Confession Ch. 05: Bad Babysitter

It was the summer after I graduated college. Just like most college students, graduation day comes and goes and you're left figuring out what is next. I stayed in my little college town with my boyfriend and had a number of really menial jobs. It was a rocky summer though.

My boyfriend and I were just drifting apart. I was out of school trying to figure out life and he was still in the college routine. We didn't really fight or have major issues, things just weren't the same anymore. We were in different stages of life.

It was that summer that began babysitting for the Joneses. They were a family that seemed to really have it all together, including a massive mansion of a house. They needed someone that was a blend of tutor and au pair, but with the flexibility of being on call. Since I had other jobs, I told them that was fine and didn't need to be employed full-time. By late summer, I felt like a member of their family.

They were a beautiful couple with two beautiful children. We would often spend time in their pool or hot tub and they are what you would imagine a fit husband and wife would look like. Both were very confident in their bodies which often made me feel a bit less confident about myself. I wasn't one to hit the gym everyday and I would eat junk food more often than I care to admit. My genetics kept me attractive though.

When staying with them, I had an entire suite in their basement that opened up to the pool. I loved every opportunity to stay there instead of the near-campus apartment that I could afford. It seemed like an oasis that I got paid to stay in. Some nights I got paid to barely work, while the rest of the time we all hung out as a family. I would do some light tutoring, help with dinner (unless we ordered delivery), and help get the kids ready for bed and tucked in.

The rest of the night would be hanging out, watching a movie, a glass of wine or a cocktail. It was a really relaxing getaway. It was also a good escape from the reality of dealing with my boyfriend and our diverging paths. Once or twice a week I could live like a princess in a castle.

It was Labor Day weekend when things went too far.

Saturday morning I left my apartment and headed their way. I was invited to spend the day helping watch the children while hanging out by the pool. It was sunny and hot and we spent all day playing, splashing, and drinking margaritas.

It might have been partially my fault. I had an older bathing suit on and the top was having a hard time containing my breasts. I kept readjusting the straps and hoping that everything stayed in place. I mean, he always looked my way, but his wife was way hotter than me.

She was toned in the way that only a mom who does yoga looks. Thin, firm, with an ample bosom of her own. I was envious of her perky boobs and chiseled butt. She was the epitome of a MILF and someone I aspired to be one day.

Early in the evening, pizza arrived and I'm sure I was a pig when downing the greasy food but it was irresistible after the heat, swimming, and tequila drinks. As the sun started going down, it was time for the kids' bedtime routine. I helped Mrs. Jones get them showered and into bed where they quickly fell asleep from exhaustion. Heading back outside it was time for more adult beverages and pool-side chats.

Another couple of hours passed and we had fun laughing and joking like we always did. Mrs. Jones was definitely feeling the tequila as her giggling moved towards more open flirting with her hubby. She leaned over and whispered something in his ear and shortly they were saying goodnight and heading back up to the house. I can only imagine what she said to him.

I took the last of the margarita and poured it into my cup. Sitting on the edge of the pool I looked up at the stars while the tequila swam through my veins. The cup eventually went empty and it was time for bed. What a buzz I was feeling as I walked back up to my suite. I slid the door open and slightly stumbled into the room.

I walked into the bathroom and turned on the shower to rinse off the chlorine before bed. That's when I heard a soft knock. Turning around I was staring directly at Mr. Jones, completely nude, walking into my bathroom. In just a few quick moments he was taking me into his embrace placing his lips on mine.

I felt the warmth of his body. I was caught off guard and slightly pulled away. He must have read my face because he quickly said, "she fell asleep already." He turned his attention back to kissing me. I didn't protest one bit.

Pulling open the shower door he led us both inside. As the water hit me, I felt his hands untying my top. The pressure of my confined breasts all day was released and they fell free against his body. My top fell to the ground and he pressed tighter against me. My back was now against the cold tile and he wasted no time enjoying my now free boobs.

He took my nipples in his mouth but kept quickly moving down my body. First my stomach, then right above my bikini bottoms, then traced his tongue down me as he peeled them off of my hips. Pulling them down his mouth found my lips, then clit, moving between my lips and then in and out of my opening. I was so wet so fast.

Standing back up I felt him moving the tip of his manhood back and forth between my lips. With a single thrust he startled me and pushed hard inside of me. Quick hip motions had me moaning, eyes closed, my back against the tile shower. Finally fully inside me, pleasure increased and our hips moved in motion. In just a few moments he pulled me down and began stroking himself in my face. As expected, he spurted a few hot ropes out across my face and chest.

Quietly, he kissed my forehead and exited the shower to return to his wife. I sat there letting the shower rinse me clean of my dirty deed. After a few minutes, I washed myself off, dried off, and got in bed.

Replaying what had just happened, fueled by not finishing, my thought raced. I felt so naughty and touched myself accordingly. I was a bad babysitter, wasn't I? I just let him come all over me with his wife upstairs. It was hot and had me all worked up. I had to do something about it.

I put on a long t-shirt and quietly walked up the stairs. What was I doing? I thought. It's not fair for men to have all of the power. I wanted to come too. I was revved up and needed something. Anything.

The stairs opened to the living room and I quietly circled the first floor. No one was around so I continued up the next set of stairs to the second floor. Their bedroom door was slightly cracked and I slowly pushed it open. From the moonlight coming through the window I first saw Mrs. Jones completely naked on the bed, seemingly passed out. She must have gotten him worked up before the alcohol took over and forced an early night.

I moved to the other side of the bed, careful to tiptoe. Mr. Jones seemed to be asleep until my hand moved down his chest. His eyes met mine and a worried look came over his face. Was I there to ruin his night? Was his secret about to cause problems?

I hope he was pleasantly surprised when my right leg quietly swept over him until I was straddling him. I slowly moved myself against his soft penis, hoping it would come back to life. I reached down using my hand to help my soft, slow movements. It took a few long minutes but the wetter I got the harder he got.

His eyes kept darting between me and his sleeping bride. I soon had something to work with and lowered myself onto him. It didn't take many motions to feel him move entirely in me and I used my hips to enjoy myself. Looking over, I worked over Mrs. Jones in my mind, admiring the body she worked so hard for. The more I looked at her the closer I got. Then, suddenly, I went over the edge and enjoyed an incredible orgasm.

I could have let him finish but I was done. I wasn't sure how much time we had either. I slowed my movements until I stopped and quietly climbed back off the bed. I made my way back down two floors and crawled into bed, smiling that I pursued my own pleasure in that moment.

The next morning was a mixture of awkwardness, kids screaming, and hangovers. I took the opportunity to head home and leave them in the chaos. I'm not sure if something was said, or it was simply that Labor Day was the end of summer, but that was the last time I set foot in their house.