How Did I Become a Sugar Momma
That was the question Dolly asked herself as she willingly and gloriously—and orgasmically—became the sugar step-momma to her new husband's son. Okay, she'd not exactly sworn off other men as her relationship with Ben progressed from Dolly-date to fuck buddy, to travel companion, to lover, and now to husband. Ben was generous, both financially and sexually, and he was successful enough in multiple aspects of life that he wasn't jealous about the fact that Dolly was just too much of a sexual goddess for any one man, and, therefore, she needed to have boyfriends on the side. Ben had been one of those boyfriends, though he wasn't exactly on the side of anyone. Dolly was not married, nor engaged, nor verbally committed to anyone when she and Ben met during Super Bowl week in Miami. After drinks, hanging out, dinner the next night, and then sex in Ben's South Beach suite, Ben told Dolly that he adored her, hoped to see her again (and again), and, since he was somewhat older than she was and she was pretty much a "sexual dynamo,” he didn't expect faithfulness. "I can't satisfy all of you, and you deserve as much satisfaction as life can provide you. I only ask you to be with me when we are together and to be considerate when you need to be with some other person blessed to be a special friend to you."
Which was about as awesome an offer as a woman with an insatiable sex drive and a body that could drive men from age 12 to 112 crazy could ask for. Basically, "Be discrete and give me priority when I'm in the same town." Ben was witty and considerate, treated Dolly with respect, and admired her brain enough to have multiple-hour phone conversations with her when he was in another city. Since a conversation like that wasn't going to result in sex, the only motivation, Dolly realized, was that Ben sincerely loved Dolly and that included just plain talking with her, hearing her outlook on things, and finding out how her day was. After maybe a year or so, many Dolly dates with Ben, and discrete dates with other lucky gents, Dolly and Ben got married.
Maybe in the rush of it all, she should have paid more attention to Ben's family. None of them lived locally in South Florida. Hell, Ben didn't really live in South Florida, but he traveled there enough that, once he met Dolly, he purchased a place and became a part-time resident. And a full-time romantic friend. And during the part of Dolly's time that Ben wasn't worshiping her athletically toned and sexy body in person as her lover, Ben understood Dolly was going to make sure she wasn't lonely. So the whirlwind of meeting his family, introducing him to hers, and the glamorous travel, dates, and the purchase, redecoration, and moving into their new marital abode with a view and direct beach access, plus Dolly's civilian life and professional chores, kept her from realizing, "Ben's son Greg is a fucking sexy guy!"
Greg—never married, frequent traveler, and entrepreneur; devoted son to Ben and uncle to his sister's children; and, like Dolly, a running and fitness enthusiast. They discovered they had actually been in a couple of the same half-marathons, though they had not known each other. And Ben was just a handful of years younger than Dolly, who was spotting Ben nearly two decades. When Greg's mother passed away after an aggressive illness, he went to boarding school. Ben saw him often, and had a great relationship with him, but Ben admitted, "I was ill equipped to be a full-time doting single dad." Ben was better off at an institution used to being the day-to-day responsible party in place of the kid’s parents.
Greg—handsome, poised, and charming like his father—had done well at boarding school. And he took a liking to MILF-aged ladies, losing his virginity to his roommate's mother during parents’ weekend, and learning a decent selection of methods to sexually please a lady from that same roommate's mother over several more campus visits. Before Greg scared himself by getting to be such a slut that he literally had to grab his pants and dive out of a bedroom window when his honors English teacher's husband arrived home unexpectedly, Greg earned a few MILF notches. The three-way with the girls' track coach, a former NCAA miler, and her same-sex occasional lover, was a particular highlight. "Are you sure you can handle two lusty ladies, Greg, with just one cock, fabulous as it may be," Coach Betsy asked him after she'd let him in the back porch of her off-campus cottage. "Bets," he replied, "you've cum from my cock, hands, and mouth. That should keep the two of you happy, and you two have promised me you are going to please each other as well, so ... let's do it." Greg was a well-trained lover of physically fit women. And Dolly was right in his wheelhouse.
Ben was delayed getting to Miami for Valentine's Day after being in Boston on business. He never should have planned to fucking fly into or out of the Northeast that early in the year, Ben admitted over the phone when Logan Airport was closed for the night. "Why don't you and Greg grab some stone crab claws? At least, you can have a handsome guy to drink with on our first Valentine's Day as man and wife. I'll be there tomorrow."
It’s not as if she hadn't had a couple of Dolly dates during Ben's few weeks up North. So, thinking it was just drinks and getting to know Ben's son a little better, Dolly told Ben she loved him and that she'd see him the next day. She then sent Greg a text, explained Ben was stuck in Boston, and could she buy her step-son a drink unless he had other Valentine's Day plans, since she hated to see her reservation go to waste.
Greg had no definite plans, other than visiting a favorite South Beach club, knowing there would be a few ladies there he'd established booty-call relationships with. So, when Dolly, whom he'd been envisioning during morning shower jack sessions, called and invited him to dinner, he didn't hesitate.
Stone crabs and liquor, followed by liquor and stone crabs, and a cab and dancing and shots. And as they stepped off the dance floor, Dolly draped herself on her young step-son to catch her breath. Greg was taller than his father, about 6’3”, and lean and muscular, about 180 pounds, and had a terrific 30-or-so-year-old body. Dolly realized she was buzzed just enough not to know exactly how old Greg, her sexy date on this hot, humid evening was. "We're both 30-something,” she told herself. Neglecting the three-carat diamond engagement ring on her left hand and the platinum set row of diamonds in the matching wedding band, Dolly was feeling no pain, exhilarated from the dancing and excitement, with Ben was pretty far from her mind. She never would have gone out randomly and hooked up in public like this now that she had married Ben. But the evening began with Greg, so her starting mindset was that everything was safe and okay and approved. But her shaved pussy, well toned by kegels and more kegels, wasn't feeling motherly. Or step-motherly. And she was just tipsy enough to tell the cocktail waitress that, she and her “sexy son-in-law" did indeed want another round. Greg was aroused and under the influence as well, but just clear-headed enough to know he wasn't her son-in-law. Her body was tight, fit, toned. It was like having the fitness instructor from the club draped on him, with every guy's eyes on her ass, legs, bare midriff, bust ... oh hell, the mid-back blonde hair, blue eyes, smile, and red "I want to dig these into you while you fuck me hard" nails were eye-catching, too. A few kisses from Greg to the top of her head while they stood close in the crowded club led to Dolly appreciatively raking his back, through his sweat drenched shirt, with those nails. Damn her legs were toned, how would those feel squeezing the cum out of him and into her? He started to tell himself he wasn't supposed to think that way, then thought, "Why not" and forgot about Dad.
A Miami Heat score was announced, and a big cheer went up. Dolly, being a sports fan, raised her arms and shouted in victory. Then she and Greg embraced. And then they kissed, pausing slightly before their lips met, looking into each other's eyes, as if to visually check, "Are we going to cross the line?" and then dragging each other way past the line. There was no hesitation by their tongues with regard to exploring each other's mouth. The tight embrace, his fully erect sex missile pressing against her, and Dolly not having been fucked in a week and feeling Greg's arms around her, his fingers on her lightly perspiring flesh ....
Neither spoke a word. Greg paid the tab, they got into a cab, and Dolly straddled Greg as they dry humped, or at least as dry as two sweaty bodies and one pre-moistened pussy could get, the several blocks to the high-rise Dolly shared with Greg's dad. Their eyes were filled with fire as they took the elevator upstairs. And Greg was humping her fit hard ass as he stood immediately behind her while she opened the door.
"Dolly," he started to say, breaking the deep, lustful kiss they shared while pulling each other's clothes off. But Dolly had other plans. "Just fuck me Greg. I need you tonight. We both want this," and then, as she undid his pants and felt the hot skin of his thick, ready cock in her hands. She continued, "And I need THIS." It wasn't anything intentional; it was just sexual instinct that led Dolly to pull Greg toward her usual bed so that he could fuck her.
Perhaps it was the feeling of family, familiarity, or perhaps the booze and the lust. Regardless, as Dolly pulled Greg's ass tighter toward her body, as their arms and legs entwined, as he thrust, kissed, touched, and generally fucked his step-mother's MILF sex-goddess gym-bunny of a body, neither one seemed to care that Greg hadn't put a condom on. About two ropes of cum into his orgasm, which followed Dolly's third orgasm—the first one had been from dry-docking and manual stimulation by both of their hands in the cab, and the second one during some perfunctory foreplay with stripping each other there in the high-rise condo—was when Dolly realized Greg was cumming into her pussy, which was pill protected from pregnancy but not from any potential STDs. Oops!
During the moments when Greg grunted and strained and Dolly squeezed his body with her finely trained body, he, too, realized he had just inseminated his step-mother. Again, their eyes met. This time, the look was shared, silently, for several moments. Then their lips met again. Each seeing, in the look from the other, that there had been, thankfully, safety in the familiarity of the unscripted sexual pairing.
By the time the sun rose over Miami, Dolly had tasted her step-son's seed, swallowing it, then kissing his pussy-coated lips after he'd gone down on her in a way his father never had. She had ridden Greg to another orgasm deep inside her womb, still fertile if not for her birth control pill, then she'd encouraged him to take her doggie style, and finally collapsed onto the bed for a lazy-dog finish from which Greg had pulled out and finished on her lower back as their arms and legs strained against each other.
"Greg," she started to inquire, but this time it was Dolly who was cut off, as Greg told her, "Dolly, I loved being with you. I want us to do this again, but I don't want to get in Dad's way. Can you be with both of us?"
She felt a twinge in her well-fucked pussy, her mouth kissing his flesh, tasting his sweat, inhaling his body's scent, her fingers playing with his six-pack abs and enjoying the sensation of his touch on her body. She knew Ben didn't begrudge her having lovers. But his own son?
"Never when he's in town."
"Agreed. And when he's not?"
"Then do as Momma says, Baby Boy."
They both burst out laughing, their lips met, and dry humping gave way to wet humping as Dolly moistened up to the feel of her young powerful lover. Her cries of "Oh God, Oh God," would have awakened the neighbors if the neighbors had still been asleep. They were loud enough, however, to drown out the sound of Ben's key in the door lock, after he had caught the 6 a.m. early-bird out on the morning after Logan had re-opened.
Purely fictional fantasy for your reading pleasure!