Author's note: The concept behind this story is relatively straightforward, but my hope is to give it more depth than it normally receives. It aligns more with my usual style of slow burn with strong payoff. I am still planning on returning to my Fiancé Seduced by Roommate series... there's a lot more left to tell in that. But I wanted to hammer out this story first while the iron was hot.
And the usual disclaimers: all characters are fictional, similarities to real-world people/events are purely coincidental, everyone involved is of legal consenting age, etc.
Sleeping with your friend's mom. It's a classic setup... some would say played out. Especially in porn, where it's often a 'teenager' (mid-twenties male talent) playing opposite a 'mature MILF' (early thirties woman who obviously never carried a child) doing their best to pretend they have years of sexual tension built between them. Some videos do it justice... but most don't. Now, I get it—people generally don't watch porn for the realism—but take it from me, realistic friend's-mom-hookups can be some of the hottest sex there is.
And I'd know. I lived it.
Mrs. Carson was the friend's mom in question for me. I'd been friends with her son Drew since we were in elementary school, and growing up, I spent much of my time over at his house, hanging out and sleeping over. I didn't have the best home life—more on that later—and staying with Drew was more than a fun time... it was an escape. For their part, Drew's family didn't seem to mind the amount of time I spent at their house; they warmly welcomed me every time I visited. There were four of them: Drew, Drew's sister (who's not relevant to this story), and Drew's parents. Drew's dad (Mr. Carson) was on the older side and generally distant from me, but he was friendly enough. Drew's mom, on the other hand...
Mrs. Carson was an attractive woman. I knew it from the first time I met her, even though I was too young to understand what attraction was. She was easy to look at and be around, unlike the gross and stuffy lady teachers at school. As I grew older, I began to realize it wasn't just Mrs. Carson's relative youth or demeanor that drew me to her... there was something more. Eventually I learned the word to capture this elusive description: Mrs. Carson was sexy.
She was on the taller side, around 5' 8", with long black hair that cascaded down to her lower back. Her face had started to show her years, but Mrs. Carson's large brown eyes and lightly freckled face were alluring nonetheless. Plus, the more time I spent around Mrs. Carson, the more I grew to view her face's maturity as a positive feature, rather than a negative one.
But Mrs. Carson's body was unquestionably her best feature. Her curves were perfectly proportioned, with sizeable breasts and a full ass, often on full display in her choice of semi-tight t-shirts and jeans. She nailed the balance between casualness and sexiness, a look no doubt perfected over decades. To be sure, Mrs. Carson had some extra padding after giving birth to two kids, but she'd distributed it well.
But there was something else that drew me to Mrs. Carson. It took me a while to identify, and even once I did, I still didn't quite understand why I found it attractive. Even now, I'm still not sure.
Mrs. Carson had a sexy walk. Yes, I know that's not usually the first thing that comes to mind when someone pictures sexiness, but there's no other way to describe it. It wasn't a model-walk or a stripper-walk. In fact, it wasn't deliberately provocative in any way. But whenever Mrs. Carson moved through a room, it always caught my eye.
My best guess is that Mrs. Carson's walk was sexy because it highlighted her flexibility and fitness. She moved quickly but effortlessly; full strides that emphasized her toned legs and ass. If you saw Mrs. Carson from a distance, based on her gait alone, you'd assume she was in her twenties. But by the time I turned eighteen, Mrs. Carson was forty.
Growing up around a MILF like Mrs. Carson was a double-edged sword. The upsides were obvious—she was terrific eye candy, and once I discovered masturbation, she was a regular guest in my fantasies. But there were downsides too. Drew wasn't oblivious to my attraction, and until I learned to better control my infatuation, it was a source of friction between us. Once I made a poor-taste comment to Drew about his mom, and he did not take it well. Our disagreement escalated and Drew kicked me out of his house. We made up after, but I was careful not to repeat that mistake again.
Still, even hidden, my crush on Mrs. Carson never went away. But there were cycles to it: She'd be at the top of my highlight reel for days or weeks, but then I'd find another woman (or girl my age) to fixate on instead. Sooner or later, though, Mrs. Carson would catch my attention again and I'd be head-over-heels once more. This cycle repeated year after year as I grew up around her. I moved from awkward middle schooler to confident high schooler... and finally, a senior and legal adult.
Once I turned eighteen, my fantasies about Mrs. Carson developed a new depth. Even though they were still fantasies, they were now plausible. After all, (legally-speaking) I was no longer a child, so Mrs. Carson and I could finally hook up. In my head, years of fantasizing had convinced me that if I caught Mrs. Carson at the right time and I said the right things, then I'd be able to seduce her. And I had a year left of high school—plenty of time to make my move before college.
I needed to be careful though. I didn't want to risk my friendship with Drew again. He was still my best friend, and even a fling with Mrs. Carson would lose its luster if Drew never spoke to me after. The trick was to spend time with her away from Drew. But how to do that?
One factor that worked in my favor was that Mrs. Carson was a stay-at-home mom. I didn't fully understand what Mr. Carson did, but I knew it involved business real estate and that it made him a fair amount of money. Enough money to support a single-income family-of-four, at least.
And so, as my final year of high school started, I made a strong push to have as many run ins with Mrs. Carson as possible. It wasn't easy; despite visiting his house frequently, Drew and I spent less time there than we had in the past. Now that we were both driving age, it was more common to meet up at his place just long enough to carpool somewhere else. I almost never saw Mrs. Carson during these excursions.
Fortunately, we didn't abandon Drew's house completely. If there was a movie to watch, video games to play, or sports to follow, we'd hang at his house like old times. I could see more of Mrs. Carson on these days, but even then, I didn't feel like I made much progress. I had several 'accidental' run-ins with her, but these encounters were inevitably disappointing.
I tried a few approaches. At first, I turned on the charm, complimenting her looks or choice of clothes: "You're looking awfully pretty this morning, Mrs. Carson", "that shirt looks great on you", and so on. Mrs. Carson seemed surprised by my forwardness, but she adapted quickly, taking future comments in quiet stride. She'd thank me for the compliments... and return to whatever she'd been doing before. I couldn't tell if her indifference to me was real or feigned, and so I adjusted my tactics.
I kept up my compliments but began striking up small conversations with her too. I'd ask about her day, how she was doing, etc. Mrs. Carson opened up a bit more, but never answered much beyond the specific questions I'd asked. I thought about trying to push further—maybe I just wasn't being forward enough—but I wasn't sure how. I'd been supremely confident in my charm offensive; that fact that it failed left me stymied. Clearly, seducing Mrs. Carson wasn't going to be as easy as I'd thought.
I still may have succeeded on my own, but as it turned out, I didn't have to.
Because that's when Mrs. Hartsell came into the picture and changed everything.
As I'd later learn, Mrs. Hartsell was Mrs. Carson's best friend during their college years. They'd stayed close over the following decades, despite living in different states. By coincidence, Mrs. Hartsell dropped by for a visit the same weekend I was hanging out with Drew.
I'd arrived at the Carsons on Saturday, unaware of the extra guest. As Drew let me inside and led me to his room, I heard two women's voices talking animatedly from somewhere inside the house. I shot Drew a glance, who merely shrugged back.
"Mom's friend. She's visiting from out of town. Just for the weekend though, don't worry."
I didn't press further, but as we walked through the house, we came across the two of them lounging in their living room. My eyes immediately went to the newcomer, and I'll admit it—as soon as I laid eyes on Mrs. Hartsell, I was smitten.
She wasn't quite on Mrs. Carson's level, but she was certainly attractive in her own right. She had shoulder-length brown hair, brown eyes, and tan skin. Mrs. Hartsell was thinner than Mrs. Carson, with less-impressive curves, but she was well-shaped nonetheless. If she'd ever had kids, she certainly didn't show it. I could tell she was Mrs. Carson's age, but she didn't seem stiff in the slightest. Even at this first meeting, I sensed a wild side to Mrs. Hartsell; her steady gaze and sly smile hinting she was always ready for a good time.
When Drew and I entered the room, the two women stopped their conversation and looked at us.
