When I was 13, my girlfriend's mother was simply huge. This worked out well for me, as I have been attracted to bigger women as far back as I can remember. That's right; I hate to say it, but the only reason I was dating this girl--or as close to "dating" as any 13-year-old can really get--was to give me an excuse to be around her much larger mother.
Like I said, my girlfriend's mother--let's call her Eve--was a large woman. She only stood about 5'6, but weighed a good 450 pounds at least. She had a tremendous set of hooters--though I had no idea of her cup size, or even what a cup size was at that age--along with a bulging double-belly and a simply enormous ass. Her ass was nearly as wide as I was tall! By contrast, I was a skinny child, all knees and elbows back then, the only thing that really stood out about me was my perverse desire to be crushed by this fat older woman.
I got my wish that summer. Through a once-in-a-lifetime series of coincidences, my girlfriend was out of town the same week as my parents, and rather than hire a sitter my parents just let me stay at my girlfriend's house, with Eve watching me. (It wouldn't be until I had a learner's permit that my parents would permit me to spend a week by myself.) She was a large woman who loved to throw her weight around; I would later discover she was heavily into the local BDSM community. At the time, though, all I knew was that she liked horsing around and, if she was heading your way, you'd better move unless you wanted to wind up under her feet. She also had a habit of not watching where she was walking; if, say, a horny young boy was in her way, it was his own damn fault.
I took advantage of this habit at first by hiding in doorways or around a corner and sticking a hand in the way of her feet. Eve would stomp on my feet and move on without missing a single beat. It hurt, yes, but it was so heavenly! The exquisite pain I'd feel when her full weight came down on my outstretched fingers, or occasionally my entire hand, was enough to send me into a horny teenaged bliss for hours to come. I would get hard just from hearing her tread coming down the halls. But eventually I got bolder, began to crave more.
One night, after Eve came home and fixed herself dinner, she told me to pick out my favorite video to watch. I left the kitchen to set up the VCR--I hope I'm not dating myself too much by saying that--and take a spot on the carpet near the sofa. As Even strode into the TV room, I thought it was odd that she was still wearing her heels from work, but that fit my plans perfectly. After she turned off the lights and sat down, I inched my way over to a position by her feet, thinking I was being ever so subtle. When Eve shifted her position to make herself more comfortable, I wormed my way under her heels and braced myself for impact.
If I had thought Eve's bare feet on my hands could hurt, I was totally unprepared for her heel-clad feet on my back and ass. The extra pressure was pure, erotic pain! If her heels had been any sharper, I'm sure I would have been bleeding! She kneaded me with her feet for a few minutes--I was worried that she'd think there was something wrong with the "lumpy carpet," fool that I was--before truly settling in and pressing down with even more weight. I was in pain, but that pain was heaven. I don't know how long I lay there, wallowing in my role as human foot rest, before Eve spoke.
"So you like that, do you, Mike?" she said, snapping me out of my reverie.
I think I said something to the effect of, "I ... uh ... but ...?"
"It's okay, sweetie," Eve said, digging one of her heels into my butt. "In fact, I'm flattered. There's something else I could do to you, if you're interested."
"Yes, ma'am!" I said, ecstatic at her proposal, whatever it was. I gasped a little as she started nudging at the waistband of my shorts with her heel. I wasn't wearing a belt, so she was able to work my shorts and underwear down my legs fairly quickly--even moreso when I realized what she was doing and helped her out. Her heel returned to my ass, working its way right into the center of my crack.
"This is going to hurt at first," she said, "and it's going to hurt a lot, but I think you'll like it."
Before I could ask what "it" was, she pressed her heel harder, harder, harder against my asshole, and before long at all was able to work it inside my virgin ass. She was fucking my ass with her shoe! She was right; it did hurt--like taking the worst shit of my life, in reverse--but as she kept working her heel in and out, in and out, in and out, I fell into a rhythm and began enjoying it. Soon she was forcing the entire length of her stiletto heel into my ass, only to pull it out and thrust it back in again. I moaned with pleasure as she continued to fuck me with her foot, and after 15 minutes I came long, hard, strong, and LOUD. I'm pretty sure I blacked out, too, if only for a moment.
We forgot about the movie soon after that. After I regained my strength, Eve fucked my ass with her other shoe, making me cum almost as hard. She then had me finish stripping and get in her spot on the couch. She took off her skirt and panties and sat on me with the full weight of her gorgeous, naked ass. She kept me on the verge of blacking out from lack of air for the better part of an hour, and came multiple times herself. I slept in her bed that night, and every other night that week. I spent my nights either held tight in her flabby arms, underneath her slumbering bulk, or baring my ass to her and her strap-on. It was a week of pure paradise.
Even after my girlfriend and I broke up, Eve and I continued to see each other every now and then until I started high school. Not as often as either of us would like, but we both knew that, as taboo as our relationship was, we should be grateful for any time we had together.
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