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Babysitter gets her dream

Volume one

By DSPublished 3 years ago 10 min read
Babysitter gets her dream
Photo by Dainis Graveris on Unsplash

Our babysitter just graduated college and was off for the summer. Me and my wife Julie run our own company and travel a lot. Jessica our babysitter has been a wonderful help. She took most of her final year of classes online so she could stay where she wanted as long as she had an internet connection. For the past year she has been staying with us as an on-call babysitter. Our meetings and trips usually happen quite random, so it has been nice having her stay with us.

My name is Ryan by the way. I have the most travel time as I do most of the sales meetings and the setups for our products. Whenever it is just me leaving Jessica and Julie help one another out and manage the business and the kids together. We have offered Jessica a full-time position with us as she has been so valuable in the past year. She is going to train with me and start doing some sales and some setups so we can expand the business.

Jessica has her own room with her own bathroom and takes her meals with us and the kids. She loves this arrangement because she can start saving for her own place. We have the utmost respect for her.

We just got a chance at a startup company in California, it is only a few miles from Hollywood. We decided that Jessica would make the trip with me so my wife and kids could go spend time with her parents in New York while we were gone. My wife has been working with Jessica for a while now and they both seem to giggle a lot, but she has learned the products.

Our plane lands in Los Angeles and we catch a cab to our hotel. We left a couple days early so we could sight see some. We ended up with adjoining rooms at the hotel which was great. We did not have to lug our gear from room to room. I just left my door unlocked in case Jessica needed anything. It was late when we arrived so we ordered room service and decided we would get an early start tomorrow.

The next morning, I was in the shower when I heard the adjoining door open and close again. I did not think anything of it until I stepped out of the bathroom totally naked and there stood Jessica. Her camera in hand snapping pictures as I was drying off. I was a bit shy, but Jessica did not seem to mind one bit. She even came over and knelt so she could get a good side view of my Johnson.

Jessica was giggling so hard as she said, " Your wife is going to love this picture. She wanted pictures of our whole trip and I promised I would deliver them. "

I heard the effect of the email being sent. I was beginning to get dressed now as I thought my wife had put her up to that little stunt just to break the ice on our trip. I had just found my shirt and got it on when I heard Jessica's phone ring for the video app she uses. It was my wife on the other end.

My wife said, " That member looks a little flat Jessica, I want to see it grow. Grab that thing girl and let us see it loud and proud. Stick it in somewhere that usually does the trick for me. I want to watch though. "

Jessica comes over and slams me back on the bed and takes my tip into her mouth and starts sucking me. I grow hard as ever. She takes me down her throat deeper and deeper each time. I can hear my wife loving every minute of it from the live footage. She is so talented and has me exploding in her mouth in a matter of minutes. Her tongue wrapping around my member and squeezing every drop from me.

Jessica stands up licking her lips and hands me the phone.

My wife says, " Happy early anniversary baby. Jessica said she would not mind filling in for me this weekend. I told her that she could work in whatever she wanted too this weekend because she is playing me on your trip. I know you have not ever strayed, and I am alright in our relationship to share you some. Besides Jessica said she thinks you are pretty hot for an older dude. "

My mouth dropped; I was speechless. The girls were both giggling loud as ever. I passed the phone back to Jessica and got dressed. We went down and had a nice breakfast and went sightseeing till late evening. We made it back for a nice late dinner and a few drinks.

I dropped her at her room and went to mine. I stripped down and turned on the air. I jumped into bed and fell asleep in minutes of going to bed.

I was awakened later in the night with a naked Jessica sliding my now hard member into her very tight love machine. She had me half-way in and was already moaning from my size alone. She was on her feet lowering herself onto my rod. She had a real steady pace of twerking my rod. She kept thrusting me deeper and harder. She had grabbed a hand full of chest hair and was riding me like a horse on race day. Her juices pouring out alongside my shaft as she kept pounding away at me. She was really abusing my rod twisting and turning with each stroke down. It felt rather weird and odd yet very hot and full of pleasure at the same time.

She slammed down hard on my shaft. So hard her little mound hit my mound and she shrieked in pleasure as she coated my rod in her juices as she climaxed. Her hot juices and her whole love monkey enveloping me was too much and I exploded deep inside of her hot body.

She reached down and grabbed her phone and turned it around. It was my wife again. She was nude in bed playing with herself.

She said, " That looked fun honey hope you enjoyed yourself. I know Jessica is. She told me that this was her dream. She wanted you for her graduation present. She enjoys the job and all, but this is what she has been dreaming of. You make sure you two have plenty of time now. I moved the meeting out a day so you would have extra time to play. Nightie night and sweet dreams baby, enjoy. "

Just as my wife clicked the phone off Jessica had spun around and started nibbling on the tip of my rod. She was busy running her tongue up and down my shaft and swallowing every bit of it. Her small hands were squeezing my shaft as to milk it. Every drop that came out she would lick off.

Having tongued me clean she came up and laid beside me, one leg over mine and her arm around me. Her head resting on my breast. Her tongue licking on my nipples as she slowly quit quivering from our exploits.

I awoke the next morning to breakfast in bed. Jessica had showered and put on some exotic teddy that showed her four-foot nine-inch body off wonderfully. Her breasts were pushed up and both nipples as hard as rocks. Her cute mound in a pair of black lace crotch-less pair of panties. Covering her whole body was a flimsy see through robe of pink material. Her long blonde hair in a ponytail behind her.

She let me eat breakfast then led me into the bathroom and the huge tub for two. She ran it full of bubbles and set me into it. She cleaned me up from head to toe. All the while one hand was always slowly working my shaft keeping me nice and hard. She pulled me from it and dried me off using care not to forget my shaft. She kept him hard for almost a full hour of slow stroking and a nibble or two as she worked drying my body. She put me into a special massage table where she kept her magic up. Her fingers were working all over me. She had me nicely oiled up all over.

She pulled me to the bed after she took off her robe and panties. She put me on bottom and took special care to rub her little nubbin with the head of my well-oiled shaft. She was moaning in minutes and climaxed all over my head of my shaft.

Rubbing all her juices on my still very oily member she lowered her body down and placed me at her back door. Ever so slightly she dropped herself onto it. First the head went in, and she would hold it for a while. Then she would let it go deeper. Little by little she took all of me into her hole. She slowly began a nice steady pace. It was so tight. Just as tight as her love monkey. She was moving with such precision. She massaged my chest as she worked up enough nerve to start a faster pace.

It was not long, and she had my shaft buried deep into her and I was exploding a huge load of my juices deep in her body. It was unlike anything I had experienced in a very long time. My body was quivering all over as she slowly stroked me in and out of her body.

I grabbed her and pulled her down to my chest and started kissing her and holding her so hard I thought she would burst. My rod slipped from its canal with a weird noise. Jessica started giggling and kissing me back. She was nibbling on my whole body using her teeth. It was so much to bear.

I finally grabbed her by her sides and lifted her petite body up to my mouth. I parted her lips with my tongue and started tasting the juices fit for a god. She was so sweet tasting. Her juices were like pure honey. Her lower lips were covered in it. I managed to find her nubbin and sucked it into my mouth. Rubbing her nubbin with my tongue as I sucked on it.

She was going nuts while I licked her love monkey. Her moans were loud as ever. She was grabbing and rubbing her huge nipples as I devoured her love nest.

I worked on her shoving my seven-inch tongue deep into her love hole every chance I had. Licking her G-spot with the tip of my tongue while she held on to the headboard for support. I grabbed her nubbin between my teeth and flicked it with my tongue and she let out a hellish scream. So loud the maid that was cleaning her room came in to see what was going on in my room.

After making it into the room she started giggling like a schoolgirl.

The maid apologized and was all red in the face and could not stop from smiling ear to ear. We were a sight. I had Jessica straddling my face and it was covered in her juices.

Jessica not wasting an opportunity spun herself around and engulfed my semi stiff shaft while the maid was still there. She made a drama act out of it and a lot of sucking noises. Slurping it down and whacking her cheek with the tip spilling out some clear liquid every time.

The maid had lost her voice, I think. In between my moans I asked if she would get some more towels for my bathroom since she already seen what was happening. She was way cool about the whole thing. She even took some pictures for us after she got the towels. She was giggling the whole time. You could tell it was not her first time walking in on someone.

Jessica made sure I exploded while the maid was in view of the bed. She worked extra hard and pulled me out just in time. I shot my load clear across the bed and right onto the maid’s face. Just one glob made it all the way over, but it was funny what the maid did next.

The maid stuck out her tongue and licked it off the side of her face and swallowed it. She was giggling the whole time.

Jessica said, " It tastes sweet right. "

The maid nodded and went on about her business.

Me and Jessica got all cleaned up again and went out for lunch that day. The motel had a wonderful area to dine in, so we saved time and ate there.

The next few days were filled with business but we managed to enjoy ourselves some more before going home. The wife sat down with me and explained what was happening after we got home. Her Cancer had returned and she was not taking treatment this time. Her and Jessica worked it out a few months ago and had been hiding it from me. Julie has in a matter of months trained Jessica to handle her side of the business and was her pick to help finish bringing the kids up.

I love my wife so much and for her to be so giving at this point in her life was overwhelming. She had everything worked out and all the details already planned out. We all three had another wonderful year and a half together before she passed. I think of her daily.


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