A Gurl in the Making Pt. 02

Story Info
An introduction of Aunt Cathy's friends.
2.7k words
4.64
4.7k
12

Part 2 of the 2 part series

Updated 02/23/2024
Created 02/22/2024
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Editor's note: this fictional work contains scenes of completely fictional incest or fictional incest content.

** This story would not have been possible without the help of Daddysgirlfl - Her editing and guidance helped me feel confident in finally sharing part 2! We'll see where we go in part 3 **

Kelley slipped into the passenger seat of his Aunt's convertible and patiently waited for her. She had insisted on changing into a new outfit and he had taken a quick shower before they left for the mall. For a couple of weeks after he had first moved in they had kept their distance but it felt right to finally be spending some quality time with Cathy.

Cathy came out wearing a form-hugging tulip skirt and a white crop top that just revealed her torso. Kelley's eyes followed her as she slid into the car.

Before taking her seat behind the wheel she turned around showing how the skirt hugged her ass, before lowering into the seat. Kelley bit his lower lip as her skirt rode up to her mid-thigh, exposing her purple panties. When Cathy cleared her throat, Kelley looked up and away, quickly, feeling his cheeks turning pink. Cathy smiled to herself as she noticed how fast Kelley jumped from his seat; knowing that he had been caught.

She reached over turning on the radio to the local NPR station and putting the roof down letting their hair blow in the wind. They sat quietly as she drove towards the mall. Kelley continued to watch Cathy's legs from the corner of his eye but did his best to not be blatant.

Cathy parked the car far away and walked together. It was a nice day and the cars zipped by. Kelley walked slightly behind, his Aunt, as they approached the stores. It was a cute downtown area with coffee shops and cafes.

"It's so nice and cute here, Cathy. I didn't realize that this was even a part of your little city!"

When Kelley noticed the signage for The Pleasure Chest he raised an eyebrow and wondered where his Aunt had chosen to take him shopping.

Cathy decided that she wanted some coffee before they ran into a couple of stores and led Kelley into a shop that her friend owned The Hideout. When they entered the shop, Cathy smiled at the barista and asked if Dawn was around. The barista waved them to the back office, and they knocked on the door. Dawn opened the door and looked them both up and down.

"Well, hey, there Cathy. Come over to enjoy my black coffee or look for a little extra cream?"

Kelley felt his brow furrow and he looked at his Aunt with raised eyebrows. What was this woman going on about? But he saw Cathy smiling and he decided to go with whatever she had planned.

Dawn stood up and walked around her desk approaching Kelley with a wicked grin. She was tall and black, and her latex leggings hugged her firm ass. She must have known how sexy she was as she walked up to Kelley and put her hand on his chest, her nails digging into his skin. Unable to contain himself Kelley let out a soft moan as her fingernails dug deeper into his skin. His eyes darted over to where Cathy stood with her back turned to them.

But Cathy did not seem to have noticed anything amiss, even when Dawn leaned into Kelley. Her breath was hot against his neck, and he felt a shiver run down his spine before she stepped away.

Cathy turned back to face the two of them and smiled as she how flushed Kelley's cheeks were.

"Dawn here is a dear friend, Kelley. She'll be coming over this evening to enjoy a night of being served and waited upon. Of, course, you will be doing the waiting as a part of your service this evening."

Cathy stepped forward and placed her fingers where Dawn's nails had been digging into Kelley's skin and massaged his chest tenderly. Kelley could feel his heart pounding through his chest and his hands felt clammy as he realized that he was in for an interesting evening. Just as he was starting to step away from Cathy, he sensed Dawn standing just behind him. He was a little startled as she placed her hands on his hips and squeezed his ass.

"Why don't you come with me for a minute, honey? I've got something that I think you'll like."

Dawn led Kelley further back into the store. He hadn't realized just how big the shop was when they first walked in. Dawn must have purchased the business next door so that she could expand her operation. She smiled at him as his eyes adjusted to the lighting.

"Now, I know your Aunt is waiting for you but I think the next time you're bored you should come by for some fun."

She led him into a huge space that was lit in purple and pink lights. There was a bar in the far corner fully stocked with alcohol. A few tables were spread throughout the dining room. She nodded to the back wall and smirked.

"We have a small theater here that you're welcome to use. Movies are usually shown a couple of times a day and we have more..." Dawn bit her lower lip and ran a finger over Kelley's chest again, "adult in their nature. If you understand what I mean. We always recommend wearing shoes unless you don't care about the sticky floors."

Kelley smiled hesitantly thinking that he had caught the drift, but Dawn only laughed at him and spun around. Kelley's eyes followed her as she started to lead him back to where his Aunt waited for them. As they passed the restroom Dawn paused and placed her hand on the door.

"Here, honey, why don't you relieve yourself before we go back to Cathy? I know you didn't expect to make this stop on your trip - so you may as well take a chance while you have it."

Kelley raised an eyebrow but took Dawn's advice and stepped into the bathroom. Dawn let the door close behind him and she smiled to herself as she waited patiently. Kelley was surprised to find that it was a unisex bathroom with no urinals and several stalls.

Kelley entered a stall and realized that while he normally would have stood to pee, he was not comfortable doing so in a shared bathroom. He bent forward quickly checking that the other stalls were empty before taking a seat on the toilet and letting his hot stream of piss splash in the water.

Just as he was getting ready to stand up and zip his pants back up Kelley heard the door to the restroom open and someone walk in. They didn't say a thing as they made their way to the stalls and Kelley felt himself get slightly heated as he realized that whoever had entered had chosen to occupy the stall immediately next to him. Kelley sighed. The shoes, just barely visible underneath the stall divider, were a black chunky pump and there was an anklet around the person's ankle. As they settled onto the toilet, they dropped their panties, and he was thrilled to see a leopard print Brazilian panty.

Kelley could feel himself starting to get excited despite knowing that this was highly inappropriate--what was he doing spying on a woman in the stall next to him? Then he heard the heavy splash of a heavy stream of pee against the toilet bowl and he stood up knowing it was time to leave. He lingered just long enough for the peeing to stop and smiled to himself, reaching down to squeeze his engorged cock.

Kelley left the bathroom and pulled out his phone. It was getting to be late morning if they were going to be ready for Cathy's friends to come over in the evening there was going to be a busy afternoon cooking, cleaning, and getting ready for the guests. Kelley looked around the hall to see if he could find Dawn and didn't see her. Instead of waiting, he walked back to where Cathy was waiting.

"Did you lose Dawn back there, honey?" Cathy smiled and raised an eyebrow as she eyed Kelley's disheveled appearance.

Kelley shrugged his shoulders. "I'm not sure--I had to go to the bathroom and when I came out, she wasn't there. Not sure what happened to her."

Just then Dawn appeared. Kelley's eyes moved over her body again. She walked up to Cathy holding out her arms for a hug. As the two women embraced each other Kelley's eyes moved over Dawn's tight-fitting leggings, and he smiled as he noticed that he could make out the outline of her panties. He also noticed that the heels that she wore matched the pair of heels that he had just been able to see underneath the stall divider. He raised an eyebrow and looked away so as not to be noticed.

Dawn turned to him, and her fingers went to his chest again, firmly digging her nails into his skin as she wrapped him in a brief hug--she reached down and gently squeezed his ass, before giving him a quick kiss on his cheek.

"It was so lovely to meet you, Kelley. You'll have to come to visit me again sometime and I'm sure I'll see you tonight for our lady's night!"

Cathy led the way to a cute boutique, The Pleasure Chest. When they entered the store, Cathy nodded for Kelley to go browse around while she picked out a couple of items for herself. Kelley was floored by the number of bright neon colors and the splashes of pink and purple. Everything seemed to have skinny straps, frills, or gemstones. There were a couple of displays that featured adult-oriented costumes for roleplaying, and an entire wall devoted to dildos. The dildos came in various sizes and his eyes lingered on the big black dildos that were nearly twice as thick and probably twice as long as his cock.

Kelley couldn't believe that his Aunt had brought him to this store. But obviously, there was something more to Aunt Cathy than he had previously suspected. Kelley looked up as the sale associate came over to greet him and he smiled recognizing his Aunt's friend Monique. She was a tall Mexican woman with dark hair with blonde highlights. Kelley had met her on a couple of occasions when she had come over to pick up his Aunt for a night out.

Kelley was starting to notice a pattern with Cathy's friends, as Monique placed her hand on his chest and greeted him with a quick hug and a peck on the cheek. She pulled back and with her soft Spanish accent poked a little fun at Kelley.

"Hola, Kelley. It's so nice to see you out with Cathy! I hope she is showing you a good time. She told us that you're going to be home tonight for our girl's get-together." Kelley nodded and Monique's smile twinkled in her eyes as she laughed, "We're excited to learn all of your naughty secrets!"

Monique led Kelley around the store, and they lingered for a couple of minutes in the toy sections. Monique couldn't help but grin as she saw Kelley's eyes lingering on the wide array of thick plastic cocks that she had displayed. She walked up to one of the open displays and wrapped her hand around it.

"Are these what get you excited, Kelley?"

Kelley blushed but knew that his interest had been piqued. He had never been exposed to so many confident and sexy women who were so comfortable with their sexuality and who seemed so open to exposing him to new experiences.

"I've..." he stammered slightly, "I've never really been exposed to such an open environment and, well, I guess I didn't expect this from Aunt Cathy's friend. My Mother always said that she was so..."

Kelley trailed off and looked away. His eyes lingered momentarily on Monique's hand wrapped delicately around the big plastic cock. Monique allowed her fingers to slowly trace its outline, and she caught his eye as she teasingly fondled the balls before letting go, as if this was all perfectly normal behavior.

"Come on, I'll show you back to the fitting rooms. I bet your Aunt needs some help."

Monique walked in front of Kelley on the way back to the fitting rooms. Kelley admired how her hips swayed--her ass clearly on display. She was accentuating the movement of her ass and he couldn't help but admire her.

Kelley sat down outside of the fitting rooms as Monique went to help Cathy. He pulled out his phone to check his emails when he noticed that Monique had left a slight gap in the curtain of the dressing room. From where Kelley sat, he had a clear view of his Aunt looking at herself in the mirror, and of Monique's hand pressing on Cathy's lower back as his Aunt removed her top. She'd picked out a grey bra, with matching panties. Her areolas are visible through the thin material and Kelley sits back, crossing his legs, enjoying the view.

Monique peeked in the mirror and smiled. She could see Kelley squeezing his thighs together and knew that he must be enjoying the view. Biting her lip Monique held out her hand to his Aunt and spun her around admiring the bikini that she had chosen-- a bright pink Brazilian bottom that rode up her ass showing off her perfect cheeks with a matching lace-up bandeau top. Kelley watched as Monique's fingers traced over Cathy's exposed back and she wrapped her arms around Cathy's waist. Pressing her chest against Cathy's back Monique leans into the back of her neck and softly whispered.

"I... I think your nephew is a bit of a perv. Are you enjoying the attention?"

Cathy looked up at the mirror, out of the corner of her eye, and smiled to herself. She could see Kelley sitting on the chair outside of the fitting room. She bent forward, her bikini-clad bottom pressing into Monique's waist. Then she straightened herself and turned to face Monique.

She brushed the hair from Monique's eyes and gave her a sloppy kiss her eyes not leaving the mirror as she watched Kelley squeeze his thighs together repeatedly. Cathy leaned close to Monique and whispered into her friend's ear.

"Mm, I think I am enjoying his attention. Wait until you see what I've picked out for him to wear to our party tonight."

Cathy pulled back from Monique and playfully smacked her friend's ass. She could not help but add an extra squeeze as she turned to put the rest of her clothes back on. Monique giggled and turned back towards the door, headed back into the shop front. She smiled as she opened the door and saw that Kelley must have gotten up and left his seat.

She found Kelley browsing through some of the bikinis and she takes note that he seemed to have his eyes on a pair of pink ruffle bottoms and a high waist matte nude thong. She admired his taste and noted how his fingers linger on the material and as he picked them up to look at the backside. She stepped forward, making sure that Kelley knew she had been observing him.

"Well, aren't those cute darling?" Monique winked and went back to the counter. "I'm sure your Aunt will be out shortly. Why don't you grab a coffee for the two of you? I'm so looking forward to the party tonight!"

Kelley took Monique's suggestion and went out to buy a coffee for Cathy & himself, just as Cathy emerged from the fitting rooms. Monique bit her lip as she waited to hear the bells on the door jingle confirming that Kelley had left. She looked up and walked over to wear Kelley had been lingering among the clothing racks.

"Mm, Cathy you'll never guess what I noticed when I came out of the fitting rooms."

She picked up two bottoms, that Kelley had been touching, and waived them towards her friend, "I think you should purchase the two of these for your nephew. Maybe we'll all get a little fun tonight!"

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
AnonymousAnonymousabout 10 hours ago

So engaging! Getting very steamy, savouring the moments here, thank you!

AnonymousAnonymousabout 2 months ago

Loved it and the anticipation for all of this to continue is overwhelming. Loved the BBC part and wondering if BBC may be in Kelleys future.

AnonymousAnonymous2 months ago

I loved the premise but the suspense and over-descriptive blah blah blah parts have left me looking for more sex oriented fare! Cathy and Don were hot with the BBC, wish he'd sucked it, too, and I'm waiting for Kelly to get dressed up but nothing yet!

Kathryn65Kathryn652 months ago

Mmmmmm please find the time to write some more of this deliciously scripted scrumptious story, I can’t wait to read what happens next for your lucky naive hero xxx

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Lost Suitcase Adventure Lost bag & friend's clothes fit better than her husband's.in Transgender & Crossdressers
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
Teacher Surprise College student bumps into his high school teacher at a club.in Transgender & Crossdressers
Boyfriend Turned Girlfriend Ashley turns Matt into Maddie for the first time.in Transgender & Crossdressers
Popping His Cherry She finally makes him her woman.in Transgender & Crossdressers
More Stories