0 comments/ 45218 views/ 1 favorites Jessica's First By: Jargon I am older and more experienced now than I was at that time. He was my brother's best friend, and by all standards, he was not that handsome. He was chunky, had a horrible haircut, but, growing up around him, I had come to love him, first as if he was my brother, then, as time progressed, I realized, I loved him a woman loves a man. I am not a beauty queen, but I am also not ugly. I am tall and just under 6 feet, waist length brown hair, and a full figure. But, all you horny people don't care about looks, you just want to hear the story, so here it is: My brother was at work. I lived in the house that he and his best friend James rented while they went to college, lucky me, I went to the same school as they did so it was a pretty easy decision that I move in with them. I had been sitting in the Jacuzzi that was built into the house, thinking how lucky I was that James was rich, and he is the reason I lived in this lap of luxury, and then, my thoughts turned dirty, as they usually do when I think of guys, as I sat there fantasizing about the things I would like to do to him, and the things I would like him to do to me, a storm rolled in, lightning flared in the distance, and I knew it was time to get out. Throwing on my robe, I went to my room, which is on the second floor, passing by James' room, he was just laying there, staring at the ceiling and listening to the sounds of the storm, which he claims, lulls him to sleep, I paused briefly to watch him, my eyes drawn to the crotch of his blue jean shorts. "Decided to go to bed Jessica, or are you going to be going out later tonight?" His voice snapped me out of me revelry and I quickly answered him with a shrug and a coy smile, laughing inwardly at his confused expression. Hurrying into my room I took of my robe, water dripping off of my body, from my skin and my bathing suit. The bathroom was on the other side of the hall and I figured I could just grab a towel from there, after I had draped my bathing suit over the curtain rod. My feet stamping on the carpeted hallway as I moved to the bathroom, pausing briefly at James' doorway, looking in to find him asleep. My bathing suit hung up, I looked into the linen closet, there were no towels in there and I cursed, remembering today was supposed to be my laundry day. Closing the door, to the closet, I looked at my reflection in a mirror, my nipples had hardened from the combination of cold air and water, and my pussy looked nice, I had shaved it when one of my girlfriends had jokingly compared it to a Chia pet with black sprouts in the locker room. It wasn't a long way from the bathroom to my room, and with James asleep I had nothing to worry about, but as I passed his room, I had another fantasy, looking at him on his bed, I imagined me on top of him, riding his cock. I began to rub myself between the legs, letting my fingers get coated in my own lubricant, I lifted them to my lips, and gently sucked the shininess from them. Building up my courage, my horniness at it's peak, I moved into the room. James was still wearing his jean shorts, so I gently unbuttoned them, zipping them, down, excited by the prospect that James was still sleeping, resting up for his rendezvous with my brother later on. Looking through the slit of his boxers, I saw his cock, it was even bigger than I had imagined it. Reaching in, I touched it tentatively, hearing James' groan and stir, I continued to play with him using my hand, my finger went to his lips to silence him. He looked down at me, playing with his hardening cock and I saw want in his eyes, and I knew that he wouldn't try to stop me. Moving slowly downwards, I kissed the tip of his swollen head, flicking my tongue over it, I could taste a bit of soap and knew that he had showered not long before I had come out of the Jacuzzi. I wrapped my lips over his cock, moving up and down with my mouth, my tongue stoking him. His head lay on his pillow, I moved so my legs were on the sides of his head, my pussy resting on his mouth, all the while working him with my hot mouth. His tongue, I still remember the feel of it, the first time I had ever felt it down there, it made it's way into me, even as his hands played with the outer lips of my crotch. So caught up in this, I barely noticed as he began cumming in my mouth, as some dribbled down my chin, I began a game of catch up, trying to swallow whatever was still being sprayed in my mouth. I was shaken to the bone, the orgasm tore through me, and I drenched his face with the hot liquid that rushed from the inside. Taking my lips from his cock, I turned to him, lust still apparent in his eyes, as I am sure now it was in my own, I leaned forward to kiss him, his cum cooling on my chin, I took a wiped half of it off with my finger, backing my face away, I licked it off. His own finger came up, and wiped away the other half, which I promptly removed with a hard suck. I kissed him hungrily, his tongue venturing into my mouth, I straddled his hips, surprised that he was hard again so soon, I guided his cock with my hand, letting it into my tight slit, with two or three thrusts, he had massacred my hymen, making me moan in pain, combined with great pleasure, but this was not what he wanted, with an almost violent motion, he tossed me off of him. Moving me so that I was bent over the side of the bed, my rear in the air, the crack spread to show him my tight ring, he guided his barely lubricated cock to it, thrusting hard, he was in charge and he knew it. He instantly broke through the ring and I let loose a scream of pain. He didn't care though, he moved back and forth, stretching the muscle, till there was no more pain, only it's memory. The filling sensation was awesome, as he moved back and forth, my fingers playing with my clit, and suddenly there was more pain, he widened impossibly more with orgasm, pumping my ass with his hot cum, I orgasmed once more, and then it was over. I slowly woke up from sleep, still exhausted. I heard the shower, I knew where he was. The cum was leaking from my ass, drying, as I stood and moved to the bathroom....... That was long ago, not the best of sex, but okay. Maybe if I get the courage, I'll tell you what happened a few days later. I can still taste my brothers cum, mingling with that of James. Jessica's First Day “This is Jessica. She’s starting today. I want her to listen to the conference call so I told her that she could sit with you.” I usually did not bother to look up when my boss would burst into my office with some new rant or order, but the mention of a girl’s name caused me to at least look up from my computer screen. Jessica was a big, tall pretty girl with blonde hair. The first thing I zeroed in on was her 44DD chest. She was wearing a low-cut purple top that showed everyone plenty of cleavage. She gave me a big beaming smile. I gave her tits a good stare before saying, “Sure. I don’t have an extra chair so you’ll have to bring one in.” They both left and Jessica returned, rolling in a chair. She rolled it right next to me. I gave her a brief smile and began to dial in. She nervously tapped her pen on the notepad that she had brought with her. “You probably won’t need that. These calls are usually pretty boring and you don’t learn much,” I told her. “Okay,” she said, putting the pen and pad down on my desk. “I’m just pretty tense because this is my first day and all.” The call began and I resigned myself to not getting any work done with the new girl hanging on every word that was said. I settled back in my chair and tuned out the droning reports. I looked over at Jessica. Her hands were fidgeting a mile a minute since I told her she did not need to take notes. “You can relax,” I said, “Consider this a break.” “I really need something to do with my hands. I’m just so nervous,” she replied. With that she reached over and put her hand on my leg. I stiffened and felt a twinge in my pants. She began running her hand up and down my leg. She edged ever closer to my hardening dick. Her widening passes finally brushed up against it. I think she found what she was aiming for. She began to unbuckle my belt and take my pants down. I did not resist. I did begin looking for hidden cameras, as I could not believe this was truly happening. I lifted my butt up as she tugged at my briefs. Now I sat exposed from the waist down. Jessica’s eyes looked a little glazed over. She looked like she was still intently listening to the conference. She seemed to be staring into space but she looked very content. Her movements felt like they were on autopilot as if this was something she did everyday. At that moment, I did not really care. Jessica began stroking my cock moving from the base slowly up to the head. Each bump on my dick felt like it was receiving it’s own personal massage. I noticed that her nipples were growing with each pass of her hand. They poked out of the tight material. They looked to be a half inch long. I reached over and gave one a little pinch. She barely reacted to my touch except to push her chest into my hand, filling it with her breast. I took the opportunity to bring my other hand to squeeze both of her beautiful breasts. They were much bigger than any other boobs that I had been able to hold. I decided to go for all I could. I stood up in front of her. She never let go of my cock as I repositioned myself in front of her. I bent down and grabbed the bottom of her shirt. I pulled it up over her head. She was forced to briefly let go of my cock to get the shirt off but her hand returned immediately as if magnetized to my cock. Jessica now sat in front of me and stared at the cock in her hand. She continued her stroking with no apparent end in sight. Her other hand cupped my balls and she slowly played with my sack like two ben-wa balls. I stood over the huge cleavage that was formed by her bra. I stared at the two huge mounds of flesh in front of me before slipping my hand in her bra. I immediately went to grab her protruding nipples. Her eyes closed as I rubbed her nipples between my fingers. I felt my orgasm building quickly. Releasing one hand from groping her tits, I pried her fingers off my cock. She looked disappointed. I scooped her tits out of her bra. Their size caused them to fall out heavily. I kneeled in front of her and shoved the two breasts together around my face. Engulfing my face in her tits, I licked and sucked as much as I could before standing again. I took two handfuls of her breast and slid my dick between them. Jessica helped by sliding out of the chair. She now knelt and held up her breasts as I humped her chest. I looked around for something to shoot into. I attempted to reach a box of kleenex that was just out of my reach. Seeing what I was trying to do, Jessica had a solution of her own. She grabbed my cock again and placed it in her mouth. She sped up her jerking. Between her rapid stroking and the wetness of her tongue, I began spewing down her throat. She swallowed every drop. Nothing spilled out as she milked the rest of my cum into her mouth. I pulled up my pants. Jessica tucked her breasts back in her bra and put her shirt back on. She did not say anything and just smiled. The phone call had been over for some time. Just as we had returned to our chairs, my boss came in. “How was the conference call?” she asked. “Did you understand everything, Jessica?” “I think she’s going to catch on just fine,” I said. “Yeah, I think Tom will be a good teacher for me. Do you think he could train me?” Jessica asked. “Sure, I guess. Is that okay with you, Tom?” Was it okay? I couldn’t wait!