With my boyfriend out of town on business, I agree to babysit a teenager while his parents attend a class reunion. On the first night, I learn that he has an impressive cock, and knows how to use it. We end up fucking all weekend, including while I'm on the phone with my boyfriend.
I wasn’t really looking forward to my long weekend off from my job at the local pharmacy, since my boyfriend had been out of town on a business trip for the past two weeks, and I didn’t have anything planned for the upcoming three days. So when Mrs. Palmer called and asked if I would mind staying at her house and babysitting her son over the weekend, I grudgingly agreed. I smiled to myself a little, because the “child” needing “babysitting” was actually her 16 year old son, and I was sure she just wanted me to stay at the house so he wouldn’t end up throwing a party and trashing the place. I had babysat Kurt all throughout his childhood, so this was nothing new. But now that I was in my twenties, I felt a little disappointed that I was about to give up my free weekend to keep an eye on a teenager.
“Sure, Mrs. P, when do you need me to come over?” I asked with a sigh.
“Oh, thank you so much, Molly….any time on Friday before 4 pm would be fine. Frank and I are flying to Wisconsin for his 25th high school reunion. We should be home by late Sunday evening. We’ll feel better knowing that you’re here with Kurt while we’re away.”
“No problem, Mrs. P. I’ll see you then.”
I arrived on Friday afternoon, and waved to the Palmers as they headed for the airport. Kurt and I were familiar with each other, so after we chatted briefly, cooked and ate a frozen pizza for dinner, and changed into our comfy lounge clothes for the night, we perched on opposite ends of the sofa and settled in to watch a movie together.
Kurt’s comfy evening clothes were basically a pair of baggy athletic shorts and a white t-shirt. My comfy TV-watching clothes were a pair of thin, loose-fitting, short shorts, along with a thin cotton tank top…no bra. This was definitely comfortable for lounging, but since I had large, 34E boobs, my shirt did nothing to mask the naked tits beneath it. If you looked closely you could see my areolas through the thin material, and the bumps from my nipples were obvious…..and Kurt definitely noticed. I smiled to myself knowing that I was catching the eye of this teenager, and likely teasing him with my thin top, wobbling boobs, nipple bumps, and baggy short shorts.
After a while of watching TV, I was sitting cross-legged on the sofa, with the TV remote sitting on my leg, as I occasionally texted with a friend. Kurt didn’t really like the movie we were watching and was getting restless, so he leaned over and reached for the remote on my leg. I snatched it away and said, “What are you doing? I’m watching this.”
He said, “No, you’re not….you’re texting.” And he continued to grapple for the remote.
I held the remote away from him in my right hand, and said, “It doesn’t matter, I don’t want to change the channel.”
He laughed, and started wrestling me for the remote, climbing on top of me and grabbing at it, as I turned and twisted and maneuvered so that he couldn’t get it. We were both laughing at his futility….but then I realized, he wasn’t really working very hard to get the remote. Instead, he was grabbing and squeezing my tits and nipples, and even sticking his hands between my legs, as he pretended to be wrestling me for control of the remote. Once I realized this, I glanced at his crotch and immediately noticed the outline of his cock running down one leg of his shorts. It was clearly getting hard, and was pressing against the loose fabric of his shorts. The more we wrestled, the more his shorts rode up on his thighs, and I found that I could see the head of his dick, and about 2 inches of his shaft, hanging below the hem of his shorts. I was kind of impressed. For a kid in high school, he had a pretty impressive prick. It wasn’t fully erect yet, but I could see it hanging down one leg of his shorts, and it appeared to be around 8 inches long, and fairly thick.
Since my boyfriend was away on business, it had been a while since I’d enjoyed a good fuck, and I found that I was enjoying the back and forth with Kurt as we wrestled around on the sofa, with him now openly massaging my tits and pinching my nipples.
“What are you doing?” I shrieked, laughing as we rolled around on the couch.
“What does it feel like I’m doing?” he said.
“It feels like you’re grabbing my boobs and trying to finger my pussy,” I said, as I playfully pretended to push his hands away.
“Well, then, I’m doing something right,” he laughed.
I was enjoying Kurt’s attention to my tits more than I expected to, and I slowed down my “resistance” to let him get better handfuls of breasts, and even to allow him to push my panties to the side so that he was rubbing his fingers along my pussy lips, eventually pushing two fingers inside me.
“Kurt….we probably shouldn’t be doing this,” I suggested, with a wry smile. But even as I said this, I put the remote on the sofa table, and reached out with my left hand to grab his growing cock, gently running my hand along its length and up over the head.
“I think we’re already doing it,” Kurt said, as he pulled my tank top up over my swaying breasts, and began sucking and nibbling on my stiffening nipples. At the same time, he began using his two fingers that were inside my pussy to gently rub my clitoris in a rhythmic cadence that was sending little shockwaves through my body.
I closed my eyes, laid my head against the back of the couch, and began stroking his shaft a little faster. “Holy shit, Kurt, where did you learn how to do that?”
He laughed and said, “I’ve had a few dates since the last time you babysat me.”
As he said this, I felt an amazing, warm orgasm wash over me like a tidal wave, and I leaned my head back and moaned as it overwhelmed my senses, causing my nipples and clit to stiffen and tingle. I pumped his dick even harder and almost immediately I heard him grunt, then felt a blast of hot cum splatter across my jiggling tits. I looked down at his rigid shaft in my hand and watched it continue to spew its milky white jizzm all over me until I had pulled out the last few drops from his nut sack. I slowed down my strokes as he finished cumming, then continued gently sliding my hand up and down his prick while he enjoyed his orgasm. I noticed with a grin that, in keeping with most teenagers, Kurt’s cock remained fully erect, even after he finished cumming. I was still leaning up against my side of the sofa, and Kurt was kind of all up on top of me, as I kept gently pumping his rod, while marveling at its size and the fact that it wasn’t getting any softer.
Just then my cell phone buzzed, and I reached for it with my free hand. It was my boyfriend, Larry, calling from Boston to say goodnight.
“Hey, Molly. How’s it going?” he said.
“Okay…how’s it going in Boston?” I said, still stroking Kurt’s rigid pole.
“Not bad. Sorry this is taking so long. I think it’ll finally be done by the end of next week.”
“No problem,” I said. “I’m stuck babysitting this weekend, anyway, so no big deal.”
As I said this, Kurt sucked one of my nipples into his mouth and started fingering my pussy again, which was absolutely dripping. I covered the phone with one hand and whispered, “Kurt…what the fuck!?” In response, Kurt pulled one of my legs up and draped it over his shoulder, which completely exposed my drenched pussy to his still rock-hard prick. He leaned into me, slowly shoving his cock into my vagina until the entire shaft was deep inside me and his balls were banging against my asshole.
I stifled a moan, then tried to continue talking with Larry, as Kurt slowly pumped his dick into and out of my aching cunt. I was doing OK until Kurt increased the pace and began slamming his dick into me harder and faster, while he massaged and slapped my tits as they bounced around and banged into each other from each thrust. With Kurt’s prick sliding in and out of my pussy, his hands squeezing my boobs, and his nut sack slapping my ass with each stroke, I could feel another orgasm approaching. I had just enough time to put my cell on mute as I let out a low moan when another intense, electrifying climax washed over me. I reveled in the warm sensation of my orgasm for only a second or two before unmuting my phone to continue my conversation with Larry.
Meanwhile, Kurt kept pounding my pussy with his engorged prick until he finally erupted, blasting streams of cum deep inside my cunt. Fortunately, I had just enough time to mute the phone again before Kurt let out a loud grunt when he exploded inside me. As Kurt slowed the pace of his strokes, I unmuted the phone again to continue chatting with Larry, as Kurt gradually finished emptying his load in my pussy.
Larry and I finally finished our call, and Kurt and I just lay on the couch, tangled and on top of each other, with Kurt’s cock still fully erect and stuck deep inside my cunt. “Holy shit….he’s STILL hard,” I thought to myself, with a smile.
After we caught our breath, we both stripped and cleaned up, then flopped back onto the sofa – naked – with Kurt laying behind me – fondling my tits and with his semi-hard dick pressed against my ass – while we found a different movie to watch together. When it was over, we just slept like that on the couch until morning.
The following morning I woke up first, and I could feel Kurt’s morning wood pushing against my lower back, so I reached behind me and gently stroked it with my hand until he woke up. By then my vagina was wet and eager, so I slipped the head of his prick past my pussy lips from behind, then pushed my ass back against him as he shoved his hips forward, impaling me on his engorged cock. He didn’t need any encouragement, he immediately began rocking his hips back and forth, slamming his stiff rod into and out of my pussy, while reaching around to fondle my boobs. I reached between my legs and began rubbing my clit, which – along with Kurt’s pounding cock and tit massage – got me off almost immediately. Kurt’s climax followed quickly after that, blasting a load of hot cum deep inside my cunt.
After catching our breath, we went upstairs and showered together, during which Kurt fucked me from behind again while my boobs bounced against the shower stall until we both erupted with our second orgasms of the day.
We ended up spending Saturday mostly naked – sucking and fucking throughout the day – then sleeping on the couch again, just like Friday night, with Kurt’s hand on my tits and his semi-hard cock pressed up against my ass.
On Sunday morning I gave Kurt a blowjob in the shower, then was able to enjoy another fuck on the sofa after lunch – with me riding his cock cowgirl style that time while he played with my tits and pinched my nipples – before his parents arrived home around dinner time. They paid me my ‘babysitter’ fee and thanked me for looking after things while they were away. I told them I didn’t mind at all, and that Kurt and I had a very nice weekend together.
Larry was still on his business trip the following week, so Kurt and I managed to get together at my place a few times to screw around some more until Larry returned just before the next weekend.
Larry and I got married a year later, and a year after that Kurt went off to college. But ever since that babysitting weekend – all the way until Kurt left to go to college – we’d always managed to find a way to get Kurt’s dick into my pussy whenever Larry was out of town on one of his business trips.