His Daughter's Best Friend

Story Info
A man's wish to fuck a young woman finally comes true.
12.5k words
4.69
94.7k
123
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
Jay142
Jay142
3,605 Followers

Ted was living the perfect life. He had a great job, a wonderful wife, Anne, and two wonderful children. Ted Jr. is their firstborn and his daughter, Charlotte, was born two years later. He was living the dream with a four-bedroom home in the suburbs, going to school sporting events and dance recitals of their children. His wife was the president of the PTA.

Ted Jr. went away to college studying to be an engineer and Charlotte was a straight-A student who played soccer and volleyball. He was sure their children got into trouble that they never found out about but for the most part, the things they caught them at were pretty mild compared to what Ted was doing at their age. A parent will always worry about their kids but his wife and he were fortunate to have a fairly stress-free life compared to their friends.

Anne and Ted had their ups and downs like any married couple. They struggled financially when they were first married, went through the deaths of their parents, and made it through job changes. They had a decent sex life that wasn't as frequent as when they were younger but that's pretty normal as they gracefully aged together. Sex got even less frequent as Anne started to go through menopause.

Anne tried to keep their sex life going but Ted could tell she wasn't into it. She'd give his dick some obligatory licks before he stuck it in her, then it seemed like she couldn't wait until it was over. It got even worse when Anne couldn't stand his snoring anymore and he moved into the guest bedroom to keep from arguing. By that time, Ted was jerking off more often than having sex with his wife so at least he didn't have to sneak off to do it anymore.

Just about the time their sex life began to go downhill quickly, their daughter and her best friend, Olivia, turned eighteen. It was one of those moments in life that makes a parent feel older, especially when Charlotte was talking about moving out of the house and going away to college. Anne and Ted discussed downsizing and selling their house to move into a condo when she graduated but they weren't ready to leave the home where they raised a family.

In those final months before they became empty nesters, Ted began to look at Charlotte's friend differently. Both Charlotte and Olivia seemed to suddenly turn from girls into young ladies. In doing so, so did their bodies. Ted didn't know if it was because he had blue balls more often, the seemingly sudden development of their bodies, or a combination of both but damn, Olivia was a gorgeous young lady. She wasn't the awkward teenager with braces anymore. She had a warm, welcoming smile, full lips, and baby-blue eyes.

It began one evening when Olivia and Charlotte were kicking around a soccer ball in the yard. They were wearing tight spandex shorts and sports bras. As Ted peered out the kitchen window while getting a glass of water, his eyes became fixed on Olivia's strawberry blonde hair in a ponytail. She lost her baby fat and now had a trim hourglass figure with a tight round butt. Her shorts were so tight they fit snugly between her ass cheeks. While her sports bra tightly constrained her B-cup breasts, it highlighted her slender hourglass figure, well-defined muscles in her arms, and toned abs. Ted was pleasantly surprised by how fit Oliva was.

Olivia was enjoying the new-found attention she was receiving from the opposite sex from the development of her young body. She still thought her boobs were too small and her butt too big but she noticed guys checking her out more often. The more revealing her clothing became, the more attention she received. Once a young lady discovers boys are finding her attractive, they seem to want to show off their developing body.

Years ago, Anne and Ted had an inground pool installed with a hot tub. The intention was to have a place in their yard where they could enjoy the summers but also act as a place where the kids could entertain their friends. It was easier to keep an eye on them when they were socializing at home. Now that Ted Jr. was out of the house, the pool became the central gathering place for Charlotte and her friends. It wasn't unusual for Ted and Anne to come home from work to find several of Charlotte's friends there.

Now that Olivia and Charlotte were eighteen, they began to wear skimpier bikinis. Ted told his wife he thought Charlotte's swimsuit was more revealing than he liked but Anne told him that's what girls were wearing now and that he was old-fashioned. He was on the losing end of that discussion.

If Charlotte's bikini was revealing, Olivia's exposed more of her young tender body than his daughter's. She might as well have been wearing a thong because it barely covered any of her delectable tight ass. Even more of her cheeks were revealed after swimming or moving around when the bottoms would become wedged between that luscious derriere. Ted felt a touch guilty for looking at Olivia in that way but she had a nice ass. She thought Ted may have been checking her out so she deliberately wouldn't pull her bikini bottoms from between her cheeks in hopes he was looking.

Her bikini top barely covered her nipples, leaving most of her tantalizing mounds in view. Her breasts are nice but on the smallish side so when Olivia would lean over, the top would sag just enough to give Ted a view of her entire breast, nipples and all. The first time it happened she didn't know what Ted was looking at until she looked down herself. Her first instinct was to cover herself but she found she liked having him looking at her.

Olivia purposely exposed her breasts to Ted a couple of more times and her pussy got wetter each time. Each time he got a glimpse of those beauties, he wanted to touch them and take her nipples between his lips. His eyes would suddenly dart the other way when she looked up at him. She liked the fact that she could attract the attention of an older, mature, married man.

Ted felt like a dirty old man at times but he wrote it off as harmless looking. He had absolutely no intention of acting upon his manly desires. He found himself thinking of Olivia's ripe body when he masturbated while alone in his room at night. He chastised himself for looking at his daughter's friend that way but rationalized it by thinking that other dads were probably checking out his daughter too.

Not only did Olivia look great in a bikini or her spandex sportswear, but she was pretty hot in a pair of tight jeans and a tank top too. She has this perfect heart-shaped ass that shakes when she walks. She likes to wear low-rise jeans and her whale tail was often visible. Ted's eyes would immediately be drawn to the exposed strings of her thong and knew the color of her panties and imagined what they must look like on her. Sometimes he'd even catch a glimpse of some ass cleavage, that little bit of the crack of her ass too.

Charlotte and Olivia had boyfriends their age and Ted knew from conversations he overheard and from his wife that they were sexually active. He would look at Olivia at times when he saw her with her boyfriend and imagine what it would be like to have those precious lips wrapped around his dick or to fuck that tight teen pussy of hers. Ted thought it was a shame to waste her good pussy on an inexperienced lover.

The night of their prom, a few of the girls got ready at Ted and Anne's house. Anne was fighting back the tears watching their daughter looking like a grown-up woman, much older than her eighteen years. Ted thought her dress showed too much of her cleavage and had a slit up one leg. Her hair and makeup were done professionally. He knew there was no way her date was going to keep his hands off of her.

Olivia's dress was an even more daring gown that was more low-cut than Charlotte's with a slit up her left leg to her hip. When she walked, Ted caught a glimpse of her black thong and garter underneath. She looked like she was in her twenties and he envied her date.

From what Anne had heard from other parents, Olvia and Charlotte went to a party after the prom where people were smoking weed and alcohol was freely available. It bothered Ted a little but it wasn't anything he didn't do at their age. There was no doubt in his mind that they both got laid that night too. Ted wanted to think his daughter and her friend were still innocent but the reality was that they were young adults now.

As the weather got warmer, Olivia became a fixture around the house as the girls got good use out of the swimming pool and hot tub. Charlotte had other friends but they weren't as attractive as Olivia. Ted's mood seemed to perk up when Olivia was around and he realized he had developed a crush on his daughter's friend. It was a harmless attraction but she was a beautiful young woman and quite friendly. She always took the time to talk to Anne and Ted and thank them for their hospitality. From what Charlotte told her parents, Olivia's parents got divorced years ago and her mom wasn't around much so they became a substitute family for her.

In return, Olivia had developed a crush on Ted. He kept himself in decent shape but had a little beer belly. He has light brown hair with wisps of gray and dark brown eyes. She always greeted Ted with a charming smile that would show her dimples. Now that she knew he was admiring her young body, Olivia made sure to dress in a more alluring manner when she knew Ted was going to be around the house.

Ted was a night owl and unlike most people, only needed a few hours of sleep. His wife and daughter, on the other hand, go to bed much earlier. He loves the peace and quiet at night when everyone is asleep. He can be alone with his thoughts while sipping a beer. Sometimes when Olivia was spending the night, she would come down and watch TV with Ted.

One night Ted was watching a baseball game and drinking a beer, when he heard Olivia ask, "Whatcha watching?"

He turned to see Olivia standing in the doorway wearing a white satin button-down pajama top with matching shorts. Her nipples were poking through the thin fabric like they were begging him to notice.

"Oh, just a ballgame," Ted replied.

"Do you mind if I join you? I don't want to go to sleep this early."

"That's fine. I could use the company. Why don't you get yourself something to drink?"

"Okay, Mr. K, I'll be right back.

"Grab me another beer while you're in there."

Olivia returned with two beers but he didn't say anything seeing he knew she and Charlotte were no strangers to alcohol. She handed him a beer and sat at the other end of the sofa with hers.

Ted began to sip his beer as Olivia made herself comfortable. He almost choked on his beer when Olivia crossed one leg on the sofa with one leg on the floor. Her pajama shorts were loose around the legs affording Ted an up-short view of a cleanly shaven pussy.

As he was struggling for air, Olivia asked, "Are you okay, Mr. K?"

Ted managed to say, "Yeah, I'm fine. It just went down the wrong way."

He tried his best not to stare between Olivia's legs but her sweet teen pussy was there for the viewing. Ted would try to watch the game but kept glancing over at Olivia who seemed oblivious to what he was looking at. His deviant mind couldn't help but wonder what her pussy tasted like or how it would feel wrapped around his dick. It then hit him that she was completely naked underneath her pajamas. Unfortunately, she brought both of her legs onto the sofa and his view ended.

When the ballgame was over, they took their empty beer cans into the kitchen and said their goodnights. Olivia looked up at Ted with her baby-blue eyes. It was like she wanted to say something but didn't. He followed her up the stairs to their rooms, her picture-perfect ass twitching in his face. It took all of Ted's willpower not to reach out and touch her butt. When they got to the top of the stairs, Olivia looked at him like they had just ended a date, almost like you don't know if you should ask for a goodnight kiss or not. She then gave Ted a big hug and they left to go to their rooms.

Ted had a great jerk-off session that night thinking about what he'd like to do with his daughter's friend. It was a harmless fantasy that he knew would never happen. A man could dream anyway. He fantasized about eating that sweet honeypot and then sliding his dick into that tender teen pussy while looking into her soft blue eyes. Ted wondered what it would be like to have her riding him while he played with her perky little titties. He desperately wanted to suck on her nipples. Ted was able to let his fantasies go wild knowing he had a better chance of winning the lottery than having his dream come true.

The closer graduation day became, the more Olivia seemed to be at Ted and Anne's house. It got to the point they wondered where she was when she wasn't there. Not only was Olivia sleeping at their house on the weekends but also several nights during the week. She had taken over Junior's room to the point where everyone called it, "Olivia's room." Anne and Ted were becoming pseudo-parents to Olivia, not that they minded at all.

That meant Ted got to see Olivia around the pool more often and they spent more evenings watching TV together late at night. Their nights alone allowed them to talk and get to know each other on a deeper level. They were developing a bond because Ted was talking to Olivia as an adult, not a child. She was more accepting of his advice because he wasn't preaching to or lecturing her. Ted guided Olivia on what to expect in college, was a soothing influence when she talked about her family life, and advised her on dealing with men.

"I'm tired of dating guys my own age. They're so immature."

"I've got news for you, it doesn't get much better," Ted said with a laugh. "Just ask Anne."

Olivia laughed and replied, "So you're saying that men are basically hopeless."

"Yeah, pretty much."

"That's what I like about you, Mr. K. You know how to make me laugh."

"In all seriousness, Olivia, when you're in college, you'll be around a lot more guys. We're not all that bad."

"I hope you're right."

One night, Ted and Olivia were having a couple of beers in the hot tub and she was expressing some frustration with her boyfriend.

"Paul can be such a jerk sometimes. All he thinks about is one thing if you know what I mean."

Ted smiled and replied, "Yeah, that's what teenage boys are like. That's why dads don't like it when they see their daughters starting to date. We were young once and know what they're after."

Olivia laughed, "Don't they understand that we want something more than that? Don't get me wrong, girls like sex too but it's not all we think about."

"It takes guys a while to figure that out. Some learn faster than others."

"I think I need to find one like that."

Olivia got out of the hot tub and was sitting on the side to cool off. Ted was fondly admiring the young teen's body as she sat in an almost pinup-like pose. She had such nice slender legs with some muscle definition to them from playing sports. Her stomach was taut and the mounds of her breasts were pushing out of the top of her bikini. He dreamed of what he would do to her if she were older and he wasn't married.

Ted was caught off guard when Olivia asked him, "Do you think I'm pretty, Mr. K?"

"What? Of course, I do. You're a beautiful young lady. Why do you ask?"

"I don't know. Sometimes I think my boobs are too small and my butt is too big."

Ted had a couple of beers in him by then and replied, "You've got a great body, Olivia, trust me. Your boobs are perfect and you've got a nice ass."

He immediately regretted being that outspoken. He wished he would have been less specific. He basically admitted he had been checking her out.

"Do you really think so? I mean, you aren't saying that just to be nice, are you?"

"No Olivia, you are a gorgeous young woman."

"Thanks, Mr. K. You're not so bad yourself."

Olivia kind of blushed a little and looked down to avoid eye contact. Ted wondered if they both just admitted to having a crush on one another. No one had paid him a compliment like that in years.

They decided to go for a quick dip in the pool to cool off before heading inside. When Olivia stood up, she adjusted the front of her bikini bottoms. Ted was standing lower inside the hot tub and his face was directly in front of her crotch. He almost gasped for air because Olivia's wet suit was now pulled snuggly into her crotch to show a perfect camel toe. He recalled getting glimpses of her tender teen pussy before and it was now inches from his face covered only by the thin fabric of her bikini bottoms.

What Ted didn't know is that Olivia knew exactly what she was doing and she was deliberately trying to get his attention. He followed her to the pool steps watching her twitching ass the entire time. He desperately wanted to know what her tight cheeks felt like but knew it was just a wish.

Before Olivia stepped into the pool she looked back at Ted and noticed his eyes staring at her butt. She was proud to see a lump developing in his swim trunks. He wasn't only being polite when he told her what a nice body she had. His growing erection confirmed it. Thankfully for Ted, the cool water also helped to cool his growing desires.

Just before they decided to call it a night, Olivia went down the slide. When her body hit the water, the top of her bikini went up above her breasts. When she stood up, her tits were exposed. Ted looked at her with his eyes and mouth wide open in awe of her perky breasts and hard nipples. He had seen glimpses of her breasts but never completely bare before.

Olivia let Ted get a good look at her state of partial undress before pulling her top back into place and saying, "How embarrassing. I'm sorry."

"No, that's okay. No need to be embarrassed."

As they dried themselves off, Ted watched as Olivia bent and turned, her bikini bottoms firmly wedged between her flawless ass cheeks. She made no effort to pull them out either. She could feel Ted's eyes on her ass as he followed her into the house and up the stairs to their rooms. Not only did he want to touch her but he wanted to nibble on the meaty flesh dancing before him. Once again, they stood looking into each other's eyes before they hugged and parted.

Ted's manly desires wanted to invite Olivia into his room. He wanted to fuck the teasing teen but he knew he couldn't. His eyes scanned her delicious body from her strawberry blonde hair to her lovely breasts, down to her camel toe, luscious legs, and back again. Olivia was hoping for a request to join him but knew that it wouldn't happen. She would have willingly gone into his room if only he had asked. They looked at one another for a few moments before parting with Ted watching her ass until she got to her room. She paused at the door giving him one more chance for Ted to invite her to join him before going into their respective rooms alone.

Once in his room, Ted congratulated himself on his self-control which took all of his willpower to manage. That didn't stop him from very explicitly thinking about what he would like to do with Olivia while he jerked off once again. He was fantasizing what it would be like to touch her succulent body, and lick and kiss her from her head down to her toes when he heard muffled moans through the wall of Olivia's room. It sounded like she was masturbating too. That only drove his thoughts to wonder further how those sweet lips would feel wrapped around his hard dick and how tight her juicy pussy would feel as he fucked her. He thought about what it would be like to fuck that tight ass of hers. His moans grew louder as his orgasm was approaching, matching the sounds coming through the wall.

While Olivia was twiddling her clit and fingering herself, she desperately wanted to know what it would be like to make love with an older, more mature man. The sounds coming from his room confirmed that Ted was excited by her and her body which only made him more attractive to her. She wanted to please him and knew that he wanted her too. Olivia wanted to feel Ted inside her and that she was a better lover than his wife. She momentarily considered going into his room so he wouldn't have to satisfy himself but didn't have the courage to follow through with her yearnings for Ted.

Jay142
Jay142
3,605 Followers