Finally, something I can contribute to!

I used to work as an assistant caretaker for a wealthy family after I graduated high school. My daily activities ranged from gardening, keeping up the pool, maintaining running trails and mowing in the summer, to chopping wood for the fire place and keeping away the obscene amounts of leaves that accumulated in the winter. Whatever I was doing, it was usually focused around the house while the actual caretaker, an older guy who was good friends with the owner, spent almost all of his time directing landscapers he hired for the many plans they had for the 80 or more acres at their disposal. A zipline, volley ball sand pit, gated basketball court, extra sheds for our equipment and their crazy amount of exercise and sports gear. He stayed busy, to say the least.  Sometimes I would even take the younger kids to school when everyone else had their hands full. 

 The owner of the estate was a nice guy, at least he paid me well (30/hr) and was always friendly. They were a large family with 3 daughters and 2 sons. Well, the two oldest daughters (let's go with Madison for the eldest and Alice for the younger of the two) were my age and I had attended school with them in the past, so there was a rapport established before I started working there. This family took a lot of pride in their active lifestyle and image, and thus, Madison and Alice both had fantastic bodies. I mean god. damn. I often skipped lunch so I could clean the pool or pick weeds in the garden around the pool when they would be tanning or swimming. My second year working there they became very talkative and flirty, asking me to hang out with them after work or on my off days. I always made up an excuse because I had no intention of going down that road. Honestly, I had a girlfriend of two years and I valued her greatly. Look, but no touching. Their father would not have been pleased with me being involved with either of them, anyway. He was very controlling and already had plans for their immediate futures and I was not a part of it. 

 Months passed, I did my best to keep it at subtle flirting and even a few meaningful conversations here and there. I ended up breaking it off with my then-girlfriend after learning she had been cheating on me. After hearing this, the girl's teasing and flirting only intensified. In the spring they started doing yoga outside in the tightest booty shorts money could buy. They would even tackle me into the pool while I was cleaning it or ask me to carry their shopping bags for them to their rooms and then start asking me questions about myself to get me to hang around. Once, Madison actually took her top off to tan while I was working in a row of hedges that sits below the pool on kind of a downward slope. Like, if I had crouched down I would be hidden, but my head would peak over the edge of the swimming pool if I stood up. Her father stormed out of the house fuming mad and started yelling when he saw her. She claimed she didn't know I was there, but I mean, I wasn't being quiet, and she could've seen my head bobbing up and down over the edge of the pool as I was pulling weeds. I just pretended like I never saw anything and stayed out of it. It started getting out of hand soon after. 

 Often after work was over I would jump in the pool to cool off and then clean the pool before I left. It was really a nice way to relax because the sun would set right over the treeline that was below the pool (the house is on a hill) and light up the leaves. One evening after work, while the house was empty of adults, I was chilling on one of the floats hitting my pax when Alice walks out in a black and white striped bikini and playfully asks if I had a hard day. I laugh and tell her I was just about to leave and I would get the floats out of her way. She walked in from the shallow end and swam over to my float. She hopped up and rested her upper body on the float making me slide into her. We had a typical encounter where she says something cute or antagonizing and I am polite but dismissive. I began to paddle the float back to the side, but she was not having it. She tugged me back to the middle of their huge pool, hopped back up on the float and squeezed her breasts inbetween her arms as she rested on them. I told her that her father might get mad if he knew we were playing in the pool. She said "but you're not on the clock right now, are you?" and proceeded to slip her bikini straps off of her shoulders and push her breasts against my arm. She untied my ponytail and began to run her fingers through my hair, I could hardly think straight. All I wanted to do was kiss her neck and suck on her adorable little hershey kiss nipples, but I know there are cameras that her father can control from his phone hidden around the perimiter of the house. Best solution I could come up with was flip the float over, and pull her under with me. She gave a surprised shout and started giggling, but she played along. We made eye contact and started kissing, I slid my hand down her tight curvy ass and made her shiver with delight while she worked my shaft through my trunks and dug her nails into my chest. We came up, after what felt like hours, but was probably only 10 seconds. She tried to keep going, but I assissted her with putting her top back on and told her to wait in the steam room. I put all of the pool shit away faster than I have ever done anything in my life, ran up to my car, popped a clonopin or three, and ran back into the house praying the housekeeper didn't need to come back for any reason. I couldn't describe the feeling I had in my gut. If I got caught, I would lose the best job I could ask for without a college education and possibly get the shit beat out of me by her father (dude is a monster). But dat ass was worth any beating and I figured I had saved enough money that I could just casually sell weed to my friends and be straight till I got another job if I had to. Thus, the power of boners prevailed.

 As I walked down the stairs to the locker room, my attention wavered between listening for any slight creak or car door and practicing my breathing exercises so I don't bust a nut two minutes into the game. I became light headed probably from a combination of nerves, deep breathing, and all the blood in my body having been redirected into my cock, but I made it safely into the spa area. I removed my trunks, grabbed a towel, and opened the door to the steam room. And there she was, laying down completely naked across the bamboo bench. Stretched out from head to toe, she got chill bumps when I ran my hands down her sides and onto her hips. She grabbed my hand and led me to the bench, sat on my lap, kissed me, and started grinding her soaken wet pussy up and down my throbbing shaft. I was so worried that someone was going to find us, and she could tell because I kept looking over her shoulder to see if anyone turned on the light to the locker room. She decided maybe a blowjob would help me relax. She wasn't incredibly experienced, but that really wasn't the point. It felt great and she made up for her gag relex with a pretty smile and enthusiasm. I got lost in the feeling and started playing with her hair. This goes on for about 10 minutes before I notice the light to the locker room is on. I begin to internally meltdown, even though I told myself this was worth it. Either I am going to scar one of her younger siblings or the poor housekeeper, or her dad is about to help me make a bowel movement. Neither are great options, so I was just praying it's her mom so I at least have time to gtfo unscathed. To both of our surprise, it was Madison. Apparently she was going to join Alice at the pool, so she went looking for her. Madison started making fun of us, acting like she was going to tell her parents and playfully calling her sister a slut, but then she started walking over to us. Alice is still on her knees with her hand on my cock, and Madison begins to rub my chest and shoulders. They both start talking dirty to me, and Madison sits next to me on the bench to nibble my ear. She shifts onto her knees and leans over into my lap to finish what Alice started. At this point, I am just trying to maintain consciousness and not pass out from hyperventilating. Alice starts sucking my balls and Madison is doing her best to make my cock disappear down her throat. This was *literally*  the best moment of my existence at that point. I am so thankful that I took those benzos beforehand. I make it through a good 15 more minutes of this insanity with my load ending up partially in Alices mouth and on both of their faces. I clean them up and promise to repay them both later, because I felt that we were really pushing our luck if we went on any longer. Don't get me wrong, I would have eaten my way to their hearts had the curcumstances been different. We all got dressed, they ordered pizza, and I left. It was difficult to drive back, because I was so caught up in the sheer awe of it all. 

 I waited a week before trying anything with either of them again. We never had another threesome (if you could even call it that) but I did see the two of them on an individual basis pretty regularly for the remainder of the time I spent working for them. 

TL;DR: Banged bosses daughters in his own house.