Wet and Wild with My Parents’ Friend

The summer after my senior year of college was more than anything I could’ve expected or asked for. Unlike other prior-students, I wasn’t going straight into a job or traveling the world on some exciting exploration. I was just going to stay home, comfortably, until I figured out what it was, I really wanted to do with the rest of my life. And of course, according to plan, I ended up in the suburbs of the San Fernando Valley with no plan. 

After waking up at 11:00 am after a long, long night of jerking off to whatever it was I could find on the internet (girl on girl porn most of the time), I’d lounge on the couch and watch Netflix all day. That was, until my parents suggested it wasn’t the healthiest lifestyle. Instead, they suggested at the very least that I go out and find a job, or if not, do chores around the house for them. The latter seemed like the most efficient option for me; I got to make money while in the comfort of my home.

That’s not to say that I’m a lazy guy, though. I work out five days a week, eat healthily, and have a nice, lean body with a pretty visible six-pack. It’s just that I’m more laid back about life than eager to get out there and prove myself to someone, something, or the world. I’m often characterized as “cute” too, although my mind often wanders to dark and sexual places. Women I’ve been with sexually have always been surprised by my duality in being cute and innocent, but very horny and sexually dominating when the right time comes.

There was this side of me that my parents didn’t know about. Nor did their friends that would come over to lay by the pool with them as I cleaned it. For the entire summer, I ended up cleaning the pool daily while their friend, Alyssa, a 35-year-old divorcee, would lay by the pool. Alyssa was just freshly divorced to a wealthy investment banker and was now living off of the money from her settlement – she’d never have to work another day in her life. And God, she was beautiful.

Alyssa had the body of an 18-year-old with skinny legs, a tight ass, and perky breasts that would jiggle when she walked. She had one of the best bodies that I had ever seen, a body that any guy or girl could definitely appreciate. Her naturally light blonde hair fell down to her shoulders and her perfectly symmetrical bangs covered her forehead. Imagine a Margot Robbie look-a-like. Alyssa was more attractive than any girl in the neighborhood and she knew it well. 

It’s not even to say that Alyssa had all of these positive physical qualities but was unintelligent or insensitive. Alyssa actually had it all. She was more well-read than anyone I knew, generally smart, nice, easy to get along with, and a truly great listener. She was the full package and her ex-husband was the dumbest man on earth to go ahead and cheat on her. She really was a catch, and I had always fantasized myself with her. 

I was always sexually attracted to Alyssa but never had the opportunity to spend much time around her. For sure, she’d come to holiday parties and spend time with the family at the occasional small gathering but seeing her every single day (especially in a bikini) was a new, exciting, experience for me. But at the end of the day, she only knew me as my parents’ son; I was just a kid to her, nothing more. If only she knew how badly I wanted her, how badly I wanted for her to show me her sexual prowess. I could only imagine the things she’d be able to show me.

Now, instead of my plan for this summer being to do nothing, I decided to spend as much time around Alyssa. My plan wasn’t that clear-cut, but I was hoping that she’d eventually catch on to my sexual attraction and be interested. I was older now and since I’d worked on my body, I thought that it would be possible she wouldn’t view me as a kid anymore. Essentially, I just wanted her to notice me. This was a pipe dream at first, but at least it got me out of bed, motivated, and making money during the summer. After I decided to pursue this, I even started watching less porn (now only four days a week). 

Each time I would be in the backyard with her, cleaning away at the leaves in the pool, I wasn’t able to control myself. I’d feel the blood rush to my cock and would get aroused beyond belief. Images of us passionately kissing and taking in each other’s bodies flooded my mind. I couldn’t erase them, nor did I want to. It came to a point where I was going out there to clean the pool when there was nothing to even clean, just so I could see Alyssa’s bikini fit snugly around her smooth, soft skin. At the time I thought she was way too much for me to handle. It’s not like I hadn’t been with women before… I had just never been with anyone like her. 

Day after day I’d go out there, say hello to her, and then clean the pool. While I’d clean, I would look over at her with complete and utter desire. I wanted to taste every piece of her. She’d sit there, lounging around reading her book – if I recall correctly, she was busy reading “Civilization and its Discontents”. Even with her sunglasses on, I could get the sense that she might not even be reading. I’d fool myself to think that she was actually looking at me, longing for my flesh. Longing for me, a strong young man, to ravish her body and make her feel young again. Whether it was true or not, I acted accordingly. And on one particular day, I got a deeper sense of her interest, to say the least. 

It was a Wednesday and I woke up bright and early at 7:00 AM to make breakfast for my parents and get them out of the house quickly before work. They both had to go to meetings that would run late into the day. By 7:45 AM they were both on their way out the door. 

“Alyssa is coming around 10 to lay by the pool. You know, if she needs anything just please help her. She’s going through a tough time with the divorce and everything,” my mom said before leaving. 

“Of course. She’s like family at this point,” I tried to play it off casually.

After finishing up some cereal I decided to clean my room and go to the supermarket. Once I got to the supermarket, I bought some pineapples, oranges, coconut water, and rum. I’d seen Alyssa drinking piña coladas at a holiday party the year prior and thought it would be a good way to play into her taste. I wasn’t quite sure how to make a piña colada, but this is what my mind told me was right. After getting back home around 9:30 AM I changed into my bathing suit (with no underwear) and sat in the kitchen nervously awaiting Alyssa.

9:30 passed. Then 9:35. I was wondering if Alyssa was even going to show up today. Maybe she decided to change her plans for the day? Finally, around 9:45 AM Alyssa rang the front door. I popped out of my seat and quietly dropped to the floor. As fast and as discreetly as possible I banged out 10 push ups and then stood up. I wanted to look appealing to her. I wanted her to notice the veins on my arms and wonder where else she’d be able to find large veins on my body. After adjusting my tank-top, and I took a deep breath and walked to the door. I opened it up.

“Hey, good morning,” I said casually.

“Morning, Chan,” she said, standing there in her blue and white striped flannel and white, cropped jeans. 

“I haven’t cleaned the leaves out of the pool yet, but I’ll do it right away, sorry,” I said timidly.

As Alyssa walked to the back of the house and put her purse down on the kitchen table, I couldn’t stop thinking to myself how stupid I was for saying that. It sounded so childish and weak. She was looking for a strong man and I knew that I had to turn things around and speak with confidence. 

“Oh no! Don’t worry about it, babe. I’ll be laying out for a bit anyways – no rush!” Alyssa smiled at me and continued through the screen door to the backyard.

Although she was older than me and mature, she was so adorable and courteous. That just made me want to feel her body up against mine even more. The sweeter she got, the harder and sexier I felt. Now I was already beginning to get hard as I felt my cock slide out-of-place to the side. Before going out to the backyard I adjusted it in my pants and put it back down. I didn’t want to scare Alyssa away or have her see the outline of it quite yet.

As I stepped outside into the blazing July sun, I could see Alyssa by the lounge chairs across the way taking off her clothes and revealing a cute, little red bikini. The bikini top could barely contain her D-cup breasts and the bottoms were riding up her tight butt. I couldn’t help but stare at her while she wasn’t looking. Though, I quickly felt weak in the knees and decided to focus my attention on cleaning the pool. Now was still not the time.

After about 30 minutes of cleaning leaves from the pool, I was dripping in sweat. I decided to take off my tank-top. Not just because of the heat, but to show off the summer body that I worked so hard on for Alyssa. I threw the shirt onto the lounge chair next to Alyssa as she laid down in silence. She had her eyes closed and her hands crossed on her chest. Now I was pretty sure she was sleeping. This was a great opportunity to make first contact. I was nervous, but I went for it.

Softly, I placed my hand on Alyssa’s shoulder. Her skin was soft. I didn’t want to let go. But I tried my best to gently wake her up. “Hey, Alyssa. Do you want anything to drink?” I whispered to her. Alyssa calmly adjusted her positioning on the lounging chair and took her glasses off. Her beautiful sea blue eyes glistened in the sunlight. 

“Hmm…” she looked at me, contemplative. She brought her knees up to her chest and hugged her legs. She started to lick her lips. I couldn’t control myself and could feel my cock stiffen as she’d continue to lick. Was she licking her lips for the drink or because of me? Whatever the case, I couldn’t help but imagine her tongue licking a trail down from the head of my cock to the shaft, then around my groin. The warm, wet pleasure. 

I had to say something to break the tension. Smoothly, I said, “we have some pineapples and stuff for piña coladas if you want me to whip one up for you.” Hopefully, that was smooth and didn’t seem premeditated.

Thankfully, her eyes lit up. “That would be lovely. Let’s see if you learned a thing or two in college, stud.” She was teasing me, and I couldn’t get enough of it. Whether it was her flirting or not, it made me feel tingly inside. 

Things started out smoothly as I smiled at her, nodded, and walked over to the kitchen. Stupidly, I didn’t even realize that I had left all the piña colada ingredients out on the counter in the plastic bags. Maybe she saw? Maybe she knew what I was doing? I felt dumb for making that mistake, but I started to cut up the pineapple and make the piña colada. It didn’t take long for me to find out that I didn’t exactly know what I was doing. Things got a little rocky.

Now, I’m not much of a drinker and was never really the partying type in college. Whenever I drank, someone else mixed it for me or I paid at a bar. Truthfully, I didn’t quite know what a shot was. I just didn’t want her to see me as a child who couldn’t make a simple drink. In order to make sure that her drink wasn’t too light, I put more-than-healthy servings of rum into the blender. I thought it might’ve been a little too much alcohol, but we were about to find out for certain.

Within 10 minutes I whipped up the colada and brought a cold glass out to her and one for myself on a tray. She watched me walk over and I could notice her looking down at my bulge quickly before averting her eyes back to the coladas. Her eyes lit up once again.  Once in front of her, I bent down and handed her the colada.

“Let’s see what you got,” she said as she wrapped her lips around the plastic straw and sucked. She swallowed and then giggled.

“Wow. You like it strong, huh?” She didn’t take her eyes off me for a second and continued to suck the straw. 

“Yeah, this is how we used to make them back at school,” I tried to play it off smoothly.

It got tense for a moment. I was almost certain she was going to call me out for my bullshit. “I like it,” she said, to my surprise. 

“Why don’t you stop working for a bit and just sit and drink with me?” Alyssa said with her seductive smile. “I won’t tell your parents,” she winked. 

I got nervous and swallowed. “Sure. Yeah, of course. I’m not worried,” I chuckled uncomfortably. I started to get a sense of where things were headed. I had planned this and there was no backing out now. I put the tray down on the table, grabbed my drink, pulled the umbrella closer to us so that we were in the shad, and sat down next to her.

There I was, as close as I could’ve wished to be to Alyssa, but, with a heavy piña colada in my hands. I shyly sipped on it as we both sat there in silence. Maybe the alcohol would help me let loose and release my inhibitions. I tried to play it cool and finished the drink over the course of 30 minutes. It was the strongest drink I’d ever tasted, but I couldn’t seem weak in front of such a powerful woman who was downing it like water. She could handle herself, and sure as hell handled her liquor.

As we sat, we spoke about my recent graduation, reminisced on old holiday parties we’d both been to, and she dug deeper into why her marriage didn’t work out so well. She was such a sweetheart and didn’t deserve for her husband to cheat on her. He must’ve been out of his mind for deciding to make a decision like that too. As much as I had sexualized Alyssa in my mind, she was very easy to get along with and as well-spoken as I had always imagined her to be. Ironically, in turn, this ended up making me even more sexually attracted to her. Throughout the conversation, I had to fidget in the chair to not show that I was being turned on by her charm and wit. 

Alyssa looked down at my bathing suit as I fidgeted, trying to hide my erection. She clearly noticed what was happening but didn’t bring any more attention to it. Instead, as the conversation came to a close, Alyssa put her glass down on the table and decided to step into the pool.

“I’m going to take a quick dip,” she said with a suggestive smile. 

As I watched her walk away, her firm, tight butt jiggled in her bikini and she had a strut in her step. With each step and jiggle I felt more erect. Juices started to leak from my cock – I knew that wouldn’t be able to keep this up much longer – I may very well just cum in my bathing suit. Alyssa gracefully walked down the steps into the pool and the water reached her breasts. At that moment, I remembered that we kept the pool water cool. Within an instant, Alyssa’s nipples hardened, and I could see them through her bikini. They were large – I wanted to suck and lick them like a madman. 

Alyssa looked down and noticed how visible they were. She didn’t even try to hide it and giggled. Then, she looked over to me, “are you coming in?” Alyssa possessed me with seductive eyes. 

I knew how important this question was – it wasn’t even so much of a question as it was a test. If I stepped into that pool, I’d get exactly what I wanted. Now, the nerves were beginning to hit me, but I decided to embrace them and the adventure. “Sure,” I said. 

She kept her eyes on my cock as I got up and walked over to the edge of the pool. Since I wasn’t wearing any underwear in such a small bathing suit, it was very easy to see my cock jiggle and to see a very visible outline of it. I sat down at the edge of the pool with my feet in the water. Alyssa was in the pool directly across from me. After a few seconds of me sitting and contemplating my next move, she started to slowly make her way toward me like a seductive siren. The water parted ways for her, and I started to get a bit more nervous for what was about to come.

It was straight out of a movie how the rest of the morning played out in the backyard. Alyssa finally within inches of me and stayed in the water. She looked up at me and our eyes met. I felt her pierce through my confidence, “Are you not coming in?” she asked while placing her smooth hand on my leg.

“I’ll… uh, come in really soon.” I said stupidly.

“The sun must be hurting your back. The water’s cold and it’ll be fun. I promise I don’t bite,” she said suggestively. She started to gently pull me in toward her. 

As my legs fell deeper into the water, I felt a chill hit my body and it startled my throbbing cock. Our almost naked bodies were practically touching, all I had to do was make the first move – but I waited to be safe. At the same time, I wasn’t too worried because large hedges surrounded the backyard. The neighbors wouldn’t be able to see or hear anything. Alyssa was way more experienced, so I figured if she wanted to do something, she’d have no reservations. She pulled me deeper into the middle of the pool. 

“I see the way you look at me all the time,” she said.

“Huh?” I played dumb. We now reached the center of the pool and stopped.

“The way you look at me with those sex eyes,” she said, “I’ve noticed.”

“I mean, you’re incredibly attractive,” Now, I tried to play it off cool.

She came in closer to me and put her wet mouth near my ear. I could feel her lips graze my skin and I felt strong pulsating from my pants. She wrapped her arm over my shoulder and attached herself to my body sensually. Her skin smelt like vanilla and her breath smelt like sweetness. I couldn’t believe that this was actually happening now.

“Your muscles feel so nice. You’re a grown man now and it’s been making me so wet. I’m even wet right now, baby,” she whispered ironically.

Without any warning, she kissed me on the cheek, and then grabbed my face with her soft hands and kissed me hard on the cheeks as if she was longing for my taste forever. In reality, I was the one longing for her taste. I tasted the pineapple and rum off of her breath. Although at first, I was taken aback by it all, I decided to embrace it and initiated the next kiss.

I stopped for a moment, “I don’t think my parents will find out.”

“I’m not worried about that at all, sweetie. You’re a big boy,” she said as she looked down at my crotch, “you can keep a secret.”

Then, she wrapped her right leg around mine and dry-humped me as she slid her hand down my abs, to my groin, to my cock. She gripped it tightly, squeezed it even harder, and then giggled. 

“Fuck… it’s such a strong, hard cock,” she whispered with heavier breaths.

“I’ve wanted to fuck you with it for a while now,” I said with confidence.

I was starting to feel more comfortable with the situation now. It was already happening so there was no backing out. I knew that soon enough my cock would be deep inside her warm, wet pussy, and it would be the greatest feeling in the world. For now, we continued to kiss each other, our lips locked and our tongues meeting in the middle and sliding down each other’s throat.

She was the best kisser I’ve ever been with. She was so experienced, and I liked how dominant she was being with her tongue. It was like her tongue was an extension of her mind and knew exactly what it wanted. I admired that confidence and found it overwhelmingly sexy. Without realizing, our bodies drifted to the edge of the pool. I felt my back hit against the cement and Alyssa leaned over on me.

As I leaned against the edge of the pool we continued to kiss – our hands passionately grabbing each other’s face and hair. She was manic for my body; she couldn’t resist it and I was happy to know that she felt the same way – she’d just been waiting for me to make a move and clearly couldn’t wait any longer. Her body wrapped around mine… we were now one.

I couldn’t tell if I was getting sweaty – from our making out or the sun – despite the chill from the pool. Our wet bodies rubbed against each other and I grabbed her butt with both of my hands to pull her in closer. Her ass was as firm as it looked, and I squeezed it even harder. I liked that she worked hard for that body, and she knew I liked it too. Just as aggressively as I grabbed her ass, she grabbed my cock once again. She had a firm grip on it and it almost seemed like she was going to rip it off. In a weird way, I liked this a lot.

Then as things picked up, I turned her around and leaned her up against the edge of the pool. She arched her back and small waves formed around us. I started to lose control too and the aggression was at an all-time high. I could tell that she wanted it, otherwise, I would’ve been gentle with her. I ran my fingers through her wet blonde hair and pulled it back. As I did, she bit her lip. Then, I reached behind her and unstrung her bikini top. Her D-cup breasts popped out. She had beautifully symmetrical and large nipples, and I wanted to taste them so badly.

I started to slow down the tempo and lick around her breasts in a circular pattern, I wanted to taste all of her skin. I cupped her breast in my hand and licked closer and closer into the center till I finally hit her nipple. Her nipple hardened as I licked, and I started to rub it too. She couldn’t contain herself and started scratching my back, leaving what felt like cuts – but I still didn’t mind the aggression. From one breast I licked a trail all the way over to the other. The waves started to intensify, and she completely wrapped her legs around me. Her legs held onto me tightly – she was strong. 

Alyssa brought herself close to my ear. I couldn’t believe my ears. “I want you to fuck me with that long, hard cock of yours, sweetie,” she said. 

Then, she put her hands on mine and guided them down to my bathing suit. Slowly, but surely, she pulled off my bathing suit and my cock stayed hard in the water. Alyssa started to breathe heavier and didn’t take her eyes off of it. She guided my hand to my cock and started to stroke it with me – her hand over mine. She started slowly and with a tight grip. I wanted to cum so badly but saved it for later. After around a minute, she guided my hands to her bikini bottom and slid it off. 

Her pussy was completely shaved and beautiful. I wanted to feel all of it and be completely inside of her. Then, she took my hand and put it back onto my cock, bringing it closer and closer to her already wet pussy. Immediately, she slid my cock inside of her. From the tip, to the shaft, to the base. She took it all with ease. I was amazed at how experienced and comfortable she was – and how comfortable this made me feel.

She wrapped her arms around my shoulders and looked me dead in the eyes as I thrust into her. I didn’t even have to start slow, she told me to go fast and hard right away. She wanted it rough… and I was going to give it to her that way. I thrusted hard, in and out, back and forth. She took all of my cock in doses like it was a drug that she couldn’t get enough of. Alyssa didn’t even try to hold anything in – she was moaning as loud as she could. At this point, I had completely forgotten about the neighbors, my only focus was on her.

Alyssa gripped onto my shoulders tightly. “Just pull out before you cum, baby. I don’t mind,” she said.

Following her instructions, just as I was about to cum (which took no more than 5-7 minutes) I pulled out and came into the water. Alyssa started giggling, cupped it up from the water, and ate my cum. I’d never seen something that daring and sexy. She was a catch. 

Then, I told Alyssa I could keep going, but she told me it was alright. She said she wouldn’t be able to cum, and no one (not even her ex-husband) made her cum in over 10 years. I felt bad about this and told her that the next time we would get together I’d make it my mission to get her to cum.

I saw Alyssa several more times throughout the summer, and only during very few times that my parents were out-of-town. Despite being against all odds, I did get her to cum on the third time we slept together. She squirted everywhere, and I felt so good that I was able to do that for her. Now it’s been a while since we have seen each other – though we still talk from time to time. 

As weird as it may sound, our relationship didn’t change or become strange, we managed to keep things healthy and open with one another. On the surface, we’re just family friends, but in the depths beneath it all, we’ll always share our little secret.