The sensation of Lupe’s fingers stroking his cock, squeezing its skin and causing his muscles to tense up played on his mind. It was amazing. Blowjobs had always felt good to Jimmy, but having Lupe give it to him was something else.
A few days had passed since Lupe had blown sixteen-year-old Jimmy's mind, and his cock. A memory like that would forever be ingrained in Jimmy’s memory. Not only was the experience of several nights ago absolutely amazing, Jimmy was just glad Lupe didn't hate him and report him to the school for peeping on her in the girls’ change room. The two hadn't seen each other since that night a few days ago, and Jimmy had honestly been avoiding Lupe if she ever approached him. If he were hanging out with his stepsister or any of Lupe’s other friends, he would immediately excuse himself and walk away.
One day, Jimmy was sitting alone at a lunch table outside, thinking about what he should do next. He had no idea how to act around her after what had transpired between the both of them. Lupe dominated his thoughts, and no girl his age had come even close to affecting him the way she did. Lupe was older than him, more experienced, so sexy, it was a series of turn ons that no other girl in his grade could give him.
The problem was that there were so many questions left unanswered. Was what happened just a one time thing? If it was, he’d hate it, but he could live with it, but what if she wanted something else to happen? If so, should he approach her? Should he wait for her to approach him first? All the questions gave Jimmy a massive headache.
It was due to these thoughts and questions that Jimmy had received C’s instead of his usual A’s on his past two tests. Jimmy was at such a prestigious school, with good extra curriculars, great friends, but the only thing he really cared about was what was going to happen next between him and Lupe. Porn was useless to him now. He had gotten a taste of the real thing with Lupe, and not only would anything but real sex suffice, he also only wanted to do it with Lupe.
Lupe was just so…
“Hey.”
A feminine voice interrupted Jimmy's deep thinking and he turned to face the girl that had spoken. Jimmy’s eyes widened at the realization of who it was: Lupe, or Carmen as she was called in the video.
“You seem pretty deep in thought,” Lupe quipped at him.
“I, yeah. There’s been a lot for me to think about the past couple of days.”
Lupe pulled out a chair on the opposite side of the table from Jimmy and crossed her legs. Jimmy couldn’t help but look and see if he could peer up her short, white, pleated tennis skirt as she crossed her legs, but no dice.
“So,” Lupe began. “Look, Jimmy, what you said to me, about how much you like me and how beautiful you think I am, it was really sweet. If we were the same age, then maybe I could find it in me to pursue a relationship with you, but I’m two years older than you, and you're my best friend's younger brother. I can’t do this to Alicia.” Lupe sucked in a big breath. “So, I just want us to be friends, good friends, okay?”
Jimmy was disappointed, no doubt, but still, he understood where she was coming from. “Yeah, I understand what you mean. That would probably be best.” His tone indicated that he was disappointed but agreed with Lupe. On the inside though, he was practically screaming that ‘friends’ wasn’t enough for him. He needed her in a way that friends did not act around each other.
Lupe patted one of his hands that rested on the table just as the bell rang and she excused herself so that she could go to her next class. Jimmy just sat for a while, regretting having not argued why they should pursue a relationship that was more than just as friends. He started to feel like he was giving up on something that he needed in order to keep on living. Lupe’s words about his age stung him particularly, as he wished he had fought back and told Lupe that they were only two years apart and both teenagers, that there was nothing illegal about what they had done, and most importantly, they clearly enjoyed what had taken place between them, so why stop? If only he had said...
XXX
The following day Jimmy went to his morning classes as usual, but he didn't have any in the afternoon, as he scheduled everything earlier in the day so he was free to enjoy the afternoons as he saw fit. He decided to visit some friends in the girls’ dorm for a change. He was wearing a blue Hawaiian-shirt with rolled up sleeves over a white t-shirt and jeans. One of his friends, Jenna, complimented him on how he looked, causing Stacey to giggle at her friend’s attempt to flirt with him.
While he may have gotten along better with the older teens on campus, Jimmy was still able to have a good time with anyone that was at least roughly his age. As they were talking about what new movies were coming out soon, he noticed that he was carefully studying his female friends. They were all nice, and cute, certainly nothing to scoff at, but they just didn't make him feel the way Lupe did. While they made him feel relaxed, Lupe made him feel nervous, a nervousness that made him want to act dangerously and do whatever it took to get physical with her.
After a few more minutes, Jimmy excused himself and decided to take a walk. It was raining, so he just found himself walking around the dull white halls of the dorm buildings since the student centre had just closed for the day. Without realizing he was doing it, he walked up to the second floor of the girls dorm, which just so happened to be the floor his stepsister, Alicia, and more importantly, Lupe’s, room was. As he emerged from the stairwell, Jimmy just so happened to run into the one person he couldn’t stop thinking about.
“Oh, h-hey, Lupe,” he stammered as he gave a weak smile.
“Hey, Jimmy,” Lupe smiled back completely natural, as if none of the past few days had occurred between them. Lupe was wearing a tight purple athletic tank top under an open jean jacket with short jean shorts and cork-wedge sandals, the exact same shorts and sandals that she had been wearing in the porn video he had seen her in that started all of this. If she had been wearing the same blue tank top, Jimmy just might have lost it and leapt at her right there in the hallway.
“What's going on?” Jimmy asked.
“Not much. I just dropped a math book off to Hilary that she let me borrow for a final,” Lupe replied as the two found themselves walking next to each other, towards her room.
“Cool,” Jimmy replied.
“I'm just headed back to my room now.” Lupe continued. “So, what’s up with you?”
“Nothing really. I hung out with some friends from here, but to tell you the truth, the girls my age are kind of annoying. They giggle at everything I say and never want to talk about anything serious,” Jimmy complained.
Lupe laughed. “Yeah, the 'giggle at everything a guy says,' it’s a classic. It might be a sign that they like you as more than a friend.”
“Well I don’t like them in that way.” Jimmy explained, “I like girls who know what they want and work to get it. Someone who is more mature, smart, someone who is experienced physically. A girl like-”
“Like me?” Lupe said as they stopped right at her door.
Jimmy turned to face her.
“I mean, kind of. I’m just saying that those are the qualities I like in a girl, you know? You just happen to have all of them.”
“Uh-huh.” Lupe bit her lower lip and crossed her arms. She looked Jimmy up and down and noticed a large bulge in his jeans. She moved a finger over towards Jimmy’s crotch and tapped the small mountain that was forming. “He like me too?”
Jimmy looked down and recoiled at what he saw. He didn’t even know that he was semi-erect. It must have happened as he was thinking of the qualities about what he likes in a girl, which included being knowledgeable physically, a trait he came up with as he thought back to Lupe in that video.
“Shit,” he said as he turned his body so that she couldn’t see it. I have got to work on my self control!
“You really do like me? Like a lot, don't you?” Lupe asked sarcastically.
Jimmy just stood there, unable to figure out what to say next. The answer was obviously yes, but how could he phrase it more eloquently? Before being able to think of an answer to her question, he felt Lupe’s hand take hold of his and gently pull him into her room before removing her sandals.
“Take off your shoes. Your sis hates when someone gets dirty water on her favorite rug.”
Once inside, Lupe locked the door and Jimmy took off his shoes as he was told.
“So, where is Alicia anyways?” Jimmy asked, referring to his stepsister that shared the room.
“Out for the evening with Jack, as always since they hooked up,” Lupe informed him as she proceeded to lower the shades on all of the room’s windows and turn on a few table lamps, but not the room’s main fluorescent light. The room had a dark, but semi-warm feeling due to the lamplight. The splashing of rain against the windows was the only thing interrupting the silence in the room.
Lupe walked over to her bed and sat on it as she motioned for him to join her with a single finger. Jimmy walked over and sat next to her, his heart racing. Was she going to take his hand and explain again why they should just be friends, or was something more intimate about to take place? She faced him and placed her hands on his shoulders and started to massage them. She could feel the nervous tension in his body start to drift away as Jimmy breathed deeply and slowly, closing his eyes, enjoying the feeling.
“Uh, Lupe?” Jimmy opened his eyes slowly and asked, “About what you said, about just being friends and not repeating what happened two days ago.”
Lupe sighed, as if in defeat. “Screw what I said. There hasn’t been a guy yet who looks at me and talks about me the way you do. This might be wrong, but as long as no one finds about about this, then that means nobody is getting hurt, so what’s the big deal? You keep this between us, and we’ll see where it goes from here,” the here being her removing his Hawaiian shirt and starting to lower herself in front of him.
Jimmy gulped as Lupe’s hands slithered down his chest, around his flat stomach, and along his thighs before resting them there and completing her descent to her knees. Lupe licked her lips as she viciously undid and tugged at his belt as she ripped it from his pants. Then, more gently, she undid and unzipped his jeans and pulled out his now fully erect cock.
“I guess he also really, really likes me,” Lupe commented with a devious smile.
She gently grabbed the base of his cock with her hand and licked its shaft from base to tip. After reaching the top, she slid her mouth over and down it, never removing her tongue from the tip until her mouth had swallowed it. It was deja vu for Jimmy as he began to fight to control his breathing as he once again experienced the feeling of Lupe’s warm, wet mouth cover his cock. As she swallowed and he felt her throat contract around the head of his cock for the first time, Jimmy was afraid that he wouldn’t last more than five seconds.
This time Lupe wasn’t interested in teasing and playing with Jimmy, she wanted to pleasure him as best as she could. She put her head and neck into it, using her right hand to jerk the small part of him that she couldn’t fit in her mouth with every bob of her head. Jimmy had to tightly grab onto the bed sheets in his fists in an effort to maintain at least some composure as he felt Lupe’s other hand gently massage his balls.
Taking a break so that she could catch her breath, Lupe asked in an innocent sounding whisper, “Do you like that, Jimmy?”
Jimmy nodded his head rapidly and hissed out a “Yes,” through his teeth. Lupe laughed lightly as she slid off her jacket before continuing to suck Jimmy’s engorged erection. Her moaning and slurping sounds got louder the faster and more passionately she sucked him, making him feel wanted by her as well, as opposed to him only desiring her.
Lupe popped Jimmy’s cock out of her mouth and declared, “I want more of your cock, Jimmy.”
She shifted from a kneeling position to a sitting one and then spun around so that she could lean her back against the bed. Lupe tilted her head back and motioned for Jimmy to put his dick back into her mouth. Jimmy had seen this in the porn he had previously watched and knew that it was so he could throat fuck her and shove his entire shaft past her mouth. He leaned on his hands and began thrusting his up and down, slowly at first, but gradually picking up the pace. Lupe looked so hot as she struggled to fit all of him inside of her as he fucked her throat, causing her to make loud gagging sounds each time his cock bottomed out in her throat.
Looking further down, he saw that one of Lupe’s hands was in her shorts. Her thighs squirmed around her fingers as she furiously rubbed herself. She wanted to experience some relief as well, so she used her new position to her advantage as it freed up her hands and left most of the work to Jimmy. The sight of Lupe playing with herself made Jimmy thrust even harder, feeling her throat clamp down on his cock as it didn’t know whether to swallow or gag to get rid of the blockage.
Jimmy said Lupe’s name a few times in a quiet, raspy voice as the pace of his breathing picked up. He felt his cock contract and then relax as he deposited four streams of cum into Lupe, her moaning indicating that she was enjoying the feeling of the warm liquid filling her up. The younger teen eased himself out of Lupe, who let out a cough as liquid filled the void where Jimmy’s cock had been. Still, she managed to swallow everything, not letting a single drop of liquid escape her mouth.
“I’m sorry if I surprised you,” Jimmy apologized. “I just got so carried away that I couldn’t stop thrusting.”
“It's ok,” Lupe said, more surprised about how aggressively he had throat fucked her; she liked his enthusiasm. “Just try to give me a bit of a heads up next time, okay?”
“I understand, I,” Jimmy paused. “Next time?”
Lupe smiled. “Like I said, as long as no one is getting hurt, we’ll see where this goes. Just no bragging to anyone about what we’re doing, okay?”
“Of course not!” Jimmy said eagerly. “I wouldn’t do anything to jeopardize having a relationship with you.”
His comment was innocent enough, but the part about them being in a relationship did make Lupe blush softly. On one hand, he was like a little puppy, a sixteen-year-old with a schoolboy crush on an older girl. On the other, Lupe found herself feeling like a princess at being worshipped by Jimmy, that she felt like the lucky one. Boys her age, or older, they told her she was hot and that she was good in bed, but none of them made her feel as good as Jimmy all around.
“So, how did I do?” Lupe asked.
“You were perfect,” Jimmy said wide-eyed. “I could never have even imagined a girl taking all of me inside of her like you did. It really was-” He looked down at Lupe, who wasn’t looking at his face anymore. “What’s the ma-”
Jimmy looked down and saw what Lupe was staring at. Apparently just talking about what had just happened had gotten the eager sixteen-year-old hard again.
Lupe gave a small giggle. “Well, seeing as how you appear ready to go again,” she crawled over to Jimmy and pulled his jeans and boxers off. “I might as well break you in for real.” She got up and pushed Jimmy’s chest so that he fell backwards onto her bed.
As Lupe pulled down her jean shorts and her panties, Jimmy could see that her pink panties were soaked dark around the middle. Finishing off with her tank top, the beautiful, caramel skinned, Puerto Rican eighteen-year-old with perky B sized breasts was now completely nude. Lupe got on top of Jimmy and straddled the prone boy. She giggled as she watched Jimmy's nervous reaction to her slowly grinding her waxed, smooth pussy against his throbbing hard on.
Reaching over Jimmy, Lupe opened her nightstand and pulled out a condom. She ripped open the packet and then slowly slid the rubber down Jimmy’s erection. He had never experienced the feeling of a condom before, and while it felt a bit tight, he didn’t find it uncomfortable or distracting.
Lupe massaged Jimmy’s now wrapped cock against her warm pussy lips for a few more seconds before lifting herself up a bit higher and lowering herself onto him. Jimmy was a bit smaller than the guys she had had sex with in the past, but it actually felt nice working with something a bit smaller; it caused her a lot less pain when bottoming out on it. For Jimmy, it was the first time that he had ever been inside a girl. He had had several blowjobs before, but nothing compared to what he was feeling right then. The warm, gripping feeling of Lupe’s pussy around his cock was something he thought could never be matched.
Enjoying the feeling of the cock inside of her, Lupe rubbed Jimmy's chest and happily cooed a little bit before beginning. The dark haired Latina began slowly moving herself up and down the younger teen’s hard shaft. Lupe lifted Jimmy's shirt up and over his head so that her hands could feel the smooth, bare skin of his chest. The pressure of Lupe’s pussy pulling on his cock as she raised herself up was like having a tighter mouth wrapped around him. Jimmy thrust his hips so that he could plunge himself deeper into Lupe, wanting to feel himself as deep in her as he could.
Barely two minutes into their thrusting though, the younger teen came, a funny, scrunched up look on his face as it happened, and Lupe could feel his cock start to soften up. Although she was a bit disappointed at how quickly things had ended, Lupe understood that this was Jimmy’s first time and that he had been really eager as a result, not just because he was having sex with a girl, but a girl he was clearly obsessed with.
“That was the greatest feeling I think I will ever get to experience,” Jimmy complimented her as he suddenly realized that he didn’t notice if Lupe had come herself. “Did, did you come too?”
“No,” Lupe politely laughed at Jimmy’s innocence and desire to make sure that she was taken care of as well. “But it’s ok; seeing that look on your face as you came was reward enough for me.”
Jimmy laughed, mostly at himself, imagining how stupid he must have looked, as Lupe cuddled up next to him. “Thanks for that, Lupe.”
Again, she had to laugh at the younger teen. “Well, you’re welcome. But you didn’t need to thank me. I did this because I wanted to, not because I felt sorry for you, pinhead. Besides, you’ll have many more opportunities to make it up to me.”
Jimmy’s face couldn’t hide just how excited he was for the future.
