Chapter 1

In the summer of 2005, I first saw the movie preview for "The 40 Year Old Virgin."

Even though I was only 20 years old at the time, let's just say that it hit a bit too close to home.

Getting a girlfriend was something that happened to ... other people.

Not me.

Finally getting a girl, let alone actually having sex, was a pipe dream stacked on top of another pipe dream.

But that stupid movie inspired me to actually grow a pair. I was not going to end up a 40-year-old virgin!

I had to reverse my fortunes.

I got some industrial grade acne medication to clear my face.

I tried looking people in the eye more often, and along with that, actually speaking to humans more often.

I also found out people thought I was kind of funny. Who knew?

The hardest thing, though, was running and lifting weights. The entire concept was totally antithetical to my nerdy "I hate jocks" persona that I had cultivated my entire life. But, I stuck with it - and actually kind of enjoyed it.

Again, who knew?

Six months into my transformative vow, I finally landed Beth.

I met Beth in our college creative writing class in the spring of 2006. We began getting close, bonding over movies, writing, and all that artistic junk that literature majors like us held dear.

In quite awkward fashion, we hooked up. But, neither of us could admit that that was our ulterior motive.

We got an idea to work on a collaborative story. It was about a young elf (me) and a regal forest nymph (her). They were seeking to recapture some MacGuffin device from an evil wizard.

Truth be told, the story was utter shit. Just a cheesy "Lord of the Rings" rip-off. All you need to know, though, was that the whole "story" was just a ruse that allowed us to hook up with each other, after which we promptly abandoned our story.

Like me, Beth was a virgin. Technically.

It's complicated. It's a long story. It truly is.

She was a bigger girl and I thought she was kind of cute. She had a great smile and was curvy in all the right places. And good lord, the girl was seriously stacked like a never-ending game of Jenga. But unless she wore a tight top (which she never did), she wasn't the kind of girl that would actually get looks from passersby walking down the street.

We were two birds of a feather like that. Nobody would notice either of us. Except for the stacked thing. I wasn't stacked.

See? I told you I was funny.

But Beth seemed to actually like me. That sort of thing didn't happen often. Ever.

By summertime, we were in the midst of a truly virginal courtship worthy of balloons, puppy dogs, and pretty pink flowers.

I didn't push the sex thing on her. It just wasn't the thing to do. Again, it was a long story.

But mercifully, about three months into the relationship, she finally let me.

Our first time having sex was a blur. All that buildup ... for that?

It was quiet, after-school-special copulation. Very awkward. Confusing. I had no idea what I was doing. I barely knew where to put it. Neither did she.

Even though she was way older than me at age 26, she was a virgin, too.

And sex frightened her.

Luckily, it frightened me less. I was strangely confident in the bedroom. It was the damndest thing. It was so unlike real life, where everybody else frightened me. I guess, since I already got the girl, why get nervous? As such, it only made sense that I would take the lead in our sexual relationship.

That's what led to me heading to the bookstore to find a book. A how-to book. I needed to learn how to do this stuff.

It was this stupid trip to the stupid bookstore that changed my life forever.

Beth happened to work at this particular bookstore, so it made it difficult to sneak in and procure a sexual instructional manual. I had to go prospecting for "Kama Sutra" knockoffs on the down low.

I was quite nervous while looking in the sex section at the bookstore. I was worried somebody would see me. Honestly, I was worried that Beth's co-workers, who knew that I was her boyfriend, would see me, report back to her, and tell her that I was some pervert messing around in the sex section. I have no idea why I was nervous about that. Sex is a normal adult subject. But with Beth, it was, I don't know ... not normal.

I found an older paperback there and began thumbing through it. It was called "A Sensuous Man." It was written like an instructional manual. It was, essentially, just what I needed. It was graphic, talking in detail about pleasure zones, cunnilingus, and all of the other taboo subjects that we just weren't told about in the dark ages of the early 21st century.

The approach taken in the book put me at ease.

Beth needed this. To enjoy sex. To not be scared. I wasn't scared. I just didn't know what to do. I just wanted her to feel good. To relax. I didn't want her to be the frozen, scared plank she was. Somebody had to lead this.

As I pondered this, previewing the book with rapt attention, a sweet, sing-songy voice broke my concentration.

"Sir, are you finding everything okay?"

I was startled and instantly froze. I felt a harrowing and fearful chill burrow its way up my spine and slap me in the back of my head, like I just got caught with my hand in the cookie jar. I looked up from the book to see a mind-bogglingly gorgeous girl.

I knew I was taken by Beth. But I wasn't dead.

She wore a pair of black, wire-rim glasses and her lips just shined. They were bright pink and glossed up, begging you to notice them, which I did. She bit her lip as she looked at me, a move that always made my pulse quicken.

My eyes glanced downward, looking at her nametag on her green bookstore polo, perched atop a pretty staggeringly large swell of breasts for an otherwise slim girl.

"Zoey" it said.

Most men could've cycled through that reaction in a matter of seconds. But for me, armed with my magnificent social anxiety, it spanned 10 truly long seconds of staring silence. It was a long time to be quiet after somebody asked a question.

Throughout this torturous span, I saw her expression change three times.

After biting her lip with an almost innocent stare, she transitioned to a raised eyebrow as she waited for a reaction. Then, she produced a more relaxed giggle as she seemed to look me up and down. Then she smiled.

Big.

I was startled at the realization. Was she checking me out? I wasn't sure that had ever happened before. I wasn't the kind of guy that actually got checked out.

I finally stammered out some words.

"I ... uh, I'm just, um ... browsing." I quickly closed my book and, without looking, tried to nonchalantly place it back on the shelf without her noticing.

"Are you sure there's not anything I could help you with?" Zoey asked, arching her eyebrow. She looked down again at me then back into my eyes, letting a little giggle escape her lips. I don't know why I thought this, but it seemed like her giggle was ... scripted and not spontaneous. It's just something I noticed. Or pondered.

She had her hands behind her back and stretched slightly, arching her back, which had the effect of stretching her bookstore polo shirt out even more across her chest.

And I noticed. And looked. It occurred to me that if I pretended to be reading her nametag - which I had already read - I could get away with looking at her chest a second or two longer.

I looked back down at her and into her eyes, which were blue and big like an anime girl. They were the biggest, most shimmering pair of eyes I'd ever looked into.

Then, a rush of thoughts entered me.

Unlike my last journey inside my own head, all these thoughts and actions took only a few seconds, but they were vivid. I was suffering from sensory overload.

One thing I wasn't suffering from: Any thoughts at all of Beth and our sex life.

"I'm- uh, I'm fine. Like I said, I'm just browsing."

I twisted my elbow to place my book back on the shelf behind me while not ripping my eyes away from her. Success! Now nobody would know...

Then, proudly, she just reached behind me, right for the book I had put down. She picked it up, looked at it, then back up to me, glaring above her glasses with her shimmering eyes, her expression overflowing with playful judgment. She pinched her face in a cute frown before losing her resolve and letting it descend upward into a knowing smirk.

"Hmmm..." she said inquisitively as she lightly tapped the closed book against her palm, like she was going to punish me or something. I was frozen, scared to death. Despite those nerves, I kept glancing down. And I kept seeing her stupid tits staring at me. I kept yo-yoing back and forth from her body to her eyes, but couldn't bear to actually look in her eyes.

"Books are a good start," she said, still smirking. She took a half-step toward me. My nerves were blazing and I felt like my heart would beat out of my chest. Then, she leaned in toward my shoulder. I kept panicking.

"Don't tell my boss I said this," she said in a whisper, looking away from me. "But books can't match ... life experience."

She stood up straight again and looked at me daringly. Her gaze was completely unwavering, like she was looking through my eyes and into my fucking soul.

Little by little, she began moving closer to me. She came closer to my face, like she was going to kiss me. Her smile disappeared and she looked like she was going to eat me. Devour me. I'd never seen somebody look at me like that in my life.

And say what you will, but it was fucking scary!

I felt like I had to return her gaze. I had to look her in her eyes, too. It was like a game of chicken.

So, I looked into her way-too-pretty eyes, absolutely mortified.

I had no idea what my body language was saying at that point. I just looked into her eyes. That's all I focused on, centering my every muscle to my eye sockets so I could look straight ahead at her. Her baby blue anime eyes were glistening white under the lights from the ceiling the bookstore, almost like they were painted on.

And she just kept looking. And moving closer. Daring me. She wouldn't let it go. Her protruding breasts began to make contact with my chest. This went on for 10 of the longest seconds of my life ... and 10 of the most intense and exciting seconds of my life.

She finally softened her gaze, backing up slightly before she produced a smile.

"You're cute," she proudly announced with an innocent grin and a tilted head, like she suddenly came to this conclusion after scrutinizing my face. "Your eyes are gorgeous. I bet you'd have no problem attaining ... life experience." She glanced down and smiled a toothy grin behind her shiny pink lips. "Yep, no problem at all."

And then she bit her lip. Again. AUUGGGH!

She quickly backed up, turned around, and while walking away, said, "If you need any more help, sir, I'm Zoey. Just look for me." She bounced away like a fucking bubbly teenager.

I looked down as she left, and then I saw it.

A tent was protruding from my pants. Clear as fucking day.

Was I that obvious? Did I have that big of a hard-on while she was talking to me? Daring me?

I felt as if I somehow avoided death. I readjusted my treasonous cock behind the waistband of my underwear and practically ran to the restroom.

I went to the sink, still hard, and splashed water on my face, looking at myself, replaying the conversation in my head.

Then I looked at myself. I mean, really looked, like I was looking with somebody else's eyes.

Was this me?

My face was clear. No more pimples. My face was smooth and free of blemishes, since that acne medicine worked like a charm. That little gut I always had was gone. All that running and lifting had done me good. When I noticed I had abs a few months before, all I realized was that my paunch was gone. But I never really thought about it and noticed.

My hair was sitting in a way that was messed up, but looked good somehow. I never gave it credit before, but I suppose I had nice hair. And my eyes kind of jumped off my face. I mean, I looked at myself in the mirror every day, but I guess my eyes are the first thing I notice about myself. So it's the first thing everybody else notices, right?

Obviously Zoey noticed.

Wow, I wasn't ugly.

Then, I reflected on Zoey and what she said to me. How she was looking at me. And I absolutely beamed with pride. I'd never experienced anything like that before in my life. I've heard forever about "love at first sight" and that must have been what they were talking about - that experience I just had with Zoey.

Even with that thought about Beth, I grabbed at my still rock-hard cock. I felt it twitching along with my heartbeat, and I saw Zoey in my mind's eye.

I couldn't help it. She was so damned attractive. I couldn't even use the word "hot" because, from the way she spun a phrase, she was definitely smart. She was better than "hot." She seemed like she could keep up with me. I'm not brilliant, but I hated having to dumb down my average vocabulary when I talked to people. If she and I were on a date, she could easily keep up.

I went to the bathroom stall to gather my wits and the first thing I noticed was my tent. I felt the torque from my pants and boxers being stretched out and pushing back into it.

I don't know what moved me, but I suddenly unzipped and pulled my cock out and looked at it.

I started beating off, right there in the bathroom stall. At my girlfriend's place of employment. Thinking about one of her co-workers. I just simply didn't give a single fuck.

I stroked my cock like a madman, dry-handed, and despite the rug-burn, it took me only 30 seconds to cum. Tops.

I breathed raggedly as my cum splashed on the door of the stall like I was shooting a fucking water gun against it.

I never came like that in my life.

The time is right, I suppose, to tell you why Beth was all weird about sex.

When we first started dating, she said she had a secret.

She told me that she wasn't really a virgin.

She told me that her birth father had brought her into some religious cult where he and his friends ritualistically raped her when she was a child. From the story she told, they were masked, holding torches and raping little girls. Or at least that was the image that was seared into my mind from her harrowing tale.

It was, obviously, a bombshell. I had no idea how to react to that news. Even now, I still don't know how to handle it.

And she doubled down. She said that the experience caused her to have split personalities. Sometimes, she said, she'd fade in and out, acting a different way completely, believing she was somebody else based on the triggers in any given situation. Afterward, she'd have no memory about it when it happened.

I know what you're thinking...

But it wasn't that easy. Actually being in a relationship with somebody who had experienced that, was essentially made crazy by that, it becomes the kind of thing you couldn't simply ignore.

I cared about her. And she was my first girlfriend. It's not like I would get another. I'd marry her eventually. That's what people did, right? So I had to be there for her and work through it, doing what I could to help her deal.

And that meant being sensitive about sex. Because, of all those triggers in her environment that set her off, sex was a major trigger.

It was difficult because I was pretty healthy about sex. I was raised that it wasn't taboo. My dad left his Playboy collection out in the open for bathroom reading. It just wasn't a big deal.

I wanted to explore her body and make her feel good while I made myself feel good and grow together through sex.

But we were so damn awkward about it.

Christ, at that point, we had had sex a total of exactly 6-1/2 times and I hadn't even cum yet while I was with her.

It was a problem.

But, being honest about it, the fact that she was frozen solid during sex, scared to move, scared to do anything or say anything, let alone let herself enjoy it, was probably the problem.

That's why I was so excited when Beth bought a bra the day after my bookstore episode with Zoey. It wasn't like any of the tan granny bras she had. This was a pretty bra. It was honest-to-god lingerie. The good stuff.

It was a symbol to me that, as our sexual relationship began to grow, she was trying.

Her roommate Nikki was staying the night at her parents' place, so we had her apartment all to ourselves. That's when she showed me her cherry red bra that pushed her magnificent tits up and together, framing them perfectly.

I was in heaven.

She was finally letting me have her.

I lifted her sweater over her head and ran my hands over her bra. It was an amazing sight. She was smiling, giggling awkwardly, but seemingly content. She let me lift her bra cups and suckle on her breasts, chewing on her nipples. I lost myself in her. She moaned for the very first time and had a high-pitched, sing-songy squeal whenever I did something she liked, like graze my pointed tongue along her hard, moist and crinkled nipple as it protruded an inch from her chest.

Within a couple minutes, I just took her. Right there on the couch in her living room.

My cock was straining in my shorts and I was grinding against her thigh. And she wasn't pulling away. On occasion, I think I even felt her reciprocate by moving her thigh, ever so slightly, into my humping thrusts as my lips explored her body, trying to put her at ease.

She was still pretty frozen. But she was smiling. Giggling. Moaning.

I fetched a Magnum condom from my bag and slipped it on. Before long, I was rubbing my thick cock head against her clit, and I swear, she jumped with pleasure. At least it seemed like she did. I didn't think it was in my head.

It was finally happening. Though we'd technically had sex several times, this seemed like it would be the first time that we actually fucked like normal people.

Every time we had had sex, getting it in was problematic. She was so tight, negotiating my cock into her seemed to take 30 seconds or more. She'd always complain about pain. She'd often tell me to not move at all, because it hurt whenever I thrust.

But not this time.

She wrapped her arms around my neck as I thrust into her. Fully. I'd withdraw my cock almost completely with each thrust before lunging forward and bottoming out.

This felt good.

I looked into her eyes as I kissed her and she shockingly had a glazed sex look. At least that's what it seemed like. I was new at this. I didn't know.

She had a 1,000-yard stare, off into the distance, enjoying the moment. Feeling everything.

Her voice raised a few octaves as she was moaning in high-pitched mews. She had yet to close her eyes or really return my gaze, looking back into me, which I thought was a good sign. She was focusing on her body. I knew it. Focusing on the pleasure.

At long last, I finally felt it. My balls tightening up. My cock hardened even more. This was it.

Without her roommate in the house, I moaned LOUD.

If I wasn't wearing a rubber, I would've blown a pint of cum into her, which I confirmed when I pulled out and saw a golf-ball sized reservoir of cum swelling the end of the condom.

"Oh my God," she finally said in a high-pitched voice, smiling and, for the first time, showing a look of actual lust in her eyes.

She enjoyed it!

We were both grinning like idiots and in a matter of minutes, we just fell asleep together on the couch, holding each other.

The next morning, Nikki came back to the apartment and told Beth that they needed to talk.

It was a bit of a bomb, but Nikki said that she had been secretly struggling with her finances for months. She was trying to not bother Beth with it, but she was at her breaking point. She couldn't make rent this month and she was moving back in with her parents.

Nikki would be gone within a week.

I offered immediately to move in with Beth. Yes, it was a big move, but I was ready to make it. We were a real deal. Sex the night before had confirmed it.