1. The Time Jean Needed Her Ceiling Painted


    Date: 8/17/2015, Categories: Mature Author: devlincyde 

    I was fresh out of high school, working over the summer before college at a department store. I befriended a middle-aged woman named Jean who had a vivacious personality that gave off a young energy for a woman who openly admitted to being in her 50s. Jean had no reason to apologize, she had such an infectious energy. Everyone loved her. I adored her. As the summer went on, I grew to absolutely love her. Jean took a liking to me, too. I was 18, tall and lean with messy brown hair. She would joke to girls who I may have been talking to that &#034he's all mine, you can't have him!&#034 Everyone on the store staff found it adorable. &#034She's old enough to be your grandmother!&#034 one girl said. &#034It's so cute.&#034 Secretly, there was nothing cute about it. Jean may have been in her 50s, but there was something about her body that caught my eye from the very beginning. She was just built the right way, if you ask me: shapely with wonderful skin. She had light blonde/gray hair that fell around her face and shoulders with bangs over her perpetually happy eyes. She was always well dressed; conservatively but still a hint of suggestion. Button-up blouses with halters underneath. Flowing skirts. Her nails were always done. Her makeup always right. Oh and those tits. Big, round momma tits. They weren't obvious, but they were impossible to not notice if you were a breast man like me. She caught on quickly that I was, indeed, a breast man. &#034You don't have x-ray vision, do ...
    ... ya?&#034 she once whispered to me. &#034Why do you ask?&#034 I laughed. &#034Because you're staring at my girls as if you're trying to see through this blouse!&#034 she grinned. I turned red. She then touched my hand. &#034Honey, it's flattering. Don't even worry.&#034 From that moment on, it became a daily joke. She'd give me a wink, adjust herself or pull back her shoulders. I'd smile and give them a once-over and nod with approval. Once in a while she'd come by with a bra from the ladies lingerie section and hold it up. &#034Think this'll fit?&#034 I'd shake my head. &#034Oh no, way too small.&#034 The flirting intensified into August. I was leaving Labor Day weekend and knew our time was coming to an end. I wanted to spend time with her, I wanted her to know how often I masterbated thinking about her amazing breasts, but I just didn't know how to approach her. I wasn't sure if this was just an innocent playful thing or if she really was into me. Then one day in the break room, she asked if anyone knew of a painter. I offered my services. She grinned. When we were alone, she said, &#034Do you want to come to my house and paint my bedroom ceiling?&#034 I nodded, &#034I can do that.&#034 We picked a day we both had the night shift and I went to her house around 9 a.m. I showed up in painting pants and brought a ladder and brushes. When I came to the door she saw me and laughed. &#034What?&#034 &#034So you really came to paint!&#034 she replied. Uh...yeah? She was dressed in a ...
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