A Good Use of That Squishy Diaper
January 27, 2023
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February 13, 2023


“Two pitchers of chocolate martini, Penelope,” said Julia.

“Make that three,” chirped Lucinda, who seemed unable to take her eyes off Penelope’s pretty panties under her skirt. “And a bottle of the finest champagne.”

Penelope carried the pitchers into the expansive living room while Brenda and Anabelle were coming down from Brenda’s bedroom upstairs. 

Following Brenda’s instructions earlier, Penelope had donned the black babydoll lingerie dress and matching backless panties Brenda had picked out for her. It was a hip-length dress, translucent below the bosom, with fur trimming along its hem. Brenda mentioned that the provocative quality of the outfit was essential for what she had planned for tonight.

Once everyone had converged, Penelope set off about the living room, a pitcher of martini in one hand and two empty flutes in the other, some soft music playing from the stereo system. Lucinda was perched on the armrest when Penelope carried the pitcher over to her side. Penelope hadn’t finished pouring Lucinda’s drink yet when she felt Lucinda caress her ass cheek before landing a stinging slap on the spot.

Lucinda giggled. “Your cheeks are just the softest thing, Pen.”

“Ow! Hey!” Penelope whined, nearly spilling Lucinda’s drink. “Here,” she offered, blushing, and moved on to Julia, who had nestled herself against Lucinda’s side. “Here you go, Julia.”

“Thank you, Pen,” Julia collected her flute with a mischievous smile before sending Penelope off with a raunchy slide of her fingers between the sissy’s ass cheeks. She nudged the plug that rested inside her sissy pussy before giving her another smack and sending her off with a low laugh.

When it came time for Anabelle and Brenda to be served their drinks, Anabelle slipped one hand under Penelope’s dress and stroked her clittie through the thin satin of her panties. Brenda raised one hand, indicating she didn’t want to be served. Penelope set the pitcher down on the small centerpiece table and stood in one corner, her clittie subtly dripping and soaking up her panties in the process.

“Girls,” said Brenda, standing to her feet as she started to address the room, “thank you all for coming. Now, everyone knows why we’re here, right? Everyone except Pen, of course.”

That provoked two, then three giggles.

Penelope swallowed the lump in her throat upon hearing her name, her heart thumping loudly against her ribcage. When she raised her head to look round the room, she found that they were all looking back at her, even Brenda as well, their roguish smiles telling of some wicked jest that Penelope somehow knew she would be the center of.

OhPenelope,” Brenda called in a singsong voice.

“Yes, Mistress?”

“Come here.”

Ooh, what do you think will happen? Why don’t you click here to read the rest and call anytime to tell me how you liked the story?

Aunt Brenda


1 Comment

  1. […] (First part) Penelope slowly shuffled until she was standing before Brenda, fingers twiddling behind her back as she looked down repeatedly, avoiding Brenda’s gaze. “Yes, Mistress?” “Close your eyes for me and hold out your hand.” After she obliged, Penelope felt a cold metal ring clasp around her left wrist. It wasn’t until she was restrained that she realized that one of her hands had been cuffed. And then she led her toward the center of the room, her eyes shut tight, unseeing. “Get on your knees,” Brenda commanded. Penelope obliged again. Brenda’s hand was pressed against her back, pushing her down until her torso was flat against what felt like the coffee table. And then she felt the second ring of the handcuff clasp around her right wrist before she heard Brenda say: “There, all done. You can open your eyes now, Pen.” Penelope opened her eyes to find that she’d been right about being handcuffed to the small coffee table in the middle of the room. She turned her head to look at the couch, where Julia, Anabelle, and Lucinda were each in the process of fitting on strap-ons of varying sizes and colors around their waist. Brenda’s strap-on must have been eight inches long, the rubbery girth lined with ridges and vein lines. Stroking the rubber shaft, Brenda drew up behind Penelope’s rear, her fingers pushing through the slit in Pen’s panties to grasp the base for the plug filling her ass. Brenda twisted it back and forth, pulling the bulb to its widest part and dragging her other fingers across her sissy’s stretched rim. Penelope shifted and moaned as her pussy was played with, and nothing could hide her embarrassed blushing when she squeezed tight enough around the plug to have it pop out into Brenda’s hand. Her mistress, along with everyone else, let out a throaty chuckle at that. “Looks like Penelope here is more than ready for something substantial to fill that greedy hole!” Penelope heard a small thud that must have been the plug dropped to the floor, then the tip of Brenda’s cock pushed inside her, spreading her pussy much farther than it already was. She bit down on her lip as she was stretched out near the point of pain, but it still felt so good that all she could be worked her hips back as much as she could, trying to get even more of that cock inside of her. Brenda noticed how cock hungry Penelope was and swiftly reached out to seize her sissy by the hair before pulling backward with force. Penelope’s hips snapped back, her cheeks slamming hard against Brenda’s abdomen. Then Brenda pulled out and forced herself back in and all the way. Her thrusts had become increasingly aggressive, and even as Penelope’s tight walls couldn’t decide if the fat cock needed to be squeezed out or pulled in further, it was Brenda herself who was in total control. The stimulus from everything soon had Penelope screaming as she came. “I’m cumming, Mistress!” Penelope moaned loudly before inevitably coming under the trembling influence of her first orgasm of the night. “Fuck,” Julia breathed from the couch, “that was like the hottest thing ever.” “My turn!” Lucinda announced before quickly mounting Penelope just as Brenda was standing to her feet. After Lucinda had finished, Julia came in next, and then Anabelle. And by the time the four women were done with her nearly an hour after midnight, Penelope could hardly walk two feet across the room. The ladies cleaned her up and tucked her into bed, telling her what a good sissy slut she was, and she smiled at the praise as she slid into sleep. […]