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A Night to Remember…NOT!

A Night to Remember...NOT!
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During my freshman year in college I was unsure of myself in many ways. It was the first time away from home, although that in itself wasn’t a big concern. I had been pretty much on my own throughout my high school years. Both of my parents had important careers, and I was the youngest of three. My brother went away to school when I was in 9th grade, and my sister left the next year.

I had lost my virginity a while before college, one of those choices you later look back on and wish it had been different. Actually, I didn’t regret losing it, just the circumstances around the way it happened. What I had fantasized as a wonderful experience turned out to be very unpleasant, and the beginning of a series of heartbreaks.

The guy I had fallen desperately in love with was incredible in my little fantasy world, but a real asshole when I could finally see the truth. He was two years older than me, and in my view, a real man of the world. I was willing to do anything for him, and could think of no greater gift than my womanhood. For almost two weeks before it happened I had planned and schemed how to make the night special. My parents would be out of town, so there wouldn’t be any questions about why I didn’t come home that night.

I had just turned eighteen the week before, and we were going out for a special night. I secretly planned to end up in a motel room; he didn’t have a clue. Dinner was a dream. We had both dressed nicely for the occasion. I borrowed my sister’s prom dress, and secretly wore under it the most alluring lace teddy I could find. My breasts are naturally small, so I wanted something to emphasize them as much as possible. The small pinkish nipples peeked through the lace as I was getting dressed, and I knew that he would like it.

All during dinner I teased him, making sure to hold my hand to his thigh under the table, every now and then straying to rub across his throbbing crotch. Although we had planned to go to a movie afterward, that never happened. As soon as we got to the car, he was all hands. A little rougher than I had expected, but understandable after more than an hour of teasing.

Since it was getting toward dusk, I suggested that we park down along the lake and watch the sunset. He didn’t seem too thrilled by that because he had other things in mind. But so did I, and he would see the light soon. By the time we found a quiet place, I had already worked myself over to him and had my hands inside his unzipped pants. Feeling his hot, moist cock throbbing in my hand really turned me on more. I began to stroke up and down as he loosened his belt, and it drove him wild. I kind of knew what to do from secretly watching some of the videos my brother had hidden in his room, and I tried my best to imitate the women I had seen there. It seems that the guys on the videos last forever; but not so in real life. In less than two minutes I was trying to catch a load of sticky cum and not get any on my sister’s dress. Stamina was not one of his strong points. Actually, I thought it was a sign that I was very special to him.

I don’t remember the sunset, because we were busy. The lace teddy was actually a hindrance to his wandering hands, a little frustrating at the time. When I finally asked if we could go find a room, his eyes lit up like a Christmas tree. After almost two months of putting him off, here I was actually asking him to be my man.

Now, I had romantic dreams about how wonderful this night was going to be. All the women in my brother’s videos just loved everything that their men did to them.

Watching them moaning, begging for more, screaming how wonderful it was, and more had fueled my fantasies for this night. I have to admit that more than once I had masturbated in fantasy over the videos, waiting for this night. If my own hands could give me so much pleasure, how much more I expected from him! Without realizing it, I was rubbing my own crotch as we drove to the motel. By the time he came back from signing in, I was hotter than I had ever been.

We walked to the room pressed so close together that it almost hurt. An older couple was walking out of the room next to ours, and I wondered if they thought we were newlyweds. Wouldn’t that be great? I mean to actually be Mrs. … I was sure that this was forever.

As soon as we got inside he began to pull my dress off. I know I had gotten him really turned on again, but I was still fantasizing of a tender loving moment as I yielded myself to him. The dress fell to the floor and I tried to step away so he could see the lace teddy. I was a little hurt when he didn’t seem to care about how I looked in it, just wanted to pull it off and get it out of his way. There I stood, naked before him, his hands roughly exploring everything he could reach. I began to unbutton his shirt as he pushed me back onto the bed. He was on top of me, fully dressed and panting like an animal. I have to admit that his forceful passion was turning me on more. He kissed me deeply for several minutes while he continued to touch me everywhere he could. But his weight was having its effect on me and I had to roll him off so I could breathe.

As I began to unbutton his shirt he moved his mouth to my breasts. No longer able to reach his buttons, I held the back of his head tight against me as he engulfed my entire left breast in his mouth. I had never felt anything like that. I almost came right there. He moved to my other breast and again engulfed it entirely. His hand took my left breast and he began to roughly tweak my nipple. Actually, that hurt, and distracted me enough that I pulled away.

I quickly sat up and began to unbutton his shirt again. This time he lay there and cooperated. I was really looking forward to running my hands all over his smooth chest. I don’t know why, but guys with hairy chests are a turnoff for me. His was fantastic. His well developed abs and pecs soon had me back in ecstasy. I kissed him everywhere, licking his salty skin as he trembled under my touch. What an incredible feeling to have this power over my man!

While I was keeping him on the edge like this, his hand found its way down to my secret parts. I was really wet by now, and he slid his fingers all over the slippery lips that held his prize. I had trimmed everything up nicely hoping to entice him. Actually, I’m not sure he even noticed. As I began to open his zipper, he tried to plunge a finger inside me. If stamina had not been his strong point before, gentleness was not his strong point now. I had never had anything inside me in my life. When I masturbated I had always just pressed and rubbed the outside of my vagina. I was so tight, and nothing had prepared me for this sudden pain. I tried to pull back, but he had a tight grip on my ass and held me. It was not until he decided to roll back to finish taking off his pants that he let loose.

Now I started to get scared when I saw the size of his cock in comparison to his finger. I would later realize that he was not by far the biggest man in the world, but that night it looked like a monster organ. By later comparisons, his 5 and 1/2 inches wasn’t all that big, but to me, for the first time I had really been close to a cock in real life, it seemed huge. The circumcised head was a deep purplish red color, throbbing and jerking as I watched in awe. Drops of precum made it shine in the dim light of the room. I reached out to once again hold him, like I had done in the car. I never got to that because he roughly pushed me back down on the bed. The look in his eyes was something I had never seen before and I was really scared!

He forced my legs apart, got on top of me, and instantly began to force his monster cock into my now tender vagina. What I had fantasized as a tender, loving moment was now going all wrong. I tried to move into a more comfortable position to open myself to him, but my shoulders were pinned motionless by his strong hands resting on them as he rose up over me. As he began to press his manhood into me the pain was incredible. The only words I could get out were “Please, No!!” He acted like he didn’t even hear.

He rammed his raging head against the fortress of my virginity, slamming again and again into the unyielding gate. Reeling in pain I cried and pleaded “Please, NO!!!” again and again, but it only seemed to enrage him. Harder and harder he slammed, making a little more progress in his attack with each vicious thrust. My whole body was quivering and I felt on the verge of passing out.

Suddenly he slowed for a moment, then rammed harder than I ever thought possible as I felt his throbbing rod break past the guardian of the gate. Pushing into me fully, the pain was indescribable. Gone were my fantasies of a tender moment when I could hold him close and tell him I was now truly his woman. I had never seen this in any of my brothers videos. I felt that I was doing something wrong to experience this much pain.

As he dropped his entire body weight on top of me and began thrusting in and out ,grunting like an enraged bull, I started to sob uncontrollably. I don’t know if it was from the pain, the humiliation at having failed so miserably, or both. After what seemed like hours, but was probably no more than two minutes (Remember? He had no stamina! Thank goodness!!!) he began to shake, and I knew he was cumming inside me. At first I felt relief that my ordeal would be over, but that gave way to terror when I remembered that the condoms I had brought for him were still in my purse in the car!!

Crushed under his weight, I began sobbing and wailing harder than before. If I was hoping for sympathy from him, I was crushed again. As he rolled off of me he had a disgusted look on his face and said “Now what the fuck’s wrong with you?” I don’t know what was worse: the physical pain from his penile assault on my torn vagina, the fear that I might be pregnant, or the humiliation of his anger. It was almost fifteen minutes before I could stop sobbing long enough to even speak. During this time he got up, went into the bathroom to piss, then got dressed. So badly I wanted him to hold me and comfort me, but he just turned on the television in the room and acted like I wasn’t even there.

Finally he stood up and said “If all you’re going to do is whine, I’m going out for a beer.” I freaked out, and with what strength I had left I got up and started pounding his back as he started out the door. He turned back, pushed me onto the bed and said “Get a grip.” Then he walked out the door and I heard his car pulling away.

I gathered myself together after another long sobbing attack. I put my sister’s dress back on, feeling that I was somehow unworthy of it. After all, her boyfriend treated her like a queen. What was wrong with me? I threw the lace teddy in the trash can. So much for feminine allure. That brought a fresh wave of tears to me, and I collapsed onto the bloodstained bed (Actually, it wasn’t as stained as it seemed to me at the time).

When I finally got myself back in control I called my sister, who was in town with her boyfriend for the weekend. They came and drove me home, and finally gave me the comforting care I needed so badly. Her boyfriend was so sympathetic, so protective; I hope someday I’ll find someone like him.

I only heard from my now ex-boyfriend a few times in the next month. He dropped by to stuff my purse in the mailbox, but I never again wanted to see him face to face. I now know that it wasn’t my fault on that night, but my shattered self image took a long time to mend. My body did better. And luckily, I didn’t end up with a souvenir of that awful event (Meaning, I didn’t end up pregnant.)

I hope someday I’ll be able to love again.

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