The Babysitter's Secret Ch. 02

Over a week had passed since Scott had caught me dressed in lingerie, face-fucked me and left me covered in cum on his parents' bed. It was clear he hadn't told his parents or mine that the 18yo neighbour they relied on to babysit Scott's younger brother, Timmy, was a crossdressing sissy. That came as a huge relief, even if my heart still stopped beating every time I'd seen Mr or Mrs Stevens since.

I hadn't seen Scott either. After he wiped his cock across my cum-covered face, he'd left the room and disappeared. He had moved out months ago and I had no clue why he had driven over to his parents' house that night. At some point I knew I would see him again, even if it was only a glimpse when he visited his parents, and I couldn't help but feel a certain amount of trepidation. Would he say anything to me about what had happened? Would he be angry with me? Would he want to do it again?

"Alex?" Mum called from the other room. I was finishing breakfast at the kitchen bench.

"Mrs Stevens just sent me a message," she said, walking in holding her phone.

I looked up, anxiety rising at the mention of her name. "Oh?"

"She's just wondering if you can look after Timmy again tonight. Can I tell her yes?"

"Oh... sure, tell her it's no problem."

"Great. Looks like it's only for a few hours, not overnight like last time. Coffee?"

"Yeah, thanks," I replied. "Hey, do you know why they don't get Scott to mind Timmy?"

"Probably because you live next door and he lives, what, over an hour away?" Mum said, grabbing two mugs from the cupboard. "Besides, I think they see you as a better role model than Scott. No, you are. I'm just being honest. We all know Scott's not big on responsibility."

"Yeah... I know." Scott was five years older than me and we'd never been friends, just neighbours who'd say hi when we saw each other and that was about it. I knew he'd had a bit of a reputation as a bad boy at school. As far as the details went, I wasn't sure. I remember back then there was always talk of some of the seniors smoking pot and having sex, like it was some kind of club? I preferred to keep my distance from such rumours, but I did wonder whether Scott could have been involved.

"You basically get paid to look after a sleeping kid," Mum said, handing me a mug of coffee. "It honestly sounds like a dream job."

Later that evening, I found myself once more sitting on the Stevens' couch and idling scrolling through their Netflix. Timmy was tucked up in bed and I had the place to myself. My dream job, I laughed, remembering Mum's comment from that morning. Like last time, I had brought some clothes in my bag, but I was hesitant to put them on since I didn't know when Mr and Mrs Stevens would return home.

The noise and lights from their car would provide warning of their arrival, and maybe I'd have enough time to quickly change back into my boy clothes before they opened the door, or at least I could rush to the bathroom and change there? It was still a risk, though. and after last time I wasn't sure if it was a risk I was prepared to take.

Part of me I knew was excited at the prospect of Scott catching me again, yet surely the likelihood he'd drop by unannounced was incredibly slim. More likely, I'd be caught by Mr and Mrs Stevens, and that didn't bear thinking about. My role model days would be over, that's for sure.

Temptation got the better of me. I opened my bag and withdrew the panties I'd brought. They were rose pink boyshorts with a delicate floral lace pattern all over and two tiny pink bows at the hips. I'll just change into some panties, I thought, and leave it at that. If someone comes home, I'll get the thrill of knowing I'm wearing pretty pink lace under my boring boy clothes, and they'll be none the wiser.

Decision made, I slipped out of my jeans and boxers and quickly slipped in to my panties. With my jeans back on, I wriggled my butt on the couch, enjoying the tight lace as it squirmed between my cheeks.

Feeling increasingly horny, there was no way I was going to be able to concentrate watching something on Netflix. So I pulled out my phone and searched my favourite porn site. I typically watched straight porn and recently I found what I enjoyed most was imagine myself as the girl in the clip. Gangbang was the category I always browsed first. Thinking about being surrounded by men, all rock hard and lusting after me, was a huge turn-on. Occasionally I'd watch gay or trans porn, too, but my tastes there were more particular; they had to feature a younger, submissive sissy or transgirl and an older, dominant man. I still preferred the traditional gender roles, I guess.

Tonight a few clips caught my eye. One had a cute white girl delivering pizza to a group of black guys watching the game--I was pretty sure I knew how that one ended. Another had a woman dropping her car in for a service, and discovering the mechanics were more interested in her servicing them instead. I think I'd watched it before, actually. Eventually I hit play on a clip where a schoolgirl was caught spying in the boys' locker room after gym class. I slipped my hand inside my jeans and stroked my cock through the lace as I watched her suck their cocks.

A crazy thought crossed my mind: I wondered if this sort of thing ever happened at high school. Those rumours about the seniors and their sex club, was this what they got up to? Did Scott do this? I mean, I'm sure he had sex with some of the girls at high school. He was on the football team, that's what they do, right? But did he and his friends get their cocks sucked by one of the girls? Did they gangbang her in the locker room?

I'd finished high school only a few months back and I still thought about it frequently, all the things I could've done differently, the things I thought maybe everyone else was doing but I'd missed out on. It didn't take a great leap of imagination to start thinking I was the girl in the clip. Dressed in the stereotypical sexy schoolgirl outfit of red tartan skirt and white blouse, I'd tiptoed into the locker room while they were all showering, hoping to catch a glimpse of the cocks on the boys I'd sit next to in class. But one of the guys had been late off the field and found me hiding near the entrance, my hand down the front of my panties.

Protesting my innocence was futile. He dragged me inside and told everyone what I'd been doing. I was on my knees, surrounded by six guys in various states of undress; some fresh out of the shower, water dripping off their muscled bodies, others wrapped in towels. I knew what was coming next. Six hard cocks were suddenly pointed at my face, just inches from my now salivating mouth.

In the video, the girl was holding two cocks and sucking a third, switching between them frequently until she'd tasted all six guys. Back in the Stevens' living room, I slipped my stiff little cock free of its lace restraint and started to stroke it. Soon I stopped imagining that I was the girl in the clip and started picturing myself in this scenario. In my mind, I realised one of the guys was Scott, and I was sucking his cock again. Next to him were some of the other guys who'd been in his year at school. They were calling me a slut and telling me how much I must love sucking dick.

My fantasy had now taken over completely. What was happening in the video no longer mattered; I was lying back on the couch, jerking off my lace-clad cock, eyes closed, lost in a reverie of hard teen cock. On the locker room floor, I was completely at their mercy. I wanted Scott and his friends to use me however they wanted, to force themselves on me, to fill my holes, to fuck me like the little sissy slut I now so desperately wanted to be.

Light flooded the living room.

"Fuck!"

They were home. The room went dark again as the car stopped in the driveway and its headlights were switched off. I squeezed my still hard cock back into my panties and awkwardly zipped up my jeans. I quit the browser app on my phone and locked it. I closed my bag and shoved it under the coffee table. After one more frantic look around the room, I tried to look as casual as possible, just chilling on the couch watching TV.

"Hi, Alex!" Mrs Stevens called from the front door.

"Hi!" I replied.

"Timmy give you any trouble?" Mr Stevens asked as he followed his wife into the living room and put his briefcase on the table.

"Nah, not at all. He's fast asleep. Want me to leave the TV on?" I asked, grabbing the remote and getting ready to leave.

"Sure," said a new voice behind me, causing me to freeze. Scott walked out of the kitchen. He must have come in via the back door. A smirk flashed across his face as he sat down on the couch next to me. He looked over his shoulder to check his parents had left the room. "We didn't interrupt you, did we?"

"No..." I said. The smirk on his face told me he knew I was lying. "I was just watching TV."

"Right. Of course you were." He spied my bag under the coffee table and grabbed it before I could move. "Let's see what's in here..." He opened the bag and pulled out my boxers. "Huh... interesting..." He held them up. "I wonder why these are in your bag and not, I dunno, on your ass?" That cocky smirk turned into a leer, and he laughed to himself, putting the boxers back in the bag. "And what's this?"

My heart was pounding as he pulled out the pink babydoll that matched the panties I was wearing beneath my jeans. I was too stunned to speak, certain my cheeks had turned the same shade of pink as the lingerie. What if Mr or Mrs Stevens came back into the room? What would I tell them? What would they say? What would Scott say? And even if they didn't return, why was he doing this?

The last question was easy to answer. He was clearly enjoying the power he had over me. He was getting a kick out of teasing me in the same way he'd been turned on by catching me all dressed up last Saturday. The real question was what did he plan to do with this power? And how far would he take the teasing?

Scott tossed the babydoll at me as Mrs Stevens walked back into the room. Without thinking, I snatched it out of the air and shoved it under my shirt.

"Thanks so much, Alex," Mrs Stevens said, handing me a few twenties. "We're going to have dinner now, but you're welcome to stay and watch TV, if you like. I know, I'll bring you out some dessert. Would you like that?"

"Uh, actually... I really shoul-" I started to protest before Scott cut me off.

"Great idea, Mum, we'd love some dessert," he said. "Extra cream for Alex!"

I shot him daggers as Mrs Stevens left the room again.

"Come on, I know you just love cream," he leered. "All that sticky white stuff. You can't get enough."

He was still laughing at his joke when he leaned over and tried to grab the babydoll I'd hidden under my shirt.

"You gonna wear this? Go on, put it on."

"What? No, I can't!" I insisted, trying yet failing to push him away.

"I bet it'd look great with what you're wearing under here..." His hands moved from under my shirt to undoing my jeans, revealing the pink lace of my panties. "Holy shit! You're already leaking, you little sissy. I'm here giving you shit and you're turned on by it."

I could hardly deny it. My cock was hard again, pointing upwards as it strained at the lace, a damp patch clearly visible around the tip. But it didn't mean I wanted him to bully me into dressing for him. Certainly not when his parents were right there in the other room. Maybe if they weren't here... my mind briefly flashed back to the video I was watching just minutes earlier, images of being on my knees in front of Scott and his friends, all those cocks, Scott's big hard cock right in front of me, and how I'd tasted it and sucked it just a week or so ago. No, but his parents are here--they're right there, through that door, in the kitchen--and I can't. Scott, however, had other ideas.

"Ok, here's what you're gonna do," he said, finally grabbing the babydoll and stuffing it back into my bag. "You're gonna sit here and you're gonna eat dessert--with extra cream--and then you're gonna go to the bathroom and put this on under your t-shirt," he handed me the bag, before continuing. "Then you're gonna say goodbye to my folks and meet me out front. Got it?"

I looked at him.

"I said, you got that, sissy?"

"Yes... I've got it."

"Good."

Dessert arrived a bit later, a chocolate pudding covered in cream, and only served to encouraged Scott's relentless teasing. He kept asking if I was enjoying the cream and trying to flick dollops of it onto my face. He stuck his finger in my bowl then asked me to lick it off, which I did, not wanting to piss him off. Next time he did it, he smeared it on my cheek when I went to lick it. "Now that looks familiar," he laughed.

I wasn't entirely sure why I was playing along with him. Of course, it felt like he had all the power. He was older than me, bigger, stronger, and that was intimidating. And he knew a secret about me, something that no one else knew. I couldn't even begin to imagine what my life would be like if he told anyone--his parents, my parents, anyone. We didn't have any mutual friends that I knew of, but there were plenty of people who knew both of us from school or just around the neighbourhood. I'd be mortified if any of my friends found out I like to dress as a girl.

At the same time, I knew I now had a secret about him. That he'd had his dick sucked by a guy. And not just any guy; he'd had his dick sucked by his 18yo crossdressing neighbour. He'd cum on another guy's face. That was something Scott surely wouldn't want his friends or family finding out about, was it? Of course, I couldn't blackmail him without incriminating myself. He could easily tell people he'd caught me dressed like a girl and the rumours would haunt me forever. If I tried to tell anyone that Scott had been sucked off by another guy, I didn't see how I could do that without revealing the other guy was me.

So I played along. I agreed to his plan to change in the bathroom and then meet him outside. And I put up with his teasing and licked his finger when he told me to. I didn't really feel like a had a choice.

Part of me also knew that I liked it. Perverse as it was, I enjoyed the attention he was giving me. It had been exciting to see how aroused he was last Saturday, and how the sight of me in lingerie had been responsible for turning him on. I'd loved the feel of his cock in my mouth and the taste of it on my tongue. I'd loved how he clearly enjoyed himself. And it was exciting to think that everything he was doing now--the teasing, the jokes, the smirk, the plan--seemed to strongly suggest he wanted a repeat of Saturday night.

Yet I realised there was more to it than that. The way he wielded his power over me was exciting in and of itself. When he put me down and insulted me, I felt excited not just because of the attention, but because I enjoyed feeling humiliated by him. When he called me a sissy, it made me want to be more of a sissy for him. When he told me what to do, it made me want to obey him. When he flicked cream on my face, I wanted him to do it again for real.

"Out the front. Five minutes." That was Scott's parting command. Upstairs, in the bathroom, I put my bag down next to the sink, removed the babydoll and pulled my t-shirt up over my head. I slipped the lingerie over my head, letting it fall to its full length just above my hips, before putting my t-shirt back on. It wasn't very comfortable, the loose babydoll was all gathered up in awkward bunches, but looking in the mirror it didn't appear to be immediately obvious what I was wearing underneath. I left and went back downstairs.

"Bye!" I called, poking my head into the kitchen where the Stevens were still pottering about.

"See you, Alex, and thanks again," said Mr Stevens.

"Oh, see you!" I heard Mrs Stevens echo as I made my hasty retreat.

Outside, I couldn't see Scott at first. Then I noticed him sitting in the driver's seat of his parents' car. Did he ask me to wear the babydoll just because he knew I would? And now he was leaving, having had his fun tormenting me?

"What are you doing?" I asked, standing at the car window. "Are you going back home?"

"Shut up and listen," he said firmly, but not in a threatening way. "Stop asking questions and do what I say."

"Um, ok."

"Take off your t-shirt and jeans and get in the car." He could sense I was hesitating. "You heard me. Do it."

Glancing around, the street was quiet this time of night. The Stevens' front yard was dark enough that no one would notice me stripping off unless they were directly in front of the house. The lights were on and my parents were home next door, but I felt sure unless they came outside they wouldn't see me either. I kicked off my shoes and socks then peeled off my jeans and t-shirt, clutching them close to preserve some small semblance of modesty. Scott opened the passenger door and I slipped inside.

Scott grabbed my clothes and bag and threw them onto the back seat. Sitting next to him wearing nothing but a pink babydoll and matching panties, I felt completely exposed. The darkness inside the car disguised what my hands couldn't, but they couldn't hide the lascivious smirk Scott had fixed to his face the entire time. Seeing that expression on his face made me feel like such an idiot. Yet here I was following him into his car, obeying his every word, and my little cock was getting hard again.

"Alright, let's go for a drive," Scott said, backing the car out the driveway. We were a few blocks away before I managed to ask where we were going. Scott shrugged and reminded me not to ask questions. "Just sit there and look pretty."

I blushed. Did he really think I was pretty? My stiff cocked throbbed with delight. I glanced at Scott sitting there behind the wheel, his elbow propped on the open window, the passing streetlights bringing him out of silhouette every few seconds. Even in the dim light, this was the longest I'd studied his face. He was handsome, undoubtedly, maybe better looking than I'd realised. Or was it just because he'd said I was pretty that I found myself seeing him in a new light?

We pulled up at a red light. Scott looked sideways and caught me staring at him. I smiled back, hoping I looked cute.

"Were you just checking me out?" he said, chuckling and shaking his head in disbelief. "Fuck, you're such a little sissy bitch, aren't you? You actually enjoy being treated like shit. Here, this is what you want, isn't it?"

Scott unzipped his jeans and pulled out his cock. It wasn't hard, but it was on the way. He reached over and grabbed my hair, pulling my head down into his lap. "Suck it, slut," he said, as the lights turned green and the car pulled away. My body was twisted awkwardly, but I quickly forgot all about the inconvenience as I took his cock in my mouth and sucked him with hunger.

We were cruising now along the highway, my head bobbing up and down in Scott's lap. He kept one hand on the wheel while the other crept down from the back of my head, along my back, to my ass. He squeezed my cheek, eliciting from me a brief sigh of pleasure. With surprising delicacy, his fingers traced the crack between my cheeks, the flimsy lace the only barrier between him and my little hole. I moaned, louder this time, my ass squirming with excitement at the touch.

Shortly, we pulled off the highway and a few minutes later came to a stop outside a small apartment building. Scott lifted my head off his cock, a thin strand of my saliva glistened in the dark as it trailed from my lip to his shaft.

"We're here," he said.

"Where?"

He gave me a sharp look. "No questions. Get out."

Scott grabbed my bag from the back and shoved my clothes inside then lead me to the main door. Again I was acutely aware of just how under-dressed I was--the babydoll stopped at the top of my hips, doing nothing to cover my ass. Two cars drove past, but neither slowed down or stopped. I probably looked like any other girl in a way too short dress, stumbling home with her boyfriend.