Tobogganing - Cover

Tobogganing

by tisoz

Copyright© 2020 by tisoz

Young Adult Sex Story: Tobogganing leads to getting to know a girl better. This is part of a larger piece I am working on, but it stands on its own, so I thought I would share it.

Caution: This Young Adult Sex Story contains strong sexual content, including mt/ft   Consensual   Heterosexual   Fiction   Analingus   Masturbation   Oral Sex   Petting   Public Sex   .

I’d plowed and shoveled a few more drives over the winter, the small riding tractor (it seems silly to call it a mower when it doesn’t have a real mower) with its blade helped me get to more jobs and get them done quicker. It was really pretty handy for plowing as long as we didn’t get too much snow. It was maneuverable and, picking the right gear, it went about the perfect speed. We had a lot of snow that year and besides plowing and shoveling it, I did quite a bit of sledding and tobogganing with a cousin using his toboggan. Remember all those hills I mentioned? One of the better places we had access to was the hill behind my grandmothers. There was no barbed wire or other type fence to worry about, or trees or too short a flat area at the bottom with a creek. It was tree-free up to a certain elevation. The incline wasn’t so steep it was hard to climb, although you could go up the mild incline part and then across to a steeper place to go down. But the really steep part wasn’t really so much fun after you did it a time or two. You went down so fast and had to pay too much attention to not get over onto a rocky part and you were going so fast when you got to the bottom it hurt when you went over the little ditch-like thing at the bottom and if you were still shiny side up afterward, it took forever to slow down which just meant a longer walk back to the hill. Oh you caught the part about the ditch-like thing at the bottom? I guess it had actually been a ditch when it was originally dug decades before. I guess it was there to divert runoff from swamping the field. I knew the hill on the other side of the valley had no ditch and it was always swampy and muddy at the bottom of the hill.

One of the best times we had was when about a dozen of us kids and two toboggans spent the day playing. Two sisters from down the road joined us as well as their younger brother who was a friend of my younger brother. One girl was a year older than me and kind of stuck up. Her sister Debbie was sixteen, old enough to drive, and filling out into a beautiful young woman. People were smitten with Marcia Brady on TV growing into a woman before their eyes, but this girl made Marcia look like an also-ran. I immediately had a crush on the cute blonde. Like I’ve said, I was big for my age so maybe she thought I wasn’t as young as I was. The most memorable part of the day came on one ride when I was sitting behind her on the toboggan. I wanted very badly to reach around and hold on right about where her breasts were, but I didn’t want to be a pervert or anger her by pawing her so I just held on above her hips. We were all jammed up close to each other, the person in front of us sitting between our spread legs (on some previous trips I sat in front of her fantasizing she was way less dressed than she actually was) and hooked our legs over the legs of the person in front of us, while the person at the very front either sat cross-legged or with their knees up at their nose. We went down the less steep part of the hill, but when we hit the old ditch we went a bit airborne. Debbie came down right in my lap, and right on my rock hard member. When we were unpiling at the end, she got up and turned around and gave me a toothy smile while looking me up and down, but mostly in the middle.

The next trip down, Debbie jockeyed to sit in front of me and when I went to put my hands on her hips, she pulled them forward and down between her legs. I couldn’t have gotten any harder, but Debbie was wearing too many layers of clothes for me to feel anything so I don’t know if it mattered. But I pressed my fingers in trying to get a feel or at least be able to say I tried, and rubbed around as best I could. Debbie let out a little moan as we went down the hill and a loud Oh! as we hit the ditch, then moved my hands back to her hips as we slowed. This got repeated for as long as she could sit in front of me without being obvious. I was trying to help all I could, but the first time Debbie couldn’t get seated in front of me, she ended up sitting behind me. As we went down the hill she reached down and got a definite feel of my erection - through underwear briefs, long, thermal underwear and two pairs of pants. But I felt like I was going to rip through a few layers if I got any harder. I wanted to reach back, but didn’t press it and tried acting like we were just going down the hill like everybody else. The next time, Debbie jockeyed to sit behind me and on the way down was trying to wrap her hand around my member and stroke it up and down. It didn’t work out so well, but I surprised her on the next trip by discretely unzippering both pairs of jeans. We were halfway down the hill before Debbie figured out what I’d done and got her mitten off.

At the bottom of the hill, I excused myself and went into my grandmother’s house and went into the bathroom. I left my penis out, parting the fly on the two pairs of underwear, and also left the zipper fully open on the inner pair of jeans but zipped up the outer pair. I headed back out and looked for my new best friend. I waited as Debbie rode down the hill, then lagged behind so we were the last heading up the hill and I gave her ass a squeeze after admiring it part of the way up, then kept admiring it the rest of the way. I think Debbie added a little more wiggle to it, teasing me with her unattainable bottom. When we got on the toboggan, Debbie sat in front of me. I wanted to guide her hand back and into my pants, but I didn’t want to wrench her arm and possibly hurt her and fantasizing about such a position had to be better than impractically trying to do it. It got better though when Debbie guided my hands inside her jacket. I Immediately removed a glove and got a better feel of her breast with one hand. I could feel her rock hard nipple through her bra and who knows how many layers of clothing. Maybe it was just the cold, but I doubt it. We were having too much fun copping feels amidst the joy of the downhill ride. Debbie was anticipating the ditch on the rides and was really pounding back into my erection every time we went over it.

The next time down Debbie was behind me and already had her mitten off when we started down. I had snuck the remaining zipper open as we loaded on the toboggan and when she slipped her hand through Debbie took in a surprised Oh! to find naked flesh. I don’t know how hot it was, but it was definitely hard and warm. Debbie gave me some proper strokes and I thought she was going to rip it loose when we came down after getting airborne passing the ditch. Debbie withdrew her hand and even zipped me up a little as we came to a stop. On the way up Debbie whispered to me to take off my gloves for the next ride. Near the top, I took off my gloves and stuffed them in my coat pockets and climbed in behind her in the last two spots at the back. As we started down, she leaned back really pressing into me and when I realized Debbie was trying to guide my hand under the top of her pants. I quickly leaned back and almost fell off. She guided my other hand inside her top and to her breast, then leaned around and gave me a kiss. Her tongue hit my puckered lips and I quickly relaxed them and let them part to her invading tongue. Debbie bit her tongue a bit as we passed over the ditch. I came down partly off the back and was falling off the back, dragging Debbie with me since my hands were trapped in her clothes. I got them loose as we rolled with the momentum, quickly enough coming to a laughing groaning halt. We got yelled at for messing up the snow track where we’d skidded and dug into it a bit which made us burst out with renewed laughter.

Debbie collected herself and said she had gotten sort of wet sliding through the snow this last time and thought she better call it a day, then asked me if I could give her a ride home. I don’t know if she thought I had a car and driver’s license, but I didn’t correct her but pointed to my little riding tractor and plow. She didn’t seem too upset and after I got on and started up, she sort of climbed on in front, mostly sitting in my lap and firmly grinding down on my erection. It had no suspension and every jolt jammed my erection into Debbie’s softness. She took one of my hands and pressed it between her legs, covering it with both her hands to look as discrete and innocent as possible to any possible onlookers as we sped down the road. We arrived at the long dirt road of her driveway and she had me pull into a small barn on the approach to the house.

“I have got to see what has been poking me for so long,” Debbie said as she turned around and sat on the tractor hood and leaned way over to fish out my erection. I unzipped her jacket and was trying to free her breasts when she decided this position was not so good. We switched places and I had the edge of my butt on the edge of the hood as the steering wheel helped part the top of my legs somewhat straddling somewhat partially sitting on it. The position didn’t quite put my crotch at her eye level but it got it up there and on display.

Debbie guided my cock out and greeted it with a “Wow!” followed by an “mmmm.” I asked if I could see her breasts as she started stroking me. I quit caring if I saw her breasts. Debbie carefully eased my balls out of the tighter layers of underwear and gently fondled them with one hand in the more spacious and relatively warmer area within my jeans. I opened my eyes again as I felt something warm on the underside of my cock and saw Debbie’s face very close to it. Either she wanted a really close up view or she was up to something. I felt her warm breath, then her lips brushing along my shaft. As they neared the tip, her lips parted and her tongue tasted the hole at its tip. Then it was like her tongue was guiding me between her parted lips and into her mouth. It felt heavenly. I tried to let her know how great she was making me feel, but I couldn’t remember how to speak. I just moaned my appreciation, then remembered a word.

“Yes!. Oh, yes!” I couldn’t think past the sensations but tried to communicate an entire conversation just using the one word. Debbie let me loose from between her lips and I quickly remembered another, “No!” Debbie grinned as she looked right into my eyes and slowly took me back between her lips, her face lowering and my dick disappearing as she went. I could feel her tongue at first circling my head then wiggling back and forth as she took me in and finally extending to stimulate as much of my length as it could reach of the shaft she couldn’t engulf. “Oh, yes! I love you,” I blurted.

Debbie giggled causing her teeth to graze my sensitive flesh, but it felt interesting and wasn’t enough to hurt. Disengaging from my cock, Debbie said, “I bet you do. How much do you love me?”

“I’d do anything for you,” I said, having no idea how encompassing a statement it was.

“We’ll see,” she said. “By the way, what is your name? Mine’s Debbie or if you are in a hurry, Deb is fine.”

I couldn’t remember my name for a second, then said, “William. Or just Will.”

“William, the great white whale of a dick,” Deb said. “Where there’s Will there’s a way.” Then she quit talking and used her mouth for better things. Much better things as she continued to pump what she could of my cock in and out of it. Maybe it was the cold, but it took me a good long time to cum. When I did, Debbie released my cock from the confines of her mouth, letting the next spurt fly several feet into the air.”Oh,” she let slip with a surprise and positioned her mouth agape about 2 inches above my spewing cock. She was using her hand to hold me steady and guide my deluge to spray inside her mouth. Not swallowing or trying to hold it in her mouth, my discharge ran back out of her mouth and dripped onto my cock.

Seeing her beautiful face over my cock as she tried minimizing the mess of my ejaculation as it jetted into her mouth and then drooled back out was so dirty and so damn hot. She had to be getting a pretty good taste of me. Soon her hand was glazed with semen, making her look even sexier to me. Her blue-eyed gaze moved up to my face, away from watching my sperm shoot out of my cock. I was staring at this blonde goddess letting my spunk hit the inside of her mouth and drool back out onto my cock and her dainty hand. She looked so hot and sexy. If I ever made an adult movie, I was going to copy this as the signature money shot. I thought it was hotter than if she had swallowed my load.

My cock quit spasming as well as erupting and she figured it was safe to uncover the tip. The thought quickly came to me, she had acted sort of like a soldier jumping on a grenade, instead, sacrificing her mouth to reduce the blast area of my ejaculation. All thought but STOP left my mind as she stroked my softening member. I was still much to sensitive and I jerked in pseudo pain as she used my cum as lubricant to start a handjob. I wrapped my fist around her hand and slowed her strokes, also tightening it around her a bit so her hand did not slide across my hyper-sensitive skin. I let her pull the skin up and down the shaft - but only slowly as I rode out the pleasurable, post-orgasm sensations.

Without losing her grasp on my cock, Debbie moved up next to me and gave me a deep kiss. After a couple of minutes, she broke the kiss, complimenting me on not shunning the kiss.

“Anyone who would reject any kiss from such a beautiful lady as you, especially after you brought them such happiness, is an idiot and never deserves any more of your attentions,” I blathered.

Debbie said, “It was sort of payback for me having to taste it. But I didn’t want it flying all over me and everything around. You really came a lot, and it would have flown everywhere. Plus, I wanted to see how prudish or uninhibited you were. You hardly flinched. Maybe we can explore some more things.”

Wow! The thought I might get to experience more of this lovely young woman blanked my mind. I couldn’t even picture her naked and spread open beneath me at the moment. WOW! was all my brain was processing. As we returned to kissing, Debbie kept gently pumping my cock, bringing it back to action and it dawned on me I soon might not be having to imagine her naked and spread open. I might be seeing the real thing in the future. Maybe in mere moments.

I was using one hand to prop us up. The hand I had used to slow her more enthusiastic stroking had drifted to her hip. I sort of tested how dry it was from my semen and thought it might be good enough not to transfer a mess. I moved it to her butt cheek and pulled her more up and onto me as I stopped using my other hand as a prop and laid back. My free hand wanted to feel her breast. I wanted to feel her breasts. Hopefully, I’d be feeling them flesh on flesh. Hopefully, I’d get a chance to honor them with my kisses. As I pulled her onto me, I wanted her to feel my cock pressed to her pussy, or more likely, the pelvic cradle between her flaring hips. I hoped letting her feel it pressing into her there would get her thinking of how good it would feel inside her.

Breaking the kiss, Debbie smiled and good-naturedly pointed out, “You are such a naughty boy, How did your hand get between my ass cheeks and pressing into me in such a disgusting way? And your other hand is touching my tits so lewdly. You are such a dirty boy, pressing your big, evil cock into my innocent tummy. I do declare. Why, what would my mother think if she saw us right now? You with your evil hard on exposed to my eyes and even making me touch IT.” Debbie got off me and stood. I might have started believing what she was saying if she had ever released my erection. Instead, she kept up the banter as a sort of foreplay as she started shedding clothes.

“As much as I don’t want you to,” I said, “it would probably be quicker and easier if you used both hands.”

“A gentleman would help a lady,” she said. I was quickly on my feet helping undress her. Unwrapping this angel from Heaven. Or temptress from Hell. Either way, I was lost to her charms. After a few layers, I pulled her thermal underwear top over her head and let her long blonde hair slip through the opening and gazed on Debbie with only a white bra between my eyes and her mounds. I got lucky and the clasp popped open without much effort, not making me look like a fumbling, inexperienced klutz. When the bra came off, I quickly covered her hard nipples with my hand on one and my lips kissing the other. “Whatever would my father say if he saw us now, you defiling me so,” Debbie resumed her mock innocent act. She had only released my cock briefly a time or two to shed clothing and had immediately taken control of it after and resumed her slow pumping.

Debbie had moved us around to where we exchanged positions. With her multi-layers of pants loose and unfastened, Debbie inched them down slowly as they hugged her like layers of skin. She got her butt on the front of the tractor hood I had just lain back on from the opposite direction and leaned back a bit while holding me in place with a palm on my chest. I looked to her face after having my new toys taken away. “I know you want to keep sucking my tits, Debbie said. “What is it with guys and tits? But I could use some help getting these pants and boots off.”

Debbie had to release her hold on me to let me help her with any kind of real help and after removing her boots, I quickly skinned her layers of pants from her. Through this part of the disrobing, she had managed to pretty well keep her legs tightly closed, obscuring me from getting any glimpse of her private treasure. I only saw a darker blonde patch of hair as she quickly pulled me into an embrace. Her hand found my cock before our lips found the others, and we hungrily and enthusiastically kissed as she increased the speed of her strokes on little Willie.

 
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