AUTHOR'S NOTE: This story contains a few brief references to male bisexuality as well as anal fingering. If this isn't your cup of tea, please keep looking for something else to read. As always, any and all sexual activity takes place between characters who are 18 and above. Much thanks to anyone who keeps readings.
I
There were a lot of other things Jimmy could've been doing that hot summer day. The handsome eighteen year old could've been playing basketball with his friends, or playing his favorite video game back in his room. Or, he could've been watching internet porn and spending the afternoon rubbing out as many loads of cum as he could manage from his teenaged cock. But he was spending the afternoon with his mother at her friend's swimming pool, and being around two heavily thick, older ladies in bikinis was better than any porn Jimmy had ever seen.
He knew he shouldn't be looking at his own fleshy-built mother in a bikini and getting excited, but he couldn't help it. With her fine, black hair that was cut barely above her shoulders, she was the prettiest of all his friends' mothers and most of the ladies her age that he'd seen anywhere. She was what most people would call a chubby lady, but she had the sweetest, sexiest shape, almost like an oversized Barbie doll with a heavy, round pair of amazing tits that looked big even on her large body. Diane, Jimmy's mom, was exactly the kind of woman that made his young cock stand up and ache with need.
He couldn't explain why the big girls made him feel the way they did, but he didn't care. He loved the feelings they brought about in his virile, young body. He loved the way looking at their big, curvy bodies made his hot dick pulse with need. Maybe it was from being surrounded by big, pretty females at home.
Chanel, Jimmy's older sister by three years was even prettier and bigger than their mother. Fortunately, Chanel wasn't with them today or Jimmy would never be able to get out of the pool. It was bad enough with Brenda, Diane's friend, being there. But of course it was her house, and Jimmy never minded being around Brenda's pool when she was out sunbathing and drinking wine with his mother. A sandy blonde with long hair, Brenda was almost as pretty and almost as chubby and thick as Diane. She knew she was a thick built woman, and she wasn't the least bit shy about flaunting her curvy body in swimwear that was usually more typical of thinner, younger girls.
Thanks to Brenda's audacious example, Diane and Chanel would always wear bikinis around the blonde woman's pool whereas if they were anywhere else they stuck to less revealing one piece swimwear. But Jimmy thought ladies as big as his mother and sister should always wear revealing clothes. Maybe they weren't the type of girls the media held up as a standard of beauty, but Jimmy thought they were irresistible. It wasn't right that girls like them should ever feel like they should hide their natural beauty. His feelings about them were probably influenced by the fact that he was the only male in the house and his curvy mother and sister doted on him like a prince. And he loved every second of it.
Brenda, on the other hand, was bold and flirty, and she always treated Jimmy like he was special. He figured maybe it was because she didn't have a son of her own, just a daughter about Chanel's age who looked like a younger version of her mom. But Brenda's daughter was rarely around when Diane took her son with her to spend an afternoon by the pool. She usually only showed up when Chanel was there since the two were also friends. Jimmy didn't mind, though. He was perfectly happy to spend a day with a pair of fine, full-figured MILFs, even if one of them was literally his own mother.
Jimmy's friends kidded him about being a mama's boy sometimes, but that wasn't the case. His father had left the family a few years before, and both his mother and sister and treated him more and more like the man of the house despite his age. It wasn't as if he was expected to take over for his absent father, but he was there for his mother and sister, always loving and supporting them throughout the upheaval in their lives. And he was there for his sister just as much as his mother, if not even more. He loved them both and felt protective of them.
Jimmy never got along with his father, but for that matter, not many people did, either. He never spent a second missing his dad, and he liked having the role as man of the house and adapted to the change in family dynamics easily. As a result, his mother and sister who had always loved him dearly just became more and more proud of him. And on days like this when he went with his mother to Brenda's, Diane could relax and not worry about drinking a few glasses of wine since Jimmy was right there to drive her home if she had a few.
That day, Diane and Brenda were both drinking while Jimmy alternated between getting some sun and swimming laps to stay in shape for his swim team. He had competed all through high school and was already accepted onto the team for when he started college in the fall. He was about average in height with a generally slender build, but swimming and basketball kept him in great shape. He knew the girls in his family noticed his excellent physical condition, and that Brenda noticed, too.
He liked the attention they usually pretended not to be paying him. It made him feel good. He'd even caught Brenda's daughter checking him out, too, even if she didn't seem to like him very much. He often wondered if they noticed the way he looked at them, too.
The sun was really strong that day, so after an hour or so Diane and Brenda moved their lounge chairs into the shade of the awning that was set up not far from the pool. Being the middle of June, both women already had deep, bronze tans, and Jimmy thought they looked amazing, especially his big, gorgeous mother.
Unlike Diane, Brenda was married, but her husband was rarely ever there since he was usually travelling for his high-powered job. Today, the neglected, voluptuous wife was being even flirtier than usual as she heaped compliment upon compliment on Jimmy, stoking his natural male ego with a coy smile. Diane shot disapproving looks at her friend more than once, but she never said anything to stop her.
Jimmy wondered whether his mother was just being protective or if she actually felt a little jealous of Brenda's wandering eye. He secretly hoped it was the latter. Not that anything could ever happen with his own mom, but the possibility that she might look at him as a sexy young man and not just her son made him feel good. It made him feel like that much more the man of the house. He did notice, however, that Brenda kept filling his mother's glass repeatedly while only sipping lightly on her own.
After finishing most of a bottle of wine, Diane started getting drowsy and ended up dozing off on her lounge chair. Jimmy caught Brenda checking on the brunette a few times as if she was making sure the other woman was really asleep. Finally, the plump blonde flashed the boy a sexy smile.
"Jimmy, darling, could you come inside with me for a couple of minutes? I need your help with something," Brenda said.
"Oh, sure, no problem."
Jimmy was always ready to jump in when a hot, curvy lady needed help. As he followed Brenda inside, he noticed she was walking more slowly than normal and letting her fully rounded hips sway heavily from side to side. He couldn't take his eyes off the way her large, globular ass looked as she walked, forcing the fabric of her bikini into the deep crevice between her impressive cheeks. He tried to look away but he couldn't. The woman's ill-fitting bikini was now riding up her ass like a thong. Brenda was boldly teasing him, and he was afraid of getting a hard on in his speedo that would've been impossible to hide. It wouldn't be the first time he'd gotten a hard on around his mother and Brenda, but usually he could just dive in the water and keep it hidden until it went down.
As they walked into Brenda's living room, she took a couple of cautious glances out through the glass double-slider at Diane, who was still dozing. Jimmy expected his mother's friend to ask him to change a light bulb or move a piece of furniture, but she went to her couch and sat down.
"Come stand over here, Jimmy," the blonde said, nodding to the spot on the carpet right in front of where she was sitting.
The handsome teen took the place Brenda indicated and couldn't help looking down at the impressively smooth, deep cleavage bulging up from the top of her scant bikini. She caught him gazing at her tits and smiled at him like it was perfectly okay to stare.
"Uhhh, what did you need my help with, Mrs. Fuller?"
"Oh, Jimmy, you're a man now. Call me Brenda, okay?"
"Sure, ummm, Brenda."
