Not a Sugar Daddy

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Despite being on a couple of dating sites, he was finding it difficult to connect with a potential partner. Being 70 years old was certainly an issue, and living in a very rural area was another. He'd set his parameters for a potential partner at 58 to 75 years old, but the pickings were pretty slim. He was of average looks, certainly not movie star material, and he expected only the same in return. But many women in his age range looked to have spent far too much time in the sun, or were former or current smokers, whose wrinkles made them look much older than their claimed age. He was often told he looked at least ten years younger than he was.

So he was surprised when he started getting a large number of views from women in between 40 and 55. Many of these were likely curiosity seekers, who clicked on his profile after reading one of his blog posts. But, as he viewed them in return, he noticed a number who had listed their match as being between 60 and 75. Gold diggers looking for a sugar daddy he concluded. Especially since most of these were not paying members and thus could not initiate messages.

Then one day he opened his mail program to find a notification from the site saying that he had a DM from ConfidentLady. Clicking the link in the email took him to his account and the Messages page. There he saw the message from ConfidentLady:

"Hi Ollegio, I'm Connie. I absolutely love your profile, and all your pictures. I can tell some are older, where you were sharing some things you enjoy doing such as hiking. But I'm betting your primary photo is recent and I must say you don't look your age. I know I'm younger than you're looking for but I hope you'll give me a chance and let us get to know one another. I think it just might be right for both."

Connie's profile indicated she was 48, never married, no children. She claimed to be gainfully employed in real estate and lived in the next state north, about two hours from him. She was also very attractive in a girl next door kind of way. Not a model and thus not out of his league, but certainly someone he'd be proud to have on his arm.

He neither wanted to seem eager nor rush into something too quickly so he decided to let it percolate for a day. If, after thinking it through, he decided to respond, he would do so tomorrow. In the meantime he made himself breakfast then left for the gym, after which he did his week's grocery shopping.

After returning home and putting away the groceries he made lunch and ate. Then he logged back on to the dating site, reread Connie's message and looked at her profile and pics again. He noticed she had looked at his a total of three times at this point.

The next morning he logged on and found another notification in his email. He had received a DM from FortyandFoxy on the same site. He clicked the link and read:

"Hey sexy! You're profile makes my pussy wet! I NEED you to message me back! We could be so hot together!"

The lack of a real name and the over the top come on were dead giveaways to a scam, so he clicked Delete and opened Connie's message. Hitting Reply he typed "Hi Connie. You have a very interesting profile and nice pics. I'm a bit skeptical given the age difference. I'm prepared to, as Coleridge said, willfully suspend disbelief so we can message and, hopefully, get to know one another. Tadd."

Within the hour his email program pinged and he saw another message had been sent by ConfidentLady. He clicked on the link and went to the DM.

"Hi Tadd. I can understand your hesitancy. Yes, I'm 22 years younger than you. You probably think I'm a gold digger looking for a sugar daddy, but I promise that is far from the truth. I'm a real estate agent and very good at my job. I make over $200k per year, so I'm not after your money. I find you extremely attractive both physically and in what you've written in your profile. You are clearly very intelligent and I'm a sapiophile. I also love the pics of your cabin and the secluded, tree filled property you own. Finally (for now) I'm fed up with the immaturity of men my age. Let's get to know one another - my phone number is 555-400-0000. Please text or call. Thanks! Connie"

Tadd read the message three times, searching in vain for any signs of deceptiveness. Still uncertain, he pushed down his doubts and grabbed his phone. Punching her number into his message app he texted, 'Hi Connie. It's Tadd. I'm not ready to talk now but perhaps this evening we can connect. Thanks.' A minute later she replied 'Can't wait! Thanks and have a great day!'

He went to the gym for his workout and the 25 minute drive, hour and a half exercise, and drive back home were all consumed with his thoughts of Connie. The part of his thoughts driven by his little head couldn't help but wonder what her body would look like naked. From her pics and description she seemed to be exactly his type, but he longed to run his hand over her breast and down her stomach to her pussy and feel the smoothness of her skin, the tautness of her nipples, and the moisture of her most intimate place.

His big head wondered if 22 years was too large a gap. He was 10 when JFK was assassinated and clearly remembered the hasty assembly called by the elementary school to give us the news and send us home early. Her parents wouldn't even conceive her for 12 more years. A year later he'd gone in with his older brother to buy Meet the Beatles, their first studio album released in the US. He still remembered the pandemonium that greeted the band at the airport in NYC and at their tour stops.

She still wasn't born when his draft lottery number for Vietnam came up 66, a year after they called up everyone with a number up to 170. He'd gone on a three day marijuana and booze filled bender he still couldn't remember, finally relieved months later when the US pulled out of the war. What would they have to talk about?

He realized he was driving himself crazy with all this and forcibly pushed it out of his mind as he made lunch, cleaned up, and then dusted and vacuumed his cabin. At five o'clock he texted her again. 'What's a good time to talk? I'd prefer to do phone if you're okay with that.'

Ten minutes later she still hadn't responded and he again began to think this must be a scam. Then his phone rang and he looked down to see her number in the caller id. "Hello?" he said.

"Tadd! It's Connie! I'm sorry, I was in the shower when you texted! As soon as I got out and dried off I saw your message and immediately called. So you're talking to a naked lady siting on a damp bath towel on her sofa." she laughed and then said, "Ok, that was probably TMI but true!"

"Damn," Tadd replied, "Now I wish I'd facetimed you instead!" He hoped that wasn't too much this early.

Connie laughed and said, "Hopefully we'll get to that at some point. So, how are you?"

"I'm good but confused. You're a beautiful, successful, young woman in your prime. What in the world could you possibly see in me?" Tadd asked.

"It's just as I said in my DMs. I'm attracted to intelligent people and I like maturity. I'm tired of the games men my age play. You seem to be financially secure while many guys my age want me because of my income. And something tells me that if we get together I'll never have to worry about you cheating on me. You don't seem the type.

"I know this is the first time we've spoken but I hope you're okay if we skip the bullshit small talk. I don't care what you did for a living and so on. I'd rather jump right to the good stuff," Connie declared.

"Ummm, okay, I guess. Just what do you consider the good stuff?" he asked.

"Sex, of course! How would you describe your libido? High, Low, Medium?" Connie asked.

"Well, a lot of that depends on the relationship and my partner. Best case scenario, I'd say Medium-High."

"Cool! I agree, if we don't turn each other on and make it a priority, it just dies. Speaking of dying, how often do you take the little blue pills?"

"So far, never. Little Tadd only needs the attention of a beautiful woman to stand up and be recognized," he told her.

Connie laughed and said "Great! You're one of the lucky ones. And hopefully I'll be one of the lucky ladies! Next question, how wild do you get with sex?"

"Hmmm," Tadd muttered, "I would call myself adventurous but not overly kinky. I'm pretty open to a lot of things, but definitely have my limits."

"Say more, please. I need specifics."

"I have no interest in scat or watergames. I'm okay with light bondage but won't inflict serious pain on my partner nor do I want it done to me. I won't fuck her face or do anything else that is demeaning or abusive, although I love a good blowjob with her in control," he said.

"We're very much on the same wavelength. Anal?" Connie asked.

"That's always the recipients call. Yes, I enjoy it as long as she does."

"You'll be happy to know she does, but it's a special occasion thing for her."

"There's one important thing you need to know. I had the big snip ten years ago. If you want kids I'm not your sperm donor," Tadd told her.

"Great! I can go off the pill with no worries!" Connie exclaimed. "Okay, enough Q&A, I want to meet, in person, face to face etc."

Tad chuckled, "I certainly admire your enthusiasm. And you have an infectious personality. I'd love to meet in person any time that works for you, and me. My best day is Thursday but I can also do Monday, Tuesday, or Friday in the afternoon."

"We're about two hours apart so if we meet in the middle it shouldn't be too difficult. My calendar is clear for Thursday and that's the day after tomorrow, so how about lunch?" she asked.

"Works for me. Where?"

"I'll text you the name and address of a restaurant I know that's about half way for both of us. Thank you for giving us a chance, Tadd! I know it will be so worth it for both of us!"

The next morning he got a text from her and added the name and address of the restaurant she had sent into his GPS. Then he headed out to his volunteer day at Habitat.

When he got home he tossed his work clothes in the washing machine and took a shower. Then he fixed a drink and started dinner.

Thursday morning he woke up, peed, weighed himself and then fed his dog. He took his blood pressure as he did every morning and then took the pills he'd been prescribed since his coronary artery blockage had been corrected with two stents. He read the news online, did a game of Wordle, and killed some time. Checking the clock he headed to the bathroom and shaved, then jumped into the shower. Afterwards he dried off and dressed carefully, not expecting anything to happen today but wanting to be prepared just in case.

Cleaned up and as ready as he would be, he got into his Mini and started the drive to the restaurant. Once again his thoughts were consumed with what might possibly happen with Connie.

Arriving at the restaurant his heart fluttered from the excitement and anticipation of what might happen next. He exited the car and walked into the restaurant. Scanning the tables he saw her, in the most discrete table in the back corner. She saw him at the same time and waved, smiling.

When he approached the table she rose and, moving toward him, wrapped her arms around him and gave him a deep kiss, frenching him. He responded, and their tongues waltzed in her mouth.

"Wow! That's quite a first welcome!" Tadd told her.

"You ain't seen nuthin' yet, babe!" Connie said with a grin.

The waiter approached and they ordered their meals. Most of the conversation over lunch was fairly mild although clearly laced with much sexual innuendo. When they'd finished and Tadd had paid the bill, Connie insisted they sit in her SUV to chat, as it was much roomier than his Mini.

"So, Tadd, I hope you remember that in my dating profile I say that I'm very direct," Connie said.

"I do remember that, Connie."

"Good. I want you. I want to make love with you. I want to have sex with you. I want to fuck you, suck you and have you every way possible."

"Well that certainly is direct! I'm very turned on by you, and I'm totally up for it on one condition. If either of us isn't into it and doesn't want to continue, no hard feelings. We part as friends, right?"

"Always, but you need to know, that's the last outcome I want. I intend to do everything I can to make you fall desperately for me so we spend the rest of our lives together!

"I have a couple of showings Saturday morning but if you can be at my place around noon we can have the rest of the day plus all of Sunday until you need to head home. Bring Tess so you don't have to find a place to board her. Our dogs need to get along just like us!" Connie finished.

Saturday morning he packed an overnight bag and loaded Tess' crate, food, and treats into his truck. Clipping her into the backseat leash he slid into the driver's seat and they headed north.

A little over two hours later they pulled into Connie's driveway. Leaving Tess in the truck he rang her doorbell. Moments later she answered. As the door swung open he saw she wore only a sheer baby doll and see through panties and bra beneath.

They kissed French and he caressed her ass as they did. She rubbed her tits against his chest and fondled his cock through his pants. Then they broke apart and both headed to his truck to get Tess and his bags.

'Shit! She's nearly naked and walking without a care down her sidewalk to help me unload! I guess she doesn't care what the neighbors think!' he thought.

Once in the house they stowed his bags, introduced Tess to her dog, and sent both of them out to the fenced back yard. Then she stripped him down until he was naked and shed the few pieces she was wearing. "We're going to be naked as long as you're here, unless we go out to eat or something." He looked around and saw that she'd put towels on the sofa and all armchairs so they didn't have to worry about staining them.

His initial embarrassment about being stripped naked by a virtual stranger dissipated quickly as she grasped and fondled his cock. Once she had him fully hard she dropped to her knees and took him into her mouth.

'Oh god,' he thought to himself, "this may be the best blowjob I've had in years!'

Connie played his cock like a virtuoso would play a flute. She thrust her mouth down over it and took him into her throat, deep. She pulled back out and suckled his head relentlessly. She probed his pee and cum hole with the tip of her tongue, and stroked him with her hand as she sucked up and down. She occasionally fondled his balls, sometimes squeezing them firmly but not to the point of pain. Finally too much for him to bear he shot his cum into her mouth, which she swallowed with ease.

Pulling her mouth off his organ, Connie looked up at him, smiling. "That's just a preview of the main events to cum, hon. I intend to rock your world every way possible, if you'll let me."

"Connie, that was definitely in the top three blowjobs I've ever had. Given that that spans about fifty years, it's pretty exclusive territory."

"I want to know about the other two cause I plan to take over Number 1!"

"Hon, we need to talk. I really like you, but I'm worried about our age difference. Do you really, really want to be with a guy as old as me?"

"No, Tadd. I wish you were 50 and still who you are. But I've dated 50 year old guys and they don't have what you do. Hell, half of them need Viagra to get it up! And that takes an hour to work! When I want to fuck I want to fuck, not wait an hour. And the other half are on some kind of macho trip and treat women like possessions.

"I'm crazy about the person you are, Tadd, not the age you are. And I fully expect to be in love with you very soon. The big question is can you get over the age difference?"

"Okay, that's fair. To be honest, I'm worried that at some point you will decide you want a younger man and you'll cheat on me. Been there, done that. Don't want it again."

"I get that. So here's my promise: I will never cheat on you. If I ever reach the point where I want someone else I will tell you and we can talk about it and come up with a solution both of us can be okay with. Will that work?"

"Yes, thank you," Tadd said.

"Now tell me about those other blowjobs. Start talking, dude!"

"Well, the former number two just got downgraded to three, thanks to you. It was a basic bj although she did do deep throat. It was the first time I felt the sensation of hitting the back of a woman's throat with my cock. But what really made it special was that she read my body like it was a flashing neon sign. Every time I got close to cumming she backed off. She edged me again and again for at least half an hour. That was longer than any other bj I'd had and I marveled at her ability to take it that long without her jaw locking up. When she finally finished me off I literally exploded in her mouth and down her throat," he explained.

"And I just knocked that out of second place? Damn, I must be better than I think I am! Okay, what am I up against for first?"

"That one is a bit more challenging. It was the first time she and I had been together in a sexual way. Her former boyfriend was very under-endowed, as in roughly the size of your middle finger." This caused her to raise an eyebrow in disbelief, but she didn't interrupt. "I'm not kidding, she swore it was that small. So for the longest time he refused to fuck her, probably afraid he wouldn't satisfy her. She was a virgin at the time and desperate to have her cherry popped. He eventually did and then she dumped him.

"But apparently all those blowjobs had made her quite proficient at that act. You know how a guy gets supersensitive, especially the head, right after cumming?"

"Women too, my clit becomes a hair trigger after I cum!"

"Right. Well, even though it was the first, and would be the last, time she blew me, somehow she knew how to use it to her advantage. When I came she swallowed and held me in her mouth, careful not to touch the head, for probably 15 or 20 seconds. The painful part of the sensitivity had ended by then but it was still sensitive and she just went back to sucking me. She kept it up until I came a second time, albeit dry. I have no idea how she knew she could start again without hurting me."

"Wow! Have you ever had multiple orgasm again?" she asked.

"Twice more, but from vaginal, not oral," he told her.

"Okay! I'm going to figure out how to do that and since, once I do, I can give you multiples over and over, I'll be in first place! You're not still in touch with her, are you? Wouldn't want her to learn about it and come back to reclaim her title!"

Taking her in his arms he ran his hand over her back and down to her ass, caressing each check tenderly. Wanting every millimeter of her flesh he ran his fingertips up her butt crack and then back down until he found her rosebud. She moaned when he caressed it and then he slid down to kneel on the floor in front of the sofa she sat on. Pulling her to the edge, he kissed her wet pussy and then licked from her ass up her slit to her clit. He paused to take it between his lips and flick his tongue back and forth across it, causing her to moan and arch her hips up.

He moved back down and searched out her opening. When he reached it he tongue-fucked her, driving it as far in as he could and then licking up and out. Sliding his hands under her ass cheeks he lifted her off the sofa until he could easily rim her ass. She began to moan continuously which encouraged him to test the limits.

Slipping his fingers into her pussy he lubed them with her juices. Then he used his wet fingertip to circle her rear opening. She lifted her ass up and moved it side to side, accentuating his actions. When he put the tip of his finger right on her asshole she pushed down against him. Taking this as consent, he pushed back, and his finger slipped into her ass. Without going in deep he stroked in and out, perhaps an inch. Taking her clit back between his lips and tonguing it while fingerfucking her ass brought her to a tremendous orgasm.