This story is part of a series of separate stories that are related. They are not specifically chapters or parts of a larger story. Each story stands on its own. These stories are accounts of a single event as experienced by three different people. If you like any one of these stories, look for the other two. The stories are; Amanda's, Blake's and David's view of this one event and what led each one to participate.
Blake's Story
My name is Blake and I am 33 years old. This is the story of how sex with an older woman made me the luckiest man in the world.
I've always been lucky at love. Well, lucky at dating anyway. My friends all tell me it's because I won the genetic lottery and have the look that women want. I am not so sure how true that is. Even if it is true, it's not the blessing that my friends make it out to be.
I started out saying that I was lucky at love, but that isn't really the case. I've dated a lot and have been in some longer relationships, but my relationships have always ended badly. It was like I was dating the same superficially perfect blond every time, they just had different names and faces. Come to think of it they didn't really have faces that were all that different. I was in a rut dating the same kind of girl over and over.
A little over a year ago I was in a relationship one of these blond clones named Rachael. She was tall and pretty with a perfect body. Rachael spent a lot of time and money on her looks and it showed. She was always perfectly manicured and wore designer clothes that made her look really sexy.
As we dated more and more of the money she spent on her looks came out of my wallet. I didn't really mind. She had the cutest way asking me for things, and I knew that buying her something would get me laid. And I got laid by Rachael a lot. Eventually I realized that Rachael didn't actually love me. She just loved what I could buy her.
I wondered how Rachael would react if I wasn't providing her with all the things she liked so much. So one day I refused to buy her this overpriced dress she wanted and she got pissed. We argued about it, and later that week she broke up with me. My friends all told me I really needed to quit dating these needy blonds.
After Rachael and I broke up, I decided to swear off of relationships for a while and I told all of my buddies to hit me with a stick if I got anywhere near another Rachael. My single friends were happy because that meant I was free on weekends to go out and party.
One Friday a couple of my buddies and I decided to eat at this new restaurant before we went out to party. When I got there the place was packed so I moved to the bar to wait for my friends. I figured when they got there we could go somewhere else less crowded to eat.
While I was waiting for my friends this older woman started chatting me up. She had this suburban mom look to her, and like I said she was older. She was probably around forty. She was kind of chubby with dark hair and glasses. Even though she was older, she had a nice smile and a cute face.
Every time she said something she would lightly take hold of my arm like she didn't want me to get away. Since she was wearing a wedding ring it seemed safe to play along and flirt back with her. This wasn't going to lead to anything. It just seemed like a fun way for both of us to pass the time. When her table got called she scribbled her name and number on a napkin and told me to call her. Then she walked away wiggling her ass and shoulders like little girl that had just gotten away with something.
I was thinking, 'Wow, did that really just happen? Did a married woman just give me her number?' Shortly after she left, my friends arrived and I told them about the chubby MILF. They accused me of making it up so I looked on the bar for the napkin, but it was gone. The bartender must have cleaned it away with the woman's dirty wine glass. My friends and I bolted from the place, skipped dinner and went on to the clubs.
The next Monday I was going through my pants so I could put them in the laundry and I found the dammed napkin. I thought, 'See I told you fuckers', as I tried to make out the name she had written through the damage from being in my pocket. It looked like her name was Amanda, and even though there was damaged to her number I could still make it out. Amanda was cute, but she wasn't really my type. She was also very married. I have no idea what possessed me to do this, but I decided to call her and see if she wanted to fuck.
Later that day I had a break in my work so I called Amanda. She seemed surprised but happy that I called. Back in the noisy bar I hadn't noticed anything special about her voice, but on the phone her voice was really sexy. It was the kind of voice that makes your cock tickle a little when she talks.
Amanda's voice made talking to her like phone sex, but without the dirty talk. We talked for maybe an hour that day, but didn't even come close to hooking up. I really liked her voice so I called her again the next day. Then I kept calling every day that week, mostly just to hear that voice. Finally on Friday we started talking about sex. It was about damn time.
As we talked I was surprised at how someone with so much sex in her voice could be so sexually conservative. There was so much she either had never tried or just wouldn't do. She said that she didn't even masturbate. (Her words) At that point I was thinking that she didn't even like sex, and I wondered why she had given me her number.
But then she surprised me. She asked if I ever thought about her while I played with myself. (Again, her words) I lied and told her that I never jacked off. She refused to believe me. Then she told me some story about how she caught her husband jerking off to porn and how she found some video of her husband fucking another woman.
As she told me about the video her voice changed dramatically. It sounded like she might start crying. I don't like hearing a woman cry so I tried to lighten things up with a joke. I told her that she just needed to fuck me a bunch of times and make her husband watch. Apparently she didn't see the humor in my comment. There was a long silence then she hung up on me. It felt so awkward so I didn't call her back.
Okay so I'm actually quite a bit more caring than I let on, and I was feeling pretty bad about what I had said to Amanda. So the next week I called her to apologize. I wasn't trying to get in her pants anymore. I just felt I needed to make things right with her. I started telling her how sorry I was for crossing the line about the video and having sex, and she stopped me.
Amanda then explained how she was using the threat of a divorce to force her husband to watch her have sex with someone. Then she started talking about how that someone was going to be me. It was a very strange feeling. She never actually asked me if I was willing to do it. She just assumed that I would.
Of course I wanted to fuck her, but not with her husband watching. I'm still not sure how this happened, but ultimately my desire to fuck her won out over the weirdness of being watched by someone. I had set out to talk her into having sex, and it turned out that she talked me into it. We made plans to meet at a hotel that coming weekend.
We had a couple more short calls that week and then on Saturday I got a text from Amanda with the hotel room number. Actually until I got that text, I had expected her to back out. Right after Amanda's text I got a call from Rachael. She wanted to see me that night to talk about getting back together. I also knew that this would end up with the two of us fucking.
I really wanted to fuck Rachael again, but I didn't want to have to put up with her relationship crap to get some from her. I probably shouldn't have done this. Instead of just telling Rachael I didn't want to see her, I told her all about how I was going to some hotel that night to fuck the shit out of this really hot MILF. I'm not sure when Rachael actually hung up on me, but I'm pretty sure she didn't listen to the whole thing.
Saturday evening I went to the hotel and waited in the lobby as planned. I was still thinking Amanda probably wasn't going to show up. Then I thought maybe she would show up without her husband. In fact I was of hoping she would be there alone because I'd never fucked in front of anyone before.
Around 6:30 I saw Amanda walk in. She was all made up and wasn't wearing her glasses. She looked really sexy. Then I noticed a man that must be her husband trailing behind her carrying her purse and her overnight bag. He looked like whipped puppy.
They walked right past me and Amanda winked and smiled the sexiest smile on their way by. Without glasses her eyes were stunningly pretty and I wondered why she ever chose to wear glasses. A few minutes later I got a text telling me she was in the room. I took a deep breath and checked the time on my phone. I was supposed to give her 30 minutes to get things ready, and then come up.
Those 30 minutes just crept by. I must have watched a hundred people walk by, and several were in their early forties like Amanda. Now that I had a reason to notice them, they seemed to be everywhere. As each MILF walked by, I wondered what it would be like to fuck them. Okay, so my mind goes a little bit crazy when I am horny. So what? I'm a guy! Finally it was time to go, so I went up and knocked on the door hoping like hell that I had the right room.