Dolly Pt. 03

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Dolly decides to take Dan on an adventure in Cougar Town.
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Part 3 of the 9 part series

Updated 06/07/2023
Created 07/22/2015
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Dan was getting to work late but no one seemed to matter. The last three weeks he had been more productive than ever. His activity was up, his mood was better, and his sales were up. His boss was happy with him. He was actually drinking less too. He had started to put on some weight but had started walking and not just home from the bar.

The only negative he had come across so far was that Stephanie wasn't talking to him. She would be friendly enough. She said "Hi" when he passed her in the hallway on the way to the bathroom but he couldn't help but feel like she wasn't pleased with his relationship with Dolly.

He saw Dolly nearly every day. He didn't know what to call their relationship. They didn't sit and talk; they didn't watch movies or go out. He would come home from work, wait for her to call, and then meet her. Her new thing was to show up at his house wearing nothing but an oversized T-shirt and lingerie. He had never had anything so arouse him as her plump little round body wrapped in scraps of lace and satin. Occasionally she would have him over and he would walk into her place to find her in leather and chains and he would know he was in for it. He had tried tying her down but she was better as the dom.

Laying in bed having screwed and sucked and worn themselves out she was eating ice cream and he was running his fingers over her tits and belly. "So, I don't know what you'd think of it but would you like to go to a party this weekend?"

"Sure." She should have known that if she let him lie there and stroke her fat thighs and giant round tits he would agree to pretty much anything. "I don't know if I can keep up with the twenty-something crowd though."

"Yeah, so, here's the thing. They actually, well most of them anyway, they are older. Go soft." He had started stroking her pussy; it was still wet from fucking. "Not all of them, but, most of them." She had set her ice cream down and was breathing heavily.

"Friends from work?"

"No..." he had slid his finger inside of her and was working it slowly in and out. "Laurie and I went to school together. She's the one, she and I..." Dolly was distracted.

"Was she your girlfriend?"

"Yes..." Dolly whispered. "She has a kid now, and the Daddy, they have these friends. You are going to make me come again."

"We can't have that." He turned her on the bed and spread her legs; he ran his lips down her thigh and kissed the little mound of flesh between her pussy and her leg.

"Oh god. You are so good at that." He ran his tongue along her lips. She was sticky and salty. He hated that he loved her dirty little fat pussy so much.

"Is this some sort of sex party?" he buried his tongue in her.

She moaned before answering, her words were broken between her typical squeaks. "They are kind of freaks. His mom... Her friends... Laurie wants me to go... She wants me to... Kevin, her boyfriend... Oh fuck, slower... You will like them..." He felt her pussy tighten on his finger and he licked her clit quickly making her come. She moaned and pulled his head into the gap between her chubby little thighs.

What the fuck, he thought. Mother and son swingers were the type of Florida shit he ran into that made him wish he were back in SoCal. Still, he liked the idea of watching his plump little girlfriend with another woman.

Grayson's Pub was the type of neighborhood sports bar that had kids menus and good cheeseburgers and lots of TV's that reminded Dan of when he was married with children and would go to a place just like this on Fridays with the family. It wasn't overly packed on a Saturday evening and he and Dolly took seats at the corner of the bar. The bartender brought beers and a dish of nuts.

Dolly looked particularly good tonight. She had worn a little sundress that was black with little cherries on it and bright red heels. She called it her Rockabilly-Swing outfit. He grinned at the name and wondered if she realized. She hadn't and they both giggled. He knew the moment the tall blonde walked it that she was Dolly's former lover. She was tall and over the top. She wore a thick shellac of makeup, bright red skintight pants and a cheetah print top that barely held her large breasts. Her lips were broad and painted bright pink and she greeted Dolly with a prolonged kiss that sent them both to the ladies room to repair their lip-gloss. Dan was happy he'd chosen jeans tonight as the embrace had given him instant wood.

Travis was a nice enough kid. He was short and pale and seemed the exact opposite of his girlfriend. He was snarky and Dan appreciated his dry sense of humor as he mocked the girls then turned on the bartender with a quick Jibe. The bartender appeared to be the owner and Travis introduced them.

"I hear you two are coming over tonight. You like wine?"

"Sure." Dan answered.

"That's good. There will be lots of wine."

Dan drank his beer slowly. He talked to the kid for a while. He talked to the bartender. They seemed decent enough. Dolly had told him they were a highbrow crowd but he still expected mobile homes and cases of Budweiser. At seven the bartender passed the bar over to a tall cute redhead and they wandered out. It was apparently a short walk but Dan had his car. Laurie and Travis piled into the small backseat and directed him around the corner to a cul-de-sac of nice single level stucco ranches. He parked and followed the girls to the large white house at the end. Laurie had already reached under Dolly's skirt to grab her ass.

Florida is a hothouse of swinger activity. In his fifteen years here he had been invited to parties several times. He and his wife had frequently met couples through the kids school or through work who would get a couple of drinks in them and try to get them into the Jacuzzi. Dan was typically too possessive to understand the allure. His wife, who seldom broke out of the missionary position quickie routine found the idea appalling. Dan had started to develop some affection for Dolly but she had put it out there pretty clearly that they were fuck buddies and that was about it. He found that a little comforting, as he couldn't figure out what kind of relationship he could have with the round little sexual freak.

"So, I'm sure Dolly told you about my mom's friends, right?" Travis asked as they crossed the asphalt heading to the house.

"She said there was lots of wine and that, well, things happen."

"'Things happen. ' That is a bit of an understatement." The girls ahead of them were giggling and playing grab ass. "Have you ever been to a party like this?"

"Um... I've been invited, I've never gone."

"Okay, so I guess I will just let you in on a couple of things... No means No and the girls are in charge. Don't worry though, the girls don't really say no. You are going to meet my mom, Jules. I think she is going to like you. I just kind of ask, don't go getting all down with her while I am like, sitting there. This is kind of weird enough as it is."

"I was wondering."

"Yeah, I know, eww, right? I just kind of slip outside or outback when things start getting, you know... "

"Okay, so be careful of Jules. No means no. I will probably just lay low, this is really for Dolly."

"Laurie has wanted Dolly to come over for a while. She found out about you and the game was on."

"Me? What did I do so special?"

"Do you remember Ellie Torrez?"

"Kind of." He ran the name through his head. It took a minute but he got it. "She was the attorney at my old company when I started there. I know her. It's been at least ten years though." She was cute. A bitch and a half, but good looking.

"Yeah, well, she remembers you. I don't know if you are going to get to lay all that low for very long."

Dan and Travis followed the girls into the house and down a short hallway to the Kitchen. Grayson, the bartender from the pub greeted them with glasses of a nice red. Dan, in his best effort to be polite mentioned how nice it was and asked what they were drinking. The skinny brunette wrapped in a towel giggled and asked if it mattered. She was sitting on the lap and a short older Hispanic guy. He also appeared to have nothing but a towel wrapped around him. After they giggled she turned and kissed him in the prolonged wet sloppy way that Dolly liked. The small man groped at her until her towel slipped down revealing a nice pair of breasts that, considering her almost bony build had to be implants. Dan was appreciating them as Dolly and Laurie continued to paw at each other.

Dan was nearing sensory overload when Grayson leaned in to warn him. "Oh shit. Prepare yourself."

"So you are the old guy now, are you." Came a familiar voice from behind him. He turned in time to greet the sandy haired woman he had known at his old job. She was tall and attractive. She wore a black crochet swimsuit cover-up, little heeled sandals, and nothing else. He admired her body through the thousands of small holes. "I never figured you for a chubby chaser." He remembered her snarkiness. "Think you can still get it up for a woman your age or are you gonna scurry off with Jellybean?"

"Hi Ellie." He smiled at her. He could get it up for her he figured. "It's been a while."

"Yeah it has. You got fat." Her dig was somewhat softened by her hand slipping around him and the proximity of her face to his.

Fuck it, he figured. "I don't really go for cougars these days but I'd hate to be a bad guest." He wrapped his arm around her and their mutual groped formed a bit of a pretzel. He could have set his wine down but it really was a nice Malbec. His hand found her ass. It was round but firm, nothing at all like his new girlfriends. He kissed her and she kissed back. He kissed her more deeply, testing her lips with his tongue and she joined him. He took a deep breath as they embraced and relaxed. She ran her free hand over his arm and moved her bare leg up the side of his jeans. He wished he had worn shorts.

"Old guy can stay. Why am I the only one without wine?" she said. Grayson provided her a glass. "Jesus, those are giant tits." She said pointing out Dolly's chest. Travis, don't let one of those hit you, you'll be down the count."

"I know!" Exclaimed the mom. So fucking weird. "I just want to curl up in them and take a nap!" she said, reaching out and grabbing Dolly's left breast through her dress. "Are we swimming?"

"I didn't like, bring a suit?" Dolly said

The group of them giggled. Andy, the little Hispanic guy let the skinny mom out of the kitchen to the back yard.

"Why don't you just stay in there with me and Trav'" suggested the big blonde to Dolly. Dan was fairly impressed by the subtleness of the separation of the Mother and son before anything freaky went down. It was going to be a weird fucking night.

"You coming with us, old guy."

"Fuck yeah, he is." Spouted out Ellie. He couldn't help but like the attention. The more he looked at her, the more he appreciated her body beneath the lacey wrap, the more he started to question the whole Dolly thing. It certainly wasn't something to ponder at the moment. Grayson had pulled off his T-shirt and tossed it aside to a couch in the connected living room. Ellie drug him by the hand to the patio door. He admired her ass as they walked and found himself dwelling on their kiss and how much he wanted another one.

Grayson stood at a small bar on the patio. He had stripped down and his abs and shoulders had Dan feeling a little self-conscience. The Bartender transferred all the wine into small acrylic stemless glasses, each with a caricature painted on them. Dan watched Ellie pull the cover-up over her head and admired her long lean body. She had to be near fifty and she didn't look it in the least. Her ass was a little soft and he had a belly, probably from having a kid, but she looked spectacular.

Andy emerged from the water, a round tan hairy little ball of man. It made Dan feel better and he went ahead and stripped off his jeans and boxer briefs.

"He may not have my Grayson's ass but damn Ellie, how do you take that cock every night?" Dan had the feeling the mom was pretty loaded already. Her comment though drew his attention and indeed, the little man had an impressive schlong. Swingers, man. He thought. Fucking nut jobs. He carried Ellie's drink to her. Hot fucking nut jobs at least. He handed her the wine and turned and dove into the pool, slipping quickly under the water to the far end where it got deep. He let the cool water chase some of the booze out of his head before emerging. He came out of the water with the mom hanging on to one of those rubber floating noodles right beside him.

"How are you doing there, old dude?"

"I'm good. How are you?" She was really very pretty. He wasn't really into the super skinny middle-aged women, he thought it made them look older but she did have lovely little breasts and they were floating right at his chin.

"I feel good. Here, feel." She wrapped her legs around his waist. He could just touch bottom. "Damn, you feel pretty good too." Her thigh was pressed against his hard-on. "Ellie, if you still want dibs, you better get over here." She pulled herself against him and let go of the noodle letting it shoot out across the pool.

"Wanna play with my tits?" she asked.

"Um, sure." Fucking nut jobs he thought, taking her perky small nipple in his mouth.

"Harder." She encouraged him, pulling his head to her chest. "Yeah. Like that." She said as he pulled the small nipple between his teeth. "Don't let her use you up before I get some." She said. Ellie was sitting on the steps and called out to them that she was lonely. He worked his way back across the pool, dipping briefly under water as he crossed the deepest part. Jules moaned and he switched tits, he felt his cock pressed up against and actually did begin to worry about getting used up.

Dan sat at the steps. He had been enjoying Jules' tits but the whole time was distracted hoping that he wasn't putting off Ellie by playing with the skinny brunette. He also thought of girlfriend. Was she his girlfriend? He wondered what she was doing inside of the house. He was thinking too much and the hot little brunette was bobbing up and down bouncing on the tip of his cock when the tall bartender saved him. "Host gets first dibs. House rules, old dude." He didn't mind his nickname because he was pretty sure he was younger than any of them. He broke loose of Jules, grabbed a quick grope of Ellie as he waded to the steps and was rewarded by another of her long slow kisses. He found his wine and sat down to watch.

Ellie and Jewels were meshed together like a pretzel and Grayson pulled himself up onto the edge of the pool. The women broke apart and took up spots on either side of him. They took turns sucking the tall guy off as Dan wondered what the protocol was. It was hard to resist the tight asses pointed his direction as their heads bobbed up and down. He wanted to swim up behind them and burry his face between their ass cheeks. Instead he sat drinking at talking to the Cuban. Andy offered him a beer rather than a wine and he was happy to switch. Andy offered him a little blue pill and he swallowed it without thinking. He would be glad he did.

Dan had, to this point, never had an opportunity for a threesome and as he watched the two women with the one guy he was a little jealous. They took turns sucking his cock and he wondered how the guy hadn't already blown his load. He figured the guy probably did this a lot so it wasn't that big a deal. When he finally was ready to finish, his wife took front and center working his cock furiously while Ellie backed away and focused on fingering the thin brunette. Grayson moaned, Jules moaned, and in a little flurry of activity they must have both come. Jules climbed up onto the deck and laying him onto his back straddled his cock. Ellie had propped herself up on the deck and was running her hands over Jules ass. "Go get her, old dude. I know she wants you."

Once he had started, swinging sex wasn't all that different from normal sex. There was a slapping sound coming from the couple fucking beside him but nestled between Ellie's smooth long thighs, he went about licking and sucking her clit about the way he would normally. Ellie was a little tricky, she was one of those women that didn't make much noise and it took him a while to tell if he was doing anything but after a while her hand was in his hair and he found he could feel the muscles in her belly and thighs tightening. When she came, she still didn't say anything but she gasped in a way that sounded almost like a dog's bark. "Woof." She said. He added a finger.

"Stop." She told him in a dry matter of fact sort of way. "You have got to fuck me now. Come on." She took him by the hand and led him back inside. "Back in a minute, boo." She told Andy, kissing him briefly. Dan followed, anxious for what came next.

In the kitchen she pulled open a drawer and pulled out a roll of condoms and made herself a glass of wine.

"I have no clue if this is my glass." She said, looking at it a second before drinking it down. "Look at you, he is still up and at 'em isn't he." She took his cock in her hand and grasped it firmly. "It's a nice one."

"Thank you, you inspire him."

"Oh, now you are just being nice, old dude."

"I'm really not that old, you know."

"Yeah, but you're banging the baby sitter. What's up with that?" It was unusual to have a conversation about your relationship with a woman groping your dick but whatever; he was open to new things.

"I don't know, it just kind of happened."

"Did you get divorced?"

"Almost. We are still separated."

"You should get her into going to parties. It was so good for me and Andy." She had set down her glass and was casually rolling a condom onto his dick. He wished it were bigger, having seen what she usually gets.

"I don't think there is a chance in hell of that happening."

"Bring it up, what do you have to lose." She let him to the living room where she unwrapped her towel from her waist and laid it onto the leather-upholstered ottoman.

"Now come here. I don't normally get to do this?" She was kissing him and pulling him to her.

"Do what?"

"Fuck me old dude. I need it."

She was laid out on her back, he got onto his knees between her legs and the height was perfect. He slid into her easily and she wrapped her legs around him. "Oh yes." She cooed. He started a slow pace, sliding in and out of her watching as her breasts, smaller than Dolly's but still gentle full and round, swayed with his movements. "Oh, Just like that."

In Dan's experience, the more attractive a woman was, the lazier they were in bed. He was expecting much the same with the very appealing older attorney but he was surprised to find her athletic and engaged. The pill had given him a headache, he was hot and sweating and he was a little worried by his heart rate but he also seemed to have a permanent erection and unlike normal, he had not come almost immediately.

They had set a moderate pace, rocking together on the ottoman for a good long time before she had unwrapped her legs from around him and pulled them straight up, extending over his shoulders. "Harder." She whispered. He picked up the pace and the deep soft barking sounds started. He couldn't help but get into it and in a fury to get himself to come he thrust his cock as deep and as fast as he could into her. Her barking became guttural and then her body tightened. She gasped for air and then pulled her legs back down. She was looking at him smiling. "Andy gave you a Viagra, didn't he?"

"Yeah, I've never had one before."

"Fuck, old dude. I have my work cut out for me. Sit back." She put him on the couch.

Ellie took to bouncing and rocking on his cock till he thought it would fall off. She came again, barking and breathing in cowgirl, then turned herself around into a reverse cowgirl and went at him again. They had spectators now and he watched Jules first suck then fuck the Cubans giant cock beside him.

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