. It was a long street, but I’d be home in two minutes and couldn’t wait to get out of the stifling car.

“You’re in love with her aren’t you,” Wendy asked, but it was more of a statement than a question.

“Yeah, I am,” I admitted.

“But she doesn’t love you,” she said. Again, it sounded like a statement.

“Not yet,” I said, “I’m working on it.”

“You’re an idiot,” she said, matter-of-factly. “You just like playing with her 38DD boobs. At least she hasn’t let you fuck her yet. There’s hope for you, yet.”

“What do you mean?” I asked, very confused by her comments and the relationship she and Doreen seemed to have.

Wendy sat there staring at me with this look on her face that was hard to read. I felt she wanted to say more, but was trying to decide what to do. After a long, pregnant pause, she shrugged, turned away and said, “You’ll figure it out sooner or later.”

I went inside, left with an uncomfortable feeling. Maybe I had led a sheltered life to that point. I had not accumulated the baggage from years of hurt, pain, and betrayal that many people seemed to attract. I was naive. I trusted and believed people at face value. So, Wendy’s comments and demeanor were extremely confusing to my innocent, young sensitivities.

The next day after school, I got a big surprise. When we arrived at my house, instead of making out in the family room, like always, she asked me where my bedroom was. I pointed down the hallway. Doreen took my hand and guided me toward my room, saying, “Show me.”

We went in, and she closed and locked my door. Nobody was home at that time of day. There never was. My dad worked until midnight every night, and my mother didn’t get home until six, sometimes later. The only person who might come in was my sister, but she was always doing something and never bothered us. So, for Doreen to be so secretive was exciting and hinted at good things to come.

I put on some music, and we sat on my bed. I was more nervous than usual. Doreen took the initiative and kissed me. We started making out, and as things got hot, she sat up suddenly and declared, “Ok, so today, we’re going to dry hump. Do you want to do it in our underwear?”

I stared at her in disbelief. Did she say what I thought she said? I nodded with a shit-eating grin on my face.

Doreen stood up, kicking off her shoes and simultaneously pulling her sweater up. It happened very fast, but to me, she seemed to be moving in slow motion. I saw her belly button appear, then the pale white skin of her tummy, the floral bra cups covering her large, thick, beautiful breasts. Then it was off, and she was shaking out her long, wavy blonde locks. I had forgotten to breathe.

She unbuckled her wide leather belt, then slid her jeans down, revealing small panties with a floral print that matched her bra. She glanced at me, noticed I hadn’t moved and stopped, with her jeans just above her knees. “Are you going to strip too or are you just going to watch me?” she asked, laughing softly.

I jumped up, and within seconds I was down to my boxers. It was all I could do to keep my obvious arousal from poking through the hole. I had to rotate the shorts on my hips to move the hole away from the front. Doreen pulled me into a standing hug, and it was the first time I’d felt her smooth body against mine. She felt incredibly warm.

We kissed and fell onto the bed. Doreen guided me, knowingly, into the proper position and told me what to do. It was incredible. If dry humping her was this good, I could not imagine how much better actual sex would eventually be. I want to say that it went on for a long time, but that would be a lie. It ended very quickly and very abruptly, and quite messily.

I was embarrassed, but Doreen just clung to me and kissed me. She told me I had done excellent and that each time it would last longer. As I lay with my face, pressed to her bosom, I felt her draw in a long breath.

“Do you still love me?” she asked, very softly.

I raised my head and looked deeply into her beautiful eyes.

“I do,” I said with firm determination.

“Why?” she asked, biting her lip.

This was like torture. I’d wracked my brain for weeks and struggled to try to find an answer that would prove to Doreen I loved her. What was it about her that made me love her? It couldn’t be anything superficial; I’d tried all of those reasons. It had to be real. It had to be something that was unique about her and nobody else. I laid there, thinking and asking myself why I loved her.

“I love you,” I said tentatively, as the words seemed to form on their own, “ because you are,” I paused. Doreen was looking at me expectantly, appearing almost hopeful. “Because you are ... who you are.”

I cursed myself for being an idiot. That had to be the dumbest reason I’d ever given her. Of course, she was who she was. Who else would she be? I felt myself slumping with disappointment when her lips curled up at the edges, and her eyes lit up. Her smile got bigger and bigger, until she finally spoke, saying, “Now I believe you.”

Doreen kissed me passionately and for the first time, didn’t stop me as I undid her bra. She only became more impassioned. Doreen didn’t complain or deny me as I moved to second base and third base. Finally, as I neared home plate, she stopped me.

“Do you have any condoms?” she asked breathlessly.

“Uh, no,” I answered sluggishly, having a hard time thinking straight. “I don’t have any.”

Why would I need condoms? I was a virgin.

She sat up and started getting dressed. “Ok, well, we have to stop. We can’t do it without a rubber. Do you have access to any?”

“Uh, no,” I said, feeling huge disappointment. “I don’t think so.”

She had her underwear back on and was pulling up her jeans. “Ok, so tomorrow, let’s go to my house. My dad is out of town for the next couple of weeks. We can be alone there. I have some condoms we can use.”

“Oh, so we’re not going to do it today?” I asked, stating the obvious.

“No, baby,” she said as she pulled her sweater back on. “I have to go. It’s much later than I realized and I have to go to Church.”