Breaking Jennifer (part 1)

After my encounter with Karen my life had changed for the better. I had a new found confidence. My attitude changed drastically. With the money I had saved, and some my father had given me, I went out and bought new clothes. I stopped in Abercrombie and Fitch, American Eagle and Banana Republic at our local mall. I bought fitted shirts that hugged my torso and showed off my toned physique. The pants I bought were tight. Not skinny jeans mind you but jeans that fit tight in my crotch and ass. I was finally proud of my body. I stopped by sunglasses inc. and bought a designer pair of shades. I even went out and got an expensive hair cut. As I walked through the halls of my school my classmates and friends saw a noticeable difference. Girls started looking at me for the first time and I had the confidence to talk to them. Even Jennifer and Brittney would talk to me from time to time in passing. I finally had swagger, all thanks to Karen bringing me into manhood. I stopped shaving everyday and kept a 5 o'clock shadow all the time. With my sunglasses, hair and designer clothes I looked like a model pulled right out of GQ. I looked like a college student roaming the halls of my high school. My classmates I could tell thought the same. I would receive shy looks from the nerdy girls, looks of jealousy from the guys and looks of lust from the sluts. Including Jennifer. Everyone knew she had been around the block a few times. I still worked hard in school and kept up with golf and band but chose to drop 4H in favor of a more active social life. Work didn't change though. The following Monday I returned to work at Taco Bravo. My first day back Karen and I exchanged looks. She winked at me in passing. She wore a turtle neck under her polo to hide the hickey I had given her. She walked with a bit of a limp. When I asked Karen what happened she whispered that it was from our romp two nights before. She let me know how good it was and how she hurt so good afterwards. Karen pulled me in the office Monday evening close to the end of my shift. "Billy you look different," she told me as I sat in her office and she closed the door. "A bit more confident I see." "Much more confident," I told her with a smile. "That's good. Women like a man with confidence and a big dick," Karen said as she felt my lap. I smiled and pushed my chair back against the door. I leaned back in my chair and unzipped my pants. I pulled out my flaccid cock with one hand and grabbed Karen's head with the other. I pulled her down to the her knees on the floor. "No no! We can't! Not here," Karen said as she got down to kneel before me. For someone who was saying no Karen did not resist me as I pulled her head to my cock. She opened her mouth and took my cock in. She made sure to suck lightly and softly as to not make any noise. As she sucked my cock I grabbed Karen's head and fucked her throat. She clenched my legs as she wanted to gag but knew doing so would alert attention. I felt her throat open and take my cock deeper. She began to gag on my cock. She finally forced her self up off my cock. She took a deep breath and grabbed the can. She gagged as she brought up thick saliva and spit it into the trash can. I thought she would be done. With thick saliva running down her chin she went back to sucking. I was about to cum when I heard a knock on the door. Karen tried to lift her head from my cock. I forced her head back down and my cock deeper into her throat. "Just a minute," I called out. Karen looked up at me with wide eyes as I continued to fuck her throat. She shook her head signalling me that we should stop. With a wide grin I nodded yes. I stood from my chair and took a handful of Karen's hair in each of my hands. I held her hair tight and brought her head against my cock as I thrusted into her mouth. Her lips were no longer around my cock. Karen's mouth was wide open accepting my cock into her throat. She looked up at me wide eyed through her glasses. I felt myself start to cum. I wanted to be bad. As I felt my first load start to leave my cock I pulled Karen's head off my dick. I let my cum fly as some went in her mouth, some on her chin and some on her glasses. "Oh Billy, what the fuck," Karen whispered. My next load went mainly on Karen's face. Some went on her glasses but most hit her upper lip and nose. As my last load sprang I pulled her head back towards me and unloaded into her mouth. She swallowed quickly as she received my sticky hot load. With closed eyes Karen felt for a napkin. She found one and continued to wipe her face hurriedly. I put my cock back in my pants and moved the chair from the door. "Don't open it yet," Karen said frantically as she wiped the cum from her face and glasses. I waited with my hand on the knob. "Okay go ahead," she said as she stood and made herself presentable. I opened to the door to find Jennifer waiting by the door. I started to leave. "Hey slut," I said to Jennifer so that Karen couldn't hear me. "Nerd," Jennifer said as she rolled her eyes. I took my place in the kitchen and continued to run my shift. After about 10 minutes, Jennifer returned from the office and back to the front of the store. It was a slow night. I finished my shift. Before I left Karen asked to see me. "Billy what happened tonight was dangerous. If anyone found out what we were doing you and I could lose our jobs and I could go to jail. Can we please only do this outside of work?" Karen pleaded. I leaned in and gave Karen a deep passionate kiss and grabbed her ass. She returned the embrace. "Sure thing," I said with a smile. "Okay now go home," Karen commanded as she pushed me out of the office. I didn't work the next two days. I had a two day golf tournament. I took second place overall. There were a few girls there who came to cheer me on. That was a first. Thursday I returned to work. It was an extremely slow night. I mostly cleaned as the kitchen practically ran it's self when we weren't busy. Tonight Karen was not in. She took a personal day so almanbahis it was up to me to run close the store. We closed at 10:00 during the week. I worked with Josh, Ashley and Jennifer. Ashley is a chubby blonde with huge tits. She orders her shirts a size too small and you can always see her bra outline through her shirt. She has a phat ass and never wears underwear. You can always see her camel toe. Usually I ogle Ashley but tonight my eyes were on Jennifer. She had her hair up in a pony tail and the black leggings she was wearing showed off her athletic body. Her tone muscular legs, her luscious hips and her sexy thighs. However the highlight of the show I was receiving was her ass. The leggings hugged her tight firm ass. Jennifer was a thinner athletic girl with a firm round ass. It wasn't a bubble butt but it also wasn't a flat ass, it was, well, perfect. Her ass moved so stunningly when she walked. One cheek would raise with each step. The left, then the right, then the left again. It would jiggle just a little. The slight amount of fat on top of the muscle moved gently. When Jennifer bent over you could see the outline of her boy shorts under her tight pants. I knew Jen had the kind of body that, if she bent over, you could see her pussy and asshole presented before you for the taking. I took in the view every time Jen bent over. Josh nudged me while staring at Jennifer's ass. "That's fucking hot isn't it," he said smiling at me. "Hell yeah, she has a fine ass," I told Josh smiling. "Too bad she's a slut that won't fuck either one of us," Josh said as he went back to work. "Yeah," I replied. I began to think. I thought about how just last week Jen was rubbing her ass against my cock by accident. I remember cumming hard in my pants. I thought about how just a week ago I was a virgin when that happened. I started to get a little hard. I went to the back of the store to keep myself busy. I began to do some dirty dishes. Out of the corner of my eye I saw Jen walk past me to storage. I continued my work. Next I knew I felt a presence beside me. I looked up a little startled. Jen was uncomfortably close. I watched her take a quick look around the area and felt her reach for my crotch. She grabbed my cock through my pants. "You know for a nerd you're not very smart," Jen said with a smile. I looked up at her shocked, confused, aroused and a little mad all at the same time. "What the fuck are you doing," I asked her as I checked to make sure no one was watching. "No girl rubs her ass against a guy like I did accidentally. I was getting a nice feel of that cock," Jen said as I felt her begin to unzip my pants. "If I knew you had been packing something this impressive I would have been nicer to you a long time ago." I looked at Jen. She had my zipper completely down. "You can't handle this cock," I told her in confidence. "Oh please," Jen said reaching into my pants. "If Karen can handle this cock I know I can." I stopped what I was doing as my heart sank. I looked up at Jen with a worried smile. She had a wide grin spread across her face. "Oh yeah, I know. That office door doesn't close right. I watched everything through a crack in the door," Jen said with a devious smile. "Don't worry I won't tell anyone. Well that is, as long as you fuck me. Although even if I didn't have any dirt on you I'm sure you wouldn't turn me down. I see how you look at me." St this point Jen's hand was completely inside my pants. I decided not to wear underwear today. Jen had her hand wrapped softly around my cock. She gently stroked my cock. "You want me to fuck you?" I asked knowing the answer. Jen just smiled. "Fine," I said. "We are both off tomorrow. My mom will be out with friends. I'll pick you up tomorrow and bring you over to my house. Then I'll fuck your brains out." "Fine," Jen said removing her hands from my pants and zipping me back up. Before Jen could walk away I turned to her. I reached out and grabbed her pussy. My fingers began to push the fabric of her pants and panties into he slit. She gasped and her mouth opened. "I'm gonna fuck you so hard you won't be able to walk straight for a week. You won't want any other dick after you've had mine," I told Jennifer in a commanding voice. I could feel Jennifer was wet. It was seeping through her pants. I gave one more grab as my fingers reached inside her. Jen just looked at me with lust and anger as she turned and walked away. I looked down to see my cock rock hard. I was looking forward to tomorrow night. The next day I anxiously awaited the end of the school day. I had big plans for this afternoon. I wanted to make this a fuck that Jennifer would never forget. I had asked my dad for some money and he had given me $150. I knew Jennifer had been around the block a few times. It was going to take some kinky shit to make this night memorable. After what Karen and I had done I had high hopes that my second time would be even better. Finally 3 o'clock came. Instead of heading home, like I do every other day, I drove ten miles to the next town over. In that town was a special shop called Venus's Workshop. It was a store that sold sexually provocative materials. It was a store for people eighteen or over. I hoped that I would look age appropriate. I had never been to a store like this so I wasn't sure if they would ask for I.D. I arrived at the store. I donned my sunglasses and fixed my hair. I thought I looked at least eighteen with my new look and fashion sense. I got out of the car and walked to the door. I took a deep breath as I saw the "Must be 18 or older" printed on the front door. I opened the door and walked in. I heard the door chime as I passed through the threshold. As I scanned the store I saw the front area strewn with wire shelves. The shelves held various magazines and DVD's. A sexy cop outfit, nurse outfit and school girl out fit were donned upon mannequins with large breasts. A young man with plugs in his ears and arms covered with tattoos stood at the counter. He raised almanbahis yeni giriş his gaze from the book he was reading and smiled at me. "Hello. Welcome to Venus's Workshop. What can I help you find today?" he asked. "I'm not sure. I'm just looking right now," I replied a little nervous. "Okay. Well if you need any help just let me know. My name is Sean and I'll be happy to assist you," he said as he returned to his book. I pondered the store. I looked through the various magazines and movies. They had every category imaginable. Blonde, black, BBW, MILF, gay, lesbian, Asian, BBC, anal. You name it they had it. I picked up a 40 DVD and looked at it. 'Thirty dollars!' I said to myself. 'Why would anyone pay that when they can see it online for free?' I smiled and chuckled a little as I put down the DVD. I made my way to the back of the store. I walked through a curtain and found myself in the sex toy section. There were dildos everywhere. Glass ones, plastic ones, vibrators, ones that looked like real dicks, big black ones with veins. I felt a little uncomfortable and lost. As I scanned the store I realized I was going to need some help. I walked up to the counter. "Sean right?" I asked. "Yep. How can I help you today sir?" Sean asked as he closed his book. "I have a very special date tonight. I want to make it special. I'm not sure what to do but I want to spice it up a little. Well actually, a lot," I said as I rubbed the back of my neck. "Well what did you have in mind?" Sean asked as he leaned over the counter. "I don't really know," I said pondering the question. "Well let me ask this how old is the girl? I'm guessing about your age, sixteen or seventeen am I right?" Sean asked smiling. "Uh..." I said not knowing what to say. "Don't worry I don't care how old you are. That eighteen and over is on the door for legal reasons. I won't tell," Sean said as he smiled big. "She's seventeen I said," smiling in relief. "Well here let's look around," Sean said as he walked from behind the counter. I followed Sean to the back room. As we walked through the curtain I found myself back with the dildos. Sean turned to look at me. "A sex toy perhaps?" Sean asked pointing to the dildos. "No, I want my dick to be the only dick inside her," I said looking around. Sean laughed. "Fair enough, I can understand that," Sean said as he chuckled. Something caught my eye. "How bout this stuff. Tell me about this," I said gravitating to the other side of the room. "Ah! BDSM gear," Sean said. "Good choice!" Hanging on the wall was a plastic package with a pair of wrist restraints and a blindfold. I thought about tying Karen's hands behind her back with her pants and how exhilarating it was. I imagined doing the same to Jennifer but with what was in front of me. "How much is that?" I asked. "The blindfold and restraints? They are $25. However I have a better deal over here," Sean said as he led me a few feet away. He handed me another package. Inside was a blindfold, wrist restraints and ankle restraints. Included were ties to attach them to the bed. "This is my last one and we aren't carrying it anymore. it's supposed to be $50 but I'll give it to you half off. It will make it the same price as the other set. I want to get rid of it," he told me as I held the package. "Deal!" I said as I handed him the package to hold. I continued to look around. The next item caught my eye. "Candles?" I asked confused. "These candles are special," Sean stated grabbing one from the shelf. "These candles have a wax that have a lower melting point. You use them to set the mood then you can poor hot wax on your partner. The wax is still hot but it's safer to use. They are $5 a piece." "I'll take two," I said grabbing another. "For your special night I will do two for $7.50," Sean said smiling. "Awesome thanks," I said grateful for the gesture. The next thing I saw I was somewhat familiar with. It was a riding crop. I had seen one used in a movie once. The mature woman was spanking the young man. I thought about spanking Jennifer with it. The thought turned me on. I grabbed it and handed it to Sean. "Okay," he said as he took it from me. I continued to wander around as Sean headed back up to the counter to put my things up front. I heard the door chime. I heard Sean helping another customer as I browsed. I with everything I had I was only spending $52.50. The riding crop was $20 and I got a great deal on the candles and restraints but I had plenty of money and wanted a little more. I fantasized about what I wanted to do to Jennifer. How I wanted her to remember tonight. How I wanted to make her cum. I realized through my fantasy that being in control really turned me on. I knew from watching porn that I was what they called the dominant. Sean returned to the backroom. "Sorry about that," he said. "You're fine," I said staring at the products. "What else would you like," Sean asked as he stood next to me with his hands in his pockets. "I don't know. I want more but I don't know what I want," I said looking at him. "Well let me ask you this," he said as he paused. "Are you planning to use this stuff on her or her use it on you?" "I want to use it on her," I said confidently. "Okay I have an idea," Sean said as he walked to a case in the corner. He grabbed out his keys and unlocked the case. He handed me a small package that held a little blue thing that looked like an egg. "That's called a bullet. It vibrates at a very high frequency. What is nice about this is you can use it in two ways. You can place it on her clit and it will make her cum or," Sean said as he paused with a smile. "You can bring her to the brink of orgasm with this and then take it away leaving her wanting release." I quickly looked at Sean. I paused then smiled. "I take it the latter interests you," he said with a smile. "I'll take it!" I said. Sean closed the case and took the package. "This is $50. I can't budge on price for this. It's a top seller," Sean said as he held my new almanbahis giriş toy. "That's fine," I said. "Anything else?" Sean asked. I thought about anything else I wanted to do to Jennifer. I felt ashamed as I had a hard on in the middle of the store. I hoped Sean didn't notice. Though. even if he had, I think he's probably seen this type of thing before. "No, I think that's it," I said. We began to walk back to the counter so that I could purchase my things. As we got to the curtain one more case caught my eye. "What the hell is that?" I asked as I blindly walked to the case. Inside the case were theses glass pear shaped items with little stands. I had not seen these before in any of the movies I watched. I was intrigued by them. "These are butt plugs," Sean said as he smiled seeing my awe. "Butt plugs?" I said confused. "Yep. You put some lube on these and slowly slide them into your lovers ass. You can use them for stimulation or you can use them to prep your partner for anal intercourse," Sean stated. I thought about the idea of putting this "butt plug" in Jennifer's ass. God I loved her ass. I though would she let me? Would she enjoy it? Would I ask for her permission or just try it and wait for her to tell me to stop? I was deep in thought. Then I started to fantasize as I thought about Jennifer restrained to my bed. I begin to pour wax on her lower back. As she moans in pain and pleasure I grab the butt plug and slide it slowly into her ass. She moans and takes it. I snapped back to reality. "Okay I'll take one," I said enthusiastically. Sean opened the case as he chuckled and grabbed a clear glass one. He closed the door and locked it. "This is also $50," he said as he walked up to the counter. "Ooh, never mind I don't have that much," I said embarrassed. "How much do you have?" Sean asked holding the package. "$150," I said pulling out my cash. "Don't worry I'll take care of you," Sean said with a smile. I followed Sean to the counter. He began to ring up my items. Once he was done he fixed the price on the register to read $150 exactly. "Do you have lube?" Sean asked. "No," I said. Sean reached under the counter and pulled out a small bottle of clear liquid. "This is lube. Use this before you use the butt plug or entering your partners rectum. It will help with the friction and reduce pain. It will make it more enjoyable for you both," Sean said as he put the bottle in my bag with the other items. "This bottle is on me." "Are you sure?" I asked. "I'm the owner of the store of course I'm sure," he said with a chuckle. "Thank you for your business and have fun tonight. Sean gave me a wink. I thanked him and headed out of the door with my black bag full of goodies. I jumped in the Mazda and made the trek home. I had a hard on all the way home. I was so excited for tonight. When I got home it was 5:30. I wanted to go pick Jen up at 8 o'clock. Mom's Malibu was already gone. I knew she wouldn't be back til well after midnight. She was always out late when it came to girls night out. I headed to my room with my toys. I opened the restraints first. I investigated them to see how they worked. I practiced on my own wrists and ankles so that when the time came I had no trouble using them on Jennifer. I hid the restraints and blindfold under the bed. I took the restraint connectors and attached them underneath the bed. I then pulled out the riding crop. I bent it in my head. I bent it then let it fling out of my grasp. It made a satisfying whoosh sound. I slapped the bed with the end. It make a slight crack and I became aroused. I thought about it hitting Jen's rear and the sound it would make. I hid it under the bed along with the restraints. I grabbed the bullet from the bag next. I removed it from the packaging. I examined it. I found the switch to turn it on. It began to vibrate in my hands. I could see why this is a great seller. It must feel great. I couldn't wait to use it on Jennifer. I undid my pants and put it against my cock. I bent over in pleasure. "Holy shit!" I said underneath my breath. That felt amazing. I could just imagine how it would feel on Jennifer. Finally I removed the butt plug from the packaging. I held it in my hand. The glass was cool and smooth. I grabbed my phone and looked up a video of sex with a butt plug. I watched the actress spread her cheeks as the man slowly twisted the plug as it slid into her ass. He pushed in and pulled out slowly working it into her tight hole. I noticed he didn't try to slide it in all at once. I saw the girls ass shine with lube. I realized that the lube was applied to her hole not the toy. Good thing to know for later. I hid the plug and the bullet in the top drawer of my dresser underneath my socks. After gathering the packaging I headed to the kitchen to throw away my trash and jump in the shower. I looked at the clock as I gathered my clothes for the evening. It was 6:15 I decided to jump in the shower and get ready. I had special grooming plans tonight. I knew girls like a guy who was well groomed down below. I opened a new razor blade and attached it to my razor. As I turned the shower on I got my body wet. I grabbed my shaving cream and applied a hefty amount to my genitals, I slowly began to shave the dark brown hair from my nether region. I was care as to not cut myself. Once I was happy with the smoothness of my area I began to wash my body. I was not going to masturbate at all tonight. I wanted as much cum as possible to give to Jennifer. I washed my body and hair thoroughly. I turned the water off and stepped out of the shower. I applied my deodorant and made and dried my hair. Upon leaving the bathroom I looked back to the clock. 6:45! Shaving my nether region took a bit longer than I thought. I headed up stairs to my room. I finished drying off. I grabbed my new candles and set one on my night stand and one on the dresser. I began to get dressed. I decided to wear a a tight pair of American Eagle jeans. They were so tight that you could almost make out every detail of my cock against my leg through the thin material. I buttoned and zipped the jeans not donning any underwear. I adjusted my cock inside my jeans. I grabbed a black button down long sleeve shirt. It was tight to my body.