Cheerleader Chronicle Ch. 15

Story Info
If you give a MILF a makeover does she have sex with you?
5.7k words
4.56
45.7k
19
0

Part 15 of the 21 part series

Updated 10/18/2022
Created 09/08/2012
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
tk5555
tk5555
719 Followers

Thanks to my editor Cheer_Smartie526 for the corrections, advice and especially creative suggestions.

Rick turned around at the sound of his name to see Courtenay's mom waving at him. He returned her greeting and she began walking towards him. For a woman in her mid forties, she looked fantastic. He could certainly see where Courtenay's looks came from. He could also see where her big tits came from. Mrs. Venditti dressed like someone ten years younger, but managed to pull it off quite well. Her shirt fit snugly, but was not trashy. Her skirt was far enough above her knees to show off her legs.

"I still want to take you up on your offer", she said, "or did you think I forgot?"

"G-g-great,' Rick stammered, wondering what she was talking about.

"I have the rest of the morning free. Are you available?" she asked.

"I think so", Rick said, glancing at his phone, tapping on it to bring up the calendar. He wondered if he had offered to do some yard work.

"There is a shop down the street with a nail color I have been dying to try out," she gushed.

Suddenly it all came back to Rick. When he had done Courtenay's makeover, and done Courtenay as well, her mother had been very impressed by Rick's manicure and pedicure skills. Rick relaxed; there were worse ways to spend a Saturday morning. He also remembered that Nancy had told him Alexis Venditti was a swinger. Rick was not sure if she was joking or not. Mrs. Venditti did not look the part.

"I think I can work you in, Mrs. Venditti," Rick replied.

"Please, call me Alexis. You are not a kid anymore,' she insisted.

"Okay Alexis, a mani and a pedi today?'

"That would be a good start," she answered.

Rick paused, thinking about what Nancy had said. He felt his cock stir a bit and he looked at Alexis's impressive cleavage. He shook his head, there was no way Alexis Venditti was a swinger.

"What else did you have in mind?" he inquired.

"Don't worry, you don't have to give me a spray tan", she laughed, seeming to delight in his discomfort.

"Okay..." Rick paused, not sure how to reply to her remark.

"How about we head to the shop down the street and I will see what strikes my fancy. If I pick something you don't want to do I will put it back?"

Alexis smiled as she walked down the street with Rick. He was obviously conflicted, which was exactly what she wanted. For a week she had bitten her tongue each time she wanted to tell him she knew how Courtenay's makeover had gone. She had returned to the house early and heard them fucking, but decided to keep their secret. She really was impressed with Rick's work with makeup. But she was more interested in his other skills. Alexis wondered if Rick would notice her nipples poking through her shirt. She pulled the material away from her body, it would be better if Rick did not know how aroused she was until later.

Rick followed Alexis into the beauty supply shop. The round shape of her ass was mesmerizing, another genetic trait she had passed down. He still did not believe what Nancy had said about Alexis being in an open relationship. At best he could leverage this nail job into something from Courtenay; and at the worst Alexis might buy him lunch for his trouble. If he was lucky he might get a nice view of her cleavage when he painted her nails. She handed him a basket and they started down the aisle. The first stop was nail polish. The first thing she selected was a vivid red nail polish. Rick looked at the bottle before he placed it in the basket. It claimed to have color shifting properties. He shrugged and placed it back in the basket. He glanced up to see Alexis heading down the other aisles. She was in the skincare and shaving section. Rick's heart skipped a beat when he saw her eyeing the bikini and leg waxing supplies.

"I tried waxing my legs once; the wax was just too hot. I don't know how people do it. I just have to do it old school with a razor. Is leg shaving a service you offer?" She asked.

"Honestly I have never shaved another person, but I'm pretty good with my own face. I am willing to give it a try," he replied.

He watched as she grabbed a can of shaving gel, noting that it was for sensitive skin. Rick wondered how far up her legs she wanted him to go.

A little further down the row she was perusing oils.

"Does the pedicure include a massage?" she asked innocently.

"It does now," Rick answered cheerfully.

Alexis reached for a bottle of Vanilla scented massage oil, and then hesitated. She placed it back on the shelf. She wanted more than vanilla today. Her eyes surveyed the shelf. Rosemary, Lavender, Cinnamon, all too tame. Finally she found what she wanted, Spicy Clove and Amber. She plucked it off the shelf and laid it in the basket. She wondered if Rick would be up for what she had in mind. The oil was the last thing on her shopping list. She took the basket from Rick and instructed him to wait for her outside. The cashier probably would not think anything of her purchase, but it was probably best that Rick not be next to her at the counter.

"Where is your car?" Alexis asked as she exited the store.

"Actually, I am on my bike today... you know, save the planet, get in shape, yada yada yada," Rick answered.

"Well, I'm in the truck today, so I am afraid I have undone you planet saving. You can toss your bike in back and ride with me if you like," Alexis said.

"Okay, thanks," Rick replied.

During the drive to her house, Alexis casually mentioned that the rest of her family would be gone for the next few hours. She tried to gauge Rick's reaction to that news, he seemed happy about it. She could not help mentioning how excited she was about the new nail polish. She thought it would make her look absolutely irresistible. They arrived at her house and she led Rick upstairs to the master bedroom.

"My vanity is probably the best place to do this," she said as calmly as she could. Having Rick in her bedroom had aroused her more than she expected. She wanted to keep Rick guessing her true intentions for as long as possible.

Rick stopped to look around the room. It was fairly plain. The room was dominated by a king sized four poster bed. The room was in the corner of the house. The back wall had two large windows looking over the back yard, along with French doors leading out to a small deck. The other outside wall had smaller windows that looked onto the street. There was a small night stand on each side of the bed, a flat screen TV on the wall opposite the bed, and two walk in closets. Three large skylights filled the room with natural light. With the curtains on the back windows open the room felt more like a deck than a room. Along the back wall was Alexis's vanity. Lastly there was one other door that led to the master bath.

She handed him the bag of supplies, "Could you unpack these? I'm going to change into something better suited to a makeover. You'll need to shake that polish up; it's pretty bad about separating. Test it out on something to make sure it is mixed."

Alexis stepped into the bathroom, leaving the door slightly ajar. If Rick wanted to he would be able to spy on her as she changed. She removed her shirt and bra. Her nipples were swollen to twice their normal size. Alexis considered her choice in what to wear. She had a kimono that would be perfect if she wanted Rick to know what she really wanted him for. She also had a short terry cloth robe that could mask her nipples and did not scream about her desires. She slipped out of her shorts and ran a finger between her legs. Her panties were already damp. Alexis was counting on the nail polish to mask the smell of her arousal. She chose the terry cloth robe, knowing that it would not buy her much time. She washed her hands and returned to the bedroom. To her disappointment, Rick was still standing by her vanity. She had hoped to catch him peeking through the door. Alexis sat down and extended her hand. Rick got on his knees and looked at her fingernails.

"I'm sorry, forgot you need to sit down. There is a stool in the bathroom, can you grab it?" She asked.

Rick stepped into the bathroom. Like the bedroom it was not extravagant with one exception. The shower enclosure was huge. It took up the entire back side of the room. It was a large whirlpool tub with a shower head in the wall at each end. It was enclosed behind two large sliding glass doors, and the entire back wall was a window to the back yard. The top of the shower was a huge skylight. If the bedroom felt like a deck, the shower was like standing in the back yard. Next to the double sink was the stool Alexis had mentioned. Rick took one more look at the tub, then grabbed the stool and went back to the bedroom.

"Pardon me for asking," Rick said, "but don't you feel exposed in that shower?"

"The glass is one way, you can't see in. It does take some getting used to. Now anything else makes me claustrophobic," Alexis said has she opened the massage oil and held it under her nose. She set the open bottle on the vanity and extended her hand to him.

Rick worked quickly and efficiently, sparing her the explanation of how trimming her fingernails was like removing flash from model airplane parts, or how the nail polish was a lot like the paint he used on model rockets. Instead he made small talk as best he could.

"You do some work for Nancy White, don't you?" Alexis asked.

"Yes, I have been working for her for about a year now."

"Do you do her nails?", Alexis queried.

"No," Rick replied, "I do some babysitting, clean the pool and..." Rick paused. He could not think of a description of yard work that did not sound like a sexual innuendo. Mow the grass, trim the bushes, landscaping, they all seemed to have a double meaning now.

"And botanical maintenance," he concluded.

"What is that last one?" Alexis inquired.

"It is a fancy way of saying I push a lawnmower around her yard. Not a glorious job, but it beats flipping burgers in hot kitchen all day."

"I imagine you are over there a lot babysitting, she seems to have an active social life," Alexis said casually.

"I guess so; she has some late meetings too. I can't complain, she has a nice house and Jake is a great kid," Rick replied, wondering what Alexis was getting at. Maybe she knew as much about Nancy as Nancy knew about her.

Alex smiled. Rick's answers were just what she had hoped for. She was pretty certain Nancy had slept with Rick. If she had not it was a pretty impressive display of self control. He was an attractive young man, and he was at her house a lot. The sight of him shirtless by the pool would be quite a temptation. The fact that Rick had gone to great lengths to avoid even hinting about a relationship with Nancy was exactly the kind of discretion Alexis was looking for. Rick had already started on her other hand. The first one looked perfect. She changed the topic to the weather as he worked diligently at his task.

Alexis squirmed as Rick caressed her hand. For such thick fingers he had a very delicate touch. She imagined how his fingers would feel inside her pussy. She longed to feel the same delicate caresses on her clit. She felt herself getting wetter and hotter as Rick wiped the old nail polish off. He squeezed her fingertips tightly as he cleaned her. Alexis's nipples ached, she wanted him to squeeze them the same way. Rick laid his fingers on the back of her hand and pressed his thumb into her palm. It was all she could do to not leap out of her chair and pin him to the ground. Alexis pictured Rick laid out beneath her, helpless as she demanded he give her his cock. Alexis let out a quiet moan.

Rick finished with her other hand. He was surprised how fast it had gone. Her nails were in very good shape. He barely had to polish them at all. Mostly he just striped off the old color and applied the new polish. Rick rolled the stool back and picked up one of her feet; humming to himself... He let her heel rest in his lap as he poured some oil in his hand. Rick spread the oil over her foot and began to massage her heel. When he lifted her foot he caught a glance of her panties and the large damp spot in the center. Rick felt his cock twitch. Staying focused on her feet was going to be a challenge.

"There is the matter of your compensation," Alexis said.

"Don't worry about it, first one is free," Rick replied.

"I insist, I was hoping for the same deal you gave Courtenay," she said with a seductive grin. She watched as Rick's face turned red.

"I, uh, I..." he stammered.

"She did not say a thing about it. I got home while you two were still, uh, settling accounts. I went back out to the car and got myself off. I hope that does not make you think I am twisted," she said demurely.

"You are not mad?"

"I was eighteen once Rick. I know what it is like. What can I say, the apple does not fall far from the tree," Alexis said as she untied the belt to her robe and let it fall open.

Alexis watched Rick. He stopped massaging her foot and his mouth dropped open. His look of shock excited her. That he and Courtenay had fucked was not a surprise. Alexis had found enough empty condom wrappers to know that Courtenay was no virgin. Based on what she had heard that afternoon, Rick wasn't either.

"So, what did you get as your compensation?" She asked.

"Titfuck and a blowjob, and I went down on her to make things even," Rick replied, still a bit stunned.

"Did she swallow your cum or let you spray it on her tits?"

"Uh, swallowed," Rick stammered, still sounding a little shocked that he was having this conversation.

"I won't do that today. I want every bit of your cum in my pussy. Now, do I pay in advance?" she said standing up and shedding her robe.

"If you want to," Rick replied incredulously.

"Oh, I do, I really do. Now stand up," she purred, dropping to her knees and unbuttoning Rick's shorts.

Rick stood motionless as he watched Alexis pull his shorts and underwear down his legs. She cupped her breasts and lifted them high on her chest. Then she wrapped them around the head of his engorged cock. Gravity pulled them down onto the shaft of his dick as she put her hands on his ass and pulled their bodies together. He could feel her nipples pressing into his flesh.

"Fuck my tits Rick. Please fuck my tits," she moaned.

Rick complied, thrusting his hips back and forth. The soft flesh of her breasts moved with his dick. He looked down and could see a shiny streak in her cleavage where his precum had spread. After a minute or two she let go of his ass and pulled away from him. Then Alexis lowered her head and took his cock into her mouth. All Rick could see was the back of her head bobbing up and down. He knew if he saw her lips stretched around his erection he would fill her mouth with his cum. Just the feeling of her tongue swirling around his erection was pushing him toward orgasm. When he felt he was near the point of no return he gently pushed her away.

"I can't take anymore, that feels too good. Are you ready for me to give you some change?"

"No, I think you have a little more work to do before I can decide if I overpaid." She said as she sat down and put her foot in Rick's lap. She stroked his cock with her toe. It was going to be difficult to let him finish the makeover. She ached to feel him in her pussy.

Rick focused on the task at hand. He caressed her foot for a few moments and then began the pedicure. He poured some more oil into his and, then grasped her foot. Rick pressed his thumbs into the arch. He turned her foot to provide a better view of her soaking wet underwear. With both hands he squeezed and stroked her foot, then tugged on each toe. Rick cupped her heel in one hand and pressed the thumb of his other hand against the ball of her foot. She was resting her hands on her breasts. Alexis's head was tipped back and her breathing was shallow and rapid. The sight of her in such an aroused state was almost unbearable. She had taken him very close to orgasm with the blowjob. He ached to release his climax. Rick set her right foot on his thigh and picked up her left foot. He deliberately spread his legs apart, causing hers to do the same. He began to caress and massage her again.

The feeling of desire and anticipation was so intense she was almost shaking. By some miracle she had not disturbed the wet polish on her fingernails when she was grabbing Rick's ass. Now the wet polish prevented her from tugging on her nipples or stroking her clit. It was perhaps the most bizarre way she had ever been restrained. Rick's 'sexquisitely' tortuous massage made her entire body tingle. Alexis slowly rotated her unencumbered foot and brushed it against Rick's cock. She felt him jump as she made contact. It was hot and hard. She imagined it between her legs and let out a low moan.

"I don't have a foot fetish or anything, but you keep that up I will," Rick said.

"Sorry, could not resist," Alexis replied, moving her foot back after seeing a few more drops of precum bubble out. Having Rick wrap her feet around his cock and cover them with cum would be interesting, but she had other plans.

Rick toweled off her feet and picked up the nail polish. It took all his discipline to focus on the task at hand. One toe at a time he applied the nail polish. Occasionally he gave into temptation and let his eyes wander up Alexis's legs. Each time he did he saw that the damp spot on her black silk panties had grown larger. Rick looked at her breasts. The brilliant red of her fingernails contrasted with the pale pink of her areola as she lightly rubbed her fingertips on her nipples. He closed his eyes and took a few deep breathes. He finished one foot and started on the other. She mewed as he brushed the polish on her toes. The combined smells of her arousal, the nail polish, and the spicy massage oil was overpowering. Rick was determined not to crack. He would not give into her siren's song.

"Do you still want me to shave your legs?" Rick asked, his voice cracking.

"My legs and then some more," she replied lustfully.

"Here or in the bathroom?" Rick asked.

"Let's do my legs in the tub," she answered.

Rick followed her into the master bath. He briefly considered bending her over the counter and ramming his cock into her dripping wet pussy, but decided to continue to play along. Rick watched her sit on the far edge of the tub. She turned on the water and it flowed from one of the shower wands. Rick sat across from her. She put her foot in his lap again. Rick smeared the shaving gel over her leg, covering every square inch of potential stubble. Then, with long gentle strokes, he slid the razor along her leg. Inch by inch he worked his way up her leg, past her knee. He finished with her thigh, holding her ankle above his head to get the back side. He shaved right to the edge of her panties, and then rinsed her leg off with the shower wand. Her swollen labia were visible through the sheer material. Rick repeated the process with her other leg.

"Still want more?" Rick asked.

"Yes, but I'm really ticklish there. We need to be somewhere you can hold me down," Alexis said as she turned off the water.

She stood and walked to the bathroom counter. Alexis retrieved a bowl and filled it with hot water. She also picked up an electric trimmer.

"Grab a stack of towels", she instructed. Rick quickly complied.

It was a short trip to the bed and Rick was right on her heels. She set the bowl on the nightstand, and then slid her panties off, revealing a neatly trimmed triangle of thick hair. She spread one of the towels on the bed.

"I want it all gone" she said, reclining on the bed.

Rick set down the razor and picked up the trimmer. It buzzed to life. He gently placed it against Alexis's skin. She giggled and jerked away from him. Rick turned off the trimmer and looked around the room for something to hold her still with. On the back of the closet door was a rack of ties. Rick retrieved four of them. He noticed a riding crop hanging from the tie rack. He grabbed it and one more tie.

tk5555
tk5555
719 Followers
12