Lenny always dreamed of knowing what it would be like to be with her
Lenny hated being such an outcast at school. Fallow State College was nothing like he imagined it would be like. It felt like high school all over again and he once again was the total geek who no one else wanted to talk to. Well except when they needed help with their studies. Lenny was a teacher's aid there while he went to Syracuse University full time. He had a couple of classes he helped with at Fallow during the week to help with his graduate degree. The hardest thing for Lenny was not having the experience of being with a woman. Here he is, 22 years old, on his way to graduate with honors and already being scouted by several Fortune 500 firms and he still's a virgin! Its not like he hasn't tried, girls just aren't interested in a pale, eye glass wearing, chubby geek like him. If only the girls knew how wealthy he would be one day they would be all over him. Maybe just the shallow ones but who cares. As long as they look like a Hawaiian Tropic Model then who cares if they are brainless morons.
Lenny had his eye out on one of the girls already. Her name was Heather and she was in the economics and business class he was aiding. Her papers were horrible and she was down right failing. The sad thing was she had a soccer scholarship she desperately needed to keep. I guess she didn't come from a well off situation. Lenny even heard she was on her own with no family around. She supposedly was living off of the scholarship which paid her tuition and an apartment off of campus. Lenny knew if she lost that scholarship she would be screwed for sure. Lenny always had a hard time concentrating whenever she came in after practice. Her seat was in the front row and her legs were in clear view of Lenny's desk. She didn't look like your average ogre soccer girl. She was lean, slightly muscular but very feminine. Her legs were very proportionate and tan. It was amazing, for a girl who runs around in shorts all day you'd think she'd have a massive tan line from her shorts. Not her. When she crossed her legs, they were smooth and tan all the way up. Her chest was great too. When she'd finish practice she'd strip off her jersey and just wear the classic wife beater tank top underneath. Her breasts had to be at least a full C. The thing that really got Lenny was how incredibly gorgeous Heather was. Her perfect smile and super cute big brown eyes were spectacular. The guys were all over her but she was really devoted to her sport. She couldn't mess that up because she had a dream to play in the professional woman's league. Her coach didn't allow for promiscuous behavior. One incident of that and she'd be thrown off the college team and her chances for turning pro would be gone.
Several months had passed and summer was growing closer. Lenny was really bummed because he knew Heather may not be in another one of his classes the following semester. He was also aware that her grades were falling under a C average. That meant if she didn't pass this course she could very well lose her chance to play on the team. Lenny didn't want that to happen at all but there was only so much he could do about it.
Well one afternoon, Lenny was walking down the hall and stopped to get a soda from a machine. He grabbed the drink and turned around to see Heather sitting on a bench with some other girls. She wasn't dressed in her soccer attire like she usually was. She was wearing a pink tank top which laced up in front. Her legs were unbelievable amazing that day. Heather had a pair of cut-off jean shorts on and they were barely past her ass. Her sandy blonde hair was drapped down her back and she wore these hot pink hoops in her ears. Lenny couldn't believe how sexy she looked. He immediately started getting a hard on. He kept watching as she bounced one of her legs while she talked with the girls. Her hands kept rubbing her legs and he could only image how smooth they were. As Lenny lowered his books to cover his erection, Heather looked over towards him and smiled. Oh my goodness, she noticed me and smiled?! Lenny lost his confidence and walked quickly to class, excited over the fact that she would be wearing that in class. As the older professor got his notes ready for the lecture, Lenny grabbed the class grade sheets and noticed Heather was averaging a D+ in the Economics course. He walked into the teacher's aid office and grabbed the Business course folder and looked up Heather's grade in that course too. She also was getting a D+ in Business which was horrible because not only would she not be allowed to play with those grades but she would be placed on academic probation and lose her scholarship. That means she wouldn't be at Fallow College the next year. Lenny was stressing, he couldn't believe his misfortune, let alone hers. His grief suddenly shifted to joy. Lenny had a plan. He held the grade books and had the power to change her grade without the professor knowing. Now he had to help Heather see the opportunity they both had.
Minutes later, class started. Lenny had already slipped the grade books into his briefcase as Heather walked in and sat down. Wow, her legs were glistening in the light and her cleavage was even more evident now. Lenny was even more ecstatic to learn the lecture was followed by an exam. This would give him a change to ogle Heather while she focused on the exam. She would be oblivious to his leering eyes. Class finally came to a conclusion and the students filtered out. The professor left immediately for a meeting, leaving Lenny in charge of the room. As he started looking over the tests and watching the other girls asses as they walked out, Heather handed her test to him.
"Hi, your Lenny right?"
"Uhh (Lenny was dumbfounded for a moment, totally unskilled n the ways of conversing with such a beautiful woman) yeah I'm the course aid, Lenny."
"I have a soccer match this weekend and the coach wanted me to get an academic advisal slip so she could see if I was eligable. I guess I haven't been doing so well in this course."
"Yeah, let me get your score." (Lenny already knew her score and quickly tried to devise a plan).
(He pointed to her name and showed the penciled in mark of a D+)
"Lenny is that true, Oh shit what am I going to do? Do you think this exam could improve my grade?"
"There's a chance Heather, let me grade it really quick." (As he graded it he already saw most of her answers were wrong. He stalled, not so much because he was afraid to tell her but more because her legs were inches away from his desk. He could tell she just shaved them and he wanted so bad to reach out and feel them up.)
"Heather, I'm afraid your test didn't help you at all."
(Heather started to tear up, she knew she could lose her starting spot and the scholarship. This would ruin her chances to go pro.)
"I got to figure something out. We only have a few tests left and I bet if I do well then my grade can be improved to a C or better."
(Lenny knew there was only two exams left and they didn't count enough to help her grade improve. He lied though and gave her an option)
"Heather I uhh...I can help you with this. I'll give your coach a slip that says you're averaging a C in the course. I'll only do this if you agree to let me tutor you for free. I empathize about your situation so I want to see what we can do to help you better your grade."
"You'd do that for me Lenny? Wow your terrific."
"Yeah Heather no problem. Here's my address. I live near the pier, above a warehouse. Its nice and quiet and I have all the books and texts to help with the class there. Why don't you meet me there tonight around 8pm so we can study?"
(He could barely believe he had the balls to invite her over. He knew if she agreed and met with him there no one would be around to disturb them.)
"Okay great Lenny! Thanks so much, you're such a life saver. This is my only chance, I have to pass these courses. Thanks again, I'll see you at 8."
"Oh and Heather, it gets kind of warm in my place so if you wear something like you have on now that would be perfect. I mean so you won't be too warm or something."
(Heather looked at him strangely and shrugged her shoulders) "Uh okay Lenny, you'd know best."
The rest of the day was a blank, other than the Business class Lenny had to aid in later that day. Lenny couldn't help but gawk at Heather while she concentrated on the class lecture. Lenny started to get frustrated though because he was having a hard time devising a plan that Heather would be trapped in going along with. After much thought, Lenny decided he would film them, get her to take her clothes off and then fuck her on camera by manipulating the situation. He could then use that to blackmail her and get her to do whatever he wanted for ever.)
(8 o'clock came around and Lenny already had a hard on. He couldn't help it, the thought of what he was going to get to do was incredible. Even the thought of such a hot chick coming over to his place was enough to make him hard. And the fact she was wearing what she was wearing was enough to make him cum in his pants. There was a knock at the door and Lenny walked over to the peep hole to check if it was Heather. There she was, still in the same outfit. He stroked his dick as he watched her for a few seconds as she stood there. He yelled out that he would be there in a second as he waited for his dick to stop standing straight up. He opened the door and greeted Heather who was appeared to be a little nervous.)
"Hey Lenny, this is a cool place you got here. Its so quiet and away from everyone." (Heather walked to the window and looked out at the ocean and all the lights on the boats.) "Wow Lenny this is such a beautiful view."
(Lenny muttered low so she couldn't hear,) "Your ass is such a beautiful view."
"What did you say Lenny?"
"Oh nothing Heather, hey come over hear and lets start studying."
(They sat on his bed and opened his books as she sat and listened to his advise. Lenny kept chickening out as he tried to work up the courage to blackmail her. Eventually the conversation switched to her grade point average and what she needed to do to get her grade to a C. As Lenny bullshitted her about the possibility of improving her great, Heather looked down to the grade sheet in front of her. She did the math and realized on her own that even if she aced both tests, she wouldn't be able to pass the course with a C.)
"Hold on Lenny, I just did the math and I swear I wouldn't even be able to pass if I got and A on both exams. You had to have know this!"
"Heather relax...I knew this all along." (Heather stood up and clenched her fists.)
"You did?! Why'd you invite me then? Just to waste my time or what?"
"You see Heather, I have a different idea. I hold the grade books for both courses your failing and I can make your grades a C. I can even make it an A if you want. Its all up to you you see."
"What? What do you mean its up to me?"
"Heather I've noticed you forever. You're the most gorgeous girl I've ever seen.You're definitely the hottest chick on campus..." (Heather waves her hands and stops Lenny from finishing.)
"Wait a minute, if you think I'm going to do anything with you you're wrong. You're disgusting. Why would I want to be with a chunky slob like you?"
"Heather, you and I know if you don't pass your classes, you lose everything. Now why don't you think rationally and go along with the plan?"
(Heather's eyes start to well up with tears because Lenny is absolutely right. She's worked so hard and has no one else to help her. What can she do if she doesn't pass these courses. Reluctantly she asks,)
"Lenny what exactly do you have in mind?"
"Let me have my way with you for the night, I just want to know what it's like to be with such a beautiful babe like yourself. I've been so frustrated for so long. I see you girls everyday. I know all these good looking dude are the ones who get to sleep with you and I'm left alone with just my imagination."
(Heather weighs her options and reluctantly agrees to the option. She's disgusted over the circumstances but knows its her only option. It's just one night and it's not like she hasn't slept with someone she's regretted before. What college girl hasn't gotten so drunk and woke up the next morning with a tool next to her. She watches as Lenny clumsily grabs her by the shoulders and pushes her down to the bed. He kicks the books to the floor as he starts unbuttoning his pants. Heather doesn't know what to do or how to feel and grimaces as he starts kissing her neck. She knows he has never had sex by the way he kisses her. He probably has never even kissed a girl before. Heather looks down toward his belly and sees his erect dick come out of his pants. Its not small but not large either. It's actually kind of thick but bent funny. Heather is bummed because she hoped it was small and thin so she wouldn't have to feel it much. Lenny pulls Heathers tiny jean shorts off and realizes she is wearing a red lace thong panty. He gets a huge grin on his face as he pulls them to the side. He doesn't even take his shirt off as he tries to find her vagina with his dick.)
"Wrong hole jerk!" (Heather grabs his cock and directs it to her pussy. The feeling of her hand around his dick causes it to grow immensely. It's always been his hand but now its an actually girls. Her hand is so feminine and smooth. Her nails make it look so sexy too. He thrusts into her and screams out in elation. "Oh shit, this is what it feels like. Its so hot inside. I've dreamed of this for so long!"
(Heather is shocked by his statement and doesn't know what to say as he starts thrusting in her. Her head starts hitting the bed's head board as he starts to pound her harder and harder.)
"Your tits are so perfect and round. Your nipples are hard too!" (They aren't hard because Heather's turned on, its only because its freezing in his room. She realizes Lenny lied about it being warm just so she would wear something tiny and revealing for him.)
(Lenny fucks her for a couple minutes, moaning out loud as he drives his cock in and out of her. Within minutes he finally cums all over her stomach.)
"Okay you fucking sicko, change my grades now so I can get the heck out of here!"
(Heather pulls her panties back over and lifts her shorts back up to her waist. As she puts her tank top back on she watches Lenny stagger over to his computer desk. She's perplexed because the grade books were on the ground near his bed. Maybe he's just getting a pencil with an eraser so he can change the grade. He grabs hold of his computer mouse and flicks it until the computer screen turns on. Heather is startled to see a live video camera shot of her still on the bed.)
"What the hell is going on? You fucking taped this you asshole? I'm going to smash that computer you sick jerk!"
"It's not going to help Heather. I've already directed the live feed to an outside server. It's stored there safely away from anyone. All I have to do is send a link to your coach and any other soccer scouts and your soccer dreams are over."
"What? Why would you do that Lenny." (Heather is shocked. It's not just a recording he wanted to masturbate to. Its like he wanted to blackmail her.)
"I recorded it because now I have you in a very awkward predicament. You see I'm going to change your grades still so you can pass your courses. A promise is a promise. The thing is now you have to do what I want when I want or else I'll leek this video out. Now when I want to fuck such a perfect chick like yourself all I have to do is call you and have you meet me here. I can even come to your place and fuck you there if you want. You're not going to do anything about it because you know I can totally ruin you with this tape."
"Lenny you jerk. You're such a jerk. Unfortunately you're right though, my soccer career is everything to me so please don't ruin it. You're definitely going to pay for this one day though, I'm going to get you for this. You're such a spineless weasel. You and your fucking glasses, fat belly and pale skin. (Heather laughs) "You call what you did to me fucking? Yeah right!"
(Lenny runs back over to the bed and pins her arms down as he lays on top of her naked. He flips her over so she's face down and pulls her shorts off as he rips her lace panties off of her. She screams for a second but realizes it's hopeless, no one can hear her. She can't say anything anyway because he'll send the video out. Lenny pulls her halfway off the bed and takes her top off. There she is completely naked on the bed with a total geek who is going to fulfill all of his wild fantasies with her. As her ass is hanging off the bed, Lenny grabs his erect cock and shoves it into her pussy. Heather realizes he's a quick learner because he had no trouble finding it now.)
"I'll show you what fucking is babe. I'm going to fuck you in every position tonight. You're going to be the sorest bitch in the morning. You girls used to make fun of me in school, calling me a geek. Now look at me, I have my dick in you and you're my bitch. How about I call one of my computer geek friends and let him fuck your brains out too?"
(Lenny grabs hold of her hips and bones the shit out of her. The bed starts shifting as he starts taking full thrusts into her. He reaches around and takes hold of one of her tits as he lifts her up against his chest.)
"I've always wanted to fuck a chick doggystyle. This is even better than I imagined. I think I like this position better than the last." (Lenny starts moaning loudly almost like an animal.)
"Ow Lenny, you're going to hard, it's hurting me."
(Every time he slides into her with his cock, Heather lets out a gasp of air. She is disgusted as she watches the video monitor which is facing right at her now. She can see Lenny's face as he fucks her like a machine. Eventually he cums inside her and tells her she can go for the night. Heather is humiliated but has no idea how to handle the circumstances. She knows she can't tell anyone and she knows Lenny now has two videos of them fucking. She gets home and falls asleep instantly.)
The next day Lenny is in class and Heather comes walking in wearing sweat pants and a sweat shirt. Lenny just chuckles because he knows she wore that to prevent him from leering at her. He doesn't care though because her ass looks great in the sweats and he can still stare at her beautiful face. Heather decides to go to the library that night and study for her other courses. She's not about to let some other asshole take advantage of her situation. It's gets late and all the other students have already left for the night. The only company Heather has is an old woman who is the librarian. She is oblivious to the fact that Heather is sitting just in front of her because she is so hard of hearing and her eyes are weak. An hour passes and Heather decides to leave for home. She has her cell phone and see's that Lenny has sent her a text message to come over. She's furious over it and chooses not to respond. As she walks to the back of the library and down an aisle to put away a library book she suddenly gets shoved up against the shelf.
"What the heck!"
(As she looks to see what pushed her, she notices Lenny there. He pulls her sweatpants down as he flips her around. As her sweats hit the floor he lifts he up and sticks his dick right in her pussy. Its so swift and sudden that Heather barely realizes what is happening.)
"Shut your mouth Heather, you know our agreement. If you don't respond to my texts you're only going to get it rougher."
(Heather realizes the severity of their agreement and decides to say nothing at all. Lenny continues to fuck her as he holds her in his arms. After several minutes he puts her down and lifts her left leg over his shoulder and fucks her standing up.)
"Wow baby your fucking flexible, I love it." (Again Heather is disgusted by Lenny and all his sweat and fat.)
He eventually cums inside of her and jolts uncontrollably. He pushes Heather off of him and against the shelf as he puts his zipper back up.
"Okay baby, you're coming home with me. I have some more things I want you to do. You're going to give me the best blowjob you've ever given."
"You're such an asshole Lenny, how can you live with yourself."
(Heather wipes the tears from her face and lifts her sweats back up. As they walk to the parking lot, a teammate of Heather's sees the two of them and asks where they are going. Heather responds,) "Lenny is going to tutor me tonight at his place. The teammate is surprised because she would never guess Heather would want to be caught alone in one place with Lenny. I mean what girl, especially a hot girl would. As soon as they drive up, Heather walks upstairs to Lenny's place. As he closes and locks the door, She suddenly sees several outfits hanging up on the curtains. One's a cheerleaders uniform, another one is a string bikini. The third one is Heather's soccer uniform. He rips her sweats off and shoves the cheerleader uniform in her face. She puts it on and notices its a bit tight and kind of small.)
"Now what Lenny? What sick desire are you going to fill tonight?"
"Ha ha, I want to see just how flexible you are."
(He walks her down to his living room and picks her up in his arms. He sits her on the sofa and spreads her legs wide open. Lenny pulls her panties to the side and starts eating her out. Heather realizes no one has ever done that to her before and discovers it feels amazing. She closes her mouth in an effort to hide her gasps of pleasure. She gets really wet and her pussy starts to swell up. Lenny notices how red and pink her vagina's lips are getting and can't hold it back anymore. He grabs the inside of her ankles and pushes them each against the couch cushions as he shoves his dick into her. She lets out a tiny shriek which Lenny realizes was in pleasure.)
"You're going to grow to love getting fucked by a geek like me."
(Heather looks over her shoulder back towards the other two outfits as Lenny catches what she is looking at."
"Baby, I've got a lot more in store for us tonight."