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When I was a teenager, my parents divorced and my father married his much younger secretary, who had a young son of her own.

Even after their wedding, my father continued to employ my new stepmother, so they hired a full-time babysitter for my stepbrother, which was great because I didn’t have to deal with him.

The babysitter was a student at the local junior college, and she was hot as shit. Vanessa was half-Mexican with these gold, snake-like eyes. She was little, 5'1" at the most, and she’d clip-clop around our house in her wooden clogs and short denim skirts. Sitting at the kitchen table pretending to do my homework, I would stare at her perfect heart-shaped ass as she prepared snacks at the counter. Her tits were like two big, velvety scoops of ice cream. I was totally in love.

After that school year, Vanessa transferred to a college in another part of the state. The only thing remaining of her was a photo with my stepbrother that my stepmom stuck on the refrigerator. I tore off the half with my stepbrother and kept Vanessa’s half under my mattress, jerking off to her caramel cleavage every day.

Even though I always dreamed of blowing my first load in Vanessa, I eventually lost my virginity to someone else. I went to college and finally grew out of my awkward teenage body and adolescent fantasies. I kind of forgot about Vanessa.

After my sophomore year I went home for summer break to stay with my family. My stepbrother was still young enough to require supervision, so in the beginning I was stuck watching him. This was reason to get a job. Fast.

Then one morning when I came down for breakfast, my stepmother announced I was officially off the hook for babysitting. Vanessa was home for the summer, too, and was on her way over to babysit my stepbrother.

As soon as I heard her name, a shiver ran down my spine and my dick stiffened. Should I stay home or make myself scarce? I put off job hunting for the day. I was way too curious to see how she looked, and whether she was as hot as I remembered.

Turns out, she was even hotter.

“Rob!” Vanessa squealed when she walked into our kitchen, pulling me in for a hug. “You look so great.”

“Thanks,” I replied, trying to keep my cool.

Her ass was still that same upside-down heart wrapped up like a gift in her skin-tight jeans. She was braless underneath her skimpy tank top.

“You look amazing, too,” I said.

“Yeah?” She blushed. “You’re so big now!”

My stepbrother and his friend were in the basement glued to the PlayStation, so it was just Vanessa and me. After a few minutes of catching up, I told her about a band I’d started at school and asked if she wanted to hear a song we’d recorded.

Next thing I know, Vanessa’s in my room and sitting on my bed, those same wooden clogs dangling over the edge. She smelled like she’d been dipped in coconut suntan lotion. Images of her naked, lubed body ran through my head.

“I like that guitar part,” she said. “Is that you?”

I lied and said it was, even though I played bass.

We were silent for a minute. I wasn’t sure if she was waiting for me to put an end to the conversation or to make a move. But when she rubbed my shoulder and said, “You really are so big now,” I decided to go for it.

Right away, it was on. We sucked face for a minute or two sitting up, and then she snaked herself under me and pulled me on top of her. I took off her tank top and there were those titties, the ones I had jerked off to for years, except these were even better. In my fantasies, her nipples had been flatter, but the real ones poked out like gumdrops. With every lick of my tongue and nibble of my teeth, she moaned and writhed.

Vanessa’s tummy was flat and warm as I licked my way down it. Her pussy, I swear to God, was like no pussy I had ever tasted. How do I explain it? It was almost…sweet. She was entirely shaved, and I devoured her smooth skin like an animal. Something came over me. I was outside of myself as I toyed with her clit, and licked every inch of her.

Vanessa moaned and demanded I stick my finger inside her. I slipped a digit in and kept my tongue working. She pushed her pussy hard into my face, lifting her torso. Moving my hands underneath her backside, I took the opportunity to flip her over. I wanted that ass.

I had Vanessa on her hands and knees with my face between her luscious cheeks, my finger in her pussy, and she came like that. She could have farted in my face and I wouldn’t have cared. She was just that hot.

After she came, Vanessa pushed me onto my back and moved her lithe little body down my front. She removed my cock from my jeans and took the entire thing into her mouth, watching me like a cat with those golden eyes. She bobbed her head like a buoy bouncing in the water while tickling her nails all over my thighs.

I did not want to come before I fucked her, so finally, I made her stop. I wrestled my remaining clothes off and reached for the condom in my wallet. Thank God it was there, or else I’d have exploded after one thrust inside her.

That little pussy felt as good as it tasted. Vanessa was tight and wet, and she kept telling me how good my dick felt inside her, how big it was, as I fucked her with the crazed adrenaline of an MMA fighter.

I fucked her missionary with her legs up around my shoulders. I fucked her doggie-style and made her come again on my dick. I sat on the edge of my bed and she sat on top of me, riding me like a perverted cowgirl. I fucked her on my old desk next to my Cubs pennants. Bam. Bam. Bam. Right hook, left hook, upper cut. I was knocking us both out.

When I knew I was about to come, I ripped off the condom and she jerked my wet load onto her perfect tits.

“Mmmm,” she said, licking me off her fingers.

When we were done, we got dressed quickly, just in case my little brother came upstairs. But we lounged around on my bed for a while.

“I always had a crush on you,” I said.

“Really?” she asked, laughing.

“Yeah,” I said. “Wait.”

And with that, I reached under the bed. The picture of her was still there. I took it out and gave it a kiss, and hoped she didn’t think I was creepy. Apparently she didn’t, because she fucked me again and again, all summer long.

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Babysitter Redux

  • 2

Trama

When I was a teenager, my parents divorced and my father married his much younger secretary, who had a young son of her own.

Even after their wedding, my father continued to employ my new stepmother, so they hired a full-time babysitter for my stepbrother, which was great because I didn’t have to deal with him.

The babysitter was a student at the local junior college, and she was hot as shit. Vanessa was half-Mexican with these gold, snake-like eyes. She was little, 5'1" at the most, and she’d clip-clop around our house in her wooden clogs and short denim skirts. Sitting at the kitchen table pretending to do my homework, I would stare at her perfect heart-shaped ass as she prepared snacks at the counter. Her tits were like two big, velvety scoops of ice cream. I was totally in love.

After that school year, Vanessa transferred to a college in another part of the state. The only thing remaining of her was a photo with my stepbrother that my stepmom stuck on the refrigerator. I tore off the half with my stepbrother and kept Vanessa’s half under my mattress, jerking off to her caramel cleavage every day.

Even though I always dreamed of blowing my first load in Vanessa, I eventually lost my virginity to someone else. I went to college and finally grew out of my awkward teenage body and adolescent fantasies. I kind of forgot about Vanessa.

After my sophomore year I went home for summer break to stay with my family. My stepbrother was still young enough to require supervision, so in the beginning I was stuck watching him. This was reason to get a job. Fast.

Then one morning when I came down for breakfast, my stepmother announced I was officially off the hook for babysitting. Vanessa was home for the summer, too, and was on her way over to babysit my stepbrother.

As soon as I heard her name, a shiver ran down my spine and my dick stiffened. Should I stay home or make myself scarce? I put off job hunting for the day. I was way too curious to see how she looked, and whether she was as hot as I remembered.

Turns out, she was even hotter.

“Rob!” Vanessa squealed when she walked into our kitchen, pulling me in for a hug. “You look so great.”

“Thanks,” I replied, trying to keep my cool.

Her ass was still that same upside-down heart wrapped up like a gift in her skin-tight jeans. She was braless underneath her skimpy tank top.

“You look amazing, too,” I said.

“Yeah?” She blushed. “You’re so big now!”

My stepbrother and his friend were in the basement glued to the PlayStation, so it was just Vanessa and me. After a few minutes of catching up, I told her about a band I’d started at school and asked if she wanted to hear a song we’d recorded.

Next thing I know, Vanessa’s in my room and sitting on my bed, those same wooden clogs dangling over the edge. She smelled like she’d been dipped in coconut suntan lotion. Images of her naked, lubed body ran through my head.

“I like that guitar part,” she said. “Is that you?”

I lied and said it was, even though I played bass.

We were silent for a minute. I wasn’t sure if she was waiting for me to put an end to the conversation or to make a move. But when she rubbed my shoulder and said, “You really are so big now,” I decided to go for it.

Right away, it was on. We sucked face for a minute or two sitting up, and then she snaked herself under me and pulled me on top of her. I took off her tank top and there were those titties, the ones I had jerked off to for years, except these were even better. In my fantasies, her nipples had been flatter, but the real ones poked out like gumdrops. With every lick of my tongue and nibble of my teeth, she moaned and writhed.

Vanessa’s tummy was flat and warm as I licked my way down it. Her pussy, I swear to God, was like no pussy I had ever tasted. How do I explain it? It was almost…sweet. She was entirely shaved, and I devoured her smooth skin like an animal. Something came over me. I was outside of myself as I toyed with her clit, and licked every inch of her.

Vanessa moaned and demanded I stick my finger inside her. I slipped a digit in and kept my tongue working. She pushed her pussy hard into my face, lifting her torso. Moving my hands underneath her backside, I took the opportunity to flip her over. I wanted that ass.

I had Vanessa on her hands and knees with my face between her luscious cheeks, my finger in her pussy, and she came like that. She could have farted in my face and I wouldn’t have cared. She was just that hot.

After she came, Vanessa pushed me onto my back and moved her lithe little body down my front. She removed my cock from my jeans and took the entire thing into her mouth, watching me like a cat with those golden eyes. She bobbed her head like a buoy bouncing in the water while tickling her nails all over my thighs.

I did not want to come before I fucked her, so finally, I made her stop. I wrestled my remaining clothes off and reached for the condom in my wallet. Thank God it was there, or else I’d have exploded after one thrust inside her.

That little pussy felt as good as it tasted. Vanessa was tight and wet, and she kept telling me how good my dick felt inside her, how big it was, as I fucked her with the crazed adrenaline of an MMA fighter.

I fucked her missionary with her legs up around my shoulders. I fucked her doggie-style and made her come again on my dick. I sat on the edge of my bed and she sat on top of me, riding me like a perverted cowgirl. I fucked her on my old desk next to my Cubs pennants. Bam. Bam. Bam. Right hook, left hook, upper cut. I was knocking us both out.

When I knew I was about to come, I ripped off the condom and she jerked my wet load onto her perfect tits.

“Mmmm,” she said, licking me off her fingers.

When we were done, we got dressed quickly, just in case my little brother came upstairs. But we lounged around on my bed for a while.

“I always had a crush on you,” I said.

“Really?” she asked, laughing.

“Yeah,” I said. “Wait.”

And with that, I reached under the bed. The picture of her was still there. I took it out and gave it a kiss, and hoped she didn’t think I was creepy. Apparently she didn’t, because she fucked me again and again, all summer long.

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