Chapter 5 - getting the guts to ask

Mary had stopped at the servers station to put in their order, but when she was done, she ran into the kitchen and started to cry. I immediately took her into my office. I tried not to stare at how her fat little gut jiggled as she sobbed. That was a horrible thing to enjoy! But damn did it look hot..

"Glen I got fat, didn't I? I know I put on a couple pounds but is it really that bad? Am I really a lard ass?"

Hmm.. it would have seemed insincere to tell her she was still thin and looked fine. It was obvious that wasn't the case.

"Mary, those guys are just drunk college kids. They will make fun of anyone! You can't let that upset you. Look at all the tips in your belt. You are obviously still a very sexy girl!"

I felt okay about that. She WAS still sexy, sexier than ever actually. And her face may have been sporting an extra chin now, but it was still beautiful.

She nodded and wiped the tears off her bloated cheeks. Like a champ she got up and went straight back to work. But I got concerned.. what if she decided to lose weight now that she had been humiliated? I needed her to continue being a glutton and keep all those luscious pounds on so I could ask her out and be able to get hard when we had sex.

I had been wanting to ask her to hang out for a while at this point. She was finally fat enough for my liking and I was nearly obsessed with watching her work. I had to find creative ways to hide my hard on when she would stop and bend over to get something. So many wonderful bouncy curves! I even liked the new way she started walking, with a little sashay that made her ass rock back and forth behind her. She was such a perfect plumper now, i couldn't take my eyes off of her.

I finally got up the nerve to ask her the next day. Not to be sadistic, but asking a fat girl out right after she got teased is usually a good move. Their confidence is gone and they will say 'yes' just bc you are a man that wants them. I asked her to come over for a nightcap before I took her home. As expected, she obliged easily.