Just Another Babysitting Gig

**Author's note:

This story contains reluctance between a younger woman and an older man. The main character is over 18.

I left my last babysitting gig with a $100 tip in addition to my pay. The only thing is, it wasn't just any old tip. It was payment for keeping silent about letting the kid's grandfather take my virgin pussy during the night. He had blackmailed me after fucking me, threatening to tell the couple who's kids I had watched that night that I had had my boyfriend over to mess around in the guest bedroom. The money was shoved into my hand as he told me to come back if I needed any more.

I went home feeling filthy, guilty, and used. I had been taught that sex was only for marriage, and that you should only do it with someone you were deeply committed to. I loved my boyfriend, Brandon, and we were intimate but were trying desperately to wait to have sex. And now here I had gone and let a stranger inside of me. And, on top of that, a perverted old man. A man who was at least three times my age, if not more, and had kids and grandkids himself had not only taken my virginity but had also made me cum on his cock. So far, that had only happened when I touched myself, or when I messed around with Bran. I felt horrible.

A few days of feeling guilty went by. At first, my pussy was sore from the fucking it had taken. I now knew that my hymen was gone, but I also found out that not everyone had one. Sometimes they got ripped from sports, or from getting fingered. I don't know why mine had taken so long to break, as I had let Brandon finger me before, and had even cum around his fingers. Maybe mine had been deeper, I don't know. The pain faded as I went about for the next few days, as did the tenderness on the front of my pelvis where he had ground against me. After a few days, I actually got horny again and masturbated for the first time. I realized that now I wanted something inside of me more then ever and had to get two fingers inside myself just to cum.

At first, out of guilt, I avoided Brandon. At school I had turned away from him when he hugged me, and felt dirty when we kissed goodbye after classes. After that first masturbation session, though, I started to feel less bad. After all, we all had needs, and it's not like I had asked to get fucked that night. Also, I now knew that orgasms weren't always consensual. Mine that night had happened against my will. Towards the end of the week, when Bran hugged me, I returned it fully, even pressing myself against his crotch. His dick stirred against me and I thought about how good it would feel inside of me. So much better than the one that had used me for its own pleasure, thrusting into me for the sole purpose of reaching its own orgasm...

Then I got a call on Saturday from Kate, who's kids I had sat for that night. She asked if I could come over again that night and watch the kids. She said they had enjoyed my company and that her Father had specifically thought I did a great job with them. My first instinct was to say no. I couldn't imagine going back there and seeing him again. Possibly getting forced by him again. But the thought of earning some easy money was too hard to pass up. Especially since most of the hours they needed me were after the kids went to sleep and I would basically get paid to watch movies or sleep.

So I found myself at their doorstep again at 6pm. I figured I would just try harder to avoid letting Granddad into my bedroom again. And I would certainly not have Brandon come over again. That's what had really gotten me in trouble last time. I came in and Kate again showed me around, giving me instructions on what to give the kids for dinner, what they could snack on, etc. I saw Granddad watching us from the sofa and could feel his eyes on me as I got my evening instructions. Kate even stopped to introduce us. "Dad, this is Shay." she said. "And Shay this is my Dad, Joe."

He reached out and looked me in the eyes as he shook my hand. "Hi Shay. I'm Joe but I'm more used to being called 'Dad' or 'Grandpa' these days." He chuckled warmly but held my hand for a few seconds too long. I felt my pussy stir a little in my panties at his touch. Seeing him in the light, I could tell he had once been handsome. He was in good shape for an old man, and aside from his seemingly ever-present stubble, looked like he kept himself clean. He had piercing blue eyes which paired well with his gray hair, which suited him. I finally pulled my hand away and looked at Kate, hoping she had not seen what had passed between us. She hadn't and, after giving some more instructions, she and her husband left for the night.

The evening passed. I made the kids dinner, we played a game, and then I put on a movie and stepped into the kitchen to make their bedtime snack. As I was cutting up some fruit, Joe entered. I froze as he came to stand next to me. Too close to me for comfort. I could feel my hair standing on end and my flesh crawling.

"Hi Shay" he said quietly. "Did you think about my offer?" I simply stood there, staring at the cutting board. I could feel his breath on me as he got a little closer, his chest against my shoulder. He undid his fly and pulled out his cock, already hard, and began stroking it softly. I looked down at it, still too scared to move. It was big, about 7 ½ inches, thicker than Brans, with bulging veins. The biggest difference was his foreskin. Bran didn't have one. I have to admit, I was curious about touching it. But I was too afraid about what he might do to me. Finally, he stopped touching himself and pulled out a wad of money. Peeling one twenty from it, he slid it across the counter toward me. I reached out and took it, pushing it into my pocket. "Good girl", he murmured. And, taking my hand in his, he placed it around his member. He kept his hand on mine and manipulated my hand to begin stroking him. Looking shyly down at my work, I began slowly to take over and his hand dropped away.

I explored his whole length, running my hand from the base all the way to the tip. I stroked him with varying pressure, from barely harder than a tickle, to gripping him tightly. I noticed how his foreskin rolled back as I stroked him and loosely gripped it in my fist, working it up and down over the swollen head of his cock. He was dripping precum as I worked him over and it created a kind of lube for me to work the loose skin up and down, up and down. His breath was quickening and I knew he liked what I was doing and it wouldn't be long till he was finished. He pulled out another twenty and rubbed it up and down his ball sack. Taking the hint, I took the bill and began working his balls with my free hand. They were heavy and full, the skin pulled tight as they pulled up to his body, ready to shoot their thick load. He moaned gently as I found a good rhythm, stroking his shaft and massaging his balls, then going back to using his foreskin to massage his cockhead.

"Don't you dare stop, girl." he whispered. "Oh God, don't stop." His eyes were on my titts now. He watched them jiggle as my hands worked him over. His breath was starting to come in gasps. As I worked, I noticed that my pussy was swollen and my panties were wet. I wanted something inside of me. I tried to focus on making him feel good, though. Finally, he grabbed my hand, gripping it around his shaft tightly as he began to buck his hips. Now he was fucking my hand. I stroked the spot behind his balls that I knew drove Brandon over the edge and sure enough, he grunted as he began to cum. We both watched as the first shot splattered across my belly and I pulled away a little. With his free hand, Grandpa Joe grabbed one of the larger, uncut strawberries from the cutting board. Using the hand wrapped around mine, he aimed his cock at it and spent the rest of his load all over it. Gasping, he released my hand and rested his body against the counter.

He held up the berry. It was dripping with his cum, dripping from the tip down to the leafy base. He showed me another twenty and held the berry up to my lips. "Eat up, girl." It wasn't a request, it was a command. I looked into his eyes as I opened my mouth and licked from the base to the tip and then drew it in for a big, juicy bite. I had had cum in my mouth before and was stunned at how good the taste was when it mingled with the juice from the strawberry. I ate the whole thing right out of his hand as he watched. Taking a deep breath, he stepped back from me. His cock was still softening and he pushed it back into his pants. "Finish your work, girl. And get the kids to bed. I'll see you in a little while". With that, he walked away. I did as he told me, pushing the money he had given me into a pocket in my skirt. I wanted desperately to play with myself, but I knew the kids would start to wonder what was taking so long. I wiped the cum off my belly with a damp rag, hoping they wouldn't notice the wet spot.

I finished the movie with the kids, my pussy aching the whole time. They got themselves ready for bed and I tucked them in. As always, I checked on them after a little while and they were out cold, snuggled in their beds. I hadn't seen anymore of Grandpa and wondered if he was done for the night. He was older, after all. Maybe a good handjob had tired him out. So, after about an hour after the kids were in bed, I decided to get ready for bed myself. I gathered up my things and headed to the bathroom just off the guest bedroom, where I would be staying the night. I showered and brushed my long red hair. I liked my hair. It wasn't bright red, but instead was like a dark bronze color. Furthermore, Brandon loved it, and loved how long I kept it. He loved to run his hands through it as I sucked him off, often gripping it right at the base of my skull when he came. As I thought about him I flushed with embarrassment at how I had gotten turned on jerking off an old man earlier that same night. But the pay was good, and I sort of had fun. I found myself trying to reason that what I had done was ok.

Lost in my thoughts, I started a little as the door opened. Grandpa Joe came in, looking deep into my eyes as he did, and closed and locked the door behind him. He said nothing as he walked up behind me, keeping eye contact with me in the mirror. I kept my gaze on him for a moment, trembling and scared to move. Then I dropped my eyes submissively.

I was wearing my usual nightgown. I was raised in a conservative, religious manner, so it covered my breasts, and went down to mid-thigh. In our house, we also wore a dressing gown over our night clothes. We were not expected to show off our bodies. My parents would be horrified if they found out I had even kissed Brandon, nevertheless sucked his cock to orgasm. And here I was, in my nightie with an old man pressing his hardening cock to my backside.

He was in his boxers and a tank top. I had heard the style referred to as a "wife beater", but I don't know why it was called that. He reached around my body with both hands and put them to my breasts. In one hand he had a bunch of bills folded up. He peeled one twenty dollar bill of the outside and began running it over my breasts. Shyly, I took it from his hand and placed it on the vanity. He smirked and began undoing the buttons on the front of my nightgown. One by one he opened them, until my breasts were fully exposed. Well-proportioned to my body, my breasts weren't large, but they were firm and perky. I had large areola in proportion, and puffy nipples. Grandpa began to fondle them, rolling and pinching them. He slid another bill into my hand and pulled my body back against him, exposing my throat, which he began to kiss and suckle. That was it. My sweet spot. I sighed and melted against him.

He sucked my throat and massaged my breasts and nipples, bringing me to a dizzied state. I closed my eyes and let myself enjoy the pleasure he was bringing me. His hands began to explore my body, running down to my hips and across my belly and I didn't think to resist. I won't lie, it felt good. His hands got closer and closer to my sex, which was hot and wet. I opened my eyes and looked at what he was doing. Suddenly I wasn't sure what to do. I should tell him to stop, but I didn't want to. His fingers ran across my swollen clit through the night gown and I gasped at the pleasure that ran through me. My clit grew when I got turned on, extending out from my body almost an inch. Brandon loved to suck on it and I would cum anytime he did, gushing juices over his mouth. Thinking of Brandon, and realizing what I was doing, I pulled away from his touch and stiffened a bit. He pulled a fifty dollar bill from the bundle. Showed it to me, and began waving it over my crotch. My clit was so hard and I could feel my pussy pulsing with my heartbeat. I took the money from his hand and pulled the skirt of my nighty up, exposing my bare pussy to him.

I kept my pubic hairs trimmed, because Brandon liked it. He trimmed his also and we enjoyed how clean that was when we sucked and licked each other. Tonight was no different, as I had just trimmed the day before. The lack of hair showed how far my clit had pushed away from my body, looking for all the world like a micro-penis. Grandpa Joe stuck his fingers in his mouth, wetting them thouroughly before beginning to stroke my engorged clit. Up and down, round and around he rubbed, all the while suckling my throat and the back of my neck. I moaned softly as he began to finger my wet slit, sliding in just a little, and then using the juices to moisturize my clit.

Reaching down to his boxers, he released his cock from the fly. Keeping me standing upright with my legs spread, he pushed his cock along my slit and past my clit. Looking down, I could see the head poking out through my legs. Pulling back, he repeated the motion, running back and forth through my legs, masturbating me with the head of his dick. He drove me wild like that for a few minutes and I was lost in pleasure and desire.

Finally, he pushed my shoulders forward and my hands came to rest on the counter. My hips and ass were stuck out at a different angle and, when he pushed forward, he began to enter me.

"No", I whispered. "Please don't make me again..."

He pulled another two fifties from the bundle. Folded them, and stuck them in my mouth. As I closed my lips on them in acceptance, he pushed into me. My head rolled as I felt him filling me, spreading me. Slowly, agonizingly slowly, he pushed till his hips rested against mine. Then he held himself there and began grinding himself inside. Side to side he ground, spreading me open inside. I felt pressure building as he did, and wetness seeping out of me. I felt like I was going to tear open and explode from the inside out, waves of pleasure rolling over me. Finally, he reached down to my clit and began massaging and I shuddered and came. Grunting and groaning and bucking my hips against him.

I came and came for what seemed like forever. A different kind of orgasm as my clit and pussy both pulsed with pleasure. As sometimes happened with Brandon, cum squirted out of my pussy as I came, soaking my thighs, and Grandpa's cock. As I came down from the orgasm, my legs got weak and my knees buckled. Grandad used his hips to push mine against the vanity, and my body fell forward onto the counter. He grabbed my hips and began slamming himself into me. Grunting and beginning to sweat, he squeezed my ass, my thighs, my hips, sometimes slapping my ass, sometimes squeezing so hard it hurt. Slap, slap, slap, I heard his body slamming into me. I felt my pussy opening up for him as he roughly pounded into me, loosing himself in a fury of rutting.

Having pleasured me, all his thoughts were now on himself. He fucked into me, banging my hips into the edge of the counter. In the morning, I would awake to bruises there, and on my hips and ass. I was coming down from my orgasm and was suddenly aware again of how wrong the situation was. Overpowered and weak, though, I could only lay there and take it. A slight sickness rose up inside of me as I realized he was getting closer and closer to cumming inside of me again.

"Grandpa, please. Please don't cum inside me." I whispered. He laughed, and grunted. And then he pushed himself in and held. He groaned and I knew he was cumming. I felt his wetness mix with mine. Felt the warmth of his seed inside of me. I cried softly onto the counter top, the money still in my mouth. I was no longer a virgin, but now I was a whore. I was used and soiled from the inside. He collapsed on top of me again and I laid there, feeling his cock soften and slip out of me. As it did, I felt our combined juices run down my thighs.

He pulled away and stood over the toilet and relieved himself. I simply laid there, feeling cum run down my legs. He came back to me and stroked my hair, now damp with sweat. He stood me up and straightened my night gown, and buttoned the chest back up. Kissing me once on the lips, he muttered "Good girl." And left the bathroom. I had liked it. I had loved it. But did I want it? I wasn't sure. I got myself cleaned up, and went to bed. Feeling my battered body and my exhausted pussy starting to get sore, I drifted off to sleep, wondering who I was now. A rape victim? A whore? His mistress? I wasn't sure. And I wondered what I would do the next time I got a babysitting call...