I'm a single dad with 2 kids. 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 that 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, that I invited her to join the kids and I for dinner at a local restaurant we already had plans to have dinner at.
She was not only on time, she was there before we were. GREAT start as I believe in punctuality. She sent me a txt 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! Medium-length straight-auburn hair, light complexion, 5'0, 95 lbs. and 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 went PERFECTLY!
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. 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 her if she would be interested in becoming a live-in nanny.
After thinking about it briefly, she said, "Okay, sure."
So, Robbi Jo was now moving into my new home with me and the kids! 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 jammy 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?"
"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." She replied.
I then said, "Robbi, why don't you just go sit down on the couch and I will get you some chicken noodle soup."
"Ok. That would be great," she gushed.
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 said "Ok."
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 strattled her ass with my own jammie-protected cock region. I was wearing flannel jammi 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 or pull away.
My cock was so hard by then I could have cut diamonds with it. I massaged her from the hair on her head clear down to the 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, strattled her ass again, and began massaging her lower back waist. Robbi then 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 pajama bottoms off. My new view was a glistening young pussy completely soaked with her own juices. She was incredible, so sweet, so innocent. I stopped massaging her and began planting little kisses down her back, starting up high. Then slowly moved down to her ass, as it was laid out in front of me. I stuffed a pillow underneath her pelvis to lift her ass up higher, then I dove in.
My tongue slowly slipped into her tight little asshole. She moaned and spread her legs farther apart granting me deeper access. I dipped my tongue deeper inside and tasted her from within. Her moans were becoming intense and she was lifting her perfectly round but cheeks up to meet my mouth. After several minutes and a lot of panting, I removed my tongue from her ass and slipped it into her virgin cunt.
I ran my tongue around the rim of her hole savoring her juices. I probed her ass with my finger and began finger-fucking her in her glory hole, while at the same time fucking her cunt with my tongue. She was moving her hips back and forth grinding her ass into my face totally in sync with my movements.
"OOOOOhhhhhhh!!" She let out a blood curdling scream as she came hard. She was spewing fluids from her body, and I labored quickly to lap them all up.
All though I was hesitant at first to truly and completely breach our business relationship, I believe it was worth it. I felt her hand reach from behind and grab my hard cock through my bottoms. She forced her hand in the fly opening on the front of my bottoms and retrieved my cock from its hiding spot. She squeezed me tightly in her hand and urged my cock towards her opening. I took control and guided myself into her sopping-wet cunt.
I let my morals melt away. My cock had begun making all my decisions for me. I rammed her hard from behind and she screamed my name out loud. I savored the moment, my cock was so tightly squeezed inside the tight little cunt of a woman half my age.
I then realized I did not have any protection on. I asked her if she was protected and she responded. "Don't worry, I have the ring inside me."
After hearing that I felt relief and tried to really enjoy her, while holding back my cum for as long as I could. I pounded her for almost half an hour, and was beginning to feel a little sore. I turned her over on her back, spread her legs and sucked her clitoris into my mouth. I teased with my tongue and she was going wild bucking and grinding her hips.
I decided to try to take advantage of her vulnerable state. I turned her back over on her stomach. Feeling brave and in the heat of the moment, I then asked her if I could fuck her in the ass.
She reached behind her and squeezed my sticky cock. "Well, I've never but yes. Yes, I don't care. Just fuck me."
Her ass was so tight it was a little painful trying to get inside of her. I think she began to sob, but my cock decided to trudge on. Slowly at first, I snaked my way in and out of her forbidden hole. The deeper I went the louder her sobs became. After several minutes I had worked all seven inches inside. I fucked her tight little ass hard unaware to her screams until I came in her ass.
It was an incredible night for us both. We had several days, nights, and weekends like that when my kids were at their mom's house.
Robbi Jo finally graduated from college and found a job in SO Cal in her career field. It was a sad departure when she left! I will never forget that young woman.