The Babysitter: Chapter One

Sometimes I guess it's hard to find ways to make a bit of extra money when you're home from college for the summer. It certainly wasn't easy for me looking for work. That's why I found myself doing a bit of babysitting in my spare evenings. I know, it's the kind of work that you'd expect from a teenage girl, not a nineteen-year-old guy who should be out living it up at nights. But, it was easy work and it was money.

My parents were very young for the parents of someone my age, I sometimes found it hard to believe that they were younger than I was now when they had had me. This meant that they had a number of friends with young c***dren and all that they needed of me was to be in the house while their c***dren slept. I could just watch TV, eat whatever food they had in the fridge and drink their alcohol. It was a pretty ideal job really, all things considered, even if it did make my friends mock me a little.

It had one other advantage as well. I have to admit that I was a nosey, curious kind of guy, and I loved the idea of looking around the houses of my parents' friends and going through all their things, even their private things, and getting a greater impression of what they were like. Naturally, it wasn't long before I discovered that the most interesting place to snoop around was in the wives' panty drawers.

I've always loved women in sexy lingerie and I couldn't help getting turned on as I went through the underwear of my parents' closest friends. Now, whenever I saw them I couldn't help but imagine the sexy satin, silk and lace that I knew lay beneath their clothes. Meanwhile, when left alone in their homes, I loved to touch it, feel their sensual softness and inhale their feminine scent.

One evening, I was babysitting at Joe and Sara Dawson's house. They were a couple in their mid thirties with twin daughters aged four who had long since been put to bed. Joe and Sara still liked to think of themselves as young party a****ls and still liked to date in bars and clubs. They both kept in pretty good shape too and could probably convince as being a bit younger than they were. I knew that Sara's wardrobe was definitely that of a much younger good time girl. I certainly knew that she had that kind of underwear.

I knew that because I was right away inside her underwear drawer as soon as I heard their car pulling away. It was a treasure trove of sensual feminine delights. I sighed as I ran my hands through all the sexy panties. I knew that this was really wrong but I couldn't really help myself. Besides, I was basically alone in the house and nobody would ever know.

I selected a pair of pale blue lacy boy shorts and took them from the drawer. As I buried my face inside the panties, I loved the feel of the lace on my face. I could feel my cock already getting hard at the thought of the panties. Looking around nervously, even though I knew there could be nobody there, I decided to take things to the next level.

I lay back on Joe and Sara's bed and pulled my pants down around my ankles. My hard cock sprang out. I held the panties in my hand and then began to stroke my cock, rubbing the sexy lace against my hard throbbing flesh. I gasped at the touch of the older woman's hot undies. Before I could really stop myself, I found myself cumming, shooting a hot, sticky load all over my hands and Sara's sexy blue panties.

I cleaned myself up by having a shower and then tried to think of what to do with the soiled panties. That's when the thought came to me. I could wear them! Underneath all my other clothes. It wasn't too farfetched to move from my love of the look of the sexy panties and the feel of them on my firm member, to desiring to wear them.

I got hard again pretty quickly when wearing the sticky, soiled panties. If anything, the feel of my cum on the lacy material against my skin made me feel even more aroused even as I was a little embarrassed by what I had done. I tried hard to forget and let my erection subside before Joe and Sara returned, but it was hard to do when wearing the sexy undies.

That night, I went home still wearing the panties of my employer and feeling slightly dirty but even more sexy. Back home, I was able to wash the panties and hide them away until the next time I was hired to babysit for Joe and Sara and then I could put them back. I only hoped that Sara wouldn't notice that her panties were missing in that time.

Fortunately, Joe and Sara went out pretty regularly, and it only took until the following weekend for them to ask me back to watch the girls and the house. Naturally, the only way I could get the panties back into the house without my parents or Joe and Sara noticing was to wear them again under my other clothes. This was something I didn't regret at all. Ever since the last week I had been thinking about the feel of the panties against my skin and, as soon as I put them on, I began to get hard again.

With Joe and Sara having left for the evening once more, I went back up to their bedroom and stripped out of all of my clothes except for Sara's sensual blue lace boy shorts. I was somewhat regretful about having to take them off. I looked down at my arse in the cute baby blue lace. My legs were long, slender and hairless and, with the panties on, they looked just like the legs of a hot girl, with her pert arse in sexy panties. That thought made my cock twitch again, making it that little bit harder.

The thought occurred to me that I had plenty of time yet before Joe and Sara returned from their night out. I didn't have to take the sexy panties off yet. In fact, I could go through the lingerie drawer again and find something further to cover my body. I longed for more soft, sensual girly fabrics against my tingling skin.

Before I could really think about it rationally, I was already pawing through Sara's lingerie selection, naked except for a pair of her cute panties. I quickly found exactly what I was looking for, a skimpy little babydoll in the same baby blue as the panties. It was made of soft thin satin and opened at the front. The cups were frilled with blue lace like that on my panties. As I held it in my hands and felt the soft satin and sensual lace, I couldn't help letting out a little girlish squeal of delight.

I didn't have to think about what I was doing: as quickly as possible, I had put the babydoll on and was enjoying the feel of the soft satin on my chest and brushing against my arse and the tops of my thighs. This must be how Sara feels all the time in this underwear, I thought enviously, as my cock began to create quite a tent in my panties. I wondered how she ever got anything done, she must be horny all the time.

I couldn't pretend that it was just the sensual feel of the feminine fabrics on my male body that was turning me on. I was starting to imagine what it felt like for a woman in this lingerie. Not only that, I was running my eyes admiringly down my body and picturing it as a woman's body, picturing myself as a woman. I had always been slight and thin.

I had always regretted not being as masculine or muscular as the other guys, but now I couldn't be happier with how my body looked as I looked down at my soft, hairless slender form in the girly babydoll, with my long legs poking out beneath. Hell, I had the kind of cute, girlish body I liked to see in a woman!

I couldn't help myself any longer, any thoughts about how weird and wrong it was to sneak into my employer's bedroom and try on her sexy underwear had completely gone from my head. I was hot and horny and I just had to touch myself. I rubbed my dick through the thin lacy material of the baby blue panties. My other hand slid inside the cups of my babydoll and caressed my nipples, imagining I had a small pair of perky teenage breasts.

That was the thought that sent me over the edge and had me filling my panties once more with my warm sticky cum. It was the best orgasm I had had in ages, completely flooding right through my body and shooting out more cum than I had thought myself capable of, and I had achieved it all on my own. Well, just me and my new feminine alter-ego. Aside from the rock hard cock, I actually started to feel like a girl wearing all these pretty, frilly things.

Once again, I had completely stained Sara's panties. Not only that, but my hand was covered in the warm, milky juices of my orgasmic moment. I don't know what possessed me, maybe I still had it in my head that I was a sexy girl, but I was suddenly overcome with curiosity about the taste of my spunk. I took my fingers from my cock and stuck them in my mouth. It tasted pretty good, warm and salty. I couldn't help myself, soon I was licking my fingers clean, going down on them like a hard cock.

I stopped myself before I got hard again and filled my panties with even more cum, but by now I had crossed a line that there was no going back from. I had enjoyed dressing up in women's underwear, imagining myself as a sexy girl and eating cum. I had never considered myself as anything other than an ordinary straight guy but I guess that I would have to start thinking a little harder about that.
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Categories: FetishMasturbation
Posted by Acebottom
4 years ago    Views: 2,635
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10 months ago
I have been dressing up as a little girl since I first saw my friends mom all dressed up for work in blouse and skirt
3 years ago
Pretty hot story
3 years ago
Very hot story! Looking forward to reading more
4 years ago
4 years ago
hot story
4 years ago
Really hot.