When I was in my late 20s, I had a 22-year-old girlfriend, Gina, who soon after we met, started rooming with a much older woman, Grace, in her late 50s, maybe even 60 or beyond. It was just a coincidence that she was the mother of an old acquaintance of mine who'd long ago moved out of state, and I'd met her many years before, when he and I went to prep school together. Frankly, I barely remembered her, but she remembered me very well.
Being so far apart in age, it was strange that they would room together, but Grace was lonely and just wanted company, though she and Gina had practically nothing in common. It definitely was not a money thing, as the lady was four-times divorced from wealthy men, each of whom she had had taken to the cleaners. Gina's rent was dirt cheap for the fabulous park-view apartment furnished and accessorized with the finest.
Because I was living with my parents while I went to grad school and Gina had such a choice pad, I often hung out there, whether she was there or not. From old pictures in the apartment I could see that Grace had once been a real beauty, and was still attractive, despite her age, with a pretty face; very nice, big breasts; a decent ass, shapely legs; and just a little fat cushion around her mid-section.
Of course, with my girlfriend being a young card-carrying hottie with the best butt in the USA, firm, puffy-nippled B-cup tits always braless, a beautiful face; and long, curly blonde hair, I had no sexual interest in the older lady at all.
Yet, because I was over there so much, I got to know Grace very well, and she was always extremely interesting to talk with. It would be an understatement to say she had a substance abuse problem, as her medicine cabinet was a veritable pharmacy of psychoactive drugs, and she started drinking from her well-stocked bar at precisely noon every day—right after she got up.
By late afternoon, the vodka martinis, Valium, Percodans, and Demerols had her feeling no pain. Though wasted, she still could speak articulately and maintain a certain inebriated elegance.
I'd smoke my pot, drink her booze in the evening, and enjoy the conversation until late, when I'd leave to pick up Gina from the swanky downtown hotel where she was a cocktail waitress. We'd come back and fuck for a while in her bedroom, which adjoined a bathroom adjacent to the den where Grace would often be watching TV, then I'd leave for home.
That was the usual routine.
Though my girlfriend was extremely sexy looking with quite possibly the best ass in the history of womankind, her newness wore off pretty fast, as she was neither a tigress in bed nor a sparkling personality. Gina loved sex, though, and expected a good fuck from me every night after she got off work. And she would get quite testy if I didn't boink her soon after we got back to the apartment, especially if I lingered for a moment to chat with Grace. Gina was not quite a lousy lay, but she was not exactly a real good one, either.
But I stayed with her, as she professed to love me, was a stunning looker who liked frequent sex, and, of course, had that great apartment where I could hang out anytime I wanted.
In the ensuing months, Grace became ever bolder in terms of her clothes, or lack thereof. At first, I chalked it up to the drug and alcohol cocktails, but I gradually realized that she was purposely flashing due to her strong sexual interest in me—or perhaps anything with a functioning penis. I mean, you don't walk through the den topless and not realize it, no matter how stoned you are.
I must say, though, those tits were really nice ones, pendulous D-cuppers, swaying to and fro, with big pencil-eraser nipples. With my girlfriend's having small breasts, I did tend to gaze ever more at Grace's large hooters. Had their breasts been reversed, I would probably have been checking out Grace's smaller pair. As they say, the grass is always greener on the other side of the fence.
Grace would frequently find some reason to come into the bathroom between Gina's bedroom and the den and linger quietly in there while we fucked. I'm certain she was listening, pretty sure she peeked sometimes, and suspect she was masturbating. She must have also learned that Gina was not a sexual dynamo.
On very short notice, Gina took a weeklong trip to see her dad in San Antonio, though he had just visited her a few weeks before. With her old Beetle in a perpetual state of broken down, I assumed I'd take and pick her up at the airport, but she had made other transportation arrangements with a girlfriend. That was strange, as I routinely took her practically everywhere.
I did not hear from her all week, and when she returned, I dutifully proceeded with the obligatory fuck-within-10-minutes-of-opening-the-door routine, yet she was acting somewhat aloof—odd behavior for such a horny girl who hadn't had any in a week. Hmmm. Detail guy that I am, I noticed that her suitcase had Phoenix tags on it, one going and one coming back, rather than San Antonio, where her dad lived. Suspicious. While she was in the shower, I looked inside the case, and one whole side was packed with sexy lingerie—a choice of clothes inconsistent with a visit to see her dad. Upon closer inspection, some of the crotches had semen stains. Now, how do such stains get on a girl's underwear? Had Gina gone to the Sperm Store, bought a bottle of cum, and slathered some there just for fun? I don't think so!
Through a mutual friend, I knew that her old boyfriend was stationed as a pilot in the Air Force near, you guessed it, Phoenix. A little investigating on my part yielded the tasty information that he was about to be released from the service and was moving back to take a job as a commercial airline pilot based in his old home town--my and my girlfriend's--or should I say HIS girlfriend's town.
OK, so this girl who supposedly loved me had lied about where she really went, fucked her old boyfriend for a solid week, and he would be home soon with a good job to seal the deal. Obviously, I was about to be dumped. Gina was not The One, so I could have easily handled her breaking up with me, but this was downright shitty.
Though I was not in love with Gina, I had been really good to her: lent her money, bought her thoughtful gifts, took her nice places, got along with her psychotic mother, and drove her to and from work and anywhere else she needed to go.
And I had been faithful, too. I recalled the multiple occasions her cute girlfriend had come on to me. She, another girl, and Gina were rooming together when we first met, and once, right after Gina left, the gal let out a blood-curdling scream from the bathroom, like something was terribly wrong. Just as I ran in, she raked back the shower curtain, stood there smiling all wet and sudsy and nude, and said, "Jump in and let's have some good, clean fun!" Despite that I knew she was wild and kinky from a friend who'd dated her in high school, I turned her down. He said she swallowed cum and smiled; Gina spat and frowned.
And I could not forget the lost opportunity with the girls who lived across the street. There were three of them, all very tall babe-a-licious late teens, and they'd often be lying out catching rays in the front yard and hoot and holler at me when I'd come to visit Gina. "Nice legs! Ooooh, I like 'em long and tall. Aren't you tired of your little girlfriend?" I'd smelled pot wafting from their tanning circle before, so, out of rolling papers one day, I walked over there to borrow some. In less than five minutes, they ever-so-casually volunteered that they were bisexual, particularly horny that day, and very much wanted "a nice, hard cock" to join them for an on-the-spot FFFM. Day-um! But I graciously turned them down.
Here I' been the good and true boyfriend, and my girlfriend, who supposedly "loved" me, had lied and cheated on me. I was mad as hell!
Then I recalled the old adage, "Don' get mad, get even." Exactly. What could I do to really even the score? I envisioned several scenarios with her girlfriend, the girls across the street, and the waitress she worked with who Gina loathed because she was even better looking than she and flirted with me. These were all very good, doable options, but I concluded that the best way to get her goat would be to fuck Grace! And I would do it in such a way that Gina would "catch" us in the act!
So, the following afternoon, I took her to work, but told her just before I let her out that I had to go to bed early for an exam early the next morning and so had made arrangements for a friend to give her a ride home. Therefore, since there would be no post-work fuck that evening, there'd be a pre-work fuck instead. She kept nervously looking at her watch while I pulled my car around into the alley, pulled up her skirt, snatched her panties off, and screwed her extra-hard doggie style on the front bench seat.
It was almost 4 o'clock, bright and sunny, and about 65 degrees, so my windows were down. In a minute or two, an old, toothless drunk staggered up the alley, stuck his head through the driver-side window, and asked, "Got some loose change, partner?"
I don't know how I came up with such a pithy reply on the spur of the moment, but I said, "No, but I've got a loose partner I'd like to change." Neither he nor Gina got it, but he did get a free show of me pistoning her pussy centered in the rippling young flesh of the best looking ass on the planet! Gina protested that he was a creep, to stop, and tried to wriggle away, but I had my hands on her hips in a vice grip and kept on boring her like a drill press.
She quickly shut up when she realized her vocal objections were attracting the attention of co-workers in the distance coming in to work, but they were too far away to see what was going on. Of course, the drunk could see exactly what was going on and watched the whole thing while rubbing his crotch. I judged the man could use some assistance, so I handed him her panties. On cue, and with glee in his eyes, he whipped out of his filthy trousers a hard cock (a strange, dark organ with a 30-degree bend in the middle) and began whacking it vigorously with her soft peach panties while sporting a big, gummy, toothless smile.
I continued to mightily pound Gina's gash, and he was with me stroke for stroke. The notion of synchronized sex as an Olympic event briefly crossed my mind before I quickly refocused to savor her superb heart-shaped ass one last time before blasting a huge load of hot man juice into her fucked-plum-raw pussy. She came, too—it was always easy to tell because her back would arch, toes curl, and fair skin flush—and I just kept spurting and spurting and spurting. The old drunk came too, annoyingly right on my side view mirror, then slinked off behind a dumpster. I would have preferred he shot his wad into Gina's pretty eyes and lovely blonde curls, but, hey, you can't have everything!
