Ashley's Initiation at the Pool

This is version 2.0 of the original story. 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 been 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. And she hopes she'll be able to make some new friends.

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. "I can't 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 little "initiation" process. She really wants to get into the sorority this Fall, however 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 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 many occasions. 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.

Jessica and Kyle had been going out for about six months and then they broke up about three months ago. Kyle is ready to move on, but Jessica keeps driving over to the pool to see him. Jessica knows they are not right for each other, but she doesn't have another boyfriend right now. So in the mean time she likes to keep going back to Kyle, and tease him, tempting him to give in to her desires. It's odd, almost like a "friends with benefits" situation she has going on. Kyle doesn't think it's right and he's really wanting to move on from her, but he finds it hard when she's coming on to him at the pool. She's also attractive, and she's very good at getting what she wants.

So when Jessica was thinking of some kind of an initiation, or challenge, for Ashley to get into the sorority, she thought of Kyle. Jessica likes to be in control. She found it very enticing, the idea of being able to make Ashley do exactly what she wants her to do with Kyle.

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 would happen, and what she would 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're really noticeable, so she quickly grabs her towel and holds it in front of herself.

Ashley begins to think back on some of her past sexual experiences. 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 and he was a complete jock. Ashley really felt like she was in love with him at the time. With her being somewhat shy and introverted she found she was attracted to how popular and aggressive he was. She convinced her mom at just 15 years old to get her on the pill, with Josh's encouragement, and they ended up having sex many times. But soon he ended up being a jerk to her and not treating her very well. He was always wanting to just get into her pants. When they had sex he would always cum so fast that 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 very heartbroken. She was disappointed their relationship did not work out, possibly since she had so many first experiences with Josh. He helped her to get out of her shell and she liked this. She felt more popular when they were dating because he was so popular in school. She felt like she was accepted now by all the "cool" and "popular" students in the school, and she liked this a lot. But once they broke up she withdrew back into the comfort and security of her shyness. Some of the people she thought where her friends now shunned her, and this hurt. She knew she moved way too fast with Josh, so she decided in her future relationships to take it much slower.

Ashley went out with Nick during her junior and senior years in high school. She really liked Nick and he treated her better than Josh, giving her more respect and appreciation. She told Nick she wanted to wait on sex and Nick was okay with that. Ashley would suck his dick on a regular basis, but she did not want to try swallowing. He would go down on her to repay the favor and she got into thoroughly enjoying that. And she also began to enjoy giving him blowjobs as she found it turned her on.

They broke up after they both went away to different colleges. More like they drifted a part. Ashley tried to keep in touch with him, however as time went by she would hear back from him less and less. This made her feel really sad. She had hopes at times in high school they maybe he was "the one", but as she went through her first year of college she soon realized it just wasn't going to happen.

Quite a few guys showed interest in her during her first year at college, but for most of the year she was not interested because she felt like she was still in love with Nick. And on top of that, studying and good grades came first. Her parents stressed to her how important getting good grades in college is, especially in her first year. So during the school year she focused solely on hitting the books and didn't have much of a social life as a result.

At this point though, Ashley feels like she's gotten over Nick. And with college being over for the summer Ashley would love the possibility of meeting a great guy. Someone nice and thoughtful. Someone she could see having a future with. Someone she could trust, that wouldn't end up just leaving and hurting her again. She doesn't want to get hurt again.

Ashley nervously looks out the car window. "I can't believe she wants me to do something like 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 something remotely close to either one of these right now leaves her feeling very 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 thinks of how crazy this whole thing is. "I need to 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 worries at this point she won't be able to 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 something like 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 wonders 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 I can't let this guy have, like... sex with me. I don't even know him," Ashley says quietly to Maddison.

Ashley knows she should get up and leave. She's decided in the past to not have sex again until she's in a committed relationship. However, right now she can't help but feeling herself getting turned on. She wants to leave but she realizes there is a part of her that 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.

"Okay...," Ashley says. She wrestles with what to do. She's always been shy, but this time... this time she wants to show herself and the girls she can overcome it.

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 some 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.