Chapter One - We meet Jessica, Michael and Sam (as told by Jessica)

It had been a hard day and while I usually didn’t leave my office before the close of the market, I decided to take a break and treat myself to a chai tea from the coffee shop. Standing in line before me was a cute thin guy. As I often do, I imaged what this hottie would look like with an extra hundred pounds of fat on his body. As it always does, this kind of daydreaming got me hot. When I saw that he had ordered a large fattening whip cream covered coffee drink and a scone, I got even more aroused.

As if he could sense what I was thinking, our eyes met and he spoke to me...”I guess I should have chosen something less fattening,” he said with a smile.

My knees got weak and the only thing I could think to say was, “Everybody needs to be naughty once in a while”.

I used the word “Naughty”? What was I thinking?

He asked me if I wanted to join him at a table and I said OK.

“My name is Michael,” he said.

“I’m Jessica.”

For the next half hour, we chatted while I watched him enjoy his scone and whipped cream-covered coffee. The whole time I kept imagining this guy about 200 pounds heavier. As I got up to leave, Michael surprised me and asked me out on a date. For some strange reason, I accepted and we exchanged phone numbers.

The market had closed by the time I got back to my office, so I had some time to just sit at my desk and think about what had just happened. I normally don’t do much dating because my career as an investment advisor requires so much of my time and energy. But there was something about this guy that I found appealing and the image I had created in my mind of him as a fat man got my heart pumping.

Just then my secretary, Sam came into my office and handed me a note about a client I needed to call. She noticed my distraction and asked me what was on my mind.

I told her about what had happened at the coffee shop.

“That’s awesome!” Sam said. “What does he look like?”

“He’s good looking but a little too thin for my tastes”, I replied.

She laughed and said, “Yeah, I remember that you like your men on the chubby side. Maybe you can get him to gain a few pounds for you.”

I blushed and said, “Maybe”

My first date with Michael went surprisingly well. He took me to Olive Garden for dinner, because he said that he loved their paste and the limitless bread sticks. He told me that even though he had a big lunch, he was starving. He kept saying things like that, not knowing the effect his words were having on me. Even though I have never had the courage to really let myself go, after he said he liked a woman who was not afraid to eat, I decided that at least that night, I would allow myself to eat as much as I wanted. So, we drink several glasses of wine while I intentionally stuffed myself with several kinds of pasta and lots of bread sticks. When it was time for dessert, even though I was so full I could hardly move, he insisted that we share a piece of tiramisu.

After we finally finished eating and were waiting for the check, I told him that if I kept eating like I did tonight, I would get very fat. To this he said, “That would be fine with me.” Again, he always seemed to know just what to say.

On the drive home, because we kept talking about how much food we had eaten, I was getting hotter by the minute. When we finally got to my apartment, I was so horny I could hardly stand it. As soon as he had parked the car, I was all over him – kissing his face, feeling his body, trying to unbutton his shirt. He asked if he could come inside and I almost shouted the word, “Yes”.

We hustled to my front door – him with most of the buttons of his shirt undone and his hairy chest exposed. As soon as we got inside, we once again started feverishly kissing and frantically trying to undress each other. When I finally got all those buttons undone and got his shirt off, I noticed that his belly had a bit of a bulge to it. He had trouble with the zipper on my skirt because my belly had expanded from eating so much. We desperately pulled the rest of our clothes off and threw them on the floor. We never made it to the bedroom. He pressed me against the wall, lifted me up and I wrapped my legs around me. I was wet, he was hard, and he entered me. I had the most incredible orgasm almost immediately and he came in me soon after.

When I returned to work Monday morning, I was still on cloud 9. Sam noticed it right away. I confessed to her that my date with Michael had gone very well. She told me to hold on a minute, that she’d be right back. When she returned, she was holding two plates with pieces of cake on them from an associate’s office birthday celebration. She placed one of the pieces in front of me, sat down, and pressed me for all the details of my date. I normally don’t eat anything in the morning, let alone cake, but something felt different in me. I started telling her everything she wanted to know while eating that fattening treat.

Later that morning, Sam insisted we go out for lunch together so she could hear more about my date. Normally, I stay in my office and skip lunch, but today, I agreed to go out with her.

Even though I usually have a small salad at my desk for lunch, I decided to indulge at the restaurant so I ordered a big meal and even treated myself to a glass of wine.

I saw Michael again a few days later and once again we went out to eat. At his insistence, I once again ordered a lot of food.

There was an obese couple sitting at the table next to us and all during our meal we would make innocent comments about them. At one point, Michael jokingly said to me that if we keeping eating like we are, we’ll look like them before we knew it. I could not help but imagine what it would be like to do that, letting ourselves go and watching how our bodies expanded everyday until we become as large as the two of them. Maybe it was all the wine talking, but I asked him if he would still find me attractive if I was a large as that woman. When he answered, “Absolutely,” I got extremely aroused. When it came time for dessert, instead of us sharing one serving we each got our own.

We left the restaurant and drove to my condo. This time we actually made to my bedroom. The sex once again was incredible! I noticed that Michael spent a lot of time feeling my swollen belly.

When I came into the office the morning after my second date with Michael, Sam came in almost immediately. She was holding two glazed donuts and set one down in front of me.

“What’s with the donut?” I asked.

Sam explained, “I figured that with all the calories you’ve been burning in the bedroom lately you could use the extra energy. So tell me all about your date last night.”

I knew I shouldn’t do it, but I took a big bite out of the donut and told her everything.

At about noon, Sam again comes into my office and tells me that she and some of our other female coworkers were going out for lunch. She then asked me if I wanted to come along. I said I better not. I’ve got a lot of work to do and besides, I’ve been eating way too much as it is.

“Ok,” Sam says. “I’ll bring you back something.”

I said, “No you don’t need to bother.”

“No bother,” she says as she turned and walked out the door to my office.

She returned about an hour later and plopped a bag of food down in front of me on my desk.

“Are you trying to fatten me up?” I asked.

She giggled and said, “Maybe,” before she turned and walked out.

After all the food last night and the donut this morning, I knew that I shouldn’t eat any of it. But it smelled so good that my mouth started to water. I have to admit that Wendy’s knows how to make a double cheese burger and their fries are the best. I have not had a Coke in a long time and I’d forgotten how good Coke is. I enjoyed every calorie of it.

I hadn’t been to the gym ever since I met Michael, but with all the eating and drinking I’d been doing I thought it best if I go to the gym after work. I changed into my workout clothes in the locker room. Was it my imagination or were my leggings a little tighter than normal. My sports bra seemed to be unusually tight, and the tank top I normally wore seemed to show off a little more cleavage than before.

I usually jogged three miles on the treadmill, but after only one mile, I was really sweating and so winded that I decided to stop. What the hell, I thought. How could I get so out of shape in just a few days?

I don’t know what got into me, but on the drive home I saw a KFC just up ahead. As if I was possessed, I pulled into the drive thru. I couldn’t even make it home, I just sat in my car and ate my “value meal” which included 3 pieces of greasy chicken, mashed potatoes and gravy, macaroni and cheese, and a coke.

A wicked smile came to my face as I thought about all the fattening food I had eaten lately, and my tight clothing at the gym.