Babysitting Blues

Story Info
Young woman falls victim to sinister plot.
15k words
4.36
245k
114
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

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 25 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 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 18th. 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 and they were only about an hour away if I ran into trouble. Anyway, 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 five 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 senior.

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 last Saturday night. 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. 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, 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 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.

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 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 and then my stomach. I held his head in my hands. I was letting myself go. 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, 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 slightly 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 to stop or I would regret this moment for a long time. I sat up. He got angry then and I remember hearing the words "prick tease" and "leading him on". That discussion was not pretty and ended with him tossing me out of the car. I stood there 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 had 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 said 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 who the other two were 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, my right hand between my legs. My left hand was squeezing my 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 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 to create an entire website. I especially like the scenes of you and I on your bed. 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 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.