Heather Finds the Cougar within Her

All characters in this story are over 18 years old. Be forewarned, there is a very gradual build-up but it leads to a nice climax.

Josh and Kyle became friends on the first day of high school. They had gone to different middle schools but were in the same homeroom and shared many of the same classes. They were often assigned seats close to one another which allowed them to become even closer during their developing teen years.

Josh's dad passed away when he was in middle school and was raised by his mom. Kyle's parents were still together but his dad spent a lot of time working or was out of town on business so he was hardly ever around. The boys seemed to always be together and spent much of their free time at one another's house.

Seeing that Josh was being raised by a single mom, he often helped his mom in the kitchen when she was preparing meals. Sometimes when he was at Kyle's house at dinner time, it wasn't unusual for him to drift from the TV and help Heather in the kitchen too. He liked helping out and he had some great conversations with Kyle's mom. She appreciated the help and enjoyed Josh's company.

Whenever Josh was visiting Kyle, he always made sure to say hello to Kyle's mom and see how she was doing. He knew from their previous conversations that she was frustrated that Kyle's dad was never around but she seemed to deal with it as best she could. Heather liked the simple gesture of a polite young man asking how her day was going.

Over time, Heather and Josh became friends too, not that they spent that much time together but because she was his best friend's mom, they saw a lot of each other. She would often drive them to and from parties or the movies. It was almost like she was a second mom to Josh.

Once the boys graduated from high school, Josh didn't see Heather as much. Kyle went to a college out of town while Josh stayed local to save on the cost of his education. After Kyle graduated, Josh was shocked when he heard that Heather and her husband were getting a divorce. Apparently, he had been cheating on her for a while with a younger woman. They stayed together until Kyle was out of the house before they split up.

Kyle told Josh that his mom was getting a substantial settlement in the divorce and was financially set for life. Josh couldn't understand how anyone could divorce Heather. She was an attractive older woman in her mid-40s with blonde hair and blue eyes. She carried a few extra pounds, especially in her hips and butt. However, she had lovely perky breasts that sagged a little.

Josh was never sexually attracted to Heather, after all, she was his best friend's mom. That began to change a little after Josh and Kyle started college. They would get together whenever Kyle was in town for a long weekend or the holidays. After the divorce, Heather started working out and lost a few pounds, a fact that didn't go unnoticed by Josh.

While he saw the change in Heather's physique, Josh still didn't look at Heather in a sexual manner. Things changed one time when Kyle was home for the summer and Josh was at their house for dinner. While helping prepare dinner, Josh took note of Heather's bouncing breasts under her tank top which indicated she wasn't wearing a bra. That fact was confirmed when after looking for something in the refrigerator, she turned around and her nipples were poking out through her top. Josh tried not to look but he was a normal young man who couldn't help but be attracted to her chest.

Heather was also wearing shorts and Josh noticed her slimmed-down ass and legs. He scolded himself for looking at his best friend's mom like that. After dinner, he was helping her clean up the kitchen and while washing some pots, Heather splashed some water on her tank top. Her wet top became transparent like she was in a wet t-shirt contest. The material clung tightly to her chest to reveal the outline of her perfectly formed breasts. Her brown areola also showed through her top. Josh was staring at Heather's tits, marveling at their beauty.

Heather was a little embarrassed but was mildly flattered that she attracted the attention of a young man. When she found out her husband was having an affair, Heather lost confidence in herself and didn't feel attractive anymore. Even though several men tried to date her after the divorce, she rebuffed their efforts. She let Josh stare at her exposed chest for several seconds before she went to change. She also noticed he was getting the beginnings of an erection which brought her some inner joy.

When she got back, both of them acted as though nothing happened. It was only an accidental exposure, but it got Heather's juices flowing a little from knowing a young man saw her breasts. From the look on his face and by the way he stared at her chest, Heather knew Josh liked what he saw. Later that night, she pulled out her trusty vibrator while thinking dirty thoughts about the events from earlier and what she would like to do with a younger man.

While alone in his room, Josh felt a touch of guilt because he couldn't get the thought of Heather's exposed tits out of his mind. He was a horny young man and stroked himself to orgasm while wondering what Kyle's mom's fleshy mounds felt like or if her ass was as firm as it appeared.

From that day forward, Heather and Josh silently looked at each other differently. Josh was turning into a handsome young man with dark hair and blue eyes. He began to work out regularly after high school and had developed a muscular body that any woman would love. His toned chest was now covered in a fine layer of manly hair. He had bulging biceps and six-pack abs. His legs and ass were just as firm.

Heather loved it when the boys began to lift weights in her garage. She would often go out there to offer them something to drink while silently marveling at Josh's toned body. Those episodes would often lead to her masturbating when she was alone in her room fantasizing about a young man ravishing her body.

Josh also noticed Heather's womanly body in greater detail. It seemed that when he was at their house, she happened to be wearing tight tops and shorts. He especially enjoyed seeing Heather wearing her figure-hugging yoga pants. Even though she still had wider hips, he loved checking out her ass in them. Sometimes when she would bend over, Josh could see Heather's panties underneath which only drove him to want to see more of her.

One time in their junior year of college, Josh and Kyle were out partying and Josh spent the night at Kyle's. They were out late and Josh had to use the bathroom in what he thought was the middle of the night. It was actually early in the morning and he planned on going back to sleep after using the facilities. He was a little hungover and walked groggily to the bathroom wearing just his boxer briefs. He also had a bit of a morning erection.

When he opened the bathroom door, he was quickly brought out of his half-sleeping state when he saw Heather standing there completely nude, drying herself after a morning shower. They were both shocked, so stunned that they both stared at one another for several seconds.

Josh's eyes were drawn to Kyle's mom's natural breasts and her hairy bush. His dick began to get more erect, a fact that Heather quickly noticed. She was busy staring between his legs which stalled her efforts to cover herself. Josh's eyes darted to her supple ass and bare legs as he became fully erect. When Josh became aware of his state of arousal, he placed his hands in front of himself to hide his erection.

He blushed and stammered, "I, I, I'm s-s-sorry. I didn't know you were in here."

Heather then covered her nude body with the towel even though the sides of her breasts and ass were still visible and replied, "Uh, that's okay. I'll be done in a minute."

Josh quickly retreated and closed the door behind him. He waited in Kyle's room until he thought Heather was done in the bathroom. However, as he returned, they passed each other in the hallway. She had her towel wrapped around her but it barely covered her ass. She smiled as she passed a blushing Josh who couldn't even look at her. However, he turned his head to check her out as she walked away.

Heather thought it was cute that Josh was so embarrassed but she got a thrill out of him seeing her naked and was especially flattered that he got a full erection after seeing her. It was a great boost to her confidence.

Later after breakfast, Heather reassured Josh by telling him, "I know that what happened earlier this morning was an accident. It happens. Don't be embarrassed. Let's both pretend it never happened."

"Thanks but I'm sorry. It won't happen again."

"Don't worry. It's okay."

While they may have agreed to pretend it never happened, neither one of them could get it out of their minds. Heather would relive it in her mind while using her vibrator and wondering what Josh's hard cock looked like, tasted like, or how it would feel in her pussy. Josh would often think of a naked Heather while jerking off or even while he was having sex with another girl. The images of that morning would be permanently embedded in their minds.

Not much happened between Heather and Josh after that day. They still admired each other from afar but neither of them acted upon their private fantasies. Besides the obvious age difference, Heather was still the mother of Josh's best friend. Nothing was ever going to happen between them.

After Heather got divorced, her friend Marge was always trying to get her to start dating again. She even tried to fix Heather up with single men but she resisted Marge's efforts. Heather was so hurt by her cheating husband, she didn't know if she could ever trust another man again.

Marge would tell her, "You don't have to marry someone, but you need to get laid. You're still young and attractive, you need to get back out there and get some action."

"I don't know, Marge. I was never one to have one-night stands."

Marge convinced Heather to try an online dating service but Heather told her, "I've tried dating a couple of guys but the guys that are out there are either damaged goods or creeps. I can't even count how many dick pics I've received."

Eventually, Marge gave up on getting her friend another male companion. She'd hint around at times but she figured she should let her friend move at her own pace.

Heather was financially secure but she wanted to do some traveling but didn't want to go alone. During Kyle's senior year, she invited him to go on a cruise of the Caribbean with her during spring break. She even told him he could invite Josh and she would pay for the entire trip. Neither young man was going to pass up this opportunity and quickly accepted her offer. The plan was for Heather to get a cabin for herself while the guys would share another.

All of them were excited for this adventure and, with Marge's encouragement, Heather bought a bikini to wear along with some sexier dresses. They were sexy without being trashy, after all, she was still traveling with her son and his friend.

Marge told her, "This is the perfect opportunity to find a guy to have some fun with. You'll be on the ship alone for a few days and you'll never see each other again. Come on, live a little."

"I don't know, Marge. I'll think about it but I can't promise anything."

"How long has it been since you've had sex and your vibrator doesn't count," Marge asked.

"It's been a while," Heather replied but too embarrassed to tell her friend it was years ago.

"Well, it's going to dry up if you don't use it. You need to get laid. Besides, you're fifty now. You can't wait too much longer."

"Gee, thanks but I get what you're saying. Let's see what happens."

Heather fully understood what her friend was saying. She hadn't had sex with a man since before her husband left. She was horny but found it difficult to put herself out there again. Maybe Marge was right. Maybe it was time to have some fun. She didn't know if she could do anything while she was with her son but he'd be off having his own fun.

Heather was surprised when Kyle even told her, "I don't know how to tell you this, Mom, but if you meet someone on the ship, I understand."

She was thinking, "Oh my gosh, even he thinks I need to get laid."

She replied, "I want you to have fun on your own too. Don't think you have to entertain me."

All three of them were excited on the day the ship set sail on their five-day cruise. The guys' heads were turning at all of the young women on board and the girls were checking them out too. They were both thinking this was going to be a great vacation.

They grabbed a quick lunch and went back to their cabins to change into their swimwear. The plan was to go to the adult-only area, soak in the hot tub, and have a drink or two. They found three lounge chairs to place their belongings and headed toward the hot tub with drinks in their hands.

Heather looked at her son and his friend wondering where the time had gone. It seemed like only yesterday that they were boys playing in the yard and almost instantly they had become young men who could legally order a drink. Josh had lost that boyish look and had become a hunk of a young man. They talked and laughed in the hot tub, totally relaxing as the ship was leaving the port.

While she was on her second drink, Heather was warm from the hot water and sat on the edge of the hot tub to cool down. She was wearing a conservative one-piece suit but Josh sat off to her side admiring her bare legs, red nail-polished toes, and thick thighs. Her suit was still damp and clung tightly to her body as her nipples pushed back against the top. The fabric was hugging her lower half as well and Josh saw a noticeable camel toe. His face was only a foot or two away from her pussy. He saw wisps of her pussy hair peeking out from the sides of her swimsuit.

Heather didn't know what Josh was looking at but she could feel his eyes on her as she sat there in an almost pose-like position. She took comfort in the fact she was drawing a young man's attention in a less-than-flattering swimsuit. She eventually rejoined them in the hot tub until it was time to get ready for dinner.

Before getting dressed, Heather paused in front of the full-length mirror in her cabin, doing a couple of twists and turns to check out her nude profile, thinking, "You know, I'm not in bad shape for a woman my age. I should be darn proud of my looks."

When Josh and Kyle came to get Heather for dinner, Josh told her, "You look beautiful tonight, Mrs. Wardman."

"Thank you, Josh, but you can call me Heather."

"Are you making a play for my mom?" Kyle jokingly asked.

"Come on, man, it's just good manners to compliment a lady."

"I was just joking, Josh."

However, Josh meant every word of his compliment as he eyed Heather in her strapless flowered knee-length sundress. It followed her slim torso and flared out at the bottom to give her a sassy look. Josh took a special liking to her bare shoulders. Even though Heather was now 50, she looked great.

The three of them had a nice sit-down dinner, enjoying the expertly prepared food and drinks. Heather was more relaxed than she had been in a while. It was nice for her to see that her son and his friend were now fine young men. For them, it was fun to have a drink with Heather as adults.

After dinner, they went to a couple of bars to continue their vacation. They were getting off to a great start and were feeling no pain when they decided to go back to their rooms. The fellas naturally slept in the next day and had a late breakfast before joining Heather in the adult-only area because the area around the outdoor pool was already filled with families. They didn't mind lounging around and enjoying more drinks after lunch.

Heather was relaxing with a good book but was stealing glances at some of the bare-chested men. However, her eyes kept drifting back to Josh and his young muscular body. He and Kyle were talking to several young ladies but the conversations seemed short-lived, much to their disappointment.

Josh was also checking out Heather's shapely legs and limited cleavage that was showing in her one-piece bathing suit. He wondered why guys weren't trying to talk to her but most of the ship was filled with couples which limited her opportunities.

During dinner that evening, Kyle wasn't eating much and said he didn't have much of an appetite while both Josh and Heather were extremely hungry. This wasn't normal for Kyle because he usually had a very healthy appetite. He didn't even want his dessert. Josh and Heather knew something was wrong. Kyle said he was tired and went back to the cabin which left Josh and Heather wondering what to do next.

Heather told Josh, "You don't have to keep me company. You're a young man, you should go have some fun with people your own age."

"I don't mind, Mrs. Wardman, I mean, Heather. I don't mind hanging out with you. You're one of my best friends anyway."

It was a great compliment from Josh and made her feel better about not interfering with his fun. They ended up exploring the ship together while stopping in various bars along the way. They had a great evening talking and drinking and getting to know one another better than they already did. It was a long day and had been doing a lot of drinking so they were both tired fairly early and decided to call it a night just after eleven.

As they approached the doors to their rooms, it was almost like a first date where you don't want the night to end but you know it's time to go. If it was a first date it probably would have ended with a tender kiss goodnight but they said their goodbyes and went to their cabins.

Kyle was sound asleep when Josh got inside and did his best not to wake his friend. Kyle never moved as Josh got ready for bed and fell asleep. When Josh woke up the next morning, Kyle was still out cold but was beginning to stir.

When Kyle finally opened his eyes, Josh asked, "How ya doing, buddy?"

"Not good. Not good at all. It must have been something I ate."

"You didn't eat too much so I doubt it's that."

Josh went to get Heather who quickly felt his forehead and said, "You need to see a doctor. You have a fever."

"I'll be fine."

"No, Kyle, we're going to go see the ship doctor."

It turns out Kyle had some type of virus that the doctor said would probably go away in twenty-four to forty-eight hours. Kyle was deeply disappointed but there was nothing he could do. The doctor recommended that he be isolated in his room so he didn't spread the virus any further. He said several other people on the ship had it too.

Josh felt fine and they decided the only option would be for Kyle to go into his mom's room and she'd share a room with Josh. It was awkward but there was nothing anyone could do. Kyle had barely unpacked so the move was easy. Housekeeping disinfected the room and Josh just had to hope he didn't catch whatever Kyle had.

Heather told Josh, "I know this is uncomfortable but we don't have any other options."

"Yeah, it's not like we're going to spend much time in the room anyway."

"We'll figure it out, Josh."

This was the first port that the ship stopped at and Heather was reluctant to leave Kyle alone but he told her, "Look, I'm probably going to sleep all day anyway so you guys should go ahead without me. I'll be fine."

Heather's instincts told her to stay back but Kyle insisted so she and Josh decided to go to a beach close to the ship. Kyle promised to text message her if he needed anything.

After switching rooms, Heather found her conservative swimsuit was still damp and didn't want to wear it again. The only other swimwear she had was the bikini Marge convinced her to buy. She wondered what Josh would think of her wearing it and had to summon all of her courage to put it on. She wore her shorts and tank top over it and they left for the beach.