Ashley's Initiation at the Pool

Everyone is over 18.

--- ARTWORK of ASHLEY -----

I've made two illustrations of what Ashley might look like in this story. To have them as "visual aids" just click on my user name and go under my list of artwork. They're called "Ashley's Initiation at the Pool" and "Ashley's Initiation at the Pool 2".

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Ashley is 19 years old and she's completed her first year of college. It's now in the month of July and she's enjoying her summer break.

She really likes college, however at times in her first year she had felt lonely and found it difficult to meet new people. She has always considered herself somewhat shy, so this doesn't help. So this Fall when she goes back to college she plans on getting into a sorority. She thinks by doing this it will help her open up more and become more outgoing. She hopes she'll get to make some new friends and possibly meet some hot guys, too.

A few months ago at college she met Maddison and now the two of them are good friends. Maddison is very attractive, just like Ashley, and she's also a member of the sorority which happens to have the most popular and attractive girls in the college. During her first year at college Ashley focused so much on studying and getting good grades that she thinks she missed out on some of her college life and experience. She doesn't want to be too shy and not allow herself to be open to try some new things. Maddison has told Ashley about a few of the exciting things she's done in the sorority and the awesome parties she's been to. Ashley decided to ask Maddison how she can get involved in the sorority and Maddison has said she'd be happy to help her with it.

Over the last few weeks it's been hot outside. This afternoon Ashley has been laying out in her bikini on her parent's deck, and over the summer she's been developing a nice tan. She decides to text Maddison to see if she's found out anything about how to get into the sorority this Fall.

After a few minutes she gets a reply. Maddison says she'll contact Jessica, who's in charge of the initiation process, and get back to her when she hears something.

About an hour later Ashley gets a text message back from Maddison. She says Jessica has some ideas for an "initiation process" which will help her to open up and be more outgoing, and get into the sorority. Jessica thinks they should get together at a pool, and she can even drive over and pick Ashley up. Maddison texts Ashley that she needs to wear her swimming suit and look her best. They can pick her up at 9am tomorrow morning.

Ashley's excited. She sends a message back that she's available tomorrow morning and she's really looking forward to it.

The next morning Ashley gets up early to get herself ready. She showers and shaves her legs, including her bikini area, so it's all nice and smooth like she always does. She wraps a towel around herself in the bathroom and combs her long hair while looking in the mirror. Next she brushes her teeth and pops in her birth control pill, which she's been taking to help keep her monthly cycle more regular and reduce pain. Even though she's just going to a pool she decides to put on some makeup and lipstick to look good for the girls. After this she picks out a hair band to put her hair up, thinking it will be cooler this way outside in the summer heat.

With her hair up now and out of the way, Ashley leans over the sink and puts in her diamond earrings. She looks at herself in the mirror and then remembers her favorite necklace. She goes over and opens up her jewelry box and gets it out. It's a heart-shaped necklace that her parents gave her for Christmas last year. She looks in the mirror as she puts it on.

Ashley walks back into her bedroom to get dressed. She shuts her bedroom door and locks it so her two younger teenage brothers, who are still sleeping, won't walk in on her while she's getting dressed.

Ashley goes through her dresser where her swimming suits are and picks out her purple two piece string bikini. She thinks this one looks really sexy on her. She takes off her towel and sets it on her bed and starts to put it on. She puts on the bottom art, taking the time to tie the strings on her right hip and then the left, and then she checks herself out in the mirror. She sees her tanned body in the mirror and her bare breasts are really noticeable since they are much lighter now than the rest of her body because of her time spent tanning. She turns around and she likes how her swimsuit shows off her perfectly shaped ass.

Ashley picks up her bikini top and adjusts it into place in front of her. She reaches around behind to fasten it. After this she moves back to the mirror and looks at her breasts in the swimming suit top, adjusting the fabric around them and turning to each side to make sure they look good.

Glancing over at her alarm clock Ashley realizes the girls should be here soon. She quickly slips into some sandals, grabs a towel, and heads on down the stairs to the kitchen. She wants to just quickly grab something to eat. But before this she walks over and checks her cell phone and she notices she has a text message from Maddison saying they're on their way and should arrive in about 20 minutes.

Around 9:00 in the morning a car pulls up into the driveway. Ashley looks out and sees Maddison in the front seat and it looks like Jessica is driving.

"Mom, they're here," Ashley calls out to her mom upstairs. "I'm taking off. Bye mom, I love you," she says.

"Okay," her mom responds from upstairs. "I love you too, honey. Be safe," she says.

Ashley anxiously walks out the front door of her parent's house and then on out to the car. She looks around and notices it's a beautiful day out today,

and perfect for a swim. She opens the car door and gets into the backseat.

"Hi guys," Ashley says.

"Hey Ash," they respond. Caitlin, another girl in the sorority that Ashley has seen before, is in the back seat with her.

"It looks like a great day to go to the pool," Ashley says, setting her towel and water bottle beside her. She didn't bother to bring her cell phone today, but she usually does.

"Yes, oh I know," Jessica says as they pull out. "It will be great to soak up some rays."

They drive for about 10 minutes and are almost halfway to the neighborhood pool they are going to swim at. Ashley is wondering what Jessica has in mind as far as an "initiation" into the sorority. She's heard some stories that sometimes these initiation processes can get pretty wild and crazy.

"So, I'm really wanting to get into the sorority with you guys this Fall," Ashley says. "Do you know what I'll have to do, as far as an initiation, to get in?"

Jessica looks back at her in the mirror.

"Well, I have an idea on that," Jessica says. "Something you can do today in fact."

"Okay, great!" Ashley responds. "So... What do you have in mind?"

Jessica pauses and smiles for a moment. "We can tell you when we get there," she says.

Ashley is a little irritated with Jessica's response. And it's making her start to feel a little nervous inside not knowing what to expect. "What does she want me to do?" she wonders to herself. "We're just going to a pool. Why can't she just tell me right now?" she wonders.

After a few more minutes of chatting on other things, Ashley asks Jessica again. "Come on, please tell me what's going on?" she asks. "What am I going to have to do?"

"Okay, okay, I'll tell you," Jessica says, a little frustrated with her now. "So this pool we're going to, the lifeguard there just happens to be my older brother's best friend. His name is Kyle, and he's absolutely fucking hot," she says.

Ashley's pulse quickens hearing this. "Oh... Okay?" Ashley says, not sure where this is going.

"So at this time in the morning it should be just him... and us," Jessica says. "So we'll arrange it so you and him can ... well... have some time to enjoy each other."

"What?," Ashley says in desperation and shock. "I can't do that! I... I don't even know this guy! This is... this is crazy!"

"You'll do fine," Jessica says, trying to reassure her. "Don't be so shy and afraid to try something new. This will be a good way for you to open up. You just do a good job and make him really happy, and you're in," she says.

Ashley can feel her heart pounding in her chest. Make him "really happy"? Ashley wonders to herself what Jessica means when she said that.

"So, are you on the pill?" Jessica asks.

Ashley is shocked by the question. "Um... yeah," she responds timidly.

"And you remembered to take it this morning?" Jessica asks.

Ashley is feeling even more uneasy now and doesn't like giving out her personal information. "Uh... yeah," she answers quietly.

"Good to know," Jessica says.

Ashley looks out the car window and feels very nervous now, and trapped. Based on Jessica's questioning, Ashley's now thinking she's wanting her to have sex with this guy at the pool. "Am I really going to do this?" she thinks to herself. However, she remembers how she's determined to be more open to new things and become more outgoing. She wants to show the other girls in the sorority she can handle any "initiation" process. She really wants to get into the sorority this Fall, but she wasn't planning on allowing herself to get fucked by a complete stranger to do it.

On that note, Ashley doesn't know it but that Jessica has gone to this pool quite often so far this summer to see Kyle. The two of them have had sex in the men's restroom before the pool opens on almost a regular basis. In fact, just yesterday Jessica went to the pool in the morning to see Kyle just like she is now. After passionately sucking his dick she bent over at the sink and had Kyle fuck her from behind.

As they continue driving to the pool the initial shock of what Jessica has planned sinks in for Ashley. She wonders to herself how this will happen, and what she will be expected to do, or perform? As she thinks about it she realizes her nipples are now stiff and pushing into her swimming suit top. She glances down and can see they are really noticeable, so she quickly grabs her towel and holds it in front of herself.

Ashley begins to think back on the sexual experiences of her past. She's always been a little shy, so in her life she's only been intimate with two boyfriends, and that was back in high school. The first one was Josh. He was a complete jock, and jerk. He was always wanting to just get into her pants. She convinced her mom at 15 years old to get her on the pill, and then she ended up having sex with Josh many times. He would always cum so fast though so she usually would not reach an orgasm which would leave her feeling unfulfilled most of the time, but he didn't care. He also taught her how to do a blowjob, but being shy she drew the line on swallowing.

After they broke up Ashley felt like she moved way too fast with Josh so she wanted to take it much slower with her next boyfriend. She went out with Nick through her junior and senior years in high school, but she told him no sex. Nick was okay with it because Ashley would suck his dick on a regular basis, but still no swallowing. He would go down on her to repay the favor and she got into thoroughly enjoying that. And she also got into giving him blowjobs as it really turned her on.

They broke up after they both went away to different colleges so she hasn't been intimate with any other guy since then. Quite a few guys showed interest in her during her first year at college but she just didn't have time for them. Studying and grades came first. Her parents stressed to her how important getting good grades in college is, especially in her first year. And with her being so attractive most of the guys just assumed she already had a boyfriend.

Ashley nervously looks out the car window. "I can't believe she wants me to do this," she thinks to herself. Her mind is frazzled at the moment. She hasn't had sex in over three years, and she hasn't given a blowjob in over a year, so the possibility of doing either one of these today leaves her feeling nervous and uneasy.

They pull into the pool parking lot and Ashley's heart is pounding. Kyle's car is the only one there. The pool doesn't open until 10:00 and they made it there by around 9:30. It won't open for another half hour but Jessica walks on up to the gate and calls out for Kyle. Kyle stops cleaning the pool and

walks up to the closed gate.

Kyle opens the gate and then Jessica smiles and waves back to the car. "Come on, he's going to let us all in," she says.

The girls walk up to the gate. Ashley follows them up walking on shaky legs. She's feeling so nervous and unsure right now. She has her

towel wrapped around herself and, even though it's already warm outside, she feels chilly because her heart is beating so fast.

Ashley looks ahead and checks out Kyle, and then she quickly looks away when they make eye contact. She notices he has the looks of a guy who could do ads for beachwear. He has a nice muscular build with tight abs. As he's talking to Jessica she sees he has a great tan and is really handsome. He has just graduated from college and is working at the pool for the summer, but he'll start graduate school at the same college the girls attend this Fall. "Oh my gosh", Ashley thinks to herself. "Am I gonna to have sex with this guy?"

"Hi there girls," Kyle says to the rest of the girls with his masculine voice and a big smile. He's holding the black iron gate open for them to come in.

"Hi, Kyle" Caitlin says smiling.

"Hey, Kyle" Maddison says smiling as she walks past him.

"Hi," Ashley says to Kyle quietly as she timidly walks past him.

"Kyle, this is Ashley", Jessica says to him.

"Oh, hi Ashley," Kyle says. "Nice meeting you," he says to her while taking in how attractive she is.

Ashley nervously smiles and breaks eye contact. "N... Nice meeting you, too," she says quietly and nervously walks into the pool area.

"She's kind of shy," Jessica says.

"Oh, no problem," Kyle responds. "You guys picked a great day for the pool. It's going to be just gorgeous out today," he says. He goes back to finish cleaning the pool and preparing for the day, occasionally stealing a glance over at Ashley in the process.

Ashley finds a lounger along the side of the pool and sits down. "What am I going to do?" she thinks to herself, almost in a panic. She bites her lip and looks away from the others. As she sits there she can tell her pussy is starting to get wet in anticipation for what Jessica has suggested will happen. However, she can't help but feeling unsure about this whole thing. "I should just leave right now", she thinks to herself. But she rode there in the car with the other girls so she can't just get up and leave, and she didn't bring her cell phone either.

Jessica goes up and starts talking to Kyle. After a moment he looks over at Ashley from across the pool.

Ashley sees him looking at her and her pulse quickens. She quickly averts her eyes, feeling very nervous. She can tell he's reacting to whatever Jessica is telling him, which is obviously about him and her getting it on some how. Right here. At the pool. Right now.

Ashley knows at this point she can't back out of it.

Maddison walks up to her. "Hey Ash, I'm really sorry about this," Maddison says. "Jess is the one who makes the decisions on these 'initiation' things, and I don't have any say in it. I didn't know this is what she had in mind until the car ride over here."

"I just can't believe she wants me to do this", Ashley says quietly.

Kyle walks with Jessica towards the men's restroom. Caitlin grabs a lounger from the pool area and starts sliding it over to the restroom. Ashley sees her doing this and she thinks she knows what they have in mind.

"Well, it will probably be quick," Maddison tells her. "And he's really hot, so it won't be all that bad," she adds.

"But am I really going to let this guy have sex with me? I don't even know him," she says quietly to Maddison. However, the thought of it is slowly turning her on. While she knows she should leave, a part of her wants to see what he's like.

Kyle holds the door open for Caitlin and she slides the lounger into the men's restroom.

Jessica walks on up and tells Ashley to come over.

Ashley's heart pounds as she gets up. She leaves her towel behind her, steps out of her sandals, and starts walking towards Kyle and the restrooms.

"I can't believe I'm actually doing this," Ashley whispers to herself. She looks down as she walks, feeling embarrassed. She can sense him watching her every move and this makes her even feel more nervous, but it's also turning her on at the same time. Her stiff nipples brush against the thin fabric of her swimsuit and she can feel some wetness between her thighs as she walks.

Jessica tells Caitlin to stand by the gate and watch to see if anyone is coming. "If anyone drives up, come over quick and tell us," she orders her.

"Okay, of course," Caitlin says.

Maddison walks into the restroom. Jessica and Kyle are standing next to each other. Jessica tells Ashley to go on inside.

Ashley hesitates to go in. She's never been in a men's restroom before. She gets up the courage to walk in.

Kyle watches Ashley as she walks past him, taking in her great hourglass shape. He then looks down and checks out her ass.

"What a great ass", he says while keeping his hands in front of himself to try to hide his growing erection.

"Yeah, she's not bad," Jessica says looking up at him, feeling a little jealous.

"Oh, I mean yours is great, too," Kyle says, and smiles. He reaches behind her and squeezes her ass in her swimsuit, causing her to jump a bit.

Jessica laughs and smiles back at him, giving him a wink. They both go on inside and the door shuts behind them.

Ashley can't help but feel embarrassed, and very trapped. The four of them are inside the restroom with the door closed. She looks down and sees the lounger out in the middle of the floor.

"So, we don't have much time," Jessica asserts. "Come on over here, Ash" she says.

Ashley slowly walks closer towards them, and then stops.

"Come on, he won't bite." Jessica says. "Get up here."

"Okay", Ashley responds quietly and walks up close to Kyle. Her heart is racing and she keeps eye contact with Jessica.

"Now undo his swim shorts and take out his cock," Jessica says.

Ashley clasps her hands together and her mouth drops open. "I... I don't...", she says and then looks down at the large bulge in the front of his swim trunks.

"No no. Just do it!" Jessica tells her.

"Okay", Ashley quietly responds and timidly reaches out with trembling hands to undo his drawstrings. She can feel her heart pounding in her chest, and she

can't bring herself to look up at him while she's fumbling with his strings.

She works the tie undone and then pulls her hands away. She can't believe the size of the bulge in his swim shorts.

"Now reach in there and pull it out," Jessica says.

Ashley looks at Maddison and then back at Jessica. She takes in a breath and gently reaches into his shorts and then touches his cock. Feeling it with her

hand sends a wave of adrenaline through her. It's been over a year since she's touched a man's hard dick. She pulls it up and out of his swim shorts, and then her eyes open wider when she sees it.

Her heart is pounding as she feels his cock with her hands. It's warm, large, and very hard. Her hands are trembling a little, and cold because her heart is racing.

"Ah, you're hands are cold," Kyle says with a chuckle, reacting to her touch.

"I'm sorry," Ashley says bashfully while looking down. "I'm just really nervous."

Ashley holds his long shaft in her hands and can't believe how big it is. He's much bigger than anybody she's ever been with. As she looks down she can see herself visibly quivering. Jessica can see it, too.