The Babysitter

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 naïve 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.