Just Another Babysitting Gig

*Author's note: It's been a while! I've wanted to continue this story for some time, I'm sorry for the delay. This story is one of non-consensual sex between a younger girl and an older man. (Or two). If that's not your thing, move on to the next story. If it is, great. This chapter explores adding another person who will push boundaries. Let me know what you think, and if you want more.*

I left my last babysitting gig with even more money than the first time. A tip for services rendered and a bribe to keep quiet about them. My "services" had gone far beyond taking care of the kids, though. I had taken bill after bill as I gave the kid's grandpa a hand job in the kitchen, and then even more as I let him fuck me in the guest bathroom later that night. I had fallen asleep wondering if I was a whore now, taking money in exchange for sex....

When I woke the next day I gathered my things and got ready to leave and again, Grandpa J stopped me in the hallway. "I know you liked it" he whispered, his face close to mine. "It's okay to like it, you're a good girl. I'll see you again soon." Then he blew lightly on my ear and kissed it before walking away. I shuddered, feeling my nipples harden and my pussy pulse. I was sore down there and had bruises from where my hips had slammed into the bathroom counter last night. But I wasn't as hurt as the first time and my feelings of guilt and remorse faded a little faster. At school over the next few days, I was distracted by how my body felt and I would shift in my seat just to feel my shorts press against my swollen clit. Regular make out sessions with Bran almost always lead to us fondling each other after that. A few times I tried to pull him on top of me but he would hump himself against me, refusing to push inside. He would finish on my stomach or in my mouth and I would go home and play with myself, unsatisfied. I thought more and more about taking his virginity.

So when the next call came for me to come and babysit at Kate's, I was conflicted and excited. I arrived on time and listed to instructions on dinner and bedtimes. As usual, the kid's grandfather would be home, but this week Kate's older brother was also in town. He was home on leave from the Marines, but I probably wouldn't even see him since he had a date that evening....

After dinner the kids got themselves ready for bed. It really was an easy job. They were accustomed to their parent's going out and staying out late. As I stood at the sink doing the washing up, Grandpa Joe came in and stood behind me. He pushed himself up against my back and brought his hands around to my breasts, letting them wander and feel me. I stood still as a statues, letting him touch me. My clit immediately hardened and pushed against my panties. He brushed his hand against the front of my skirt, just barely making contact with my swollen clit. "I love how big and hard she gets." He murmured in my ear "Get those kids to bed and come out by the pool, I'm gonna suck that big clitty till you cum all over yourself tonight." With that he pulled away, leaving me horny and dizzy.

I did as I was told, waiting to go outside until I was sure the kids were asleep. When I went out, Grandpa J was stretched out on one of the lounge chairs. It was just the beginning of summer, and the evening was just warm enough for swim wear, but the old man was stretched out on a lounge chair with only a towel draped over his crotch. He clearly had an erection and was lazily stroking at it. He gestured for me to come to him and I obeyed, wondering what was in store for me this time. He usually caused both pleasure and pain and I found that frightening but also a little thrilling. Every step I took towards him, I was tempted to bolt away. I figured he would take what he wanted eventually though and found myself standing next to the lounge chair, waiting for his next command.

He reached up and pulled my swimsuit bottoms off. I stepped out of them as he sat up and brought his face to my crotch. My clit was standing at attention, practically reaching out to him and begging for his mouth. Grandpa Joe didn't disappoint. He ran his tongue from the base of my shaft to the little head before sucking the whole thing into his mouth. He sucked hard and then released, filling the swollen member with even more blood and somehow getting it harder than before. He repeated that several times and each time the pain of the suction was replaced by a wave of pleasure when he released it. My head swam and I was lost to the sensation and found myself running my hands over his face and head and moaning gently. My pussy was aching and drenched and all I wanted was for him to fill me up again.

He worked my clit with his mouth and tongue, occasionally lapping at my dripping slit until I was bucking my hips and felt the shiver of an orgasm building inside of me. Every time I got close, he would back off and focus his attentions to another area or would simply stop and stroke his hard cock. Eventually he reached up and guided me into his lap, facing away from him. His shaft stuck up between my legs and for a moment, it looked like it was part of my body. I glided my slit over it a few times, watching in wonder as my slick juices stuck to him before he lifted me, angling my body so that I was open for him. He lowered me onto him in one motion and I sank down, taking his whole cock inside of me. I moaned in pleasure as he filled me. My skin suddenly felt like it was on fire, wanting to be touched everywhere. My reservations about letting this old man have his way were forgotten, again.

Grandpa Joe didn't let me down. He guided my hips into motion over his lap before reaching around me, playing with my breasts and squeezing my nipples. Every once in a while he would pinch one of them harder. And harder. And harder. He would bring me just to the edge of squealing in pain before releasing me. When he would let go a flush of heat would pour over me. I was lost in sensation.

We were both snapped out of our pleasure at the sound of a car door slamming out in the driveway. Loud, angry words could be heard and it sounded like a couple arguing. We froze, listening. It sounded like the car sped off and the back gate opened. A man I hadn't seen before stepped into the yard and stopped, looking at the two of us. He was the perfect picture of a man. Tall and muscular. His hair was cut in a military style high fade and I could only guess that this was the brother Kate had told me was in town. Apparently his date had ended badly. He grinned as he took in the picture of his father with his dick buried in the babysitter and beneath me, Grandpa J recommenced grinding his hips.

"Hey Tom." He said. "Why don't you come join us?"

Tom didn't need to be told twice. As he walked towards us, I could see the massive bulge in his trousers. I wondered if it was similar to Grandpa's, or if he was also uncircumcised. He didn't make me wait long to find out as he stepped over the end of the lounge chair, unbuttoning and unzipping his pants. Behind me, Grandpa Joe pushed my shoulders forward so that I was now bent at the waist, my hands resting on the chair. Tom pulled his cock out and it was already half hard. Uncut like his father, he was just as long and looked thicker. I leaned forward, taking him in my mouth and starting to suck him to full hardness. I worked him over with tricks I knew Bran loved, going between teasing the head and nibbling the shaft, to sucking as much of his length into my mouth as possible. Behind me, Grandpa had stood up and I was taking hard cock in both ends, bent over at the waist with my hands gripping the lounge chair trying to hold myself steady.

They worked me for a little while that way before Grandpa pulled out of me from behind. His son Tom was holding my hair like a ponytail, attempting to get more of his length into my mouth and throat. Abruptly he pulled my head away and turned me around, pushing me into a position where I re-mounted Grandpa Joe, facing him this time. My pussy opened and sucked him inside as I settled on top of him again. Tom rested himself behind me, straddling the lounge chair and using his hips to guide mine, effectively riding the two of us. Grandpa sucked and bit my breasts, leaving dark red marks all around my nipples.

Then from behind me, Tom changed his angle. He pushed my shoulders down, planting me firmly against his father. He shifted himself and brought his huge hard dick up to my butt hole. He spit in his hand and rubbed it on himself before he started to try and push in. Realizing I was about to lose my anal virginity, I started to struggle but the two of them had me pinned between them. Trying to push up with my legs only lifted my hips up and gave Tom's searching cock a better angle. He grabbed my hips to hold me still and Grandpa held my chest and shoulders down against him. I felt the tip of the invading dick pushing against my outer ring. Steadily pushing. He was dripping precum, leaking into me as he probed and wetting my resisting sphincter. Push, push, push and then POP. He broke through my outer barrier. Heat scorched through my anus and my whole body seized. It occurred to me that I should be screaming but I was frozen, my eyes wide and staring at Grandpa Joe as he held me.

We were all still for a moment and then Grandpa started moving underneath me. He pumped up into my pussy a few times. Hard and rough, trying to bring my awareness back to that area. The pain in my rear hole began to fade and I relaxed ever so slightly to discover that caused the pain to fade. I started to breathe again, trying to relax. As one cock pounded my pussy, the other began to gently ease forward inside of my ass again. His thickness pushed slowly but relentlessly inward, filling my guts and stretching my hole. Somehow, the tension spread to my front hole, making it impossibly tight. The border between pain and pleasure blurred and all my blood seemed to be pushing into my swollen pussy and clit, which was now getting ground into Grandpa's pubic bone as he pushed himself into me over and over. Tom finally came to rest with his balls on my ass, fully implanted inside of me and the feeling of being filled and pounded, entirely used by two men washed over me. The heat from my full sex and asshole spread up my back and over my head and as I locked my mouth to Grandpa Joe's and our tongues met, my pussy began to ripple with the strongest orgasm I'd ever experienced. Both men were riding me as I writhed in ecstasy, grunting in pleasure as my body milked them. They found their rhythm and Tom met his father's thrusts inside of me, pounding into my ass with the same intensity Grandpa J was giving me from below. I could feel them grinding inside of me, meeting each other's cocks through a thin barrier between my two passages. My orgasm peaked and I released, squirting fluid from my pussy. The heat and moistness pouring all over his cock sent Grandpa Joe over the edge and he grunted loudly into my mouth as he came inside of me. Tom held out, pounding my ass and grinding himself down into the two of us as we came and came and came. It seemed like this was going to be my existence now, cumming on these men as they filled my holes....

Finally, the pleasure subsided and my body went slack, muscles exhausted from the full body orgasm. I laid there with my head on the older man's chest as his son pulled his fat dick out of my asshole. I murmured submissively as the younger man picked me up and flipped me over, laying me on the ground in front of the pool on my back. He lifted my legs, bending me in half and climbed on top of me, thrusting is hard fat erection inside of my sloppy wet pussy. My ankles were up on his shoulders and my pussy was angled up, giving him full access and he took advantage of it, pushing himself all the way in. He was a huge guy and he had me wrapped in his arms, his body in full control of mine. I lay on my back helplessly as he filled me and held me steady and began to pound me mercilessly.

Tom's cock was long and thick. My pussy was soaked in a combination of my own fluids and Grandpa Joe's cum. As Tom thrusted in and out of me, there was a sick sloppy wet sound. I looked down and watched his monster cock slamming into me, my huge clit pulsing and aching, standing up to meet his body each time it met my pelvis. I saw my pussy gushing into his pubic hair with each thrust. He noticed me looking down and grabbed my face, forcing me to look at him. He squeezed my jaw and my mouth obediently opened as I looked into his eyes. Never breaking eye contact, he released a line of spit from his mouth, directly into mine. I accepted it as I accepted his body inside of mine.

I was his plaything, meant only to be used for his pleasure. I stuck my tongue out, asking for more and he gladly obliged before thrusting his tongue into my mouth. He explored my mouth while he ravaged me, his hands roaming down from my face to grope my breasts and pinch my nipples. As his body encompassed mine, my pussy once again clamped down around his member in orgasm. This one wasn't strong enough to make me squirt again, but I clenched around him and drove him over the edge. He grunted and drove himself deep into me as he came, rocking his cock instead of pulling it back.

He stayed inside of me instead of pulling away but didn't relax completely. We looked up as his father approached and dropped down to his knees over my face. Again I obediently opened my mouth to his semi-hard member and began cleaning and sucking it. He hardened again and sighed as he dribbled a small amount of cum into my mouth. The two men pulled out of me simultaneously, leaving me dripping in sweat and cum next to the pool.

"I'm spent for tonight, son" announced Grandpa Joe. "You take her in and clean her up. Have all the fun you want but make sure she's good to go home in the morning. Her parent's still think she's a virgin."

He left us there, Tom standing over me, his half-erect member dripping and hanging heavy between his legs. I wondered how much more he could possibly have left in him as he easily scooped me off the deck and carried me inside...