Babysitting Blues - Cover

Babysitting Blues

by Demonhead

Copyright© 2021 by Demonhead

Fiction Sex Story: Young girl gets dominated by ex-boyfriend

Caution: This Fiction Sex Story contains strong sexual content, including Mult   Teenagers   Blackmail   NonConsensual   Rape   Fiction   Humiliation   Gang Bang   First   Babysitter   .

I sent the last email on my list and leaned back in my wonderful soft chair. I felt an itch and scratched my right leg. My fingers ran over the tops of my stockings. I looked down at my leg and ran my hand over my soft but firm thigh. I was in good shape even though I would be turning the ripe old age of 22 in a week. I liked the way stockings felt and that my thighs were bare.

The fact that my gym was in the same building that I lived and worked was a plus. The incentive program my boss set up didn’t hurt either. The gym was state of the art and he could see my workout history any time he wanted to, and he actually paid me for it. He insisted I stay in shape “for the business” he would say. I was perfectly ok with that as long as it resulted in money in my pocket and a tight body.

The money was special. I didn’t tell anyone but the fact that a secretary, excuse me, an administrative assistant could make six figures at the age of 21 sort of blew my mind. Who was I to question, my boss was doing fine in that arena and if he wanted to pay me like that so be it.

I looked at the clock and then realized I had been daydreaming again. I was out of stuff to do and that was usually a bad thing as my mind would start to wander. I always seemed to eventually wind up in the same memory though. I seemed to get there even quicker around my birthday. It was understandable as the event in question happened seven years ago, the weekend after my 15th and it set the stage for the rest of my life as it turned out. I was babysitting for the Johnsons again and their sweet twin girls.

I had just put the girls down for the night, they were finally sleeping. I was coming down the stairs and the doorbell rang. It startled me a little, the Johnsons were not coming home until the next morning. They were afraid the reunion was going to be a little wild and they had gotten a hotel room to be safe. I felt ok with it, I was a big girl, mom and dad were close and the Johnsons were only about an hour away if anything horrible happened. I had no plans for tomorrow anyway.

The Johnsons were a wonderful couple, young, excited about their new twin girls and a lot of fun to be around. It also didn’t help that they were drop dead gorgeous, especially Mr. Johnson. He was tall with dark hair and piercing brown eyes. I had to stop myself from staring quite often. She was adorable with short blonde hair and a cute face. I called them by their last name, and it drove them crazy. They said it made them feel old. They were not old, in fact only about nine years older than I was but I needed to keep the formality. It helped to remind me that he was married, and I was a high school sophomore.

My bare feet hit the hardwood at the bottom of the stairs, and I peeked out of the window to see who was at the door. It was 9:00 at night. Who could be here now? I pulled the curtain slightly and saw Billy Oliver standing on the porch. Dammit! I did not want to see him. The doorbell rang again. Crap! He was going to wake the kids, I slid over to the door and opened it slightly.

“What do you want?” I hissed at him.

“Hey, baby girl. I just wanted to talk a little. Please let me in, it’s cold out here.” He said with his blue eyes shining and his perfect face smiling at me. Damn him.

I opened the door and he walked in. His hair was messed up by the wind and just made him even cuter than normal. He looked at me and I felt a flutter in my chest. No, I would not allow this.

“You can stay for thirty minutes.” I said coldly and closed the door.

He didn’t say anything, just hung his coat over the banister and smiled at me. I rolled my eyes and walked into the kitchen. Billy Oliver was the school hunk and a heartbreaker. He was the quarterback and easily the cutest guy in school. We had dated for nine months. We were the “it” couple until we broke up a few days ago and it wasn’t pretty. I said some nasty things to him, and he wasn’t very nice to me. I was really surprised he was even here and even more surprised that I wasn’t throwing things at him. Why was I such a lightweight?

“Baby girl, thirty minutes with you is like an eternity.” He said in his smooth, soft voice.

“Billy, cut it out! Why are you here? I really don’t want to fight with you again and nothing is going to change.” I said in a spiteful voice.

I saw his mouth wrinkle in a frown and his blue eyes lock on mine.

“That’s too bad. I was hoping you had reconsidered.” He said, a little less smooth.

Billy had played me like a fine instrument while we were dating. He had kissed me on the second date on my doorstep. He was a great kisser. On the third date his hand was under my shirt while he was kissing me goodnight, again on my doorstep. I was so into the moment I didn’t realize what was going on until he was pinching my nipple. The fourth date we made out for pretty much the entire movie. I could kiss him forever. Towards the end of the show, I felt my bra pop and his hand was immediately over my bare breast. I never figured out how had he gotten my shirt open without me feeling it. The boy was a master.

I didn’t realize how truly masterful he was until our next date. We were in his backseat, in a secluded neighborhood under construction. The windows were fogged up completely. I was kissing him so hard my lips were starting to hurt. I pulled back and realized my shirt was entirely unbuttoned, my bra hanging loose from my arms and he was now licking on my sensitive nipples. I watched his head as he worked his magic on my little body. I was still a virgin and I felt like I was in total control of the situation even though I was barely 15. I had no intention of giving up my virginity until my wedding night.

I knew that was old-fashioned, but I didn’t care. It was important to me. I didn’t feel like a tease, I let him do whatever he wanted above my waist but below was out of bounds. He hadn’t pushed it until now; he knew very well how I felt. I thought he understood but then I felt his hand slowly crawling up my leg. I didn’t react as it slipped under my skirt and touched my thigh. It felt wonderful and a little sound came out of my mouth. I suppose he took this as a sign of approval and his hand touched the front of my panties. That was what caused me to panic, I knew I had to stop him now or I wouldn’t be able to later. I pushed him away immediately and caught my breath. He was looking down at me with that sad puppy dog face.

“Baby girl, what’s wrong.” He asked, running his warm fingers over my tight stomach.

“Billy, you know we can’t go any farther.” I said, my voice trembling as he ran his fingertips under my breasts.

“Sweetie, you just need to relax and let it happen.” He whispered and squeezed my right nipple softly.

I felt my breath escape in a gasp as my entire body shuddered. I remember the tinge of doubt entering my mind and whirling around. He was good and he did know how to make me melt in his arms. Maybe it would be ok, I thought for a second.

He leaned forward and kissed me lightly on the lips. I moved slightly up to meet him. He slipped his arm under my back and pulled me close. I felt my bare breasts crush against his hard chest. His tongue was running though my mouth and wrestling with mine. I wanted to eat him right there. He pulled away and kissed me on the nose, then the forehead and then down my neck. I could feel the heat building again. He kissed down my chest, gently kissing my firm nipples and then down my stomach. I held his head in my hands. I felt myself letting go but my mind was cloudy with sexual energy. I felt my skirt being slowly pushed up; I felt his lips touch my thigh. I moaned and closed my eyes. I felt his breath between my legs. I knew I had to stop him; my mind was screaming but my body refused to listen. His tongue flicked along the side of my panties and then slipped under them.

I sat up quickly and immediately pushed my body away from him. He looked up, holding my legs. I was hooking my bra and trying to gather my shirt. I could see in his eyes the anger building but I didn’t care. I needed this to stop now, or I would regret this moment for a long time. I sat up. He got angry then and started screaming, I remember hearing the words “prick tease” and “leading him on”. That discussion was not pretty and ended with him physically tossing me out of the car. I sat on the ground in disbelief as his tires screamed and dirt shot up in the air. The air was quiet and then I felt a chill. I looked down and my shirt was still completely unbuttoned, and my bra was not hooked. I looked around and was thankful the nearest house was a couple hundred yards away. I hooked my bra and buttoned my shirt. I didn’t bother tucking it in and started to walk. It was only a couple of miles from my house, and I made it home in under an hour. I was so angry the cold had no effect on me.

We did have a couple more conversations in the hall the next week, but they all ended the same. I was not interested in going any farther and he was insistent. He was throwing the “love” word around, but I saw right through him. I was a conquest, a prize, something he couldn’t have, and it was driving him crazy.

“What do you mean by that, hoping I would reconsider? You know how I feel, I am not going to change my mind.” I felt my voice rising but stopped when I remembered the kids were asleep upstairs.

“I don’t know, I just hoped you would, it would be so much easier that way.” He said, smiling.

I felt a tinge of fear hit me.

“What are you talking about?” I stammered.

“Baby girl, you are special. I think you may be the last virgin in our school, maybe even in our town. I was hurt that you valued that label more than our relationship.” He said.

“Billy, it has nothing to do with you. I told you I was waiting for my wedding night and it’s more than just a label.” I said.

“Please, Jenny, are you kidding me? Who does that anymore? It’s a noble goal but a little unrealistic, don’t you think?” He said with a twisted grin.

“You do realize you are talking about my body and what I do with it is my business, not yours. I don’t care what anyone else does, this is what I want.” I said sternly, feeling my strength coming back.

“Too bad.” He said softly and pulled out his cell phone.

“What in the hell do you mean by that?” I said, trying to sound strong but the fear was again hanging in the background.

“You’ll see.” He muttered and I could tell he was texting.

“Billy, you have to leave now. I’m not supposed to have boys over here and you have been here long enough.” I said and stood, taking a few steps toward the door.

“No, Baby Girl, I am not leaving yet but you can go ahead and walk down the hall and get the door if you don’t want the doorbell to wake the kids.” He said.

I froze. I looked back at him. He was smiling calmly. I heard a noise on the porch, and I ran to the door quickly. I looked out the side window and there were four boys standing on the porch. I could see two of them, they were football players and friends of Billy. I couldn’t make out the other two, but I saw Jimmy Thompson reaching for the doorbell. I ripped open the door and he jumped back a little.

“What are you guys doing here?” I screamed at them in a soft voice.

“Billy invited us. He said you were having a party.” Jimmy said and I saw Bobby Jones punch him in the arm and the others laughed.

I closed the door in his face and stormed back into the kitchen.

“Just what do you think is going on? You get out of here now and take your neanderthal friends with you or I’m calling the police.” I said and could feel my frustration and anger with this boy brewing over.

“Relax, baby, no need to get so excited. We can all stay calm. Just let me get this text sent and we will all be on our way. Your daddy’s phone number is this, right?” he said and held up his phone.

I looked at the number and it was my father’s cell phone number. I ripped the phone from his hand and hit the button to display the message. It was a picture of me in my room. It looked like it was taken from the foot of my bed. I was naked and lying on my bed with my legs spread wide, my right hand on my pussy. My left hand was squeezing my left breast, it was obvious to anyone what I was doing. I didn’t remember when it was. I didn’t masturbate that often but often enough not to know this exact time. I felt my heart start to race, and the sweat began to form on my forehead.

He took the phone from my hand and started to press the send button.

“Wait!” I said and I felt the tears start to well up in my eyes.

“Where did you get that?” I asked.

“Oh, you don’t need to worry your pretty little head about that. I have plenty more where that came from and you should see the video.” He smiled and then chuckled.

I was having trouble understanding everything. Questions were flying through my head too fast for me to process anything much less ask out loud. I just stood there with my mouth open, stunned.

“I know, it’s hard to come to terms with that stuck feeling. You see, I always have a backup plan, but I was hoping to avoid using it this time. I do like you, a lot, and I had so hoped it would have worked out between us, but I guess this will work too. Now, you turn your cute little ass around and go let my friends in.” he said in a tone like he was talking to a child.

I stared at him, he smiled and cocked his head. I turned and shuffled to the door. I opened it slowly, moving like a zombie. The boys filed in past me and went towards the kitchen. I recognized the other two when they passed me. They were also football players; one was Tommy Johansen and the other was Kirk Thomas. They were both huge and I looked up at them as they walked by me. I was barely 5 feet tall and only weighed 100 pounds. I had been on the varsity cheerleading team in high school since the 8th grade. I was a flyer and my small size allowed me to reach pretty high in the air. I had no idea how big the boys were, but I didn’t even reach their shoulders and their arms looked like they were the same size as my legs. I dropped my eyes as Kirk passed and noticed he had a case of beer in his hands. I closed the door and followed them into the kitchen.

Billy, Jimmy, and Bobby were already sitting at the table and Jimmy was shuffling cards. Tommy was pulling out a chair and Kirk dropped the case of beer on the island. I stood there, not sure of what to do or say. I was scared and starting to panic.

“Baby girl, can you get us each a beer and put the rest in the fridge, please.” I heard Billy say.

I looked at him angrily and just stood there. I watched him get up and noticed some of the guys made a soft “oooh” noise. He walked slowly to me and lowered his head to my ear.

“Sweetheart, I have enough footage of you naked to create an entire website. I especially like the scenes of you and I on your bed with me sucking on these cute tits. If you want to keep any shred of self-respect in this town you will do exactly as I say. You may have a chance of salvaging a little dignity or I could just send your Daddy and all of your friends the video of his little girl rubbing on her pussy. Your choice.” He whispered and sat back in his chair.

I pictured my Daddy looking at that and felt another surge of tears hit my eyes. I felt them start to run down my cheeks as I pulled beers out of the case. I sat one in front of each guy. I went back to the island and picked up the rest of the case. It was heavy but I was mad, I felt like I could have lifted a car. I carried it over to the fridge and started to make room.

The guys were laughing as I stood up and closed the door. I thought they were laughing at me, but they weren’t, they seemed to be in the middle of a card game now.

“Baby, come over here and sit on my lap, I need a little help.” I heard Billy say.

I willed my feet to move and shuffled over to him. I stood next to him and he pulled back away from the table and patted his lap. I turned and sat down. He pulled my right leg over until I was straddling his lap, facing the table. I was happy I was wearing jeans as my legs spread to surround his. He pushed his chair closer to the table. I saw all the guys staring at me. My hands were on the table and Billy slid his arms under mine and held his cards in the front.

“Please hold my cards for me baby. My hands are tired.” He said.

I took his cards and held them up. He immediately put his hands over my breasts. I pulled my arms in to cover my chest. I felt his breath in my ear.

“Relax, sweetie, it will go much better for you if you just let it happen. It is going to happen, you can’t really do much about it now, you just have to decide if it will be easy or hard.” He whispered.

I pulled my arms away and held his cards out in front of me. His hands moved out from under mine and reached up to touch my brown hair. My hair color was the only thing missing from the whole blonde cheerleader/quarterback stereotype. I felt him touch my ponytail and flip it. I tried to stay calm and work on how I could get out of this. He pulled my hair tie out and my hair fell over my shoulders. I loved my hair, it was brown, thick and long. It reached to just above my breasts. He fluffed it up.

“Isn’t she beautiful guys?” Billy said as he played with my hair.

The guys just shook their heads like bobblehead dolls.

“Ok, back to the game, I bet 10.” Tommy said and I saw him throw a bill on the table.

“What do you think, baby? Tommy is betting 10 bucks; you think I should call?” Billy said.

I did not know what to do. I didn’t know anything about poker, I thought that was what they were playing. Billy had no matching cards and his cards were pretty spread out. I didn’t think it was a good hand.

“I don’t know.” I said, trying not to burst out crying.

“You got to play to win, baby. I think we will call that.” Billy said.

I looked down and realized there was no money in front of Billy. I didn’t understand what was going on and then I felt him grab my shirt. I felt a tug and he yanked the top button off and tossed it into the middle. I dropped his cards and grabbed my shirt. It was one of my favorites, it was blue and buttoned up the front. I always buttoned my shirts pretty high, Billy and I argued about that once too. I looked at my shirt and it was hanging open more than usual with the top button missing but still modest. It was probably where most girls would wear it anyway.

“Billy, please don’t.” I said softly, my tears flowing again.

“Baby girl, you are going to have to relax. We are just getting started.” He said in my ear.

“I don’t understand. Why don’t you have any money?” I asked.

“I don’t need money tonight, sweetie. You see, as thanks for inviting them my friends are allowing me to play with something other than money.” He whispered in my ear.

I was still confused. I looked around the table and the hand was continuing. A couple of guys tossed their cards in and another threw a ten-dollar bill in.

“How many do you want Billy?” Tommy asked.

“What do you think, baby?” Billy asked.

My vision was blurry as my tears were flowing again and I just mumbled. “I don’t’ know.”

“Pick up the cards sweetie.” He said.

I picked up the cards and held them out. He pulled three of them out and tossed them.

“We’ll take three.” He said and Tommy dealt him three cards.

Billy was now playing with my hair again, so I reached down and picked up the three cards. He now had two tens. I thought that was maybe better.

“I will bet another ten.” Tommy said and tossed another bill out.

“Baby?” Billy asked.

“No, please, no.” I said, hoping he would quit.

“Come on sweetie, we need to see what he has.” He said and ripped the next button off my shirt.

I didn’t move as I felt my shirt open up below. I felt a sob hit me as I held onto the cards.

“In fact, boys, I want to raise.” Billy said.

“No, no.” I said and started to move my head back and forth.

“Guys, we need to keep her a little decent for when the Johnsons get back, would you accept a simple unbutton in place of the actual button?” Billy said.

“Sure Billy, no problem.” They said in unison.

“Then I will raise twenty.” Billy said and I felt him start to unbutton the next button.

I tensed up as I felt the button let go and he went to the next one. I looked down and saw my smooth stomach in plain view as the fourth button opened. My lace blue bra was out for anyone to see. My breasts were big for my little body, but they were also very firm. I wore a bra more out of modesty than a need for support. It was pretty but very light and thin. I knew my nipples were probably pressing the light material. I sat up and tried to stay strong. I could get out of this, I needed to stay calm and try to think of something.

The hand went around the table and everyone else tossed their cards in. Tommy did not and looked at Billy.

“I think you are bluffing, my friend.” He said and tossed another bill.

“Lay our cards down, sweetie.” Billy said to me and I did.

“Pair of tens.” Billy said.

Tommy smiled and laid his cards down. I saw he had two kings and two fives. He swept all the money towards him without saying a word. Jimmy grabbed all the cards and started to shuffle.

“Billy, please, what do you want?” I turned my head and whispered.

“Baby, we just want to play some cards, that’s all. I know the Johnsons will not be back until the morning, so we have all night. If you relax you may enjoy yourself.” He whispered in my ear.

“No, Billy, you guys have to leave.” I said as another set of tears ran down my cheeks.

“In time, sweetie, in time. Now let’s see what we have here.” He said.

I looked down to see cards in front of us. I picked them up and looked up. All of the guys were holding their cards and staring at my chest. I pulled my arms in a little to block the view and spread Billy’s cards out. I noticed he had three jacks.

“I will open.” Billy said.

He reached down and pulled on the next button. It was the last one that was outside of my jeans. The others were tucked in.

“We’ll start with ten.” Billy said.

Three of the guys tossed bills in the pot. Tommy tossed his cards in. I saw Jimmy pick up the deck.

“How many baby?” Billy asked.

“Two.” I said in a soft voice.

“That a girl, now you are getting it. Which ones?” He said.

I pulled out the other cards, leaving the three jacks. I tossed them to Jimmy. He dealt two cards and slid them to me. I picked them up. It was a five and a king.

“Nice draw, sweetie, now we kick some ass.” Billy said.

“Big talk, hot shot. Make a bet.” Jimmy said with a chuckle.

“We will bet twenty.” Billy said and pulled my shirt out of my pants.

He undid the last two buttons and now my shirt was wide open. I saw all the guys staring at my chest, I didn’t look down. Kirk laughed and tossed in a twenty-dollar bill.

“I will call that and raise you another twenty.” Kirk said and tossed another bill.

The other three guys groaned and tossed their cards in.

“Well, well, baby, what should we do? It seems Kirk over there thinks he can beat us. Do you think he can beat us, baby girl?” Billy said loudly.

I just sat there and didn’t say anything, I felt myself start to tremble. Billy was silent for a moment.

“Baby, you are going to have to put the cards down for a minute.” He said.

I paused for a second and then realized he was sliding my shirt off my arms. I put the cards down and he pulled my shirt completely off. I shivered as I felt the breeze hit my bare skin. I took a deep breath.

“Ok, so if the buttons were worth ten, I am thinking the entire shirt has to be at least forty.” Billy said.

A couple of the guys nodded and make grunting noises, but they looked to Kirk. He was sitting back, holding his cards in a small stack and looking at Billy.

“So you want to raise me again?” Kirk said.

“Yep, what do you say?” Billy said.

Kirk slowly nodded his head and Billy tossed my shirt into the pile of money. I was scared now; I knew where this was going but I could not think of a clean way out. I thought about just getting up and running but I had the twins upstairs and then I saw my daddy’s face as he watched his baby girl masturbating. I sat still and thought.

“However, hot shot, I will call your clothing and raise you forty.” Kirk said and tossed a wad of bills into the middle.

The guys all shuffled in their seats and a few oohs and ahhs spread around. They were all looking at Billy. I turned around to see him smiling. I moved my head back and forth, pleading with my wet eyes. He cocked his head and put a pouty look on his face.

“Kirk, we will call your forty.” Billy said, looking right at me as he said it.

I felt his hands move around me and then felt him pulling at the front clasp of my bra. I moved my arms in and pressed on his hands.

“Boys, you have no idea how special this will be, you are about to see the most perfect set of tits I have ever seen in my life and you know I have seen a few. They are not the biggest in school, but they are absolutely perfect. Baby, please move your arms.” He said, staring at me.

I was openly crying now and trying to plead with him. He did not show any change in his face and I moved my arms a little. I felt the clasp let go and my bra snapped open. I turned my head to see all the guys looking at me. I felt the cool air hit my breasts and felt him sliding my bra off my arms. I moved my arm and he slid it off and tossed it into the middle. I tried to keep my arms in front, but I knew they could see plenty. I felt a tear hit the top of my right breast.

“We call.” Billy said.

Kirk laid his cards down and I saw three Aces looking at me. I knew we had lost. I laid the cards down and the table issued numerous guy sounds.

“Nice hand, bubba” Billy said and high-fived Kirk as he scooped up all the money and clothing.

“I need another beer. Baby girl, jump up and get everyone another beer. Also, I think we should class up this party a little, get us some glasses.” Billy said and tapped my leg.

I sat there for a minute and then turned my head to him.

“Move.” He said in a soft but stern voice.

I jumped up and felt my breasts jiggle a little. I had always been proud of them. They were not the largest as Billy said but they were large enough. They were a C cup and perfectly formed. They sat high on my chest even without a bra. My nipples were small and pink. Billy always said they were the cutest he had ever seen. Cute or not, the cool air had them rock hard and sticking straight out. I tried my best to hold an arm across them.

I moved to the fridge and pulled out four beers. I put the beers down on the counter and got four glasses out of the cupboard. I put a glass and beer in front of each guy. They stared at my breasts as I moved around. I stood next to Billy like a puppy my arms crossed across my chest.

“Baby, you need to be a good waitress and pour the beers.” He said.

I huffed and then opened his beer and began to pour it in his glass, leaning over the table slightly. I jumped as I felt Billy move my arm away from my chest and his hand touch my right breast. He paused and I continued to pour. He squeezed it softly and pinched my nipple. I felt my young breasts hanging free.

“Aren’t they perfect guys?” Billy said and continued to squeeze as I poured.

“They are sweet.” Jimmy said.

“Yes, very nice.” Tommy said.

I finished pouring Billy’s beer and stood up. He pulled his hand away and I moved over to Kirk. I popped his beer and began to pour. I flinched again as Kirk reached up and grabbed my breast. His hand was bigger and rougher than Billy’s. I tried to pour faster as he manipulated my young breast. I finished pouring his beer and moved quickly away. I did not get a reprieve as the guys took the lead from Kirk and Billy and played with my breasts as I poured their beers. I felt like a piece of meat.

I returned to Billy’s side. He was smiling up at me.

“You are so beautiful.” He said to me.

I crossed my arms again and just stood there as he turned to the table to pick up his cards. I saw he had crap again as none of his cards matched. I saw Jimmy toss a bill in the middle.

“Oh, we will call that one.” Billy said quickly.

He turned and grabbed the waist of my pants and pulled me closer. He looked up into my eyes and then popped the snap on my jeans. He turned back around, and the rest of the guys played. Two of them tossed money in.

I looked around to see if I could get any ideas. I could not let this go much farther; things were already way out of hand, but they were going to get way worse. I was thinking of all my options and must have started daydreaming. I was brought back to reality as Billy pulled the zipper down on my jeans. My panties were partially visible now. They were white with little blue flowers on them. They were really little girl panties; I was still small enough to shop in the Juniors department and I loved how cute the stuff was. I took another deep breath and tried to stay calm to think.

 
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