Her Son's Best Friend

Gabe and his family moved next door to Teddy and his family when they both were starting kindergarten. They naturally became best friends seeing they went to school together and lived next door. They shared being the youngest in their families also. They were always together from that first day. People thought they were brothers but, in a way, they were. They would play together after school and on the weekends. It was common for them to have sleepovers at each other's houses or sleep in a tent in their yards on a pretend camping trip. They were inseparable.

If one got into trouble, chances are they were both involved. They had their friendly fights but always found their way back to one another. They played Little League on the same team with Teddy pitching and Gabe being his catcher. One was rarely seen without the other. They were inseparable.

Not only were Teddy and Gabe close, but their parents were close too. While their siblings were staggered in age, they still hung out together sometimes. The families would often get together for a barbeque or they'd order pizza together and hang out with one another. Gabe did notice that Teddy's father wasn't always around much. He was a top salesman for a pharmaceutical company before moving into management. He was often busy with clients or traveling for work. Teddy's mom, Maryanne, didn't work and stayed home to raise the family.

During high school, both boys were very athletic. Besides playing baseball, they were both on the football and basketball teams. That made them both very popular in school with not only the other athletes but with the girls too. Teddy was the better athlete and student but that never bothered Gabe.

During their junior year, the college recruits had their eye on Teddy for all three sports. He was going to have his choice of schools to attend. Gabe, on the other hand, was an average student and didn't know if he even wanted to go to college. From an early age, Gabe learned the basics of carpentry, electrical, and plumbing from his dad. Gabe liked to take things apart to see how they worked and figured out how to repair small engines with a bit of help from his dad. His experiences were steering him in another direction.

It became apparent in their senior year that the boys were probably going to be going their separate ways once they graduated high school. They mentioned it to each other but decided they would worry about it when the time came. Until then, they were going to enjoy their final year of high school.

Both boys turned eighteen shortly after New Year and had developed a bad case of senioritis, knowing they only had to endure a few more months of high school. Teddy had already committed to a major university to play baseball while Gabe decided to go to a local community college so he could figure out which trade he'd like to pursue. Meanwhile, their main goal was to have as much fun with their male and female friends as they could while they were still together.

One evening, a few of the baseball players had gathered at Teddy's house to watch a game on TV. His mom made sure they had plenty of food and soft drinks available. She would check up on them under the pretense of seeing if they wanted anything else to eat. One time after Maryanne checked on them, one of the boys, Paul, made a comment to Teddy after she left.

"Your mom is pretty hot, Teddy."

The other guys other than Gabe laughed but Teddy didn't think it was amusing.

Gabe said, "Come on, man. That's Teddy's mom you're talking about."

Paul quickly apologized but it got Gabe thinking. He never looked at Maryanne that way before but she was pretty and had nice boobs and a nice round butt. She was curvy but still had a nice body. Her blonde hair and blue eyes were only enhanced by a dynamite smile. She might have been in her mid-forties but she still looked pretty good. When Teddy wasn't in the room the other guys would talk about Maryanne's tits or ass but Gabe kept his mouth shut.

From that day forward, whenever Gabe was around his best friend's mom, he took notice of her body. If she were moving about this kitchen preparing a meal, Gabe would take note of her hanging breasts down her shirt when she leaned over or her ample butt if she was bending over. He would chastise himself for looking at her that way but he was still a horny teenager that was easily distracted by a woman's body.

The boys were out partying one Friday night and Teddy told Gabe to sleep at his house so he didn't get caught drinking by his parents. Teddy's dad was out of town and his mom went to bed early so that lessened their chances of getting caught. They came home a little drunk and passed out in Teddy's room and would probably sleep until noon.

Gabe woke up early in the morning needing to urinate. He was groggy and hung over as he shuffled off to the bathroom. As he pushed open the bathroom door, he heard the sound of a hair dryer starting and saw Teddy's mom standing there stark naked apparently after just getting out of the shower. He was stunned and stood there in shock checking out his best friend's naked mom. His eyes first focused on her C-cup breasts that sagged a bit and her prominent dark nipples. His eyes were drawn to her fluffy ass before looking at the hairy bush between her legs that hid her pussy lips.

When Maryanne took notice of her young voyeur, she let out a little scream and said, "Oh my god, Gabe. What are you trying to do, scare me to death?"

She then bent over to pick up a towel and covered herself.

"I, I, I'm so sorry, Mrs. G. I didn't know anyone was in here. I had to pee."

"The shower in our room is leaking. Maybe you could take a look at it later. You can use that one while I finish here."

"Uh, yeah sure."

Gabe was so embarrassed. He didn't want his friend's mom to think he was a pervert. It didn't help that he was starting to get an erection. He was further embarrassed when Maryanne looked down at his growing problem and grinned slightly. She was kind of proud that she gave a young man an erection. Her sex life with her husband was almost non-existent seeing he worked all the time and was rarely home. She gained a few pounds over the years and had thought she lost her sex appeal.

Maryanne was also checking out Gabe. He was an eighteen-year-old boy with a man's body. He was an athlete who worked out all the time and had well-developed arm, shoulder, and chest muscles. She took note of his rippling abs and hairy chest that she liked too. He was standing before her wearing only his tight boxer jock underwear with a decent-sized lump beginning to protrude. When he turned to leave her eyes were drawn to his taunt ass. She was chastising herself as she watched his butt cheeks alternately tighten and loosen as he walked away before she closed the door again. Her pussy was damp and she made a mental note to try to seduce her husband when she got home. Checking out her son's best friend made her realize she needed to get laid.

They passed each other in the hallway as they returned to their respective rooms. Maryanne's eyes were drawn to the front of Gabe's underwear. He lost his erection but still had a decent lump there. Gabe was afraid to look her in the eye but still blushed because he knew she was naked underneath her towel. He had to tell himself not to look at her.

Later that morning, Maryanne caught Gabe by himself and told him not to be embarrassed about what happened earlier. It was an honest mistake and no one had to know. That made him feel better but he now knew what she looked like naked. It would change how he looked at her in the future.

A few days later when their families were in the backyard having a cookout, Gabe looked differently at Maryanne's ass in her tight black leggings, recalling what her naked butt looked like. She was wearing a tank top that teased him with its show of cleavage. Her bra supported her breasts which made them that much more noticeable. The tops of her breasts jiggled when she walked.

Maryanne could feel Gabe's gaze on her at times and would turn to face him. She knew he was looking at her differently by the way his eyes would dart to look at the ground when she returned his glance. After a couple of drinks, Maryanne was feeling frisky and purposely bent at the waist to pick up a napkin she dropped in front of Gabe, giving him a view down her top at her hanging breasts, her face almost in his crotch. When she stood up, she looked him in the eye and he began to blush. She felt naughty for teasing a young man like that but it made her feel better about herself and made her panties wet. To her, it was harmless fun.

The school year was moving by quickly and once the baseball season was over, it was time for the prom and graduation. Gabe had started dating Katie, another eighteen-year-old senior, earlier in the spring and she accompanied him to the prom. She was also going away to college but she promised that they'd try to maintain a long-distance relationship while she was gone. They partied together and explored their sexuality for most of the summer, sometimes several times per day.

In the meantime, Gabe and Teddy's mom kept playing her little game of teasing him on occasion. Maryanne thought it was innocent fun seeing she wasn't exposing herself too much to Gabe. She kept it to some downblouse or quick upskirt views with some intentional bending over in front of Gabe when she was wearing shorts or leggings. She didn't want to be too blatant because she didn't want to embarrass Teddy. She figured out ways to tease Gabe where there was plausible deniability in her actions.

Everyone was shocked when shortly after graduation, Teddy's parents announced they were getting a divorce. It was something that was in the works for a while but they decided to stay together until Teddy was done with high school and was on his way to college. Gabe overheard his mom talking about it with Teddy's mom, Peg, and apparently, his dad was cheating for a while with his secretary. It was still difficult for Maryanne to divorce her husband after more than twenty years of marriage.

Maryanne and her husband had agreed on a settlement where she got the house and a very generous monthly alimony payment where she wouldn't have to work because she gave up her career to raise the family. He moved out of the house as soon as they announced their breakup.

It was a difficult time for Teddy and his mom. Gabe was there for his friend who was hurt by the sudden breakup of his family. However, they were also going to enjoy their last summer before they went their separate ways. Teddy and Gabe did their fair share of partying and making love to their girlfriends.

Meanwhile, Maryanne found comfort and support from Gabe's mom who was there for advice and a shoulder to cry on. She was understandably depressed and hurt. She felt betrayed by her husband and felt old and unwanted after being left for a younger woman. That lasted about a month and just before Teddy went off to college, Maryanne joined a gym to help her mood and to shed some pounds. Even though she wasn't fully over her divorce, she began to feel better about herself and her situation.

It was difficult for Maryanne to drop Teddy off at college because she would now be all alone in a big four-bedroom house. Even though he wasn't around much before, he would at least be there to sleep and eat. She was now all alone.

Gabe ended up in a similar situation when his girlfriend decided a long-distance relationship wasn't going to work and broke up with him. His parents were traveling and going out more often which left him alone much of the time, especially on the weekends. He was now heartbroken and mostly alone. He still had his schooling and job to help keep his mind off of his troubles but he was still deeply hurting inside.

Now that Maryanne was responsible for the entire upkeep of her home, Gabe's mom made sure that he was available to help her whenever she needed something. If there was a minor home repair or chore that needed to be done, Gabe was there to help his now-divorced neighbor. His mom didn't have to tell him to help out, he would have done it anyway. He felt terrible for Maryanne and knew Teddy would be there for his mom if she needed help. It was the least he could do to help a friend and someone who was like a second mom to him.

Gabe was at Maryanne's house several times a week helping her with anything that needed to be done. He began to notice a transformation in her body also. Maryanne was working out with a personal trainer at the gym and before long, she had slimmed down and her body became more firm. Being in better physical condition helped Mayranne's confidence and she was beginning to wear clothing that better accentuated her figure, a fact not lost on Gabe.

He had seen Maryanne naked a few months ago and couldn't help but wonder what her body looked like now. He tried to keep his thoughts under control but that proved impossible for a horny teenage boy who wasn't getting laid. Gabe found himself staring more closely at Maryanne's ass in her workout clothing. Even though she had lost weight, it was still round and meaty. She was also more apt to wear sports bras or tight tank tops around the house. Gabe became very fond of Maryanne's breasts.

The images of previously seeing Maryanne naked and her new trim body became fodder for Gabes' masturbatory fantasies. Late at night or when he was alone, he often found himself jerking off at the thought of what he would like to do to his best friend's mom. He wondered what it would be like to fondle and suck on her big breasts or to grab hold of her luscious ass. That naturally led to thinking about what it would be like to have her lips wrapped around his dick or to fuck a horny older woman.

Gabe wasn't the only one having sexual fantasies. Maryanne was staring more intently at Gabe's youthful body recalling seeing the lump in his underwear that one fateful morning. He was a tall young man with strong arms and broad shoulders. He would often remove his shirt when helping in the garden. She would often desire to run her hands over his big muscles and hairy chest. Maryanne desperately wanted to sink her hands into his firm muscular buttocks. She would also close her eyes at night while running her vibrator over her naked body fantasizing about playing with her neighbor's youthful body. It had been almost a year since she had sex and her pussy was itching for attention. She wondered what Gabe's dick tasted like and what it would feel like to get fucked by a horny young Adonis.

Both of them knew they could never act upon their fantasies. They had known each other too long and both felt guilty about what was going through their minds when they were together. There was no way Gabe could fuck his best friend's mom even if she wanted him to. That would simply be wrong and disrespectful. If they got caught, it would ruin their friendship forever.

It was the same for Maryanne. Gabe was her son's best friend and his mom was her best friend. It was so taboo to even think about what she wanted to do with him. To her, it was nothing more than a sinful fantasy that she never planned to act upon. There was nothing wrong with sexually desiring a handsome physically fit young man but to take it any further would be morally wrong. They were Maryanne's private impure thoughts and she rationalized them by thinking that men look at young women like that all the time so it was okay for her to do the same.

That didn't stop Maryanne from continuing to try to draw appreciative glances from Gabe by discreetly showing off her body to him. She began to wear shorter, tighter shorts when he was around. She began to go braless more often knowing he couldn't keep his eyes off her protruding nipples or from trying to sneak a peek down her shirt. She would feel naughty by teasing him and would satisfy herself later with her fingers and vibrator.

Gabe would also end up jerking off at the sight of Maryanne's nipples or most of her breasts. There were times when he'd be able to see her bikini underwear through the stretched fabric of her shorts when she bent over in front of him. He wondered if she was teasing him on purpose but quickly dismissed those thoughts as being ridiculous. That didn't stop him from wanting to grab her ass or desiring to bend her over and fuck her hard. That's exactly what he thought about doing when he would jerk off at night.

One time when Gabe was helping Maryanne with some gardening, she was wearing a bikini top under the guise of wanting to get a suntan. However, the top hung loose on her and when she was leaning over pulling weeds, Gabe could see her entire breasts down to her nipples.

He thought, "She must know what she's doing. There is no way she doesn't know she's showing off her tits to me."

It was impossible for Gabe to keep his dick under control. He kept getting an erection and had to move to another part of the garden to keep Maryanne from noticing his predicament and to avoid embarrassment. She must have seen the tent building in his shorts at least one time. He was standing right in front of her looking down her top as his dick began to grow. Her face was practically in his crotch as she looked at it before looking up at him with a knowing grin. He walked away to avoid further embarrassment.

Maryanne's desire for her teenage neighbor was only getting worse after seeing him getting an erection. She realized she was teasing herself too. Knowing there was a young erect cock so close to her made her want to pull his shorts down, stuff it in her mouth and suck it before riding him. The more she teased Gabe, the more she considered acting upon her carnal desires. She told herself she had to maintain control. She could never, ever let it happen.

Gabe wondered how long he could hold out from doing or saying something to Maryanne. He suspected Maryanne might be teasing him on purpose but he quickly dismissed that idea as being ludicrous. There is no way his friend's mom is putting the moves on him. Even though his desire to fuck her kept growing, he thought he was wishful thinking that she wanted to fuck him too. He figured he'd have to leave town if he tried to fuck her and she laughed at him for his efforts. It would be worse if she told his mom. He'd never live it down. That didn't deter him from jerking off at the prospect of fucking his older neighbor.

Maryanne knew at some point she needed to start dating again but after being married for so long, it was difficult to even consider going on a date. She was set in her ways and was still hurting from her divorce and was afraid of being hurt again. Gabe's mom suggested a couple of single men but Maryanne wasn't interested. She was still horny and considered finding a guy for a one-night stand but found that difficult to consider also. She joined an online dating site and that only scared her more. She was horrified by the number of dick pics she received and wondered if there were any sane single men out there.

Gabe was going through a similar problem. He was having trouble getting over his broken heart. He did go on a couple of dates and had sex with some of them but it wasn't the same as being with Katie. He thought he loved her but she didn't feel the same. The thought of her dating other guys, or even worse, having sex with them, kept his heart from healing.

He found himself spending more and more time at Maryanne's house, especially when his parents weren't home. Gabe appreciated her company and guidance when it came to school, a career, and even his love life. She encouraged him to start dating again even though she had a secret crush on her teenage neighbor.

Maryanne was supportive of Gabe and told him, "You'll find the right girl someday. It's only a matter of time. You're a handsome young man. You have to put yourself out there and take a risk."