One Night on the Hill

In my teenage years I fantasized about licking and kissing a girl on her pussy and ass. At the time, I didn't know much about sex and fucking yet. I dated girls occasionally, for dances and the senior prom and the like, but did not have much experience in the lovemaking department. I was shy, but definitely attracted to girls. My ultimate fantasy in my mind would be to arrange to meet a girl, completely nude, in a remote area at night, and lie in the night air while licking and sucking each other. I knew I had little chance of ever realizing this fantasy; after all I didn't even have a steady girlfriend, much less one that would be willing to meet me nude. But I decided I could at least try to fulfill my half of it, and fantasize the other half.

After graduation, most of my classmates and I had already turned 18, but few of us owned cars, lived on our own or had much freedom. I was no exception. I lived with my parents and was looking forward to going away to college in the fall. I had a summer job, but otherwise had a lot of free time. As long as I lived at home, I had to abide by my parents rules, and they didn't like me staying out late. Whenever I did get home late, I was always quizzed about where I was or who I was with. To fulfill my fantasy, I would have to sneak out undetected.

My bedroom was on the second story of our split-level house. I had figured out a way to crank open the hinged window all the way and remove the screen from the inside. I waited for the right night to try sneaking out. There was a rainy warm night in June that seemed perfect. Not that it mattered, but my sister was having one of her friends over for a sleepover. It just seemed to heighten the risk a little – if I got caught I would be embarrassed in front of a neighborhood girl, not just my family. When everyone turned in to bed, I closed my door tightly, stripped down nude, got into bed and waited. I was excited and hard in anticipation of what I planned. I forced myself to wait until after midnight, figuring everybody would be asleep by then. I remembered to leave a towel to dry off when I got back.

To me, the challenge and excitement of my plan were to do it completely nude start to finish – high risk. But no way I wanted to get caught. Fortunately, my window could not be observed from the street or any neighbor's houses. It was shielded from the street by tall juniper trees and yew bushes in the front, and blocked from next door neighbor's view by a large crabapple tree. Right below my window was additional cover provided by tall leafy shrubs.

From my second floor bedroom I would need to climb out backwards so that I could lower myself to the ground, using the bricks and ledge of the window below for toe hold. My room was not really on a full second story. The room below was a basement bedroom with the window at ground level. It was my brother's room and he was not home for the summer. I opened my window completely, quietly removed the screen and lowered it to the floor. The window was right next to the head of my bed. Although I was tall, about 6-5, I was athletic and skinny enough to climb backwards from my bed, reaching first one knee then the other up onto the sill while pushing up off the bed with my arms. Once perched like that facing ass out, I was able to lower one leg down till I found a toe-hold. We had that old English style masonry that had some of the bricks sticking out. Then I lowered my other leg down while holding the window sill. This had to be done carefully and quietly, and I didn't want to injure myself. So there I was, slowly lowering myself to the ground, completely nude and exposed if anyone should walk into our side yard. But once I got to the ground, the shrubs provided cover.

A light gentle rain had been falling most of the evening into the night, and it was still a slight misty rain. It felt good, and the ground was soft on my feet. It was erotically stimulating to walk through the damp bushes and the light rain, and I got rock hard. My goal was to walk all the way to an open grassy area on top of a hill that was part of a cemetery. This was where I would meet my girl in the fantasy.

The distance might have been about a 10 minute walk by street under normal conditions. To provide maximum cover, even on this overcast night, I decided to take a route through the back yards of the houses behind ours. But first I had to cross my own back yard diagonally to the far corner, where I could be seen from a neighbor, or my sister's window. With no lights in any windows, I judged no one was awake. None of the yards had any fences, but generally the back yards were bounded and defined by rows of trees or shrubs. I had a heightened awareness of all the sounds around me, but all I could hear was the barely audible dripping of rain from the branches. Keeping to the darkest areas, I walked cautiously through my yard and three or four back yards, concealed in bushes and out of sight of windows as much as possible. In each yard I stopped before crossing to judge if any lights were on in the house or signs of activity. With no sign of anyone up at that hour, I got bolder as I got farther along, and eventually I made it past the last house. This was the last house on the dead-end street behind ours, and abutted the cemetery property. There I needed to cross an undeveloped parcel that had a few trees in a thin copse for cover. I turned right and made my way through this area, and toward the cemetery proper.

Now was the riskier part – the direct path would have to cross a large open area to get to my ultimate goal, which was a grassy area on top of the cemetery's hill. This was a hillside that had not been developed with graves yet, and the grassy area on top was open and undeveloped as well. To get to the top of the hill, I could walk entirely across the open area, in view of several houses. That seemed too risky when I could take a longer route over to the left through the cemetery itself, which had many trees, shrubs and large monuments for cover if needed.

As I walked my level of excitement increased and I stayed super hard, fantasizing about my goal and delighting in the feeling of the misty rain on my cock. I made my way carefully through the cemetery to the top of the hill. My fantasy girl would have entered from another direction, stripping nude somewhere along the way, and meeting me here. In my fantasy we would lie on a blanket, but tonight I did not think to bring one. So I lay down in the wet grass, face and cock up. I stuck out my tongue, pretending I was licking her pussy while she sat on my face and sucked my hard cock.

I was intensely hard with these thoughts and stimulation, and I masturbated to a powerful orgasm, squirting cum all over my stomach and pubic area. I continued stroking until every drop was out, and I was still hard. I gathered some of the cum in one hand, then I raised my legs and flipped them over my head with my back arched and ass up in the air fully exposed. With that hand I rubbed my cum all over my asshole, imagining my girl was licking and touching me there. With my index finger lubed with my cum, I pushed it gently into my asshole and wiggled it. I fantasized about my girl putting her butt-hole right on my lips while she stimulated my ass and cock. I probably was doing this for no more than a few minutes, but then came back to reality after sucking the cum and ass taste off my finger.

The real hard part was next – fantasy sex over, but I still had to make my way back, nude, hard, and no cover. But the rain and night air felt so good, I enjoyed the walk back and feeling of the cum dripping through my crotch and squishing on my asshole. I was bold and still confident no one was up that would notice me. I pretty much made my way back the same way I came, continually checking for lights and any sign of activity. At the ground below my window I still had the challenge of quietly climbing back in – but it was much easier climbing up and going in head first than it had been going out ass first. I closed the window and would reinstall the screen the next day. I used the towel to dry my hair and most of my body, taking care to leave my crotch and asshole moist with my cum and the rain. I wanted to wake with dried cum as a reminder of what I had accomplished. I was still wound up but gradually drifted to sleep while retelling the fantasy in my mind. With my fantasy and memory of that night, I had plenty of fuel for masturbation for days after that night.

The story would have ended here, but for some events later that summer. As my luck would have it, at a picnic there was a girl that I knew of, but had not gotten to know. In our town, there was a youth program for boys and a separate program for girls. Several times each year the two groups would do a joint activity such as a field trip or fundraiser. The group did a joint picnic for the kids that had graduated, at the youth center's facilities where there was a large open area behind the main building. There were picnic tables and barbecue pit abutting on a woodsy area with a stream running through it, a softball field and volleyball courts. It was a fairly secluded area, and a minimum of adult supervision, as most of us were already at least 18. At some point during the picnic, later in the evening, I overcame my shyness and talked to the girl whose name was Angie. I had not seen much of her because she went to a different school. Her older brother knew my older brother, but we had never talked. My friends had sort of abandoned me, leaving me alone at a picnic table next to the woods with my new friend.

Angie was different – dark hair and darker than average skin, and very curvy for an 18-year old. She had nicely developed hips and tits, and though she was short, her legs were nicely proportioned, making her look taller and older than she really was. She didn't seem to care about what the other teens thought – sort of a rebel. I was tall, skinny and athletic, somewhat nerdy and shy. It amazed me that she would even talk with me. But she said she thought I was cute, and she had me hooked. I would have done anything for her. She realized we were alone, and the picnic table where we sat was the most remote from the group, almost within the woods. Maybe this gave each of us some boldness. We talked about mutual friends, and she asked me if I had a girlfriend. I said no, but I wished I had one.

"Well, if you had a girlfriend, what would you want to do with her?"

That question shocked me, and I was starting to get hard just thinking about it. I looked around to make sure no one else was close enough to hear us. I figured it was now or never, what did I have to lose?

"Angie, you are beautiful and I can't imagine having a girlfriend like you. But if you were my girlfriend, I would like to lick you and kiss you...." At this point I was hard and very agitated, and almost shaking. I was having trouble expressing myself, but I think Angie sensed my intent.

"What do you mean? A boy has never done that with me. All they seem to want to do is to try to finger me and fuck me and make me suck their dick. But I like the idea of being licked, where would you do it with your girlfriend?"

I managed to calm down enough to say, "You might think I'm some kind of perv, but I hope not. I have a fantasy. I would meet you outdoors in the middle of the night. In my fantasy, I meet my girlfriend on top of the cemetery hill, and both of us are completely nude, lying on a blanket. I don't know much about sex, but I would love to lick your pussy and butt up on that hill."

There – I said it. I was prepared to be embarrassed, see Angie walk away, and never speak to her again. But the enthusiasm in her voice surprised me as she said, "That is so exciting to think about. But I'm not sure I know where you mean, tell me."

Turns out, her family lived on the other side of the cemetery, and not far from it. I explained the location of the hill. It was not an old scary cemetery, not fenced in, and had public driveway entrances on two sides. She lived about a half mile from the main entrance, and I described how to get to the top of the hill where my fantasy takes place. She wasn't sure how she could get away from her family in the middle of the night and get to the cemetery. That was true for me as well. I thought about it for a bit and offered, "Well if you're willing to try it, give me a signal one night by calling my number and letting it ring twice before hanging up. That will be my cue to do whatever it takes to meet you after midnight that night. I'll bring a blanket and lay it down on the hill so you can find it easily."

Angie was definitely up for it. She reached under the picnic table, squeezed my cock through my shorts and said I need to give her my phone number. Naturally at a picnic we had no pen or pencil or paper handy. I excused myself to go to the bathroom up at the main building, and said I would find something to write my phone number on to give to her.

When I came back, I handed her a little slip of paper with my phone number. Angie whispered to me urgently, "Ron, you have such fantastic ideas, and no other boy has ever included me in their fantasies. I can't wait to feel you licking my pussy and ass up on that hill. I will call your number one evening as soon as I can arrange it. I might even be inclined to teach you a thing or two, so be ready for my call..." And then we were interrupted – someone announced the picnic was ending. We had to clean up and get our rides for home. I said goodbye to Angie and told her I would wait for her call.

I was on edge every evening for days after that. My sister and parents didn't say anything, but they might have noticed that I was not going out in the evenings with my friends. Since my brother was gone for the summer, and would not be back before his fall semester in college, I asked my mom if I could move downstairs for the rest of the summer into the basement bedroom. My logic was that it would be cooler in the basement and I would be able to sleep better. She was OK with that, so I spent part of my evenings downstairs, reading as much as my mind would allow. We had two phones on our one line – one downstairs in the laundry room, and one upstairs. In the evenings I was really unable to focus on anything other than the thought of meeting up with Angie and licking her body.

Finally, the next weekend on Saturday night the phone rang about ten o'clock. I was downstairs and heard it. After the first ring, I was on my feet and heading for the phone. I got to the downstairs phone shortly after the second ring, picked it up, and heard a loud click. My parents were already in bed but my sister was still upstairs watching TV. She yelled, "Who was that?"

I answered, "I don't know, must have been a wrong number, they hung up."

I hung up the phone and went back to my room; now I was focused on meeting Angie. It seemed like forever to wait until midnight to meet her. I was extremely hard and agitated thinking about it, but managed to calm down enough to lie on the bed while waiting and read a book. I had stripped naked just to be ready.

Once the clock showed 11:30 I went into action. I had an old blanket rolled up. Unlike the upstairs room, it was much easier to sneak out from the basement room. I turned out the lamp. All I had to do was get the window open, remove the screen, place the blanket outside, and then using a chair for assistance, climb out headfirst. When I was out in the cool night air, I picked up the blanket, looked around and listened. From my hiding place in the bushes, so far I could not see or hear any sign of life – all was quiet in the neighborhood and I could see no lights. It was a relatively clear night, no breeze, and there was some moonlight. This would be riskier than I liked, but I was bold and determined to get to the cemetery and meet up with Angie. My cock was still hard with anticipation.

From my previous experience, I knew exactly the steps to take and the shadowy areas to stay within. My hearing seemed doubly acute, and I heard all the sounds around me – insects chirping, a car traveling on a distant road – but no sounds of any activity in my neighborhood. I carefully but quickly made my way through my yard and the next four back yards, checking for lights and any sign of activity, then found myself in the lot with the copse of trees. Here I had the choice – walk directly across an open field to the top of the hill, with no cover, or take the more circuitous route through the cover of the cemetery.

There were maybe three houses to the right, at the ends of two dead end streets that abutted the field. They had second story windows with a direct view over the field. But there were no lights on in any of the windows. I was excited, hard as a rock and almost on autopilot with my only thought to get to the top of the hill. In spite of the risk, I decided to set out across the field, figuring I had the blanket and could cover up if something happened. The distance was maybe 100 yards or less, up a slight rise. The grass had not been cut recently and it felt good on my feet and calves. The moon, while not extremely bright, was enough that I could see my shadow to the right of me as I took long strides up the hill. The slope was steeper as I approached the top, and now I was shielded from view of the houses by a row of trees over to the right. I was relieved that I got there before Angie, as I wanted to calm down and get ready for her.

I looked around my perimeter, and saw no movement or sign of Angie. I had described this open area to her at the picnic, and said she should look for the blanket. It was a light colored fabric and should be easy to see in the dark, especially with the moon out. I laid out the blanket in the grass. I didn't know what to do next since I saw no sign of Angie, so I lay down on my back with my cock pointing up, watched the night sky and tried to relax. My ears seemed hypersensitive and I could hear all the sounds around me – insects and not much else – but nothing that sounded like a person moving in the area.

After what seemed like an eternity, I finally heard what I took to be Angie – a whispered voice out in the dark said "Is that you, Ron?"

I could barely hear it, and said, "Yes, where are you?"

Then I heard, "I have been watching for you. I'm over here behind this bush. Stay where you are and keep your eyes closed."

Maybe she was shier than I realized, and I was intrigued. I closed my eyes and waited. Soon I heard movement over to my left. It was a quiet, calm night. I could barely hear anything else except the crickets chirping. I sensed movement, and took a peek. Angie had stepped over me and was straddling my head, standing over me with her legs spread. And she was nude! I could not see much because the space between her legs was in shadow, but I could make out her dark, wispy, pubic hair. My arms were at my side, but I wanted to reach up and feel her legs and ass. She bent down, put her hands on either side of me on the blanket, and lowered first one knee to the ground then the other. I peeked again – she was kneeling, facing my legs with her butt positioned over my head. I could not believe what I was seeing, but here I was, lying nude and hard in the night, about to lick Angie, a real girl. I was almost trembling in anticipation.

Angie whispered, "Okay, now open your eyes and stick out your tongue." She knelt there for a few seconds and wiggled her butt provocatively. "Do you like what you see?" She didn't need an answer – I lifted my arms and felt for her hips and ass. She spread her knees a bit wider and lowered her ass and pussy slowly to my face while I guided her in with my hands. It was my first time licking pussy. I was in awe of what she was doing – she tasted amazing. She was already moist, and I licked and licked. I did not really know what I was doing, but she instructed me in an urgent, sexy whisper – "Yeah, lick right there, and push your tongue in. Yeah, push it in and out. Mmmm...." As I tongued her, she pressed herself down on my face. I was pushing my tongue into her pussy, and she was wet and slippery. I alternated between tonguing her pussy and sucking up her juices with my lips. Angie was moaning softly and her skin was starting to get moist with perspiration.