Banging His Former Babysitter

It was fifteen years ago. Anything could have happened in between. Marriage. Babies. Gray hairs. But when I moved back to my hometown for the summer and Scottie asked me out in line at the mini mart, of course I said yes. One look at his sea green eyes framed by long dark lashes, and the head of dark curls that brushed against his shoulders, and I almost forgot that I used to babysit him. Almost.

He was twenty-three. Me, thirty-two. He was the one who had recognized me, shockingly, while trying to buy a six-pack and some ultra lights.

“Em? Em Washburn?”

“Uhm, excuse me?”

I was hung-over, the product of a long night of catching up with hometown friends. Nobody knew how to drink me under a table like they did. I was wearing sunglasses, which had slid down my nose, and I peered at him over the tortoiseshell frames. I clutched the beer close. Hair of the dog.

“I’m sure I know you but you’ve gotta give me a little clue, sorry.”

He laughed, curls bouncing. “It’s okay. I wouldn’t expect you to recognize me. Not now at least. Scottie. Scottie Lancaster? You, uh. You used to babysit me.”

Oh shit. It all came crashing down. The long summers spent eating popsicles together and hanging out at the neighborhood pool. Me inviting my friends over and taking naughty swigs out of his parents’ liquor cabinet. His mom’s friendship with my own mother, the two of them drinking margaritas on the porch while I watched Scottie inside. Scottie’s piles of summer reading we’d read aloud together. Me leaving for college, forgetting about that long ago summer gig. He was always a good kid. Well behaved. Not fussy. Easy enough to keep track of. But damn, this was not a kid standing in front of me. This was a full-grown man with little tufts of chest hair creeping out of his button down. Speaking of creeping, was I a creep for feeling a nudge of attraction towards him? It was Scottie! Little Scottie who used to run around with popsicle juice smeared all over his face. No way was I letting myself go there. This was a cute little run-in, a flashback down memory lane. I’d been his babysitter, emphasis on baby. Nope, step away.

“Scottie! Oh my god, wow, hi. Sorry I didn’t recognize you. Yeah, you uh, you do look different.”

“Thankfully. Would be such a bummer to still be rocking eight year old looks.”

I laughed. So did he. God he was cute. That jawline, where did that come from? I shook my head. Snap out of it. “I’m surprised you recognized me. I definitely have a few more wrinkles than when I was seventeen.”

“No way. What are you? Thirty? That’s not wrinkle territory.”

“Oh, you just wait. You have no idea what fun is on the horizon, my dude. And I’m thirty-two.”

“Spring chicken.”


“You wanna grab a drink sometime?”


“Do you want to grab a drink?”

“Um, sure. Yeah, sure. When?”

“How about tonight?”

And so that was it. Of course I told myself it was absolutely not a date – nothing of the sort. Just two old friends catching up. But one Tequila Sunrise in, and that face? God it just kept getting more suave. Can you tell at eight that someone is going to grow up to look like a model? To be honest, I could hardly see any traces of the child he was in the looks he had now. There was something mesmerizing about him, and I couldn’t help it. He was grown and he was beautiful. His leg bumped against mine under the table, and he let it stay there, his thigh touching mine. That move. Okay, so he was interested, too. Fuck.

We went back to his place for a nightcap. His idea. I was still telling myself it was just a regular hangout. I had plenty of friends I did this with. Nothing sexual about it. But sitting cross-legged on his plush rug I let him continue to brush up against me under the coffee table. And then he did it. He kissed me. His lips parted against mine and I felt myself brushing my tongue over his teeth, tasting the mezcal we’d been drinking on his mouth. Smoky sweet, daring me. I pulled back. We looked at each other. And then we tumbled onto the rug, a tangle of limbs.

“Please tell me you never fantasized about this,” I mumbled into his hair.

His hands were following my spine, gliding down to my lower back. “Of course I did. Later though. Teenage years.” He was kissing my neck, my chest. “You’re so hot, Em, fuck. Do you even realize how sexy you are? This part of you.” He kissed the swell of my cleavage. “Here.” My collarbone. “You’re unreal.”

I rolled on top of him, bumping my head on the coffee table along the way. “Ouch.” I rubbed my skull. Scottie sat up and buried his hands in my hair, pulled me in towards him. He kissed my head, rubbing the place I’d hit it with his thumb.

He grinned. “Now who’s taking care of who?”

I wrestled him to the floor, pinning him with my thighs and letting my hips grind into his as I straddled his pelvis. I felt him harden beneath me, his jeans suddenly taut against his bulge. I worked my hips over his, feeling him against my clit. The seam of his jeans rubbed against my slit, and I could tell I was getting wet.

He reached around and worked my shirt up over my head. I’d worn a slinky lace bra, and my breasts filled it like two little peaches. Scottie pinched my nipples through the fabric.

“Your tits are amazing.”

“I know.” I leaned down and kissed him, open-mouthed as his hands cupped my chest. I ran my hands over his arms, down his stomach. I found his belt buckle and undid it slowly, still working my lips against his. He squirmed beneath me, obviously beside himself with desire. I took my time, slowly unwinding the leather strap from around his waist. When it was off I slapped him with it lightly, teasingly, across his stomach, and then threw it to the side.

“Do you remember when you used to put me in timeout? When I’d done something really
bad. So bad. Like playing with the ash in the fireplace. Or hiding my broccoli from dinner in your shoes.”

“Oh my god, I do remember that. Funny, before you said that I remembered you as so well behaved. There’s a lot you’re proving me wrong about tonight.”

“Not such a good boy, am I?”

“No, no you’re not.” I rubbed deeper against him, thrusting my hips down against his so hard I saw him wince slightly with pain. “You need to be reminded of what it means to behave, don’t you?”

He nodded vigorously. “Yes, yes I do.”

“Yes, please. Mind your manners.” I reached for the belt, slapped him across the stomach again. Less gently this time. He writhed beneath me and cooed with pleasure. “You like that?”

“So much.”

I did it again, even harder this time. His skin flushed, and for a second I felt bad. But when he stretched his neck skyward and arched his back, I felt him get even harder and I realized this was his shit. I decided to pinch his nipples, and his hips rose up into mine, mouth opening into a quivering O. Maybe this was my shit too.

I inched my way downward, lingering over his belly button to bite the skin there. Not hard at first. Then, admittedly, pretty damn hard. The bite marks made me wet. When I got to the edge of his pants I licked the skin there and tasted salt. One button. Two. The zipper. And then he was in my hands, his hardness full and the tip of his cock slick with a slight glaze of precum. I licked it off. This was always my favorite, the little appetizer. I smacked my lips and went in for more. I took him fully in my mouth. He was uncut, and I worked his foreskin up and down with my lips wrapped tight around his shaft. He was whimpering, his fingers tangled in my hair and hips shaking slightly. I smiled around his cock. Anyone who felt that giving head was disempowering was doing it wrong. No faster way to turn a guy to putty.

I slipped my mouth down his dick, further, further, until it was flush with his base and his tip was jutting against the back of my throat. My eyes began to water, and I let up, raising my head with long threads of saliva dangling from my mouth. I made direct eye contact with Scottie as I wiped my lips with the back of my hand.

“Fuck that’s hot. Sit on my face.”

I obliged, scooting quickly out of my skirt and throwing my underwear back over my shoulders. I lowered myself onto him and he latched around my pussy. He began sucking, running his tongue along my slit as he did so. I let all of my weight rest on top of him, and he inhaled deeply through his nose. His tongue was inside of me, and he reached up with one finger to work my clit. I lifted up slightly to give him some air, and he attacked my clitoris with his tongue. Whirling in circles, gently biting, sucking. For being twenty-three I had to hand it to him. This kid could give some head. His hands clenched my ass cheeks, and I could feel his nails digging into my skin. He rocked my hips harder against his face, and he disappeared between my lips. Finally, when I was actually growing concerned that he might be suffocating, he lifted me off and gasped for air. My cunt was vibrating.

“Shit, Scottie. Good work.” He pulled himself up, wiping his mouth as he did so. His entire face was glistening. I was so turned on I couldn’t wait for him to reposition and fuck me, and I began massaging my clit with my fingers as he readjusted. He lay me down and moved inside of me as I kept pleasuring myself. His chest rose over me, and I lifted my head up to give one of his nipples a little nip. He laughed.

“You’re insatiable with that, aren’t you?”

“I didn’t know until tonight! It’s really doing something for me though. I bent forward and bit his stomach, digging my nails into his back. My pussy hummed.

“Yeah, well, good. Me too.” I spanked him. “Ahh, that’s the shit.”

I took hold of his ass and pumped him in and out of me. When I looked down I could see his shaft slick with my wet, his dick rosy and flushed. He was sweating, and I rolled on top of him to do some of the work, to take control of the situation. I began bouncing up and down on his cock. Pilates had really been working wonders for my dick riding muscles, and I worked my pelvis in small figure eights, in circles, up and down. I thought Scottie was going to blow his load any minute, but he held tight. I could see the muscles in his forehead straining to keep it together. His concentration was palpable. I loved this, seeing the effect my little tricks had on him. It was so easy. But I wanted to get off too.

I guided his hand to my clit and with my hand over his we massaged it together. I slipped one finger inside of me, and felt him, rigid and wet, gliding against it. I was leaning over him, my tits dangling in his face. He kept lifting his face up, straining to lick them as they bounced, his tongue flicking out of his mouth. I kept them out of his reach. I liked watching him like this, wanting.

Finally, we were both close. I held the back of his neck and closed my eyes, concentrating on riding the wave of pleasure that was building in my pussy muscles. It began deep inside of me, and traveled out in rings of vibrating sensation, my clitoris the core where it settled. I came in a burst of small orgasms, each building into the other until I was shuddering and flattened on top of Scottie. My thighs were sticky with cum, and I realized we had finished at the same time.

“Thanks for going out with me.” Scottie mumbled into my hair.

“Yeah…let’s not tell our moms about this okay?”

“God no.”

“Absolutely not.”

“No, no.”

“So… uh, wanna maybe do this again?” I was feeling bold. That sex had fucked me up and I wanted more.

“Definitely. You have to sit on my face more though.”

“That’s not a babysitter joke is it?”

“No way. I’m incredibly serious about that.”


This was going to be a fun summer.