Where it happened: At a 5-star hotel
Langauge: English
Sex: Male
Rating: 8
Category: Straight
Well, my first time was with a girl named Rachel. I was 18 and she was 17. We were on our high school’s senior trip. Our class had gone to Washington, D.C. (we’re from N.C.). Rachel is really athletic, far more than me. I’m no wuss, but she’s an avid marital arts student, and can overpower me pretty much anytime she wants. We had been going out for about three months at the time. Sadly, I was still a virgin at the time. We had gotten all dressed up earlier in the day to go to a ceremony at the National Cemetary, but I was really uncomfortable in those clothes, so I took them off as soon as I got back to my hotel room. Most of our friends had gone of to explore the city, but I stayed back, just to have a little time to myself, or so I thought. I was in my room, naked, laying on the bed watching TV. Someone knocked on the door. “Who is it,” I called. It was Rachel. “I’m naked,” I called through the door, not thinking she would actually come in. Much to my surprise, she answered “Good,” and I heard her slip the key-card through the lock. (I’d given her my extra key earlier). Shocked, I sat up and grabbed a pillow to cover myself. In she came, dressed in a short, crimson dress with white, satin gloves, and wearing high heels. She closed the door behind her. “Ah, hi,” I said. Not very smooth, was I? She just looked at me for a moment, then, rushed at me. I was, to say the least, completely unprepared. Things were happening so fast I didn’t really understand what was happening. She back-handed me across the face, stunning me. The next thing I know, i’m on my stomach being hog tied! “What the hell!?” I shouted. “Shhhh,’ she said. I twisted my head to see her slip her shoulders out of her dress, allowing it to slid to the floor. she was wearing a thong, but no bra. I was quiet as she slipped off the thong. I had seen her toppless before, but I’d never seen her pussie. She’d shaven her pubic hair completely away, leaving her lips fully exposed. They were swollen a dark red, and already dripping with her juices. Her tits were swelled, and the same dark red. Even though I was laying on it, my penis instantly began to harden. “Shhhh,” she said again. I opened my mouth to protest, but as I did, she shoved her wet thong into my mouth and gagged me with it! She began spanking me, and believe me, she could hit HARD. “You’ve been a very, very bad boy,” she kept saying, over and over again. I tried to yell, to tell her she was hurting me, but i couldn’t get a word around her underwear. In minutes, my buttocks were aching constantly, and the pain was worsening with every blow. Smack! Smack! She hit me again and again. My eyes were watering, I could hardly breath. Finally, she paused. “Do you want me to stop?” she asked sweetly. I nodded vigerously. She bent down, her breasts daggling in front of my face. “Ok,” she whispered. At last, i thought, it was over. How wrong I was. She reached down, picked up one of her shoes, and inserted the three-inch heel into my anus. I had never taken anything up the ass before, and it hurt like nothing i’d ever felt before…and yet, at the same time, I had never felt such intense pleasure before. She gently wiggled the show about. My whole body below the waist hurt. My ass cheeks stung, my ‘hole felt like it was on fire, and my penis ached intensly. I realized I was actually getting off on the torture! Rachel realized it at about the same time. She pulled the shoe out, and rolled me over. Freed of my body weight, my penis sprang up. I was hugely embarroused. My penis is only about 5″ long, and I felt extremely inferior. She took one of her satin gloves, wrapped it around my sex and began to massage it. I had never felt such ecstacy! I had also never before been so erect in my life. I felt myself about to cum. I tried to resist, but I just couldn’t help it. I blow a load right into her face! My seaman ran down my outstretched cock, and around her hand. I had masturbated before, oh yeah, many times, but never had it felt like this! I finally stopped, and I felt myself begin to soften when Rachel said, “Oh, no. you don’t think we’re done, do you?” I groaned. She bent over and took me in her mouth and began working my head. To my surpise, I felt myself harden again. At this point, Rachel stood up, straddled me, and lowered herself onto me! I slipped into her tight, wet pussie, and I can not describe what it felt like. She began to hump me, harder and harder. Tied as I was, it hurt my shoulders, knees, etc, terribly, but it felt so GOOD! After several minutes, she doubled over in a monstrous, messy orgasim. I came again almost immediatly after, and so hard that my stomach muscles cramped up. She got a moist washcloth and slowly massaged my aching balls. Then, at last ,she untied and ungagged me. She reached down, frenched me for almost a minute, then bent to pick up her clothes. I said nothing as she quickly dressed. Just before she left, she turned to me and said, “again, tomarrow?” I just nodded.
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