Hole in the Wall

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 I—" 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.

"Like this?" Michelle looked for reassurance.

"Perfect. Now," Jillian began. "Don't spend so much energy on making sure your mouth is open wide enough, then you're just too tense. Relax, breathe, and swallow the cock down. It's easier than you're making it out to be." Jillian leaned forward, pressing herself up against Michelle, feeling her soft breasts squish against her friend's back. She rested her chin on Michelle's shoulder, and their cheeks brushed as she spoke in a low tone. "Just relax."

"I'm relaxed." Michelle responded.

"Are you ready?"

"I'm ready."

Jillian didn't wait for her to overthink it. While one hand lifted the dildo in line with her

friend's mouth, her other hand reached around and took hold of Michelle's chin, delicately opening it in preparation. With a heavy breath, Jillian guided the fake cock into her friend's mouth, past her lips, barely touching her teeth. She could feel it running over her tongue, and pushed it further down. After a moment, Michelle gagged, and Jillian immediately pulled back. As Michelle caught her breath, Jillian watched a thick strand of saliva trailing from the fat tip of the dildo to Michelle's lip.

"That was already so much better," Jillian applauded her. "Was I too rough?"

"No," Michelle said. "I can do better. Again."

"Are you sure?" Jillian was hesitant, not wanting to push her friend too far.

"Yes. Let's go."

Jillian was now taking directions, and lifted the dildo back up, pressing it just barely against Michelle's puckered lips.

"Remember," she whispered in her ear. "Relax." Jillian pushed the dildo into her friend's mouth, exhaling a hot breath onto Michelle's sensitive neck as the dildo went further and further down her throat. Inch by inch, Michelle's throat accepted and enveloped the smooth

toy. Jillian's other hand rested on Michelle's thigh, and she could feel the warmth emanating from her friend's lap. "You're doing great."

Suddenly, from downstairs, the sound of the door bell ringing stung through the almost-empty house. Jillian froze, waiting, the dildo half-in Michelle's mouth. Michelle pulled back, letting the spit-covered tool slide from her lips.

"Who's here?" Jillian whispered.

"My order." Michelle smirked. Jillian felt her face get hot.

What does that mean?

She wondered.

Order? What isn't she telling me?

Michelle stood up from the bed and strode to the door. "You coming?"

Jillian was stunned, but did as she was told, and followed Michelle back downstairs, leaving the dildo on the bed. She wasn't sure if she was supposed to hide when Michelle opened the door, but quickly relaxed when she saw that it was just a pizza delivery boy, wearing the iconic red shirt of the local pizzeria. Curiously, Jillian noticed that he didn't have a box with him. Then, she got a sinking feeling.

"My order," Michelle spoke. "Come on in." She stepped aside and invited the young man into her home. As entered, she guided him through the foyer, into the living room, where Jillian was watching from. She blushed hard as she guessed what Michelle was up to.

The young man had scruffy blonde hair, and a decently-defined frame. He walked with confidence, showing himself to the dark leather couch on one side of the room.

"Oh my god, Michelle," Jillian muttered as she took a seat in a large armchair across from the delivery boy.

"You know, I've never delivered to two MILFs before." He smirked as he spoke. He looked like he permanently had a cocky grin on his face.

"Excuse me?" Jillian was aghast, seeing this young man, who looked just barely older than her son, comfortably calling her a MILF.

"What? I can't ignore what's in front of me." He made a crude gesture about the two women's voluptuous figures.

"Michelle!" Jillian was stunned.

"Alright, I think I should explain!" Michelle finally spoke, pulling her eyes away from the delivery driver on her couch. "I just thought, maybe, it would be nice for us to get some more... hands on practice. After that first time, at the wall... I can't stop thinking about it, Jill. I need more." She truly seemed desperate, her voice yearning as she spoke. She was hungry.

"And this is the solution?" Jillian asked.

"He's on call, it's what he does! Linda told me he's a great, um, service provider." As Michelle explained, Jillian couldn't help but roll her eyes.

"I mean, come on, Michelle, he's a kid!"

"I'm twenty-three." He chimed in.

"Well, honey, we're more than twice your age." Jillian informed him. He grinned back at her, and she noticed a bulge in his pants. "Oh my god!" She was shocked at his immediate reaction to her words.

"I'm sorry, ma'am, older women just really do it for me. And, I've learned, I really do it for older women. So..." He shrugged.

"Look," Michelle interjected. "Our friend at the hole in the wall isn't reliable. We don't know when he'll be there, when he won't. But this guy is, quite literally, on call for us!"

As Michelle spoke, the young man didn't hesitate to undo his belt, and shimmied off his pants and boxers. Jillian barely heard what her friend was saying as she fixated on the cock emerging from the delivery driver's pants.

"Holy shit." Michelle whispered. Jillian had no words. In his lap stood a thick cock, already fully hard, showing off his young virility. He could have been brothers with the stranger at the hole in the wall. Without a second thought, Michelle knelt down, positioning herself between his legs. With a steady hand, she reached out and took hold of the meaty cock before her. Her thin fingers wrapped around the girth, and she began to stroke, eliciting another cocky grin from the man.

"You sure you don't want any part of this?" Michelle goaded her friend.

"I can't believe you're doing this," Jillian remarked.

"Suit yourself." That was all Michelle offered before turning back to the young man in front of her. Without another word, she began to slowly stroke the shaft, feeling the smooth skin in her hand, planting a soft kiss on the tip. This was rewarded with a small pearl of precum beading at the tip, which the mother licked up, tasting the burst of salt in her mouth. Stroking faster, she kissed the tip again, her soft lips partially enveloping the head, before moving to the base of the cock, and licking up the length with her gentle, wet tongue. It was a long cock, and by the time she got to the top, she couldn't hold back any longer. Michelle took the cockhead in her mouth, past her lips, feeling it run over her tongue. Working her hands around the base, she stroked, sucking at the head, lavishing it with kisses and licks. The suction was strong enough to make the young man groan happily.

Meanwhile, Jillian couldn't pull her eyes away, watching, blushing, as her friend went to work on such a big cock. She felt a wet warmth in her pants, and had to readjust how she was sitting as she tried to ignore it. Nonetheless, Jillian watched as Michelle kept going.

The mother of two spit on the head of the cock and massaged it against the head of the cock, which throbbed against her ministrations. As she took the cock back into her mouth, Jillian couldn't help but notice how much her friend was completely ignoring the young man's large, full balls, which hung heavy. As she watched, Jillian noticed her mouth was watering.

"What?" Michelle's voice snapped Jillian to attention. "Do you have something to say, or are you just going to silently judge me?" Jillian had a thousand thoughts racing through her mind, but decided to just ignore all of them, and go with her gut.

"Come on, Michelle, you're just completely ignoring those balls!" She whipped. "Get in there!"

"Get in there?" Michelle was so caught off guard by the fact that her friend actually spoke up.

"Give them some attention!" Jillian suggested.

"Why don't you come show me what you mean." Michelle challenged her. Jillian immediately, noticeably, turned beet red. Despite that, she couldn't deny how badly she wanted to. Almost unconsciously, she stood up from her seat, took a deep breath, and walked over to the crowded couch. Kneeling down next to Michelle, she squeezed in between the delivery boy's legs. He smirked again, and his cock twitched as he eyed up the two older women in his lap.

"Well, don't just ignore them," Jillian reminded her friend. "They're sensitive too, and he'll love it." She took a deep breath, and the hot breath on the young man's cock made it jump. Jillian took hold to steady it, and, for the first time, felt how heavy and thick it was in her small hand. She gave it a slight, tentative stroke, feeling how smooth it was, barely coated in her friend's spit. "Don't be afraid to roll them around in your hand."

Michelle watched as Jillian took hold of his large balls, barely able to hold both at the same time. In her hand, Jillian could feel how full they were.

"Give them a little tug... Just play with them, lightly. You'll control his attention," she gestured up. "Look." Michelle looked up from her friend's working hands to see the man completely enraptured. "Give them a little more love, if you want."

Jillian dipped her head and, without hesitating, licked one of his balls, eliciting a pleased groan. She opened her mouth and popped one in, causing the the young man to ball up his fists and moan. Jillian rolled her tongue across it, sucking softly, before switching to the other ball, making sure to give both the attention they deserved. As she worked, she gently stroked the tip of his cock.

"Don't forget that you can do two things at once." Jillian instructed. "If you're sucking his cock, play with his balls. If you're working on his balls, you should be pumping his cock, too. It'll drive him wild."

"Yeah," the young man whimpered.

"Yeah?" Jillian teased him as she stroked his cock and kissed his balls.

"Y-yeah," he could barely muster.

"That said, there's two of us." she nodded to Michelle. "That means that one of us can give him attention here..." Jillian gave his heavy balls a soft kiss, and he tensed up in response. "And the other can get to work on that cock." She took her hand off the cock and tucked a finger under Michelle's chin, bringing her mouth to the fat cockhead hovering before them.

"Oh, right." Michelle had forgotten that she could partake, so completely aroused by Jillian's teaching. She placed a hand around the shaft and guided it into her mouth, sucking softly. Michelle stroked the cock quickly, rhythmically, licking the underside of the head as she sucked back and forth, back and forth, lavishing love across the sensitive tip. Jillian switched balls, giving them a slight squeeze in between, and the delivery driver couldn't help but spill a mess of more precum into Michelle's eager mouth.

"Oh, come on, Michelle. You can do better than that." Jillian taunted her friend. "You showed me, upstairs. You know what to do." She pulled back, steadying the cock at the base, aiming it at her friend's mouth. Michelle closed her eyes, centered herself, opened her eyes, opened her mouth, and descended onto the waiting cock. Jillian watched as it went, inch by inch, into her mature mouth; despite her best efforts, Michelle could only get about halfway down before gagging and pulling back, coughing.

"I just can't do it as well as you can." Michelle admonished, wiping spittle from her chin.

"You're so close, you just have to let go." Jillian encouraged her. "Here, do as I do." She pushed the other woman aside, centering herself in front of the cock. With another deep breath, she leaned forward, swallowing the cock down, inch by inch, her lips running down the smooth skin. The young man gripped the couch with white knuckles, gasping. Jillian kept going, until she'd taken it to the hilt, his cockhead knocked against the back of her throat, and her lips were pressed against his lap. She gave his balls a soft, playful tug, and he moaned loudly, trying his best not to burst to early, his cock throbbing hard, deep in her MILF throat.

"Holy shit," Michelle whispered, almost unconsciously. With a wet exhale, Jillian pulled back, letting the large cock slip from her mouth, wet, throbbing, and covered in strands of her spit, which draped from his tip to her lips. He practically melted into the couch, cock cock hard in his lap in a mess of saliva, with a dark red lipstick ring on his lap.