I have my own babysitter story I'd like to share. This isn't one where the father comes home, sends the wife to bed, then has his way with the poor young girl charged with watching his offspring.
No, this is a story of a young teen, introduced to the joys of sex by a high school aged nymph.
I was 13 at the time and my sister was 8. My parents had planned one of their regular bridge nights at a friend's home and decided they couldn't leave us alone. If it had been me alone, they probably would have. As it was, the sitter was there not so much to keep an eye on us, but to ensure I wouldn't kill my sister while they were gone. The little bitch.
I was none too pleased. Typically, my parents hired an older woman, who was about as much fun as a baseball bat to the head. This night, to my joy, the old bat wasn't available. Instead, when the doorbell rang, I answered to find a young hippy chick standing there.
This was the early 1970s, after all. And, damn, was she cute.
She had long fiery red hair, a grinning, freckled face and stood about a head shorter than me. (I was a big boy, even then. I finally topped out at 6-foot-8 and was edging up on 6-feet by the time I entered my teenage years.) I couldn't tell much else about her body as I invited her in.
She'd obviously seen one too many movies, judging by her look. She was wearing a long peasant skirt, tie-dye shirt, a denim vest and a red bandana on her head. She even had the obligatory “love beads” hanging around her neck.
“Hi,” she said. “I'm Natalie, but you can call me Nate. Mr. --------?”
“Um, no,” I said. “That's my dad. I'm Drew.”
She looked me up and down. She had a curious look on her face, as if she was trying to figure out if she was the butt of some joke.
“You're the kid I'm sitting for?” she asked. “How old are you?”
I grinned and told her I was 13 and she was more there to watch my baby sister and to make sure we didn't kill each other. She grinned and entered just as my parents made it to the front door. After the usual, “Here's where we'll be, emergency numbers, etc.” spiel, my folks headed out the door, leaving Nate and I to get acquainted.
“Um, I've got some homework to do,” I said. “TV and stuff is in the back room. The brat is probably up in her room, sticking pins in voodoo dolls of me, or something.”
“Come on,” she said. “It can't be that bad, can it?”
“You have no idea,” I said.
I headed for the back room to finish up my math, or whatever the hell it was, while Nate headed up the stairs to find my sister. It wasn't long before I could hear the little monster's voice.
I couldn't tell what was being said but, from the volume, I could pretty well guess. I heard a door slam and Nate appeared a few moments later, a look of shock on her face.
“Well,” she said. “That was, um, interesting.”
I just looked at her with an “I-told-you-so” look on my face and went back to my homework. Nate settle down on the sofa, checked the television listings, and clicked on a program.
I was engrossed in dividing fractions, or some such algebra shit, when I heard a moan come from the sofa behind me. It didn't register at first, but then it was repeated, and my curiosity was raised.
“You OK?” I asked, not turning around.
“Ummm, yeah,” Nate said, a somewhat distracted sound to her voice. “I'm great.”
I turned, my eyes growing wide at the sight before me. Nate was stretched out on the sofa, her left arm thrown back over her head. Her long skirt was rucked up well above her knees and, though I couldn't see for sure, it appeared her right hand was underneath on the side away from me. Her eyes were closed, but her mouth was open in what looked like a silent moan. I could see her buried arm moving, slowly, back and forth.
“Hey,” she said. “Come here. You wanna see something cool?”
I put my pencil down and walked over to stand by the sofa. It was clear now that her hand was indeed under her skirt and it was definitely moving.
“Sit down,” she said, that same distracted, almost dream-like quality to her voice. “Down there. By my feet.”
She moved her left leg as I sat, almost hypnotized by what was taking place in front of me. As she did, her skirt shifted, giving me a clear view all the way to her crotch. She wasn't wearing panties and her fingers were busy between the red-furred lips of her pussy, the first one I'd ever seen.
“You like that?” she said.
I could only nod, unable to tear my eyes away from the sight before me. My cock was suddenly very uncomfortable in my jean shorts. Nate brought her left leg up, placed her foot in my crotch, and rubbed the growing bulge she found there.
“Oooh,” she said. “You are a big boy, aren't you?”
She pulled her hand, glistening with her juices, from the juncture of her thighs and sat up in front of me. I noticed for the first time she'd removed her vest and I could clearly see the outline of her tits, with rock-hard nipples, pressed against the dyed fabric.
“Take your shirt off,” she said.
“Um, you first,” I replied.
“Cool,” she said and stripped the garment up and over her head.
Her tits were small. I had no frame of reference, at my age, to estimate their size. Now, with hindsight, I'd guess them to be about a 34B.
They stood proud and firm on her slender torso capped by strawberry pink nipples inside silver-dollar sized areola which puffed out at least half an inch. Her pale skin, which I later learned was nature to redheads, was covered in a light dusting of freckles, a continuation of the design on her face.
Nate reached out and pulled my right hand toward her chest, placing it right over her left tit. She moaned as my hand closed around the fleshy globe, molding itself to her shape. I felt her nipple harden further against my palm.
“Ummm,” she said. “Your hands are warm.”
Nate scooted forward, bringing her legs around my waist, and pulled my free hand to her other tit. Both nipples were now rock hard, diamond points, pressed against my skin. She moaned as I started kneading her flesh then leaned in and locked her lips to mine.
I got the hang of my first real kiss pretty quick. I got distracted again, though, as I felt her fingers fumbling with the snap and zipper on my shorts.
“Let's see what we have here,” she said as she worked the catch and reached inside. I hadn't put any underwear on after my shower earlier and her fingers felt cool as they wrapped themselves around my steaming hot cock.
“Oh, yeah,” she moaned as she pulled my shaft free. “Definitely a big boy.”
I knew, from careful glances around in the gym showers at school, my cock was larger than average. But it still felt good to have an older woman, well girl, telling me I had a big cock.
Things had rapidly gotten out of my control as Nate started stroking me, running her fingers gently up and down the length of my cock, cupping and toying with my balls. I didn't know whether to thrust into her hands or play with her tits or both. As it was, I just sort of sat there, my hands circling her globes as she worked on my cock.
“Get down and sit on the floor,” she said, untangling herself from my legs.
I slid off the sofa and came to rest with my back against it. Nate stood and pushed her skirt down and off. She knelt between my outstretched legs, grabbed the waistband of my shorts and pulled them off to join her skirt on the floor.
“Damn,” she said as she reached out to again grip my shaft. “That's a pretty dick.”
That was the last thing she said for a while as she leaned forward, ran her tongue around the head, then engulfed the shaft of my cock in her hot, wet mouth. My eyes rolled back in my head as I received my first blow job – from the babysitter!
Nate soon had my cock buried down her throat and started bobbing up and down. She moaned as she worked my shaft in and out of her mouth and started massaging my balls in time with her strokes, lubricated by the copious amounts of saliva dripping from her mouth and running down my cock. In no time at all, I groaned as I painted her tonsils with the first blast of my seed, followed immediately by three more.
“Wow,” she said. “That's a lot of cum. Got any more in there?”
I couldn't speak, lost in the afterglow of my first orgasm induced by another person. Nate didn't surrender, though. She kept working my cock between her lips, first draining every last drop of cum from my balls, then working to get me hard again.
It didn't take her too long before she succeeded and I was ready to go again. I'm not absolutely sure my cock really ever got soft. Once it was ready to her satisfaction, Nate slowly climbed up my body until she was straddling my hips. She pulled may face to her chest and fed me her right nipple to suck as she reached down, grabbed my cock, and lined me up with her entrance.
“Just let me do the work, baby,” she said. “Mamma take care of you.”
I have to admit, at the time, that 'mamma' reference freaked me out a little bit. Any nervousness or apprehension I might have had, though, quickly fled as I felt Nate lodge the tip of my shaft in the orifice of her hot, wet cunt.
“Ohhhh, fuck!” we groaned together as she pressed down, taking the head of my cock inside her entrance. “Yeah, baby,” Nate added as she pressed down, slipping her sheath down over my shaft.
“Don't move,” she moaned. “God, that's big. You're stretching me.”
She obviously wasn't a virgin. But, my lord, she was tight. I just sat there, leaning against the sofa, as Nate slowly lifted up then settled back down. A growl escaped her throat as she ground her pubic bone against mine, my cock slipping around in the fleshy glove of her vagina, which felt like it was conforming to the contours.
It didn't take long before Nate was riding me like a bad pony, stretching up until just the head remained inside her, then sitting down to grind her ass into my thighs. Her breathing quickened in time with her thrusts as she pulled me away from her tits and drove her tongue into my mouth.
She was grunting and groaning, her hands resting on my shoulders, as she hunched herself up and down on my cock. Just as I felt the first tinglings of orgasm in my balls, though, Nate pulled herself off me and bent over the sofa.
“Fuck me,” she said as she looked over her shoulder at me and waved her little round ass in my face. “I've been doing all the work long enough. Get your cock back inside me, man.”
I rolled onto my knees and lined up at the entrance between her lightly-furred lips. I rubbed the head of my cock up and down in her furrow, spreading her wetness, teasing what I would later learn was her clit with the tip.
“Mmmm,” she moaned, somewhat impatient. “Stop teasing me and fuck me!”
I lined up the head of my cock where I thought her vaginal opening was. But apparently my aim was slightly off. When I pushed forward, trying to enter her pussy, my cock slipped up and speared the tiny starfish pucker of her ass.
“Oh, Fuck!” she cried as I buried about half my cock in her ass. “God, stop!”
I froze. I guess the only thing that saved her from being complete ripped apart was the copious amounts of her own lubrication coating my cock and her lower body. I started to pull out when she groaned again.
“No, stop,” she said. “Just … don't move for a second. Let me get used to it. You just surprised me, is all.”
“I'm sorry,” I said through clenched teeth. “I slipped.”
“Yeah,” she moaned. “I'd say.”
We must have made quite a sight, the babysitter naked and bent over the couch, one of her charges naked with his man-sized cock buried halfway in her shitter. Once the initial shock wore off, though, I began to realize just how much I liked having my cock in her tight little ass. Her bowels were as hot as her pussy, if not hotter, and silky-smooth, conforming even more to the contours of my shaft.
“Um, spit,” she said.
“Try spitting on your cock,” she said. “Drop a big glob of saliva run down my ass crack and get your cock slippery. Then you can try pushing the rest of it in.”
I definitely liked the sound of that plan. Working up a good mouthful, I let it slowly dribble out. I slipped my cock out, slightly, as the saliva began to run down her split. As it coated my shaft, I pushed back in, very slowly.
“Oh, yeah,” she groaned. “That's better. Damn, that's started to feel really good.”
It took a bit, but I soon had my cock buried balls deep in her ass. She asked me to pause again at full penetration so she could adjust to the girth of my rod. While she rested and relaxed her anal muscles, I ran my hands up her back and around to grip her tits again, pinching and massaging the nipples the way I'd discovered she liked.
“Umm, yes,” she hissed. “Yeah, just like that. Play with my boobs. Pull my nips. Yeah, like that.”
As I got her more worked up, I could feel a slight release of pressure on my cock. Tentatively, I pulled back just an inch, then pushed back in. Instead of a scream of pain, a moan of obvious pleasure escaped Nate's lips.
“Let's try this,” she moaned. “But go slow until I tell you different.”
I started to very slowly fuck Nate's ass. Her breathing was labored, but quickly settled into a more natural rhythm – natural, that is, if she'd just run a 2-mile race. It didn't take too much longer before I felt her pushing back against me and decided it was time to ramp things up.
I reached around and got my fingers on her pussy, finding her clit, as I started to pick up speed. She asked me once to be careful, but kept pushing her hips back against me harder, until we'd built up a pretty good pace.
“Oooooh,” she groaned. “Yeah, fuck my ass. I can't believe you're fucking my ass.”
Nate lifted up slightly, freeing my hand for better access to her tits and pussy. I took advantage and redoubled my efforts to bring her as much pleasure as I was feeling. I'm sure, if I hadn't blown a load down her throat moments before, I'd have already flooded her insides with my cum.
That didn't mean I wasn't getting close. I could definitely feel the early twinges which signaled I was close to cumming, a feeling I was very familiar with from countless masturbation sessions, lying in bed imagining my first fuck.
I have to admit, those early fantasies definitely did not involve ass fucking a hot high school babysitter. Sometimes, reality grabs fantasy by the collar and just beats the living crap out of it.
Nate was moaning constantly now, responding not only to the feel of my cock sawing in and out of her bowels, but the sensations caused by my fingers on her other sensitive zones. She was pushing her hips back, rocking on her knees, driving her ass onto my cock as hard as I was pounding forward. Suddenly, her body clenched, the muscles of her ass rippling around my cock.
“Fuck!” she cried. “Cumming! God, I'm cumming getting fucked in the ass!”
She straightened up, throwing her arms around me and pulled me tightly against her back. Her body quivered as waves or orgasmic pleasure washed through it. If course, being just 13 in the days long before ready access to a variety of internet porn, I had no idea what was going on.
All I knew for sure was: I liked it.
The more familiar sensations in my own body finally peaked as, with a roar, I felt the cum rocketing up the shaft of my cock, firing deep in her bowels. Even though I'd dumped what I thought was the biggest load of my life a few minutes before, it paled in comparison to the volume of cum currently exploding from my cock. It felt like an oil-filled furnace inside her ass as my cock rode through my own juices deep in her guts.
With a couple of more spasms, Nate's orgasm rode its course. She collapsed in my arms, which couldn't hold her, letting her drop face-first into the sofa cushion. My cock slipped from her ass with a loud, wet plop, followed immediately by a massive blob of cum. Nate slowly brought her hands up to cup her abused crotch.
“Oh, my God!” she moaned. “I think you killed me. I think I've died and gone to Heaven. I've never cum that hard in my life!”
“Yeah,” I moaned, completely drained. “That was amazing.”
We slowly recovered, eventually gathering our clothes and redressing, but with much fumbling, touching, tickling and laughter. I went to the kitchen to grab a couple of sodas while Nate went upstairs to check on the brat. She returned moments later to report my 8-year-old sister was oblivious, apparently having slept through the hole thing, despite the noise.
We were sitting on the couch, watching television and laughing, when my parents got home. After Nate was paid and left, I tried to convince my parents she should be our sitter from that day on. They said they'd think about it, but made no promises.
It was the next Monday and I was leaving my junior high school at the end of the day for the long walk home when I heard a horn honk. Looking around, I saw a beat-up Volkswagen Beetle (what else) sitting at the curb. Nate leaned over and shouted through the passenger window.
“Come on,” she yelled. “I'll give you a … ride … home.”
“Who's that?” one of my friends asked, looking at the hot redhead waving me over.
“Her?” I said as I headed for her car. “That's the babysitter.”