Noticing Mrs. Benning

When I first met Riley Benning in Middle school, she was a short, painfully skinny nerd, that wore huge, thick glasses. I was one of 3 kids in her mom's carpool to school. When I started having trouble in Algebra, her mom thought it would be a good idea if I came home with them, so that Riley and I could do our homework together.

Like Riley, her mom was short and wore thick glasses. But as skinny as Riley was, her mom was fat. Mrs. Benning was really nice, though. I don't know what she did for a living, but she liked to cram herself into these polyester business suits, with buttons just ready to pop, that made her look even fatter - like an over-stuffed sausage.

With Riley's help, my grades improved, so we kept it up, slowly building a relationship. Over the next year or so, we progressed into boyfriend/girlfriend territory, holding hands and stealing kisses.

But as soon as we hit High School everything changed. Riley ditched the glasses for contacts and decided she wanted to try out for the cheerleading squad. When she made the team, there just wasn't any more time for us: the carpool broke up, she wasn't available after school for homework-time, and she was spending all of her time with the other cheerleaders. Meanwhile, I decided to join the football team. So, we broke up, but remained friends.

By the time we were both enrolled in the local community college, she was different. In High School, she'd really bonded with her cheer squad, done a lot of partying. I never thought I'd see it, but Riley had been riding high in one of the most popular groups in school. She'd gone from mousy and shy, to energetic and playful. now in college, she still got good grades, but, except for her friend group, didn't care much for school. The classes she took were only to keep her mom quiet. She really only wanted to do whatever her friends were doing: shopping, hanging out, partying, etc.

Several times, I'd be on my way to her house to pick her up, only to get a text that she'd gone out already. The message was always the same: someone had invited her to go somewhere, so I should just meet her there. The first few times she did this, I was okay with it. But after a while, it started wearing me down. We weren't dating, but it still hurt.

One time, I got all the way to her house without a text. So, I figured maybe this time we'd be able to go out, just the two of us. My knock was answered by a short, shapely woman with a bandanna holding back her ponytailed blonde hair, grubby jeans and an old t-shirt rounding her out. This woman (a maid, maybe?) proceeded to tell me a group from school had dropped by earlier, in a shiny convertible, and Riley had gone with them.

Disappointed, I turned to go, knowing that Riley and I were through. "Oh. Don't go. I was just trying to clean out the hall closet and need someone tall," she said as she pulled me into the house. On the way to the hall closet, I had to step carefully, as my boner noticed the sway of her shapely backside. I managed to climb to the top of the stepstool without embarrassing myself, but that left me with a great view of the Grand Canyon, down the V-neck of shirt.

I honestly lost my balance, but was happily embarrassed when she caught me, because one of her hands ended up grabbing me by the front of my sweatpants. We both stood for a second, looking at each other with our mouths open in surprise. Her fist was wrapped around my boner, my boner straining against the fabric of my pants, pointed straight at her face. When she met my stuttering excuse with a coy smile, I just about freaked. She gestured for me to be quiet and proceeded to let my little guy fly.

After a surprised look, bordering on appreciation, her face lunged forward and my boner disappeared in a warm, wet world of gentle suction, making my mind spin. I'm not sure how I kept my balance, especially when I dumped 18 years of pent-up virginity down her throat (Riley and I had never gotten that far). She hung on and choked through it, not letting any of my discharge get escape.

"Wow!" she said. "I don't know what came over me. I hope you don't mind, but its been such a long time and... Well," she said in a low voice, leaning in conspiratorially, as I got down from the stool, "My ex-husband's dick isn't even as nice as yours! Don't tell Riley, okay?"

"Riley? We aren't seeing each other. Besides why would she care if the housecleaner blew one of her friends?"

"Cleaner?!! Riley's my daughter, Todd. I've known you since you and Riley were in my carpool. Remember?" Then she started laughing.

After quite a few interjections of "Oh, shit," while I gawked at her, it finally sank in what a hot babe Mrs. Benning had turned herself into, and I started laughing, too. I hadn't seen her since she was a goofy-looking pig, bursting at the seams. But now, she was slim and curvy, and had huge tits! She explained that, when her husband took off, she'd ditched her glasses for contacts and hired a personal trainer.

We hung out for the rest of the day and just talked. She was really easy to talk to and could talk on almost every subject. In fact, I confided I was having trouble with my grades, so she offered to help me saying, "Just homework, though. Right? I'm not offering anything like we did earlier." I remember turning red and agreeing innocently, assuring her I wasn't making any assumptions.

Over the next few days, I couldn't stop thinking about our time in that closet and fantasizing about putting my boner between those awesome boobies! So, I decided to just stay away. But my schoolwork really was in trouble. I needed help.

It cost me numerous cold showers, but Mrs. Benning was true to her word and helped me pass my classes. In fact, the fantasies and desires were just starting to subside, when the end of the semester came, and I knew I would no longer have to submit myself to such temptation.

When I let Mrs. Benning know I'd passed Calculus, the last math class I'd need, she decided we should celebrate and broke out the wine. By the end of my second glass, however, I noticed she'd gone through almost the entire bottle by herself. Sitting next to me on the couch, she confided that she really liked the time we spent together working and talking. As she said this, she snuggled up to me and rubbing my arm. Then she looked up at me, and I noticed tear in her eyes. She said she'd been so lonely since her husband left, and she barely saw Riley anymore. Our tutoring sessions were the only thing she had been looking forward to every week.

I'm not sure how things progressed form there. But somehow, we started kissing and ended up in a naked heap of sweaty clothes on the floor, panting from satisfied exhaustion. I'd only ever kissed Riley, and now the blowie from a few months ago turned into full-on sex with a woman old enough to be my mom!

I was shocked by the turn of events, but happy, as I'd never known how wonderful sex could be. It was difficult to describe, but maybe like being a part of another person, while being held in a warm, silken embrace.

We didn't talk much, as I gathered my things and left, neither of us knowing what to say, or even if we should say anything. In fact, a solid week went by before I decided to man-up and put an end to my childish desire to make something out of it that it wasn't.

So, I locked down my courage and dropped by her house when I knew Riley would be away. Answering my knock, I could see a look of pleasant surprise, when she saw me standing there. I stood up tall and laid it all out: I told her I knew I was NOT in love with her, but that really liked spending time with her, with or without the sex (although that part was awesome, too). Further, pointing out the loneliness she'd expressed, I proposed I continue to come over a few days a week, so that we could hang out.

When I was finished, she invited me in and said, "Wow, Todd. You really are growing up." Then, as I stood there waiting for the other shoe to drop, she broke out laughing, "But you can drop all this manly valor stuff," going on to explain that we were friends, and she wasn't in love with me either. She told me she'd been thinking about it, and really would like to keep up our visits. Then, raising an eyebrow and biting her fingernail, she said, "As for sex, well...."