Sucking Teenage Skateboarder Cunts and Cocks on the Trail



I’ve had a pretty typical life, that is, up until the events I will describe in this story, which began almost a year ago. I was born, raised, and educated in the Midwest, and then married my high school sweetheart after we graduated from college. My name is Ryan, and I’m now forty years old and living in a suburb of Minneapolis with my wife Sarah and daughter Brooke. Brooke just turned sixteen in the spring before the end of her sophomore year in high school, as did Kaley, the daughter of our next door neighbors.

Brooke and Kaley had been friends since the first grade, but as they grew into their teen years, Kaley started hanging out with some boys who were skateboarders and a little on the fringe socially. Brooke made friends with the more-popular kids, and became a cheerleader and was involved in many school organizations. So the girls’ friendship lessened as they got older.

Our middle-class neighborhood borders on a beautiful forest and prairie area where I am able to stay in shape by running on the nice paved trails. I’m self employed, and my manufacturer’s representative job allows me to work from home most days when I’m not traveling. Back when Kaley first started skateboarding, I would often see her on the trails in the forest preserve with two boys from the neighborhood. I didn’t know the boys that well, but knew that they were Kaley’s age and their names are David and Kevin. That was usually during the summers and on weekends when the kids weren’t in school.

The trail meanders through some open prairie land, and in places goes through heavily-forested sections near a stream. Kaley and the boys liked to rest from riding their boards and hang out near a concrete flood control structure and spillway. They were constructed many decades ago to manage flooding in a section with enough elevation change that erosion was a problem. Being teenagers, Kaley and the boys usually ignored me when I saw them on the trail or sitting on the walls of the structure.

Kaley is a petite and very pretty girl with straight, naturally-blonde hair, and I certainly couldn’t blame those boys for wanting to hang out with her. I never saw anything sexual or dangerous going on with them. After all, they were just kids, like my Brooke, who were enjoying their childhoods. However, during the spring and summer when the girls and boys turned sixteen, I saw many changes.

I couldn’t help but notice that Brooke’s body had developed, and she was becoming a voluptuous woman just like my wife Sarah. She has firm, D-cup breasts and a nice full ass that attracted a lot of boys to her. I also noticed that David and Kevin were taller, more muscular, and were becoming touchy-feely with Kaley when I saw them on the trail. They were often hugging and kissing one another, although it looked like Kaley had not developed physically anywhere near as much as my Brooke. Her legs were firm and shapely, but thin, and it looked like her breasts might be a B-cup or a little less. She was petite and slimly built like her mother. Her ass was nicely shaped and protruded a little, but it was still small. The one area that seemed to be fully developed was her pussy.

When I passed them close-by on the trail, I noticed that Kaley almost always wore tight, sheer, flesh-colored leggings, that looked a little like yoga pants to me. She didn’t wear underwear and those tight pants obscenely displayed her prominent mons pubis and thick labia. Her camel toe looked even larger due to her thin legs and overall thin figure, and looked too big for her body. My mouth watered every time I saw her, and that brought back memories of my days as a junior and senior in high school.

Back in those teen years, when I was becoming sexually active, I soon realized that I liked oral sex almost as much as fucking. I just loved the look, taste and aroma of pussies with thick, hairy labia, and I loved eating them out. That was a good thing too. Many of the girls did not want to be penetrated and inseminated due to the risk of getting pregnant, but they loved being fingered and having their pussies sucked to orgasm.

I also have a rather small, four inch dick, and always felt a little self-conscious when girls saw me naked. So I became addicted to sucking their cunts and tasting and swallowing their vaginal fluids, without having my dick sucked or fucked. I started dating Sarah during our senior year in high school, and she also enjoyed having me eat her out. She didn’t let me fuck her until our sophomore year in college. Sarah married me, despite my little dick, mainly because I always satisfied her with my mouth, either before or after we fucked. And, me performing oral sex on her continues to be a large part of our sex lives.

The more I saw Kaley, the more I realized that my attraction to her was becoming obsessive. I even started timing my runs for when I thought she and the boys would most likely be out on the trail. Her blonde hair framed her face in a way which made her look even prettier and more innocent. I was sometimes ashamed of myself for lusting after a sixteen year old girl, my own daughter’s age, but felt better about it when I learned that she was not so innocent herself.

One day I was running by the spillway, and caught a glimpse of Kaley following the boys into the trees and thick bushes, just a few feet off of the trail. That was the first time I had seen them going back there, and I became suspicious. I waited for a few minutes to make sure that they weren’t coming right back out, and quietly followed them. The undergrowth is very thick there, and I only had to take a few steps before I saw them is a small clearing where there was a thick layer of leaves on the ground. Kaley had already taken off her t-shirt, and was in the process of taking off her leggings. I loved her thin, lithe body and those firm little titties, but almost gasped out loud when I saw her pussy in the flesh. A layer of neatly-trimmed blonde hair covered her pubic mound and labia, and it looked like she was already wet in anticipation of what they were going to do.

I stared at her for a few long moments until my focus shifted to the boys, who were pulling off their shorts and underwear. I have never had an interest in boys or men, and especially not their junk, but I was impressed by the size of the genitals on those sixteen year old boys. Their soft, uncircumcised cocks and low-hanging balls hung and swung freely between their legs, in a way that my little dick never could. David’s cock looked to be about seven inches long and very thick, while Kevin’s was a little shorter, but even thicker. My dick was getting hard in anticipation of what I was going to see.

Kaley unceremoniously lay back on the leaves and spread her legs. She reached down and parted her labia with her fingers as she said, “Hurry up, David, you go first this time. I need your big cock in my pussy right now. So hurry up, I need to be home soon.”

Kevin stood there watching and stroking his hardening cock, as David got on his knees between Kaley’s legs. Oh, the joys of being a teenager. His cock was already hard and looked to be about nine inches long, with a huge cock head, and covered with protruding veins. I was in the perfect position to see between their legs as David easily pressed his huge cock into her thick, wet cunt, and I wondered why he wasn’t wearing any protection. It was amazing seeing that petite, thin girl being impaled on his thick cock. He began fucking her with no foreplay, and I heard his cock squishing in her wetness as his big, hairy balls slapped against her ass and inner thighs.

I remember thinking that it was such a waste that they didn’t have oral sex before beginning to fuck. Kaley was writhing in erotic lust and having orgasm after orgasm, until David finally held his cock buried in her pussy. It was so arousing watching his ass clinch repeatedly as his balls pulled up, and I knew that he was flooding her young cunt with cum. When David pulled his softening cock out of her, Kaley kept her legs widely spread for Kevin. I had eaten plenty of my own cum out of my wife, and I wanted to suck Kaley’s pussy and swallow all of their juices. That’s the first time I ever had a desire to eat another man or boy’s cum from a pussy.

As Kevin move between her legs, I saw that his cock was about eight inches long, and so thick that it almost looked like a log sticking out of his teenage groin. He pressed his cock into Kaley as he said, “Oh fuck yeah, it’s always easier to get it into you after David has reamed your hole and slimed it up for me.”

I watched as Kevin pounded her pussy, and realized after a few minutes that I had unconsciously reached into my running shorts and was masturbating my dick. I shot my load into the leaves just as Kevin filled Kaley’s cunt with the second load of cum within only ten minutes. She just lay there with her legs lewdly spread after he pulled out of her, and I loved seeing those combined loads of cum oozing from her pussy. The boys then pulled their underwear and shorts back on, as Kaley wiped her pussy with a tissue to remove at least some of their thick cum. I was close enough that I could smell her pussy and the boys’ semen.

The rest of my run home was tormenting as I thought about Kaley’s fat, young pussy, and how she so easily let those boys fuck her. It was clear to me that they had fucked many more times that summer, and I had to think that she was on birth control of some kind. I couldn’t get the vision of her young body and oozing pussy out of my mind. When Sarah and I went to bed that night, I ate her pussy both before and after we fucked, and she couldn’t understand why I was so hungry to suck her pussy. I imagined myself between Kaley’s legs, sucking those boys’ cum from her teenage pussy.

After that first time watching the boys fuck Kaley, I paid more attention when she left home with her skateboard. My home office is on the side of our home facing Kaley’s home, and I had a good view of the front door that she usually left out of. Over the next three weeks, I had watched the three of them fucking over a dozen times. Kaley was a real cock slut and couldn’t seem to get enough of those big cocks. On some days, when they had more time, they stayed there and fucked twice. I was so envious of the boys and their big cocks, but even more I wanted to suck her thick cunt. My opportunity to finally get to go down on her came about in a most unexpected way.

One day in the middle of the summer, I was running from home and was about five hundred yards from the spillway. I saw Kaley and the boys skateboarding very fast towards the spillway from the other direction, with what looked like clothes in their arms. I didn’t think too much of it until I got there a few minutes later and quietly took my place in the bushes. Kaley had already removed her leggings and was lying back on the leaves. The boys were undressing and I noticed three piles of what looked like t-shirts, shorts and other sports clothes, and they all had store tags on them. I was very suspicious and alarmed about what they might have done, and knew that there is a mall on the other side of the forest preserve. I wondered if they had stolen those clothes.

I was just settling in to watch as Kevin pushed his thick cock into Kaley, when I heard a stern voice ask, “Hey, mister, what are you doing in those bushes?”

The kids looked back and saw me standing there, just before I turned and walked out of the bushes. I didn’t realize that someone would be able to see my back from the edge of the bushes, and I was surprised to see a police officer standing there. I saw his bike and knew right away that he was one of the off-duty cops who worked security at the mall. He looked me over and repeated his question. Then I responded, “Sorry, officer, but I’m out for a run and had to take a piss. I sure hope I’m not in any trouble.”

The officer smiled at me and said, “No, man, I’m not worried about that right now. I’m looking for three kids who just shoplifted a bunch of clothes from the sporting goods store at the mall. They are two, tall boys and a cute blonde-haired girl, all of them on skateboards. Have you seen them come by you on the trial?”

I wasn’t technically lying when I responded, “No sir, I didn’t pass those kids on the trail. Good luck finding them. Little thieves like that make things more expensive for all of us.”

The officer took off down the trail on his bike. The kids saw me watching them, and I knew that I had to face them. Knowing that they were being sought by the police for shoplifting would make things easier for me. I went back into the bushes, and stepped into the clearing. The kids were clumsily trying to get dressed, and Kaley asked, “Oh shit, Mr. R., I’m so embarrassed! We’re so thankful to you for not turning us in to the police, but, but…what were you doing watching us? Is this the first time or have you watched us before? And what are you going to do about this, tell my parents?”

I was upset with them for shoplifting, and decided to give them a good lecture about the realities of the world, and how something like that could fuck up their lives. By the time I was finished they were almost in tears and seemed remorseful. I suggested that they find a way to return the clothes, without getting caught. While I had the upper hand, I decided to answer her questions. I said, “I know this might sound pretty fucked up, but I have been watching you three for the last three weeks. I saw you the first time quite by accident, and got so turned on that I wanted to see more. You know, Kaley, you’re quite the little cock slut. And as far as your parents are concerned, whether I tell them or not is entirely up to you. What are you willing to do to convince me not to tell them?”

The boys hadn’t said a word up to that point, and Kaley was in tears. She didn’t know that I couldn’t very well tell her parents and admit that I had been watching them for three weeks. So she replied, “Oh fuck, Mr. R., that was so perverted to be watching us like that. And what do you mean about me convincing you not to tell? Are you trying to tell me that you want to fuck me too?”

I knew that after I answered her question, I wouldn’t be in as strong a position with them. But I very badly wanted to taste her thick, slutty cunt, and I replied, “Look, Kaley, I’ll admit that I want to fuck you sometime; it’s just that I want something else first. I’ve been watching David and Kevin fucking you with their big cocks, and leaving your pussy filled with cum. It just so happens that I’d like to eat your pretty, young, wet cunt and suck your tits, and I want to be a part of things when you guys get together from now on. I want to watch you fuck the boys up close, so close that I can smell it, and then I want to suck your pussy clean. And by the way, since we’re all going to be getting to know one another so well, you can call me Ryan.”

Kaley smiled and said, “Holy fucking shit, Ryan, that sounds so sick for you to want to clean my pussy like that. I love it though. I’ve been trying to get David and Kevin to suck my pussy since we first started fucking about four weeks ago. They won’t suck me because they think I’m a dirty slut for fucking both of them, and they assume that I’m probably fucking other boys. For that reason I won’t suck their cocks either. If you’re serious, we can try it now.”

The boys looked dumbfounded listening to our conversation about my involvement. But they were also happy that they wouldn’t be getting into trouble, and could still fuck Kaley. They quickly agreed to our new arrangement. Kaley pulled off her leggings and t-shirt and lay back on the leaves with her legs spread. Then she said, “Come on, Ryan, and get a taste of me before the boys get me all slimed up.”

I got onto my knees between her legs, and leaned down to suck her little tits. Her areolas were puffy and her nipples were hard and rubbery. I sucked them for a few minutes before sucking, licking and kissing my way down her taught, slim torso. I got the scent of her sweet, young pussy as I tongued her belly button, and then I moved the rest of the way down, lifted her thighs over my shoulders, and began sucking her wet pussy. Kaley lifted her hips and humped against my face as I sucked and tongued her thick labia and clit. Then she rose up on her elbows looking down at me between her legs, as she said, “Oh fuck, Ryan, that feels so good. Seeing you down there happily munching away on my sweaty pussy, I have to wonder what Brooke would think if she knew that her daddy was sucking her friend’s young pussy.”

Sucking her young cunt brought back my pleasant memories of sucking the girls in high school, and I loved having her hairy labia in my mouth and the taste of her sweet juices. I sucked her that way for about five minutes, and I saw in my peripheral vision that the boys were stroking their cocks and were hard and ready to fuck. So I reluctantly pulled back, still between her legs, and watched as David moved down to fuck her. I watched in awe as his big, hairy cock slid into her welcoming pussy. Then he started fucking her and I was only inches from his swinging balls as they slapped repeatedly against her ass. I wanted an even closer look of their coupling, so I said, “Wait just a minute David. Let’s change positions so I can really get my face in the action. I’ll lay on my back with Kaley on top of me, face down and in the other direction, and you can fuck her from the rear.”

We changed positions, and my face was soon pressed into the top of her labia, as David’s big cock slid over my forehead into her pussy, and his balls slapped against my head. I had never been so close to a boy or man’s cock, and it somehow seemed okay, since Kaley’s pussy was also in my face. I soon had to lower my head to rest my neck, and that’s when his huge, sweaty, teen balls dragged across my face and mouth. It seemed only natural to lick and suck his balls intermittently, and that’s when I heard David say, “Holy shit, this old fucker is sucking my balls. I’ll bet that he’ll suck my cock too, after he cleans Kaley up in a couple of minutes. What a nasty, old pervert he is. Aw fuck, here comes my cum now.”

From my position I saw his balls draw up and the base of his cock pulsing, and knew that he was inseminating Kaley. He stayed in her, slowly stroking, until his cock softened. He then pulled his cock out, and stayed right behind my head on his knees, with his slimy cock against my head. I covered her labia with my mouth, and his cum came flooding out of her cunt, as I sucked and licked for more. I was remembering how plentiful and thick teen cum can be, and I loved the taste of his big, thick load.

After I had thoroughly cleaned her pussy, I lay my head back on the leaves. That’s when David moved the couple of inches needed to push his cum-covered cock against my mouth. I hadn’t planned on sucking him, but in the lust of the moment I opened my mouth and took in his thick cock. I began sucking his oozing foreskin and head, and then took in more of his shaft. I loved the texture of his cock and skin, and having his thick meat in my mouth. I was sucking down more of his shaft as David said, “Oh fuck, Kevin, you’re gonna love having this cock sucker clean your cock after fucking Kaley. This is the first time anyone has ever sucked my meat, and I love it.”

David soon moved out of the way and Kevin took his place. He began fucking Kaley and I watched as his thicker cock impaled her cunt. I was sucking and licking her pussy and his balls, and then felt Kaley pushing down my jogging shorts. Then I heard her laugh as she said, “No wonder he likes your big cocks. He’s got a little one, and it’s just perfect for sucking. It’s already leaking precum, and I’m going to get my first taste. Then I felt her mouth engulf my dick, as she began sucking me. It felt so wonderful, especially knowing that it was a pretty, young girl like Kaley sucking me. I knew that I wouldn’t last very long, since I was so aroused from sucking her pussy, swallowing cum and sucking David’s cock.

Kaley kept sucking my dick, and in only another minute I was shooting my load into her mouth. She kept sucking me and swallowing, as Kevin buried his big cock all the way in her pussy, and filled her with her second load of cum for the afternoon. She kept sucking me as I covered her labia with my mouth and sucked all of Kevin’s cum from her. Afterwards I cleaned Kevin’s cock, and I had to strain to open my mouth wide enough to take it in.

We sat around and talked for a while, with our clothes still off, as they boys fondled their cocks and Kaley casually fingered her sweet pussy. Kaley said, “Ryan, it was a big enough surprise finding out that you had been watching us and wanted to eat my just-fucked cunt, and even more amazing when you sucked the boys’ cocks for them. You really are a nasty old guy, and I have to wonder what Sarah and Brooke would think if they saw you here right now. I’m not complaining though. I loved having you suck my pussy clean, and then watching you suck those thick cocks.”

She paused for a moment, and looked serious as she continued, “You have something over us by catching us out here like this, and knowing that we stole these clothes. And now we have something over on you. We are of legal age for having sex, but I’m sure that you wouldn’t want others finding out about it, especially about you being a cock sucker for teenage boys. Since you said that you wanted to be a part of things from now on, I’d be willing to let that happen if you pay me. David and Kevin can ask for money too if they want too. I just know that I want fifty dollars every time we get together. That’s because you have spoiled our little money-making scheme to sell these clothes to our friends. And judging from how fast you shot your wad into my mouth, I know that it really excites you being with teenagers like us.”

We agreed that I would pay Kaley fifty dollars, and each of the boys twenty-five dollars each time we met on the trail. We soon got into a routine of me meeting with them an average of twice a week, where the boys would fuck her at least two times each. The more I sucked her cum-filled pussy and their cocks and balls, the less respect the teens had for me and the more depraved I became. The more disgusting activities started one day when I was sucking Kaley’s pussy clean of cum, and she decided to sit up on my face.

I loved that new position of her sitting on my face, and the erotic feeling of being pinned under her that way. I held onto her hips as she pressed her oozing pussy into my mouth. Then she began to slide back and forth over me, fucking my face with her pussy. At one point, probably by accident, she slid farther forward, which placed my face right between her nice, tight ass cheeks. I kept sucking, licking and tonguing her as I had been doing, and soon realized that I was actually sucking her asshole. That was the first time in my life I had ever done that, and it turned me on so much that I held her tightly on my face as I sucked and tongue-fucked her hole. She was slowly gyrating and pressing her hips to my face as she said to the boys, “Holy fuck, watch this guys. Ryan is sucking and tonguing my asshole. Oh shit, it feels so fucking good. You should try it with him when I’m finished.”

Following that first experience sucking Kaley’s ass, the boys began to sit on my face and feed me their balls, before sliding forward for me to suck their assholes. I know that it sounds sick, but I loved being used by those teenagers that way. They were always sweaty from skating to our meeting place, and the musky smell and taste of their crotches became intoxicating to me. I couldn’t seem to get enough of their asses, as well as Kaley’s pussy and the boys’ cocks, balls and cum. And after having been completely heterosexual my entire life, I was getting to the point that I loved sucking the boys’ cocks almost as much as I enjoyed sucking Kaley’s pussy.

We continued meeting like that on the trail until school started in the fall, and then I could only meet with them on weekends. Fortunately, the teens started bringing two other teenage skateboarders with them, a girl and a boy. All three of the boys took turns fucking both of the girls, and I was getting as much teenage pussy and cock as I could handle. During the late fall and winter it was too cold to meet on the trail, so I was able to have the teens to my home on those days when I knew that Sarah would be out all day.

When Kaley and the other teens became seniors, they introduced me to another girl and two more boy skateboarders who had just turned sixteen. I was able to continue meeting with those teens for the next couple of years, and it’s amazing to me that Brooke never heard about me sucking her friends from high school.


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