14 years ago I posted a couple of stories from my first sexual experience, which…
Anal debut
I had been pretty curious about anal sex here lately. After all, I watched enough of it on porn. For some reason, watching the girls in the movies, moan and wince in pain, made it seem all the more naughty! Shan kept teasing me about how he was just going to slip it in my ass one night, and that he wasn’t going to tell me when. Just thinking about not knowing when I he was going to try it on me made me nervous. I kept wondering will it hurt? All of my girlfriends seemed to like it and so I kept thinking it’s got to something worth trying.
One night while I was staying over at Shan’s house, he cuddled up next to me in the bed. He wrapped his arm around me and rolled me over onto my stomach. Before I was really able to figure out what was going on, I felt his hard dick pressing up again my ass. Immediately, my pussy was wet with excitement. I started grinding my ass against his hardon, and slightly let out a moan or two. He told me, “Tonight, your going to get it like sluts deserve to get it.” Normally, I wouldn’t stand this kind of talk, but it was turning me on even more. I played along and said, “what did I do wrong Daddy?” This seemed to trigger his imagination even more, because he continued to role play with me. He told me, to take off my clothes. I did. Then I laid back down on the bed. He reached over and put his hand on the back of my head and stuffed his big cock inside of my mouth. I thought I was going to gag, but I just tried to take as much of it as I could. He kept telling me to, ” suck it you whore, you dirty little fucking whore.” My pussy was throbbing with wetness, I needed to be touched there so badly. With one hand I reached down between my legs and started fingering myself to relief myself of the aching. He grabbed my hand and told me, “did I say that you could touch yourself?” I said, No sir, but I need to be fucked. He pulled his cock from my mouth and tapped it against my face and said, ” well then, you’d better get on your hands and knees.” Not expecting, what was about to happened, he positioned himself behind me, and rubbed the head of his dick over my pussy entrance, and dipped it inside once. then he pulled back out. Then he stuck one finger in my asshole. I moved in shock, because I wasn’t expecting it. He then removed his finger and stuck the tip of his dick at the entrance to my virgin ass. He then slowly entered my ass… as I swirmed in pain, and begged him to go slower. He then with no warning, shoved it all the way in. And all at once I felt the pleasure mixed with the pain. I wanted it, but I didn’t want it. It hurt but it felt so good. He leaned over to my ear and whispered, now daddy’s little girl is going to get fucked because she’s a fucking little slutwhore.” He then pounded me and pounded me as I screamed and moaned. My ass was hurting from how much pressure it was receiving. Then he told me I’m going to cum in your ass. I was so excited by the thought of having my ass filled with his hot cum, that I cummed before he unloaded his into me. He pulled out after he was finished, and he slapped my ass. When he did that, I started to feel the cum dripping from my asshole. he looked at me, and said “well you little whore, clean it up!”