A story between a female teacher (Ms. Whitman) and her sexual encounters with her male students.
I always knew that I liked young boys. When I was a little girl, I had crushes on boys older than me and into my teens I had crushes on boys my own age. As I reached womanhood I realized I loved boys that were younger than me, specifically between the age range of 11-15. Anything younger was typically too childish for me and anything older was just too typical of boys trying to become men. My name is Jenna Whitman, by the way, but most call me Jenny. I have long blonde hair, blue eyes and I’m about 5 foot 8 and weigh about 120 pounds. My tits are on the larger side, but not too big and I always try to stay clean shaven on my pussy. I try to keep my tan up, but sometimes I simply don’t have the time.
I lost my virginity when I was 15 and I lost it to a friend of my brother’s who was 2 years younger than me, making him 13. Greg was his name and he was so damn cute. I’ll get to that story later, though. I blossomed quickly and was pretty popular in school, so not to toot my own horn, but most guys wanted to get with me. Don’t get me wrong, I was no slut, but I did have my fair share of sexual encounters. Looking how I looked, getting Greg was no trouble at all.
By the time I graduated high school, I realized that the perfect job for me would be to become a teacher. I’d be close to all the boys I could imagine and not only that, but educate my country’s youth. I went to college and got my teaching degree and by the time I was 23 I became a teacher. Don’t ask me how; I don’t even know how I didn’t even start as a substitute at first. My first and current teaching job is at West Midland Middle School. I quickly became the teacher that all the boys had crushes on and honestly was not much of a surprise to me. You may call me arrogant, but I’m simply very self-aware of the affect I have on the male gender.
Since I began teaching my goal was obviously to shape the minds of children, but also to get my fill of all of the boys I could get. Each year I would typically have 3 to 4 boy lovers. We’re going to start this off with the very first boy I ever had sexually as a teacher. Charlie was his name and he was a knockout. He was in the 7th grade (which was the grade that I taught at the time) and was just shy of 13. He was just about average height for his age, maybe slightly shorter, had short light brown hair and beautiful brown eyes. He wasn’t very popular, but he was by no means a nerd or an outcast.
It was the first day of school on my first day as the new English teacher. As I expected, nearly all the boys had their jaws dropping over me. But for some reason, one boy stood out to me and that boy was Charlie. I went down a list of names for the attendance and after all the boys tried their hardest to say the word “Here” in a cool manner after I called their names, I learned Charlie’s name. I don’t know exactly what it was about him, but I knew Charlie was going to be my first boy at this school. Over the weeks, I learned more about Charlie as well as all of my students and watched him intently. I pleasured myself so many nights to the image of Charlie, but I couldn’t rush it. I had to make my mark at the school as a professional and one who could be trusted before I tried anything.
I went down to the gym at one point during the day because I saw on Charlie’s schedule that that was the period he had gym. I watched him play volleyball with all the other boys and it was such a sight. As soon as I entered, all of the boys tried their hardest to look cool and win the game, but my eyes stayed on Charlie. Watching him in his shorts being athletic was so satisfying. Before long, Charlie as well as a few of the other boys started taking their shirts off as it was hot on this particular day not to mention their game playing. That was my first look at Charlie’s body. He was a bit on the skinny side, but I could still see he had quite the muscled physique. I practically drooled over him and at one point he made a very lovely smile at me and I did my best to give a sexy smile back to him. I ended up staying the whole period watching Charlie and the rest of the boys play volleyball. By the end of the game they were all covered in sweat and ran into the locker room. When Charlie passed by me he gave me a smile and I said,
“Good game out there, Charlie. You were really good.”
All the other boys gave him a pat on the back or a little punch in the shoulder to congratulate him on the compliment he just received from me. Oh, to go into that locker room and just watch all the boys, especially Charlie…
Over the next couple of days, I had been giving Charlie some signals that I liked him better than anyone else in the class and he seemed to be catching on because he was always giving me a shy smile during class. After my class session with the class that Charlie was in, the bell rang and I dismissed the class.
“Charlie, I’d like to speak with you for a moment.” I said.
“Okay!” Charlie said quite enthusiastically.
After all the other children had left, I closed the door and sat on my desk. Charlie then developed a worried look on his face.
“Am I in trouble?” He asked.
“Oh, no, Charlie. Ha ha.” I replied. “I just wanted to let you know that you’re doing very well in class.”
“Oh okay, good.” Charlie said relieved.
“Yes. Your last paper was excellent.” I said as I rubbed my hand down his left arm.
“Thanks a lot, Ms. Whitman.” Charlie said clearly enjoying my touch.
“Don’t tell anyone Charlie, but you’re my favorite student in class.” I confided.
“I am?” He asked very enthusiastically.
“Absolutely.” I told him. “And because you’re my favorite student, when we’re not in class, you can call me ‘Jenny’, okay?”
“Okay, Ms. Whi---, I mean Jenny.” He said.
“You’re such a smart and cute kid, Charlie.” That threw him off and he swallowed hard. “You must have a girlfriend.” Although, I really hoped not.
“N, no.” He said.
“Really? How could a guy as great as you not have a girlfriend by now?”
“So there’s no girl in school whose lips you’re kissing?”
Charlie just shook his head.
“Well, here’s a little present for being such a good student, then.”
I moved in close to Charlie and place my hand ever so gently on his firm chest and kissed him on the lips. It wasn’t a terribly long kiss; only about 3 seconds, but it was magical.
When I leaned back, Charlie still had his eyes closed for a moment. I ran my finger down the side of his face to bring him back to life.
He opened his eyes and was brought back to reality.
“Well, those girls don’t know what they’re missing because that kiss was incredible, Charlie.”I told him.
He smiled and asked, “Really?”
“Oh yes. In fact, I enjoyed that a lot. So, if you’re up for it and keep your grades up, every day after class, you and I can share a little secret kiss.”
“Yes!” He practically shouted.
“Well then, I guess I’ll see you tomorrow.” I said to him as a rubbed his chin with my thumb.
The next day I was so excited and ready to give Charlie yet another kiss. He seemed to like my advances and I was obviously enjoying it also, so I figured I’d step it up just a little. I tried my hardest not to give Charlie any extra attention as not to arouse suspicion, but I kept seeing him stare at me and give me smiles obviously anticipating another long awaited kiss. I was just as excited, but I did my best to hide it from everyone.
Eventually the bell rang and class was over. Charlie took his time getting his things ready and by the time he was done, the rest of the class had left the room. I went over and shut the door and went over to Charlie. I couldn’t resist, I went up to him and kissed him straight on the mouth with my hands around his neck. This kiss was much longer than the previous one. Charlie had his hands awkwardly sort of hanging in mid air unaware of what to do with them, so I gave him some help. I guided his hands to my hips and returned my hands to the back of his neck. At one point, I couldn’t help myself and slid my tongue gently into Charlie’s warm, wet mouth. He eventually got the drift and shyly entered my mouth with his tongue. His mouth was wonderful and the thought of someone walking in at any moment turned me on even more.
Charlie was so sensual with his kiss and seemed to be a quick learner. I then hooked my right leg around the back of his right leg and ran my hand down the side of his face all while continuing this magical kiss. Charlie was able to show me how eager and excited he was by his little cock beginning to press through his shorts and into just below my pussy.
I broke the kiss and said, “Well, looks like someone’s enjoying himself.”
“Oh, I’m really sorry.” Charlie apologized. “It just happened, I didn’t mean to.”
“No, no, Charlie. It’s alright. You must think I’m very pretty to get THAT big right in front of me.”
Charlie just turned his head, blushed and said, “Yeah, I do. Sorry.”
“Charlie.” I said as I turned is head back to me and looked into those beautiful brown eyes. “It’s alright. I take that as a compliment.”
He smiled at me.
“And since it’s my fault your little friend is here, it seems only fair that I should be the one to get rid of him.”
Charlie then got a shocked look on his face and was frozen.
I walked over to my desk and took a pen and a post-it note out from the drawer and wrote down my address.
“I want you to ride your bike to my house tonight at around 5:00 and I’ll take care of your little friend.” I handed Charlie the paper. “I’ve seen you ride your bike, so I know this won’t be a problem.”
Charlie was still somewhat frozen so I gave him one last peck on the lips and with a wink said, “See you at five.”
The hours agonizingly went by slowly while I waited for 5:00 to occur. I readied my house and myself for Charlie. I dressed myself in black lace bra and panties and put my regular clothes on over them so Charlie would have a real treat when he finally undressed me. I wanted to masturbate so hard when I got home, but I had to wait for Charlie to give it to me good.
Sure enough at 5:02, I heard a knock at the door and practically ran to the door. I opened it and there was my little man standing there a little sweaty from the bike ride over.
“Well hello, Charlie.” I said.
“Hi, Jenny.” Charlie said with a smile knowing that I preferred when he called me by my name.
“Please, come in.”
Charlie entered my house and eyeballed the place for a moment but turned around when he heard the door close behind him. I grabbed him and stuck my tongue into his mouth with force. I couldn’t hold it in any longer. Charlie placed his hands on my hips knowing this was allowed territory for him, but I took his hands and placed them on my ass. I ran my hands through his hair as our tongues danced wildly in each other’s mouths.
I removed my tongue from his mouth and whispered into Charlie’s ear, “I’ve wanted this so long, Charlie.” I then ran my tongue around his ear and right after that, Charlie’s little friend appeared again sticking me right in the leg.
“Let’s go up to my bedroom, Charlie.” I took Charlie by the hand and guided him to my room.
We entered my room and I gently pushed Charlie on his chest to sit down on the edge of the bed and gave him a peck on the lips.
“I’ve been watching you, Charlie.” I told him as I slowly removed my shirt.
“Since the first day of school, I knew you were the one who was going to give it to me good.” I dropped my shirt to the floor as Charlie swallowed very hard. “You’re the perfect guy, Charlie and I don’t know how you don’t have a girlfriend, but I’m going to do what a girlfriend does.” I began removing my skirt.
Charlie watched in awe as I removed article of clothing after another. When I was down to nothing but my bra and panties I went in close to Charlie and licked his bottom lip up to his top lip. Charlie then licked his lips to get any part of me he could into his mouth.
“Stand up, lovely.” I told Charlie and he did as he was told. “You’ve gotten to look, so it’s only fair if I get to also.” I began removing Charlie’s shirt from his body and over his head. I stared in awe at Charlie’s fit, yet slightly skinny body and ran my fingers down very small, but surely forming abs. Charlie shuddered.
“Mmm…” I said seductively. “Delish.”
I then hooked my thumbs into the waistband of his shorts and removed them as well. Charlie and I were standing in front of each other wearing nothing but our underwear.
Charlie seemed to be in a trance and wasn’t saying anything, so I was the one who spoke. “Go ahead, Charlie. Take off my bra, it’s easy.” Without a moment’s hesitation, Charlie reach around me getting very close to my breasts and unhooked my bra after a few moments of fiddling. It fell to the floor and for the first time, Charlie gazed upon my tits with a very sexy look in his eyes. Charlie knew this was his prize and he was going to get it.
“Squeeze them.” I told him.
He very weakly began to hold his hands up to my breasts, but I couldn’t bear the weight so I pulled his hands into them for him. He then gently began to squeeze my breasts and it was like a feeling I never felt before.
“Oh, Charlie.” I moaned. “How are you so good at this? You squeeze my tits perfectly.” Although it was true, I wanted to give Charlie as much confidence as possible. While still squeezing, I gave Charlie another light kiss on the lips.
“You ready to see what you’re gonna get tonight, Charlie?” I asked as I removed his hands from my tits.
All he could do was nod his head all the while staring at my tits.
I turned around, hooked my thumbs into my panties and slowly pulled them down. I turned around to see Charlie staring at my now bare ass and he was harder than he had probably ever been in his life. I wiggled my ass to give Charlie a little show and the look he got turned me on so much. He has this look of sincere lust in his eyes. I guess I had been teasing him a bit too much and I too wanted my fill. I turned around and gave Charlie a look at probably the first pussy he’d ever seen in real life.
Knowing what I was planning to do that day, I was clean shaven for him. I swear Charlie almost drooled over my pussy.
“Do you like, Charlie?” I asked.
Charlie nodded not taking his eyes of my body.
“Do you think I’m beautiful?”
He nodded again as this was all he was capable of doing at this point.
“Charlie, you’re so sweet.” I said as I embraced him into a hug.
This was no ordinary hug. Charlie’s face was right in the middle of my tits and his dick was pressing into me very hard with his hands on my bare ass.
“Before we get to the real stuff,” I told him. “We better start off with something that’ll get you off quick so you can last longer when you’re inside me.”
I knew boys couldn’t typically last very long, especially on their first time and I wanted our first time to last for a bit, so I had to get a load out of him first.
I kissed Charlie with some tongue at first. I then ran my finger down his torso as I got to my knees. He shivered as I made my way down. Charlie’s boxers were going to rip from his erection if I didn’t remove it soon, so I slowly pulled them down. When his dick escaped, it sprung up and smacked against his stomach. I could already tell he was on the slightly larger side when I saw his dick through his boxers, but seeing the actual thing with my own eyes, it was so beautiful.
He was cut, which was common, his head was very red from it being filled with blood, his balls didn’t hang low nor were the tight into his body, he had a little bit patch of pubic hair above his dick and a sparse amount of ball hair topping it off with a nice, little vein running along the underside of his 12 year old dick.
“Very nice, Charlie.” I told him right before I gently pushed him back onto the bed so he was lying down.
Here we were; a 12 year old student and 23 year old teacher naked and horny together getting ready to have sex. It was hot thinking about it that way. I moved up so I was on the bed with Charlie and whispered into his ear, “Don’t worry, let me do everything.”
I kissed his cheek and went down to his dick. It was on the larger side, but I knew that I was going to be able to take him in totally. I grabbed his dick and Charlie quivered with lust. I giggled a little at how horny he was right now. I then kissed the head of his dick with so much love. Charlie seemed to have to get used to everything but I was horny and so was he, so I just dove in. I took Charlie all the way into my mouth so that his dickhead was at the back of my throat. It felt so nice for me, but it seemed to feel even better for Charlie since he was moaning very loudly with pleasure.
I knew he wouldn’t last long at all, so I tried to do everything I could to make a blowjob good as quick as possible. I got off his dick and licked all the way up and down it a few times. While jerking him off, I licked and sucked on his slightly hairy balls. I reached my left hand up to his torso and ran my fingers gently along his little abs and sucked him for all his worth while playing with his balls with my right hand. I continued this for about 45 seconds before I could sense Charlie’s orgasm coming.
Charlie began trying to speak but all he could actually get out were a bunch of gasps and hyperventilating. Charlie’s seed ran up his dick and shot its way into my mouth. He tasted so goddamn good. At that age, even though it’s watery and thin, there’s a lot of cum. And boy, did Charlie cum. Not a drop escaped my mouth and I held it all in there while milking the last few drops out of his cock.
I removed my cum-filled mouth from his spent cock and went up to Charlie’s face to show him his own cum. I opened my mouth and sloshed his semen around with my tongue to give him the idea that I love the way he tastes. He watched in awe and I then swallowed every drop while I unintentionally made a yummy sound. I realized there was a drop on my finger so I brought it to my lips and ran it around my lips right before licking them.
“You tasted so good Charlie.” I told him. “And that was quite the load you shot. You must really think I’m hot.”
And for the first time since he entered my house, Charlie spoke. “I think you’re the hottest woman in the world, Jenny.”
Hearing that made me feel so good. I leaned over and smashed my lips into Charlie’s and shoved my tongue deep into his throat. I’m pretty sure he tasted some of the leftover cum from my mouth but I also doubt he cared.
After giving all the love my mouth could give to his, I kissed his chin, down to his neck, his smooth chest, stopping to give each pink nipple of his a little lick. He was already getting hard again, as I figured a boy his age would and as his member regained its length, it was completely aligned with my tits. His now hard cock rested right in between my tits and he attempted to thrust into them.
“Flex your little abs for me, Charlie.” I told him and he did as he was told. It was so cute and hot to see even a tiny bit of abs on a boy his age. As he flexed I ran my fingertips down his stomach muscles and kissed and licked them. They tasted so good and smooth. I loved his hairless body. I then licked his belly button and I could tell he found that a little ticklish.
I was ready for Charlie to lose his virginity to me, but one more thing needed to be done before the magic could happen. I got up close to Charlie’s face while he was still lying down and said, “I think we need to be fair here, don’t you agree?”
Charlie looked confused for a second, but replied, “Yeah…?”
“Then, I think the fair thing for a gentleman like you to do would be to eat out my pussy with those perfect lips of yours. Do you know how to eat out a pussy, Charlie?”
Before he could answer, I saved him the embarrassment of saying “no” by interrupting, “It’s easy, Charlie. All you have to do is essentially make out with my pussy like you do to my mouth, but spend lots of time on my clit with that wonderful tongue of yours. Can you do that?” I rubbed my hand down his chest to give him some confidence.
“I can do it, Jenny.” He said. “And I’ll make you feel as good as you made me feel.”
I kissed him deeply for a moment and readjusted myself so that his face was now buried in my pussy. He instantly began licking and sucking away on me. It felt so good. To think, not more than 24 hours ago, this boy was just a student to me and I was his teacher and now he’s eating out my pussy after I drank a load of his cum. I was so turned on by that thought.
“Oh, Charlie!” I shouted. “You’re a natural at eating pussy! You’re making me feel so fucking good!”
Charlie muffled as best as he could with his face buried in my pussy, “You taste so good, Jenny.”
“Eat me, Charlie! Eat me!” I screamed.
For the first time on his own, Charlie made a move without me telling him to. He reached his arms up while eating me out and grabbed my tits.
“Oh, yeah, Charlie! Squeeze my fucking tits, you sexy boy!”
He massaged me breasts greatly. I grabbed his hands and squeezed with him. He then began rubbing my nipples and I knew I wouldn’t last much longer with all of this stimulation from a 12 year old boy.
“Oh, Charlie! I’m gonna cum, baby!” I let him know. “Get ready for it, sweetie! Here I come!”
And with that, I must’ve nearly drowned Charlie in the amount of cum I made. I don’t think I had ever been more wet in my entire life. I lifted myself off of Charlie and saw his face and hair wet with my pussy juices. It was such a hot image.
“That was amazing, Charlie.” I said as I kissed him passionately. “I know you’re hard, but let’s rest for a second.”