Finally summer holidays had arrived! Brad had just finished his sophomore year in high school. He had even managed to raise that ever struggling geography grade so his parents weren't going to insist he worked on it during the holidays. This was actually a bit of a surprise, so for now the grand plan was to practice football and hang out with his friends and then relax as much as possible in between.
"My condolences .. yeah? .. oh? .. sounds nice! .. oh wow, that's kind of short notice .. I'm pretty sure Ted has to work, but maybe I can bring Brad". Brad had stepped through the door while his mom, Evelyn or Lyn to her friends, was on the phone. He promptly got her attention enough to show her the piece of paper that should spell total freedom for the duration of the summer. "Ooohh nice! I guess a bit of moms tutoring paid off? ... Huh? oh that was for my son, he just handed me his grades. Would you believe a bit of studying with his mom earned him a respectable grade in Geography? What are your plans for the next couple of weeks honey?" Lyn had looked up at Brad and angled the phone down a bit. It wouldn't sound much different for the person on the phone, but it was enough for Brad to register she was talking to him again. "Ohh, not much, just hanging with a couple of mates I guess". "Sure we would love to help out. Me and Brad. For the full 2 weeks. I look forward to seeing you girls again too". Lyn hung up and put the cell phone down on the kitchen table.
"Mom, who was that and what did you just volunteer me for?". "Volunteer? That sounds work-ish! you call 14 days vacation in Florida work?" "I only heard your half of the conversation" he countered. "You said we were going to help out, that sounds awfully work-ish to me". Brad should have expected it by now. That comment was bound to start the usual speech about how healthy it would be for him to start making his own money. Brad was doing well in school, but mostly by putting in the extra hours. Whenever he wasn't studying he was running, lifting weights or hanging out with friends from the football team. He usually claimed the latter was extra training, but in reality they would usually spend an hour on a field or doing something training related and then a couple of hours hanging out. But training or not, he just couldn't see how he was going to fit a spare time job into that schedule.
"Alright, alright. Maybe I can tutor some middle school kids, or help the coach out with something during the summer". Brad figured one of those options could be called a summer job, without actually taking too much time away from hanging out with his friends. Besides with a little luck he could spend the time tutoring Sara. She lived just down the road, was one year his junior and always in need of help with math. To top it all off, Sara's mom absolutely adored Brad, so he was sure all he had to do was ask her if Sara needed tutoring.
"You still didn't tell me what that phone conversation was all about though!" Brad had to remind his mom. Lyn had pretty much been talking as if Brad had heard both ends of the phone conversation, somehow without revealing any more details than Florida and 2 weeks. "You remember my high school friend Amber?..."
Lyn had gotten pregnant in high school. Both Ted and Evelyns parents had been very supportive of the couple when they decided to keep the baby. Hence Brads father had managed to go on to college to finish his education and Lyns social life had recovered quite well after retaking just one year. By the time Lyn was through high-school she was tight with a new group of girls. A few of her friends went out of town for college as soon as they were through high school and wasn't around much, but Amber went to a college nearby and had stayed close until Lyn and Ted had to move for Teds new job. Hence, Brad had faint memories of most of his moms high school friends, but since Amber had been around longer she was the one he remembered best.
Brad hadn't seen Amber since he was 6, but to this day she was still his favorite babysitter. He remembered her as a very large woman, despite later learning she was much lower and thinner than Lyn. But then what grown woman isn't very large when you're 6? The memory that earned her the place of favorite sitter was one particularly hot day. They had gone to a secluded lake and Brad had wanted to go swimming, but they hadn't brought any bathing suits. Brad, being just 6, had simply ditched his clothes and jumped in before Amber could protest, forcing her to go in after him. She had stripped to panties and a t-shirt, both white incidentally, and gone in with him. They had played around in the water for about an hour, then spent the next half an hour drying up in the sun.
Even at age 6 brad had found the image of Amber in completely transparent t-shirt and panties extremely interesting. To this day he could recall every detail of her silver dollar sized areolae, how her nipples had stuck straight into the air, how smooth her pussy lips had looked (although he didn't give the lack of hair a second thought at the time) and how he had wished he was the piece of fabric in her panties clinging to the crack in the middle of her crotch. Even after finding porn on the internet, the memory of Amber was his favorite jack-off image.
Lyn finally started explaining the phone call. Amber had inherited a cottage in Florida from a deceased uncle. It was reportedly big enough for 5, but the uncle had been ill for a few years, so the cottage was most likely neglected. Amber had seized the opportunity to make an impromptu high school reunion for her closest friends. The way she figured it, they would spend a couple of days shining up the place so it could fetch a higher rent and then get in a weeks vacation of their own. Amber was recently divorced and the 2 other women that would be coming had never married for some reason, so she had asked Lyn to bring her husband in case they needed the muscle. Lyn had figured Brad would make a decent stand in for his dad with the way he kept in shape, maybe even better in some respect, being so young and fit as he was.
"Just how much will I be filling for dad, mom?" The words had flown out of Brads mouth on their own accord. He was almost shocked to hear his own, hidden suggestion. Despite his own shock Brad took the opportunity to check his mom out. He told himself it was just to emphasize the point. She was 5'9, had smooth light brown hair that reached the bottom of her shoulder blades. Her eyebrows were perfectly kept. Her nose was long and thin, pointing ever so slightly upward. Her eyes were a light greyish blue. She had nice D-cup breasts, a slim waist and full, round hips. She was wearing a v-neck shirt that showed just enough cleavage and a tight skirt that showed off her hips nicely.
Lyn didn't flinch. She just reacted with a cheekish grin and started "Not THAT much, I have plenty in your dads.." Her face suddenly changed to a more serious look "oh! I wonder if that's why.. I hadn't thought of.. " "Of what mom?" Brad pressed. "Oh nothing! In about 5 years get me drunk and ask me again, then MAYBE I will tell you! But if my suspicions are correct you are going to have one hell of a nice vacation." With that she gave the now very confused Brad a coy smile.
The rest of the week went by pretty fast. Brad spent most of the mornings doing chores in the garden or the garage for his dad, or tutoring Sara. Unfortunately he was ONLY tutoring math. His dad had surprised him on a few occasions. It was a 9 hour drive from where they lived to the cottage, so Lyn had decided they would drive there. Brad wouldn't be taking his drivers license for several months, but his dad had been teaching him stuff about driving for a while. Now the teachings took on a whole new urgency. He took Brad out practicing on empty parking lots, and even in an abandoned industrial area once.
One night when they had been practicing particularly late, his dad handed him a cold beer when they got home, sat him down on the porch and proceeded to have the talk. Brad didn't exactly need the warning about pregnancy, as he had spent most his childhood listening to the stories about his mom bringing him, books and diapers to high school classes. He was also relatively sure he wouldn't be catching something nasty should he fail to use rubber once or twice. A senior at school had contracted something really nasty recently, causing almost all the other parents to get their kids tested. Besides he was pretty sure his first would be Sara, and he would also be her first.
True to Brad's history his dad skimped past the 2 subjects pretty fast, and, to Brad's surprise, went on to explain how best to please a woman. He told Brad how, if he was good enough in bed, he might actually be able to keep a couple of willing lovers, which would be far more satisfying in the long run than jumping from bed to bed. He explained how a few strategic touches in not so obvious places could bring a woman in the mood, how women could sometimes react to even the most sleazy compliments, and how some women could actually orgasm just from a practiced tongue on their nipple. The lesson ended with Ted demonstrating the light touches combined with the right compliments on an unsuspecting Lyn.
Brad's mom woke him at 7am Saturday. He grabbed a shower and went into the kitchen to find a very solid breakfast waiting. "Eat up honey, we'll pretty much be driving for 9 hours straight, so lunch is going to be very light". They had been on the road for 2 hours by the time Brad found out why his dad had been giving him driving lessons. His mom pulled over and said ”roads here are pretty straight, you're OK to drive aren't you?”. Brad found himself driving for 5 hours straight, only letting his mom drive for the 5 minutes it took him to inhale lunch. As they got closer to the cottage, the roads got smaller and a lot more twisty. That's when his mom took back control of the car.
No GPS in the world was going to lead them to the right cottage, so they met up with Amber by the nearest convenience store. Brad recognized her immediately, despite the change in perspective from 6 year old boy to nearly full grown teenager. Full, black hair with a hint of large curls, green eyes, a very small nose. Her breasts were slightly smaller than he would have thought, being small c-cups, but they looked perfect to her petite body. 15 minutes later a car with two tall, slim women arrived. One had blonde hair with a hint of red, the other was fully blonde. Her hair wasn't blonde all the way to the roots though, causing Brad to suspect she was bleaching it. The red-blonde had very full D-cup breasts, the other had 2 gorgeous F-cups! Brad felt his cock twitch at the sight of the 2 women, despite suspecting it was his moms friends. A cheerful greeting from his mom and Amber quickly confirmed his suspicion. ”Emma, Pat, welcome. You guys look great”. Brad's cock definitely agreed. Their outfits weren't bad either. Like a couple of teenagers they were both clad in tight sleeveless t-shirts that showed off a bit of midriff and light summer skirts.
When they reached the cottage, it was clear it hadn't been used for a couple of years, but at least the roof and all windows were intact. Amber made a beeline to the kitchen in order to get it clean and start dinner. ”There should be 5 bed spaces, so why don't the 4 of you figure out sleeping arrangements”.
There were 5 doors in the hallway. The first one was to the communal bathroom. It looked a bit odd to Brad: not only 2 sinks, but also a wide shower cubicle with 2 shower heads and a big spa. The second room held a small double bed. To Brads surprise Emma quickly said ”I guess this is us Pat?” and they both went in. Brad was sure the 2 fully grown women would have to lie pretty close to share that bed. In fact it was probably going to be a source of a fantasy or 2 during the vacation. The next room held a slightly larger double bed, the third held a single bed and the final room was locked. Lyn took one look at the double bed and quickly proclaimed ”Well, I'm NOT sharing that thing with anyone, least of all my own son. I'll take the single bed, hopefully for Amber there is a bed in the locked room.” ”But mom! What if there isn't?” ”Well, I'm sure you and Amber can work it out. She's not shy, and she won't kill you when your hand 'accidentally' touches something sensitive”. ”MOM!”.
From the moment Brad had stepped out of the climate controlled car, he was assaulted by the Florida heat and humidity. As they reached the cottage he dropped his shirt and just paraded around in his bare torso. Brad figured if the girls could show off, so could he. As it turned out he was wrong though; the women were only about to show off. Emma and Pat had barely entered the cottage before they had changed to the smallest string bikinis Brad had ever seen. Their tits were only just covered with 2 small triangles. Emma's bikini was so tight over her d-cup Brad could clearly see the outline of her areolae. Pat's didn't leave a shape on the bikini in the same way, but Brad would swear he could see the edges of the colored circle under the edge of the small triangle patches. He took a careful look at the crotches of their bikinis to confirm that the bottoms were hiding as much, or rather as little, as the bikini tops.
Brad quickly grabbed the garden shears and went outside to assault the wilderness around the cottage, first of all to get his all too obvious tent away from the gaze of the ladies, second to get the tent under control before dinner. This was of course a futile attempt. Not that his erection didn't go down, but the second he caught sight of Emma and Pat the erection was back with a vengeance. To make matters worse both they and Amber were very obviously admiring his trimmed body. After dinner the women got a glass of wine each. And Brad was treated to a cold beer.
They sat down in the couches in the living room. Lyn looked at Emma and Pat and asked ”What's up with the 2 of you volunteering to share the small bed?” Emma was first to answer ”Uhm, well, we ended up being roommates in college, and after sharing guys for a couple of years we found out we could be just as good to each other without a guy in between.” Then Pat took over ”yeah most those college jocks would just stick their meat in and do the deed. If they even know what a clit is, they go directly for it. Having another woman going down on you is much better! Emma knows how to start massaging the outer part of my labia then...” Pat then proceeded to mention the different parts of her pussy in pretty much the same order Brad had heard from his dad the night before. As Pat was talking Amber inadvertently put her hand in her crotch and started tracing the different parts as Pat was talking. Brad was definitely getting a thorough course in female anatomy. Amber had already leaned back in her chair and put one foot up on the seat, giving Brad a full view of her panties if he as much as glanced in her direction. With her moving her fingers around the area he could no longer help but look. He was a little confused at first, he was sure he should be able to see the cloth even if she was wearing a skimpy thong, it turned out she wasn't wearing panties at all. Brad was being treated to a full view of her naked pussy, complete with comments on the names of the different parts from Pat.
Brad leaned forward to try and hide his ever worsening boner. As he moved, he openly stared at Amber's crotch. She got the hint, but instead of covering up, she just made it less obvious that she was showing off to him. Lyn was the first to stand to go to bed. ”It's been a long drive up here, I'm pretty tired already. I think I'll take a bath and go to sleep”. Emma was fast to respond ”Yeah I need to hit the shower too, say Lyn! That cubicle is pretty big, you mind if we join you?” ”Alright, but you two stay in your half of the cubicle”. With that the 3 women left Amber and Brad alone.
Amber was quick to up the ante. ”You don't have to lean so far forward you know. It doesn't do much to hide anything” With that, she got up, went over to sit next to Brad and swung her legs up so she had them across his lap. ”Well, you're certainly giving me a view! It's almost better than I remembered” Brad replied, as he openly took a good look at her pussy. ”Remembered?!” Amber nearly shouted. She hadn't forgotten the episode at the lake, she also wasn't surprised he had gotten a good view of her tits. What she hadn't registered at the time was that her panties were just as transparent.
”Anyway, who's sleeping where?” Brad explained he had one of the double beds, and Amber would have to find the key for the locked room. ”Oh, that's not a bedroom, it's the broom cupboard!”. ”Ooohh, I guess I'll take a couch then” Brad offered. ”No way, I used to do that as a kid, your back will be sore for a week! We're sharing that double bed”. Brad protested ”but what about .. ” he looked down at his crotch. ”With you next to me it will be like that all night!” Amber just smiled and answered ”Promises promises ..”, ”huh??”, ”Just don't poke my back or my stomach when there is a perfectly good spot for it further down”.
Brad couldn't believe it. This gorgeous woman had been a fantasy of his ever since he started playing with his own manhood. Was she practically telling him they were going to fuck, or just telling him she wouldn't mind if he rested it in her crotch? He decided it was probably the latter. ”Now why don't you go get a shower and get ready for bed, I'll clean up here and be right in” Amber offered. ”Sounds like Emma and Pat are still in there”. They had seen Lyn come out and go to bed long ago, but the showers were still running. ”Not that they would mind you joining, but we have our own cubicle, did you miss that?” Yes he did. In splitting up the sleeping arrangements he had only looked at the bed from the hallway and tossed his bag onto it.
As he entered the bedroom he saw what she meant. At one end of the room was a small door to a toilet and shower cubicle. Of cause the shower cubicle itself was made of clear glass. Brad stripped and went into the shower without giving the water time to heat up. The first few seconds of cold water were doing wonders for his member. It had been trying to set new size and stiffness records for the past 2 hours straight. Now it was finally subsiding a bit. That is, until he felt the shower door open and another body step into the cubicle.
”Hey stud! I need a shower too! Between you, Emma and Pat I bet the hot water will be gone pretty soon”. He turned around to see a completely naked Amber standing there next to him. She put her arms around his neck and leaned in for a kiss. At first it was just lip to lip, then she opened her mouth a bit and pressed her tongue against his lips. He quickly got the point and opened up his mouth. While their tongues were wrestling Brad put his arms around Amber's lower back and pulled her close. At first his cock was trapped between their bellies, but he repositioned so it stuck straight out and found the gap by her crotch. He pumped a few times. His cock wasn't inside her, but it was trapped between her legs, and as he moved, the head was grinding along her pussy opening. Her outer pussy lips gently caressed the top and sides of his penis head, her thighs more roughly rubbed the lower sides of his penis. The movement was causing a series of low moans from Amber. Brad only moaned once. After just a few pumps he had had enough and was violently shooting sperm in between Amber's legs, on the wall behind her and down her legs.
”Oooohh, that was fast” Amber failed to hide the disappointment in her voice. ”I.. I'm sorry…, but what did you expect? I've been rock hard due to 3 gorgeous women showing off the past several hours”. ”Oohhh it's alright babe, you just surprised me. You're still young, I'm sure you will be ready again in no time”. As she spoke, she grabbed his cock with one hand and started lightly stroking, while she was using the tip to tease her own clit. Brads cock hadn't lost any size at all, only a bit of hardness, but he was rock hard again in seconds. Amber lifted one knee to the side of his ribcage and pressed up against him. Brad grabbed the leg to help her hold it, and with the other hand he reached around her, put his hand on her ass and pressed her pelvis against his. He grinded his cock against her opening a couple of times before she reached down, placed his head against her opening and guided him in. The feeling was sensational. Like a thousand soft fingers reaching around his cock pressing evenly on it from all sides.
Another series of moans escaped Amber's lips. Brad felt the walls of her pussy contract in small rippling motions. ”ohh, that feels nice.” Amber exclaimed as the rippling stopped. ”Now start pumping that lovely piece of meat into me!” Brad did as instructed, then remembered his dad's words about making it good for the girl. With one hand holding Amber's leg, he tried letting go of her ass, but that meant giving up too much control. Amber must have sensed his dilemma, because she lowered her own hand to her clit and rubbed for a few minutes. Then she reached around his cock and held her fingers out so she was caressing his balls with every stroke he made into her.
“HAAaaaiiihhh” Amber stopped her own long pant by holding her breath for a couple of seconds. Then Brad felt her pussy contract again, more violently this time. He just kept pumping, straight through what he would later learn was her orgasm. He had wanted to make this session last, but the sensation made him want to shoot his juice into her baby growth chamber. He sped up the pace of his thrusting. In the midst of the crazy movements his ring finger slipped into Amber's butt hole. He felt his own finger against the bottom of his cock, and the feeling made him squirt instantly. He pushed his cock in as far as it would go, and enjoyed the feeling of his semen rushing through his cock. He could even feel it being pressed out again around the head of his penis. With his second and third squirts he felt Amber's pussy clamping around his cock again. “Aaaaiiiiuuuuhhooooohhh!!” She screamed into his ear while she was experiencing the second part of her double orgasm. He let go of her leg, and was struggling to remain standing. Amber slumped forward and rested her head against his shoulder.
“oh-H-wo-h-ow!” Amber was speaking while trying to catch her breath. “I've never come so fast from a man before and rarely had a double climax, who's the lucky girl you've been practicing on?”. “Pr-Practicing? I didn't do anything but hold you and thrust. Besides..” he almost whispered the last part “this was actually my first time”. “Well, what can I say, your cock just feels fantastic! Hang on, this was your first?!” “uhm .. yes”. “Holy sh..! You've got talent kid! You're already on par with your dad” Brad decided to let that piece of information slide for now. “No woman will ever want to leave your bed again. This is going to be the best vacation ever!” Brads cock gave a small twitch at the thought of doing Amber every night for 14 days straight, and maybe even meet up with her after that.
When they were done gasping for air, they started cleaning each other off. Amber began by dropping to her knees and using her mouth to clean Brad's cock. Brad in turn did the same to her tits. Then, after carefully rubbing away as much semen as possible, dropped down and used his tongue on her pussy. Thanks to his dads instructions and the graphical demonstration he had gotten earlier, he soon had Amber gasping and moaning again. It felt good to give an experienced woman like Amber this much pleasure.
All done rinsing off, Amber stepped out, grabbed a towel and started to dry Brad off. The way she did his back was very interesting. She stood in front of him, reached around him to his back and pressed him up against herself. His cock was certainly dry by the time she was done with it, and she did a nice careful, but thorough job on his balls. She then handed Brad the towel, and he returned the favor using the same technique on her back. For her tits he turned her around and pressed her back up against himself, then made sure the tits were really dry. Of cause the towel slipped for him a couple of times while he dried her tits and pussy.
Brad finished up at Amber's feet, then put the towel on the rack. When he looked to the bed, Amber had thrown herself down on her back in the middle of the bed, with her legs spread. She looked up and said “I guess you're right, this is a fairly small bed. You think you can find somewhere to put yourself?” Brad smiled, knelt down on top of her and started kissing. “I'm quite comfortable right here, you?” “Hhmmm .. I got something poking at my stomaaahhh… Whatareyou-ohmygodalready?” While Amber was complaining about his dick he had repositioned and shoved it into her pussy, all the way to the balls. “What was that?” Brad asked with a smile. “Ohh, much better, right where it belongs! You're incredible, ready again so fast?” “Well, I've got the hottest babysitter on the planet for inspiratiommm” She closed his mouth with a kiss. Nothing was said again for a while, they were just kissing and making love. Brad made sure he massaged her love button with his pubic bone, and he was rewarded for his effort. After 10 minutes they were both pretty close, but Brad didn't want this to end. He slowed down his movements which only pushed Amber faster over the edge. To limit her movement on his cock he leaned down hard and pinned her to the bed. As Amber came even harder this time than in the showers, she pressed herself against him and bit into his shoulder in a futile attempt to muffle her own scream.
After she had calmed down, she looked up at him and asked “You didn't finish?” “No, I don't want this to end just yet.” “Impressive, but then I guess third load is easier to hold back. It's a shame though, I had hoped to come simultaneously again, it was great in the shower I can hardly imagine what that feels like in a bed.” Brads gave her a coy smile “Challenge accepted”, “Yeah right” Amber responded. Brad bent his back and managed to get his tongue and his lips working on her tits, while one hand was now giving her pussy and clit the same treatment his tongue had given them earlier. “Oooohh shhieeesh, that might actually work” Amber moaned. After another 5 minutes Amber was worked up again, and Brad was ready to fire. As he felt her pussy clamp down on his cock again, he made a couple of extra hard thrusts and then he was shooting into her. “OOHHh YEEESSSss! Put your baby juice to good use darliIIIIIng”. Amber's legs were locked around Brad, and while her heels were pushing him into her, her thighs were squeezing Brad from the side. Luckily they were squeezing his hip or Brad thought he'd have a hard time breathing.
All spent, Brad simply slumped down on top of Amber. They remained like that for about half an hour before Amber spoke. “I wish I could keep you in me all night like this, but you're getting a little heavy”. Brad's cock, although much softer now, hadn't left Amber's pussy. Brad used his knees and one hand and took his weight off Amber without moving. Then he put his free hand around her butt and turned both of them over, his cock never leaving its new home. “Ohh god, naughty boy. You're a wealth of impressive surprises!” He was even surprised himself, both that it worked, and that the movement had caused his cock to come to life again. They had sex once more in the cowgirl position, then fell asleep spooning.
---
This was my first story. Let me know what you think :-)
