The Tooth

I've had a toothache for a couple days now and it's really pissing me off. I finally got a dentist appointment made for next week, but I'm on my own until then. So I thought mayyyyyyybe jerking off would take my mind off it...

Nope.

Well it felt good of course but it didn't help my tooth. The wife wasn't much last night. She kind of hinted / intimated that sex might get my mind off it. Then we get upstairs and she said "Thinking about me being inside her while thinking about my tooth hurting weirds me out." So what would you say to that? I said, "OK, well I'll kiss you goodnight and go to the other bed then." And I did.

Well, I went into the other room anyway. I had taken some Advil PM medication to help me sleep since I was only able to get 2 hours the night before. I decided with the time I had left before I inevitably drifted off to sleep that I would stroke. Of course. What else did you think I'd do? You know how much I love to masturbate.

At that point I'm in the bed in the other room in my boxer briefs. I reach down and start rubbing my cock and I think back to a particular time in college..

*INITIATE WAYNE'S WORLD DREAM SEQUENCE START UP*

I had gone over to Michelle's house. I liked to go over and hang out with her family. They were all very nice to me. I found out later after we broke up that her little brother (maybe 7 or 8 at the time) really liked me and kept asking when I was coming back over. See????? I'm really a great guy! So we were in her room which was in their converted garage. We were sitting on her bed playing Crash Bandicoot (great game). The TV was at the foot of her bed on a shelf. Our traditional places for this was that I would sit across her bed with my back against the wall and she would kind of sit on my lap facing the TV. So her right side was against my chest. Her brother would sit on the floor between the bed and the TV. We always took turns playing. Her brother would play either a level or until he died, then he'd had Michelle the controller and she'd play, then my turn and then back to him. It was always a lot of fun. Believe me, it took longer to lay this out for you than to think it. So I didn't spend all this time thinking about the memory while I was getting hard LOL.

One of my favorite things to do was try to distract her while she was playing. She had rather large breasts for such a small person and I looooooooooooved them. I know all guys like boobs and I like them even more than that. As she was playing I liked to slide my hand up between her and the controller and tease the underside of her boob. Nomally she could handle that so I'd have to slide my fingers up to her nipple. Now I'm not always the most coordinated person and doing all that while trying to look like I'm watching the TV isn't as easy as it sounds lol. Once I found her nipple and rubbed it a little bit I almost always got her to die. Saying that makes me sound like a bad person! Don't worry, she returned the teasing though. Somehow I usually managed to live a bit longer while her smaller hand tickled, rubbed, and rolled my balls in my shorts. We'd get so worked up we'd have to stop so we could calm down while her brother was there LOL.

This particular time though Michelle's friend Crystal was over as well. I had met Crystal before and we had actually had a double-date with Michelle and I, and Crystal and my roommate Matt. They didn't hit it off as well as we thought they would.... Anyway.... Michelle and I were sitting a bit further down so Crystal could play too. I didn't get to play with her boobs but she moved a bit so I could rub and squeeze her ass. She let me know how much she liked it by kissing me any chance she got and licking my earlobe. God, that thought gives me shivers even now. I don't know what ancient chinese secret she knew but she had this way of licking and sucking my ears that could bring my unit back to attention no matter how many times I'd cum.

We played for a couple of hours and then it was time for her brother to head to bed. We said goodnight and Crystal got on Michelle's PC. Michelle and I "played" for another 15 minutes or so. That 15 minutes basically consisted of me teasing her seisitive nipples mercilessly while she rubbed the outline of my growing cock. Crystal was right there so I couldn't drop her on the bed and fuck her like she deserved. Michelle looked at me. Her eyes said she wanted something more and I wasn't going to disappoint her. We laid down with our feet down by Crystal (the PC was at the side of the foot of the bed). Michelle got on top of me and we started making out. I know that doesn't sound like a big deal. I've talked about more "adventurous" things. I don't know if it was because we were already so worked up or if it was because Crystal was sitting right there, but I'm pretty sure it was both.

Soon her legs slid to either side of mine and her pussy was rubbing my cock. I know, I know, both of us naked and me inside her might have seemed like it would be more fun, but it wouldn't have been nearly as erotic. She had on some small silky-feeling shorts and I was in basketball-style shorts. The feeling was amazing. I kept my hands at the sides of her breasts, squeezing them softly as she ground her pussy against me. She leaned her head down and asked if Crystal was watching. I pushed up against her as I looked through her hair and then told her that I could see her peeking even though she wasn't outright watching. That got Michelle a little wetter I think. It might have been my imagination but I thought I could almost feel how wet she was against me. I was so turned on I could barely think. Suddenly Michelle stopped grinding and just pushed down hard against me and kissed me passionately. I remember thinking, "holy fuck she's having an orgasm!" That was a big deal for me since we hadn't really done much that night( comparatively) and I was still pretty young. She only made a small sound though. She was trying to hard to be quiet. After she finished and her lips left mine I pulled her down and whispered I wasn't going to last much longer if we kept this up. She grinned and whispered back that she'd take care of that. Now I figured she'd just keep going and I'd finish in my shorts. I was very, very wrong. I thought because her friend was there she'd just keep going and I'd finish in my shorts. I was very, very wrong again. She scooted back down the bed quickly on her knees, putting her body almost level with Crystal as she sat at the computer. Michelle looked up at me as she pulled my shorts and underwear down over my cock and pushed her mouth down over my tip. No hands. She just moved her head and I disappeared. Well, most of me anyway. I didn't care if Crystal saw at that point. I lasted about a minute before I blew into Michelle's mouth. I usually cum more than the "average" I've been able to find online, but this was bigger than that. Having Crystal there had me unleashing apparently untapped stores of semen the size of baseballs LOL. It seemed like it anway. I remember feeling her swallow 3 times before I stopped shooting. She kept sucking me, never taking me out of her mouth, for another few minutes before releasing me and tucking my dick away again. I just laid there breathless as she came up and cuddled into me.

It was very quiet then. I don't think anyone knew what to say really. We looked at eachother again; a longer, more meaningful look, and I told her I should probably go home. She smiled and we decided to see eachother the next day (details of when and where). I said goodbye to Crystal and she said it too and I left.

*INITIATE WAYNE'S WORLD DREAM SEQUENCE END*

OK so maybe that wasn't exactly what I thought, but you wouldn't understand what I thought unless I described it like that. I concentrated on the feeling of passion and delight as I laid in that room running my fingers up and down my shaft. I felt my balls tighten and I jumped up, running to the attached bathroom so I could cum without having to clean up. I stood at the sink with my cock dangling over the edge into the sink and exploded. I pushed my shaft against the countertop/sink as I came, pumping it out of me. Quite a bit. I cleaned up a bit and washed it down and then fell asleep as my head hit the pillow. What do you think?

Fuck my tooth's hurting again. Damn oragel...