The Babysitter: Chapter Two

Over the next few weeks, I could hardly think of anything but the idea of wearing girly clothes and how sexy it would feel. Every house I babysat at now, I would not just go through the underwear, I would dress up in it. I began to build up quite a collection of soiled panties stolen from the women of the neighbourhood. Some I would wash and return, others I kept as souvenirs.

It began to grow beyond just panties, babydolls, bras and basques. I began completely to dress in a feminine fashion with skirts and dresses and heels on my feet. I shaved, not just the beard that I had grown to try to look less weak and more manly, but also what there was on my legs and all my other body hair including all around my cock. My messy crop of sandy blond hair, I grew out until it was shoulder length.

Of course, these changes in my appearance were noticed by my parents and their friends who hired me to babysit at their houses, but nobody ever suspected the reason for my new clean-shaven face or hairstyle. I was confident that my growing secret kinkiness was completely safe from being discovered. I only ever engaged in my fantasies of becoming a cute girl when I was in a house totally alone except for fast asl**p c***dren. I had convinced myself that whatever I did then it was alright provided nobody ever found out about it. And maybe it would have been had I never been found out, but that state of affairs was not to last.

It was another Friday, which meant that Joe and Sara were off to a party, and once again I was around at their place to babysit the k**s, which, of course, really meant swanning around the house in a skirt and heels, imagining myself as the stereotypical cute teen girl babysitter.

My body was already soft and shaved from earlier on today. All I needed to do was cast aside my boring masculine clothes and slip into something altogether sexier. Fortunately, Sara had just the sort of thing I was looking for. I was pleased that she tended to dress younger than her age as I really wanted to go for a cute teen look. Rifling through her underwear drawer, I now knew exactly what I was looking for, having got to know it pretty well by now. A simple, virginal white lace thong and a matching bra were all I felt my pretty teenage persona needed. The thong felt amazing as it encased my already semi-tumescent cock and ran up my ass crack. I stuffed the bra with tissues to give me a little bit of a chest. Fortunately, I felt a slightly flat chested look made me look cute and younger than I actually was as a guy.

Next, I found a little grey pleated mini-skirt. Being slightly taller than Sara made the skirt even shorter on me, barely swaying at thigh level. I slipped the skirt on and gave a little twirl. I loved the feeling of having my long, slender legs exposed and easy access to my awaiting crotch. On top, I found a cute pink sweater that just fit perfectly, clinging tightly to my slight curves and narrow waist. For shoes, I chose a simple pair of four-inch heels that served to enhance the shapeliness of my feminine calves and thighs.

I sat before the mirror and went through Sara's makeup. This was the first time that I had done this and I was excited by the chance to make myself even more feminine than usual. I chose a simple touch of blush and mascara, wanting to make my pretty little babysitter self have a youthful innocent look about her. My lips I painted with a glittery pink lip-gloss that drew attention to my cute mouth and seemed more what a teenage girl would wear rather than a thirty-something mother of two. Finally, I styled my hair into two blonde pigtails either side of my face.

I looked in the mirror and it wasn't me looking back at all. No, it was Cassie, the cute teen in her tight sweater and short skirt. The hot babysitter who all the dads like to fantasise about but know they can never have. The one that looks so cute and innocent but has a dirty, kinky mind beneath that sweet exterior. I could barely believe that I could pass for that girl, but the evidence was right in front of me. I was Cassie. I was the cute fantasy girl!

Well, the very thought of that was getting me pretty hard, as was the feel of the lace thong around my cock, not to mention the short skirt. I began to rub my dick through the material of the skirt and my panties. I was concentrating intensely on the reflection, watching innocent but naughty Cassie rubbing herself through her skirt.

I licked my glossy pink lips and gave myself a naughty smile in the mirror. I lifted my skirt and pulled my cock out of my panties. A little drop of pre-cum glistened on the swollen head of it. I wrapped my hand around the shaft and began to stroke, letting out a little sigh of pleasure; my pretty, girlish face looked a sight with my mouth open, gasping in sexual anticipation.

And that was the moment when I heard the front door slam shut downstairs. Worse, I heard footsteps running up the stairs at quite a pace. I slid my cock back into my panties, or what I was rapidly remembering were in actual fact Sara's panties, and dropped my, or her, skirt back into place, smoothing it down and trying to cover my bulging arousal. I knew there was nowhere I could hide quickly enough, if anyone came through that door, I was discovered. My only hope was somehow to pass this off as a joke or something, anything but revealing how turned on I was by being so girlish.

As that thought passed through my head, the door opened and Joe burst into the bedroom. He staggered a little, obviously having d***k a fair bit, and did something of a double take when he saw me standing there, taking a moment to process who the hell this cute teen babe in his bedroom could be. After a moment's open mouthed staring, he recognised his wife's clothes, remembered who he had hired as a babysitter and put two and two together. All this time, I was just standing there paralysed with fear about what was about to happen.

"I came back from the party early," Joe said, by way of some explanation. "Sara was having too much fun without me." He paused and then ran his eyes over me again, this time his expression was not confusion but amusement and, I thought, I detected at least a hint of desire. "And it looks like you've been having some fun of your own, eh?"

"Um, yes, sir," I stammered, blushing red in a way that, had it not been for the panicked situation I would have been quite proud of, it only served to heighten my innocent teen look.

"Ha ha, sir, I like that." He leered at me, lust was definitely in his eyes now. "And what do I call you, sweetness?"

"Ca…Cassie, sir," I stammered again, in a high pitched girl's voice.

"Well, now, Cassie, there's no need to be nervous," he said, taking a couple of steps toward me so he was just a couple of feet away. "Me and your dad have been friends since you were just a little girl. And sweet little Cassie's been such a good babysitter for me and my wife. Maybe she deserves a big, thick reward."

There was no doubt about it now. He was coming onto me. My dad's good friend had caught me dressed as a girl and instead of reacting with anger, he was propositioning me. My dreams of being the cute, innocent teen babysitter girl all the dads fantasised over had come awfully true and now I would have to deal with the consequences. I was blushing bright red now and it wasn't just fear. I had to admit that the whole idea of this situation, one that, except for the cock beneath my skirt, could be right out of a porno movie, made me quite excited.

Even though a month earlier the idea of sex with another man would have seemed almost worse than anything, now it seemed to me a whole lot better than that man revealing I liked to sneak around the neighbours' houses dressing in their skirts and panties. It wouldn't just be the cushy job and extra cash that would suffer if that got out. Imagine how my parents would react, or my friends. These fears flashed through my mind, but part of it was just me rationalising the way I knew I was about to behave. I had taken on the persona of Cassie, the cute teen temptress, and I couldn't escape it now.

"Do you find me attractive, Cassie?" Joe had said, moving even closer to me. "You know I think you're such a pretty girl."

"Yes, sir," I gasped, nervously.

The truth was that I was starting to think he wasn't looking so bad. His body was in great shape for a man in his mid-thirties, he was toned and built and part of me was starting to get unhealthy thoughts about what he looked like beneath his tight shirt and jeans.

"Yes, you find me attractive, Cassie?" he smiled, again running his eyes with an a****l lust over my slender young body, "Well, how about a kiss for your dad's old friend?"

Before I could answer, he took me by my shoulders and pulled me to him. He pressed his lips against mine. Up until that point, I was still in two minds about how I was going to react but as his lips touched mine, I just melted into the kiss. I let out a sigh of pleasure and completely gave in to my desire to be Cassie the teen babysitter and to be kissed by my older employer. He pulled me close in to him until his hard body was pressed against mine. I felt so small and soft in his manly embrace. It just felt right to let him slide his tongue into my mouth and I offered no objection as his hands ran down to my bare thighs and began gently to stroke them. Each touch felt electric, my skin was alive with desire. I knew as the kiss broke that my body would do anything he wanted now.

He stepped back and stripped out of his shirt. His chest was really ripped, his gym-sculpted muscles beautifully defined. Then he slid his jeans to the floor. He was completely naked before me, holding his cock in his hand and jerking it off. It was only semi-erect but it was already pretty long and thick and it was only getting bigger as it got harder. I knew just from looking at it that I wanted it. My girlish transformation was complete. There was no denying that all the dressing up, playing, masturbating and eating my own cum, had all been building up to this.
89% (27/3)
Categories: FetishMasturbation
Posted by Acebottom
4 years ago    Views: 3,117
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1 month ago
mmmmhmmm ;)
3 years ago
Another great chapter! I am still hard from reading it. Really can't wait to read the next part! Awesome Cassie
4 years ago
4 years ago
You always write such fascinating stories! Looking forward to the next chapter.
4 years ago
cant wait for part 3
4 years ago
4 years ago
Amazing. Part 3 and more I hope.
4 years ago