Not a Sugar Daddy Pt. 02

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The next morning Tadd woke to the sensation of a mouth surrounding his cock. Whether he had morning wood or it was her attention, he was rock hard. He needed to pee but that's impossible with a hard-on so he laid back and enjoyed.

Connie sucked his head and teased his frenulum with her tongue before pushing down, taking him all the way. He felt her tonsils as they passed over his shaft and then his head touched the back of her throat. She held him there a moment and then slowly pulled up, licking his shaft as her lips caressed it.

Connie stopped when she had only his head in her mouth. Her lips surrounded it just below the ridge and the tip of her tongue flicked over his urethra. Pushing it in she managed to open the hole just enough for the very tip of her tongue to enter a tiny bit. That was a completely new sensation for Tadd, who moaned loudly.

She continued working his cock in this fashion, never staying on the head, or driving him into her throat, for too long before reversing course and doing it all over and over again.

"Hon, I'm going to cum," he warned her.

"Mmmm hmmmm" she mumbled around his cock.

A few more strokes and Tadd put his hand on the back of her head. As he felt his explosion starting he drove his cock as far into her mouth and throat as possible. Her lips were at the top of his scrotum as he began shooting.

The first squirt went straight down her throat so Connie pulled up, allowing the rest to hit her mouth and tongue. Finally, as his orgasm began to subside, she pulled up to his head and held just it in her mouth, careful not to let her tongue touch his head.

Connie counted one Mississippi, two Mississippi, three Mississippi, until she reached fifteen and then swirled her tongue around his cock head. Tadd moaned and said, "Oh god!" but didn't push her off or pull out of her.

Connie had never done this before. In fact, until their conversation the night before, she had no idea that men can sometimes have multiple orgasms. Not sure if some special technique was needed, she just continued giving him the same type of blowjob that had made him cum.

Ten minutes later, Tadd knew that as wonderful as this felt, he wasn't going to cum again. "Connie, time to stop. Your jaw must be aching!" he told her.

Connie reluctantly pulled her mouth off his cock, gave the head a little kiss, and looked up at Tadd with a pouty face. "I WILL make you have multiples!" she insisted.

"I'm sure you will, hon, just not today. First thing in the morning may not be the best time to try - I've needed to pee since you woke me. He needs to get soft so I can!"

"Hmmm, you might have a point there, in addition to this point you always have," she said, grasping his cock and squeezing. "Okay, I'll leave you alone to relax. I'm going to let the dogs out and start breakfast. After you drain the snake c'mon down. Coffee should be ready by then."

Standing at the side of the bed, she leaned down and kissed him, long and hard, and then walked out of the room naked.

Tadd's cock was now shrinking rapidly, so he headed to the en suite and emptied his bladder. He knew she wanted him naked so he carefully dried his little head so no dribbling would occur. Then he followed her trail down to the kitchen.

Connie was standing at the counter, slicing vegetables. Tadd walked up behind her, pressed his loins into her ass crack, and reached around with his arms. Starting with her breasts he massaged her. When she started purring he switched to rubbing her nipples between his thumbs and fingers. In no time the purring changed to moans. Leaving his left hand to continue playing with her left breast, he ran his right hand down over her flat stomach and found her pubic hair. Twirling his fingertips through it he was careful to move very close to, but not touch, her clit.

This was incredible torture for Connie, whose moans were now loud enough he briefly wondered if the neighbors could hear. Connie moved her foot slightly to the side, spreading her legs a bit.

Avoiding her clit, Tadd's fingers leapt down to her core. Wiggling it between her ass cheeks, Tadd used his middle finger to play with her asshole. As he had the day before, he ran the pad of his finger around and around her rosebud, which was already lightly lubricated from the wetness that had dripped out of her pussy.

"Please! please!" Connie urged him.

Ever so slowly, Tadd pulled his fingertip north and rubbed up and down over her perineum. As a very sexual being, this excited Connie even more. She was desperate to have him fuck her but knew he hadn't recovered yet from the blowjob. Soft as it was, his cock still felt wonderful between her cheeks, and right then she made a decision that surprised even her.

Tadd moved to her opening and inserted three fingers into her. The intensity of her moans made him wonder if she was already cumming, but he didn't feel the telltale throbbing and squeezing of her pussy that would incite. He fingerfucked her pussy for several minutes and then relented, pulling them out.

Connie gave a disappointed noise that vanished instantly when Tadd took her clit in his fingertips. "Oh my god! Yes! Yes! Please!," she begged him.

With his first two fingers Tadd scribed a circle around her clit again and again. He had seen her touching herself in this manner as she sucked his cock and it clearly worked. It took only a minute or so for her to explode and collapse back against him.

Tadd moved his left hand from her breast to under her right arm, supporting her as she convulsed through her orgasm. Her cum was already dripping down the inside of her thighs, and Tadd cupped his hand under her labia and massaged her gently.

"Good lord, what you do to me!" she said, turning to hug and kiss him, but still relying on his support for her shaky legs.

"Just repaying the favor you did me earlier," Tadd grinned. "I planned to give you multiples but that one seemed to really hit you, so I thought another might be too much."

"Good call. More and you likely would have traded a girlfriend for a wet pile of mush on the kitchen floor!"

"Oh, I have a girlfriend?" he teased.

"Yup! You're stuck with me now!"

Connie resumed making the omelets she had been prepping while letting her body calm down. After they ate, she asked him, "Recovered for round two, yet?"

"I was hard when I was playing with you, babe. Turns me on to see you turned on and cumming," he said.

"Good. Take a seat in the living room and watch some tv or something. I'm going upstairs to freshen up, then I'll be back." Giving him a deep kiss and stroking his cheek, she turned and left.

Tadd flipped the tv on and watch some home improvement show. Forty-five minutes later Connie returned, placing a small something on the side table. "I need fucked, Tadd. Can you do that?" she asked him.

"Absolutely," he replied.

"Just one thing, hon."

"Oh?" he asked, confused. "What would that be?"

"I want you to fuck my ass, please," Connie declared.

"What? I thought that was special occasions only," he said.

"This is a special occasion. One year from today we will be celebrating our One Year Anniversary of being together," she explained.

"Wouldn't that be yesterday?" he asked.

"Nope. We agreed we would get together but either had the right to end it and part friends. You're still here and I'm not going anywhere, so today is the day we officially committed to each other, even if we haven't said it." Her explanation made perfect sense and revealed that she probably had much more depth than he'd seen so far.

"So, will you fuck my ass? I did say please," she grinned.

"It would be my honor and pleasure, my dear," he grinned back. "Do you have lube?" She handed him the item she had put on the side table and he saw it was a bottle of lube. "Kneel down in front of this chair and lay your head, chest, and arms on the seat."

When she was in position, Tadd squirted a liberal amount of the lube on her asshole, and used his finger to make sure some made it inside. He then fully coated his cock with the lube, and then knelt behind her. Placing the head of his cock on her back opening, he pressed just enough so she would know he was there. He was pleasantly surprised to feel her sphincter relax and open just slightly.

"Remember, you are in full control here, hon. If you say stop, I stop. If you say out, I pull out, ok?"

"And what if I say 'faster' or 'harder' or 'deeper'," she said with a teasing tone to her voice.

"Then I shall attempt to fuck your ass faster, harder, and deeper!"

"Perfect! I'm ready for you to enter. It has been years so we'll have to take it slow until I get accustomed to it again. I trust you," she told him.

Tadd pressed forward with more force. Connie concentrated on intentionally relaxing her muscle. Soon the head of his cock popped through her sphincter and she immediately called "Stop! I need a minute to get used to the feeling," she told him.

He had stopped instantly when she said the word. Her muscle had a tight grip on his cock and he desperately wanted to keep going but knew this had to be at her pace.

"Ok, hon. Go slow but push in deeper," Connie told him. He did as she asked and when he felt his cock was about halfway in she again called "Stop", although with less urgency this time. She knew now that he would comply instantly.

Connie focused on slowing her breathing and taking more natural breaths, rather than the deep breathing she had been doing. It was only a minute or two before she told him to keep going.

Maintaining a slow pace, Tadd pushed in further. It wasn't long before his crotch was pressed firmly against her ass cheeks. He was fully inside her.

Connie realized this as well and said, "Just stay right there for a bit. You've probably heard this before but I have an incredible feeling of fullness. Impossible to explain but it kinda feels like your cock is also fucking my stomach. You're a good size but not that long, sorry hon!"

"Babe, your ass feels incredible. Much different than your incredible pussy, in a good way. Ass, mouth, and pussy all give me extreme pleasure but in different ways."

"You'll have to explain that sometime but right now I'm ready for you to start fucking. Let's start slow and gradually increase your pace. I'll let you know what I want," she told him.

Tadd withdrew at the same slow speed he had gone into her, and then pushed back in just a hair faster. Her moan, groans, and mumbled curses told him she was enjoying this a great deal. He kept speeding up, expecting her to call out 'not so fast' at any time. Instead she cried 'faster, harder, deeper'!

Pumping as fast as his old hips would move he pounded her as hard as he could. "That's all there is, hon. I can't get any deeper!" he apologized.

"When you slam me that hard it feels deeper," she replied.

Tadd was holding himself back, not wanting to cum too soon. He hoped she could cum from this, but realized he'd stupidly not asked her. Almost ten minutes later he felt like he was about to burst when she said "I'm going to cum, hon! Oh god, I'm cumming! I'm cumming!"

Her hips began bucking and she was actively trying to fuck him with her ass. Her muscle was clenching and unclenching around his shaft. She pushed back so hard he was afraid his cock would fuck her stomach. It was all too much for him and without a word he shot his cum into her ass, again and again.

"Oh my god! Did you just cum? Did you cum in my ass? That feels incredible!"

"Don't move, please hon. I need to rest and my cock needs a break. Just let your ass hold me," he asked her.

Five minutes later he softened and shrank. When the head of his cock was back at her sphincter, it spit him out. He pushed against the chair seat to help him stand as she raised her upper body, but remained kneeling. "I'm going to clean up, hon. I'll bring you a washcloth," he said.

"Not yet. Come sit down here," she said, patting the chair seat. Curious, he sat on the protective towel that was still warm from her face and arms.

As soon as he had, she shocked him by taking his cock in her mouth. As he was soft she had no trouble taking the entire thing in, and even managed to add one of his balls. A few moments later she exchanged it for the other ball. Connie set about to clean his cock as thoroughly as she could. Finished, she pulled off him and looked up, grinning.

"Well that was a shocker," Tadd said. "Never had anyone go ATM with me."

Connie smiled broadly. "Good! I've never done that with anyone else. I like us having things we've only done with each other." At that she stood, leaned over him and kissed him. "How's it taste?"

"A little musky, I'd say, but not repulsive."

"I gave myself three enigmas when I went upstairs. On the first a small amount of dark material came out. The second appeared to be as clean as the water that had gone in but I did a third just to be sure. Seems like it worked!"

"Do you plan to make a regular habit of that?" Tadd asked.

"The anal, definitely. ATM, probably not every time, but when the mood strikes I will. That work for you?"

"One request. Next time you decide to go down on me after, let me know right after I cum. I'd like to pull out and still have some erection when you do it," he said.

"Deal. How about a shower? We both got pretty sweaty," she asked.

When they'd cleaned up and dried off, they went back downstairs, still naked. "What time do you have to leave?" she asked him.

"Well, it's noon, so why don't we go into town, get something to eat, and do some window shopping. I'd like to hit the road by four so I can rustle something up for dinner at home. No Chinese delivery at the cabin!"

"I have another idea. I cleared my calendar through Thursday. Could I follow you down and spend the next four days with you, at your place?" she asked, fingers crossed that he would say yes and that he wouldn't think it was too fast.

"Well, I would have to put some conditions on that," he replied.

"Conditions? What kind of conditions?"

"I want to cum with you at least twice every day. And you have to cum even more than that!" he answered.

"I think I can manage that," she said with a smirk.

"Okay, so let's get some lunch and skip the window shopping. We can head out early and get down there in time to get settled before we have to figure out dinner."

They reluctantly got dressed and Connie took him to a sandwich shop she liked. Back at her house they both packed up and loaded both dogs into the backseat of her SUV, which was covered with a seat protector. The dogs had gotten along famously and Tadd only hoped it would continue when they were back on 'Tess's Turf'. He put both crates in the back of his pickup with their food and water dishes and food inside and gave her his full address to put into her map program in case they got separated. They kissed then headed out.

Two hours and fifteen minutes later they pulled into his long, steep driveway. He hit the remote and pulled into the garage once the door was fully open. He got out and indicated where Connie should park, then grabbed the two crates and put them in front of the cabin door. He went back to his truck and retrieved his overnight bag.

Once she was parked where he had pointed, Connie got out and unhooked both dogs from the leashes they had been on, to keep them from jumping into the front seat. Once freed, each dog jumped out and Tess bounded around the side of the garage to visit her favorite forest trail, with Butch following closely behind.

"Tadd, it's even better than the pictures you have on your dating profile! I love this. I can't wait to retire so we can live here all the time!

Tadd didn't let her know that he'd already thought about moving in with her, since they'd had less than thirty-six hours together. 'Best to wait till Thursday to start that conversation,' he thought.

Once inside he showed her around and indicated where she could unpack her bag. "Do you have extra towels? We should cover the upholstered furniture since things have a tendency to get wet around us," she said.

"Things? More like your Trevi Fountain of a pussy!" he teased. "But yes, I have a couple of beach towels and some bath towels we can use."

Tadd checked his freezer inventory and told her, "I make up batches of some dinners so I only cook once and eat four times. I can pull Egg Roll Bowls, Fish Burgers, or Chicken Burritos out of the freezer and we can defrost then heat them up in the microwave. What sounds good?"

"What's an Egg Roll Bowl?"

"Ground pork, carrot, garlic, onion, cabbage and a bunch of Chinese sauces and spices. Tastes very much like an egg roll but without the unhealthy deep-fried wrapper," he explained.

"Sounds delicious, and not too filling," she said, winking.

"You're incorrigible," he replied. "Let me ask you a question. When this honeymoon phase is over, and if we were living together, how often would we have sex?"

"For the most part, I would hope at least once a day. Sometimes my work might get in the way of that, but on days off we can make up for lost sex. What do you think?"

"I think that would be great, provided I can keep up with you," he answered.

"You've done a great job so far!"

He climbed the stairs to the loft and took two servings of the Egg Roll Bowls down to start thawing on the counter. He heard Tess as she jumped up and smacked the dining room window with her paws. Seeing the questioning look on her face, he told Connie, "That's how Tess let's me know she wants in. Learned it at her first home, before I adopted her at 18 months. By then a habit is engrained."

She asked where the towels were and he directed her to the linen closet in the master bath. She returned and covered the sofa with two beach towels and the rocker/recliner and armchair with big bath towels.

"So, how many asses have you fucked with her bent over this chair? I know you like that position for anal," she asked.

Tadd laughed. "Actually only one, although I had that one a few times there."

"Tadd," she said with exasperation in her voice, "By now you must know that I require full disclosure and details. What counts as 'a few times'?"

"Best I can recall, maybe three or four. Remember, I"m old. My memory isn't what it once was," he told her.

"Okay, I'll claim possession of the anal chair after we do it five times there," she declared.

"Perhaps I'll have a plaque made up. 'On this chair, Connie has taken it up her ass more than any other woman'"

She slapped his bicep, playfully. "If you're going to start getting plaques, find a place that offers volume discounts. I plan to break every record in your sexual history.

Connie continued, "We're both very over-dressed. Strip down stud. I assume we don't have to worry about the neighbors peeking in?"

"Nope. Tess will warn us if anyone drives up and it's rare for the neighbors below to walk up. Only happens when their dog gets off his leash and heads this way," he told her.

Once naked, he asked her, "Have you ever gone to a nude or clothing optional beach or resort?"

"I did go to Hedonism II once. They have both optional and fully nude beaches, in a restricted, guest-only resort. It's also all-inclusive which is great."

"Yes, I went to Sandal's in Montego Bay once. I loved the open bars, all-inclusive arrangement. But they aren't nude or optional," he said. "Did you enjoy Hedonism?"

"I loved the resort but the guy I went with was a complete dud. We were there for a week and I think we fucked once. Two of the threesomes I've had were there, when I got frustrated with him and let a couple pick me up."

Tadd was silent, imagining the scenario when she interrupted, "TMI? Does hearing about my past sex life bother you?"