Chapter 1: Life as a Digital Native

High school was a bust as far as I was concerned. You’d think that in four years I could have gotten laid at least once. My grandfather got more sex as a teen in the ‘60s than I did now. My parents, the great Xennials—sort of GenX and sort of Millenial—practically invented the terms ‘hookup’ and ‘FWB’. My generation was likely to die virgins if high school was any indication.

“It’s not that I don’t want to have sex,” Jasmine once told me. “Just not ... you know ... in person.” Such is life.

So how do we deal with the hornies? Oh, we’ve still got them. My generation is as horny as any of the old toads in my grandparents’ or parents’ generation.

“I got so turned on during the movie,” Jasmine continued. “I’m going straight home and rub one off. You should do the same.”

I did. You see, we have something neither my father or grandfather had. We are digital natives. We have the Internet. Porn flows as freely into my bedroom as gin flows into my grandmother. And if we can’t find a site that has what we want, we have each other.

“We could Skype when we get home if you’d like to watch,” Jasmine whispered. “I’ll put my laptop between my knees if you will.”

Well, hell yeah.

I had nude photos of a dozen of my female classmates on my iPhone. Encrypted and hidden—we’re not dumb. Jasmine was one of my favorites to jack off to. With. Watching her in real time was good for an immense come. For both of us.

Jasmine gave me a deep and passionate kiss when I took her home. My boner was trapped painfully in my jeans as she rubbed against it.

“I’ll be thinking of what your tongue would feel like while you’re watching me pet my snootch,” she breathed just before she closed the door.

I rushed home and headed straight for my bedroom. Skype chimed as soon as I booted my laptop. I connected and saw Jasmine, already naked. She twirled around showing me her bouncing tits and tight ass.

“Like it? Are you still hard?” she asked.

“Yes and yes,” I said, stripping out of my clothes as quickly as I could. “I can practically feel your mouth taking my cock all the way down your throat.” My cock sprang out to greet her as soon as my shorts were down.

“I love your big boner,” she said. “Let’s get in bed and do it. I’m dripping down my thighs.”

We were two miles away from each other, each getting into our own beds with laptops strategically positioned so the camera picked up our genitals. She did have a wet pussy. I had drips of precome beading out my piss hole. I used it to slick my cock and began stroking as I watched her spread her pussy lips and start rubbing her clit.

It didn’t take either of us long.

“Thanks for a great date, Jasmine,” I said as my cock began to wilt.

“Let’s do it again soon,” she responded. “I always get the best comes after we’ve been out.” I closed my laptop and went to sleep.

If you’re my grandfather’s age—or even my father’s—you probably think this is all super frustrating. You’re wrong. In spite of not having put my cock in a girl, I’d had sex with several. I knew Jasmine would be stroking another one off in the morning while she watched Derek’s morning wood. In fact, Dee had told me to call at exactly nine Saturday morning to help ‘get my vibrator started.’ I didn’t think Dee ever actually got wet when she used that thing, but I was sure she got off. I sure did.

And it wasn’t like we were cheating on anyone. We usually went out as a group and only paired up for a little kissy face. We hardly touched otherwise. Dee has huge tits and I did feel her up one night. I couldn’t believe how heavy and squishy they were. But otherwise, you know, no one was actually having sex with anyone else. We had our smartphones and laptops.

When I was twelve, I started figuring out how my equipment worked. When I was fifteen, I convinced my dad to let me get a lock on my bedroom door so Mom would quit walking in on me. She caught me masturbating once when I was fourteen and dragged me out of my room to make me go wash my hands with anti-bacterial soap. She’d been doing that for years, whenever she saw me touch something she thought was dirty. That included other people. I wasn’t sure how I’d ever been conceived.

So, what’s it mean to be a digital native?

The day I got home from the hospital, I was placed in a crib with a digital monitor nearby. Not one of those speaker things that lets a parent in a different room hear the baby cry. This was full video linked to my father’s PC at work and my mother’s laptop in the kitchen. Neither one of them accomplished anything for four weeks after I was born. They just sat and watched my babyness on their computers. Why didn’t they just sit in my room and watch me? They didn’t want to invade my privacy at such a young age.

I learned my ABCs watching YouTube videos on my computer. By the age of ten, I had my own iPhone. And I saw Kelly O’Rourke’s bare breast on webcam the day she turned fifteen. All my homework through high school has been emailed to my teacher. My parents own a huge collection of music CDs. They have a clunky old player they put them in when they want to listen. All my music is in the cloud. I don’t buy ten songs I’m not interested in for one song I like. I plug earbuds in when I want to listen and don’t bother anyone else when I choose what I want to hear. I’ve got a laptop computer on my desk at home, but most of the time just use my iPad. It’s smaller and lighter and I can type 50 words a minute. With my thumbs.

Sometimes, my friends and I get together on the weekend to play a game. We all log in and choose up sides. If we need another player, we can usually find one pretty quickly online. I’ve got more online friends than IRL friends. I’ve got about 50,000 photos and videos in my library and I post hundreds of them online for my friends. I send and receive over 15,000 text messages a month.

Digital native.

So, it always surprises my friends when I log onto a chat session or answer a Skype and I’m standing there in my underwear with a brush full of paint in my hand and an easel beside me.

“Yuck, man! Why aren’t you doing that on a computer?” Rick asked.

“Your mom will kill you if you get any of that on the floor!” Charmaine laughs. She knows my mom. I have to stop and point the camera down at the newspaper I’ve got spread all over the floor.

“I’ll give you twenty dollars for your tightie-whities if you’ll paint them while you’re wearing them,” Kelly adds. She is one twisted girl. I put a red swirl on my right butt cheek. I buy jockey shorts at K-Mart for painting in. None of them ever see the washing machine. My mom...

I like paint. I guess in some ways it is my way of rebelling. Even if I’m chatting with my friends, I’m doing something non-digital. Like Rick should talk. He actually goes outside and plays baseball. Damn good at it, too. Jasmine has her Barbie dolls. Charmaine collects Pokemon. The cards, not the virtual game, though she does that, too. Kelly collects my painted underwear. Go figure.

The first time I picked up a pencil in pre-school, there was something magical about it. There was a physical response to a physical action. I could hold my primitive drawing in my hands. There was nothing to click to close it. If I wanted to get rid of the paper, I had to find a recycling bin.

So, I suppose you’re wondering where I get newspaper to spread under my easel. Grandpa, my father’s father, gets one delivered every day. Once a week, I go by and collect the bundle. I asked him why he didn’t just read the news on the computer. He grinned and asked me why I didn’t paint pictures on the computer. Touché. Grandma rolled her eyes and he poured her another gin and tonic.

I collect his newspapers and spread them out under my easel. As soon as I finish painting, I hang my underpants in an empty part of my closet and clean my room. I make sure all the papers are picked up, folded neatly, and taken to the recycling bins. I take a shower and make sure I’ve scrubbed all the paint off my body. Sometimes the red I used on my underwear bleeds through the fabric. I shampoo, rinse, and repeat.