The Babysitter free porn video

The Babysitter by Richard-to-Rachel 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. Without a second thought, I leaned in closer, stuck my tongue out and got my first taste of cock, licking a spaghetti string of pre-cum from his swollen purple cock head. Meanwhile, my hand began to stroke his shaft, still delighting in how I made it grow and the warm feeling of pleasure that flowed through it and into me. I began to lick up from the base of his shaft to the head, covering his dick with my saliva so it glistened like my glittery girly lips. "Mmmm, Cassie, you're such a cutie," Joe sighed, "Such a pretty little thing, so young and unspoiled. Uhhhh," he gasped, "Oh yeah, sweetness, lick my lollipop." "Ohhh, yes, sir," I sighed, licking up and down his fat warm cock. I could still see my reflection in the mirror and I had to say that it looked pretty hot. The scene was right out of a porno. There was the hung older stud, naked, his dick sticking out firm and erect while his young virgin teenage babysitter in her tight sweater, short pleated skirt and pigtails licked his throbbing hardness. And that pretty young wannabe slut was me! A guy who until recently had been nothing but an ordinary guy with no strange fantasies or kinks. "Mmmm, how about you give that meat a suck, huh, sweetness?" Joe moaned. Obligingly, I opened my mouth and took the head of his cock inside the wetness. Opening his foreskin with my tongue, I tongued his slit, all the while jerking his shaft with my hand. All this time, my own cock was getting harder and harder until it was almost as rock hard as his and tugging on the elastic of his wife's panties that I still wore beneath her sexy short skirt. I opened my mouth further and swallowed more of his hardness. Now, I began to bob back and forth on the length of it, really starting to get into it now, really enjoying my first cocksucking experience. Suddenly, I became aware that we weren't alone in the room. I heard a sound of stifled giggles and impressed snorts. I pulled my face away from Joe's crotch and looked around at the doorway. Standing there were three of Joe's friends. I knew them quite well, they were friends of my parents too, Rob, Gary and Daniel. I blushed an even deeper red at this latest humiliating discovery. My only comfort was that at least I didn't think they recognised me even though I babysat for their kids too. I guess I didn't usually look like a cute girl in a short skirt and pigtails then, and they didn't usually see me with their friend's thick cock between my lips. "I see you've got a new babysitter, Joe," Rob smirked. "And I can see why," Daniel responded, "She's a hottie. Where did you find her?" "And why are you keeping her such a secret?" Gary chipped in, "Why are you keeping her all for yourself, you naughty man?!" "Guys, this is Cassie," Joe indicated towards me, and I blushed further as I realised I was still stroking his hard dick even while all this had been going on, "Cassie, I'm sorry. I forgot that I'd come back with the other guys! I guess drink will do that to you. That and finding you in here looking like that. It was quite some distraction! Now, do you mind? I'm kind of in the middle of something here!" He finished, turning back to his friends. I opened my mouth and swallowed his cock once more, slurping all around his hard thickness, feeling his arousal getting even stronger at the thought of performing before his friends, showing off his masculinity by fucking the face of the pretty babysitter. I thought that the guys might leave but instead they came in and stood around watching. Before too long, they had pulled out their own cocks and were furiously beating them off as they watched me going down on more and more of Joe's rock hard manhood. I gasped and let the length of the big dick slip from my lips, giving it a couple of kisses before returning to lick it once more. The watching guys were now cheering me on as they stroked themselves. Meanwhile, I too was enjoying putting on a bit of a show. I had adjusted to the idea of people seeing me as my girlish self and was starting to appreciate being the centre of attention. "Ohhh, Mr. Dawson, your cock is sooo sexy," I cooed and sighed over my older hunky employer's hard manhood, "I used to be so innocent but now I can't help but want cock!" "Yeah, you go girl, suck him, slut!" Daniel cried out, watching. I gasped and opened my mouth to deep throat Joe's massive dick. I managed to take him all in and the sensation of being filled was incredible even though I could only manage it for a couple of seconds. Things were really hotting up now and I could tell that Joe was pretty close to the edge. It was no longer me sucking and slurping around his thick meat, he was the one thrusting into my mouth and all I could do was kneel there and take it, something I was increasingly happy to do! "Oh yeah, Cassie! Mmmm, that's it, sweetness. Suck on my big cock," Joe moaned, "You like a real man's cock, don't you honey? You're making this man feel kind of good. I haven't had a sweet young thing like you in a while. You're gonna make me blow my load pretty soon, sweetheart!" "Ohhh. - slurp - Please, sir," I gasped, "I want your cum - slurp - Cum in my mouth, Mr. Dawson!" I knew that it was coming and that just made me more eager. Now I was completely gobbling and slobbering all over his cock, while my hand cupped his balls, massaging them to bring that cum closer to my lips. I didn't care any more, I was just desperate for that cum, desperate to show what a good girl I could be. I wasn't to be disappointed. I felt Joe's cock twitching in my mouth, while his sighs and grunts got louder and more urgent until he could hold back no longer. "Oh God, Cassie, I'm cumming!" he gasped, "I'm cumming for you Cassie! Drink it down like a sweet little girl!" A stream of warm liquid hit the back of my throat and I swallowed it without even thinking. It tasted good and it felt good to be being used like this, to accept his thick spunk into my mouth. It felt like I was getting used like a real girl, a na?ve virgin having the older guys show her how its done, getting to drink their cum. As I swallowed, my mouth was quickly filled again until cum was running out the side of it. All the while, I held his huge cock in my mouth until it had finished spurting and became soft again. I turned to face the rest of the room with a big sticky grin on my face. Licking my lips, I tasted the last of the cum that Joe had fed me and then glanced around the three other guys. Each of them was eyeing me as hungrily as I had just been admiring Joe's cock. Each of them had their own hard member in their hands, willing and ready. And each of them was completely unaware that Cassie, the cute teen girl babysitter was really the male son of their close friend and had a proud and erect cock of her own just about concealed by the tiny skirt. "Well, well, Cassie, you've done a pretty good job on Joe there, you pretty little thing," Daniel grinned, "But now there's the rest of us waiting for our turn." I still knelt on the floor, a little worried that if I moved then it would reveal that beneath my skirt I was as aroused and excited as any of the other cocks in this room, but my eyes followed the three of them as they all stripped completely naked and all three walked towards me. They were all stroking their cocks as they manoeuvred themselves so all three were standing around my kneeling body. I suddenly felt very small, kneeling on the floor in my girly outfit with three large older men standing around me, waving their cocks larger than mine in my face. "Come on then, Cassie," Gary smirked, his cock was neither as long nor as thick as Joe's but it was still pretty sizeable and uncut with a huge bulging, glistening head and veins standing out along the shaft, "Show us what you can do, sweetheart." "Yes, sir," I smiled back at him, running my eyes over his cock, no longer feeling I needed to deny to myself that I wanted it in my mouth, "Would you like me to suck your cock." I pulled my sweetest, most innocent face, which could not fail to turn on an older guy as he looked down on the cute babysitter with her pigtails, tight sweater and short skirt. "Oh God, yes, Cassie," he said, "Suck me, baby." I opened my mouth and let Gary's huge head slide between my pink lips, swirling my tongue all around it, licking up the salty pre-cum. Meanwhile, I reached out with my hands and took the other two cocks, Daniel and Rob's and pulled them towards me, starting to stroke off their warm, hard shafts. All three guys began to moan with lust as they stood all around me, one feeding me his cock, the others getting my best handjobs. I couldn't imagine what the scene must look like to Joe as he watched his cute teen babysitter, a hot girl who only he knew was a guy, and the son of his friends at that, dressed in his wife's short skirt and sexy panties, knelt down in front of three of his friends' hard dicks, loving being the centre of attention for all these guys as hold as his/her parents. "Mmm, that tastes goooood," I sighed, letting Gary's dick slip from my mouth and turning to pull Rob's closer to me, kissing the head of it. This cock was longer and thinner than the others were but just as hard, "Come on, let me get a taste of you too." I started licking his lovely long shaft while Gary still continued to stick his cock in my face, rubbing his warm hardness against my cheek, smearing me with his pre-cum as he continued to stroke it. Meanwhile, my other hand was beating off Rob's thick throbbing beast, the biggest cock of the lot and the one I had left until last because of that. Switching again, I opened my mouth as wide as it would go and took Rob's thick meat inside it. I could only get about half of the length in before it hit the back of my throat, but I was quite happy to bob up and down on this length and this seemed to work pretty well for him too. "Oh yeah, baby," he grunted, "You might look all sweet and innocent but you suck cock like a dirty whore!" I felt myself blushing a deep red once more. It felt such a compliment to see how much I turned on these older, much more experienced guys. The feel of the hard cocks on my lips and tongue, entering the wetness of my mouth were really arousing to me. Almost as much as the sexy feminine clothes I was wearing. In fact, my own cock was every bit as hard and crying out for release as the one in my mouth, the one reminder that I wasn't the cute teen girl I was claiming to be. It was stretching out the fabric of Sara's white panties and my pre-cum was soaking them right through even onto the pleated skirt above. I wondered what the guys would think if they found out that I was packing meat just like there's. Would they want to hit me or fuck me? All this time I was behaving like a sex mad teen girl, on her knees sucking cock, I couldn't help but think about getting fucked. It would be the ultimate part of my transformation, for the hung guys to screw me like a little bitch and my virgin ass was starting too long to be penetrated. "Yeah, this sweet thing sucks cock pretty good for a beginner," Gary grinned, "But I want to get me a piece of her sweet pussy. I wanna fuck this cute babysitter slut!" Well, I guess there was no turning back now. I was about to find out what they thought of girls like me, whether I wanted to or not. Joe had been watching his friends sliding their dicks into my mouth for a while and now he came over to join them, still naked and still pretty hot, with his cock hard once more in his fist. He seemed a little worried about what was about to happen. After all, he was the one that knew I was a guy when I went down on him, so he was perhaps a bit panicked about his reputation. "Guys," he said, "I don't know. Maybe she's had enough. I promised I'd have her home by midnight. Maybe we should just let her suck us off. After all, what would our wives think? I mean, it's ok to get a quick suckfest from the teen sitter but to fuck her is much worse. Besides, she's a virgin down there, so we better take it slow." Unsurprisingly perhaps, that last comment had the complete opposite of the desired affect on the other guys. I looked around the three of them as they stood over me with their hard cocks in their hands eyeing me with even dirtier thoughts obviously written on their faces. I knew they were all picturing being the one to deflower this teen cutie and that thought just made them even tighter. "Joe, you mean one of us is going to be the one to take this sweet thing's cherry," Rob said, lustfully. "Yeah, you can't deny us the chance to be the first to have a crack at that sweet teen pussy," Daniel replied. All that Gary did was push me onto my back so I was lying on the floor, well aware that of my long, bare exposed legs and the tiny grey pleated skirts whose folds weren't doing much to hide how excited this conversation was making me. As Gary bent over my helpless form, I knew that he was about to discover my secret and yet I was still willing him on. Gary pulled my bare legs opened and manoeuvred his naked body until he was kneeling between my thighs. Meanwhile, Daniel had moved over so he was kneeling beside my face, his long cock still waving around tantalisingly close to my mouth. Daniel pulled my tight sweater over my head to expose my chest with my little teen tits inside the innocent white bra, or rather the stuffing I had used to suggest a just blossoming teen chest. Daniel began to massage my chest as he leant in and kissed my lips, but I could tell that he had begun to feel that there was something not right about my firm young breasts. At that same time, Gary flipped my grey pleated miniskirt up around my waist to expose my panties. There was no way of hiding it now, my panties were so wet with pre-cum that they were almost transparent, not to mention the bulging shape was kind of a giveaway. Still, just to be sure, Gary ripped off my panties and my hard cock sprang loose in his face causing him to jump back onto his feet with shock, even while Daniel turned to see what was not right about my body. There was a wide-eyed look of amazement on both their eyes, completely focused on my quivering member, as were Rob's. None of them, however, turned and left and none of their cocks got any less hard. "Holy shit, man," Gary was the first to speak, "She's not a fucking girl at all!" "Fuck, I knew she seemed familiar somehow," Rob replied, "That's not 'Cassie'; it's Chris, your usual babysitter." "Shit, Joe, you got a guy to suck you off?" Daniel said, also taking a step back, "You're not fucking queer are you?" "No, no," Joe said, although the raging hard-on he had from looking at me, a boy in a skirt and bra, implied otherwise, "I just couldn't help it. He just looked like such a cute girl..." "She is pretty sweet, isn't she," Gary said, eyeing me up still. "She's not a she, remember," Daniel, "That's Chris, Sean and Kathy's son. This is really gay." "Well, you didn't seem to mind when 'he' was sucking your cock," Joe replied, "And your dick's still pretty hard, so I guess maybe that makes you gay too." "Look, all that matters to me is that he or she or whatever looks like a total babe," Rob came in, "And she sucks cock like a real girl." "You're right, man," Gary agreed, "I'm horny, she's hot. I don't care if she's got a cock, I can still get a piece of that sweet teen arse." "Whatever," Daniel said, "But this is still really gay." But the others seemed to forget or not care that I was a guy and a guy that they knew well. Gary got back down between my long smooth legs. He grabbed me by the ankles beside my high-heeled shoes and pulled my legs open. Joe joined him kneeling beside me. As Gary pulled my legs open, Joe reached over and grabbed my hard penis. He pulled it up to give a good view of my tight little virgin arse. With his other hand, he licked his index and middle finger and slid it inside me. He began to finger fuck my arse while stroking my dick with his other hand. Rob, meanwhile, had moved around so he was kneeling by my head. As I gasped at the touch of Joe's hand on my cock and arse, Rob slid his thick dick back between my lips. I didn't have to do anything at all except lie back with my mouth wide open and let him slide his dick in and out, trying to open my throat and let the huge, thick meat fully inside. I didn't know which exciting stimulating thing to concentrate on as my body was flushed with sensations. There was a cock in my mouth but I was distracted by the fingers exploring my tight little arse. I had never had even a single finger back there, but now the idea that I was being opened up for a man's cock was a hell of a turn on. I could feel my arse clenching tightly around Joe's fingers but I tried to relax. After a while, Joe pulled his wet fingers out. My puckered little arsehole was wet and waiting to be filled. I let Rob's cock slip from my mouth for a moment so I could watch what the other guys were doing. My body had tensed up a little and I knew that wasn't good. I was filled with nervous excitement about what was about to happen, I knew that I would never be the same again. "Come on guys," I sighed, smiling sweetly, "Make a woman out of me." "With pleasure," Gary grinned. Joe, his hand still rubbing my dick with one hand, took his other, the one that had been inside my arse, and grabbed Gary's hard dick and positioned it at the entrance to my arse, so the head was rubbing along my arse crack as Gary held up my long legs. He lifted my ankles and pushed his shoulders against them. Levering himself like this, he was able to thrust the head just inside my sphincter. Even with that much inside me, I felt so filled up, I wondered how he was going to get the rest of the length inside me. It was painful, but it felt so good to give my body up to a hard manly dick that despite the pain I wanted more. Gary began to push up deeper into me and, with every inch, I began to feel more and more light-headed. It was still feeling pretty painful but I had a chance to grow used to the feel of the hard rod buried inside me. After allowing me to get used to it, Gary slid out and thrust back into me quicker than he had before causing my head to spin. "Oh God, yes!" I gasped, "Oh yeah, fuck me! Fuck my sweet girly virgin arse!" It wasn't like he needed much more invitation than that. Gary began to slam his cock right up inside me so the full length of the shaft was buried in my warm tightness. My arse clenched around his dick like a vice so any slight movement rubbed against me in my most delicately stimulated area and made my whole body quiver with the feeling of sexual completeness I had never had as a guy. "Mmmm, sweetness, your arse is so tight on my big cock," Gary moaned, "It's so good taking your teen cherry. You're gonna make me cum pretty soon." He began to slam his cock right into my arse and pull it out again, pumping faster and faster inside me, shaking my little teenage body about as he impaled me. There was nothing I could do except push my arse up to meet his thrusts. Joe was still stroking my dick with one hand and now was working on his own with the other. As I gasped and moaned with the pleasure of having my body truly penetrated for the first time, Rob slid his dick back inside my mouth so I was being taken at both ends. This was what all those weeks of dressing in sexy panties and then skirts and heels, of imagining myself in the role of the sexy teen babysitter, had been building towards. I had finally come to realise what I had been looking for. I had longed to feel what a real girl feels and now, lying on my back, in just my bra and heels with my skirt around my waist, legs spread and a cock in my arse and mouth, I could feel just like that. I had a very submissive side to my personality and it got a full chance to come out right now. I loved the feeling of giving my arse and mouth up to pleasure experienced men with hard cocks. Gary's thrusts deep and hard into my vulnerable virgin anus became more and more erratic. His gasps, grunts and groans were louder and more eager. I could tell that he was close to cumming and I longed to feel him shoot his warm load deep inside me, to fill me with his sticky seed. He pushed deeper into me, his full balls slapping against my round arse. "Oh yes, oh baby," Gary moaned, "I'm cumming! Oh God! Fuck. I'm gonna fill your virgin arse with my hot cum!" I felt my impaled arse filling up with sticky cum as Gary continued to moan and thrust until the cum started leaking out onto my thighs. Finally, he was finished and let his limp cock slide from my sticky anus. Almost instantly, he was replaced by Joe who slid his cock into the sticky mess left by his friend and instantly began to plough my arse. I had felt so empty for the moment after Gary pulled out that it felt even better having this second, larger, cock inside me. All this time, Daniel, who I thought had left after claiming that fucking me was too gay, had been watching the scene as I lay on my back being fucked, my hard cock sticking straight up out of my skirt. He obviously could no longer help his lustful feelings as he came back over to join us, stroking his long, thin cock. I had Joe's cock screwing my arse, while Rob was fucking my face. There wasn't really much space for Daniel. Joe, who was still stroking my dick even as he fucked my arse with his, pointed my engorged member toward Daniel. "Come and give a hand, Dan," Joe said, "She sucked you off, the least you can do is return the favour." "I already told you, that's really gay," Daniel responded, "I'm not some queer like you guys." "Yet you're really turned on watching us fuck this pretty little thing's arse," Joe returned back to him, "Either you like watching men fuck men, which makes you pretty gay, or Cassie here isn't a guy, which means it's not gay to go down on her." I didn't know if this was really the best logic but I wasn't about to disagree. It certainly seemed to work on Daniel's lingering doubts as he knelt down beside where I lay on the floor, sandwiched between his two friends' dicks, being rammed from one to the other. Joe passed my hard cock from his hand to Daniel's and Daniel began to beat me off with one hand while jerking off his own cock with the other. After a few minutes of this, he obviously got bolder as I felt a sensation other than warm hands wrapped around my dick. I could feel the wetness of a tongue running over my shaft and it made me quiver with pleasure. I turned my head so I could just about see what this insistently straight older man was doing with my cock even as I swallowed his friend's thick meat. Daniel opened his mouth to kiss my swollen cock head, but, as he did so, Joe slammed his own dick even harder into my raw ravaged arse and pushed my wobbling meat straight into his friend's mouth. Daniel gagged momentarily, but very quickly got the hang of swallowing my engorged manhood. He began to bob up and down on it in time with how Joe was ramming my arse so it was almost as if the one so-called straight friend was fucking the other's face through me. I was reminded of how well I had known these guys ever since I was a child; they were all my parents' good friends and all supposedly happily married. I wondered what their wives would think to see this scene played out for them. If they were to enter the room unexpectedly, how would they react to see all their husbands crowded around fucking the babysitter, dressed in just a skirt and bra, makeup smudged and pigtails out of place? And how much worse would their reaction be when they discovered that the cute teen girl babysitter wasn't a girl at all? When they discovered she was in fact a guy in girl's clothes, with his arse taken by their husbands' dicks and his own dick sucked by another of their straight hubbys. Things were really about to reach their climax now between me and my parents' friends. I could feel from the way both Joe and Rob and how they were fucking both my holes in an increasingly erratic way that they were both close to reaching their orgasms. The only question is which would be first. Meanwhile, the double penetration had set my body on fire and the feel of my cock in Daniel's mouth was nearly enough to send me over the edge. My body quivered with electric pleasure as one cock pushed inside my tight ravaged arse and another slid from my lips. It was the wet, thick monster in my mouth that exploded first, though. "Mmm, oh yeah, oh baby. Suck my cock, babe," Rob sighed, "Ohhh, yeah. Make me cum, Cassie. You want my cum, don't you, sweetheart? Want to drink it down?" And with that, I felt the second stream of warm, sticky cum to hit the back of my throat that night. Rob just kept on spurting his hot spunk until my mouth was completely full and the translucent juices were leaking from my lips and over my chin. He pulled his cock out of my mouth and, stroking the shaft, shot another couple of streams of sticky, salty juice over my face. It felt so good to be covered in this man's cum, to hold the tasty juice in my mouth and feel it covering my face. It felt like I was a real hot girl to be able to create that reaction in a guy. As I grinned and swallowed the cum in my mouth, eagerly licking my lips as I did so and showing the other guys how much I enjoyed it, I saw Joe was about to blow his second load of the night. He pulled his dick out of my tight, newly fucked arsehole. It was glistening with Gary's cum, which he had picked up from inside me. He began to jerk himself off over me as his cock began to shoot its sticky load. Daniel, meanwhile, still had my cock buried in his mouth and, as Joe aimed to shoot his load across my defiled once virgin teenage body, he ended up shooting a lot of his cum instead across his friend's face as the latter swallowed my meat. Surprisingly, the cum shower did nothing to stop Daniel from going down on my own dick and the showering of his friend in cum did nothing to stop the incredible force of Joe's ejaculate. Soon, both Daniel's face and my chest were sticky with milky juices. "Ohhh, sir, you're a cumslut just like me," I gasped, incredibly turned on to see Daniel's face covered in spunk as he eagerly sucked on my trembling dick, "Well, get ready for some more!" My cock began to spurt and fill the older man cocksucker's waiting mouth with my own cum as my orgasm shook through my body from my sticky, well fucked arse to my cum filled throat. My cum was leaking from his mouth and still there was even more to come. Daniel took his lips from my cock and came over to my face, stroking his own hardness. I continued to cum over my body and over my employer's little grey mini-skirt, I would never be able to give that back to her! Meanwhile, Daniel began to let his cock shoot another load on my face and chest, making the white bra I wore about as useless to return to its owner as the skirt. Finally, when both of us were spent, he bent over my exhausted body as I lay on the floor and kissed me deep on the lips, pushing my cum that still filled his mouth back down my throat and licking his own from my lips. The three guys who had come home with Joe then turned and put their clothes back on. After exchanging some words with Joe, they then left. All this time I lay back on the floor in the stained skirt and bra, heels still on my feet, my makeup smudged and my blonde pigtails sticky with cum. My girlish outfit was a little dishevelled but the experience that I had just had made me look at myself more as a girl than ever. No, not quite a girl, no my cute, innocent teen babysitter self had had her innocence taken from her, had been well and truly fucked in all her holes, I now saw myself as a woman. Thinking this happily, I basked in a post-orgasmic glow for some time until Joe brought me to my senses. His wife, Sara, would be expected home any time and did not expect to see her male babysitter dressed in her clothes and soaked in her husband's cum. I cleaned myself up as quickly as well as I could and put my male clothes back on. As I was leaving the house, however, Joe gave me a significantly thicker pile of banknotes than was my usual babysitting rate. "You're such a good little babysitter, sweetness," he said, "You've really earned this little bonus. And all my friends were very satisfied. They'll be recommending your services around." Well, I guess that would show all my friends who said I couldn't make any real money for babysitting! THE END