A High School Life to Remember Chps. 1 & 2


It all started when I was just hitting my teen years. Before that I did not know really what it was to masturbate or why boys ever liked girls. Then one day I started finding porno magazines in my dads bathroom, and then came the great sacred crusade in which I would search for pornographic materials at any free moment when my parents weren't around. As time went on, and I found more and more materials, I found that a trend was beginning to set forth. Every time I watched a video, every time I looked through a magazine, I found myself fastforwarding to the scenes with the girls that had the deluxe assets on top. In my early life, this almost became an obsession, as a girl could be so much hotter to me, just by having large breasts.

Of course, right after this early time of my life where I acquired this obsession is right when the girls at school started to gain breasts and started to look like women instead of pre teens that looked pretty much the same no matter what the gender, or at least in my eyes. What I saw that really made a woman was a girls tits; it is what set her apart from a boy. There did seem to be limits to the attractiveness of breasts at too great a size, but even very large ones that others perhaps were not as enjoyable to others I found myself wanting to see.

That leads me up to the present day, I'm eighteen years old and a senior in high school and my name is David. I masturbate almost all the time and I am pretty well practiced at it. I am well practiced at it because I am still a virgin and I have never really gotten anywhere with any girls past the kissing stage. I think I have grown so attracted to breasts that I am almost intimidated by girls that have them and by the breasts themselves. Almost as if they are a holy grail that I should not acquire or touch but only look at.

Soon all of this was about to change.

There is this girl, Helene, whom I have the hots for. She is a gothic girl with black hair that is always styled nicely, usually it is wavy or curly and it goes to about shoulder length. Her clothes always had to how hot she is but she wears quite a variety, sometimes she looks almost preppy and other times she wears fishnets and other goth styles of clothes. She had written a couple of my friends very sexual letters and claimed that she liked the dorky guys, like me and my friends but I think she is just teasing us. The day that I knew I had to do everything in my power to win her over was the day that she wore a corset to school, it was a shiny red and black leather piece, but that wasn't the part that I really noticed, her tits were popping out of that thing like they were balloons being squeezed and about to explode. Her milky white skin and deep cleavage gave me an instant hard on that day.

I was standing there with my friend Mat talking about some new game that we had started playing when she started walking by. I looked over and she was wearing something more preppy today, a tight black sweater with a turtle neck that showed off her assets well. Mat tried his hardest to snap me out of it but I was not having it. She starts staring right at me and I know I have been caught looking at her tits. The thing is, I just keep staring and I can feel myself getting harder and harder, by now my cock has got to be showing in my tight black pants. She just smiles at me and looks down for a brief moment and then keeps walking away, flaunting all that god gave her.

"Dude, you are gonna go blind looking at those things any longer than that." Mat says to me.

"How am I supposed to look away, you can see the size of those tits. They are freaking ridiculous. I mean hell, she has to have like at least appearance four." I laugh and he laughs and nods at my nerdy reference to a role-playing game. "If only I could make my charisma check to get with her."

"Don't you remember that letter she wrote me, she is just a fucking tease, you would be better off somewhere else." Mat retorts as the bell starts to ring for our first classes of the day. "Well I gotta go dude, I'll see ya later."

"Word." After he starts to walk away I can't stop thinking about the sexy woman that I saw and my cock is still hard as a fucking rock. I can't go to class like this, everyone will see this when I walk in, I need to take care of it, now where should I go to do something about it. Not the bathroom, that is just dirty and nasty. There is that little alcove where no one ever travels and there are no classes. I nod to myself and decide to check it out.

Little do I know that have been spotted as someone who is not going to class and I am being followed. The teacher that is following me probably thinks that I am going off to do some drugs or some other equally ilicit and illegal activity. This teacher has to be the hottest teacher in the whole school. She is constantly wearing her blonde hair in pigtails and has fair and smooth skin. I could just imagine seeing her in a bikini, her huge tits just popping out and waiting to be grabbed. Her lips are the perfect shape to suck a cock and every time I was sitting in Ms. Gerard's class, it is one of the only things I could think about. Her legs looked powerful enough to ride a horse and I would let her ride me if I had the chance, of that I am sure. Today she is wearing glasses, which she sometimes wears, I am uncertain if she even wears them for a prescription or just for the style. Her outfit is a plaid mini skirt and her shirt is a white blouse that is cut off at the top, revealing some of her milky skin, and that shirt is surrounded by a small business jacket.

I walk into the alcove and lean against the wall. I start to rub my cock through my pants just thinking about those tits of Helene's. God I would love to suck those tits, I think as I stick my hand down my pants. I start to stroke myself slowly while my cock is still contained, but after a few minutes it becomes difficult to get the proper stimulation, so I unzip my pants and pull my cock out into the cool school hallway air. My cock is by no means huge, but it is definitely bigger than average, and the fact that I trim my hair makes it look just a bit bigger. I start to jack off my cock after spitting on my hand and think about what I used to look at in those magazines oh so long ago. I see my cock sliding in and out of those milky white tits of Helene's and I think of what her nipples might look like.

Ms. Gerard has been watching me this whole time unknown to me. She watched and waited as I entered the alcove and thought she was about to catch me red handed doing some sort of pill or tab, but I certainly did fool her. The sight that came to her was one she was not prepared for. Ms. Gerard had been having issues at home with her boyfriend, apparently she had learned that he was cheating on her with another woman and so she had been quite frustrated recently. The sexual scene before her became even more pronounced as I had pulled my cock out of my pants and let the full length of it into her view. She felt a tingle between her legs that had seemed to grow unfamiliar to her. As I began to moan, she imagined me letting her suck on that dick and letting my cum fly all over her face. Ms. Gerard was a wild woman, she just loved to let the men take control and she loved to be the dirtiest slut she possibly could. She had just started to touch herself through her clothes when her conscience had caught up to her. She had to put a stop to this.

I am so close to cumming, I can feel my heavy load churning in my balls. It is only now that I think to myself that I forgot I have no place to cum. What was I going to do with this big mess I was about to make? Right before I was about to halt myself before I went to the point of no return, I saw her. There is Ms. Gerard, approaching me, staring at me, or more correctly to the point at my cock. Right as she starts to speak out "just what do you think you are...," my cum starts to let loose as I can't help but stare at her beautiful tits. She gasps and as she is so close to me now, she sticks her hand out to catch the remaining streams of my cum in her hand, and quite a handful it is. "Mister, what do you think you are doing? Put your pants back on right now!" She says as I have finished cumming and she holds a handful of my cum. "What would people say if they saw this big mess all over the floor over here? How dare you in our very own school."

I am shocked, I have no idea what the hell I should say. I just saw one of the hottest women alive catch a handful of my cum and then yell at me for it. "I... aaahhh... I," is just about all I manage to get out.

"We are going to have a talk after class is over today, you will report to my room right after the school day is over. Is that understood?" she commands me.

"But I am supposed to meet my friends right after school for role..." I attempt to say.

"I don't want any excuses, I expect to see you at my class room as the last bell is ringing."

I sigh, defeated, "Okay I will be here." As I leave and head to my first class I think about the shocking thing that has just happened to me. My cum is in her hand, it makes me want to masturbate again. My cock stays hard throughout the rest of the day as I can not get the image of the two ladies out of my head.

The rest of the day was spent differently for Ms. Gerard. As soon as I left after our little encounter, she became curious about the cum in her hand. She knew she did not have to do what she had with my cum, but she was so fascinated by the amount of cum that it was all she could do to not jerk my cock off. She not only smelled the cum, but she also tasted it and discovered that it was just about how she liked it to taste and it was the perfect consistency, nice and thick. She rushed back to her room and closed the door behind her, she had no class this block, fortunately for her. She pulled her top out and dropped the cum directly onto the top of her tits. She then began to rub it in and loved the way it shined on them and she vowed that this would not be the last time she saw one of her students cum on her body. Fuck Johnny, she thought, he doesn't deserve me. She began to prepare for her school day, but she spent much of the rest of her day thinking about the mornings encounter.

Chapter 2

What am I thinking? Ms. Gerard says to herself. I can't be thinking about fucking around with a student. I could lose my fucking job, but jesus, my boyfriend is fucking around on me and David is pretty damn hot. What ever happened to good old fantasizing and masturbating? I can do that and I won't risk a thing, but David is coming here after school is over, I wonder what he could be thinking about right now.


It is my last class of the day and I have not heard a single word my teacher has said the whole class. All I am thinking about is my upcoming embarrassing meeting with Ms. Gerard.

I am such an idiot! Why did I think that I could masturbate out in the open like that and not get caught. What if she tells my parents?

Still with this worried line of thinking another line of thinking prevails to rule over my mind. What if she wants me? What if she wants to show me those tits of hers? I wonder what size could they be? I don't really even know what the sizes mean, maybe she has DD boobs, that seems to be what people say when girls have nice ones. God it would be great if she let me grab her pigtails and shove my dick down her throat.

As I have these thoughts, I feel a swell in my pants. I know that there is no way I can hide it as I fidget around in the seat trying to conceal my growing erection. I look around the room and to my horror I see that Cali, the school bitch stares right at it and then at me, and she looks like she is about to laugh and then she cringes. Could this day get any more embarrassing?

The final bell rings and I head to meet my fate.


By the end of the day Helene found herself talking to a good friend of hers on the way to her car in the school parking lot. "Hey, Helene!" she yelled from across the street. It is her friend Cali, she skips school quite a bit and on occasion Helene finds herself there with Cali. Cali starts to come across the street to Helene's car, that she now stands next to as she waves to her friend.

Cali is a red head with freckles and bright green eyes. She screams of Irish descent in almost every way possible. She is wearing her hair in a bandana and she is wearing baggy pants and a big t-shirt, which she usually does because she doesn't like to show off her big ass and DD cup tits.

"Oh my god, Helene. I have to tell you something that I saw today." Helene gives her a quizzical look and awaits the story that probably has something to deal with a drug or cop that Cali has been dealing with today. "I actually went to school today! You won't believe, eeww... the grossest thing that I have probably ever seen." She waits to hear the punch line wondering whether this comment will even be worth her time. "I was sitting in class and I looked over and there was David, and I could see the outline of his cock in his sweat pants. Eeww... can you even think of that, David, what a loser. Those weird alien shirts and stuff that he wears, god, get a hint."

Helene thinks to herself of the description that Cali just gave. I like the guys that dress like nerds, and David, he is fucking hot as hell, he just needs some help to look better. She feels a tingle in her pussy just thinking about being the one to see his hard cock outline in his sweats. She just thinks of it accidentally popping out in the middle of class and watching him jack off for her.

"Earth to fucking Hellie, hello? You in there?" Cali waves her hand in front of Helene's face and finally she looks over and lets out an answer.

"Oh yeah, that is pretty gross. Those boys of his, the whole dork crowd, they could really use a lesson in style."

Cali returns her statement with, "They always hang out in that corner on the second floor and feel sorry for themselves. Well anyway, can you give me a ride home, I missed my other ride."

Helene and Cali get into her Miata and drive home from school.


I walk in to Ms. Gerard's now empty class room while everyone else happily heads out the doors to go home. I really want to go play some dungeons and dragons with my friends but no, I had to fuck up today. "Ms. Gerard, are you in here?" She comes walking out of the small office that is attached to her class room and waves me back.

"Be a gentleman and close the door on your way in, it tends to be really loud in the halls right when school is out," she says. I close the door to the classroom and head into her office. Oh my god, what if she wants me to close the door because it is locked from the inside and now she wants to have sex with me or something? I start to run role playing scenarios through my head of how I always imagined something like this might happen. When I enter her office I see that she has taken off her little business jacket and has only a tank top on that struggles to hold in her busty assets. I can feel my penis begins to get hard and I quickly take a seat and squeeze my legs together to conceal it.

Little do I know that by doing so, allows her to see an even more defined outline of my hard cock. She has mentally prepared herself to give me a speech about the fact that the act I did is inappropriate at school. Now she finds it hard to ignore my hard cock and her brain and stomach are fluttering with butterflies. She sits down behind her desk and eyes me, trying to re compose herself.

Her hand begins to play with a pencil that sits on the desk and slouches down in the chair a little bit.

"What you did earlier... it is something that you shouldn't do..." she thinks for a moment and says something a little different from what she meant to " the halls." At this point she takes the pencil and moves it under the desk and begins to rub her clit with the eraser through her panties. "Look, everybody does that sort of thing, but you can't do it out there for everyone to see. From now on, if you are at school and you have the urge to do that again, you need to report directly to the nurses office." A slight moan escapes her lips as she moves her panties aside and begins to stick the pencil up her pussy. "I will write you a permanent pass for a medical excuse. Just don't let what you did happen again."

I feel unsure as to what she has planned for me but I decide it is best not to step out of line or question her. If I had only known what she was doing behind the desk, my whole attitude might have changed.

As I leave her office I sigh in disappointment as my fantasies got a little too crazy, but at least she did not shoot me down like I thought and tell my parents.


The next day I show up at school and go to the usual spot we always hang out in the morning. It is a corner of a long hallway on the second floor of the school that has a windowed wall that oversees the track and football stadium. Everyone here are in some way a social reject, but I have brought them all here to band our nerdy might together. We have role playing dorks, anime nerds, really smart kids, and other assorted losers. I see my best friend Matt walking up to our corner and immediately give him the fist, instead of a hand shake of course, that would be too proper. "What's up Matt?"

"Not much bro. Did you hear about Lindsay?" I give him a look of wondering which thing and wait for him to continue. "Apparently she got a boob job done, at eighteen years old, can you believe it? Why would a girl every want fake boobs, I like a nice pair of titties, but that is just fake. Oh, by the way, I got some new werewolf books so we can try that tonight. Too bad you had to ditch us yesterday for a damn teacher."

"Yeah I know, that did kind of suck. Now my character is behind in levels."

"No worries, what did she want anyway?"

I pause for a moment, there is no way I can tell him what really happened? That would be the most embarrassing thing ever, even if he is my best friend. "Oh it was about a school project that I fucked up on; she was helping me fix it."

The bell rings and it is time for our first classes to commence. I say my goodbyes to everyone and then I start to think on my way to class about Lindsay. Fake tits, I want to see them, I bet they look really hot, but they are on Lindsay. That girl has liked me for so long and we did date for a short time but nothing really came of it. She usually wears long sleeve shirts and comfortable jeans, I bet that outfit would look even hotter with a big set of tits underneath of it, trying to find their way out. Her blonde hair has always been one of those shorter cuts that is longer in the front and on the sides than in the back and it is always straight as an arrow. Her glasses are cute black frames that some would call "emo." I get a hard on and immediately fight the urge to go to the nurses office as I am really afraid of what I might face there.


Later that day as I am getting some books out of my locker I see Lindsay walk up. Her hair is shining in the artificial light but I barely notice her glasses or her outfit except for the tight, thin top that she is wearing. As she walks up to me my eyes are drawn to her shapely and perfectly round tits.

"Hi David, I haven't seen you in a couple of days," she says to me as she walks up and opens her arms for a friendly hug. Of course she probably has been planning on torturing me like this since I broke it off with her.

I hug her back, despite the danger of being burried into her chest. "Hi Lindsay, yeah, what have you been up to since I last saw you?" I stupidly say.

"Oh, nothing much, I just went shopping and got these." She smiles and motions down to her boobs. My eyes are drawn there again and she can't seem to keep her mouth closed, she is smiling so widely. "I was hoping we could hang out tonight."

Here is my dilemma, do I go hang out with this busty girl or do I go and play werewolf with my friends. To some this decision might be easy, but in my mind now a question appears. Will this hang out be like all the others with all the other girls where they really just want to hang out, or will it be more. I know playing RPGs with my friends will be fun no matter what. "Nope, sorry, I've got plans." As soon as the words are out of my mouth she seems to lose her edge.

"Oh, well... maybe some other time then. If you ever have time," her voice trails off as she turns around and begins to walk away. Bros before hos, I say to myself a few times to justify my decision.


The evening is just about over. I am departing my friend John's house after a great night of role playing. I might be eighteen but I still don't have my own car, so I start to walk the distance home. It usually takes me about forty minutes or so. When I am about half way home it starts to rain and I curse to myself, not having any way of covering up. Just when I think my luck has run out a car pulls up next to me, its not a fancy car at all, but it is a car. I look inside and see Lindsay in the drivers seat. "David! Do you want a ride?" She yells through the rain.

"That would be great! Thanks, I was starting to get soaked."

"Well, you are lucky I just happened to be in the neighbor hood." She drives for a few more minutes in silence and then pulls the car into an empty parking lot. "This rain is too heavy, I need to stop for a minute till it clears up. You sure are wet," she says as she moves her hand over my thigh. I instantly get a hard on from the feel of her soft hands so close to my penis. She spots it right away as it has grown painfully to its full length in the confines of my pants. It does not help when I look over at her and see her leaned over towards me with her new boobs shoved pretty much in my face.

Lindsay leans in towards me and begins to kiss me; I respond in kind to her advances. I think to myself about all the chances that I might have possibly had lately to get my hands on a busty girl, and here I have one throwing herself at me. I wonder if it would be okay if I touched her tits.

As we kiss more and more, our bodies start to tangle and we pull the seats down. "God, David, you really make me feel really good." I think, now is my chance, but what if she gets mad because of it. I will make a joke out of it.

"Oops, I fell over." I say a line that I stole from Austin Powers. I fall down towards her with my hands at her boob level. She moves her hands into the way and we keep kissing for a few minutes, our faces are rubbing against each other and our legs as well.

The intense make out session lasts for about twenty minutes when I decide to try my luck one last time before giving up. "Oops, I fell over again," I say and try the same manuever as before. However, I find myself shocked as only moments later, my hands are wrapped around her breasts, and I can barely believe that I was so lucky. I squeeze them a little timidly and she moans. I play with them like this for a few minutes before either of us say another word. It is as if we both feel we are breaking some law and we don't want anyone to know. "Can I ask you a question?"

"Sure, go for it," she pants.

"What size are your..."

"Oh these, I am just lucky that my family is both rich and liberal. They are about a 38D now. Thats up from a 36B." She smiles again, her face dripping with passionate sweat. "Do you likey?"

"Yes, I... I really do. Is that okay?"

"Fuck yes!" She says, surprising me.

My hands knead her tits more thoroughly now and in wider circles. Our legs still rubbing against each other, she moves one so that it is massaging my cock, which feels like it is hard enough to burst. I never thought in my life that I would have a chance to do this. Boobs always felt like they would be something I would look at in magazines and never be able to actually touch. Finally, I am doing it. I begin to grow even more bold and I seek out her nipples specifically with my fingers. Being that I am inexperienced and don't wish to show it, I slowly move my hands all over her tits, through her clothes searching for them.

Finally I find her nipples and begin to squeeze them a bit and Lindsay begins to squeal. "Do you want to see them? Without my shirt I mean?"

"Really?" I say in a soft voice, almost not able to believe what is happening to me. "Please, oh please."

She smiles again, seeing that she has total control over me now. "Okay, your wish is my command Master David." She leans up in the car seat and pulls her top off, practically peeling the tight thing off of her skin. As she leans back down I get a full view of her bra covered titties. The cleavage that she is showing and the beautiful lacy black bra makes me want to, I don't know, stick my dick between her tits like I have seen in the magazines before. "Go ahead, feel them now."

I reach over yet again and explore her tits through the bra, rubbing my hands all over. Then as my confidence hits its peak, I reach into her bra with a hand and begin to feel her tits. Much to my surprise they feel very nice, even if they are fake. She moans some more and I feel that I have come to the breaking point. Her leg grinds into my crouch as I begin to pull her nipples inside the bra. It is all so insane to me, I can't control myself; I begin to cum in my pants as a look of bliss comes over my face and she knows what is going on.

"Wow, I didn't think I could do it that well for you. I was hoping you'd last a little longer, you know. So maybe I could play with it."

"I'm sorry."

"You should be. Actually thats okay, I need to get home soon anyway. Oh and I'm sorry to do this to you, but I can't give you a ride home now. I don't have the time."

"Fair enough, it looks like the rain has stopped anyway."

"Thanks for the good time, my hunk."

"Oh umm.. I guess you are welcome... I," seem to have lost my voice. I get out of the car before I make a fool of myself. She waves at me as she drives off. Well now I am farther from home, but at least it isn't raining.

I head home to attempt a full night's sleep, but I know it won't happen since I will be thinking about Lindsay and what happened all night.