I worked with Matt in the copy room. We were 6 in the team, but Matt and I were always hanging out, finding ways to do jobs together and talking about sports.
I drove to work, 30 minutes each way, and it couldn’t be much more, because I had to get back to my dog in time to walk him. So when they instituted a new carpool policy on the highway to work, I was devastated. If I had to wait in traffic for hours, I would have to either move or quit my job or even have my dog put down.
I couldn’t believe my luck when I discovered that Matt actually 5 minutes closer to work on the same route. I couldn’t believe we’d never discussed that. I would pick him up on the way to work and we would take the carpool lane and save a lot of time.
One other thing Matt never mentioned, was his hot wife, Ruby
Usually I would arrive a few minutes early and wait for Matt in the house while he would get some coffee ready for us to-go. That was just enough for me to strike up an awkward conversation with his wife.
“So you’re going to work out this morning, huh?” I said. “Obviously” Ruby said, already wearing the workout clothes and having her gym bag. Yes, it was obvious, but I was just trying to make conversation.
Over time the conversations would be less awkward and I would try to remember what we talked about last time and follow up on that. It helped. She also got more comfortable with me in her home and wore casual clothes.
“So Ruby, cleaning the house today?” I asked. She didn’t snap at me that time. “Yeah” she giggled “Not much else to do here anyway. And we were on a first name basis.
A few weeks later when I picked up Matt, he said he had to take care of something first. “Sorry, it’s gonna be a few minutes, I’ll be right there”.
I knew all about his few minutes. I would likely be waiting for 20 minutes or more. I struck up a conversation with his wife while she was working out.
“Did you think of anything for Matts birthday?” I asked her. “No!” she said. “Do you have any ideas?”
“Actually, I do have one idea” I said. It was something I had been thinking about. I wasn’t planning on suggesting it, but now that she asked, I thought, why not.
“I am a hobby photographer and I could take some glamour pictures of you that you could give him for his birthday”
“Really? Hmm …” She was clearly thinking about it, but didn’t say anything.
Matt came back “Sorry, just had to send an email. Let’s go!”
The next day when I came to pick up Matt, Ruby met me at the door. “OK, I haven’t thought of anything better. Let’s do those pictures you suggested. But no nudity, just some nice glamour shots.”
“Sure” I said “It will just be $200 for rentals”.
“Oh …”. Ruby was surprised I would charge her for that. I could see that she was not gonna pay up. I still wanted to do the session and I said “OK sure, I can do it for free for you, I want to be a professional photographer and I guess this will get me on the right track to that.” She smiled, satisifed.
“OK, it has to be a surprise” I told her “So tomorrow I call in sick and instead you meet me on this address”. I quickly wrote an address on the back of my business card and gave her and she put it in her back pocket.
The next day I called in sick as planned and went to the studio. I had already prepared different types of clothing and was ready for her when she arrived.
“OK, here are the sets, everything is ready for you”. I directed her behind a screen where clothes were waiting for her and she changed. “Are you sure you got the size right?” she asked when she came out.
“Yeah, it’s not for everyday use, but it’s covering the nipples and great for the photoshoot”. I took a few pictures.
She posed in different positions as per my direction. After a minute she had a bit of a wardrobe malfunction.
“Hey, OK, wait” she said “Don’t take pictures while I am fixing it. I don’t know if I want my husband to get those.”
“No problem” I re-assured her “You choose the pictures and then I package those for you in print and on a DVD”. She nodded “Ahh, OK”…
It was time to change into the next outfit and when she came out she had pretty much the same reaction as before. “I don’t think this is my size” she said.
She was even casually covering her bottom, feeling a little uncomfortable. “Sure, it’s small” I said “It makes things interesting. That’s why the pictures will be so good” I explained and reminded me that she could choose which pictures to send to her husband. She nodded.
When she turned towards me, I saw that she was absolutely right. This was not her size. I had seriously no idea that it was that small, but I figured there was no point making her feel insecure about it and I contained my gasp and just continued.
I had to turn around for me.
“Ohh, it’s not so small actually, it fits you quite well. I thought it was small too for a moment there, but really it’s just like any other thong, more or less. You are quite well covered.”
She knew what I meant and nodded. She knew a thong gave the impression of almost no clothing while in reality it was just a play of shadows and lines.
I got some more photos of her from the front and almost couldn’t concentrate.
This was really the money-shot. Worth the entire day.
We were about done with the day. Ruby looked through the photos and filtered a lot of them away. She was quite happy in the end, but was clearly wanting more conservative photos that the ones we ended up with.
“Whoa, some of those photos!” she said “I am sure glad that my husband won’t see them”.
“Don’t worry” I said “He probably won’t”.
“Thanks” she said as an almost automatic reply, before she heard properly what I said. “What do you mean by probably?”
“Oh, these photos were for my career, right? That’s why you didn’t pay for them” I reminded her “So I am putting them on my website portfolio. Thanks for helping out” I said.
“What!? No, OK – I’ll pay you!” she said. “No thanks” I said, “A deal is a deal”.
“But … is there anything …” she didn’t finish the sentence but I liked what I was hearing.
“OK, tell you what, I’ll call in sick tomorrow as well and come to your house after Matt has left, we will figure something out”.
She didn’t ask more about it, I guess she didn’t want to know.
The next day when I arrived, I saw Matt drive away and I went into the house, using the spare key. When I came in, I found Ruby just having showered, wearing just a towel.
“Oh wait” she said “Let me just get dressed”
“No need” I laughed “We have a deal to make, right? Just let that towel drop”.
She hesitated for a second, then dropped it. She was pretty much mentally prepared for this.
I went up to her and fondled her breast. It was a little awkward, I must say.
“Getting a good feel?” she asked.
“OK, we should get started, just lie back” I said.
“Seriously?” she couldn’t believe it. I got undressed again.
“Yup, that’s the deal, I fuck you and I don’t publish the photos to anyone”. She made a sound with her mouth indicating I was a jerk and lied back. I was sooooo ready and pushed my cock into her pussy.
I fucked her deep and long. “Don’t cum in me” she said, between thrusts “I am not on the pill or anything, we’re actually trying right now”
“Let me give you a hand with that” I said as I came in here. “Who knows, maybe you get lucky.”
She made that “jerk” sound again and left for the bathroom. When she came back I was dressed and heading out. “OK, see you next time” I said.
“What next time? This is it!”
“That’s up to you, that’s the deal” I said
“The deal” she said and was flustered “Was that I have sex with you and then you don’t publish the pictures”
“Right” I said “And as long as you fulfil your part of the bargain, I fulfil mine.”