The Babysitter

Today started off as a pretty normal Saturday. I was up in my room playing video games and Jenny, my babysitter, was downstairs doing something on her computer tablet; probably on Facebook or something. I was playing Mario Kart when she came upstairs in a huff and plopped herself down on my bed. I bounced slightly from the shockwave.

"Oh hey, video games." she said. "Can I join in?"

"Uhh, sure." I answered hesitantly. I had a sense that she was upset about something, but I wasn't dumb enough to ask her what was wrong. If she wanted to tell me what the problem was, she'd get around to it without my prodding. Jenny picked up the second controller and we played the game in silent for a few circuits. As it turned out, she was actually pretty good at the game. I don't know why I was surprised; Mario Kart's been a series for a long time, older than both of us combined.

"Ooohh, this takes me back." she whispered under her breath after we finished a race. "Thanks for letting me blow off some steam with you."

"No problem." I said.

"You're too young to think about this, but if and when you ever get a girlfriend in the future, treat her right."

"What do you mean?" I ask, sitting up to stretch my limbs.

"Us girls, well... we like attention. We like getting treated like princesses and getting hugs and kisses and... other stuff."

"What kind of other stuff?"

"Grown up stuff." Guh, the grown up wall. Every time anyone wants to hide something, they just say it's a grown up thing.

"Come on, just tell me." I demanded. I wasn't going to argue I was grown up enough; no way was I going to get away with that.

"If you MUST know, my boyfriend, or soon to be ex-boyfriend, insists that we wait before we have s..." her voice drifted off, like she was struggling to continue. "Sex."

"Sex? What's that?"

"It's something grown ups do to show how much they love each other. It's like kissing, but a lot more... intimate. And fun."

"How is it fun?"

"It just is, now please drop it. It's bad enough that I mentioned it to you, and please don't tell anyone else that we talked about it." Jenny picked up her controller again Now are we gonna do another race or not?"

"Okay." I picked up my controller and started cycling through the maps. As I selected one map, I couldn't help myself; I was just too curious about this sex. "So why does he not want to have sex with you if it's so fun? Does he not love you?"

"It's some stupid pact he made at his college. He'll prove his faith to God and remain celibate until he gets married and until then, we're not going to have sex or kiss or hug; hell, we can't even hold hands, according to his stupid pact!"

"Oh, that sucks." I said with sincerity. "I'd have sex with you."

"W-WHAT!?" she exclaimed in a high pitched voice. "You don't say that to just anyone!"

"Why not? I kinda like you."

"You don't even know what sex is!"

"Yeah, but I'd still do it. I kinda like you, Jenny."

Jenny let out an exasperated giggle and buried her face in her hands.

"What's wrong?" I asked.

"Nothing, I'm just... taking stock of my lot in life." she sighed through her fits of giggles. "My boyfriend becomes a monk and a little boy all but declares his love for me."

"Is that a bad thing?"

"Oh, you have no idea!" she laughed. "I'm almost inclined to take you up on that offer, just to stick it to my soon-to-be ex!"

I continued to stare at her with curiosity. I still didn't know what sex was, or why she was upset because her boyfriend wouldn't have sex with her and why he wasn't in the first place.

"Alright, here's my deal." Jenny said, sitting upright and grabbing her controller. "If you can win the next race, I'll have sex with you and show you what my ex has been missing!"

"Okay!" With an objective to shoot for, I was fired up. I selected the next map, specifically one that I was a real pro at. I didn't tell her that; I wanted to win. What I didn't know was this was apparently her best course, too.

"Hah! I'm not gonna lose to you on THIS course!" she said as she left me in her dust in the first two laps. Right as we began the final lap, I lucked out and got a pile of bananas and threw them down on the curve just before the finish line. My trap worked, and though she had a good lead ahead of me, she lost all of it as she tried to make the turn, slid into one of them and fell right off the course.

"Oh no!" she exclaimed as Lakitu placed her back on the course, but it was too late. I was able to dash right past her with a shield of green shells to stop me from getting wiped out by my own trap, and I stole the race right out from under her.

"Oh, you sneaky boy." she chuckled. "Alright, I didn't actually expect you to win, but a deal's a deal, I guess."

Jenny sat up to face me. She gave me a very serious dead-eyed stare.

"Now... before we do this, are you absolutely sure you want to do this?" she asked. I nodded my head. "Okay, then... turn off the console. You won't be interested in it once we begin."

After I put away the Wii U, I rejoined Jenny on the bed. She pulled me into her lap, and I felt a strong sense of elation. Maybe I was getting restless thinking about what sex was and eager to begin, but there was something more to it.

"You're only eight, so I guess you've never had your first kiss before?" she asked.

"Mom kisses me goodnight and goodbye all the time." I said. Jenny smiled and shook her head.

"No no, it's a different kind of kiss. A unique kind of kiss." she explained. She moved me back and placed me down so my head rested on my pillow. Jenny then leaned in, and our lips pressed together. My eyes widened. I recognized this kind of kiss. This was the kind of kiss mom and dad did. This was a special kind of kiss, I could tell. My hand gripped Jenny's shirt, and her hand coiled around behind my head and held me in place. My face grew hot, almost like I was running a fever, and my heart was racing. Once Jenny pulled away after I don't know how long, I was breathing heavily like I had just run a mile.

"I guess I'm your first kiss as well today." she said. Her tone was different now. It was much softer, and again I sensed the same kind of... aura, I guess you could call it, that I felt in my mom. As I lay there trying to catch my breath, Jenny pulled off her shirt and, with a quick twist of her fingers to unclasp the bra from the front, revealed to me her breasts. They were odd-looking, large lumps of flesh with a pink bump on each of them. I knew all women had them, growing them for some reason at some point in their lives, but seeing them up close like this, uncovered by her shirt and bra gave me a sense of longing. My mom had them as well, and though it was difficult to think of now, I had very distant memories of seeing them, of being extremely close to them.

"I'm told that every boy thinks about these all the time." Jenny said as she reached down to pull my shirt up over my head. She tossed the clothes onto the floor and shifted down so she rested right up against me. Her breasts were inches away from my face. "They're still growing, but what do you think?"

"They look... nice." I said. "Strange, but nice."

"Give it a few years. You'll find them absolutely irresistible."

Jenny pulled me closer until my face was pressed up against her breasts. They were unbelievably soft against my face, and warm. I couldn't resist rubbing my cheeks against them.

"Hee hee, I can see you're enjoying them already," she said. "But try doing this." Jenny turned my head and repositioned herself so one of the pink bumps pressed against my lips. I suddenly had this weird moment of deja vu, like I have been in this position before. Then, extremely vague and distant memories came flooding to the surface. I suddenly remembered that I had done this with my mom a long time ago. My lips closed around the pink nub and I began to suck on it. I could feel Jenny tense up briefly, and then her hands wrapped around my body and held me closely.

"Mmnn... I never imagined I'd be doing this, nursing a young boy." she mused to herself. "That's a good boy. Keep sucking at my tits."

As I nursed off of her, Jenny's hands groped at my pants. She unbuttoned my fly and pulled down my pants and underwear. I nearly jumped a foot as I felt her hands grab and fondle my peen, but I continued to suckle at her breasts.

"Huu, you're already hard." she cooed as she held it with a firm grip and moved her hand up and down its length. "Does it normally get that way for you?"

"Yeah. Why is that?" I asked, pulling away from her breast to take a breath.

"That's what your body does when it's eager for sex."

"It sometimes gets hard and stands up randomly."

"Well, you're also a growing boy. Your body is prone to do all kinds of weird things you don't understand yet."

Jenny pulled away from me, and I wiped the drool off my lips with the back of my hand. She lifted up my legs and pulled my pants completely off, leaving me completely naked before her. I instinctively covered my privates, but then I remembered that she was playing with it for several minutes now, and I lay my hands off on other side of my body. I could feel my face flushing red.

Jenny removed her pants to reveal she was wearing an extremely thin and small pair of underwear. It barely covered her up; I never saw girl's underwear before, but they looked worlds different than boy's underwear, and I wondered if they were all like that. She pulled them down as well, and for the first time in my life I got to see what a girl's vagina looked like. Like everything else related to what she hid behind her clothes, I found it very strange-looking. The only naked body I was used to was my own, and I never gave thought to what girls had down there. The only way I could describe it was they had nothing at all. She climbed back onto the bed and laid down with her legs spread apart so I could get a better view.

"Feel free to check me out, if you want." Jenny said, seeing the curiosity in my eyes. "Just be gentle with it. You wouldn't want me to be too forceful with your peen, would you?"

I nod absentmindedly, focused more on the detail of her mound. It wasn't blank, but rather a fold that looked more like a cut between her legs, but it was more elaborate than a simple gash. The top of the hole, as I spread it apart, had a bump and a fold of skin that protruded. The lips were puffy and the hole itself was very hot on my hands. It was extremely weird to look at, but to call it ugly didn't seem right to me.

"Why is it like this? What does it do?" I asked. I drew my hands away and I noticed a thin film of moisture had accumulated on my fingers. I wiped it off on my bedsheets.

"You put your peen in it!" she said. "This part will be a little difficult, since you're not used to how it feels. If it gets to be too much, just tell me and let me take over, or stop altogether."

"Okay." I sat up and moved forward so our pelvises pressed together. When I felt my peen bathe in the heat from her hole, it suddenly sat straight up, harder and more stiff than it ever has been. It was so stiff it was starting to hurt. Following her instructions, I pushed forward, allowing my peen to slip in between her hot moist folds and into her body.

"Haaah!" I gasped as I felt an intense feeling shoot from my peen and up my spine. I doubled over her, my face pressing into her breasts. It was the most powerful and wonderful thing I ever experienced. Driven by instinct, I pushed myself as deep into her as I possibly could, until our hips pressed tightly together.

"Nnnhh! That's good! Push all the way into me!" Jenny gasped. I pushed even more of my weight into her as I felt her hands clamp down on my butt cheeks. Her fingers dug in, which felt amazingly ticklish and I tried to pull away, but the only way to go was forward.

"It feels so strange!" I gasped. "But so good!"

"Go on and thrust into me. Move your hips back and forth to push your peen in and out of my hole, but try not to pull all the way out." she instructed. With some difficulty because of all the weird feelings throughout my body, I moved my hips back and forth. I could feel my peen sliding around inside her. Her insides pulled tight around me, flaring up that incredible feeling. It was getting more difficult to continue as that feeling continued to grow stronger.

Everything happening at the moment was a truly memorable experience. The warmth of Jenny's body, the softness, the loving hug; it was better than all of the hugs mom ever gave me combined.

"Muuhh... Miss Jenny! I don't think I can go on much longer!" I said through heavy gasps. The strange feeling was so intense now, I was paralyzed from it. I could barely move my hips in any meaningful way, but I wanted to continue for as long as possible.

"Okay okay, dear. Let me take over." Jenny said, wrapping an arm around me. She rolled us around so I was laying on the bed and she was on top of me. She broke our hug to sit up on my lap. I was still inside her the whole time; she seemed to take care in moving us so I wouldn't slip out of her by accident.

Jenny rolled her hips back and forth on top of me, continuing our sex. I rested my hands on her thighs and thrust up into her with what little energy I had left. My head felt like it was in a fog. I couldn't think of anything but the ball of sheer delight building up in the area just underneath my stomach. Suddenly, Jenny arched her body backwards and let out a loud moan. Her insides clamped down around me, but she continued to roll her hips back and forth.

The ball of pleasure that built up in the pit of my stomach was beginning to unravel, spreading throughout my body. Then I felt a new feeling, one not unlike what I felt when I had to pee, but this felt thousands of times better. I instinctively tried to hold it back in that way I always do when I'm trying to hold it in, but it broke free of my control. What I experienced next was something truly amazing. At the same time, I couldn't describe what exactly it was that I felt. That ball of pleasure that was building in the pit of my stomach exploded, spreading out to my entire body. It made my mind numb and my body very sensitive to everything. I don't know how long I simply lay there, but I was frozen like I was in shock, unable and unwilling to move. Before I knew it, the feeling had passed, and Jenny had climbed off and laid down next to me. She wrapped her arms around me and smothered me with kisses. I found that I rather enjoyed the affection and attention she gave me, especially after the sex we just did together.

"Did you enjoy that?" she asked between kisses.

"What... what happened at the end?" I asked, trying to catch my breath.

"That's called an orgasm. It's why people have sex. Didn't it feel amazing?"

"Yeah, it did! I wanna go again!" I said.

"Already? You should rest up a bit. Sex takes a lot out of you."

She was right. After I came down from that bliss, I felt exhausted like it was much later in the day. Even the days I had PE at school I didn't feel as tired as I did now.

"Alright..." I said as I yawned. Jenny rolled me over again so I laid on top of her, my head resting on her breasts. I laid my arms out at her side so I was in a completely relaxed state. Even if it wasn't sex, I still felt really good just laying here with Jenny, hugging her and feeling her warm soft skin against mine. I slept like a baby through the afternoon.

Later on Jenny told me what sex was all about, and that I was no longer a virgin. I'm still new to all this, but I don't feel any different from before. If being a virgin means I can't have sex, then I'd rather not be one. Every day afterwards when she babysat me, we'd have sex. It was one of the best years of my life, and I'd never forget our first time together.