Chapter 2: Jill Confides in Me

This summer I was teamed up with Jill, a 32 year-old housewife who had two kids, both in VBS, two boys ages five and six. Frankly I don’t know how much we actually “taught” this age group. It seemed more like we provided a week-long babysitting service than anything else. Jill’s boys were little terrors and I wasn’t sure if it helped or hurt more to have her in the same class with them. Sometimes I’ve found that kids actually behave a lot better when their parents are NOT around. Jill didn’t seem to have much control over her two brats and at times I could see the look of frustration and embarrassment in her face. It made me feel a bit sorry for her so I never said anything to her when one of her little monsters threw the class into chaos.

It was Wednesday, half way through VBS, and Jill and I were having a conversation as the kids worked on a project, coloring some picture or another. There were a couple of high school girls helping out so it didn’t leave much for us to do for the next half hour or so but to make sure nobody ran off or got hurt. For some reason she seemed a bit more frazzled than usual today and I notice her temper seemed even shorter than usual. It seemed as if there was something bothering her but she didn’t want to bring it up so finally I thought maybe I could help out a bit.

“Sorry, I don’t mean to be nosy ... something bothering you today Jill?” I asked gingerly, trying to sound supportive but not aggressive.

“Oh nothing,” she sighed, shaking her head. Uncertain how to respond, I just sat quietly to see if she would follow up with anything and eventually she sighed again.

Was t my imagination or was she perhaps trying to get me to ask her again, as if she wanted to tell me something but didn’t have the courage to just tell me. This time I reached out to touch her hand as I gently asked, “Are you sure? You can trust me with anything you know.”

While she din’t pull her hand away, I could feel her tense with my tough. It seemed like forever before she pursed her lips and let out a long breath.

“Just be glad you’re young and single Kelly,” she warned me, “Don’t rush out like I did and do something you might regret later.”

“I’m sorry?” I replied before thinking, “I don’t understand.”

Jill’s cheeks puffed out and eventually she let out a deep breath. “Just saying, you need to be careful. Not every guy out there cares what happens after he’s gotten what he wants.”

I couldn’t help but smile and replied, “Trust me, I have NO intention of getting tied down any time soon. I do like to enjoy myself but don’t worry, I take plenty of precautions.”

“Yeah, I hear you like to ‘enjoy’ yourself,” Jill retorted rather off-handedly and then apparently realizing what she’d said, she covered her mouth and then tried to apologize. “Oh God, I’m so sorry Kelly, I didn’t mean to say that.”

Of course she did or she wouldn’t have said it. Still, I knew what she meant and as I said, such comments have never bothered me much so long as they didn’t get out of hand. Actually I sort of enjoy hearing what people say about me, or the judgmental looks women, at least mostly women, give me.

It was like she was in other world though, her thoughts were clearly not on the kids we were supposed to be chaperoning. True the high school girls pretty much handled things but there were time we still were needed. Then it was like her whole demeanor changed as she sat up straight and looked me in the eyes. Jill glanced around as if to see if anyone was within earshot before asking in a low voice, “So tell me Kelly, how do I look?”

“Ummmmmm, what do you mean, Jill?” I quickly replied, not sure at all where this new line of questioning was going. Like wow, talk about a wide open question!

Jill took a great and bit her lower lip. She took another look around again before continuing, “You know, as a woman Kelly, how do you think I look?”

After a week of relative boring conversation, I was a little surprised at her question and still unsure how I should respond. Jill was only about ten years older than me and still looked pretty good if you asked me although she’d put on a few pounds having her kids which she never lost completely. She had long curly brown hair that she usually let just hang down her back without much adornment. While no beauty queen, Jill was pretty in her own way, much more so than many of the women at church. I imagined she was one of those “girls next door” guys get turned on by when in their teens. Typically Jill dressed sharp and carried herself with confidence. Perhaps the first thing anyone would notice about her though was her boobs which I was guessing to be maybe 40DD. Whatever size, they always seemed in the verge of bursting out of her bra. The pink tank top she was wearing today didn’t help matters as it was quite tight which showed off the outline of her bra and the curves of her breasts as it valiantly tried to contain her impressive boobs.

After her big boobs Jill’s main attraction in my opinion was her legs and like her boobs, she obviously knew it. Some women (not me!) are lucky to be born with the right DNA giving them proportionality longer legs. Well, Jill had that gene in spades. Long and nicely shaped, I could only imagine how they must have looked in her teen years. Even with her weight gain, they still looked great. She seemed to enjoy showing them off as I couldn’t ever remember her wearing pants - always a dress, skirt, or shorts like she was today. The white shorts she was wearing today showed off her legs without being TOO short such that they would draw attention as being inappropriate for church, but still shorter than most women her age, especially to a church event.

Some women gain weight and look like it with hanging upper arms, bulging stomachs, cellulite legs, etc. Not Jill, whose extra weight somehow made her look even sexier. No doubt her bra size was enhanced! Perhaps the tight tank was a little over the top as not only did it cling like Saran Wrap to her boobs, it also hugged her stomach a little more than it should have yet she didn’t have the rolls of fat many women gain in their 30’s. Maybe the shorts could have hidden a little more of her heavy thighs, but somehow it all seemed to work for her as they didn’t look fat so much as just “all the more to admire” as my dad used to say when he saw her in church. Yep, I would have definitely classified her as a MILF if I were a guy in church.

Not only did Jill draw the attention of my dad. Indeed, I noticed that more than a few of the husbands often took a second look when she walked by and even some of the younger teenagers seemed to enjoy sneaking a peak at her big boobs when she leaned over to help out with something. It didn’t hurt her tops typically were cut low to reveal a substantial amount of cleavage - not enough to actually show her nipples or anything like that, but still lots of top boob. Even as heavy as she was, the shorts did a nice job of showcasing her ass, much to the apparent enjoyment of the men and judging from some of the whispering I overheard, not entirely appreciated by the women, especially the married ones. Lucky for her it seems women these days with heavy booties are encouraged to show them off.