The Widower And The Waitress

Brandi is a very petite woman, standing just over five feet tall and barely weighing one hundred pounds. Her slender body frame has given her thin legs, barely there hips, and butt that can hardly hold up a pair of jeans. She doesn't have small breasts, she hardly has any at all. She is flat chested with little bumps from her nipples.

Brandi struggled with body image issues her entire life. Her mom was a single parent who struggled to put food on the table and a roof over their heads. She didn't have time to help Brandi deal with her issues, especially when she was a teenager.

It was especially difficult in high school when all of the other girls were going through puberty and she kept waiting for that moment when she would at least get some kind of womanly figure. Her mom kept telling her that her time would come, but now that she was in her early twenties, Brandi realized that time was never going to arrive. She begrudgingly learned to accept her fate that she would never have much of a curvy figure.

Her body image issues were already there, but were only made worse by the cruelty of classmates in school, especially the boys who would tell her she was flat as a board. She would see them fawn over the other girls who were more developed than she would ever be.

The thing that really hurt was when people mistook Brandi for being a boy. It hurt more because it was unintentional and couldn't be written off as someone being an asshole. Brandi kept her hair a little longer and tried to dress more feminine to keep those comments to a minimum.

Even though Brandi wasn't the most popular girl in school, she still managed to lose her virginity the night of the Senior Prom after she turned eighteen. A not so popular boy asked her to go with him and even though she thought the prom was overhyped, she accepted his invitation. Danny was a little on the heavy side, wore glasses, and was a touch nerdy, but she let him take her to a popular lover's lane after the prom.

All of the other girls at school were talking about sex and she was more curious than attracted to Danny. Needless to say, her first experience with sex wasn't the greatest. They were both virgins and didn't quite know what they were doing. No one had ever seen her naked before and she was afraid to expose herself but her flat chest didn't matter to him. It was her pussy that he wanted. It hurt a little when he entered her and he didn't last that long, but they were no longer virgins.

They did it a second time later that night at a party. It was much better that time. Brandi sucked his dick a little and he lasted a lot longer. She decided it felt pretty good even though she didn't orgasm. She had heard her classmates talking about giving blowjobs and she wanted to try it. It was strange staring down at a hard cock and she almost changed her mind. She figured it was now or never and closed her eyes and took him into her mouth.

After sucking Danny's cock for a few minutes, she decided she liked it, especially when she heard his soft moans. She was more turned on when he slid his dick into her pussy. Having sex in a spare bedroom was much better than the back seat of a car.

The thing about losing your virginity is that you aren't as reluctant to have sex anymore. Everyone at the party knew what she and Danny were doing in the bedroom and Danny was bragging to all his friends, so it was no secret she was no longer a virgin. Once guys found out that she'd be willing to have sex, the more dates she got. Brandi still wasn't very popular but at least she was occasionally getting asked out. Danny wanted to keep dating but she wasn't interested. He became her booty call when she got horny, though, especially after he started eating her pussy. The prospect of a good orgasm increased his chances of getting a call from her.

Brandi wouldn't always have sex with a date; she didn't want to get a reputation as a slut. If she was horny, the chances of them getting lucky increased. Sometimes, if she didn't let them fuck her, she'd give them a handjob or a blow job. A friend of hers told her that she didn't want to get a reputation as being a cock tease, so she should take care of them somehow. If some guy made a rude comment about the size of her breasts or the lack thereof, he'd have to take care of his hard on himself.

The first time Brandi tasted cum, it was totally by accident. She was sucking her date's dick at the lover's lane and there was no warning that he was about to cum. There were no moans or groans; he held her head in his lap and it just came out. Most of the time, she'd blow a guy until he was about to cum and masturbate him to finish him off. This time, there was a wad of cum in her mouth before she had a chance to lift her head. He had a firm grip on her head, so she couldn't have lifted it anyway.

That first wad of cum was quickly followed by a second and a third. By that time, she discerned that it didn't taste half bad. However, he came so much and she wasn't prepared for it, so she had trouble swallowing it all. Some of his cum dripped out of her mouth and down her chin. From that day forward, she always swallowed when giving a guy a blow job.

Brandi had a part-time job at a department store as a cashier while she was in school, but after she graduated, her mom made it clear it was time for her to fend for herself. She was a single mom who did her best raising Brandi. They were always on the verge of losing their apartment and would often have to deal with one of their utilities being shut off. Brandi didn't like her mom's boyfriend anyway, and he also let her know she wasn't welcome if he was going to help support her mom.

Brandi waited until she turned nineteen and got an apartment with a couple of friends, Julie and Patti. She was working full time at the department store by then. It wasn't a great job, but it helped pay the bills. When her hours got cut at the store, Julie helped her get a job filling in at a sports bar she worked at. Brandi had never been a waitress before, and it showed. However, she was a quick learner and started to pick up more hours at the bar. It got to the point where she was making more money in tips than she was earning at the store.

Little did Brandi know, but she was about to meet an older man who would change her life, and she would gain a lifelong friend. But more on that later. Life has a way of throwing you a curveball when you least expect it.

After Harry's wife Dee passed away after a long illness, he found himself alone for the first time in almost thirty years. He was in his mid-50s and financially secure from her life insurance policy, wise real estate investments, a good paying job, a healthy stock portfolio, and some inheritance.

If there is one thing that Dee's passing taught Harry, it's that life is short and unpredictable, so he retired early. After grieving for several months, he decided to enjoy life to its fullest because it could be gone in a flash. He traveled, bought himself the sports car he always dreamed of, bought a nice set of golf clubs, and did whatever whim came to him.

Harry and Dee had two children who lived out of state who he saw several times a year, but he was single and alone. He had no interest in dating, but that didn't stop his friends from trying to fix him up with single female friends of theirs.

One friend, John, told him, "It's time for you to get laid, Harry. I know it must have been a while."

"I'm fine, John. I'm not looking for anybody to complicate my life right now."

That didn't stop John's wife from trying to find Harry a female companion. If he went to their house for dinner, he would often find that a female friend of theirs was also invited. They finally got the hint that he wasn't interested in them trying to play matchmaker.

Harry hadn't had sex since before his wife got sick, which was a few years ago. He satisfied his needs through masturbation. He knew he needed to get laid but wasn't excited about the prospect of dating again at his age. He considered hiring an escort service but that didn't appeal to him either.

Harry liked to socialize with his friends. He and John would often meet up with a couple of other friends, Rod and Mike, to play a round of golf or watch a ball game at a local sports bar. The place they'd usually go hired young female waitresses who they would ogle during the course of the night. Most of the time, the waitresses wore low cut tops that revealed plenty of cleavage and either tight booty shorts or short skirts. The guys knew they dressed that way to increase their tips and it worked. The wait staff would flirt with them, tolerate their suggestive comments, and seemed to lean or bend over in front of the guys, knowing full well they were checking them out.

One night, they got a new waitress who didn't fit the mold of most of the other waitresses. The new waitress was Brandi, who wore a short black pleated skirt that resembled those worn by a cheerleader, with white spandex shorts underneath. The shorts clung tightly to her firm little ass and fit into the crack of her ass. She has big brown eyes and shoulder length brown hair that she had in pigtails that gave her a look of innocence.

Brandi has slender legs and wore a tank top with what appeared to be a crop top T-shirt underneath. However, she was flat chested and the only bumps in her chest came from her nipples, which protruded just a little through her top.

Normally, Harry was attracted to women who had more meat on their bones, as he would say. He liked a woman with a round ass, long athletic legs, and nice sized breasts. However, he found himself infatuated with Brandi. He found himself staring at her chest and her protruding nipples, even though those were the only things that stood out on her chest.

He also kept a watchful eye on Brandi when she was serving other tables. He was fascinated whenever he got a peek at her tight little ass in her white shorts whenever she bent over at another table. He knew they were her shorts and not her panties but he still enjoyed the view. He found himself trying to get a peek at her nipples down her shirt when she served them their food and drinks. It didn't bother him that she had no cleavage at all. Brandi wasn't drop dead gorgeous like some of the other waitresses, but she was cute in her own understated way.

Rod commented, "It's just our luck that we got the waitress with no ass or tits."

That led Harry to reply, "I don't know, I think she's kind of cute."

Mike added, "She can't compare to that blonde over there with the big tits and check out that ass."

"Yeah, but a girl like that knows she's cute and is full of herself. Brandi is more real than her. I like the shy type," Harry replied.

Harry's friends just shook their heads in disagreement. Over the course of the next couple of hours, Harry kept a watchful eye on Brandi. He liked her unpretentious manner. She looked good without trying to flaunt herself. He didn't realize she didn't have the confidence to flaunt herself.

He couldn't control the infatuation he was feeling.

He knew he shouldn't be undressing her with his eyes but he couldn't help himself. He wanted to see Brandi's bare chest and her cute little butt. He wondered if she had a full bush, trimmed it, or was completely bare.

Rod, who was on the heavy side, had a few too many drinks by the end of the night and commented to Brandi, "What's it like to have the smallest boobs in the bar?'

The rest of the guys told him not to be an asshole, but Brandi quickly replied, "I don't know, what's it like for you to have bigger boobs than some of the women?"

Harry, John, and Mike began laughing their asses off while Rod turned red and looked away. They could tell he was pissed off. The guys were telling Rod how he needed to wear a bra and he might be able to get a job at the bar if he showed more cleavage. Rod didn't think it was funny, but that didn't stop his friends.

On the way out of the bar to wait for their rideshare, Harry stopped to talk to Brandi and apologize for his friend's conduct.

"I'm sorry, Brandi. Our friend had too much to drink. Don't worry, we'll never let him forget how you shut him down."

"That's okay. I've been dealing with assholes like him my whole life."

"That doesn't excuse his behavior," Harry said and slipped her an extra sizable tip.

"That isn't necessary," she said.

"You're a nice young woman, Brandi, you deserve better. By the way, my name's Harry."

She smiled and replied, "Thanks Harry. I appreciate it."

From that day forward, anytime Harry went into the sports bar, he asked to be seated at Brandi's table. If he was in there by himself, she would stop and talk to him whenever she had a free moment. He always marveled at her petite little body, especially when she would wear a tight tank top that hugged her dainty bosoms or tight shorts that highlighted her pint sized booty. He always made sure he left her a big tip.

One night he was in there with the guys and they noticed his infatuation with Brandi and were teasing him about her being his girlfriend.

John even told Brandi, "I think our friend here has a little crush on you. I bet he wants you to be his girlfriend."

Before Harry could tell them to be quiet, Brandi replied, "Hey, I've dated worse guys than Harry, maybe I should give him a shot."

John and Mike began to laugh and were teasing Harry, telling him to go for it. Rod told him to be careful because a young girl might be harmful to his health.

Mike joked, "You should get a note from your doctor first."

"Fuck you, Mike," Harry replied in jest.

Over the course of the next few months, Harry and Brandi became more familiar with each other. They would chat when he was in the bar by himself. She knew his wife had passed away. Harry knew that Brandi was unlucky in love and had some serious confidence issues.

She would make comments like, "Guys seem more interested in girls with nicer figures than me," or, "Heck, I can't even fill out a training bra."

When he would tell her, "You're a pretty young lady, Brandi. You'll find Mr. Right when you least expect it," she thought he was just being kind, but she liked his kindness.

Even though they had some friendly conversations, Harry was still undressing Brandi with his eyes, picturing her naked as she walked around from table to table or when they were conversing. She noticed his wandering eyes but rejected the thought that Harry might be attracted to her.

Harry started watching porn with a young woman and an older man. He especially liked it if the actress had small breasts. He would imagine being naked with Brandi, touching her soft tender skin, playing with her tiny titties, eating her young pussy, and fucking her in several positions.

His infatuation with Brandi only increased after a recent trip to the bar for a quick beer and burger. While Brandi was serving him, he got a split second peek down her shirt. Her nipples looked so tasty that he had to control his urge to reach out and touch them. The little peek served as fuel for his jerk off session when he got home. She gave him a little grin like she knew he was checking her out. He wondered if she did it on purpose.

One night when Harry was leaving the bar, he saw Brandi in the parking lot trying to start her car. She was fighting back tears and was clearly frustrated, so he offered to help her. He got her car started by jump starting the battery, but he noticed the car was old and in need of some other repairs.

"You need a new battery and the car doesn't sound too good."

"I know. The mechanic told me I needed a lot more done but I can't afford it and my rent is due next week."

"I'll tell you what Brandi, let me take your car home and I'll work on it tomorrow. Take my car for tonight and call me later tomorrow. I've been fixing up cars since I was a teen and can save you some money. You can pay me back whenever you can."

"I couldn't do that, Harry. I don't know when I'd be able to pay you. Besides, what will you do for a car?"

"Don't worry, we'll figure something out. I have two other cars, so it's not a problem. Come on, I'm retired and looking for stuff to do. You'll be doing me a favor too."

Brandi didn't have any other options so he let Harry take her car home and she took his. They exchanged phone numbers before they left. Brandi wasn't sure she did the right thing but at least Harry wouldn't rip her off.

The next day, when Harry called to tell Brandi her car was ready, her first question was, "How much do I owe you?"

"We'll talk about that when you get here."

She was nervous because she knew how much the mechanic wanted and there was no way she had close to that amount. Even if Harry charged her half that amount, she still didn't have it.

Harry lived in a well to do suburb in a four bedroom ranch home with a two and a half car garage. Her car was parked in the driveway and looked like it was freshly washed and waxed. Harry greeted her at the door and invited her in. His home was beautiful with a spacious living room, dining room, and a gourmet kitchen.

He handed her the keys and said, "Your car was in pretty rough shape. It's got new brakes, a new battery, I changed the oil, and found you some decent tires."

"Holy shit, Harry, how much did all that cost?"

"Don't worry about it. I know you don't have a lot of money. I'm pretty secure and I had fun doing it."

"No way, Harry. I can't let you pay for all that. I insist on paying you back. I can do it a little at a time but I'm going to pay you back."

"You're a sweet, adorable young lady, Brandi. Consider this your lucky day. The payment is me doing a good deed for someone."

"No way I can let you pay for all that. If you won't take any money, I can work it off," Brandi replied, half expecting him to want her to perform sexual favors, which she probably would have done.

"I don't know, Brandi, it isn't necessary."

She was shocked when he didn't want anything but replied, "How about if I clean your house for you once or twice a week?"

"Fine, if that makes you happy. I haven't been keeping up with the housework anyway."

Brandi held her hand out and said, "It's settled, it's a deal," and they shook hands.

The truth be told, Harry was looking forward to having some company around the house once a week and was thrilled at the prospect of spending time with Brandi away from the bar. He was so happy to see her at his house that he invited her to stay for dinner.

"Would you like to stay for dinner? I'm about to throw some chicken on the grill. I made a salad and I have some baked potatoes. I usually cook a lot at a time and have leftovers for the next couple of days."

"I don't know, Harry, you've already done so much for me. I don't want to impose."

"It's no problem at all."

"To be honest, I'm sick of eating Ramen noodles. Are you sure it's okay?"

"It's more than okay. I insist."

"You're too good to me, Harry."

Harry gave Brandi a quick tour of his house. She was very impressed but also sizing up what it would take to clean the house once a week. Part of her wondered if he was going to try to lure her into the bedroom but that never happened.

He poured a glass of wine for each of them to enjoy while he grilled the chicken. As he was grilling, Harry marvelled at Brandi's beauty and innocence. He felt fortunate to have such a cute dinner guest. He didn't want to stare and make her feel uncomfortable but he kept stealing glances at her T-shirt where he could faintly see her brown areola underneath. She was wearing skin tight black leggings and he enjoyed the sight of her diminutive ass as she moved about the kitchen and patio.

Over dinner, Brandi shared that she hoped to go to nursing school someday but wasn't sure that was ever going to happen because she needed to keep working to support herself. She revealed she wasn't dating anyone and had no prospects in mind. She spent most of her time either working or hanging out with her friends. Both of her roommates were dating, so she felt left out most of the time.

Harry said he spent most of his day either playing golf, tinkering with his cars, working out at the gym, and hanging out at the sports bar. He told Brandi he wasn't ready to start dating anyone despite his friends' efforts to fix him up.

They had a wonderful evening together. It broke up the loneliness Harry had been experiencing and Brandi found someone who was helping her more than he would ever know. They decided she'd clean his house on Wednesdays, her day off from the bar. She was still half expecting Harry to try to get her into his bedroom, but he was a true gentleman. It only reinforced the feeling that Harry was truly a good guy.

Every Wednesday thereafter, Brandi showed up at Harry's house to help with the cleaning. It wasn't that difficult seeing that Harry was single, but a deal is a deal. They actually spent more time talking and she always stayed for dinner. She began to stay later and later which led to her roommates wondering if she was sleeping with Harry.

Julie out and out asked Brandi, "Are you fucking, Harry?"

"No. I told you, he fixed my car and I'm cleaning his house to pay him back."

"I know but you're staying there pretty late. Has he tried to get you to have sex?"

"No, it's not like that at all. He's still grieving the death of his wife."

"Would you do it if he asked? I mean, you've been in a drought and, you know, he seems like a good guy from what you've told me."

"I don't know. I mean, I've thought about it. No one's ever treated me that well before."

"I've known you a long time, Brandi, and you've fucked worse guys than Harry."

They both started to laugh because Julie just told her friend the absolute truth about her past love life. The truth is, Brandi didn't think Harry was attracted to her. She didn't know that Harry was fantasizing about her all the time. He didn't think she'd be attracted to an older man and didn't want to ruin their friendship.

The next time she cleaned the house on a Wednesday, Brandi was looking at Harry in a different manner. He had a distinguished look about him. He was tall, had salt and pepper hair and a five o'clock shadow beard. He worked out every day, so he was in very good shape even though he had a bit of a dad body going on around his stomach. He was kind, caring, and had a great sense of humor.

After she cleaned the house, they had dinner and drinks as usual. Harry asked her if she'd like to get high and showed her a cannabis vape pen. She loved that idea. He told her if she got too high, she could sleep in the guest bedroom if she wanted.

They sat back, took some drags off the vape pen, sipped their drinks and sat back to watch a movie on TV. That evening, Brandi was sitting on the sofa in her little booty shorts and tank top with her legs stretched out toward Harry, who was sitting on the opposite end of the sofa.

Brandi was wiggling her toes and commented, "Aw, I need to get new shoes for work; my feet are killing me."

"You know, I used to give my wife a great foot massage."

"I wasn't suggesting that you massage my feet, Harry."

"Well, it's up to you, Brandi. I swear, I don't have any ulterior motives. I promise."

She thought it over for a moment or two, and replied, "I guess it would be alright. No one's ever given me a foot massage before."

"Well, you're in for a treat then."

Harry moved closer to Brandi and turned sideways on the sofa and took her right foot in his hands. He started at her heel and pressed his thumbs in deep. He moved to her sole and gave it long, hard strokes.

"Oh my god, that's amazing."

He continued to massage the ball of her foot, then rubbed each individual tender toe, one by one. He worked his way back to the heel and up to her tender toes multiple times and switched to do the same to the other foot.

Harry was looking up at Brandi the entire time to see the look of satisfaction and relaxation on her face. He spent a good thirty to forty minutes massaging her feet and working his hands up her calves. She wondered if Harry had a foot fetish and would ask her to have sex with him. She was kind of hoping he would. Between the drinks, the vape pen, and the massage, her pussy was itching for attention too.

When he was done massaging her feet, Brandi was waiting for him to ask for more, but instead, he got up to get them more wine and sat back down at the end of the sofa. She was beginning to think he might be gay or that she was that unattractive.

She was high and horny which led Brandi to blurt out, "Can I ask you a personal question, Harry?"

"Sure, I guess."

"When was the last time you had sex?"

"Oh wow. It doesn't get more personal than that. It was well before my wife died. It's been a while. Why?"

"Do you want to have sex?"

Harry almost choked on his wine while being caught totally off guard. He didn't know what to do. He hadn't had sex with a woman other than his wife in over thirty years. He was torn between lust for a lovely young woman and a panic attack.

"Are you talking about you and me?"

Brandi snickered and replied, "Well yeah, there's no one else here. I understand if you aren't attracted to me."

"Are you kidding? I think you're gorgeous. There's nothing more that I want to do. I've wanted to sleep with you for a long time, but I didn't want to scare you off."

"You don't have to worry about scaring me off. I want to do it with you."

Harry sat there dumbfounded, not knowing what to do next, as he watched Brandi slowly move closer to him, his heart beating double time. He swallowed hard as she straddled his lap, put her arms around him, and gave him a soft, sensuous kiss. It was difficult for him to believe this was actually happening.

One kiss turned into another, with several more increasing in length and passion. Brandi was horny to begin with, but her inhibitions were weakened by the drugs and alcohol, and the sensuous foot massage sent her over the edge. She had never been that bold before and she was now going to experience having sex with an older man. She wondered if it would be as good as she had heard, such as being more attentive to a woman's needs and taking their time with foreplay. It was starting just fine.

Harry's hands were stroking Brandi's slender bare legs before he firmly gripped her small butt. He sank his fingers into her flesh as she moaned while they continued to passionately make out. He ran his hands up and down her back then moved to the front to play with her nipples through her T-shirt. He dreamed of one day getting his hands on them every time he saw her. When Harry began to tug at the bottom of Brandi's T-shirt, she broke from their kiss and raised her arms, allowing him to slip it over her head.

When she tried to kiss him again, he told her, "No wait, I want to get a good look at your breasts."

"There's not much to see."

"I think they're beautiful."

Harry stared at Brandi's underdeveloped chest, marveling at their miniature size. He didn't understand why he was so attracted to her flat chest, but he didn't care. All he knew was her nipples looked delicious and he leaned forward to suck on one while tweaking the other, then switching sides. No one had ever paid that much attention to her breasts before and she loved it. She didn't feel self conscious anymore. Harry's lust for her made her feel sexy and desired.

He sucked on her nipples for a while, completely entranced by their diminutive size, before he asked, "Are you sure you want to do this, Brandi?"

"I'm more sure than I've ever been."

He then stood up and carried Brandi to the guest bedroom. He held her in his arms while she had her arms wrapped around his neck. Harry had literally and figuratively swept her off her feet. She enjoyed being held in his strong arms as he brought her into the bedroom.

Harry laid her down gently on the bed then pulled off her shorts and then began to slide her bikini underwear down as she raised her hips so he could remove them. Once naked, Harry threw her underwear to the side and gazed at her naked body. The first thing he noticed was her hairy bush. His eyes followed Brandi's nude body from head to toe and back again.

She asked him, "What are you staring at?"

"You're gorgeous, Brandi. I never thought I'd ever have a beautiful young woman like you in my bed."

No one had ever told Brandi she was beautiful or gorgeous before. It made her want to fuck Harry even more. She felt free and alive and desperately wanted to please him. She watched as he disrobed and joined her on the bed.

Harry had well defined muscles in his arms, chest, and legs. He had a light coating of dark hair over his body but not too much. His hard cock looked a little larger than average. Brandi thought he was going to fuck her immediately, but instead, he laid next to her and began to kiss her again.

He kissed and nibbled on her neck which she didn't know was so sexually sensitive until that moment. Harry spent even more time focusing on her nipples again and then kissed and licked his way down her torso. He massaged her left thigh while kissing and nibbling on the right. The entire time, he never touched her pussy which was driving her wild, but that was the whole point.

Harry took Brandi's smallish feet and brought them together around his cock while staring at her naked body. He rubbed her feet all over his cock and balls before kissing his way back up her thighs.

Brandi instinctively opened her legs as a silent invitation to fuck her, but Harry had other ideas. He spread her legs a little wider and began to finger fuck her while rubbing her clit with his thumb. He found her to be soaking wet.

Brandi began to squirm at his touch, reveling in the slow, sensual foreplay Harry was doing to her. When she was about to orgasm, he slowed down his digital movements, toying with her. He brought her to the edge several times, teasing her mercilessly. She had never experienced such intense foreplay before. She needed some release but Harry would decide when it would happen.

He laid down between her legs and began to kiss her inner thighs. He could smell her excitement, a scent that he would never forget. His confidence bloomed from knowing he could sexually excite a woman young enough to be his daughter. When he began to kiss and tenderly lick her pussy lips, Brandi pulled his head closer.

Brandi arched her back and sighed when Harry inserted his tongue into her juicy pussy. He hadn't tasted a pussy in years and didn't realize how much he missed it until that moment. He feasted on her tasty young pussy.

She was squirming even more when Harry replaced his tongue with his finger so he could focus his efforts on her clit. He gave her clit quick butterfly flicks and when he felt she was close to orgasm, he wrapped his lips around it and used his tongue to assist in sucking the orgasm out of Brandi.

"Oh my fucking god, I'm going to cum. Oh fuck," she cried out as she clutched Harry's head while wiggling her hips to rub her pussy against his tongue.

A flow of her juices squirted into Harry's mouth, catching him by surprise but he never stopped licking and sucking her clit until her body relaxed. When he lifted his head, Brandi's eyes were closed and her chest was heaving while catching her breath.

"Holy shit, Harry, you know how to eat some pussy. I've never cum so hard before."

"And I'm not done with you yet," he replied before going to work on her pussy again.

Brandi was lucky if a guy gave her one orgasm, let alone two. Harry was fingering her hairy pussy again while working his magic tongue on her clit. In no time, he had her squirming again and brought her to another, less intense orgasm. Harry didn't stop until Brandi had another orgasm.

It was then that Brandi told him, "No more. I can't cum again."

Harry sucked her tender nipples while she recuperated and told him, "Now, it's your turn."

She knelt between his legs and began to lick his balls and slowly stroke his cock. She took her time licking his balls and shaft before working her way up to give the head butterfly flicks. She squeezed more precum from the tip and licked it off.

"That feels good, babe, keep it up."

Brandi wrapped her tongue around the head, working it over for a little while and then took his dick between her sweet lips. With each bob of her head, Brandi took more and more of Harry's dick into her mouth until her nose pressed against his abdomen. As she bobbed her head, Brandi worked her tongue over and around the head and shaft. It was now her turn to have Harry squirming on the bed.

"Oh fuck, you're good, Brandi."

Harry wondered how many dicks Brandi sucked to get to be that good at giving blow jobs, but figured it didn't matter. He felt his balls filling with cum and asked Brandi to stop because he didn't want to cum too soon.

"I want some of your pussy, darling."

"I want your cock in me too, Harry."

Brandi laid back on the bed, spread her legs, and said, "Come here and fuck me. I need to feel your cock inside me."

Harry gazed down at Brandi, who had that look of lust in her eyes with that hairy pussy waiting for him. He knelt between her legs and rubbed his dick up and down her slick pussy, the hair around it already matted from her juices.

He took a moment to savor the moment and then slowly slid himself into Brandi's tight, young pussy. He dreamt of this moment for months and masturbated at the thought of fucking Brandi. Now, his dream was coming true. Her pussy felt so tight, if was like it had a firm grip on his cock.

As he picked up the pace of his thrusts, Brandi told him, "Fuck me, Harry. Your cock feels sooo good. Oh yes, fuck me, fuck meeee."

While Harry knew fucking a young woman like Brandi would feel fantastic, it turned out to be better than he ever imagined.

"I dreamed of fucking you. From the first time I saw you, Brandi. I wanted you."

"I've had a crush on you too, Harry. You're a fantastic lover."

They fucked in the missionary position for a while, with Harry slowing down at times to control his orgasm. He then bent Brandi over to take her from behind. He took a mental picture of her slender legs and compact ass as he approached her from behind.

"Each time I saw you in the bar, I wanted to bend you over a table and fuck you," he said as he slid his dick into her.

Harry groped Brandi's dainty ass as he fucked her. He spread her ass cheeks to check out her little asshole. He then reached around to play with her nipples before grasping her ass again.

Brandi could tell Harry was getting close to orgasm by the increased intensity of his breathing and told him, "Cum for me, Harry. Cum in my pussy. I want to make you cum. Fuck me, fuck me hard."

Harry was fucking Brandi hard and fast as he could. Her hair was flopping around and he grabbed a handful of it while spanking her ass with the other hand.

"That's it, Harry, fuck me hard. Cum for me."

Harry held out as long as he could but he had too much cum built up to hold back any longer.

"Oh fuck, I'm cumming. AAAHHHHHHHHH."

Harry shot a huge load of cum from deep within his balls into Brandi's pussy. He could feel her squeezing her pussy tighter to help milk the cum out of him. He lunged into her several times until he had released every drop of jizz into his young lover. He then collapsed onto her back, breathing heavily in an attempt to catch his breath. He eventually withdrew from Brandi and fell onto his back.

"Holy shit, Brandi, I can't remember when or if I've ever cum that much. I needed that."

"You're the best lover I've ever had, Harry. That was fun."

"You're so fucking gorgeous and sexy, Brandi. Damn, that was good."

"No one's ever told me I was gorgeous or sexy before."

"Well, I'm telling you now," he replied and kissed her passionately.

Brandi then said, "I guess I should be going now," and started to gather her clothes.

"You know, we got high and we've been drinking, maybe you should stay here tonight."

"Are you sure?" Brandi asked.

"It's not a problem at all. You can sleep here or, uh, in my room if you like."

Brandi thought for a moment and replied, "I wouldn't mind sleeping in your room if you don't mind."

"It's actually my preference but I didn't want to put any pressure on you after, you know, what we just did. By the way, you were amazing."

Brandi went around the house gathering her clothes and took a shower. When she came out, Harry had brownies baking in the oven while he quickly showered. He put on a T-shirt and boxer shorts. Brandi had on her T-shirt and panties, her hair was still wet.

He took one look at Brandi and commented, "I feel like the luckiest man in the world right now."

"Heck, I feel like I'm the lucky one. I just found a guy who gave me the best sex ever and who has already done more for me than any other man."

"I'm glad I can help you out, but it's kind of sad in a way."

"Tell me about it."

"I got the munchies after getting high so I made some brownies, but you can get something else from the fridge if you want."

"Hey, a way to a girl's heart is with chocolate."

They sat around the kitchen island chomping down the warm brownies. There's nothing like brownies fresh from the oven. Both of them were pleasantly surprised by the unforeseen turn in their relationship.

"I gotta tell you, Brandi, I didn't see tonight happening. What made you suggest that we, uh, have sex?"

"To be honest, I was half expecting you to ask me after you fixed my car. I thought there might be some strings attached to your generosity."

"I would never ask that of anyone. I'm financially secure and I was just trying to help someone."

"I know, that's when I knew you were genuinely a kind person. I haven't met too many people like you. I find your sincerity attractive. It's been a while since I've had sex. I've been burned too many times by guys. I was horny to begin with, but that foot massage and getting high put me over the edge. I took a chance and I'm glad I did."

I'm glad you did too, Brandi. I mean, I've thought about being with you, but I never thought it would happen. I mean, I'm so much older than you."

"That was part of the attraction, Harry. You're confident, mature, kind, and handsome."

"I'm handsome?"

"Yeah and now I know you're damn good at eating pussy," Brandi said and gave Harry a wink.

"You know, that doesn't have to be the last time I eat your pussy," Harry replied and returned the wink.

"If that's an offer, I accept."

"Only if you return the favor."

"It's a deal, Harry," Brandi replied and held out her hand to shake on it.

Harry took her hand, pulled her close, kissed her, and led her off to the bedroom. He couldn't remember the last time he had sex twice in the same night, but all that mattered to him was that it was happening that night. Brandi found herself a genuinely great guy who found her to be beautiful and sexy. Her self esteem shot through the roof for the first time in her life. The fact that he was more than twice her age didn't matter. They were living in the moment and that moment was the most thrilling moment of their lives; there was no need to ruin it with dumb questions.

Once they got into the bedroom, they quickly stripped off their clothes and climbed onto the bed. They were kissing and letting their hands roam over each other's bodies. Shortly thereafter, they were exploring each other with their mouths. Brandi took Harry's dick into her mouth with her torso close to Harry's face. That gave him an idea.

"Swing your legs over my head so I can lick you, too."

They were now in a sixty nine position with Brandi on top, simultaneously orally pleasing each other. Brandi was licking and sucking Harry from the tip of his dick down to his balls, exploring every inch of him with her lips, tongue, and mouth.

Harry's hands were cupping Brandi's petite ass while he explored her pussy with his tongue. He had a great view of her hot pussy and asshole. Sometimes Brandi would sit upright on Harry's face to experience a deeper penetration of his tongue, bringing her ass even closer to his face. She would rub her pussy against his lips and tongue and then go back to work sucking his dick.

Brandi's young pussy tasted divine. Harry couldn't get enough of it. He was encouraged by her moans of pleasure and her encouragement to continue.

"Oh fuck, Harry, I love how you eat my pussy. Oh my god, it feels so good. UUmmmm."

"Oh yeah, suck my dick, baby. Your lips feel so good."

After Harry licked Brandi to two more orgasms, she turned around, aimed his hard cock at her pussy, and slowly sank down on it. Her eyes were closed as she began to ride his cock while rolling her hips. He reached up to play with her sensitive nipples with one hand while keeping a firm grip on her tight little ass with the other. She would gaze down at him, her face flushed from excitement and lust in her eyes.

Harry never imagined he'd be able to sexually satisfy and keep up with a much younger woman. It gave his confidence a boost. Brandi wished she had discovered the joys of being with a more mature man sooner.

When Brandi began to tire, Harry turned her over without disengaging from her and began to fuck her in the missionary position. He slowly pumped his dick in and out of his young lover while gazing into her big brown eyes. There was an undeniable sexual connection between them, but they both silently wondered if there was a deeper connection.

After he fucked Brandi missionary style for a while, Harry said, "I'm ready to cum but I want to fuck you from behind."

"You can fuck me any way you want, Harry," she replied and quickly got down on all fours, offering herself to her mature lover.

When he entered her, Brandi told him, "Fuck me, Harry. Oh, your cock feels so good. Fuck me harder. I want to make you cum. Fuck me."

"Oh baby, your pussy is so fucking tight. I love it. Oh fuck, I'm gonna cum."

He unleashed his second load of cum into her that night. When he was done, they both collapsed onto the bed.

"I'm done, Brandi. You wore me out."

"I'm done, too. That was amazing, Harry."

"You spoiled me, Brandi. I love the way you sucked my dick and your pussy is so friggin tight."

They both cleaned up and returned to the bedroom where Brandi fell asleep in Harry's arms, cuddled up against his warm body. She had never felt so secure as she had that night, sexually satisfied and being held by a man who truly cared for her.

They both slept in the next morning and when they woke up, they both didn't know what to say. They hoped the other didn't have any regrets. Harry was afraid that he had gotten a vulnerable young woman drunk and high and hoped she didn't think he took advantage of her even though she was the one who suggested having sex.

Brandi's insecurities kicked in and she wondered if what Harry told her was all bullshit in the heat of the moment. Yes, he has been kind and generous with her but she found it difficult to believe that someone found her to be beautiful and sexy. She didn't want to be disappointed like she had been so many times before. It was almost like Harry had been reading her mind when they met up in the kitchen while he was cooking breakfast.

"I hope you like bacon and eggs with some toast, because that's what I'm making."

"Sounds wonderful to me."

As he was moving about the kitchen, Harry told Brandi, "I just want you to know, last night was unforgettable. You're an amazing, beautiful, and sexy woman. I haven't felt that kind of happiness in a long time."

A tear rolled down Brandi's cheek, causing Harry to ask, "What's wrong? What did I do?"

A sniffling Brandi replied, "You're just too good to be true, that's all."

Harry snickered and said, "Okay, I'll try and be more of an asshole."

"I'm used to that. I'm not used to someone being so good to me."

Harry gave Brandi a big hug and told her, "I don't know what's going on between us but let's just enjoy it. I like being with you, so let's not overthink it, okay?"

"It's a deal," she responded and held out her hand to shake on it.

Harry pulled her closer, gave her a big hug, and a kiss. They embraced until they realized the eggs were still cooking. They enjoyed a casual breakfast with some slightly overcooked scrambled eggs.

As they ate, Harry's eyes kept scanning Brandi's chest and her nipples through her T-shirt. He admired her soft legs as she sat with her legs crossed in only her panties. When she moved about the kitchen, he focused on her pint sized ass as it wiggled underneath her panties and the dark patch of hair visible in front.

When Brandi announced, "I have to get going. I have to change my clothes, do some laundry and do some shopping before I go to work at 4," Harry took her in his arms and kissed her deeply, a kiss she willingly returned with equal passion. His hands roamed over her scantily clad body, from her soft ass to her hardened nipples and her damp panties.

Brandi could feel his growing erection pressing against her torso as she clutched his ass and pulled him closer. Harry walked her over to the kitchen table as they continued to kiss and then bent her over.

"I really have to get going, Harry."

Her words said one thing but her body said something different, from her soft moans to the increasing dampness between her legs. She mildly protested as he pulled her panties down and kicked her feet wider apart.

He pulled his now erect cock out of his boxers and rubbed it against her pussy lips and said, "I'll stop if you want me to."

She didn't say anything but pressed her hips backward against his cock. Harry pressed himself forward in return. Brandi moaned softly as Harry's dick entered her. She moaned louder as he began to thrust himself into her.

"Fuck me, Harry. It feels so good."

"You're so darn sexy. I didn't want to let you go without fucking you again."

Harry was drilling that tight young pussy. Brandi was equally enjoying their impromptu morning fuck. She had never experienced a lover who lusted for her in the way Harry did. His lust turned her on in ways she never felt before. He wanted her in the worst way and she wanted to please him. Brandi's hand drifted down between her legs and she began to rub her clit as Harry was fucking her. She came first and that triggered Harry's shortly thereafter.

With their morning quickie now over, Brandi said, "I really have to get going."

"I know. Call me when you're free. I had an incredible time."

"Me too, Harry. You're quite a guy."

When Brandi got home, Julie couldn't wait to hear all the juicy details. She knew something was up when Brandi sent her a text message saying she would be staying at Harry's.

At first, Brandi played coy and said, "Nothing happened. I just had too much to drink and we got high so Harry didn't want me to drive home."

"Brandi, I've known you long enough to know when you're bullshitting me. Besides, you have that just fucked look on your face. How was it?"

Brandi hesitated, trying to think of what she should say, then got a huge smile on her face and said. "I think it was the best sex I've ever had. We fucked twice last night and once again this morning. And let me tell you, that man knows how to eat pussy. He made me cum three times before he even fucked me."

Julie started to laugh and said, "Get the fuck outta here you fucking slut. Good for you. Shit, now I'm jealous. Maybe I need to find an older guy."

"He's so sweet and kind and generous. I only wish he was younger."

"Hey girl, you don't have to marry him. Enjoy it while you can."

"Funny, that's what he said. I've got to go shower. I still have some of his cum in me," Brandi said with a wink and a smile.

"Now you're just rubbing it in. That's mean."

Before Brandi got in the shower, she took a couple of naked selfies of herself and sent them to Harry, who responded, "You're such a cocktease. I can't wait to see you again."

He also sent her a naked picture of himself, and Brandi replied, "Who's the tease now?"

All through the day, Harry would open his phone to look at the pictures Brandi sent him and fondly recall all the fun they had.

Later that evening, he got a text from John asking if he wanted to go out and watch the football game. Harry told him he was kind of tired but they could order a pizza and watch the game at his house. Brandi was working until midnight so he knew she wouldn't be coming over. Besides, he didn't want to crowd her by going to the bar.

Before the game started, John asked Harry, "How's it going with Brandi cleaning your house?"

"It's going good. It's not like it gets that dirty. It's nice to have someone to dust and do the floors."

"I don't want to pry, but I noticed Brandi's car in your driveway when I went to work this morning."

"After she got done cleaning, we had dinner, had a few drinks, and got high. I didn't want her driving so she spent the night in the guest bedroom."

"That's too bad. I was hoping you were going to tell me you got laid."

Harry turned to his friend and got a big smile on your face, to which John commented, "You dog. You didn't."

Harry was dying to brag to someone and told John, "You gotta promise you won't tell a soul. I've known you since high school and I trust you."

"My lips are sealed, bro. How was it?"

"It was fucking amazing. She's one hot lady. We fucked twice last night and once again before she left this morning."

"Hot damn, motherfucker."

"She may be tiny, but she's a wildcat in bed. It was even her who suggested we have sex."

"Get the fuck outta here. You're so lucky."

"Do you promise not to laugh?"

"Alright, Harry, I promise."

"I had to go to the chiropractor this morning, but it was worth it."

John burst out laughing and couldn't stop.

"You promised not to laugh," Harry replied but he was laughing along with John.

"That's what you get for getting involved with a young woman, you old fart."

John was happy for his friend. He could tell his best friend was feeling better by his smile and just the way he carried himself. He witnessed how hard Harry took his wife's illness and death and knew he needed someone to bring him out of his funk.

The next day, Harry waited until mid-morning before he sent Brandi a text that read, "Hey, I'm going to do some clothes shopping today. Do you want to come with me to help me out?"

"Sure, but I have to be home by 3 so I can get to work by 4."

"No problem. I'll pick you up in a few minutes."

Brandi helped Harry pick out a couple of polo shirts and some shorts before he told her, "Let's go someplace so you can get something."

"We don't have to do that."

"Come on, what woman doesn't want new clothes? I'm buying. I know you need some new shoes for work."

"Yeah, but if I get new shoes, you won't have to give me a foot massage anymore."

"I won't have to but I will... if you want, of course."

"You're too good to me, Harry."

"You deserve it."

The first thing they did was get Brandi a pair of high end running shoes that wouldn't kill her feet while working. They felt like she was walking on clouds. She never would have been able to afford them on her own.

They then went to a store that caters to petite women, where Brandi bought several new tops, leggings, shorts, skirts, jeans, and panties. Harry encouraged her to buy more but she told him he did enough.

When Brandi got back to her apartment, Julie commented, "Damn, it looks like someone found herself a sugar daddy."

"He wanted to buy me stuff. I tried to tell him no, but he insisted. I think he may have bought me more if I wanted."

She had to hurry to get ready for work, but before she left, Brandi took a selfie of herself wearing a new top, shorts, and her new shoes.

When Harry saw the picture, he commented, "You look great. I'd stop by work to see you, but I know you'll be busy on a Friday night."

"I'll be by on Tuesday if I don't see you before. Thanks for the new clothes. The shoes are so comfortable. I love them."

"It was my pleasure to go shopping with you. Can't wait to see what else you bought."

Harry wouldn't see Brandi for a few days because she worked long shifts on Saturday and Sunday during football season. Those were days she counted on to make good money in tips. They exchanged a few text messages, but Harry knew how busy and exhausted she'd be so he didn't try to get together with her.

Brandi's days off were Tuesday and Wednesday, so Harry sent a message to her that read, "When you come on Tuesday, why don't you pack an overnight bag and we can hang out for a couple of days?"

"Okay. Sounds like fun."

"You can even come Monday night after work if you want."

"Are you sure?"

"Yeah, why not?"

Late Monday night, Brandi arrived at Harry's house still wearing her work clothes. He greeted her with a big hug and kiss.

"I missed you, Brandi."

"I missed you too, Harry."

Brandi looked exhausted, had a backpack with clothes in it, and a couple of sandwiches from the bar.

"I'd like to take a shower and have a bite to eat and just chill," in a subtle hint that sex was off the table for the night.

"That's fine. I'm just glad you're here."

She took a long, hot shower and came out wearing a tank top and shorts with her hair still wet. They sat at the kitchen island with a glass of wine while they ate the sandwiches.

"While you were showering, I thought that maybe tomorrow I'd arrange for you to have a spa day. You can get a manicure, pedicure, a massage, and get your hair done if you want."

"Are you serious?"

"Yeah, it feels great to spoil yourself sometimes."

"I wouldn't know."

"Well, you'll find out tomorrow. Afterward, I want to take you shopping for a new outfit because I want to take you out for a nice dinner. I haven't been out in a long time because I had no one to go with. How does that sound?"

"Shit, did you think I'd say no to that? I don't want you to think I'm taking advantage of you, though."

Harry chuckled, "You'd actually be doing me a favor. I haven't felt this good in a long time. You have no idea what you've done for me."

"You've done a lot for me too, Harry."

"Great, so it's a date then."

They went to bed and fell asleep in each other's arms. Harry had a luxurious king-sized bed and was much more comfortable than hers. She slept until late the next morning. Harry had been up for a while and made sure she had a nice breakfast before Brandi's spa day. The plan was for Brandi to spend a few hours getting pampered and text Harry when she was done. They'd then go shopping, come home, and get ready for dinner.

Brandi spent the afternoon indulging in the benefits of her spa day. She'd never experienced such luxury before. She felt the tension melting away from the firm, experienced hands of the massage therapist. She got soft pink nail polish for her fingernails and toenails. They even did her makeup. Brandi's hair was trimmed nicely and they put in blonde highlights. Needless to say, Brandi felt like a million dollars when they were through.

Harry then took her to an exclusive clothing store that catered to petite women. He gave the salesperson his credit card and told her to let Brandi get whatever she wanted and to spare no expense. Brandi was to text him when she was done. Brandi was a little embarrassed because she could tell the clerk thought Harry was her sugar daddy, but he probably was. She spent over an hour picking out the right dress, shoes, purse, and accessories. No outfit would be complete without the right perfume.

As soon as Harry saw Brandi, he stated, "You look fantastic. How do you feel?"

"I feel wonderful, better than ever. However, I feel guilty for spending all that money."

"I'm telling you, you're doing me a favor. I don't mean to brag but it's a small price to pay to feel so much better than I have been lately. I owe that to you and you can't put a price tag on it."

"Alright, if you say so."

They went back to Harry's to get ready for dinner. Harry wore a hand tailored sport coat with an open collared button down shirt, tailored slacks, Italian leather shoes, and a Rolex watch. He had a before dinner drink while waiting for Brandi.

Brandi called out, "Are you ready for me?"

"I can't wait, darling."

When Harry saw Brandi, she took his breath away. She was wearing a soft pink, mini slip dress with black lace along the top and hem of the dress. She was wearing two inch black sandals with stiletto heels, sheer black pantyhose, a black collared necklace with a small diamond pendant, matching earrings and bracelet, and a small black purse.

He could see her perfectly aligned toes through the nylon fabric of her pantyhose. He could see the gloss shine of her toenails that perfectly matched her fingernails and lipstick. A hint of her hard nipples could be seen poking through the silky material of her dress. He could smell her sweet perfume.

"Brandi, you are absolutely stunning."

She did a little twirl, grinned broadly, and replied, "I feel so pretty. I hope you like it."

"I love it. I'm proud to have you as my date tonight."

"I'm glad you like it. I've never felt like this before, not even on prom night."

"It will be a great night, I promise."

He leaned in to kiss her but Brandi pushed him back and said, "Don't ruin my makeup."

Harry ordered a car service and driver for their date. He wanted Brandi to experience all of the luxuries of a perfect date. He obviously spared no expense. They knew people would be looking at them and judging them, but neither one cared. They were going to have a wonderful night together and nothing or no one was going to spoil it for them. For one night, Brandi felt like a princess and Harry felt like the luckiest man in the world to have a lovely young lady by his side.

Harry took Brandi to a five star steak and seafood restaurant and ordered several items for her to try. She had never had lobster before or filet mignon. She wasn't going to try escargot despite Harry's encouragement. They had chocolate mousse for dessert. It all seemed like a dream to them. Over dinner, Brandi told him all about her spa day and how she never felt better.

"I feel beautiful tonight, Harry, and it's all because of you."

"No, it's not because of me, it's because you are beautiful, Brandi. You're just now realizing it."

Harry's words were melting her heart.

"You know what else I'm feeling, Harry?"

"No, what's that?"

"I'm feeling sexy."

"Umm, you look sexy, too."

"Let's get out of here and go back to your place and see what happens."

"I have some ideas, Brandi."

She winked and replied, "Oh, I bet you do."

They walked out of the restaurant with Brandi holding onto Harry's arm. Other patrons were looking at them. The men were probably envious of Harry and some of the women judged Brandi, but it didn't matter though. Brandi and Harry had something special going on and didn't care what they thought.

Before they got into the car, Harry held Brandi by the waist, held her close to him, and gave her a tender kiss on the lips. She reached up to wrap her arms around his broad shoulders and kissed him in return. There was an undeniable spark between them. On the ride home, Harry placed his hand on Brandi's knee. The simple touch of his warm, masculine hand, sent shivers through her body. She responded by placing her hand on his thigh while giving him a seductive smile.

Harry might have spent a lot of money that day, but he didn't have to worry about that. It was worth every penny to have a perfect evening with a lovely young woman. She made him feel young and alive again. He would have paid even more to feel that way again.

On the ride back home, they kept glancing at one another, not saying a word, and smiling. They both knew what they'd be doing for the rest of the evening. It was only a matter of time. Once they got back to Harry's and closed the door, he slid his hand under her dress, fondled her nylon covered ass and lifted her up.

Brandi kicked off her shoes and wrapped her legs around Harry's waist as they began to kiss. He was rubbing her nylon encased legs as they kissed.

When he let her down, Brandi told him, "I'm so hot tonight. I'll do whatever you want."

"Umm. I'll pour us some more wine and we can talk about that in the bedroom."

Harry brought the entire bottle of wine and a couple of glasses into the bedroom and poured some for himself and Brandi. He also had the cannabis vape pen. They got a little high while sipping wine, then began to kiss again.

Harry's hands ran up and down over Brandi's legs, and he then began to play with her hardened nipples. Brandi was stroking his leg and rubbing his manhood through his pants.

"I haven't stopped thinking about you since the last time you were here, Brandi."

"I can't get you off my mind either. I kept hoping you'd come into the bar but you never did."

"I wanted to give you your space, that's all."

"Well I'm here now," she said and stood up to take off her dress.

Harry missed seeing those delectable nipples and immediately brought her closer so he could suck on them. He sat on the edge of the bed while she stood between his legs, alternately presenting her nipples to Harry's mouth. He was running his hands over her ass and up her thighs. He loved the feel of a nice pair of pantyhose. Through the haze of her hose, Harry could see that she trimmed her pubic hair. He began to rub her pussy and found it to be soaking wet. She was purring softly while running her fingers through his dark hair.

Brandi stepped back to remove her pantyhose but Harry stopped and said, "No don't. Leave them on. I love the feeling of stockings and pantyhose."

She began to strip Harry's clothes off of him. She was so hot, she badly needed to get fucked. She was down on her knees when she unbuckled his belt and removed his pants, socks, and underwear. His hard cock was now bobbing in her face.

Brandi lustfully smiled at Harry as she stroked his cock. She then began to lightly lick and mouth it from the tip down to his balls and back again. She was worshipping his cock with her mouth and tongue, desperately desiring to please him in return for all he's done for her.

She teased him for several minutes before engulfing his cock between her soft lips and deep into her throat. The sounds of her sloppy blow job filled the room. Harry moaned as Brandi expertly sucked his dick while he tweaked her nipples.

Brandi sucked his dick for several minutes and then climbed onto his lap. Harry ripped open the pantyhose to make an opening for his dick. She slid down onto his cock and began to fuck Harry. She rolled her hips while he was either kissing her or sucking on her nipples. He was rubbing her legs and ass the entire time.

"You've made me so hot tonight, Harry. I needed to get fucked. I've been horny all week thinking of you."

"I've wanted to be with you too. You're so fucking hot."

"Is there anything you want me to do? You've been so good to me, I'll do anything."

Harry paused for a few seconds and said, "I want to cum in your mouth after we fuck for a while."

"I'd love to swallow your cum."

Harry stood up and laid her onto the bed and began to pound her tender, tight pussy. She was lifting her hips upward to meet his thrusts. He was looking deep into her eyes while his dick pounded her pussy. She wrapped her arms around his neck and brought it down to kiss him while she wrapped her legs around his back, pulling him in deeper with her feet.

"Fuck me, Harry. I love how you fuck me. You're so good."

"I love your pussy, Brandi. God, it's so tight."

They were rocking the bed from fucking so hard and when he was ready to cum, Harry told Brandi, "I want you on your knees."

Brandi obeyed Harry's wish and quickly got onto her knees while he sat on the edge of the bed. She tucked her hair behind her ear, immediately gobbled down his dick, and began to bob her head.

"Cum for me, Harry. I want to taste your cum. I want to please you so badly."

"Oh fuck, Brandi, your lips feel so good. Oh fuck, oh fuck."

Harry tried to hold out as long as he could but Brandi was too good of a cocksucker to hold out even a second longer. He tensed up, straightened his legs, and lifted his pelvis as he released a flood of cum into Brandi's mouth. Her tongue swirled around the head as her head bobbed, and she jerked her cock. He released multiple wads of cum into her mouth. He could feel his cock ripple from the heavy load he was releasing.

Brandi was surprised by the amount of cum Harry had in his balls, but she was determined to swallow it all. She almost gagged one time but fought off that reflex to continue drinking down his jizz. When his dick began to give her dry heaves, she released it from between her lips and squeezed out a few last drops before releasing her grip on him, lifting her head up, and smiling up at him.

"How did you like that blow job?"

"I've never had a better one, Brandi. Damn you're good."

"Thanks, I tried my best."

Harry fell back to catch his breath as Brandi joined him on the bed after washing down his cum with a couple of sips of wine. They laid there toying with each other's naked bodies. Harry was still enjoying the feeling of her pantyhose and sucking on her nipples. Brandi was fondling Harry's ass, feeling his strong arms, and giving him light kisses on the lips. She was running her pantyhose covered feet and legs over his thighs and calves.

Harry told Brandi, "I think I owe you now."

"You don't owe me anything, but I won't say no if you want to go down on me."

He smiled and began to kiss and nibble his way down her body, starting with the nape of her neck and working his way down to her tender nipples. He loved playing with her flat chest before he kissed his way down her torso while fingering her pussy.

Harry spent a lot of time worshipping Brandi's legs, announcing his love for the softness of her pantyhose. He kissed his way down her legs, and took time to suck on her toes while also massaging her feet. He then had her turn over and worked his way up the back of her legs. He spent time fondling and nibbling on her precious little ass after ripping a bigger opening in her pantyhose. He even inserted his thumb into her backside while he groped her ass and thighs. Brandi was surprised by the insertion of his thumb into her ass but didn't object.

He then got off the bed, dragged her to the edge and knelt before her. He pushed her knees back toward her head to expose her even further. He then wet his middle finger, stuffed it up her ass, and inserted his thumb into her pussy. He watched the look of pure pleasure on Brandi's face and then bent over to tease her clit.

"Oh Harry, that feels amazing. Don't stop."

He continued to stimulate her ass and pussy with his fingers while concentrating his oral efforts on her clit. Brandi's hips were bucking wildly as he was driving her to higher sexual heights. When he began to suck on her clit while swirling his tongue around it, Brandi lifted her hips and groaned so loud it sounded like she was in pain, but she was far from it. It was pure ecstasy.

She flooded his mouth with her orgasmic juices. He licked her to another orgasm before she stopped him. He gazed up at Brandi with a pussy juice mustache, proud of successfully bringing her to multiple orgasms once again.

After Brandi caught her breath, she told Harry, "No one has ever given me multiple orgasms before. Hell, they never even tried. I've never cum like that, ever."

"Experience counts for something."

Brandi's pantyhose were all ripped up so she took them off and playfully threw them at Harry.

As they were sipping their wine, Brandi told Harry, "I was surprised when, you know, you stuck your finger back there."

"Did it bother you?"

"No, I kind of liked it. I was just thrown off a little."

"Have you ever done anal before?"

"No, guys have wanted to, but I was too scared. Is it something you want me to do?"

"Uh, yeah, but only if you're comfortable with it."

"I'll try anything with you, Harry. I trust you."

"If it hurts, I'll stop."

"Alright, we can try it."

Harry got a big smile on his face and got up to get the KY jelly while telling Brandi, "I love that cute little ass of yours. I've been eyeing it up since the first time I saw you."

"Oh, you have, have you?"

"I certainly have."

Harry sat on the edge of the bed again and had Brandi stand between his legs with her back to him. He ran his hands over her pint sized ass and gave her a playful spank. She leaned over and shook her ass for him, causing Harry to pull her into his crotch. She wiggled her ass against his dick and felt it growing as a result. He reached around to tweak her nipples as she worked her ass against him until his cock was erect.

Harry then had Brandi stand to the side and was taken by surprise when he pulled her over his knee and locked her legs around hers. He held her hands behind her back as he brought his hand down onto her ass with a loud smack.

"Hey, what are you doing?" she asked.

"You've been a naughty girl, Brandi."

She caught on real fast and replied, "I've been real bad. I can't help myself."

Harry spanked her a couple of more times and said, "Oh, what am I going to do with you, Brandi?"

"I can't control myself. I love to suck dick and get fucked."

The more Harry spanked her, the more turned on they both got. Brandi was squirming in Harry's lap trying to rub her pussy against his thigh and could feel his erection pressing against her torso.

Harry stopped spanking her, inserted his finger into her pussy, and told her, "My goodness, Brandi, you're soaking wet. I'm going to have to fuck the naughtiness out of you."

"I'll do anything to be a good girl for you."

Harry brought Brandi onto the bed, had her get on all fours, and drove his dick into her pussy. He put his thumb into her ass again as he continued to lightly spank her and tell her what a bad girl she was. Brandi enjoyed a little rough play and pleasing Harry made it even better.

"I thought you were going to, you know, put it back there," Nicki asked.

"All in due time, honey," he replied.

He fucked her for a little while longer before he withdrew. He fondled her ass while she was still bent over. He then grabbed the lube, dripped some on her asshole, and stuck his finger back into her ass. He continued to add more lube and insert his finger into her backside. After he had two fingers inside of her, he placed some lube onto his dick. She was a little anxious and concerned it would be painful.

"Are you ready for this, Brandi?"

"As ready as I'll ever be, I guess."

She braced herself to be sodomized when she felt Harry's dick touch her asshole. He slowly pressed forward as her asshole opened up. He spread her slender cheeks and pushed further into her until the head of his dick disappeared.

"How are you doing there, Brandi?"

"Uh, okay."

"Take a deep breath and try to relax."

She snickered and replied, "That's easy for you to say. No one's sticking a dick in your ass."

He chuckled and pressed in a little further, taking his time to let her get used to him being in her ass before pushing in deeper. It was certainly a different feeling for Brandi. Having a dick in her backside was uncomfortable at first, but once she got used to it, it wasn't so bad. When she felt his stomach against her ass, she knew she took it all.

Harry began to slowly move in and out of Brandi's ass. Her pussy was tight, but her ass was even tighter. When Brandi began to push back against him, Harry knew she wasn't in any pain and began to fuck her ass faster.

"Oh god, your ass feels so good. This is a dream come true."

"Fuck my ass, Harry. I'm such a bad girl. That's it, use my ass."

"This is what happens to bad girls, Brandi."

"I like being bad."

Brandi was thrilled that she was fulfilling a fantasy for Harry. He made her feel beautiful, desired, and sexy. She was more than happy to explore his desires for her. She found it turned her on to be in a submissive prone position while Harry satisfied his sexual needs with her ass. She reached between her legs to rub her clit while taking a dick up her ass.

Harry sodomized her for a while but even after cumming earlier he found his orgasm approaching. As Brandi was bringing herself to orgasm, he couldn't hold any longer. He had a firm grip on her ass when he dumped his load into her ass, cumming shortly after Brandi.

"That's it, Harry, cum for me. Cum in my ass."

After he withdrew from Brandi's ass, Harry collapsed onto his back and commented, "That was awesome, Brandi. How are you doing there?"

"It wasn't as bad as I feared. As a matter of fact, I kind of got into it."

"I noticed that. I'm glad you had fun too."

After they showered, they fell asleep in each other's arms again that night. The next morning, they made breakfast together. Harry enjoyed having someone around the house. Brandi helped relieve his loneliness and brought a smile and laughter to his home. Harry's warm and caring nature filled a void in Brandi's life and gave her a sense of security, comfort, and confidence. The sex was great for both of them, of course.

They enjoyed an afternoon delight which made Harry realize that within that past day, he came in Brandi's mouth, ass, and pussy. Brandi had a caring lover who made sure she came multiple times. Knowing her needs were going to be tended to was an aphrodisiac in a way. Who doesn't love a good orgasm or two or three?

If Brandi had her period, she would offer Harry a blow job or let him fuck her ass. She had a little bit of a submissive side and enjoyed being on her knees serving him orally or anally. She found she liked being a "bad girl" and being spanked.

Over the next couple of months, their lives consisted of Brandi working long hours at the bar and seeing Harry during the day or on her days off. Harry still went out with his friends, played golf, went to the gym, and tinkered with his cars. Their friends knew they were more than just friends but they didn't care what other people thought. Somehow, Harry's kids were upset that he was in a relationship with a much younger woman and didn't care for it, especially his daughter. He explained to them that they weren't around and he was having fun and to mind their own business.

Brandi and Harry looked forward to their time together, but they both knew a long term future together wasn't in the cards. Harry wasn't getting any younger and he knew Brandi had to find someone closer to her age. He was going to enjoy their relationship for as long as he could.

Brandi started helping out behind the bar to pick up some extra hours and was training to be a bartender where she could make better tips. She was learning on the job, but Harry paid for some formal training for Brandi to help her out. She also practiced at his place by making them exotic cocktails as practice.

There came a time when Brandi was less and less available and Harry knew something was up. One night she came over to the house and they had a glorious sexual evening. She was on fire that night. Brandi had several orgasms and Harry came three times which was unusual for him. He came in her mouth, pussy, and ass.

When they were done, Brandi broke the news that she was in a relationship with another man and wanted to explore it further.

"So was this breakup sex, Brandi?"

She had tears in her eyes and could only muster a nod. They both knew this day was coming but it didn't make it any easier. Harry was fighting back the tears as Brandi was getting dressed to leave.

Before leaving, Brandi gave Harry a big hug and told him, "I can never repay you for all you've done for me, Harry. You changed my life, in a good way. I'll never forget you."

"You changed my life too, Brandi. You brought me so much joy, I never thought I'd feel like that again after my wife died. You need to live your life. You're young and have your whole life ahead of you. You know where to find me if you ever need anything."

They were both crying as she walked out the door.

They kept in touch over the years. They even double dated at times. Brandi asked Harry to walk her down the aisle at her wedding. As they were taking that long, slow walk, Harry smiled to himself thinking of all the great times they had together. Her new husband didn't know he had a sexual relationship with Brandi and he never found out.