Pool Boy Chronicles

As I have shared in previous accounts of my past summer doing pool maintenance services, I have experienced some unexpected and unbelievable erotic encounters. I had one experience that was quite different from the others, and I know it will the one that will remain in my mind the longest. It happened at a beautiful home on Cardinal Drive, not the largest by any means in a neighborhood of magnificent estates, but a large well-maintained mansion in a somewhat secluded location. The pool at the home was always one of the easier ones to clean and maintain, and I was usually in and out in about a half hour. Typically, the only time I saw a person there was when the owner came out and gave me my check. She was a kind woman and always thanked me for my good work.

So, it surprised me one week when the owner’s daughter came out of the house to deliver my check. I had not seen her before. In fact, I was not even aware that the owners had any children. She looked to be my age. She was dressed simply and comfortably in a pair of athletic shorts, a pink T-shirt, and flip-flops.

“My Mom asked me to give you this check,” she said as she looked down at the paper she was holding. “She and my Dad are out of town for the rest of the week. I take it that you are Chris?”

“Thanks,” I replied. “I didn’t know that your folks had any children since I seldom see anyone back here while I am working. What’s your name?”

“Ashley.”

“Well, I am pleased to meet you Ashley. You are very beautiful. Seems like I would have seen you laying out in the sun at some point this summer since you are so nice and tan.”

“I’m pretty modest,” Ashley replied. “I usually never go out by the pool unless I’m sure I will be alone.”

“I am guessing that means you sunbathe in the nude to get that nice even tan,” I said with a smile. “That would make sense in a nice private back yard like this one.”

“I would never dream of doing something like that,” Ashley replied with wide eyes. “I would be mortified if someone came back here and caught me naked. Besides you, we do have other workers back here sometimes.”

“Are you usually home when I show up here every week? It would have been nice to have you come out and talk to me while I worked.”

“I have often watched you from my bedroom window upstairs,” she answered while directing her eyes to a window facing the pool area. “My Mom is always talking about what a nice boy you are and how dependable you are. I would always watch for you because I think you are very cute and very athletic.”

“Then you should have come out and introduced yourself weeks ago,” I said. “It makes the job so much more enjoyable when I have a cute girl like you to talk to.”

“Like I said, I am pretty shy and modest. I was afraid I would not be able to think of something cool to say.”

“How old are you?” I asked cautiously, not wanting to make her nervous.

“19. I will be a freshman at the local university this fall.”

“Cool,” I replied. “I’ll be a junior there this fall, though I still haven’t settled on a major. That’s why I am doing jobs like this in the summer.”

Ashley was a very sweet young girl, and I enjoyed talking to her as I admired her attractive figure and expressive face. We talked about the university campus, and she had a million questions about where certain dormitories were located and how the food service worked. I was dying to get her phone number so I could ask her out on a date, but it didn’t seem appropriate for the daughter of one of best clients. As it turned out, Ashley was the one who broke the ice.

“This is so awkward for me to say,” she began. “The main reason I came out was to see if you would be interested in coming back after work and have dinner with me here on the patio? As I said, my parents are out of town for a few days, and it would be nice to have some company here.”

“I would like that,” I said with a big smile. “Can I bring something?”

“I was thinking take out since I don’t have much experience as a cook. Chinese, maybe? Pizza? Pad Thai?”

We settled on Chinese takeout, and I told her that I would be back by about 5:00 that evening. I am used to eating alone most nights in my small apartment, and I was excited by the prospect of a nice dinner with a beautiful girl. After I finished my last pool job for the day, I went home, showered, and put on some fresh clothes. I got back to her house just as the restaurant delivery guy was leaving, so the timing was perfect.

Just like in the movies, we ate our Chinese entrees right out of the white cardboard containers. Ashley and I talked some more about college and favorite rock groups, but I could tell that there was something more on her mind. I did not want to be too direct or sound too inquisitive, so I let it rest. I figured that if there was something she wanted to say, it would come out eventually. We took glasses of lemonade down to the pool after dinner to relax and enjoy the summer evening. Then, out of nowhere, Ashley turned to me and spoke in a nervous voice.

“This is hard for me to say, but there is something more I wanted to ask. Actually, the main reason I invited you back this evening.”

“What do you want to ask?” I replied as I sipped my lemonade.

“It’s not so much a question as a confession,” she said. “I mentioned that I have been watching you from my bedroom window all summer. I think you are very cute, and ever since I first saw you, I have been wondering if you could help me with a big problem.”

“If it deals with something I can help you with, I’m willing to help. What’s the issue.”

“I’ve never been with a boy before,” Ashley said with tears welling up in her eyes. “You know, in a romantic or intimate way. My parents are so strict that I never really felt like I had a real opportunity to do things like other girls.”

“That is hard for me to picture,” I replied. “You are so beautiful. I would have guessed that you would have a long line of guys wanting to go out with you.”

“There was one guy in high school that I thought I liked, but it turned out to be horrible. We were in his house when no one else was there and he started taking off my clothes. The lights were out and I tried hard to get him to stop, but he managed to pull my shorts and panties off and put his stiff penis between my legs. I was crying the whole time and begging him to stop, but he just kept pressing deeper into me until I felt him ejaculate. The whole thing only took a few minutes, but it was the worst thing that I had ever experienced. As soon as he fell off me, I pulled on my clothes and ran out of the house. He took my virginity, but even worse, he robbed me of my confidence. That was nearly three years ago, but I have lived with the guilt and the feeling that I might never be intimate with a boy again.”

Ashley was sobbing now, and so I moved closer and gave her a powerful hug. She had probably been trying to say this to someone for years, and once she had a chance to spill out her pent-up emotions, I got the feeling that this was a moment of therapy for her. I held her close for several minutes without talking and kissed her gently on her cheek to let her know that I would do my best to try to comfort her in any way I could.

“Not all guys are like that selfish asshole,” I said quietly. “You’re too nice a girl to let one horrible experience ruin everything for the rest of your life. Is there a way that I can help?”

“I know there are a lot of good guys that treat girls better,” Ashley said as she wiped away some tears. “I think you are a nice guy.”

“I’d like to think I am a good person. I certainly would never treat you like that.”

“I’ll be living away from home at college in a few weeks, and I am still afraid that my memories of that night will keep haunting me. I am so worried that I may push all guys away before I even give them a chance to love me.”

“I think you will know the right guy when he comes along,” I said. “It may be hard at first, but you need to lower your defenses a little bit and let some people into your life.”

“I know, but all of the other girls my age are so much more experienced when it comes to guys and dating, and even sex if that ever becomes a possibility for me again. I am afraid that the college guys will be so disappointed when they discover how clueless I am.”

“You just have to give it some time,” I suggested. “It may be hard for you at first, but I am sure you will find your way. When that time comes, the guy you select will be one very lucky dude!”

“Will you be that guy?” Ashley asked nervously. “Okay, now it’s out. I wanted you to come back this evening because I have been dreaming that you might be the guy who can help me to overcome my inhibitions and find out what real intimate pleasure is all about. I know we hardly know each other, but I have a feeling that you would treat me with respect. I think you can see that I am a good and decent person.”

At first I was unsure how to react. Ashley was beautiful, and I knew I would be a fool to pass up such an opportunity. But I was also thinking about the possibility that it might not go so well. She had already had a bad experience with a guy, and I wondered what would happen if she freaked out when I tried to get intimate with her. We both sat quietly for a few moments, and I think Ashley knew I was weighing my options.

“I know I am making a strange request,” she said, “but I am really serious. I have been wanting to say this to you since the first day I saw you working on our pool. Can we go inside and talk about it some more?”

“Okay,” I replied a bit nervously. “It is getting a little chilly out here on the patio.”

“Let’s go up to my bedroom so you can see the view I have of the pool in the back yard. It’s where I first saw you.”

Ashley’s bedroom was exactly like I pictured it would be. It was a spacious room decorated in pale pink and white colors, and the wall decorations reflected her interests in music and fine art. There was a large walk-in closet at one end of the room that featured a full-length mirror, and I could see a large shower through the open bathroom door at the other end of the room. Ashley and I stood in a comforting embrace near her bed.

“Are you sure that this is what you want?” I whispered in her ear. “Do you promise that you will tell me immediately if you ever get uncomfortable?”

“Ever since I first saw you out working on our pool, I have been very sure about this. I circled this weekend on my calendar the day I found out that my parents would be out of town. I have been waiting for a time when I had the house to myself.”

“Tell me again how you think that I can help you,” I said as I kissed her cheek.

“I want to find out what is feels like to be loved by a guy. I want to find out what boys like and what I need to do to make them feel special. I want to see if I have the courage to reveal my body to a boy. I’m 19 years old and no boy has ever seen me naked.”

“I think the biggest mistake that many girls make at the beginning of a relationship is the feeling that they must first please the guy to make him happy. Guys love being intimate and getting sexual satisfaction, but it’s not a one-way street. When I have been in a relationship with a girl, I always try to focus on her needs first. Would you like us to start that way?”

Ashley didn’t say a word but silently nodded as she looked up at me with innocent eyes. “That would be so much different than my first horrible experience.”

“I would like very much to see your beautiful body, Ashley,” I whispered. “Is it okay if I take off your clothes so that I can see you completely?”

Ashley collected her courage and nodded her consent. I began by massaging her back to relax her and then I lifted her T-shirt over her head. She was wearing a very pretty lacy bra, but it was sheer enough to give some suggestion of her beautiful breasts. I looked her in the eyes to see if I should continue, and she gently nodded. I reached back to unhook her bra and slowly removed it to reveal the most beautiful breasts I had ever seen. They were a bit larger than I expected, perfectly formed, and more pale than the tanned skin of her torso. I gently massaged both breasts as I kissed her passionately.

“You are incredible,” I whispered as I pressed her against my chest. “Are you still okay or do you want me to stop now?”

“I want you to keep going,” she said quietly. “This is just the way I imagined this moment.”

With that encouragement, I unsnapped her shorts and pulled them down her legs. She stepped out of them and kicked them aside. I reached behind her and slid my hands past the waistline of her panties so that I could feel the soft skin of her ass. Ashley seemed to like the sensation as I massaged each cheek. I could sense both uncertainty and anticipation as she stood before me wearing nothing but lacy panties.

“I have never seen a more beautiful body in my life,” I said quietly as I gazed at her. “It is hard to believe that you have not revealed yourself like this to any other boy. How does it make you feel to be nearly naked with me?”

“It feels embarrassing and exciting and surreal and unbelievable,” Ashley said with a bit more courage in her voice. “Do you think other boys will think I am beautiful too?”

I walked Ashley over to the full-length mirror on the door of her closet and stood behind her. “Do you ever really look at yourself in the mirror after a shower?” I asked. “I’ve known some girls who say they do not like the way they look without clothes, even though they are beautiful.”

“I guess I don’t,” she admitted.

“I think society and the media have caused many girls to feel discouraged about their looks for no reason.” I slid my hands around her torso, briefly cupped her breasts, and then guided them down her elegant feminine curves. “You are stunning in every sense of the word, and you should feel very confident in your beauty. When you get to the point where you feel fully comfortable in your own skin like you are doing here, I guarantee you will feel more confident when you begin to explore relationships with other guys.”

I could sense that Ashley was getting more nervous at the prospect of being totally revealed, and when I reached for the waistband of her underwear, she put her hands there first as if to say that she was not yet ready for that final step. I hugged her closely for several moments and then motioned for her to lie down on her bed. We pulled back the comforter and top sheet, and she quietly lay on the bed. I think she suspected that I would tear off my clothes and ravage her, but instead, I sat next to her and began to stroke her hair and face.

“Just relax and let me show you what intimate pleasure is like,” I said quietly. “Are you still comfortable with how things are going?”

“It actually feels very relaxing,” Ashley said with a comforting smile. “Aren’t you going to get undressed?”

“In a little bit,” I reassured her. “My whole focus in on you right now.”

I began a slow and sensual exploration of her body with my hands. She seemed to like it when I gently massaged her breasts and tickled her nipples with my fingertips. I continued down the length of her abdomen, emphasizing her lovely feminine curves along the way. I started to pull off her panties, and this time she did not resist my advances. A small tuft of fine hair came into view, and as I continued to pull her lacy garment down her legs, the soft folds of her labia were revealed. I slid her panties over her feet and placed them on the bed next to her body. Ashley was now completely naked.

When I began to move my fingers in slow circles around the cleft between her legs, she wriggled around a bit at the sensation that was obviously totally new to her. I probed deeper with one finger and got an immediate response.

“Your finger feels so good,” Ashley whispered with her eyes closed.

“Do you ever do this to yourself?” I asked.

“I guess I have tried a few times,” she replied, “but I always felt self-conscious about doing it.”

“No need to feel bad about making yourself feel good,” I whispered as I continued to pleasure her with my finger. “It should be as natural as breathing.”

“It feels so much better when you do it,” she said quietly.

I eased her legs apart slightly and positioned myself so that I could introduce Ashley to the pleasures of oral stimulation. I started by kissing her breasts and then worked my way down her torso until my lips were pressed against her pussy lips. She moaned softly as my tongue began to probe for her sensitive love bud. At the same time, she opened legs a bit wider to allow me to probe even deeper. She let out an even louder sigh when my tongue found her sensitive clit, and she began to move her body in rhythm with my oral advances. For several minutes, Ashley was moaning and twisting as her pleasure increased, and then finally she let out a loud moan as she climaxed. I continued to probe with my tongue until she squeezed her legs together to signal that she could take no more.

“Are you going to take off your clothes now?” Ashley asked. “I need to know how to give the same pleasure to a boy.”

“Let’s take a shower first,” I suggested. “Your shower looks big enough for both of us.”

“I think that would feel good,” Ashley replied. “Do I get to strip you like you did to me?”

“If you prefer. I am more than ready to press my skin against your body.”

Still naked, Ashley stood up, pulled my shirt over my head, and pressed her face against my bare chest. She stroked the muscles across my back and arms and the look of anticipation in her eyes suggested that she was anxious to see a boy completely revealed for the first time in her life. She unsnapped my shorts and dragged them quickly down my legs. As I stepped out of them, I noticed that Ashley was closely gazing at the bulge in my briefs.

“Go ahead and touch it if you want,” I urged. “Girls sometimes like to trace the shape through the fabric before they actually pull them down.”

“It looks bigger than I expected,” Ashley whispered as she began to stroke the bulging fabric. “Are all boys like this?”

“You’ll find out that cocks come in all sizes and shapes,” I said with a smile. “I may be a bit bigger than some, but they all work the same way. See for yourself.”

With that encouragement, she grabbed the waistband with both hands and slowly pulled down my briefs. She was hesitant to pull them over my cock that was now starting to come to life, but when she did, she let out a hushed exclamation when it flopped into view.

“It is much bigger than I imagined,” she said.

“I guarantee you that it will get even bigger the more you give it your full attention. Let’s get into the shower. You will have plenty of time to explore your new toy.”

The shower in the ensuite bathroom was one of those large walk-in showers with marble walls, a built-in bench, and an array of overhead shower heads. It was a perfect setting for two people who were exploring each other’s body for the first time. Since we were alone in the house, we were not rushed for time, and so we reveled in the warm water that was cascading down on us. My focus was on Ashley’s perfect tits, while she was fixated on my cock that was growing harder each time she stroked it with her soft, soapy hands. I knew that if she continued her marvelous hand job, I would shoot my load tight there in the shower, but since I wanted to save myself for later activities, I suggested that we get out of the shower and dry off.

“Why did you stop me?” Ashley asked as I dried her back. “It seemed like you were getting close to orgasm.”

“You are so right,” I replied, “and that is why I thought we should take a pause. There is more that I would like to show you, and I thought it would be better to do it in your bed.”

Once in her bed again, I lay on my back so that she could continue her study of the male anatomy. She brought her head close to my midsection and just gazed at my flaccid penis for a few moments, now just a few inches from her face. She began to trace her fingers lightly along my thighs and lower torso and giggled a little when my cock began to twitch slightly and begin to harden. She was fascinated by the folds of skin on my scrotum and stroked my balls carefully as my erection became more pronounced. When she turned her attention to the tip and shaft of my cock, my moans of pleasure convinced her that she was doing everything right. Within minutes, I was as hard and as aroused as I had ever been, and I would have been perfectly satisfied if her hand job had led to a happy ending.