This story was a request from a reader. I don't usually do them, but I thought I could do something with the idea. So, thank you for the suggestion :)
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 children and all that they needed of me was to be in the house while their children 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 animals 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 far fetched 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 young 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 possibly, 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.
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 babysit 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 asleep children. 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 kids, 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 all together 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 liked 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 where 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 drunk 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 animal 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.
"Have you ever been with a man, Cassie?" Joe said.
"No, sir," I replied, blushing sweetly once more, "You're the first."
"Would you like to get down and suck me, sweetness," he went on.
I dropped to my knees instantly. Close up, his cock was even bigger. It was so thick and had throbbing veins sticking out. The head was just emerging from the stretched foreskin and was already glistening with translucent pre-cum. As I reached up to touch it, it felt warm, alive and growing, alert to my slightest attentions. It thrilled me to have such a visible affect on this hung guy and that spurred me on even further.