This holiday season felt a lot different from usual. For one, it was the first time that I would be celebrating alone for Thanksgiving. The second reason was that my babysitter, object of numerous lurid fantasies, was just a few short weeks away from moving out to college. Since my wife died we’d become very close and not a week went by without me needing her services as a I struggled to juggle my work with being a single parent.
At 18 years old, Nicole was very mature for her age. She had always excelled in school and was on her way to attending one of the best universities in the country. And although she was shy at time, she always showed a big heart and was kind to anyone she’s ever met. Her leaving was a bittersweet moment, and so I was determined to make the holiday extra special…
“I can’t believe this day is finally coming,” I said to Nicole as I stood her doorway, watching her pack some of her things in boxes. “You’re all grown up now and ready to be on your own.”
She was still kneeling down on the floor when she turned to me with a heartfelt look on her face. “Aw that’s very kind, you make me want to cry whenever you talk like that.”
“I know, but I’m so used to seeing you and your smile almost every day. I’m incredibly proud of the young lady you’ve become,” I professed to her.
“Can I ask you something?”
“Sure, of course. Anything,” I replied.
She put down the things she was packing and sat down and patted a spot right next to her, signaling me to sit there, which I did.
“If I ask you this, will you promise not to get mad or upset with me?” she asked in a serious tone.
“Of course Nicole. You can trust me.”
She took a deep breath. “I’m really nervous asking you this, but here it goes…I’ve never went ‘all the way’ with a guy before. I know it’s going to happen eventually at college, but I want it to be with the right person. I my first time to be special, with someone I love, and who I know loves me back not some jerk who’s only looking for sex. That’s why I want it to be with you. I want you to make me a woman.”
I was immediately taken aback by my this request. I felt shocked and utterly confused at the same time. I had dreamt of fucking her, but never thought for a moment she would offer herself to me like this.
“Did I hear that right,” I asked skeptically.
She nodded, “You did. I want you to take my virginity. And I’d rather it be you than some guy who’s going to turn out to be a total creep like some of the boys I’ve already dated.”
“My god, Nicole, I’m speechless”
“You promised you wouldn’t be mad,” she replied, in a hurt voice.
“I’m sorry, I’m not mad,” I told her as I calmed myself down. “It’s just that something like this isn’t normal. There’s an age gap, and there’s a line that should never be crossed between us. God, if anyone ever found out…”
“But no one will find out,” she interjected. “I would never tell anyone, and I know you obviously wouldn’t tell either. My virginity means a lot to me.”
I sat there shaking my head in disbelief. “I don’t know about this Nicole. You know I’m very fond of you and that I would do anything for you, but this…”
“Will you at least think about it?” she asked. “Can you give it a serious thought for me?”
I gave her kiss on the forehead and tried my best to avoid her question.
I could barely sleep that night after that conversation with Nicole. How could she ask me such a thing? How could she want me to do that to her? I was either the luckiest guy alive, or about to make a terrible mistake.
But what bothered me the most was that I couldn’t stop thinking about what it would be like to accept her offer. I thought about what it would be like to hold her petite little body in my arms as we made love. I imagined the arousing notion of me being the first man to truly, as she put, ‘make her a woman,’ as I looked deep inside her large and innocent eyes.
I then did the only thing I could do at that point- masturbate thinking about her.
We had lunch together the following afternoon, and to my surprise, it was as if nothing was out of the ordinary between us. She never brought up anything she mentioned the night before and there was no sense of tension or awkwardness between us. She was all smiles as usual and we had a great time enjoying each other’s company.
“Mmm…that was delicious,” she said as she cleaned the leftover turkey and mashed potatoes from her plate. “I’m really going to miss your cooking.”
“And I’m going to miss sharing these meals,” I replied with a smile.
She smiled back and winked, “Thanks dad. And that reminds me; I woke up extra early this morning to bake us some desserts. I’ll be right back.”
In a flash, she got up from her chair and rushed to the kitchen. I heard the oven open where she had hidden them, and she returned holding a plate full of carefully arranged baked goods.
“I hope you like cupcakes,” she said in a upbeat voice, while striking a model pose with the pastries as if to advertise them. “I made them with holiday decorations, and they’re just for us.”
“Of course, I love them. And the fact that you made them makes it even more special.”
“You’re so sweet,” she replied. “Now eat up while they’re still warm and fresh.”
She then placed a single cupcake on my plate. The cupcake itself was chocolate, and it was topped off with a white colored frosting, along with red and green sprinkles.
“This really does taste amazing,” I told her truthfully after I took the first bite.
“Well thank you. The cupcake I made from a package, but I made the frosting from scratch,” she said proudly.
“I can tell. I’ve never tasted anything like it before. I could literally eat anything as long as this frosting you made is on it.”
“Anything?” she asked with a naughty grin.
She slowly moved her chair back and stood up. Her fingers wrapped around the bottom of her sweater and pulled it up over her head, and she placed it comfortably on her seat. She wasn’t wearing a t-shirt underneath, just her bra. My eyes became glued to her chest, watching it move as her arms reached back to unclasp her bra to let it fall to the floor.
I gasped a little at the sight of her bare breasts. They were small, b-cups, and they looked firm the way they pointed straight forward. Her areolas were small, but her nipples were visibly large for a young woman with her body size. They were bright pink, which made a nice contrast to her pale skin color.
She picked up her cupcake and pressed the top of it against the center of her breast; twisting and turning it so that the frosting covered her nipple. Once she was done coating one nipple, she did the same to her other breast so that both of her intimate areas were covered.
“You would eat my frosting off of anything?” she asked again, but this time referring to her nipples.
I struggled with nearly every sense in my body and mind as my exposed babysitter came closer to me. I should have stopped her, but I couldn’t. Because deep down I didn’t want this to end. And she damn well knew it as we looked into each other’s eyes.