The summer was officially ending. The days were getting shorter, the nights were getting colder, and the Labor Day sales were ending. At Jupiter's, a hustle and bustle of busy shoppers flooded the store; or, at least, they had been. The shop was closing up for the night, and the only shoppers left were stragglers sorting through the left-behind deals from the rush earlier that day.
The owner of Jupiter's, Jillian, came from the part of the store with changing rooms, a dejected look on her face. Her short hair barely wavered in the cool air coming from the fans circulating above. As she walked, one customer couldn't help but notice her bouncing rear end in her tight pants, and admired her curvy figure. She may have been a middle-aged mother, but she could still turn heads in a pair of jeans and a simple v-neck.
She had hoped to find a certain anonymous guest in the changing rooms, but she was left hoping. Now, as her employees closed up at the front of the store, ringing up the few remaining shoppers, Jillian strode past, walking to the exit, her bag slung over her shoulder. Typically, she'd be the last person closing up the store; but today, she had plans. Plans that made her anxious.
Stepping out into the almost-cold air of the September evening, Jillian tried to let the slightest breeze quell some of her anxieties. She was supposed to be meeting with Michelle, one of her best friends. Typically, she'd love to do something like grab drinks with Michelle after a hectic day at the shop. They'd gab about work, and kids, and Michelle would complain about how her husband was always away on work trips.
But this time was different. Last week, Michelle had stumbled into Jillian's perfect setup with the gloryhole in the back of Jupiter's. Despite Jillian's best efforts, Michelle had inserted herself into that situation, and before she knew what was happening, Jillian was sharing a thick cock with her best friend.
Since then, she had been too afraid to look Michelle in the eye, much less talk to her. At their weekly book club, Michelle had joked about giving one character a blowjob. Normally, a wined-up mother making a sex joke at their book club wouldn't give Jillian any pause; but this time, all she could do was envision Michelle gagging on a fat cock an inch from her face, and how it felt when the cock shot cum onto the two of them. Jillian couldn't meet Michelle's gaze that night. Now, only a few days later, Jillian was dreading meeting up with her.
Was it a mistake?
Jillian thought to herself as she drove to Michelle's house. She'd been concerned ever since she'd shown Michelle the gloryhole, things had changed. Prior to this, Michelle was your average middle-aged woman. She was divorced, remarried, had a daughter and a stepson, and a rich husband she barely saw. They were normal, mature women living in a quiet suburb.
However, now, the dynamic had, expectedly, shifted after something as monumental as sharing an anonymous cock. As the book club had shown, Jillian had been on her toes around Michelle. Her friend was much more of a free spirit than the shy, reserved Jillian. Now, Michelle had seen Jillian effortlessly deepthroat a cock. Jillian had seen Michelle gag, choking down as she attempted to mimic Jillian. Things had changed.
Plus, Jillian was nervous that Michelle would spoil her secret. After the tense book club, Jillian practically jumped when Michelle tapped her on the shoulder as she was getting in her car.
"Are you busy on Monday?" Michelle asked.
"Monday?" Jillian repeated back to her, doing her best to steady her voice.
"Monday, in the evening, after work, do you want to come over?" Michelle looked casual, but her eyes flashed with something wicked.
"Um, I have to see if Iā" Jillian started, but Michelle cut her off.
"Come by my house. I need your help with something." Michelle winked, and then, without another word, simply walked away. Jillian stood stunned as her friend crossed the street to her car, got in, started the engine, and drove off. Jillian stood, frozen, overthinking.
Somehow, a few days later, Jillian now found herself pulling up in front of Michelle's house on Monday evening.
With a hesitant finger, she rang the doorbell. There was no going back now. After only a few seconds, the door was pulled open by a very eager Michelle, who invited her friend inside. In the glow of a crystal chandelier that told guests just how much money their family had, Michelle's house looked just as radiant as she did. Her shoulder-length blonde hair was tucked behind her ears, and she was wearing a blue tank top that made it easy to tell she had no bra on underneath; Jillian did her best not to stare. Michelle was wearing dark running shorts that tightly hugged her maternal hips. As Jillian followed her through the foyer, she couldn't help but watch her friend's ass bounce in the revealing shorts.
"No one's home," Michelle's words hung in the air thick as syrup, and Jillian felt a chill shoot through her. "Roger's off on another business trip. Annie and Luke are both gone for the night. We have the house to ourselves." With her whole family gone, the house seemed so empty. "Let's go upstairs." Michelle led and Jillian followed.
Upstairs, the hostess led her friend through double doors into the large master bedroom. She entered and sat down on the king-sized bed in the center.
"Come on." Michelle coaxed a nervous Jillian into the room.
"Look, Michelle," Jillian began as she followed, tentatively sitting on the edge of the bed.
"I want you to teach me how to deepthroat." Michelle stated, flatly. She was looking directly at Jillian, who refused to make eye contact.
"What?" Was the most the woman could manage.
"Look, Jill, we both know what happened a few days ago. I was there, you were there. There's no skirting that." Michelle was right. "I'd never seen anything like it! The way you were able to just take that cock... All the way down..." Her voice seemed to trail off as she reminisced.
"You want me to teach you..." Jillian tried to form a sentence, any sentence.
"How to deepthroat." Michelle finished it for her. "With this." She reached over to her nightstand and opened the drawer. From under an untouched magazine Michelle revealed a dildo, large, smooth, and dark blue. Jillian couldn't help but gasp.
"Are you sure?" Jillian asked, now more intrigued.
"Please?" Michelle begged. Jillian thought about it, and realized that, at this point, there really was no turning back anyway. She'd already shared a cock with this woman, there was no point in not just teaching her how to please her husband some more.
"Alright," Jillian sighed, pulling her feet up onto the bed and shifting to face her helpless friend. "Alright, I can teach you."
"Yes!" Michelle squealed with a giddy glee and punched the air. "Alright, here's how I usually do it." Michelle positioned the dildo in front of her mouth. "I just focus on opening my jaw as much as possible. Then I just stuff it in and..." She opened her mouth wide, and Jillian watched on as Michelle crammed the fake cock past her teeth. Only a few inches in, she gagged, and retracted, pulling the dildo out of her mouth with a cough. "Well, sometimes it works." She sounded defeated. "What do I do?"
Jillian couldn't help but feel bad for her desperate friend. "Well, for starters, I honestly think you're trying too hard. You just need to relax." She smiled, trying to take her own advice. "Here," she gestured to the spot in front of her. Michelle crawled over, handing her the dildo. "Sit here." Michelle sat, practically in Jillian lap.
