Hughes Academy was a bright school for bright students, but after the initial shock of the tougher classes of the first year in comparison to middle school, the second semester was a breeze by comparison. Things seemed easier, and the same could be said for romantic connections. Despite being generally for richer kids, Hughes Academy was no different than other high schools, festering with teenage hormones and students either seeking either something long-term, or at least a simple release of said hormones via one-time hookup. At least this applied for most students, except for sixteen-year-old Jimmy Caufield, who found himself feeling quite lonely in his second year.

Jimmy was better at making friends with people older than he was as opposed to those of his own age. He generally hung out with his stepsister, Alicia, and her friends. Except now that Alicia was with her crush, Jack, they were practically inseparable. Another one of her friends, Tony, finally admitted his feelings about another person in their core group of friends, Hilary, even though the two often argued in front of everyone else, they could just as often be seen sitting on a bench just staring deep into each other's eyes. As more and more people around him started to find happiness with others that they had long friendships with, Jimmy started to feel left behind. Not wanting to butt into everyone else’s relationships, Jimmy chose to keep his distance and respect their couples’ time together.

It wasn’t all bad though; this year Jimmy had gotten his dorm room all to himself and was told that due to low enrollment, he would be one of the students randomly selected to have their own room to themselves. He also saved up some money from a couple of odd jobs he had done here and there, primarily bankrupting the older rich kids at the academy by way of his skills at Texas Hold ‘Em. He bought himself a fancy new dual-screen desktop setup and paid a small amount to one of the recent grads for a desk he was trying to get rid of before moving away. Now Jimmy would spend hours of his free time playing video games on his computer.

Recently though, the feeling of loneliness that continued to creep its way into his mind started to overshadow the fun he was having playing games all night. As a result, Jimmy had started to watch various forms of pornography in the evenings. It started simple, just basic videos with a guy and a girl, but after a while he had begun exploring role-playing vids, like step-family stuff. Most recently, he had gotten into casting couch-style videos. Not only did the sex itself excite him, but Jimmy was also turned on by the very idea of people getting paid to have sex on camera for the first time when they knew thousands of people might be seeing them do it on the Internet.

Tonight was no different than most nights. The younger Caufield sibling found himself yet again sitting at his desk, staring at his computer. He wore a loose white t-shirt and grey sweatpants pulled down enough to expose his six-inch stiff cock, just waiting to be played with. Certain videos just didn't do it for him anymore; he wanted to be able to slightly relate to what he was watching so that he could see himself in the video. He liked ones that didn't just jump into the sex, as he enjoyed watching the scene get set up, the foreplay, seeing the couple take each other's clothes off, stuff like that.

Jimmy started slowly pumping himself while watching a clip from a video about a stepbrother and stepsister have sex while their parents were in the next room arguing, but he had grown tired of the multiple ‘step siblings have sex while other people are nearby’ style scenes. Switching channels on the porn site he was exploring and scrolling down the amateur's section, his eyes caught the thumbnail of a video called “Carmen is Ready to Party!” The girl looked familiar to him so he decided to check out the video. What Jimmy saw next shocked him so much that his heart started to beat at a speed it never had before.

The video was shot in a plain white room, with a black couch in the middle of it, your basic casting couch setup. The young, long black-haired Latina girl that walked into frame and sat on the couch just so happened to be eighteen-year-old Lupe, one of his sister Alicia's best friends, and the only one he knew of that wasn’t in a committed relationship like the rest of her friends.

Jimmy blinked and rubbed his eyes a few times to make sure he was seeing things clearly, but it was her alright: Lupe, the uber-optimistic and sexy aspiring actress, was in a porn video. Called Carmen by someone behind the camera, Lupe was wearing a tight blue tank top that showed off her mid-section, and the dangling bellybutton piercing that she always wore with a butterfly on the end of it, along with a pair of short jean shorts and a pair of cork-wedge sandals with black straps. She looked sexy as always, and still had the same gleaming smile on her face that she had when she was hanging out on campus, even though she was now on a casting couch, about to be fucked by a complete stranger.

“So, who are you, Carmen? Tell us a bit about yourself?”

“Well, as you said, my name is Carmen, I’m trying to breakout into acting, so I’m taking classes at the University of California – Pacifica.”

“Well, you certainly have the looks to be a great actress. And how old are you?”

“I turned eighteen about two months ago.”

“So, you’re still new to being an adult, I see.”

“Yeah, but I'm still a teenager at heart,” Lupe laughed.

“There she is!"” The man commented. “You are truly a magnificent sight! I bet when you’re in a room all of the guys,’ and some of the girls’ eyes all end up getting stuck on you.”

Lupe, or Carmen as she was now being called, twirled a strand of her long, jet-black hair in one of her fingers before replying, “Well, I do try to stand out in a crowd. I like to show off a little, but I don't want people to think that I’m too slutty.”

“Oh, I think you are exactly the right amount of slutty, Carmen.” The guy clapped his hands once. “So, are you nervous at all?”

Lupe smiled. “Not really. I've never done this before, but I like sex, and I like being on camera, so this just seems to be the perfect mix for me.”

“I'm glad you feel that way, Carmen, really glad. So, can we see a little bit more of you?”

Without responding or showing even a shred of nervousness, Lupe stood up, grabbed the hem of her tank top and lifted it up and over her head, exposing a black bra underneath with diamond sequins on it, and tossed it on the floor by the couch. Next, she unbuttoned her jean shorts before slowly inching them down her tanned legs until they reached her ankles and she stepped out of them. She was wearing a black thong that also had diamond sequins on it, and hugged her curves perfectly.

“Oh, yeah, that’s what we want to see. Look at that amazing body!”

“I try to take good care of myself,” Lupe replied with a bright smile.

Jimmy didn’t even realize that he had begun to jerk off, he was so turned on by seeing one of his sister’s friends about to get fucked on camera! He always had a bit of a crush on all of the girls in his stepsister’s group of friends, but he did always have a special interest in the gorgeous brown-skinned Puerto Rican girl that was Lupe.

A naked white guy with a seriously muscled physique walked into frame.

“Well, would you be willing to share that nice body of yours with us and Mike here?”

Lupe smiled and wrapped her arms around Mike’s neck before saying, “It would be my pleasure.” She started kissing Mike, her tongue visibly wrestling with his. Jimmy was running out of breath as the muscles in his chest tensed up so much to the point of being mildly in pain. He watched as ‘Mike,’ slowly pulled the black straps of Lupe's bra down her arms, revealing a pair of small, possible B-cup, but perfectly perky breasts. The guy began to massage Lupe’s breasts as she moaned into his mouth.

The scene continued to play out, but Jimmy wasn’t able to watch much more. It’ wasn’t because he couldn’t stand watching Lupe have sex with some random stranger, oh no, it was because just the sight of seeing her start to blow Mike was enough to make himself blow his load before the real sex started. Cum was splattered all over Jimmy’s cock, hand, pants, some even landed on his desk, including his expensive new gamer’s keyboard.

The force of the blast was so intense, it took several seconds for Jimmy to come out of his post-nut high to realize the massive mess that he had created. The lack of inspiring material he had been viewing the past couple of days had left him going dry several nights, so the feeling of finally finding something to get him off, not to mention the massive boost provided by the fact that is was one of his sister’s friends in the video, it was no surprise that he produced such a massive load.

Jimmy cleaned off himself and his desk as best as he could before sitting back in his chair and finally starting to relax. He looked up at the ceiling and slowly got his breathing back to normal.

“Whoa,” Jimmy said out loud. “That, that was, she was, amazing!”

XXX

The next day did not start well for Jimmy. Not only could he not sleep after what he had just watched, but he forgot to download Lupe's video. He desperately needed to see the video again so that he could watch it to the point where she actually got fucked. He kept typing the title of the video on the site he was exploring the previous night, but it seemed that the video had been taken down, and the actress known as “Carmen,” apparently was not famous enough to have her own section on any of the porn sites that he regularly visited. He couldn’t even find the legit site that hosted the video in order to pay to watch it.

The situation was not good. Jimmy knew that after seeing the video with Lupe, there was no other type of porn that could excite him the way she did. Jimmy was getting desperate. If he couldn’t see any more videos of Lupe himself, he would ultimately be driven to asking her about the video himself, something that would surely get him slapped, not just by Lupe, but by his sister as well. If things went badly, Jimmy could be cut off from ever hanging out with Lupe or any of the friends in his sister’s orbit.

As Jimmy got dressed and ready for class, he thought of a few ideas that he could try with Lupe after class.

XXX

A few minutes after the final bell rang for the day, Jimmy found Lupe and the two engaged in some of their usual conversation topics, such as how they were doing, was anything going on, did they have any plans for the weekend, shit like that. Jimmy had to try his best not to blush in front of Lupe, or even worse, stare down at her tits in the white spaghetti strap tank top she was wearing that was see-through enough to show off the red bra underneath it.

The convo wrapped up quickly, but his hormones got the better of him and made him act irrationally. As a result, Jimmy stalked Lupe around the campus as she spoke to other people on the way back to her dorm. After running into a particular group of friends, they decided to go swimming. This would be Jimmy's chance to get at least a semi-nude view of Lupe in a bikini that he could use while he masturbated that evening. All of a sudden a better, but potentially dangerous idea, entered his perverted brain.

Once upon a time, he and a group of other teens his age had found a way to spy on the girls’ change room at the school’s outdoor pool. Perverted thoughts of Lupe in mind, Jimmy raced his way to the girl’s change room, which was its own small building next to the pool, while the guys’ change room was in a separate building on the other side of the pool. Someone had left a ladder in some bushes next to the girls’ change room, which could be used to spy on the girls by getting people onto the roof to look down through a series of skylights into the room below. Several teens had gotten caught peeping on the girls, but somehow the ladder kept finding itself back behind the same set of bushes, ready for the next horny teen to use.

Jimmy set up the ladder and did his best to adjust the trees and bushes near the ladder to hide it and himself as much as possible from any passersby. He climbed the ladder and then slithered over to one of the skylights. The outside glass hadn’t been cleaned for a while, so he used his sleeve to wipe a small hole into the dirty glass so that he could see in. As a bonus, the dirt on the rest of the skylight would help to camouflage him from being seen by the girls below, since only a small hole would be visible.

Looking at all the hot girls from his age of sixteen to Lupe’s eighteen, of various ethnicity and breast size, caused Jimmy to pitch a small tent in his pants, awkwardly making him shift to his side from his stomach as his erection became squeezed between him and the roof. After a few seconds, he saw Lupe walk into the change room. He watched as her ass poked out as she pulled her jeans off. Her tanned figure was so intoxicating that it caused the rest of the female bodies around her to disappear from his vision.

“You wanted to be an actress,” Jimmy whispered to himself. “Well, honey, you’re taking center stage for me already!”

Come on, turn around! Jimmy thought to himself. Let me see the front of you. Jimmy finally got what he wanted, as after changing into her pink bikini, Lupe just so happened to look up towards the skylights. Jimmy could immediately feel heat rushing through his body as his heart fluttered uncomfortably. He could swear her eyes met his as she narrowed her eyes in his direction. Jimmy rolled over quickly, nearly falling off of the roof of the small building before he started to climb down the ladder.

Before even making it all the way down the ladder, someone threw a rock into the trees that shielded Jimmy and the ladder he was currently stuck on. Not wanting to make any noise, he froze where he was, hoping that no one could see or hear him. A second rock was thrown into the trees, this one hitting Jimmy in his left shoulder, causing him to bite his tongue to prevent him from giving himself away. Unable to resist the pain, though, he slipped off the ladder and fell about two meters down to the ground.

“What are you doing?” A girl’s voice asked.

“Sorry,” he heard Lupe say. “I thought I saw a raccoon or a skunk so I wanted to scare it away.”

“Eeewww!” another girl said. “Let’s get out of here!”

“Come on guys, let's go grab some food from Roxy’s Diner,” he heard Lupe say.

Once they seemed to be far away enough, Jimmy hissed out loud from the pain he was in. In addition to getting hit in the shoulder with a rock, he seemed to have twisted his right ankle in the fall. He went over to the ladder and returned it to its previous hiding spot, a courtesy for the next Peeping Tom that wanted to risk a shot at seeing the girls of Hughes Academy au naturel. Peeking from the bushes to make sure no one could see him leave, Jimmy hobbled out and started limping his way back to his dorm.

Despite the pain he was in, his cock remained semi-erect, thinking about the nude body of Lupe, and a few other choice girls in the change room, which he would definitely be using when he got back to his dorm room.

XXX

After making it back to his dorm, Jimmy took off his shirt and changed into a pair of Hughes gym shorts. He lay on his bed, holding an ice pack on his swollen ankle as a second one rested on his shoulder where Lupe had nailed him with the second rock. Despite her not yelling his name as she threw the rocks into the trees by the girls’ change room, Jimmy knew Lupe saw him watching her. It was just a matter of time until she either confronted him, told his sister, or worse, the school! Jimmy closed his eyes and scrunched his face in both fear for what was coming and anger at himself for the despicable act he had just committed.

Suddenly there was a knock at his door, causing him to jump a little at the unexpected noise. Who could that possibly be at this time of night? Then he thought about it and his heart sank into his stomach. She didn’t even want to wait till morning to do something; Lupe’s doing something right now!

In a creaky voice, Jimmy called out, “It's open.” He had left the door unlocked since he couldn't get up to open the door if someone did come, as unlikely as it was. The door opened and in walked an unhappy-looking, tanned skin, long black-haired Latina girl wearing a white, spaghetti strap tank top, see-through enough that you could see the red bra that she was wearing underneath it. It was Lupe. She closed and locked the door before turning to him and crossing her arms. Jimmy knew he was screwed.

“You have some balls, peeping on all of us, you little perv!” Lupe said sharply.

“Well, actually, it was just you I wanted to look at.” Why the Hell did I just say that? Jimmy questioned himself. He should have said that it wasn’t him, or anything other than what he had just said, but deep down, maybe he wanted to get caught by Lupe. Perhaps he wanted to let her know how attractive he found her. Either way, what he said was not working in his favor in either respect.

“NOT. WHAT. I. MEANT!” Lupe said in a louder voice as she emphasized every word that she said.

“Sorry, sorry!” Jimmy replied while raising and lowering his hands to signal for her to keep her voice down. “I really am sorry, Lupe. I just got carried away with my feelings for you, and as a result, I did something stupid.”

It appeared that Lupe was puzzled by what he meant with regards to his feelings for her. She walked over to his bed and set down next to him. “How’s the leg?”

“Well, I have to limp to get around, but I can still walk and do things myself, like wipe my own ass.”

Lupe giggled gently. “Sorry, I didn’t know I was going to deliver such a crippling blow to your leg with that rock.”

This time it was Jimmy who gently laughed. “Actually, the rock you threw hit me in the shoulder, hence this ice-pack,” he said as he tapped the one on his shoulder. “The ankle was due to the fall from the ladder. Anyways, I had this coming, didn’t I?”

“Yes, you kind of did, but still, I’m sorry too,” Lupe responded before a questioning look crossed her face. “You said that you have feelings for me. Where did these sudden feelings for me, which caused you to peep on a room full of teenage girls, come from?”

“I, I uh, I-” Jimmy just sighed and decided to tell the truth. “I saw a video of you, online, except-” He paused before finishing. “You called yourself Carmen.”

“Oh, shit!” Lupe blushed before quickly getting upset again. “You shouldn't have watched that once you recognized that it was me. I’m one of your sister’s friends, Hell, I’m one of your friends. Why did you keep watching it?”

Jimmy shrugged. “Because you’re so hot. I’ve had a crush on you for a while, and the video awakened something in me.” Jimmy paused before asking a question of his own. “Why did you even make a video like that? I know that you really want to be an actress, but I never would have thought of you as that kind of an actress.”

“I’m not, and I don't,” Lupe responded in a slightly hurt voice. “I needed money. My scholarship only covers so much to go to this school, and I didn’t want to leave, especially in my senior year. The video paid enough for me to keep going here, so I did it. I never thought anyone here would know about it. I figured since I only did that one video that it would just get buried beneath all of the rest of the mountains of porn on the Internet.”

“I promise, I won't tell anyone, Lupe,” Jimmy said sincerely.

“Oh, I know you won't, Jimmy.” Lupe stared daggers at him. “’Cause I'll beat you far worse than what happened to you today, if you do.” She gave him a small nudge on his shoulder that caused him to hiss at the slight pain it caused.

Jimmy put his hands up. “I swear, not even a single friend will know about it. I wouldn’t do that to you. I really like you, Lupe.”

The room fell silent for a moment. “At least let me say this,” Jimmy started. “Seeing you in that video, it helped me see just how amazing you really are.” Lupe scrunched her face. “I mean, you already looked beautiful before I saw you naked!” Jimmy scrambled. “But now, I can tell that there isn’t a single part of you that isn’t perfect, mind or body.”

Lupe looked like she was thinking about what he had said, and eventually, Thankfully, Jimmy thought to himself, she finally smiled.

“Thanks, Jimmy.”

“I’ve never felt the way about any girl as I do about you after I saw that video. You see, I forgot to save the video, and when I went to the website the next day, the video was gone and I couldn’t find it anywhere. I needed to see you naked again. I felt like I was going to go crazy if I didn’t. Call it a case of foolish teenage lust, but no matter the reason, it wasn’t cool what I did, and I’m really sorry.”

“No, it wasn’t cool,” Lupe responded sharply before quickly letting a shy smile creep onto her lips. “But I'm really flattered, like a lot. I was afraid that I was going to look stupid. I actually don’t really have sex all that often, as the video might make a person think.” She giggled. “I was just acting.”

“Well, you did very well. Not just the sex, or looking amazing, but I really could buy that you were like the Carmen in the video. You’re a really good actress, Lupe.”

Again, nothing but awkward silence, until Lupe did something that Jimmy never would have expected to happen, ever. She placed a hand on Jimmy's cock and started to gently rub it through his shorts. Jimmy was in such shock that he couldn’t even choke out a ‘Lupe, what are you doing?’

“So,” Lupe said, snapping Jimmy back to reality. “You must have really, really enjoyed that video, hmm?”

“I, yeah, yes, I did,” Jimmy said as his breathing started to grow heavier and heavier and his heart pounded faster and faster.

“Well, I think it’s only fair that for everything you saw,” Lupe started using a single finger to trace Jimmy's growing erection through his shorts. “That I get to see something of yours, too.”

“Really?” Jimmy asked in both an excited and nervous voice.

“Yeah, like right now,” Lupe demanded.

Jimmy did as he was told and pushed his shorts down to his knees. Jimmy's cock sprung out of his shorts as soon as it was freed of the waistband, staring directly up at the ceiling. Lupe grabbed the stiff cock and looked at it as she held it in her hand before starting to slowly stroke it up and down.

“Let's see just how much of an effect I have on you exactly,” she smiled.

Jimmy breathed faster as he started to feel overwhelmed by the pleasure that Lupe's soft hand was having on his cock. She practically massaged the skin of his shaft through her fingers as she jerked him. His body had finally started to relax and he just laid there, watching the sexy eighteen-year-old play with his cock. Jimmy’s muscles tensed and his dick throbbed with anticipation of the release to come. His asshole clenched itself shut as Lupe turned her head so that her eyes met Jimmy's. She bit her lower lip, her perfect white teeth slightly visible behind her soft lips.

“Am I getting you off, Jimmy?” Lupe asked in an almost sinister voice.

“Ye-yeah.” Jimmy groaned. “But it would help if you,” He nervously asked, “Kissed it.”

Lupe laughed softly. “Kissed it, seriously, Jimmy?”

“Just a little one, please?” Jimmy begged.

Lupe adjusted herself on the bed and leaned down towards Jimmy’s lap as she shifted her long hair off to one side and out of the way. Her face relaxed as her lips approached Jimmy's cock. Lupe planted a soft kiss on the tip of his cock, followed by one a little longer than the first.

“Yeah, just like that,” Jimmy said as his right hand found itself on top of Lupe's head. “Just a little-”

With a gentle push, he slid himself into her mouth. Rather than freak out, Lupe just went with it and started to slowly move her head up and down his cock as she gently jerked the base of his shaft. Jimmy gasped as Lupe’s tongue grazed the sensitive tip of his cock as she continued to slowly bob her head up and down. The suction took Jimmy by surprise, causing him to tense up repeatedly before relaxing as Lupe’s head rose to the top of his dick, only to rinse and repeat.

Jimmy's cock may have been smaller compared to the men Lupe had had sex with in the past, but it was still hard, smooth, and just the thought of blowing her best friend’s younger brother, excited her more than sex with a well-hung stranger ever would. She started to bob a little faster and she would also move her head around, causing Jimmy’s cock to get pulled in several different directions, introducing new sensations to his cock.

Jimmy breathed heavily, getting even more turned on when Lupe started making soft little moans with her mouth still wrapped around his dick. Feeling like he was on a winning streak, he reached over with his left hand and gently began to squeeze Lupe's right breast. It was covered by her top and bra, sure, but the feeling of a girl’s breast in his hand, clothed or not, felt good to Jimmy, and Lupe didn’t object.

Lupe smiled as she sucked harder on Jimmy’s cock, tickling the skin on his balls with her fingers. She forced herself down harder this time, her nose reaching his stomach and his tip hitting the back of her throat, but her gag resistance held up. Jimmy could feel the cool air of the air-conditioned room on his wet shaft whenever Lupe's head rose up, causing him to shiver whenever it happened. The shivering was intense enough that Lupe could feel his cock vibrate as it filled her mouth.

A surge of tension started to flow through Jimmy as the muscles in his cock tried to fight back against an inevitable orgasm. Jimmy tried to gently push Lupe’s head off of his cock and he panted her name while trying to warn her what was about to happen, but she kept her head stuck in place and pushed his hand away. Not able to hold back any longer and with a number of loud grunts, Jimmy sent several large blasts of cum into Lupe’s mouth. As he was finishing, Lupe took it all in graciously, swallowing everything, as to hide any evidence of what had transpired that night.

Lupe wiped her mouth and grinned at the recovering Jimmy. She kissed him on his forehead before getting up and walking towards the door.

“Wait, don't go yet!” Jimmy pleaded.

Lupe giggled. “You're sweet, Jimmy, but I need to leave.” She winked at him and walked out. Jimmy wanted to get up and say something, anything, to Lupe to get her to stay, but his ankle stopped him, leaving him to lie down and replay in his head what had just happened.

XXX

As Lupe sneaked out of the boys’ dorm, her mind was filled with shock as she berated herself for what she had just done; she had performed oral sex on her best friend’s little brother. Jimmy was sixteen, sure, but how could she have betrayed her best friend’s trust like that? In reality, though, she actually really enjoyed what she had just done when she thought about it. Her best friend’s little brother, it was like something out of a porn video. But it won’t happen again. She stopped to think for a second. Could it?

Lupe’s thoughts were interrupted when a blonde girl walking down the hall towards her caught her attention.

“Oh! Hey, Alicia,” Lupe gulped.

“Hey to you, Lupe,” Alicia laughed. “So where have you been? I was starting to get worried. You said you just had to take care of something quick, but you were gone for almost an hour.”

“I'm sorry, Ali,” Lupe started. “But it's all good, I took care of what needed to be taken care of. Let's get back to our dorm before one of the monitors write us up.”

The girls headed back towards their rooms, but Alicia prodded Lupe. “So, was he any good?”

“A girl doesn't kiss and tell,” Lupe slyly replied.

Alicia smiled. “He must have been really good. If he was terrible, you would have told me.”

“Alright, alright, you got me,” Lupe said nonchalantly.

“So, who was it?” Alicia asked.

“Like I said, I don't kiss and tell,” Lupe responded in an increasingly annoyed tone.

“Okay, sorry,” Alicia replied disappointingly. “At least tell me, do I know him at all?”

Lupe giggled. “Oh, you know him, alright!”