Pt. 0 -- A Prelude
Couple takes their babysitter to a fantasy dinner
Tags: Babysitter, Bisexual Female, Female Masturbation, Resturant
Addendum Author's Note:
The following is a story I wrote that inspired me to write the sequel story "The Gifted Student." I'm sure I will one day do a rewrite to properly reform this stand-alone story to be better integrated to the main story, but for now, I am going to basically leave it as I originally wrote it, and republish it as a Prelude.
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Author's Note:
I recently came across a story here on Literotica that I highly enjoyed. It had a refreshing through line, and a setting that resonated with me. But as I read though it, I realized the author had missed a huge opportunity. Its third-person POV wasn't as effective as if the story would have been written from the POV of its young protagonist. The author even wrote the line "(They) wondered what was going through (the protagonist's) mind." As a reader, I was jumping up and down saying "I agree!!!! Tell us!!!" In a fit of passion (needing a creative outlet in this age of covid, and seeing something so good just missing so little) I sat down and started rewriting the story. As part of my challenge to myself, I tried to include as much of the original story as possible, both for the challenge and the homage to the original author. There were challenges, but I surprised myself by just how much of the original I was able to preserve while rebuilding and adding around it. I guess it ended up a literary "This Old House" job. The original form of the building is still there. But I fixed a ton of things that didn't work for me and maybe added a new room or two. I did make an effort to contact the original author for a blessing of this rewrite, but was not able to make contact.
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Gifts Honestly Given
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"Did you have a nice time?"
The Wingers were a nice couple I had been baby sitting for a few years now. They had just gotten back from a Friday evening out with friends.
"We did." replied Kathy, with a smile.
I always enjoyed babysitting for Kathy and Jerry. They were great employers. Little Billy and Lisa were still young enough that bedtime came early, and I essentially got paid generously to do the homework I would be doing anyway. Plus when I wasn't studying, they allowed me to use their incredible media center. Yeah, my folks were fellow members of the county club with the Wingers, but Ma and Pops were too busy running their restaurant to justify investing in such a premium rig.
As Kathy handed over my night's earnings, she said "Tara, Jerry and I want to take you out for a celebratory dinner. We're just so happy you were accepted into Roxbury College. You have always been the best babysitter we ever had, and would like to take you out for a very interesting dinner event. We are looking to do it tomorrow night."
"That sounds amazing. I would love to go. That is so nice of you. What should I wear?"
"Just wear a dress and heels. Something special like you would wear on a date."
"Okay. I can do that. I am so excited."
"We'll pick you up at around seven o'clock tomorrow evening. Sound good?"
"I cannot wait."
Kathy smiled again. She was such a beautiful woman. Always perfectly dressed, I had often been inspired by her style and manner. As great as my Ma is, she is a bit nouveau riche. While I had learned from her the love, drive, and ability that made her rise in the world possible, she still had some of the base coarseness that didn't play well in some of the parlors we now found ourselves in. Mrs. Winger was an excellent role model to emulate in those ways.
Jerry walked me out to my car. "Sorry we were running late tonight." he said as I swung my purse onto the passenger seat. "Would you like to stay over? We can set up the guest room for you."
'No that's okay. I will be fine. I told my parents I would be coming home. Thanks anyway." I replied a bit sheepishly.
"Tomorrow let them know that you will be spending the night out. Just so they know ahead of time."
"Will do. My folks are trying to let me, you know, "Adult" now, but after nineteen years, 'Tiger Mama' doesn't quite know how to, you know, let go..." I said with a bit of goofy smile. "Just the other she was telling me that, in her day, she ... I'm sorry, Mr. Winger. I won't keep you with that rambling story."
As I departed, I laughed at myself. I always seemed to get so flustered when alone with Mr. Winger. But could you blame me? He was successful, intelligent, kind, and charismatic. And looks wise, he was almost beyond desire. He was what all the guys on the Bachelor wanted to be. There was this time last summer where the Wingers had hired me for an afternoon to corral Billy and Lisa while they hosted a pool party. Jerry wore this incredible tangerine speedo that just made me melt. After the party, I made an impromptu beeline for my then-boyfriend Jean-Paul's house for what he later called "a highly memorable evening." What Jean-Paul never knew about that evening was that in my mind, he didn't even register. It was all me, the beach, and the contents of a tangerine speedo.
As I pulled into my parent's driveway, the memory of the tangerine speedo was getting me all hot and bothered. I made way way to my bedroom where I quickly stripped down to nothing. As I laid down on my bed, I reached for the drawer where I kept my toys. After pondering between Lightyear and Goodyear, I decided to go with both. I know it is a sophomoric humor, but I liked the puns involved. My Buzzing vibe makes me feel Light-headed, and my rubber dildo fills me up Good. I flicked the switch on Lightyear, laid back, and the fantasy began. I was here in my bedroom with the Good-Looking Man. We were in a naked embrace, deeply kissing. As Lightyear and my free hand drifted over my body, I could feel the good looking man's hands stroking me. His big, strong hands were gentle, stroking each of my erogenous zones just right, putting me right on the edge of orgasm and keeping me there. He was so expert. When I couldn't stand it any more, I told I him I needed him inside me. I needed to feel his big cock, stroking me long and hard. The good looking man smiled, and pulled me over to the edge of the bed where he could stand over me as he buried his cock deep into my pussy. With long strokes, in and out, he used his hands on my hips to control the rhythm. I then felt a second pair of hands on my breasts, stroking my hard nipples. After feeling a nibble on my ear lobe, I heard Kathy Winger whisper softly, "You are such a naughty girl, fucking my husband." I came, and I came HARD.
When I finally regained consciousness, I pulled Goodyear out from his position deep in my pussy. I was able to stagger to my feet, and started towards the bathroom to clean up. As I wiped myself down with the washcloth, I had to look at myself in the mirror. First, that orgasm was incredible. It was far and away the most intense I had ever had. Being honest with myself, I had to admit the reason why. Like most people my age, I had done my share of exploring porno on the net. Girl on girl was cool in that I could relate to how all the actors felt, but it wasn't that sexy to me. No big deal, I just guessed I was straight. But somehow the tiniest thought of Kathy Winger nibbling my ear had epically rocked my world. I couldn't explain it. Mr. Winger was a bit more explainable I guess. While I can't say I ever dreamed of fucking him exactly, I was forced to admit the avatar in my dreams of the Good-Looking Man was mostly him, mixed with a few whisps of old boyfriends and maybe a ghost of a teenybopper boy band. Laughing at myself, I figured I may as well wish to win a million bucks too. They were such a beautiful, perfect couple, and I am just a bookish babysitter from the neighborhood.
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The next day I was able to laugh at myself some more. "Look honey, here comes babysitter Tara. Should we fuck her brains out?"
"Sure, Kathy dear, the gawky neighborhood girl is SO much better than being with you! HAHAHA!"
I was going to make the best of it though. Kathy had said dress like it was a date. So what if I took her at her word, and dressed like it was a third date? I did all the extra shaving and primping, and put on the yellow dress I had been saving for graduation over a racy bra and panty set. Kathy and Jerry would never know, and after dinner at whatever jumped up Applebee's clone they were taking me to, I'd be ready for a bit of sexy time. It was really a shame I was between boyfriends...
My phone beeped with the text that Kathy and Jerry were on their way to pick me up. I grabbed my purse and went out to the end of the driveway, looking for the Winger's BMW. I was shocked when a limo pulled up. I knew Kathy had said "nice date", but a limo said something akin to "once-in-a-lifetime" like prom. The driver opened the door for me, and I slid in.
"Tara please come inside." said Kathy. "You look amazing. We will be taking you to a wonderful little restaurant we know. It is kind of different, but very amazing. We'll be taken to a location where ten people will enjoy a scrumptious dinner."
"You two look incredible as well!" I said, taking note of their finely tailored clothes. Kathy was wearing a black slip dress with black high heels, and Jerry was wearing a nice shirt and a jacket with slacks.
"Tonight will be fun. I can't wait for you to experience the restaurant." said Jerry.