Knowledge is Power Ch. 3byRidinghoodswolf©
I looked through Andy’s program and chose my first…well, victim.
She was about thirty, kind of shy and a little mousy, judging by her picture. She worked as a secretary in a government office. I had access to her emails from home, as well as a list of every link she visited and when. I used this information to study her habits. As she was my first, I ended up over studying her, as I was to find out later that you didn’t need quite so much information to pull this off.
I found out from her emails what time she went to work, so I showed up at her building and simply sat on the stairs in grubby clothes and an old hat, watching everyone who entered. I recognized her right away from the picture stored in Andy’s database. I had been right about my first assessment of her being kind of mousy. She was dressed in a tan shirt and a brown skirt. Her clothes were too loose to show her figure. She wore her hair up. When she walked by other people on the sidewalk, she looked down, even looking down when people greeted her who obviously knew her. She was just the type of woman who went to work every day, went grocery shopping, went to the movies, and no one noticed her. I shook my head with wonder thinking about the kind of sexual interests I knew this shy unassuming woman had.
I went home and reviewed her file in Andy’s database. I had figured out that the database tracked women based on their emails. All you had to do is enter an email, and the program began automatically tracking all emails and sites visited by the person’s web browser. It flagged anything sexual, but the complete list was available with a click of the mouse.
This woman was mainly interested in two things. She loved to read erotic stories about force, not rough force, but guys who took over and ignored protests. She seemed to like the idea of being swept away by a man’s passion. Recently she had been interested in something else. She had begun to read a lot of stories about anal sex.
She read everything about anal she could find. She looked for FAQs about anal sex and anal masturbation, she looked for erotic stories about anal sex, especially first time stories, and she had visited pages that sold anal toys, though she had not purchased any. From her emails to girlfriends I was able to determine that her last relationship had ended about a year and a half before. She had not had a date since. She had written to her girlfriend that he wasn’t adventurous enough sexually. Her girlfriend had recommended to her to suggest more adventurous things, but she had replied that, “She just couldn’t do that, and besides that’s the man’s job. It wouldn’t be the same if I had to do it.”
I knew from her file that she sometimes donated a little money to the local animal shelter, so I dropped by the shelter and picked up some flyers for an upcoming fundraiser. This time I dressed nicely and stood outside her building at about the time she came to work and passed out the flyers. I turned away when I saw her approaching, and began handing out flyers in the other direction. My tactic worked, because she came up to me and asked me for a brochure. We struck up a conversation, and I asked her if she wanted to get a drink after work. I suggested a place I knew she liked that was in walking distance to her apartment. She blushed – she was very shy – but she couldn’t hide her pleasure at being asked out. I knew it was her first date for over a year.
We met that night at the little bar, and I was my full charming self. I had to draw her out, but like most women once I got her talking she began to enjoy herself and come out. It’s amazing how much people like you if you can just get them talking about themselves. When I sensed she was really enjoying herself, I looked at my watch and suggested it was time to go. She looked taken aback, but picked up her purse and put on her jacket.
“May I offer you a ride home?” I said.
“No, that’s okay, I just live a block away.”
“In that case, I’ll walk you home,” I said.
When we reached her apartment building she turned to me and stuck out her hand.
“It’s been great meeting you, thanks, I had a great time,” she said.
I reached past her hand, grabbed her waist, and pulled her to me. I held her tight against me and looked down into her eyes. I stared at her right up to the moment of discomfort, and then I kissed her. I felt her lips open up, and when they did, I kissed her more deeply and passionately. I pulled back and looked at her. Her eyes were blinking.
“I want to come inside,” I said.
“I, um, I don’t know if that’s such a good idea,” she said.
“Do you have a couch?”
“Do you have a couch?” I repeated.
“I want to sit on your couch for a little while and kiss you some more.”
She paused for a minute.
“Okay,” she said, her voice a whisper.
We went inside, and I put my plan into action. As soon as we were in the door I kissed her again, more passionately than before. She responded, so soft and willing. I broke the kiss.
“Listen,” I said. “I am incredibly turned on right now. You are too hot to resist. You are one of those women who are shy on the outside but so hot and sexy inside. I saw that in you this morning when I first laid eyes on you. I have a lot of intuition, and I can sense things about you. I have to have you.”
Before she could respond, I kissed her again, this time harder, a little rougher. Before she could think, I turned her around and pushed her over the padded arm of the sofa.
“What are you doing?” she asked, in a trembling voice.
“Something you want. And truthfully…” I said, with a little laugh, “It doesn’t matter that much if you want it or not. You’ve made me crazy tonight, and I want you.”
I pushed up her brown skirt and pulled down her hose and panties. She gasped.
“Wait, wait,” she protested, in the pleading way of someone who knows what is coming is inevitable.
I pulled the bottle of lubricant out of my front pocket. It was warm from my body. I poured a generous amount in my hand and rubbed it up and down her crack.
“Oh my God, oh my God,” she said, more to herself than to me.
“I’m going to teach you about anal sex,” I said. “I had a sense about you. I can tell the kind of women who want anal sex.”
Yeah, sure. When I have a database that tracks their sexual interests, I thought.
“Listen to me. My job is to get you prepared to enjoy this. Your job is to relax and do what I tell you. I’m going to put my fingers in you first. Each time I penetrate you, I want you to push like you’re trying to go. This will make it easier.”
I immediately pushed my index finger inside her. She gasped and began to breathe heavily.
“You’ve put your finger up there before, haven’t you?” I said.
I didn’t know this for sure, but I was pretty sure.
“Haven’t you? Don’t lie, I can tell you have.”
She didn’t say anything. So I leaned over and looked in her face. She turned away. I grabbed her hair and gently but firmly pulled her face where I could see it. She was blushing so furiously that her face was glowing red.
“You’re a little ass-slut, aren’t you?”
She didn’t answer and I continued my maneuvers. I pushed my finger in and out of her until it was easy. I kept adding lube, pushing it inside her. I pushed in a second finger and she relaxed quickly this time. I added a third. At the third finger, she made her first sound of any pain, but that quickly relaxed, too.
“You’ve stuck things up your ass before, haven’t you? You little slut, I knew it.”
I poured more lube in my hand, and rubbed it on my cock, which was so hard it almost hurt. I placed the head at the entrance. She was loose enough from the three fingers; I knew it was going to work quickly. I pushed the head in, and she gasped, putting her hand back on my thigh to slow me. I pushed on. When I was fully inside her, I began to slowly move a little in, and a little out. She was well lubed at this point, so I was soon able to increase my speed and length of stroke. Soon I was fully fucking her, grabbing her hips and slamming in to her. She wasn’t a loud moaner or a screamer, but I could tell from the noises she did make that she was extremely aroused. Suddenly, she came, and she did scream a little. I laughed.
“That was your first time getting fucked in the ass, wasn’t it?”
“Yes,” she said, through heavy breaths.
“And you came without me even touching your pussy. Well, now it’s my turn. You’re going to do my favorite. Lie down on your back on the floor.”
She quickly complied, and I thought, Wow, she is taking domination and anal sex like no one I’ve ever seen.
When she was down on the floor, I straddled her face, facing her legs. My hairy crack was right in her face. I began to stroke myself.
At first, I was just slowly stroking, and then I felt her kiss my ass cheeks on either side of my crack. She was sucking and kissing, and I knew she was trying to get her courage up.
“Go ahead,” I said. “You want to and I want you to.”
I felt her tentatively kiss inside the crack, coming closer to where we both wanted her to be. I lowered myself a little more, and she found the spot with her tongue.
“That’s it, baby. That’s what I want. Lick Daddy’s ass.”
As she gained enthusiasm and confidence, I began to stroke my dick in earnest. With her warm wet tongue working my asshole, and my hand pounding my cock, I was soon close to coming. I let out a groan, as I came, and she did just the right thing, working her tongue up inside me as far as it would go as I was coming. Thick white ropes of semen covered her lower belly and her brown skirt. I stood up.
“Here’s my number,” I said, dropping my card on the coffee table. “Call me if you want to get together again.
I pulled my pants back on, and left.