My New Mistress
It was spring and I had just broken up with my girlfriend of eleven months. It had been a pretty emotional break-up and the sex was something that i'd miss the most, and I didn't know what to exactly. As the days went by, I began to look at other women in a more sexual way. My ex-girlfriend never liked me talking with a lot of different women, and when we broke up she said that she didn't care who I was with. Initially we where supposed to take a break, but it eventually turned into a full fledged break up. What was the worst was that I still had feelings for her, but I know that they'd pass. Now at this time I was only fifthteen and it's not like I knew a lot about relationships. I've had my fair share of them, but this one was different. Anyway on the second week of the break-up, I found myself sitting on a brick wall outside my high-school. I was waiting for a ride to go home, and I was waiting until I got home to go jerk off. I was still feeling pretty depressed, but as more girls in short white skirts walked by I grew more and more happy. I liked to picture them nude, and begging for me to fuck them, but I knew that i'd probably not end up fucking any of them. Now at fifthteen I didn't think I was that attractive of a guy, but other girls have told me that I was. Not that I didn't believe them, I just didn't view myself as that attractive of a guy. And as I felt that warm spring air move against my white skin, I saw a girl who I used to have a crush on in front of me. She wore a black short skirt, and a tight white blouse. I used to picture fucking her around my house and hers, she had a great body. She was 14, and at that age I was guessing that she had a B cup. Her hair was light brown, and she had amazing eyes and lips. And as you went down, her body was skinny and petite. Her tits I'd imagine where perfect, and her ass was tight. I thought about how i'd want to fuck her, but I saved the thought for later. A backpack was strung over her left shoulder, and I got a look at her legs. I had always loved great legs, and hers went on for as long as for a mile. She was extremely attractive, but not the girl who i'd fall in love to fast with. We had a past of not getting a long before, and we've had a lot of fights in the past. She dumped me for a loser awhile back, and ever since we haven't been good friends. But as I saw her walk along the road, I couldn't resist to try and go talk with her. And as I went to get off the brick wall, I thought of what i'd say. We haven't talked in awhile so I didn't think a simple, "I want to fuck your brains out" would work in this case. I went to walk to talk to her, but I found myself to shy. My ex-girlfriend wouldn't exactly like me talking to her because she was my ex-girlfriend's best friend. So I went back to sit on the brick wall because I knew that a simple 'hello' wouldn't work in this case. My ride wasn't showing up, and it was late so I didn't know what to do. And as I sat back down on the brick wall, I got an erection. I knew that she'd be mine, but I didn't know when. When I got home, I felt depressed. I went upstairs in my house, and layed down on my bed. I thought about my ex-girlfriend and I remembered how we'd never had sex. She had never put out at all, I had to ask for it when I wanted to. The most we'd done is fingering, and otherwise i'd never gotten home with her. My ex-girlfriend was really attractive, she had long legs and a tight ass. She gave some of the best blowjobs that i've ever had, and at our height we where extremely attracted to each other. But that quieted down, and I found myself with no girlfriend and my dick in my hands. As I looked through various porn sites on the Linux computer that was in my room, my mind flashed back to the girl who i've seen earilier today. I pictured her being the girl I was fucking as I moved my right hand up and down on my dick faster. Within minutes I found myself close to orgasm, and I pictured her getting on her knees in front of me with her mouth open. As I clenched my eyes closed, I could feel my cum seeping out of my slit. It streaked down my head, and down to my hand. The last picture that i've thought of was her swallowing a day's worth of cum.
About five minutes later with my mind blazing from the intense orgasm that i've
just felt, I found myself on an instant messanging service. I saw her name online, and I thought about my pick-up line I could use on her, because I knew she wouldn't open up to me that easiely. I double-clicked her screenname and still thought about what I was going to say. My sweaty fingers typed 'hey' on my greasy keyboard. I waited about thirty seconds, and I figured she wasn't going to message me back and as soon as I pressed 'minimize' I heard a beeping noise. I clicked on her conversation, and I saw a hey with a smiley face next to it on the screen next to her screenname. I smiled, and typed in a reply, "How have you been going?". We countinued on this common conversation, until she asked me a sort of serious question. "How are you and Amanda doing?", she asked me after about fifthteen minutes of talking. My heart sank at the sight of what she asked me, I'd rather not think about her. "Uhh… Not so good", I felt like closing the conversation. The conversation switched to what's been happening with me and my ex, but then I told her that i'd rather not talk to her about it. She immediatly understood, and asked me a rather odd sort of question. "So how's your sex life since the break-up?", I smiled. "Absent", I got a "lol" as a response. Our conversation turned to our sexual encounters with various people, apparently the most she's done is been fingered by the loser that she dumped me for. I told her about my sexual encounters with my ex, and the first time i've been naked with her. By the time I looked at the computer clock again to see the time as 6:00 P.M. I looked across my room to see my Xbox not being used, and I told her that i'd be back later. My plan was coming in perfectly. When the clock struck Nine, I went back online. Sure enough, she was signed on. Almost immediatly I saw her IM window screen pop up in front of my eyes. Her simple greeting said, 'Hey'. I laughed because that's the greeting that every girl uses when they want to talk to me. Of course i'd bet that, that's a very normal greeting anyway so I wrote a 'hey' back. We went back into the conversation about sex that we had before, and by the time I looked at the clock again it said 1:00 a.m. We've been taking for about four hours or so now, and all about sex. She was turning me on, and I could tell that I was turning her on. So I worked up the courage and I asked her, 'You getting off to?'. There was a slight pause then she responded with, "Yeah". My cock instantly got hard, and I reached in my pants and pulled it out. I worked my hand up and down the shaft, cumming almost immediatly. I looked at the screen again after the buzz of the orgasm wore off, and I wipped the glob of cum on my tip. I felt tired and I decided to call it a night, "Goodnight Laura, I think i'm going to go lay down. Kind of tired". There was a slight pause, and the sign of her typing and a response came up, "Goodnight Steven, I'll go to sleep too". She ended her sentence with a little '