A Dark Street

I found myself the young excited mistress to an older guy. He seemed to have the world in his hands, how I wanted to be near him! He had the life I only dreamed of, still living at home, no cares or responsibilities with no one to account to.

I had little sexual experience before him, mostly consisting of hurried groping. There was one boy before him, whom I gave up my virginity for. Unfortunately for me, it was little more then an embarrassing confusing, very short experience which left me wondering how there was an overpopulation of people in the world!

Then I met Lance out walking along a dark street in my neighborhood. I had been feeling restless and angry, so I was glad for the company. We walked and talked for some time about inconsequential things, passing the time as lonely strangers often do. I did not see him after that for some time, although I took many more walks hoping to meet him again. The next time we met, things progressed quickly from our talk of weather, and human nature.

Soon I was in his arms, feeling the lust and desire of a more experienced sort. He had little patience for my inexperience and soon took charge, showing me exactly what he wanted and expected of me, and how. We met this way often, and I learned how to please him still knowing little of any pleasure for myself. I simply knew that he wanted me, wanted to possess and keep me.

We were comfortable in our routines, and roles. I did what he wanted, and he wanted me around. Soon we found ourselves talking during sex, normal everyday conversations as if nothing was happening. I had become an outlet, a release for the frustrations of his day. I was his quiet, and docile lover, demanding nothing and taking him as he offered.

One day, however, he was especially excited and I was to learn why in short order He took extra time, to make sure I was excited, wet and ready for him. He fucked me in a lazy almost distracted way, slowly. Then he slowed even more yet, and to my complete surprise pulled out of me, still hard and now glistening, my wetness coating his cock. "Wait there, and finger yourself for me." He said as he got up, moving about in his room. I was deeply embarrassed and maybe even ashamed, to do such a thing, when he could come back and see it I reluctantly did as I was asked, figuring he knew more then I did about sex. Oh, was that the truth!

He returned a short minute or two later, with something in his hand. I wanted desperately to stop touching myself, but continued in fear he would think I didn't know how to please him. He would not show me what was in his hand, simply telling me to move my hand away and open my legs for him. Blushing, I let my legs fall open again realizing they had clamped closed over my hand, trying to hide what I was doing.

I felt something very cold and smooth slip inside me, it was much smaller then his cock and felt very strange and foreign. I squirmed, trying to sit up and look, but he would not let me, and pushed me back until I was lying down again. Fear and confusion twisted in my brain as he pushed this object in and out of me. Against everything that seemed normal and rational to me, it started to feel good. My hips, much to my embarrassment began to rise and fall with his thrusts, my breath quickened and my eyes closed.

As he saw my body react to his toy, a devilish grin spread across his lips and he told me to turn over on my hands and knees. We had fucked this way before, and although it had not become my favorite position yet, I was willing. He laid out a blanket on the floor for me, so it wouldn't hurt our knees and pushed me down the way he wanted me to be. My ass in the air, despite my willingness, made me feel exposed and vulnerable. Exactly how much so, I was yet to learn.

He pushed the small object from earlier back into my pussy, and started fucking me with it again. Then I felt something that startled and excited me in a most forbidden way. His hard cock was nestled between my ass cheeks nudging up against my tiny virgin asshole. It felt slippery, sticky, and impossibly huge.

The pressing threat of pain, was like an oaks mighty roots reaching deep into the earth. Suddenly in an explosion of pain and ecstasy I felt my body opening up to him, and his fat cock was deep within me. I collapsed onto the floor, my arms giving out beneath me. With the force of his thrust, his weight must have followed me, but I could not feel it. The world had gone black, I passed out from the immense pain of his cock forcing its way into my tight little asshole.

I awoke, what must have been moments later, my ass throbbing, sending white hot searing pain throughout my senses with my face wet and tears blurring my vision. He seemed scared as well, and holding my head in his lap, caressing my hair. Only his cock betrayed him, resting near my lips, shiny and hard, mocking my weakness.

He held me and touched me and brought me back to passion, despite the lingering pain spreading out like fire from my stretched hole. After penetrating my pussy, with long slow strokes, he asked me quietly if he could try again. He wanted to put his throbbing cock back in there! He told me there was another way we could do it with me laying on my side. Maybe that would not hurt as much. He asked me but without question, "just relax for me, I will hold you and be gentle this time", all the while his cock slid seductively in and out of my pussy.

I was confused at why he wanted that so badly when he was already inside me. Once again my insecurity rose I was so scared he would not want me after this, if I didn't let him. He laid me on my side, and curled up against my back, his cock pressing in-between my as cheeks once more. I shook as I remembered the pain in it's full extent, still persisting where he rest against me.

He took what must have been Vaseline and coated his cock again this time spreading some on my ass too. I felt the small hard thing pressing into my pussy first, shortly followed by his large cock trying to intrude on my asshole. He lifted my leg, and held it in the air, as he forced his cockhead into me again. This time, it went in, not without a lot of pain, but easier then the first time. He froze there only momentarily as I began to cry, pushing his toy in and out of my pussy. He didn't wait long though. With me, still crying he began to thrust in and out of my stretched, torn asshole.

He paused once a few minutes later, to smear more of that lube on his cock, never pulling completely out. Then resuming his thrusts long and slow in my little hole. He couldn't cum there and pulled out of my burning, torn ass, and turned me onto my back to take my pussy again. He took me then with angry pent up passion. With short pounding strokes, he fucked me, hard and fast. My legs, stretched over his shoulders were burning with each time he came down onto me. I hurt now, in both holes, feeling violated, used, and strangely wanted. In my pain mixed pleasure I didn't know if I wanted him to stop or fuck me harder.

As if to decide for me, he finally came, shooting his hot cum deep inside me. The bulk of it came sliding back out of my abused hole, soothing and moistening my torn asshole. He lay there for a moment, cock softening inside me, panting and sweating, trying to catch his breath before finally moving off me. I scrambled up to find my clothes and cover myself in the small protection my clothes could offer me. As I got dressed I saw the small, smooth hard thing, he had been fucking me with. It was a test tube out of a science kit.