Bob Wants a Date

Bob Wants a Date

Joe E Hartley

December 2021

A reader requested this story and I must admit I had trouble with all the restrictions he placed on me for this piece. I satisfied all of his criteria and it did turn out to be an interesting piece. What do you think?

joeehartley

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After Bob's wife of thirty-five years died of a fast-growing cancer, he felt lost. He no longer showed the drive at work he had before; the drive that had advanced him to floor manager. He had enough seniority to retire and his pension would make sure he would not have to cut back on standard of living.

He tried to stick it out at work until the normal age of retirement, but six months after he buried his wife and several months short of his 65th birthday, he filled out the paperwork to retire.

He needed a change to clear his head, so he drove to his favorite mountain to lose himself in a week-long hike with a group of fellow nature lovers. It helped, as he knew it would and when he returned home to his empty house, he knew he would be able to start his new life.

He was not a man who liked to be alone and he needed someone to warm his bed on those long, lonely nights. The friends that he had known when he was only half of a couple had stopped coming around to check on him and the aloneness surround him like a cold blanket. He tried to check out the local bars, but he had never been into the bar scene and didn't know how to play the pick-up games.

Bob decided to learn how to navigate the bars and clubs. There were dozens of clubs and bars that offered some promise. He eliminated the ones with the twenty-dollar drinks and young men wearing suits he could not afford. He knew that he'd have to give each one a fair shot and planned on hanging out for several weeks at each so he could get a feel of the clientele.

After a year he had found that most of the women at these bars were not interested in older men and his frustration grew. He shifted his focus to the neighborhood bars and at least found women who would talk to him.

He felt the depression rising and noticed that the holidays were the worst. There were fewer single women in the bars and he turned to porn. He discovered that he did like younger women and also that for some unknown reason he found women's feet erotic.

He would often just go to the mall to watch the women walk by and after two years had to admit that the bar scene was not working for him.

He joined every senior group he could find, but did not want to spend his days playing Bingo. He hiked often to relieve the stress and on the four-year anniversary of his wife's death, one of his hiking buddies suggested he try an online dating service.

Bob went home and did an online search of dating sites. He filled out several profiles and was honest about his age, appearance, and interest. He did not comment on his growing addiction to porn. He wanted a woman younger than him, but not the 30 somethings he found at the bars and not the geriatric set he found at the senior center either.

He outlined the woman he was looking for as athletic, 40-45 years old, and a nature lover.

He posted his profile in the four sites that looked the most promising and started to contact the women whose profiles looked interesting to him.

Over the next month he continued to go to a bar or two every week and engaged in a few senior activities. He had to admit that for an ever-increasing amount of time he was scrolling though porn sites. He found that the women on these dating sites, like the women he tried to talk to in the bars were not interested in older men, most were actually looking for a sugar daddy and he wasn't wealthy enough to fill that role.

Sarah checked her inbox under her profile as she did every morning. She was lonely after the divorce three years ago and was becoming more and more isolated. Her ex was a lawyer who she had supported while he finished law school. She married young and quickly had two boys who grew up in their father's shadow. They were grown now and each had a wife to support them, just like their father had, while they studied to take the bar exam. Neither of her sons were interested in their mother--she did not have enough money or contacts to help them.

She perused the profiles of the men who contacted her through the dating site, and found the same pattern she saw every morning--a bunch of twenty-year old's looking for a mommy figure, but hot. They called her a MILF. She knew she looked good and actually enjoyed the compliment, but she was not interested in playing out some kid's sexual fantasy. What about her sexual fantasies?

She knew she didn't want another hot shot man ready to make his mark on the world. She wanted someone a bit older and stable. Money was not key to her, but she didn't want to support a gigolo either. She had a hard time admitting it at first, but after talking to all of these young men who wanted her to be their mommy, she finally acknowledged that she wanted a daddy. She wanted someone to hold her and tell her she was special. Someone she could look up to and could be there for her when she needed advice.

She decided as she did once a week or so over this last year on this dating site, to check out a few of the profiles. She modified her search to men over 60 and not wearing a suit, or, for that matter, not holding a fish, or standing next to some flashy car.

She immediately rejected the first dozen profiles mostly because they all looked like they belonged in a nursing home. The old adage came to mind that she's heard from several women on these dating sites that most of the older guys were only looking for either a purse or a nurse.

She was ready to give up when she spotted Bob's profile.

His photo was unpretentious. It seemed more real than the majority of the male profile pics she saw. He did appear to be fit, but did have the typical dad bod. She read his profile and saw that he was 68 years old, but unless his was a much older picture he could easily pass for someone ten years younger. He claimed to enjoy hiking and maybe that's why he appeared so healthy without looking like the body builders who almost lived at the gym.

He said he was a widower and was looking for someone to help chase away the loneliness. He liked reading, and movies, and nature. He even showed a bit of his humor when he claimed to be a plant murderer under the guise of caring for his garden.

He was six feet tall and that fit in nicely with her own five-foot six-inch height.

She liked that he gave no reference to cars, sports teams, or hunting. These she learned are the hobbies of the so-called macho men who are more interested in impressing other men than in being with a woman.

She penned a quick note to his inbox. "I saw your profile and was impressed by your honesty. I too am recently single, but through divorce and not a death. Maybe we can compare notes about how to deal with the loss of a long-time mate."

She hit send and immediately regretted sharing so much personal information with a person she didn't even know, even if she felt like she did. His profile was the first she'd seen in the year she'd been on this dating site that seemed to be someone she might be able to connect with. She only hoped that he would think the same about her.

Her mind jumped head first into her fantasy life with this new man. She had not been with a man for almost four years. Her ex had not touched her for a year before he demanded the divorce. Now her mind had her naked with this new fantasy lover stroking her body near a lake in the mountains. They were outside on top of a sleeping bag.

Bob had been on the dating websites for a couple of months and was beginning to just chalk them up as another failure and glad he hadn't spent any money on these sites, when he saw an email from someone he hadn't contacted. Her name was Sarah and he after reading the very strange email clicked on her profile.

The first thing that Bob noticed was that this Sarah woman was not a twenty-year-old player. She was dressed well, but not like the gold-digging vamps he found at the bars. What she wore was not overly sexy, but did show off her charms. She seemed aware that she was attractive and had no need to flaunt it.

She was 43. She claimed to go to the gym a couple of times a week. She went to a yoga class, Pilates, and a spin class. Bob understood why she looked to be in such good shape after two kids. She shared that she was estranged from her kids and was looking for a friend and maybe a companion. She sounded just as lonely as he felt.

He formulated a response, "Hi Sarah, I'd love to compare notes with you about how to chase away the blues. I've been working on writing a book about all the ways that don't work for about four years now and feel that I'm very close to finding the answers. I read your profile and you seem very active with the gym and I can assume that is why you seem so fit. I personally like breathing the fresh air along a mountain trail. Do you enjoy hiking?"

Sarah hadn't signed out of the dating website when she received the reply from Bob. She laughed as she read the part about the book of things that don't work and knew she had to get to know this man.

"Hi Bob. I also am writing a book of the things that don't work to chase away the loneliness. I think so far, I have enough information for a mini-series. I love the outdoors, but haven't been hiking other than the maintained trails, mostly paved, around the lake. I'd love to go on a hike with you, but I might have to buy some hiking boots. Where do you like to hike? I could probably handle a ten-to-fifteen-mile hike if there weren't too many hills," she replied then waited to see how fast he answered. That would be an indication of his interest. It was already confirmed that they were both desperate.

Bob was impressed at how fast she had answered his email. It seemed to him that they were both ready to get together with another person. He answered her email and shared a few more details about his interest, but nothing too controversial just yet.

Over the next few hours and dozens of emails back and forth they progressed to the subjects most would avoid, but the more they chatted the more comfortable they felt. They shared the details of their childhood, their views on politics, religion, and on if people who put ketchup on hot dogs should be shot. They agreed on almost everything including how long to wait before expecting sex.

"I'm feeling very comfortable with you already and both of us have had plenty of life experiences so I'm not sure we need to wait very long, but we do need to meet first. It might also be a good idea if we knew each other's kinks beforehand. I'm not sure if I want to see your dungeon and be tied up while you flog me on our first date," Sarah replied to the sex question.

Bob laughed out loud as he read her response, "Okay the flogging will wait until the second date, but I did just have the dungeon cleaned," he answered.

Sarah had to respond to that, "I'm glad because a dirty dungeon is a deal breaker for me. LOL"

"I have the maid clean it again just to make sure. I want to make sure to make a good first impression. Kidding aside would you like to meet and see if we like each other in person as much as we seem to online?" he asked.

"I'd like that. I think most first meetings are at a coffee shop, but I actually hate Starbucks and I think that if you leave your axe in the car we can meet for a drink," she offered.

"Deal, how about tomorrow at 7. I told you that I've checking out bars and I found one that is not a meat market. It is a quiet little neighborhood bar," he suggested.

They exchanged information and signed off.

Bob was happier than he'd been in years. This woman was funny, intelligent, any not afraid to try new things. He looked forward to meeting her. He was a bit apprehensive about sex with a strange woman after so many years, but was certain she felt the same. Their sexual joking about the dungeon masked each of their insecurities.

He wondered what to wear for his meeting with Sarah, but remembered that she liked his profile photo and he seemed so down to earth and not like the ego driven men she met on the dating site. He opted for a casual look with slacks and nice shirt.

Sarah could not believe her luck in finding someone like Bob. He was witty and very entertaining. He had similar beliefs as she did and he hid his insecurities behind humor as she did. She knew that the sex talk was just a front and she had to make sure he understood that she was interested. She laid out a casual, yet low cut top that would show enough cleavage to entice him, but not slutty. She could lean forward for that when the time was right. She paired the top with a pair of pants that were just snug enough to indicated there was a woman under them. They were going to a casual bar so there was no need for a skirt.

Sarah arrived at the address Bob had given her and found him by the front door waiting for her. They exchanged greetings and a warm hug. Bob hadn't hugged a woman in quite a while and wasn't sure how long it should last, but this hug seemed long, not that he was complaining. It was just another indication that Sarah might be interested in him as more than just a friend.

Bob escorted her into the bar and directed her towards a table where they could talk. The waitress came over just as they were seated and took their drink order. Bob took out his wallet to pay, but Sarah stopped him.

"I know that you are old school, but I also have money and can pay for my own drinks," she instructed him.

Bob smiled and answered. "I'm not as old as you think and the arguments that the men have to pay and the woman has to put out went away decades ago. Here's the deal, I'll pay for the first round and you can take care of the second," he declared.

"Deal," she said with a smile.

They chatted in much the same way they had on email, but this time each leaned in closer to the other and there was a lot more physical touching of hands and arms. It was all innocent, and not sexual, but it was physical contact.

They spent an hour and a half laughing and sharing information until Sarah announced, "You promised to show me your dungeon. Has the maid had enough time to clean it?"

" Ah... well... the thing is I may have misspoke when I said I'd have the maid clean it...You see I really don't have a maid," he confessed.

"You mean that you have to clean it yourself? Sarah asked.

"Well, you see I'm really not that good at cleaning and actually before I clean the dungeon, I'd have to build one," he announced with his head lowered in mock shame.

"Do you at least have a flogger?" Sarah asked now barely containing her laughter.

"Well, no, but I know where to get one. Amazon has everything," he responded.

Sarah could no longer contain herself and she broke out in laughter. "I enjoy this sexual banter, but we need a serious talk," she then raised her hand to get the waitress's attention and indicated another round. "This one is on me, because we are going to sit her and talk about where we go from here. I'm nervous as hell and I haven't had sex in four years and it's been much longer than that since it's been with anyone other than my husband. I'm sure you have a similar story." She paused as the waitress brought over their drinks and Sarah paid.

Bob waited until the waitress left before responding, "You're right, I'm nervous too. I haven't been with anyone for over four years and for 35 years before that I never even thought of another woman. I'm afraid that I won't know how to be with anyone new."

"I understand that; I feel the same. Sex was never a major part of my marriage. My ex was more interested in his profession than being with me. It wasn't until he left and I got involved with the dating site did I ever even heard that I was attractive, sexy even. Unfortunately, the men who said those things were younger than my sons. The men my age only wanted arm-candy, but they also told me that I was cute enough to impress the other men they wanted to impress--I was nothing more than a fancy new car to them. I'm interested in you and like to move forward, if you're interested." Sarah shared.

"Wow! You had a hard marriage. Sex was good between my wife and I, but we were pretty boring. We experimented when we were younger with some of the sex games: role playing, light spanking, lingerie, and movies. They were fun, but we decided that they were too much work and we just settled for straight boring sex a couple times a week. We were predictable, if not overly passionate." Bob shared.

"I'm also interested in moving forward with you too. You are extremely attractive. I have to confess that over these last four years of sexual starvation, I discovered porn and I not only learned a lot, but developed an addiction. I'm not sure if I ever want to do any of the things I saw, but I did find a lot of things that got me aroused." Bob confessed, red faced.

Sarah's eyes opened wide, "That is why I want to move forward with you. You are the most honest person I've ever met. I've read a few steamy romance novels that got me all hot and bothered. I'll share what turned me on if you share what did it for you. I'm not saying we need to do these things, but I would like to talk about them. I think I'd rather not discuss this topic in public. Can we retire to you place, even if you don't have a dungeon?" she said with a laugh.

They finished their drinks and Bob asked, "Would you like to follow me in your car, or just leave your car here?"

"Would you think it strange if I asked to have my car with me?" Sarah asked.

"Not at all. I actually think that would be the best. I'm not sure how safe this parking lot after the bar closes. I live in a residential area and your car will be safe there," he replied then gave her directions to his house just in case she lost sight of him.

She followed him to his lower middle-class home in his lower middle-class neighborhood. It was so different from the house she and her ex lived in. He had forced the sale of that house and she now lived in a condo.

Bob directed her onto the couch in his living room then asked if she would like a glass of wine.

"I'd love a glass. Is this house you lived in with your wife?" Sarah asked.

When Bob acknowledged that it was, Sarah responded, "It's lovely."

"Thanks," he said handing her a glass of wine. "It has a lot of memories and it might be better if I moved out, but I'm not willing to go thought all the trouble of moving."

"I agree and long as your late wife doesn't haunt you if you bring a woman home. I assume I'm the first woman you've had here since you wife died," she commented.

"You are. I have gone thought my grieving process, and don't expect any problems. My late wife and I talked often about what each of us would do if one of us died. I am following her instructions." He explained.

"Sounds like you are your wife were very progressive. I'm glad. So now how often do you watch porn? I assume you watch the movies online." She asked.

"I do and before I met you online, I was spending a few hours every day watching porn online. Mostly younger women having sex with strangers." Bob admitted. "Tell me about your steamy romance novels."

They shared several details of the things that aroused each of them and when Bob commented that a couple of years ago, he noticed that he found women's feet erotic, Sarah took off her shoes.

The more they talked the closed they moved to each other, the casual touching increased and after the first kiss, Sarah commented on how much she loved to be touched.

Bob stroked her cheeks and down her neck. He progressed to the front of her neck and explored her cleavage.

"Could I have another glass of wine?" Sarah asked.