Jessica's First

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.