He simply left his clothes behind...
“It’s always so deserted out there, you know,” Janice said. “And I always feel so naughty doing it, too.”
“Yeah,” I replied.
My best friend Janice had just told me that she snuck out of her house at night to explore our neighborhood.
“Of course, since it’s getting colder outside, we can’t go exploring outside much more this year.”
She appeared to concede this point, although I sensed some hesitation there.
“Hey, you wanna go out this Saturday night? You know, explore together?”
I looked up at her. “You sure?”
“Well, yeah, you’re my best friend. Why wouldn’t we?”
“Okay. One AM good?”
I was certainly surprised that Janice wanted to streak the neighborhood this weekend. At first I was surprised that she admitted it—she was the stereotypical “good girl,” always getting A’s and B's in school, never in trouble. I don’t think I’d ever seen her out of her school uniform, which was very conservative (read: didn’t show any skin). She always put homework before anything else, and didn’t have many friends. In fact, that’s why our parents decided to have us hang together.
I wasn’t exactly a troublemaker, but I didn’t always follow the rules. I’d been yelled at more than a few times for coming home after my 9PM curfew, and my grades were always in the C range. My parents thought it would be a good idea for me to hang out with Janice in the hopes that I would pick up some of her habits, and her parents wanted her to socialize outside of school more.
The “streaking” I had done started when I was 16. I was lying in bed watching the clock tick later and later when I got the idea in my head that a walk would help me sleep. I batted the idea around for a while before I just decided: if I was still awake by one in the morning, I would go on my walk; otherwise, I would just forget it.
As it had turned out, 1AM passed, and I was still awake. I climbed out of bed and started rummaging for clothes by the light of the closet when I had another thought: no one would be out this early, right? Why not forget the clothes? I sat back on the bed, feeling my dick get hard at the thought.
Finally, I decided that I would do it if the temperature was at least 60 degrees. I clicked my phone on and saw the temperature in the upper right corner of my screen: 63.
“That settles that,” I said, stripping my underwear in one fluid motion. I found my keys and clipped them to a Navy lanyard I got from school; it’s amazing how much free stuff employers give away for free. I grabbed a small flashlight and made my move.
The way my family’s house was set up, my bedroom was off by itself. My parents had a room upstairs, and my sister was near there. My room was designed to be an office, but my parents turned it into a bedroom instead. I would pass through the living room and be able to walk out the front door without anyone knowing.
I moved through swiftly and silently, taking a full minute to exit the door—an action that takes me less than five seconds when I don’t care about noise. That full minute allows me to unlock the deadbolt, ease the door back open, slip out, close the door, and re-lock the deadbolt.
Once I did that, I was standing on the concrete stoop, feeling the concrete beneath my bare feet. There was a slight breeze, and I felt that all over my nude form. I padded down the walkway, then down the driveway to the street, feeling my rock-hard cock bouncing with every step. I found that I didn’t really need the flashlight; the full moon hung fat in the sky, guiding my way.
I decided to head east, away from the highway. Even at this distance—easily half a mile—I could see traffic streaming by and knew it was too busy for a naked teenager to stumble upon. Most of the lights from the houses were off, but I knew I had to make sure to avoid the burning lights; if I went near those, it meant I could be seen.
My first excursion wasn’t too big of a walk. I went to the end of Maple, then turned onto Oak Avenue and walked until I got to Pine Street, before I turned back and went home. But it was huge for me; every step, I could feel my heart thumping in my chest, and I kept expecting something to go wrong.
When I got back to my house, I crept into the backyard and jacked next to the grill. I think I literally rubbed myself ten times before shooting in the tall grass. I snuck back inside and lay awake for another thirty or forty minutes, exhilaration coursing through my veins, and a smile on my face.
I kept up my streaking on a fairly regular basis. There were nights that I would stay up all night because I was streaking the neighborhood, and there were nights I went out once. Of course, most nights I didn’t even bother with it; how else would I explain my lack of sleep the next morning?
When it became colder out there, I didn’t streak as much. But the following March, I was back on the streets, making up for lost time. I also found ways to expand; by the time Janice confessed her late-night exploits, I had been streaking three neighborhoods and had even ventured to a few feet from the highway.
When I was 15, my parents had a pool and a hot tub installed in our backyard. Soon after I started streaking, my late-night exploits included skinny-dipping and soaking in the hot tub. I actually continued sneaking outside past winter to soak.
Janice and I had agreed to meet up on the 21st of May, early Monday. We agreed that it would be less likely people would be out and about in the early morning hours of a Monday. To ensure I was prepared for it, I held off on my exploration the week before.
Finally, Sunday rolled around. I made sure I was well-rested and I had some Monster stowed away to be sure. My parents sent me to bed at ten, but I kept myself up reading sci-fi magazines and jerking. Finally, 12:40 rolled around, and I snuck out of bed. I picked up the bag I had prepared—snack junk, Monsters, soda, and a blanket—and my usual stuff and snuck out the door.
I had been doing this for so long, and I had just beaten off, so my dick was limp when I walked down the driveway and followed Maple to Yew Street. I walked the path I had memorized when I was 10, and stopped outside Janice’s house for the first time since I started streaking. I checked my watch: 12:55. I buried myself in a bush just off her driveway and waited.
After a few minutes passed, I heard a door close and saw Janice coming down the driveway. She was fully clothed, although not in her uniform. Shit.
She walked to the bushes and started looking around. I decided the best thing to do was explain, and I poked my head out.
“Hey. You ready?”
“Not quite,” I replied. “I think there was a little misunderstanding.”
“What misunderstanding?” she asked.
I took a deep breath and walked the rest of the way out. To my surprise, Janice held her hand to her mouth, and I could distinctly hear her laughing.
I nodded. “All my exploits, I snuck out naked. I didn’t mention it because that’s what I thought you were doing.”
“Oh my God!” She was still laughing.
“Do you want me to go back for some clothes?”
She shrugged. “I’ve already seen it; there’s no point now.”
“Okay, so let’s go.”
We had agreed to go to a nearby public park, which had been the center of Janice’s exploration. We were just going to hang out there, eat some snacks, and marvel at our boldness. We talked as we walked, keeping the same hushed tones we used in front of her house, and soon it seemed like she forgot I wasn’t wearing clothes.
When we turned onto Willow Avenue, she paused. “Hold on a second. I feel bad that you aren’t wearing anything, and I’m fully dressed.” She dropped her bag and took off her shirt. After a moment’s hesitation, she also unclasped her bra; her nipples instantly became hard points in the cool air as she stowed her clothes in her bag. She moved near me and clasped my hand as we walked.
Finally, we saw the storage complex, and then the park. The park was a good fifteen acres, and a lot of open space. Five small shelters and two large ones dotted the property. There was some light, but no one was out here using it this early. I checked my watch again: 1:30.
We ducked into a small shelter where I spread out the blanket as Janice took some food out of her bag. She had smuggled a bag of fifteen cookies out, as well as some soda. I thought I even saw a radio in there.
“So tell me, does my body look like what you thought a naked boy would look like?” I asked.
She shrugged. “Not really. I mean, I’ve seen porn—”
I gasped in fake-horror. “Pervert!”
We laughed a bit before she pressed on. “I’ve seen some pictures where the guy’s totally shaved. And then I see you, and you’ve never even had a shave.”
I had to concede this.
“So, does it look bad, or good?”
“It doesn’t really matter, you know? I mean, the shaved guys look bigger, but I guess that’s part of the illusion, then.”
“Okay, let me ask you this: do you shave?”
She gave me a weird look. “How do you know I have hair down there?”
“You’re not the only one who looks at porn.”
She did a faux gasp. “Pervert,” and we laughed again. Then she stood up and pulled her shorts and panties down, kicking them to her bag.
Her pussy lips were puffy and remarkably bare. As I looked, I realized I didn’t even see a point on her abdomen where her stomach flared out, like I had.
We sat there chatting for a while. The next time I looked at my watch, almost another hour had passed by. Right after I checked the time, she brought up a bombshell.
“Have you ever had sex?”
She scoffed. “As if. You know how controlling my parents are. I’m their little perfect princess, yet I’ve never even been on a real date. This is as close as I’ve gotten.”
She nodded. “At least I know I turn you on.” She pointed with her foot. I looked, only half-surprised to see my cock standing on end again. When I raised my gaze, I saw her shaved slit oozing clear juices.
“Same here,” I said, pointing.
“That’s different. I’ve had a crush on you for a while, but, like I said, my parents wouldn’t let me act on it.”
“Really?” I had never really had any thoughts about any girls, but I always had the urge to find a way to spend more time with Janice.
She smiled, and I saw a blush cross her face in the faint light. I smiled as she crossed the space and pressed her lips to mine. We kissed for at least a full minute, our hands roaming our nude bodies. As we kissed, she pulled me on top of her, and I felt the tip of my dick suddenly enter a warm, wet, honey pot.
I may have been a virgin, but I was not completely stupid about sex. I looked her in the eyes. “You sure?”
She nodded. “Make me a woman.”
I started pushing into her slowly, pausing when her breathing began to intensify. I was nearly halfway in when I encountered a wall of flesh.
“Pop my cherry for me,” she said. I humped against her several times, always stopping at her hymen, before I took a breath and pushed in all the way, feeling the flimsy wall of skin give way to my invading cockhead.
To her credit, she didn’t scream. She clutched my back harder, and I heard her breathing heavier, so I lay there, now completely balls-deep in her and waited. “Ready?”
She nodded, and I began thrusting. I could feel her pussy pressing down on my cock as it slid in and out, in and out, in and out. It was easily a hundred times better than jerking it, and the groans I was getting from Janice told me she enjoyed it, too.
Of course, since it was my first time, I didn’t last very long. Five minutes after I started, I felt it start to pulse inside her, and I held it there, giving her a long kiss as it deposited the last of my seed. But I never went soft; I kept thrusting inside her and managed to get her to squirt before my second load came in.
Janice walked home nude with me that night when we left at about three in the morning. Since then, we do our explorations together, and both of us leave nude now. We’re still having sex, too. In fact, Janice told me she’s been on the pill since she was 16, to regulate her periods, so we’ve been going bareback every time.
It’s November now, and too cold to streak outside. But that’s okay, because I’m getting ready to leave my house now. I’ll be wearing a long coat, shoes and socks, and nothing else. Janice invited me over to her house, and her new basement bedroom, complete with a door outside. I can’t wait to try sex in a real bed.
Author's note: This is the first story I've posted online anywhere. I do appreciate honest feedback, but please no flames.