This is part of a series of unrelated yet similarly themed fictional short stories entitled MATURE SECRETS. They can be read in any order. All characters are fictional, and all are over 18.
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Last summer, right after I turned 18 and I graduated from high school, I got a summer job stocking shelves at a grocery store, a big chain. They're open 24 hours a day, so, I got stuck working the night shift. There aren't many customers in the middle of the night, so there are only a few people working with me. Most nights that I work, the person checking out is a woman named Dee. I'd guess she's about 40, with short black hair, glasses; attractive if not spectacular. The store has a strict dress code, so every night Dee pretty much wears the same outfit: a white blouse buttoned all the way up in the front, black denim pants, and a silly little black tie. And we all wear long green aprons tied behind our necks.
There isn't much to think about on this job, and there aren't many hot babes shopping in the middle of the night, so whenever I'm working near the front, I like to sneak peaks of Dee. Even her apron couldn't hide the fact that she has real big tits under her white blouse and white bra. Also, her black jeans were always real tight, and I loved to stare at her ass. She didn't have a great ass, it was a little larger than ideal, but her pants were so tight that I just loved to look at her. The first couple of times she glanced over and caught me looking at her I was embarrassed, but she would just give me a little smile, and after a while I'd just smile back, and keep on looking.
When we weren't busy or if I were helping her bag groceries, we'd get the opportunity for a little small talk. I took a half-hour meal break at 2:30 AM, and Dee took her break at 3:00 AM. After a few weeks, Dee talked me into taking my break at the same time as hers, "to give me someone to talk to and keep me awake". When we were on break, the night manager covered for Dee on check out, and everyone else was out front, so Dee and I were always alone. Our break room was in back, up a flight of stairs. It was just a small room with one table, a few chairs, a refrigerator, a microwave, some lockers, and a bathroom. Every night we would walk up the stairs, take off our aprons, eat our sack meals, and then read or talk for a few minutes. I'm generally pretty quiet, but we both consumed a lot of coffee to keep awake all night, so we talked pretty freely. I was glad to have someone to talk to, but mostly I enjoyed the opportunity to see Dee up close without her apron. I continuously stole glances at her tits through her blouse and big bra. And her pants were so tight around her crotch. I would sit kitty-corner from Dee so I could look at her crotch in her tight pants. I could see her protruding mound, and the seam down the middle looked like it was being sucked right into her slit. At that angle, sometimes her blouse left a gap between the buttons, and I could look in and see some of her cleavage spilling out of her white lacy bra. She must have caught me looking at her, but I was too horny to stop, and she never seemed offended.
We really didn't have much to talk about. Dee would mention her husband and kids, and working nights kept my social life to a minimum. Dee once asked me if I had a girlfriend. I said "no", and she replied, "You should, you're an attractive boy". That made my night. Actually, I had a few dates in high school, and I guess I wasn't bad looking, but I was quiet and not real popular. I had felt up one girlfriend, but I was still a virgin.
Sitting kitty-corner, our knees would touch under the table, and we got into a little game where I would press my knee into hers every night, and she would silently press back. There was usually a newspaper on the table, and after a few nights we got into the habit of reading our horoscopes. Then I would slide around and sit right next to Dee, and we would read the paper together. The first time I did that I pressed my thigh against hers, and she immediately pressed back. We sat as close together as humanly possible, our legs rubbing together from our hips to our knees, never mentioning it.
One night Dee pressed her tit into my shoulder as we read. I wondered if Dee could see my hard cock in my tight pants. My hand was holding the newspaper, resting on the edge of the table. Dee leaned forward and pressed her tit into the back of my hand. I wanted to escalate the touching, but I didn't want to risk too much with this older married woman. Finally I put my hand under the table, on my own thigh, my little finger just barely touching Dee's thigh. When she didn't move or say anything, I slowly moved my hand over to her leg, about half-way up her thigh, over her tight pants.
Dee slowly moved her hand under the table, and put it firmly on my thigh. My heart was beating faster now, and I slowly moved my hand up her leg and gently squeezed the inside of her thigh. We both struggled to keep a casual conversation as Dee slid her hand up my thigh, resting an inch from my hard dick. I moved my hand up further, and Dee spread her legs to accommodate. I moved my hand up until my little pinky just barely grazed Dee's crotch. Then I felt her fingers graze my hard cock. I went for it all and cupped her crotch over her tight pants and gently rubbed it. Dee spread her legs more, and cupped my dick and squeezed it.
