tagFirst TimeBabysitting Daddy Ch. 01

Babysitting Daddy Ch. 01

byluvrobbijo©

I'm a single dad with 2 kids. Their mom lives in the same town and we share them 50/50. Daycare centers are expensive, and most require parents to pay regardless if the kids show up or not. So I opted to seek out independent day-care providers/babysitters.

I hired a young lady after searching a local independent daycare website. Now most of the "sitters" on this site are young college students looking to help pay for college. I was a college student myself, and admired anyone trying to help themselves! Anyway, the first young lady I hired was OK, but she was more interested in talking and texting on the phone with friends, etc. instead of spending time with and watching the kids (the kids advised me of this after so long). Within 3 months, I had to let her go. So there I was again, looking for another provider. I posted an ad on this same site and interviewed several candidates. I always met the candidates at a local coffee shop and paid for any expenses. I also made sure the kids were with me to see if there was/was not a connection between them. I finally narrowed it down to one or two young ladies. THEN, just a few days before I was going to make my decision, another young lady came into the picture as she answered my ad I still had posted. The ad included my contact info, and after she posted her interest in the position, she called me. This was the first candidate that had ever called me prior to meeting me. We talked for almost 30 minutes. The conversation was incredible, and I had a great feeling about her as a daycare provider for my kids! I was so impressed with her I invited her to dinner at a local restaurant where the kids and I had previous plans to dine.

This young lady was not only on time, she was there before we were! GREAT start as I believe in punctuality! She sent me a text letting me know she was there already. When the kids & I walked into the restaurant, I immediately laid my eyes on the most beautiful woman I had ever met in my life! It was her! Robbi Jo! Early twenties, medium-length straight-auburn hair, light complexion, 5'0, 95 lbs. at the most, gorgeous petite figure, infectious smile, small-breasted (I'm not a breast man), perfect ass (I AM an ass man), and the greatest swagger I've ever seen in such a young woman! I was in awe! She was like a magnet to my kids! They knew who she was before I really knew! It was the most unbelievable first meeting I had ever had with a potential sitter! The dinner and interview were both PERFECT! Robbi was definitely the bomb! I not only wanted her to watch the kids due to her personality and skills/abilities with the kids, I also (secretly) wanted Robbi from that night on for myself!

She began watching the kids shortly thereafter. Robbi lived in an apartment near my townhouse. All was convenient. Then, I bought a home on the other side of town -- a 4-bedroom home, and that meant a bedroom would be unoccupied. I asked Robbi if she would be interested in becoming a live-in nanny! After thinking about it briefly, she said, "Sure!" So, Robbi Jo was now moving into a new home with the kids and me!

Robbi was awesome! Got dinner started for the kids before I got home. Sometimes, she even got it started or ready before I got home when the kids were at their mom's house. I allowed her to bring friends over (and her friends were just as HOT as she was). During the early months of the year she lived with us, she once complained about a stiff neck and back (probably from the stress associated with going to college, working, etc). I offered to give her a massage, but she didn't think it would be appropriate to get a massage from her employer. I understood and respected that.

Then, a few months later, when the kids were at their mom's house on a weekend, Robbi came out of her room in flannel pajama bottoms and a t-shirt while I was in the living room. Even though she said she was not feeling well, I still felt she looked BEAUTIFUL -- even sexier in her current attire! I then asked her, "You ok? What's wrong?"

She replied, "I'm not feeling too well. I think I'm getting a cold and just want to get myself something to eat and go back to bed."

I then suggested, "Robbi, why don't you just go sit down on the couch and I will get you some chicken noodle soup."

She said, "Ok. That would be great!"

I warmed up some home-made chicken noodle soup I made the night before and gave it to her. I let her eat it while I did my things around the house. When I returned to the living room, she had finished her soup, but she told me that she still wasn't feeling all that great. I then said, "Let me give you that massage I've been telling you about." Without any hesitation, she agreed.

At first, she laid down face-first on the couch. I tried to work with it, but then suggested that my or her bed would be better if she was ok with it. She quickly got up, grabbed me by the hand, and led me into my bedroom.

Robbi stayed clothed in her flannel jammies and t-shirt while she buried her face into my bed pillows. I began massaging her from the side of the bed. This was not working very well, so I jumped on the bed myself. Trying to remain reserved, I tried to massage her closer, but still from the side. Then I thought....."What the heck....just try and straddle her and she what she does!" So, I did. She didn't flinch an inch! I straddled her ass with my own pajama-protected cock region (I was wearing flannel pajama bottoms as well). Then, I worked my massaging hands up and inside her t-shirt instead of massaging from the outside of her shirt (she was NOT wearing a bra underneath that t-shirt). Again...she did not flinch! My cock was so hard by then I could have cut diamonds with it! I massaged her from the head-hair down to her cute toes! When I moved to her ass (covered by her flannel jammies), she allowed me to pull them down just a bit to massage her upper buttocks! I literally was ready to cum all over her! But I held back and tried to maintain some professional composure! After massaging her thighs, feet, and toes, I moved back up, straddled her ass again, and began massaging her lower back (waist).

Once I was straddling her ass again, Robbi arched her back and raised her ass in the air -- taunting me! My cock was hard already, and Robbi's reaction almost made me cum right then and there (but I controlled myself)! She then said, "Gary, take my jammies off. I want to feel your hands all over my entire body." I then took her bottom jammies off. My new view was a glistening young pussy completely soaked with her own juices! It was incredible! I stopped massaging and started kissing her back (up high at first), then moved down to her ass as it was perched out in front of me.

I put a couple of pillows underneath her pelvis to get her ass up even higher. I then dived in! My tongue slowly slipped into her watering hole. She moaned and enjoyed for a long time until she came 2 times. Then, I slipped my tongue into her forbidden hole and rimmed her good while finger-fucking her in her glory hole at the same time! She had at least 4 orgasms! She was spewing fluids from all over her body by now!

Then...even though I was hesitant at first to truly and potentially breach our relationship, she reached from behind her and grabbed my hard cock out of its hiding spot in my jammies that had been knocking at her door this entire time, and guided it into her sopping-wet cunt! I didn't think about it anymore! I stuck my hard cock into her from behind and she screamed my name out loud! So now, my cock is inside the tight little cunt of a beautiful young woman half my age!

I then realized I did not have any protection on! I ask her if she was protected and she said, "Don't worry about it I have the 'ring' inside me!" Once hearing that, I pounded her for at least half an hour! Then, turned her over on her back, put my tongue and lips into her for yet another hour! Feeling brave and in the heat of the moment, I then asked her if I could turn her over on her tummy and fuck her in the ass! She said, "I thought you would never ask!" I then fucked her hard in her tight ass until we both came again and fell asleep in my bed.

This was an incredible night between and for us both! We had several days/nights/weekends like that when my kids were at their mom's house!

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