Introduction:
Mrs. Simms. She was my English teacher in the tenth, eleventh and twelfth grades. I will never, ever forget her.
Mrs. Simms was in her mid to late forties when I had her. She was about five and a half feet tall, maybe a little shorter, with short dark brown hair and eyes to match. She wore a size one dress and had 34 triple D tits. Pure white teeth and a smile to die for. She could look sexy even if she dressed in one of those Muslim dress things, which she never did. In fact, I never saw her in anything less than a skirt that was way shorter than the dress code allowed, and a shirt that was two sizes two small.
She was very, very popular to say the least. I can’t imagine there were any guys that didn’t jack to her regularly, and it always seemed like more fathers went to meetings than usual. And she held a lot of meetings, let me tell you. Even the smallest “infraction” or “success” would lead to a “parent-teacher conference.” During eleventh grade I got to play voyeur in one of these “conferences.” She rubbed her leg up the man’s leg right there beneath the table as he sat next to his wife. She “accidentally” brushed her foot against the tent in his pants. She later told me she’d made a few guys cum like that, with a nice foot job beneath the table while a wife or girlfriend sat right there. She’d done the same to girls, but only those she felt wouldn’t run screaming to the principle. She could get away with a lot but had nearly gotten fired the first time she did that.
In classes she would act fairly normal. She liked to flash the class, which was nice, and during tests she would bend low over her desk, or look over the front of a student’s desk, giving everyone a great view. Sometimes she wore a bra and panties, but more often than not she didn’t.
There were a chosen few. Every two years she would choose a student from tenth grade, and the relationship would last through eleventh. Then she’d let the student suffer through twelfth grade knowing what some other kid was getting, always hoping that he’d get one more shot at that hot, wet cunt of hers. And it was always hot, always wet.
Everyone knew that she was a bit easy, but no one knew about her Chosen. Even one of us Chosen didn’t know. She told us in the very first week of school, though. The second day our paper would smell like her cunt. Every time we got a handout it would smell more like pussy, and eventually the paper would be crusty with her cunt juice. I don’t know how it went with everyone.
Mrs. Simms asked me to come into her office after school one day. When I got to her office she was in there with Peter Mert, a huge black kid. She had her hand on his lap and she was laughing softly. He wasn’t. He looked grief stricken, in fact. “Come in,” she said. “Pete and I were just saying good-bye.” She moved her hand to his crotch and rubbed it affectionately. I turned to go, but she stopped me. “Stay here, Jake. I can see you want to,” she added, looking down at the hard-on my pants couldn’t have hoped to hide.
“Come,” she said, patting the free chair in her office, also next to her, “sit down while I finish Peter.”
I moved to the chair, eyes wide and mouth open, as she opened the jock’s zipper. She had trouble fishing out his cock, so she ordered him to stand. He did, pulling his pants around his thighs as he did so. He was huge, mostly thick. His cock glittered with pre-cum, which she moved her fingers to swirl around the bulbous head. “I like to choose one every other year,” she explained, turning away from him. Her hand movements seemed to be on autopilot.
My eyes were still locked on the hand working on Peter’s thick cock. Her fingers tightened noticeably. “I want them to be able to focus Senior Year, though, so I let them go, choose a new one.” Her other hand she moved to my knee. “This year I choose you.” I glanced up from the black kid’s lap to his face. I could see the jealously. I swallowed nervously. “Ignore him,” she ordered. “He’s old news. You’re the new model.”
The hand on my knee rose to my chin, forcing me to face her. She leaned forward to kiss me, pressing her tongue between my lips. Peter moaned slightly as her hand left his cock, if only for a moment. “I’m sorry, Petey,” she said, reaching back around to pull on his dick again. She didn’t look at him still. She was still looking at me. “You need to get a girlfriend, of course.” She looked over my shoulder at the corner. “It’s much more fun that way.”
“Wha- uhm, what do you mean?”
“We’ll, you can’t talk, of course. That’s rule one.” She was jerking Peter’s cock harder now, faster, so when she asked, “Do you remember the second rule, Petey?” he gave no response. “Of course not. Silly little Petey.” She squeezed his cock hard, forcing precum from the tip. “You have to do what I want, when I want. That’s rule two. I don’t want to get bored. You don’t want me to get bored.” I nodded stupidly. “Actually,” she said, “those are the only two rules you really care about right now. Maybe more later.” I nodded again.
Her hand was moving toward my lap as she spoke. My breath was getting faster, shallower. Mrs. Simms’ smile was perfect. “I don’t know what you used to get in English, but you can be sure of an A from here on out.” She winked at me. “And I,” she finished, her hand grabbing my cock through my jeans, “will make sure you learn other things.” She pressed on my cock hard, pushing up. I think I was harder than I had ever been before.
My teacher moved both of her hands to my fly. A quick look showed me Peter’s look of pure hate. “Oh, don’t worry about Petey, he can handle himself.” She giggled girlishly. His hand reached for his cock, but she said, “Don’t do that!” He stopped like a deer caught in the headlights. “I know you like to jack off, but you can wait to do that at home or something.” Her hands were cold on my cock. I’d never felt so good and that was before she started moving her hand on my cock. She just used one. She reached back once more, then, and started to tug her former toy’s hard-on.
“W-why me?” I asked, barely able to form the words, let alone get them to leave my mouth. I had tunnel vision by this point, unable to really see anything other than the woman’s lips and the way her tongue slid along them. She was moving Peter’s cock far faster than she was moving mine, but I felt ready to explode already. I couldn’t imagine how he was holding back.
“Last time was big and black,” she said, glancing over her shoulder at him. “This year, I decided to go with whoever was on the bottom of the stack of papers you turned in on day one. That was you, lucky boy-toy.” Her hand tightened around my cock. It felt like a cold, velvet vice. To quote the song, ‘it hurt so good.’ Mrs. Simms pulled her hand off Peter’s cock once again, putting it in front of my face. “Spit,” she ordered. “He really likes when someone is slobbering on his cock, don’t you, Petey?” When no immediate answer was forthcoming she looked over her shoulder once more. “Don’t you, Petey?”
“Yes, Mrs. Simms. Y-yes, ma’am.”
She turned back to me and smiled that perfect smile. “What do you like, Jakey?” She was squeezing hard again, forcing pre-cum out the tip of my cock with each stroke then rubbing it around the head, only to repeat the process. “Do you like a good, long hand-job?” I opened my mouth to respond, but before I could, she asked, “Or maybe a nice blowjob?” I think I made an affirmative noise, but I’m not sure. “Petey here, he was boring. He liked fucking. He had experience before me. I like virgins better. You’re a virgin aren’t you, Jakey?”
Mrs. Simms leaned forward to kiss me again, forcing her tongue between my lips again. When she finally pulled away I tried to lean forward, but she was too fast. “You could be a voyeur, though… or maybe you like men? I saw the way you were looking at Petey’s cock when I started jacking him. You liked that, didn’t you? Seeing my small white hand on his big, fat cock? Look at it now,” she said. When I didn’t do so immediately she squeezed my cock extra hard. “’Now,’ I said.”
I did.
Her hand was moving fast, his cock slick with my spit and his own precum. He was humping up with his hips as if trying to fuck her hand. “See? You like it, Jakey, I know you do. He does, too. He likes when people watch. He likes lots of new things.” Again she leaned forward, and I closed my eyes, expecting a kiss. Instead, she whispered in my ear: “You will, too. Keep watching.”
Her hand was moving so fast I couldn’t keep up with it. I can’t imagine how she was doing that without seeming to pay attention at all.
Her lips were still next to my ear. Each breath she took I heard, and she could hear mine. I was so close to cumming. Peter was too. I could tell, the way he was desperately trying to fuck her fist. “You want to see him cum,” she asked, “don’t you? Want to see his big cock explode in my hand?” She was whispering so low I could barely hear. I could barely hear above the blood pounding out of my head directly to my dick. “Do you want to see white cum shoot from his big black prick? Want to see how high it shoots, how much of my hand it covers? Want to see my lick his warm, salty cum off my hand? Or maybe,” she loosed a giggle, “maybe you’d prefer I make him lick it off.”
I was staring at the tip of his wet, mushroom like head when he exploded. He let out a low groan that sounded almost like a cry of sorrow. Mrs. Simms must have felt him nearing his climax, because she had aimed his cock so that his jizz spewed up to his face, catching the underside of his jaw and leaving a trail down his shirt to his stomach. The second did likewise. She kept pumping. I don’t know where the rest of his cum landed. I think it was the “oops,” she whispered in my ear when he first came. Hell, maybe it was his cumming no more than a few feet from me. Whatever it was, I came harder than I had ever cum in my life.
I thrust up in her fist, and she relaxed her grip slightly, allowing me to spew my load. My had moved my cock so that it was pointed slightly to the side and away from me, toward the low table we were sitting at. She kept pulling my dick, encouraging me to release cum. My eyes were closed, I couldn’t breath. I remember seeing flashing lights in my head.
When I finally regained control of myself, she had leaned back away from me. “Oops,” she repeated. “You made a little mess.” She was stroking us both still, slowly, steadily. Both of her hands, both of our crotches, were soaked in loads of fresh cum. His cock, I noticed, had very little hair on it, and the black boy’s cum was pooling at his hips. I had never shaved, and my jizz-soaked pubes were stuck to my skin. I knew from experience that would be a bitch to clean later.
“Okay Peter,” she said, finally looking at him once more. “Thank you for cumming.” The teacher wiped her hand on his exposed leg, covering it in his own cum. “Remember,” she said once her hand was mostly clean, “if you’re a good boy we might be able to do this again some time.” She turned back to me, winked, and then returned her attention to him. “Leave,” she snapped. “I’m finished with you.”
“But Mrs. Si-“
“No buts,” she insisted, frowning at him. “Or cunts, if I know your girlfriend.” His girlfriend was known as being very faithful to her virginity. How he had come by her still amazes me (although they did break up not long after). He still didn’t move. She squeezed my cock one last time, covering her fingertips in my cream. She licked it off gingerly, then shoved the hand under his nose. “If you’d like I can feed you some of Jakey’s cum. Is that why you’re waiting?”
His head lashed away, and the chair soon followed. “No,” he said, yanking his pants up. The look on his face told me I would probably be dead in less than a day. Maybe the minute I walked out of the office.
“No?” I could see that she arched an eyebrow.
“No, Mrs. Simms.”
Peter seemed about to say more but thought better of it. “You have a little something…” She touched her chin, then rubbed it in by trailing a hand down her chest and stomach, “there.” She then reached out, rubbing his cock through his pants again. A small stain appeared where his cum had been gathering and I saw his cock expand again. “Give me a kiss before you go,” she said. The beauty pointed at the cum I had managed to get on her cheek. The hopeful look turned to one of disgust, but he did what she asked. When he pulled away, the white cream was gone. “Okay, go away now.” She pushed one of her fingers, covered in my jizz, into her mouth as she turned away dismissively.
Peter turned and stalked out of the office, slamming the door behind him. “Such an angry young man,” my English teacher said, putting another finger into her mouth and sucking it clean. “I suppose you would be too if your girlfriend didn’t put out.” She laughed. Another finger. I was watching her lick my cum off her hand after she had just jacked me and a senior off simultaneously! Had that really happened?
I looked down at my cum-covered stomach, the pubic hair stuck together, my cock flopped wetly to the side. It had! “I… I don’t under…. Stand,” I managed to get out. I was still over-awed by the view I now had of my cock.
She was finished with her hand now, and moved around the table. She didn’t answer my question. Instead, she bent low over the table and started to lick my jizz off its surface. She watched me as I did this. I watched her, even more in awe. She was licking my cum off a table. By the time she finished I was hard as stone again. I was hyper-focused on her mouth again. I imaging stuffing my cock in, thrusting hard and fast until I exploded into her mouth filling it with my seed.
Oh god, how I wanted to.
There was a knock on the door, and I knocked my chair over trying to get up, to pull my pants closed, and to hide what had happened. I didn’t realize until she said, “Come in,” that she had taken out one massive, grapefruit-sized tit and was gently rubbing around the nipple. My jaw dropped. Mrs. Glitzke entered and didn’t seem to be surprised by the gratuitous display of illegal behavior. Was she in on it too? “Hi.” My teacher smiled and walked around the table. “This is my new toy.”
She seated herself behind the desk in her office. Using her firm legs to slide the chair out from behind it, I got a beautiful view of that beautiful, hairless cunt. It seemed red, almost swollen with anticipation.
I looked between Mrs. Simms pussy and Mrs. Glitztke. Glitzke was our principal. She was getting on, maybe mid-fifties with an almost schoolmarmish appearance. Apparently just for show. She seated herself in the chair next to me, the one recently vacated by the teacher. I could tell she was uncomfortable being there. She refused to look at me. So I turned to stare at the cunt splayed before me.
Like all the other guys in school, I had seen that pussy before, but now I could really focus on it. Her clit was engorged with blood, sticking out from the folds of her pussy obscenely. It looks like a mountain range set between two hills. “What are you looking at, Jakey?” Mrs. Simms let out that high giggle again. “Look, Mrs. Glitzke, he’s interested in my hot cunt. What do you think he’s thinking about?” Another giggle. There was no response from the older woman.
One of the teacher’s hands snaked down to her pussy, and her fingers shoved the massive clit one way then the other. She used the same hand to rub around her nipple then said, “Did you know I had a baby over the summer, Jakey?” I shook my head. I still wasn’t looking away. I wanted to know every bump, every perfect imperfection of that pussy. I could smell it already. “Yeah. Come here, Mrs. Glitzke.”
The principal dragged her chair until she was next to the spread-legged Simms. She pulled the principal’s head toward her tit. I finally tore my gaze away from the pussy to look at the obscene display of principal suckling at teacher’s tit. “My doctor said I had to make sure I don’t let my baby’s milk spoil in me, and since I’m here all day I have to make sure there’s some way…” She pulled the other woman tighter against her firm, flat stomach. I couldn’t tell she had ever had any children, let alone one over the summer. Mrs. Glitzke was making sucking sounds and Mrs. Simms let out a low purr. “Just like my baby.”
“I-I still don’t understand,” I said. “I mean, uh…”
“You don’t understand why babies – and apparently principals – need to suck on a nipple?”
“No, I mean, I … I mean…” I struggled to put the question to words.
She laughed. “I know what you mean, Jakey. Just go along and enjoy the experience. Just remember the two most important rules, otherwise you lose everything.” She grinned, then winked at me. She was about to say something when instead she gasped, the grin spreading. “Mrs. Glitzke! Are we teething, Mrs. Glitzke?” She winked at me again, and then returned to the previous subject. “You’re my boy-toy for the next two years,” she explained. “I’m going to show you everything. And then some.”
“Mrs. Glitzke is going to make sure we don’t get in trouble so that she doesn’t get in trouble.”
“What do you mean?”
Mrs. Simms shrugged my question off. “You need to get a girlfriend, though. That’s your very first homework assignment. Not,” she added, raising a finger, “that I won’t give you in-me assignments.” She laughed, and I tried to force one out. It came only weakly. “Take out your penis,” she said. “You know you want to.”
I didn’t, instead looking at Mrs. Glitzke.
“Tsk, tsk. You’re worried about getting in trouble from a principal sucking my baby’s milk from my nipple in a school office? While you stare at my cunt that obviously needs to be stuffed? After watching me suck your cum off my hands and jerk off last year’s toy?” I couldn’t see any argument to make, or why it mattered, so I did as she asked, opened my fly and leaned back to pull out my dick. “Mmm. Looks tasty. Don’t you agree Mrs. Glitzke?” My teacher pulled the suckling woman away, holding her head so she could stare at me. She refused to look me in the eye.
The old woman had milk dribbling down her chin. Despite obvious embarrassment she couldn’t seem to take her yes off my hard cock. After a long minute Mrs. Simms released my principal’s head. “Thank you, Mrs. Glitzke. I appreciate your help.” Turning to me, she added, “Mrs. G likes all sorts of white cream. You’re dripping, Holly.” A finger shot up, pushing the milk back toward her mouth. Mrs. Glitzke opened her mouth and licked the finger submissively. “Maybe you’d like to taste Jakey’s some day.”
Pulling up her top once more, she smiled at me. “I think Mrs. Glitzke has a meeting to go to,” she said. Her hand slid to her fellow teacher’s knee, then up until she was touching the other woman’s pussy through her slacks. “Wow,” she said, seemingly enjoying the principal’s discomfort. She’d enjoyed Peter’s too. “Look at that stain,” she said. I did. “And I bet that smell isn’t all me, is it?” Mrs. Simms giggled, covering her mouth. “You should probably go to your meeting before you get any wetter…”
When she stood I saw that her pants were wetter than I had thought at first. I think she liked it. Her eyes were downcast as she left the room with a stiffness equal to that of when she had entered. Unlike Peter, she closed the door very softly.
Once the door was closed Mrs. Simms pulled her chair toward me. “Take them off,” she ordered, “now.” I hesitated, and she repeated, “Now!”
I leapt to comply. My pants were around my ankles in a flash. I sat again, and she spread her legs wide apart. One foot stayed on the ground, but she kicked off the shoe of the other and placed it against my cock. “So,” she said casually, “what do you think?” Her foot moved up and down slowly, the sock slightly harsh against my skin. She was getting cum on it. “You’re my new toy. I’ll get to play with you whenever I want.” She smiled. It was a perfect smile.
“I, uh… can’t complain…”
“I didn’t think you would. No one ever does.” Her foot was rubbing, drawing pre-cum out of me. Every time her sock came to the head of my cock I jumped slightly. “I’ll fuck you,” she said. “I’ll suck you. And I’ll do… more…” She was still rubbing. It was distracting, to say the least. “I like the thrill of nearly getting caught. I like knowing that my husband thinks he knows about what I do but can’t begin to imagine.” Her smile turned mischievous. “I love the taste of cum in my mouth as I teach.” She was speaking in a harsh whisper now. “I love watching the boys in the back rubbing themselves, thinking I’m not paying attention. I love how the girls try to hide their jealousy. She leaned back, continuing the foot job. “What do you like, Jakey?”
I didn’t know how to begin answering. I was a virgin. I mean, what the fuck was I supposed to say? I couldn’t even admit to liking a blowjob. A hand job, yeah, but I knew there was so much more. I liked weird shit on the internet, but that was different. “Do you just want to fuck me, Jakey? Boring old fucking? I get that from my husband. Once a week like clockwork.” She yawned mockingly. “I could suck you off, give you a blowjob?” She moved her toes so she could grip my cock with them. “I know you like a hand job,” she giggled, “and it looks like you enjoy a foot job.”
“Do you like more…. unusual things?” One hand moved to her pussy. She started to rub it, one finger to either side of her massively engorged clit. “Do you like this?” I nodded dumbly. “Yeah?” My teacher’s voice seemed huskier now, sexy. I nodded. “I thought you might. “And you want to stick your cock between my breasts, don’t you? Fuck them?” I swallowed hard. I couldn’t believe I was hearing this. “Are you going to fuck my titties until you cover my face in your cum? Maybe let me drink it right from the tip?” I moaned. I could imagine covering her face in my spooge. I wanted to, right then and there.
She was still rubbing my dick with her foot. “You want to make a baby in me Jakey?” My cock leapt. I was amazed I didn’t come tight then. “Oh, you do,” she said. Again that golden giggle. “You want to fuck me nice and hard don’t you, fill me with your baby-making seed, huh?” She was moving her foot faster. My dick ached.
Suddenly she stopped. “Well, I should get some work done.” She didn’t stop pleasuring herself, I noticed. I was so incredibly hard and I knew without a doubt that this time I would be taking care of myself this time. She slowly pushed herself back toward her desk, watching me watching her finger her cunt. She had a little smile on her face. My mouth was dry. “And you should go home and… take care of that.”
She was behind her desk by then, with just her legs poking out. I could imagine that I saw her fingers still moving, but I don’t think I actually could. God, how I wish I could.
“Oh,” she said. “Here.” She tossed a box at me. I was too slow to catch it, and it smacked me in the head before falling to the floor. It was a box of condoms. “I want you to fill those by Monday,” she said. “I guess that’s homework, too. Bring them to me before your first class.

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