It was just another overnight babysitting gig. Who knew I was going to have babysitter sex? I was nearing the end of high school, and studying hard for the end of year exams. I had turned 18 about a month earlier and was bored with still being a high school girl. I was ready to get out on my own and into a dorm at school. In addition to extra studies, I was also working my butt off, trying to raise extra money so I didn’t have to work during the school year.
So when a friend called and asked me to take her babysitting job at the last minute, I reluctantly said yes. I was supposed to go on a date that night, but I really wanted the money. I called up my boyfriend and told him. He was disappointed, but he understood.
I got there and it was the usual set up. Two kids, make them dinner, get them to bed. Parents wouldn’t be home till late at night, so I had the guest bedroom for myself. The one weird twist was the kids’ grandfather. He lived with the family but didn’t have it in him to care for the kids overnight. He didn’t need my attention and they said he would keep to himself, so I figured fuck it.
It was pretty average. Through the night as I kept the kids busy I got a few texts from Brandon. He was bored and horny. He hadn’t made plans since he thought we would be going out. I felt bad. I finally texted him and broke the big babysitter no-no rule. No boys in the house. I told him to come over and text when he arrived.
He was there in no time. The kids had been in bed over an hour and I hadn’t seen grandpa hardly at all. I shushed Brandon and showed him the way to the guest bedroom.
We wasted very little time. We had been going out a few months and loved making out and fooling around with each other. Recently we had started blowing each other. We wanted to go further but never seemed to get the opportunity.
Our sex drives running overtime, we fooled around whenever we could. It was tough, though, since we barely got alone time or private space. Usually, the back seat of his car had to do.
Tonight we had privacy and even a bed. We were quickly on top of each other, making out and groping. He soon progressed to bringing his hand up under my skirt and was fingering my pussy, first through my panties and then under them. He knew exactly how I liked it and ran his fingers from my wet slit to my clit over and over, lubing it up and then fingering it roughly. I moaned into his mouth as I came, shuddering. He knew my body so well.
I barely had time to recover before he pulled me into a sitting position and stood in front of me. His hard cock was straining against his fly. I eagerly undid his belt and unbuttoned and unzipped his trousers. Pulling the waistband of his briefs down, I exposed his cock and balls. He had a nice big dick and kept his balls shaved. I ran my tongue all over the head of his cock, down the shaft, and lapped at and sucked his balls. I teased the head of his dick, racing my tongue around it slowly, then quickly, then slowly again before I inhaled his entire dick into my mouth. I sucked him enthusiastically until he was shaking. He ran his fingers through my hair and finally grabbed my head and pushed himself deep, the tip right at my throat. He groaned softly as he came, shooting hot cum straight at my throat. I swallowed as he came, not missing a drop.
We collapsed on the bed next to each other, cuddling and talking about how much we wanted to fuck and get it over with. After a while, we put ourselves back together and I walked him out. Out on the back stoop, we.kissed goodnight and got ourselves hot and bothered again. He humped into me, grinding himself on my soaking panties. As I finally pushed him away, the crotch of his pants was wet, and I could see his boner straining against the fabric again. I would have loved to have taken his mouth to my hard clit and swollen lips, but I was too nervous that we had already gone too far in a stranger’s home, with me on the clock.
I sighed and locked up the house. I went to bed, pulling on a nightgown and leaving my soaked panties on the floor by the bed. I fell asleep fingering my hard, wet pussy thinking about Brandon’s cock buried inside.
I woke in the dark, to the feeling of someone’s weight settling on the bed. In my slumber, I thought it was Brandon, settling in next to and slightly on top of me. His lips were on mine, his tongue exploring my mouth. He was eager as always, but a little more forceful and rough. I opened my mouth to greet his tongue.
Then he was groping me again. I spread my legs for him, loving how he explored my pussy. Again though, he was a little rushed, and his touch was rough. Soon he was finger fucking me almost painfully. He shoved two, and then three fingers into me and battered away.
I started to get a little worried. He was going so hard, and something felt wrong. “Bran,” I whispered. “Babe, you’re hurting me…”
He grunted roughly against my cheek and rolled himself more on top of me. As I felt his hard on rub against my thigh, I realized he was naked. I inhaled sharply and tried to move, but he already had too much weight on me.
“Bran, no. Brandon, no, we can’t” I breathed and then froze. He was laughing now, chuckling. It wasn’t Brandon’s laugh. I woke fully and came out of my horny frenzy. I felt his cheek against mine, his stubble rubbing roughly against my skin.
It was the granddad! He was wanting some babysitter sex!
He had me pinned, and his cock was eagerly seeking my pussy. I had my legs spread for him already. I was about to fuck this old man and I didn’t even know his name.
“Wait, please!” I exclaimed. “Grandpa, no! No, I can’t, please stop…”
But he didn’t stop. His weight shifted and his hips dropped fully between my legs. He began probing with the tip of his cock, thrusting upwards toward me. My pussy was swollen, wet, and open for him. There was no barrier and his head found the hole open and waiting for him. He slid in, easily.
I sobbed against him, half in despair and half from the satisfaction of my pussy stretching around him. The head and the first part of his shaft slipped in without resistance and then stopped. I cried out softly and stiffened.
“Please, it hurts. Please stop, please.” He only laughed and grunted and pushed again. Not slowly this time, but with one hard thrust.
He held himself for a moment and my pain eased. He didn’t wait for my sobs to cease but started humping me. It was like when Brandon did it, but now I had the hard cock buried in me instead of rubbing against me. He had filled me, my pussy stretched around him. His balls slapped against the based of my slit and his bony pelvis banged into my swollen clit. All I could do was lay there and take him. His weight was crushing my chest and he was grunting with effort. He started drooling on my face and into my hair as he pumped and ground against me.
His shaft filling me and his bony pelvis grinding my clit was finally too much and my pussy shuddered around him. I felt myself rip even more around his invading cock and wept through my orgasm. Not wanting to touch him, my hands groped and clawed the air. My whole body seemed to cum and when it was over, I collapsed beneath him.
He took that as his cue and his thrusts intensified. I rocked below him as he tripled his pace, finally burying himself as deep as possible and groaning on long, low moan. “Noooooo” I moaned as I felt him cumming deep inside.
And then it was over. He was spent. He collapsed on top of me, keeping me pinned. Slowly, his cock softened and my muscles pushed him out. Still, he lay on me. Slowly I relaxed and dozed off.
I woke the next morning and he was gone. The only remnants of our activity was the ache in my pussy. Embarrassed and ashamed I stripped the sheets from the bed and buried them in the hamper. Sore and shaking I packed my overnight bag and slipped out of the bedroom. He was there in the hallway. I tried to slip by, avoiding his eyes. He stood just in my way, his hand outstretched to stop me.
“If you’re thinking about telling,” he whispered “I’ll just tell them you had your dirty little boyfriend over” then he took my hand and slipped a bill into it. pulling me close to him he whispered: “but if you want some more college money, you know where to find me. I love me some babysitter sex.” This is why I love teen phone sex!
