Jake couldn’t believe that he was finally going to see his old friend Sarah after so many years. About four years ago, Jake had babysat his neighbor Sarah after school and whenever her parents were gone for the night or weekend. Although Jake had only been thirteen at the time and Sarah was eleven, most of the parents in their small town regarded Jake as being far more mature and trustworthy for someone his age, and Sarah’s parents never worried about leaving her with him. Over time, the two developed a strong relationship not unlike that of best friends.
Unfortunately, things took a sad turn when Sarah turned twelve. Sarah’s dad, a pilot in the air force, was transferred to a base in Florida. It had been hard on him, as Sarah was more than just someone that he would babysit, rather she was a good friend too. While he hated the fact that he had seemingly lost a friend, they did occasionally talk over the phone. This was before the wide-spread use of social media, so the two never knew how much they had grown while they were apart.
Four years after she left, Jake got an all-caps email from Sarah a few weeks after her sixteenth birthday, telling him that her dad had been transferred back to the base in their hometown and they would be back in a week. Her family was going to have a small gathering with their friends the day after they arrived home, and she wanted Jake to come. Naturally, Jake was elated with both the news that she was coming back home, and that he was invited to the gathering itself. Little did he know he was going to have another reason to be excited soon enough.
After a week that felt like another four years, Jake went to Sarah’s new house for her family’s welcome back gathering. His parents didn’t really know Sarah’s family, the Cruzs, so he went alone. Upon reaching the front of the house, he saw a sign telling guests to go around to the backyard, which he did.
As he walked into the backyard, he noticed red, white and blue streamers and other decorations hung all around the backyard’s trees and fencing, while people selected food from a large table before sitting down at one of several red-and-white-checkered tablecloth-covered tables.
“Jake,” a woman’s voice called out. It was Sarah’s mom, Suzanne, followed by her husband Lucas.
Suzanne walked over to Jake and gave him a gentle hug.
“It’s so good to see you again.”
“It’s good to see you too, Mrs. Cruz”
“Hey, Jake,” Mr. Cruz said as he extended a hand, which Jake took and gave a firm shake.
“Hi, Mr. Cruz. I can’t tell you how good it is to have you back in town. I’ve missed you guys so much.”
Suzanne scoffed playfully.
“Please, you missed Sarah, and believe me, she’s missed you plenty as well. The first few months, she was so depressed about leaving you. She’s going to be over the moon to finally see you again.” She looked over her shoulder towards the house and then back to Jake. “In fact, there she is. Sarah, look who it is,” she called out.
A petite figure looked past the small group of people she was conversing with and quickly broke out into a wide smile.
At first, Jake’s mouth stretched into a smile before it quickly changed into a shocked oval. The little girl that he used to babysit was no longer a little girl. Sarah raced over to him and gave him the tightest hug he had ever received. As she stepped back and told him how great it was to see him, Jake looked the sixteen-year-old up and down. Instead of the long dresses that Sarah had loved to wear when she was younger, the teen was instead wearing a tight gray t-shirt and a pair of even tighter blue jean short shorts that, he could tell without even seeing her backside, barely managed to cover her ass.
Sarah’s dad could see how Jake looked at his daughter, his face giving him a tired, knowing look as if to say I hate the fact that you’re looking at my daughter that way, but I understand why.
As for Sarah herself, the girl had grown, but not in all aspects. The teen was roughly five-foot-six-inches, with long, dark hair which was tied into a pair of braided pigtails, brown eyes, and her skin was a light brown, reflecting her Puerto Rican background. As for TNA, the things guys like Jake couldn’t help but immediately notice when looking at a woman, Sarah’s were still rather small, but on her slender frame, they looked amazing.
“Jake, you know my actual birthday happened a couple of weeks ago, but my parents are letting me have a small birthday party this Friday night at Ruby’s, the old roller rink, which, thank God, is still here.”
Jake nodded, remembering how he would take her there sometimes when he babysat her on weekends when her parents were away.
“You have to come! You’re the only person here I really want to re-connect with, and I want to do more than just talk to you for a few minutes like we’re doing right now. Will you come?” Sarah pleaded with her hands folded together.
Jake was supposed to help tutor a kid from school that evening, and he was seriously torn about whether or not he should keep his commitment to a fellow student, or go and spend time with his old friend that was also pretty damn hot now. Sarah helped him make up his mind by saying please and pouting while she tilted her head and stretched her interconnected hands out in front of her.
It wasn’t so much the pleading that provided the final reason for him to say yes, but rather the fact that as she stretched her arms out in front of her, it caused her biceps to squish her small breasts together and make them more prominent.
“Of course, Sarah. You know I will.”
“YES! I’m so excited!”
Sarah gave Jake another tight hug and held on for several seconds, all the while her dad looked at him with that knowing look he had given him a minute earlier.
After what seemed like the longest wait, Jake had ever had to endure, even more than the four years Sarah was away, and the week he had to wait for the party since she returned to town, it was the night of Sarah’s birthday party. Upon entering and going over to the booth where people normally had to pay, Jake told the guy behind the booth that he was there for the Cruz party. The guy smiled weirdly and gave him a small nod.
“Yes, the other…” He paused. “Guests, have already arrived. Go on in, sir. Have fun.”
Jake thanked him and opened the second door to the rink after the guy buzzed him in. Something about the way the guy paused before stating that the other guests had arrived and told him to have fun was kind of creepy. After going through the second door, Jake was able to easily locate Sarah, who was standing next to two other teenage girls he didn’t know, and he quickly realized why the guy had told him to have fun in such a weird voice. Sarah waved at him and she and the other girls next to her skated over to him.
“Jake, I’m so glad you came. These are my friends, Jenna.” She directed both of her hands towards the girl on her left as if she were displaying a prize on a game show. The blonde teenager said ‘hello’ to him. “And this is Rebecca,” she said as her hands shifted to introduce him to the brunette on her right. The girl said ‘hi’ and playfully waved at him by simply repeatedly bending her fingers after raising her right hand. “Their dads were also transferred to the base in town and we were in all the same classes back in Florida.”
Jake managed to croak out a weak hello as he looked at the three sixteen-year-olds and what they were wearing. Sarah was wearing a tight t-shirt that was decorated with a graffiti design and exposed her midriff, and a pair of shiny, metallic-looking pants that were so tight that they caused a camel toe to form around her pussy lips. She had also removed her elaborate pigtail braids and let them flow more freely as a pair of loose, non-braided bunches. Her two friends were also dressed rather suggestively, with Jenna wearing a pleated white mini-skirt, and Rebecca wearing a hot pink crop top.
Desperately needing to think of something non-sexual in order to prevent himself from growing a visible erection in front of the three sixteen-year-olds, Jake decided to ask Sarah about the size of her party.
“Is this everyone? I figured so many of your old friends would want to see you, and so far, I’m the only person here from town.”
Sarah waved off the question.
“I didn’t really keep in touch with anyone else from town when I left. You’re the only person I really cared about staying in contact with. Luckily for me, Jenna and Rebecca’s dads were transferred here along with mine, so I get to keep hanging out with my two besties from Florida, and now you, of course.”
Her words made Jake feel good about being the one person whom she really wanted to connect with upon returning to town. Still, he felt kind of weird being an eighteen-year-old guy at a birthday party that consisted of only himself and three scantily clad sixteen-year-old girls.
“Well, we’ve already got our skates on, so why don’t you go and pick up a pair and we’ll see you out on the rink. Let’s go, guys.”
Sarah motioned to her two friends and they both started to follow her. As they were skating away, Jenna bent over and grabbed her ankles, causing her mini-skirt to ride up over her ass and expose a pair of light pink panties while Rebecca started to reverse skate as she looked at Jake and blew him a kiss.
Despite the teasing from the two girls, his focus was still mostly on Sarah, more accurately, on her ass and how tight her pants were cupping her ass and practically going right up her ass crack. The view of the three teens received a predictable response from Jake’s crotch, which he had to conceal by putting his hands into his pockets and awkwardly shuffling over to the skate rental desk.
How the Hell am I going to keep myself from staying erect all night?
The four teens started skating, and everything started off innocently enough. Sometimes, the three girls would skate hand in hand as a group, and other times Sarah would hold Jake’s hand and skate with him. One time, Jenna and Rebecca came up to him from either side and each grabbed a hold of one of his hands, while Sarah grabbed onto his shoulders and the four skated as a group.
This isn’t too bad. Actually, it’s pretty fun. At least, that’s what Jake thought at first. Eventually, the girls started to dance while they skated, and some of the moves were a bit risqué, such as twerking and running their hands over their bodies. This was a problem for Jake when he was skating behind the girls, especially Sarah, whose skin-tight pants hugged the curves of her ass so well, showing off how perfect it was. It wasn’t long before he found himself with another erection that he needed to hide.
Just as his latest erection was about to hit its peak size, Sarah started to swing her arms around in circles as if she was about to fall.
“Woah, woah, Jaaake!”
Just as Sarah was about to fall backwards, Jake managed to dash forward and wrap his around her just in time to keep her from falling. In the process of stopping her fall, his hands had unintentionally ended up wrapping around the area just below her breasts to hold her up. Rather than immediately straighten her up, he unconsciously ended up sliding his hands up and over her breasts, gently squeezing Sarah’s two orange-sized tits as he did so.
He couldn’t believe he did it, but a part of his horny subconsciousness took over him and made him do it. In addition, his cock was pushing against Sarah’s ass and he was pretty sure that she must have felt it. Luckily, Sarah either didn’t notice or didn’t care, as she just giggled and straightened herself up.
“My hero. Thanks for the rescue, Jakey.” She hasn’t called me that since I used to babysit her, and the way she said it kind of turns me on.
“Oh, uh, no problem, Sarah. Just try to take it a bit slower from now on, okay?”
“Okay, Jake. You’re still looking out for me, aren’t you?”
He smiled awkwardly.
“Always, you’re my best friend.”
Sarah gave him a smile and started to skate away. As she did, Jake yet again stared at the petite teen’s tight ass.
What the Hell is wrong with me?
The group skated for about another hour and stopped to have some pizza while Sarah opened her gifts. Jake had gotten her a limited edition Woman of Action comic book, one of her favorites from when they were younger, which got him a hug and a kiss on the cheek as a reward. Jenna and Rebecca’s gifts were a little different.
Jenna’s gift to Sarah was a royal blue lacy bra with matching panties, but they weren’t even the most shocking gifts that she received. Rebecca had gotten Sarah a vibrating dildo that looked so big that Jake was sure it would go right through Sarah if she tried to insert it all the way into her pussy. Jake blushed embarrassingly, both for being the only guy at Sarah’s party and for the fact that all of Sarah’s racy gifts were being left on the table for passersby to see.
“I guess you’ve really changed since you left town. I think my gift is a little, outdated,” he sheepishly stated.
With a giggle from all three of the girls, Sarah proceeded to lay a hand on Jake’s shoulder, and one mid-thigh on his right leg.
“Don’t be silly, I still love Woman of Action, and I love your gift. I’ve just grown up is all.”
While she was talking, Sarah’s hand had slowly migrated from his mid-thigh to his inner-thigh, barely an inch from his erection, which was awkwardly stuffed into his right pant-leg. Jake’s cock twitched and stiffened further, making him worry that she would accidentally brush up against his shaft. Oddly enough, he found himself secretly wanting her to touch it, possibly so he could impress her with the size of his cock, which was almost seven-and-a-half inches long.
Despite her moving her hand up his leg, he still refused to believe that Sarah, the sweet girl he used to babysit several years ago, was actually trying to seduce him. While she and her friends might be have been trying to tease him, or maybe they just naturally always act like this, the idea that Sarah was putting the moves on him didn’t seem possible to Jake. Still, it didn’t change the fact that he wished that she was putting the moves on him. A younger girl as hot as Sarah, how could someone in my position say no if she was?
The rest of the evening played out pretty smooth. The group finished their food and skated for a few more minutes until they all decided that they had had enough. Rebecca and Jenna’s parents picked each of them up a few minutes apart. As Rebecca was saying how nice it was to meet him, she gave him a hug and gave his ass a hard squeeze. He almost yelped in response, but luckily, he managed to hide it, and no one was behind him to see the sixteen-year-old grab his left ass cheek.
After Rebecca left, it was just Sarah and Jake left waiting for Sarah’s dad to pick her up. Jake would drive himself home since he had his own car. They talked for about ten minutes, catching up on what had happened to each of them the past few years. Eventually, Jake managed to muster up the courage to ask her a question that had been on his mind all night.
“Out of curiosity, Sarah, did you, or I guess do you, have a boyfriend back in Florida?”
With a small huff, she responded, “Nah, I’ve dated a few boys, but I never really liked any of them. All the boys my age seem so immature. I guess I’ve always kind of hoped that I would find someone like you, someone who’s mature, kind and interesting. So far, I’ve never met anyone else like you.”
“Sorry about that,” Jake apologized.
“It’s not your fault that you set the bar so high. What about you? You seeing anyone right now?”
This time it was Jake that had to exhale.
“Well, I’ve gone out with a few girls, but nothing has ever really come out of them. Eighteen and I still don’t have a girlfriend.”
Sarah smiled awkwardly.
“Have you ever, you know, done it with a girl, yet?”
“Uh, I,” Jake stammered. “I’m not sure I should talk-”
“Oh, come on. I know about sex. I mean, I haven’t had sex with anyone yet, but I know about it.” She gently prodded Jake in his ribs. “Come on, tell me.”
With a look of defeat, Jake opened up to Sarah.
“Well, yes, I’ve had sex with a few girls. Some older than me.”
“What about your first time?”
“My first time was with a girl from school. She was a senior and I was a sophomore, so I was sixteen and she was eighteen.”
“Just like our ages,” Sarah pointed out, which reawakened Jake’s awkward feeling about the topic they were discussing, but luckily, Sarah started talking again. “You know, my dad has always been kind of nervous about me dating boy- oh shoot!”
“My dad, I forgot, he can’t pick me up tonight because he and mom are going to some cottage with some old friends in town. I thought that they were going next weekend, but now I remember it was today after they dropped me off. I don’t even have enough money for a taxi. How am I supposed to get home?”
“It’s no problem, I drove here. I can take you home.”
Sarah jumped at him and gave him a tight hug.
“Oh, thanks, Jake. I promise I’ll make it up to you.”
Jake was lucky it was dark enough to hide the fact that he was blushing again.
“You don’t have to make it up to me, it’s just a ride.”
“Oh, Jakey, still as kind and modest as always.”
There’s that nickname again, Jake thought to himself. God, why does that turn me on so much?
As they were talking, she was still clinging onto him, until finally, Jake suggested that they get going.
“Come on, it’s getting late.”
A few minutes later, the two arrived at Sarah’s house. All of the lights were off, including the porch lights, leaving the house completely dark. Jake parked his car in the driveway and turned off the engine.
“Well, we’re here. Thanks again for inviting me. It was a bit weird being the only guy in the group, but I still had a lot of fun.”
“Me too, Jake, and thanks for the ride home.”
A look of hesitation came to her face and she bit her lip.
“Is something wrong?” Jake asked.
“No, well, it’s just that the house is completely dark, and I’m kind of nervous going in alone. Would you mind walking me inside?”
“I don’t mind at all.”
They exited the car and walked up to the front of the house. Upon unlocking the door and stepping inside, Sarah turned on the hall lights and the porch lights. Just as Jake began to wish her a good night, she pleaded with him to stay.
“I know it’s childish, but can you just look around the house with me a bit before you go? Just in case someone is hiding somewhere inside? Please?”
Although he knew that there was little chance of such a thing happening, Jake couldn’t turn down Sarah and her cute, pouty face. He agreed and the pair kicked off their shoes and proceeded to look around the first floor, followed by the second, until there was only one room left.
“This is the last one, my room.”
Sarah turned on the light and entered the room, followed by Jake.
“Well, it seems like everything is okay. It’s pretty late, so I should-” Jake started, but was interrupted by Sarah jumping into his arms, wrapping her legs around his waist, her arms around his neck, and smashing her lips into his.
“Sarah, what are-” he tried to ask, but his mouth found itself smothered by hers.
Jake was lucky that he was moderately strong and well-balanced, otherwise, Sarah might have knocked him backwards into a wall that surely would have received a massive dent.
“Sarah, your parents-”
“Are not here,” Sarah finished. “I told you, they’re away for the weekend,” she added between repeated kisses to shut Jake up. “I told my parents that after dad dropped me off, I would get a ride from Jenna’s parents, which I never asked for. I wanted you to take me home so I could do this.”
After some gentle pushing, Jake managed to wrestle himself free from Sarah’s grip and get her to stand on her own feet.
“You did all of that, just so you could kiss me?”
Sarah playfully shook her head.
“No, not just kiss you. To show you something.”
“And what’s that?”
Instead of saying what she wanted to show him, she just did it, by pulling her shirt over her head and then throwing it on the floor, revealing a black lace bra.
“Sarah, you really shouldn’t be doing this.”
“Are you sure of that?” she said as she unhooked her bra and dropped it onto the floor.
Jake just stared at Sarah’s breasts as he huffed air in and out while his heart rate continued to climb. Her chest wasn’t flat, nor was it big for her age, they were more like large oranges. Her nipples were puffy, dark and stood erect. The only word that Jake could really think of to describe her breasts was ‘perfect.’ He must have been staring at her for nearly half a minute without saying anything as she just smiled, enjoying the fact that he was so mesmerized by her body.
Normally, most people would try and think about whether or not they should go through with something like this, but Jake already knew he wanted this to happen. Sarah was of legal age, and the two of them, despite being physically apart for so long, were best friends. To be honest, the only real concern of Jake’s was getting caught by Sarah’s parents, but then he remembered that Sarah said they were gone for the weekend.
“Are you absolutely sure that you want to do this, Sarah?”
She gave a small smile and nodded.
“I know we’re different ages, and technically, the last time you saw me, you were babysitting me, but over the years, when we’ve been emailing back and forth, I’ve always thought about how I wanted to ask you out so much.” Sarah started to look nervous. “When I turned sixteen and found out that I would be moving back here, I thought that I would finally have my chance to ask you out, but when I saw you, I just thought that I needed to have you right away. What about you? Do you want to do this?”
This time Jake was the one with the confident smile.
“I’ve felt pretty much the same way, at least about wanting to date a girl like you. Wanting to do anything physical with you didn’t happen until I saw you last week, I didn’t fantasize about you sexually or anything when we were chatting, you know, that would be weird and-” Jake stuttered as his confident smile was replaced with an awkward, embarrassed one, but thankfully Sarah laughed nervously like he did.
“No, no, I get it. I guess we were both pleasantly surprised when we saw each other a few days ago.”
The words made Jake feel instantly relieved and relaxed.
“You know, you wouldn’t believe how hard I had to try and hide how attracted I am to you all night.”
“Well you didn’t do a very good enough job; I could feel your cock sliding in between my ass cheeks when you caught me and helped me up, not to mention you squeezed my breasts for several seconds too,” Sarah responded, finishing with another giggle.
“And you didn’t mind?” Jake asked, worried that despite what they were about to do, maybe she felt upset by what he had done at the roller rink.
“Getting your attention was the whole point of tonight. Based on what I felt poking me through my pants, I figure I probably did a pretty good job.” Sarah put on another pouty face. “Was I wrong?”
Jake’s response was to close the half-meter gap between them and start to kiss her gently. His hands found their way down Sarah’s back to her ass and he gently squeezed her small cheeks as she started to rub his cock through his jeans. After a minute of making out, he removed his shirt and led Sarah to her bed Laying her down gently, Jake tried to pull Sarah’s pants off, but he was having a really hard time sliding them off since they were so tight, making the girl laugh at his predicament.
“Jesus, Sarah. How did you even get into these things in the first place?”
“With the help of my two friends you met at the rink tonight. When I told them my plan to seduce you, Jenna insisted I try these pants of hers to catch your attention. You have no idea how hard it was to skate in these things.”
This time Jake laughed.
“Well, you weren’t the only one who had a hard time skating because of them. I had an almost constant painful erection stuffed into my jeans while I was skating behind you.”
Jake gave one final energetic pull, finally managing to remove the super tight pants. Taking in the sight of the petite teen’s body, his eyes made their way up her skinny brown legs, over her thighs and finally came to rest on her pussy. Her pubic area was shaved clean, save for a small patch of short pubic hair located a few centimeters above her clit that had been shaved into a little heart. The sight caused Jake to laugh, to which Sarah looked at him with slight annoyance.
“What’s so funny?”
“That,” he pointed to the heart shape above her pussy. “I’ve never seen such interesting grooming work like that before is all. It’s really nice.”
The response made Sarah smile, relieved that he wasn’t laughing at her.
“I thought you might be impressed by the work I put into it.”
“I am. I can’t believe that you did that just for me.”
Sarah giggled and her smile grew a little bigger.
“You’re worth the effort, Jake. Now, how about you get on top of me and do something besides talk.”
Without any more words, Jake climbed on top of Sarah and the two began making out. The sensation of Jake’s lips reciprocating her kiss and his body pushing against hers sent shots of ecstasy throughout her. Goosebumps that had formed on her body due to the cool temperature of her room when she first disrobed began to fade away as Jake’s body heat warmed her up. Breaking their kiss, Jake lowered his head and started to suck on her tender right breast. His left hand slowly made its way down her tight abdomen and past it.
Neither of the teens could believe what was happening, but they also knew that they wanted it, needed it. Jake continued to suck on Sarah’s breasts for another minute before lifting his head up. He gazed deeply into her brown eyes before slowly leaning in and placing a kiss on Sarah’s lips. One of his hands began to journey back up Sarah’s body, eventually reaching her small, firm breasts, while the other was sliding up her left thigh towards the most sacred part of her body.
After several aching seconds, Jake’s hand found its way to Sarah’s swollen, wet pussy lips. The feeling of having another person touching her there rather than herself was both a first and a feeling that was easily a hundred times better. As the tips of his fingers gently ran over her sensitive clit, she realized that not knowing what Jake was going to do next was what made him touching her more exciting than her touching herself, where she always knew exactly what she was going to do to herself next.
As Jake’s fingers began to slowly insert themselves into Sarah, he stopped after he had inserted the tips and broke their kiss to look at her with a concerned face.
He began to ask, “Sarah, since you’ve never been with a boy, this could really-” but Sarah cut him off.
“I might be a virgin in the sense that I’ve never had sex with a boy before, but I’m not new to having things in there. I’ve been using a dildo the past few days to get past the more painful bits, and I managed to go pretty deep inside myself. I don’t think this will hurt as much as you think it will.”
The words caused Jake to relax considerably. Knowing that Sarah was not a complete virgin to sexual matters took a lot of pressure off of him, both in terms of how painful her first time would be, and fear that he might scare her away from having sex with him in the future if she attributed the pain to him. He started to slowly insert his index finger into her pussy.
“Oh, my God!” Sarah gasped.
Even though she had inserted much larger things into her pussy before, the anticipation of eventually having Jake’s cock in it caused her pussy to tighten hard around his finger. After a few pumps, Jake added his middle finger to his poking and started to increase the pace of his finger thrusts. Sarah let out deep breaths and even deeper moans as he slid his fingers in and out of her wet slit.
After making sure that her pussy was well-lubed with her own juices, Jake got up and removed his pants. Sarah marveled at his cock. While not as thick as some of the toys she had tried on herself, he was definitely just a bit longer than anything she had used. A devious little smile crossed Jake’s face, highly satisfied with Sarah’s own devious little smile as she looked at his erect cock. He went back to the bed and positioned himself over Sarah and prepared to enter her before realizing that he had hadn’t put on a condom.
“Aw, shit. Sarah, you wouldn’t happen to have a-”
A shiny object suddenly caught his eye, cutting him off as Sarah retrieved a condom packet from under her bed.
“I’m fully prepared for tonight,” Sarah stated as she handed the condom to Jake, who breathed out in relief that the night hadn’t been ruined by neither of them having protection ready.
Jake unwrapped the condom and slid it onto his shaft. As he began to aim the head of his cock towards her pussy, Sarah began to worry. Even though she had been practicing for this with her dildos for a while, she remembered how her pussy reacted when Jake’s fingers were inside of her, and those were just fingers. In an effort to alleviate any potential pain, and to take control of the situation as she had been doing all night while she seduced Jake, she made a proposition.
“Maybe you’d better let me climb on top of you and control how deep you go into me. I’ve never had a dick in me before, and I think it might hurt a bit. You don’t mind, do you, Jakey?” Sarah asked while giving a sexy little pout and using the nickname she knew would entice Jake to do anything she wanted.
Jake couldn’t refuse that face, that body, and the sexy way she used his nickname; there was almost nothing he wouldn’t do for Sarah. Besides, by that point, he didn’t care how it happened, he just wanted to get his cock into Sarah’s pussy.
“Of course, whatever you think will make it better for you,” he replied as he got off of Sarah and positioned himself in the middle of the bed on his back.
With a smile, Sarah straddled Jake by placing her legs on either side of the older teen’s athletic body. Once she was in position, Sarah slowly leaned down and pushed her lips against his once more, passionately kissing the boy who used to babysit her when she was a young girl. This time, though, Jake allowed her tongue into her mouth without any hesitation. As they kissed, his cock rubbed against her abdomen, and given just how turned on he was, he was worried that the rubbing would make him cum before he even made it into her pussy.
After a few seconds, she released the kiss as Jake’s head followed her up, wanting more. She leaned down and gave his pecks a few kisses before raising her tiny body over his raging hard-on just below her blazing pussy. He smiled at her as she gripped his throbbing cock in her small right hand and started to rub the head of it gently up and down her wet pussy lips. The sensation caused by even the slight contact was highly amplified by the anticipation of what was going to come next, causing her to let out a moan as she let the tip of his cock slide slowly into her pussy. Warmth began to engulf Jake’s shaft as Sarah lowered herself onto him, causing him to moan out loud this time.
As she continued to insert Jake’s cock deeper into her pussy, Sarah screeched lightly. Jake placed his hands on her hips, holding her up slightly so that the task wasn’t as strenuous for her. The deeper his cock probed into her pussy, the more intense mixed shots of pleasure and pain shot throughout her body. Eventually, they had managed to insert a little over half of his cock into her pussy, where it was obvious that he had made it into her as far as was physically possible for her take.
Reaching as far as she could, Sarah began to slowly bounce herself up and down Jake’s cock, getting a little bit of help from with his hands on her hips. She let out a moan of pleasure each time she forced his cock as deep into her as she could with every thrust. Losing himself in the amazing feeling of his cock pounding Sarah’s tight pussy, she began to push her down harder on his shaft, even though there was no way to get more of his cock into the petite teen, he kept trying, and Sarah didn’t protest.
“Oh, my God! This is the best feeling I’ve ever felt. I don’t think a dildo will ever work on me anymore. Your cock is so good. Please, fuck me harder, Jake.”
It didn’t matter that Jake’s cock repeatedly slammed into the back of Sarah’s pussy, it being too big to fully fit inside of her, the teen never expressed any sign of discomfort at being continuously fucked by a cock that was too big for her pussy. In fact, Sarah continuously praised Jake and giggled excitedly at the feeling of his cock filling up her pussy.
“Oh, oh, Jake, do you mind if I lie down for a while? It’s getting a bit uncomfortable holding myself up.”
“Of course, Sarah.”
Sarah slid herself up and off of Jake’s shaft, who got off of the bed and stood at the end of it. As Sarah laid down on the middle of the bed, expecting Jake to climb on top of her like she had on him, instead he grabbed hold of her ankles and pulled her to the edge of the bed. The sudden pulling prompted a little ‘Ooh,’ from Sarah as she was dragged to the edge of the bed, followed by giggling as she suspected what Jake was going to do next.
Moving her to the very edge of the bed, he pulled her left leg up and rested her ankle on his right shoulder, while his left hand held up her right leg under her knee, causing her to spread her legs open. Since Jake had his hands full, Sarah assisted him by taking hold of his cock and aiming it towards her pussy. With her assistance, Jake entered her again and started thrusting.
“Oh fuck, Jake. You’re filling me up so good. There’s no way my first time could feel any better!”
“And your pussy is so tight, Sarah. Fuck! I’ve never felt a pussy grip me like this before.”
“That’s because you’ve never been with a younger girl like me before. I might not have big tits or a big ass, but I do have a tight little pussy.” She looked at him with suddenly intense eyes. “Now, no more talking, just fuck me harder!” She commanded him, and Jake was happy to comply as he thrust in and out of her faster.
To change things up, Jake stopped pumping himself into Sarah as fast as he could and instead, pulled himself out of her until only the bulbous head of his cock was still inside her. Just as it seemed like he was going to remove himself from her, he roughly slammed himself all the way back into her. The first time he did this, it made Sarah tense up and squeeze her eyes shut. Unable to make herself scream, she just left her mouth wide open as her brain processed the pain of her pussy being slammed so hard.
Although Sarah had shoved some pretty big things into her pussy before, she had never done it with so much force. As the pain started to fade and be replaced by feelings of pleasure, she managed to make her body relax and was able to speak once again. Each of the older teen’s thrusts caused the younger one to let out an ‘ahhh’ each time she was harshly jabbed by his cock, but she soon began to smile at him devilishly and her cries of ‘ahhh’ were replaced by ‘yes’s each time he thrust back into her.
Jake maintained this rhythm for about a minute before he became overwhelmed by lust and went back to fucking Sarah as fast as he could. Sarah continued to cheer him on until she began to herself begin to climax.
“Oh, God, Jake. I’m gonna cum,” Sarah cried out.
Within a second, he could feel Sarah’s pussy tighten even harder around his cock, and juices started to flow over his shaft and in between her legs before dripping onto her bed and the carpet. Along with providing extra lubricant for his cock, the further tightening of her around his cock caused increased pleasure for the both of them, but Jake in particular, who was approaching his own orgasm.
Instead of announcing it, Jake just gave a series of grunts and moans as he came into the condom. After giving a few more small thrusts, he slowly withdrew his cock from Sarah and breathed deeply as he removed the condom and threw it into a wastebasket next to a desk.
“Well, I guess I should be glad we were apart for all those years. If we had stayed together this whole time, I don’t know if what just happened would have actually end up happening,” Jake reflected.
“I suppose. Maybe we would have just stayed friends, or maybe gone out when I was older. I have to admit, though, it was so fucking hot getting the chance to seduce you and do it just a few days after we reconnected.”
As Jake cleaned himself up, Sarah stretched out on her bed for a few seconds before sitting up to tell Jake something.
“You know, it’s too bad we had to use that condom. I just got my doctor to allow me to take birth control, so next time, we won’t have to bother with a condom and you can just cream in my pussy.” She reflected for a moment before adding, “And maybe you could try fucking my ass too. I’ve never even put a toy in there yet, so it really is 100% virgin. What do you think, Jake?”
The thought of getting to fuck Sarah with no condom instantly started to trigger his imagination, and give him a new erection, which caused Sarah to smile. As he turned to face her and say something, even though he didn’t know what, he saw that she was already holding a fresh condom in her hand.
“Looks like you might not be able to wait until next time. At least, you won’t have to wait to try out my little ass.”
They laid in Sarah’s bed for a few minutes, Sarah snuggling her face into Jake’s chest, pushing her body against his while Jake wrapped an arm around her shoulders. After a while, Sarah broke the silence to ask Jake a question.
“You know, Jake, Jenna and Rebecca asked me that if you were good in bed tonight if they could have a turn with you since you’re so cute. I said sure, as long as I get to join them, since I told them that you’re mine. Would you be okay with them joining us one day?”
The only response Jake was able to give was a wide-eyed, open-mouthed look of disbelief. Sex with three hot teens younger than me. How the Hell did this end up happening to me? It goes without saying that he agreed to her terms, followed immediately with them going another round before calling it a night. They both fell asleep in Sarah’s bed, wrapped around each other, and glad that the two of them were back together again.