Author's note: Many thanks to Literotica's own LadyCibelle for her editing expertise in making my stories more readable.
The first Saturday in May, I went down to the school to shoot some baskets with some of the guys and walked home in the late evening. I cut through Carver City Park mostly just to vary my routine, since it was a little longer than the most direct route. It was a pleasant walk with the temperature just right, all the trees and grass very green from April rains, and birds and squirrels wandering around. There were people all around but none that I recognized. However when I passed the swing sets two girls began to follow me and I heard them whispering and giggling behind me. I zigged and zagged along a couple of paths just to make sure and then at a corner I turned and asked "Are you two following me?"
One answered "Uh, huh. Are you Kevin Carter?"
"Yes. Who are you?"
The blonde said "I'm Nancy Trotter and this is Carrie Wilder. We're in the sophomore class too but don't have any classes with you. We've heard about you and ... well, we wanted to know if it's true."
"What did you hear?"
The brunette responded "We heard that you're hung like a horse. At least that you've got the biggest penis that any of our friends have ever seen. Is it true?"
"Ladies, I don't know. Are you willing to find out?"
In unison, they both shouted "yes!"
I said "I've got a rule. You have to show me yours too."
Nancy said "That's no problem." She took my arm and pulled me. "We know where there's a spot where nobody else ever goes. Come on." We headed off the beaten path into the bushes, into some thick undergrowth. Sure enough there was a winding trail, if you could call it that, that let us get into a sort of park within the park, an area completely surrounded by low-growing bushes and tall trees but with a grassy spot in the middle about the size of my room at home.
Carrie began tearing at my belt and jeans while Nancy took off my shirt. I pulled on their tops one handed and struggled but the girls finally whipped them off as if they were suddenly hot. Shorts and panties quickly followed and they both dropped to their knees in front of me. Carrie squealed in delight as my dong inflated and stood at attention. Fingers probed the contours of my arrowhead, down my shaft and around my ever-ready nuts.
These were not two shrinking violets. They were take-charge types and pulled me to the soft grass, where Nancy threw a leg over me and guided my sword into her sheath. No sooner had she settled down and engulfed my entire rod than the sun disappeared from sight as Carrie lowered her bottom over my face and all I could see was a cute little ass as my mouth covered her cunt. Nancy whispered over and over that she felt totally, totally full ... and how she wanted to keep it that way.
Carrie was dripping cunt juice when she squatted over me and my tongue elicited more, much, much more in the next twenty minutes. She kept shaking and quaking so much that I didn't know how many orgasms she had but she was having a good time, at least up until she could no longer stay upright and fell off to the side to rest on the grass.
Meanwhile Nancy decided to use my flagpole as the point for a spinning top, turning herself through several 360º turns. Every time by my scrotum, she tugged at my balls and then in the next half circle, she would rub or pinch my nipples. Every so often, she stopped for a couple of minutes of hummingbird speed humping, ramming herself up and down my shaft like a jackhammer. I felt her climax several times but it wasn't until Carrie fell off that I knew the impact they made on Nancy ... to keep from crying out, she had bit down on her lower lip hard enough that blood was slowly dripping from her chin. She was oblivious to it though, so intent was she on the good feelings coming from our point of connection. About 35 minutes after sitting on me, she also fell off in exhaustion, forming a triangle of bodies with her head almost touching Carrie's.
I got to my knees and retrieved my jeans. I fished out a clean handkerchief and cleaned up the blood on Nancy's breasts where it had dripped, then held it to her chin until it stopped bleeding. My dong was still rock hard and throbbing and, since I hadn't been inside Carrie and she was laying with her butt up, I straddled her legs, pointed my tool between them and pushed forward until it slipped into her pussy. She hadn't protested ... in fact, she reached back and spread her buttocks to help me find the mark. I was soon lying on top of her with my crotch pressing against her cute ass, most of my thirteen inches inside her hot pussy. She made a tripod of her forearms and rested her head on it while I fucked her. I worked a hand under her and massaged her mound until she came ... and came ... and came ... and came again just as I spewed cum into her cunt. I rolled off, lay back on the grass with my head on Nancy's stomach and my legs across Carrie's ass and took a short nap.
Both girls had a hand on my cock when I awoke. My newest erection had them fascinated. I asked Nancy to let me fuck her doggy and she got up on hands and knees for me. By the time I had knee-walked around behind her and guided my schlong into her steamy quim, Carrie had squirmed around so that she was under Nancy in the 69 position and Nancy buried her face in Carrie's pussy while Carrie began to suck one of my balls. It was a delicious activity that resulted in multiple orgasms for both girls and a very satisfying one for me.
The two girls licked and sucked my cock until it was hard again. This time I mounted Carrie while Nancy sat on her face. I managed to fuck Carrie and suck Nancy's titties while Carrie was eating Nancy's pussy. By the time I climaxed, both girls had cum several more times. By then it was late and we were all exhausted. As we were dressing, I snatched their panties and explained that I needed them, preferably signed which they both did, giggling of course. We exchanged phone numbers and I walked home, tired but happy.
Into my junior year things became a little more hectic. The senior cheerleaders were gone replaced by a new crop of senior cheerleaders. A new class of sophomores moved in and they soon picked up on my reputation. Even more girls wanted to have sex with me, to test being fucked by the biggest cock they had ever seen. I tried not to disappoint any while still keeping up with my regulars from the prior year.
Elizabeth Stanton was still my favorite snatch. We had managed to fuck weekly, even through the summer vacation except for a week when she went on a trip, and still no one else was aware of our relationship, so far as I knew.
I still went by the Stephens' house and got my fill of pussy on a regular basis. Even though Mr. Stephens ... Ted ... did a lot of business travel, I was always welcome at their house, whether one or both of the girls was home or it was just Mrs. Stephens ... Amy. On more than one occasion, I dropped by only to find that Amy was the only one home. She always took me to bed and fucked my brains out every way we could think of ... oral, vaginal, anal ... and then started over again. If either of the girls was home, she would share me with her daughters. The next time I saw Ted, he would talk about how great his next fuck session would be because his wife and daughters would tell him blow by blow about what I had done with them. He never objected to sharing his women with me. Still the very best of times was when the two of us fucked our way through them one at a time.
Mrs. Schowinski was still a regular lover, about twice a month. She was very grateful for my services and I rather enjoyed playing hide the salami with her. So far as I knew, Monica still did not know that I was occasionally screwing her mother.
As the fall semester of my junior year progressed, I added three more female teachers and two female administrators to my list of mates, and it occurred to me that I was beginning to develop a 'thing' for older women. High schoolers were good but older women seemed to appreciate my efforts even more.
Ms. Irene Wagner was a 56 year old white haired spinster, frumpy and rotund and not at all the object of my sexual attention. She was a biology teacher and also in charge of the schools collection of text books, including fall distribution. She requested that I work with her the week before school started to count and distribute text books into the class rooms where they would be assigned as soon as school started. When she first showed me the book storage arrangement, I couldn't believe the chaos ... books piled high all around the room, no shelves in use and seemingly in total disarray. It turned out that she had a sort of cataloging system and she knew where everything was but getting to them sometimes was a problem.
The first afternoon, we were searching for a civics book that didn't seem to be in the right place and we crossed paths in the same narrow aisle, having to turn sideways to pass. She turned her back to me, I faced the same way. However I nudged a stack of books behind me and things began to shift, pushing me against her big round ass. Ol' Mr. Ever Ready perked up and poked her in the butt and she noticed it, especially when I had to lunge at the stacks in front of her to keep from falling over and in a falling domino scenario, she put one of her outlandishly large titties in each of my hands. I couldn't help myself ... I squeezed, causing her to push back and into my now solidly erect schlong.
She was such a sweet little lady and I didn't want to embarrass myself but I couldn't help it either. I pulled on one end and pushed on the other and she said "Mr. Carter, I see the stories about your anatomy are true."
"What stories, Ms. Wagner?"
"The stories going around school are that you have a particularly large protuberance between your legs. And I can feel that it is ... very large. And very hard. Did I do that to you?"
"Yes, ma'am. I can't seem to help it."
"I suppose it will be pretty difficult for you to work like that, wont it?"
"Yes, ma'am. Very painful."
"Do you want to use me to ... relieve it?"
"Yes, ma'am, if you would let me."
"All right, Mr. Carter. Just don't take all day." She slid the skirt of her dress up and pushed her cotton panties down before bending over the stacks in front of her. I worked the head of my throbbing cock between her big globes and found the opening to her pussy and worked it in. Even as I flexed my third leg inside her, I couldn't keep my hands off her huge milk jugs and soon managed to unbutton the top of her dress and unfasten the hooks that freed her. Between my work in her cunt and pinching and pulling her nipples, that little demur ball of flesh came six times before I shot off my wad. As she put her clothes back in place, she said "That was very ... rewarding, Mr. Carter. Now let's get back to work." At first she resisted my claim on her panties but eventually she laughed and signed them for me.
Ms. Wagner didn't mention the incident the rest of the day but when we got close mid-morning the following day, I got hard again. Without asking, I eased her skirt up, found that she was not wearing panties, and she bent over the books without a word. This time I also got a little finger work in around her clitty and she came eight times before me.
After lunch she spotted me looking longingly at her ass, the outline of my erection clearly visible under my t-shirt. Without a word, she raised her skirt and bent over, waiting for me to take advantage of her offer. My cock was in her in less than twenty seconds and her tits were bare and in my hands in another ten. Eleven times she came before I unloaded in her hot box.
The following morning I walked in on her sitting in her big office chair, one leg over each padded chair arm, her fingers working around her clitty and a glazed look in her eyes. I dropped to my knees and pulled her hand away, replacing it with my mouth. My tongue soon had her quaking with orgasm after orgasm until she passed out. When she awoke, I was standing in the same place carefully working my long rod in and out of her cunt. Seven more times she climaxed before she passed out again and then I came. I was at work in the book room when I saw her stirring again. Three times that day I made long trips with the heavy book cart down to the east wing, stacking hundreds of books in nine classrooms. Each time I returned to the book room, she rewarded me with another fuck. She told me I didn't have to do it but I could if I wanted to. I never missed an opportunity.
Each of the remaining days, I fucked the otherwise staid Ms. Wagner at least four times. I decided on Thursday that I would stay late and make sure we could finish the following day. Friday turned out to be a rather light day after that and she offered herself to me seven times and I fucked her all seven, giving her a fresh load with each new fuck. She climaxed a total of fifty-seven times by her count, more than all the orgasms she had ever had in her life before we met, according to her. Late in the day she was in her chair and I lay on her desk facing her. With the sweetest possible smile, she bared her breasts, rolled her chair up to the desk and fed me her titties for nearly an hour while her hand fondled my cock and balls, leading to our seventh and final fuck that day.
Once the school year started, I spent fourth period at a battered desk in the book room, now considerably more spacious than before. Teachers who had returns or needed more texts sent students to me for them but it was pretty slow. Ms. Wagner found time each day to come into the book room and let me fuck her doggy style, getting her off typically three times, sometimes four and me once. Maybe once a week, she let me eat her pussy before fucking her but she was always afraid that if we took too much time we would be discovered. However we were always in the dark foot of the L-shaped room where nobody could see unless we went over and opened the locked door first.
The last week in October, Ms. Wagner asked me if I could work with her at her house the coming Saturday. I cleared it with my mom and was at her house by 8:30 in the morning. I was not amazed to find that every room in her quaint old house was filled with books, some of them in stacks on the floor. However there was nothing on her bed and that's where she planned for us to work, to my everlasting delight. She told me that she was really an inexperienced lover so I taught her things I had learned, like additional cunnilingus techniques including licking her anus, fellatio which she had reservations about but finally decided that she liked the taste of my salty cum, and several positions for vaginal sex. We fucked and fucked and fucked but she would never let me kiss her, at least not with an open mouth. She never would call me Kevin, it was always Mr. Carter so I always called her Ms. Wagner, even though I knew her intimately. Several times that day I spent long stretches sucking her massive titties. Finally I pulled her legs up and rubbed her soles while plowing her cunt with my schlong. She began to go off, over and over and over again. She passed out, came to, passed out again, came to, passed out a third time and came to again, all while her body was progressing through one humongous orgasm. After she came around the last time, I pulled my cock out of her cunt and carefully pushed it into her ass hole. At first she was shocked that I would do that but then she started to cum again and again and again and she forgot what hole I was using as she collapsed into a quivering, quaking mound of hot lustful flesh. When I finally blew off another load into her bowels, I eased out of her, lay down on my side and pulled her close to me. She started crying and I asked why and she said "Because nobody ever cared enough to do that for me before now." After that, I 'worked' at Ms. Wagner's house on the last Saturday of every month.
Mrs. Inez Pearson was the assistant principal and the sponsor of nearly every after-school activity that involved girls, including the cheerleaders. In early November I was running to make my fifth period but the second bell rang just as I turned the corner into the west wing and I still had a long hall to go. Then just as I passed the school offices, Mrs. Pearson stepped out and called like a drill sergeant "Mr. Carter! Come here!" I turned and went back because Mrs. Pearson didn't brook any foolishness, not where breaking the rules was concerned.
"Why are you running, Mr. Carter?" she demanded.
"I .. uh, I'm late." I stuttered. I couldn't tell her that I had spent so much time screwing Ms. Wagner in the book room that I was late getting to the cafeteria and even wolfing down my lunch didn't make up enough time.
"I can see that, Mr. Carter. Why are you late?"
"Well, I was busy helping Ms. Wagner."
She stepped closer to me and I think she sniffed. "Why are my girls always talking about you, Mr. Carter? What makes you so interesting?"
"Uh, I don't know, Mrs. Pearson."
"Come to my office. You can't go to class now without a pass." She turned on her heel and marched through the outer office into her smaller side office. She closed the door after me and went around to her chair. Motioning to a chair at the end of her desk, she said "Come over here, Mr. Carter. Tell me about yourself."
"Uh ... I'm not sure what to say. I think I'm just an average student."
"What are your interests?"
Oh, boy! How could I answer that? Pussy? Girls? Cunt? Booty? Titties? Cumming? "Well, I don't know. I like watching most sports. And I like to study. Biology is good."
"Yeah, I guess. You mean the study of female bodies, Mr. Carter? Is it true what they say about you, that you have done it with more girls in this school than any other boy ... ever?"
"Wow! Do you really believe that, Mrs. Pearson?"
"You know, Kevin, I just don't know what to believe. I do know that I hear your name multiple times every day and the girls are usually whispering in the way they have when talking about sex. Look at me, Kevin. Be honest with me. Are you having sex with several girls in this school?"
I hesitated but knew the cause was lost. If I denied it, she would know and then she'd think I was a liar to boot. I said "Yes, ma'am" in a rather soft voice.
"Why, Kevin? Oh, I don't mean why do you do it. Boys like to get laid by anything with a hole in it. But why do the girls do it? Obviously the girls know that you are having sex with several of them. How many is it?"
"This year? Uh, thirty-four."
"Holy shit! Oh, damn! Excuse me. Did you say thirty-four?"
"What do you do to them that they are willing to let you do that?"
"Uh, Mrs. Pearson, every one of them came to me. Not the other way around."
"Wow! Okay then. What do you have that makes so many girls come to you for sex?"
"Well ... it's kind of embarrassing. I guess it's my anatomy."
"You mean your ...?!?" and she pointed to my crotch. I nodded.
"You've got to be kidding! Show me."
"Mrs. Pearson, I have a rule. I'll show you mine but you have to show me yours."
"What? You think I'm going to risk my job just to see how a boy in the eleventh grade is hung? No way!"
Of course Mr. Ever Ready had popped to attention a few seconds after the conversation turned to sex. I stood now and she could see the outline under my shirt. I stepped up to her and watched her lick her lips. "Go ahead and touch it. It's not fake."
Her hand reached out tentatively and touched the bulb in my shirt just above my navel. There was no doubt about what it was but she let her hand trail down the shaft until she cupped my scrotum and there was no doubt in her mind that it was connected to the bulge that ran upward. In awe she said 'ohmigod!"