Nancy's Mid-life Awakening Ch. 26

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Nancy introduces Deb and Kyle to Craig and Jeanne.
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Part 26 of the 33 part series

Updated 06/09/2023
Created 06/21/2010
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Chapter 26

Deb Plus Two

Nancy spoke to her newest friend every day in the week following the visit with Deb and her husband, Kyle. Most of the calls were related to the "intervention" that Nancy and Paul conducted for the older couple. Deb shared that they had both opened up with each other and one result was the best sex of their marriage. She said that Kyle was almost glowing each morning before heading to work and his entire personality seemed to have grown younger. One afternoon, Deb called and told Nancy that she and Kyle were on completely firm ground with respect to swinging and they were ready to step outside of their own home for some new adventures.

"You mentioned putting us in touch with another couple when you were here last week. Can we get together and talk about doing that?" Deb asked her.

"How about we plan a lunch together and I'll invite Jeanne to come as well. You two can meet and she can help answer any questions you might have," Nancy responded.

Deb thought for a moment. "You don't think that would be a little weird. She doesn't even know us."

"She and I have known each other for years in a running club that we both belong to, and I'll give her a little background on you so you're not completely foreign to her. I think you'll find she and Craig are very nice and they definitely won't think you're weird or anything," Nancy said with a laugh. Deb agreed and later that morning after Nancy had a chance to speak with Jeanne, the three women made a lunch date for the following day.

During their luncheon, Deb and Jeanne were introduced to each other and Jeanne quickly put Deb's concerns to rest. She told the older woman about herself and her husband, and then told her about the "film studio" they had at their home. Jeanne also strongly hinted that they would like to get together with Kyle and Deb to "get to know each other better". Deb was a little flustered at this invitation from a complete pair of strangers and wanted to talk it over with her husband first. Jeanne understood and suggested that if it would make Deb and Kyle feel more at ease, then the two couples could meet for dinner together somewhere in town for a purely social event. Deb thought that was a good idea and the rest of the luncheon continued with a more relaxed atmosphere.

Two weeks later, Deb called Nancy and said she had a huge favor to ask. She and Kyle met with Jeanne and Craig for a nice dinner that went a long way towards breaking the ice for a follow-on sexual encounter. However, she asked Jeanne if it would be okay for Paul and Nancy to join them as well. Jeanne was perfectly fine with that idea, so Deb wanted to know if they would be interested in coming. Nancy considered the invitation, but sensed there was more behind it. When she pressed Deb on the point, her friend finally admitted that she really wanted to be with two men and she didn't want to spoil Kyle's time with Jeanne. Nancy put off responding until she had a chance to talk with Paul, but she felt sure he would say "yes".

As soon as their call ended, Nancy called Jeanne to see what she had to say. Jeanne confirmed everything that Deb had told her and added that she was already making plans for what she would do with Kyle, but they could easily expand to include Nancy in a threesome. Nancy told her that sounded like fun to her and she and Paul would plan on being there.

It was another week before the small get together at Jeanne and Craig's home. Deb and Kyle were invited to stay the weekend and advised to pack accordingly. When they arrived, Paul and Nancy were already sitting in the living room sipping wine with their hosts. Everyone got up and exchanged hugs and kisses with the new arrivals before eventually settling back down in the comfortable furniture. Each couple remained seated together, but it quickly became two sets of conversations; one involving the men and the other with just the ladies.

When it was time to refresh everyone's drink, Craig suggested taking Kyle and deb upstairs to show them the studio setup. The trio trooped upstairs and when they returned fifteen minutes later, Kyle seemed to take everything in stride, but Deb had a look of amazement.

"Have you guys ever made a video of yourselves up there?" she asked Nancy.

"A couple times," she replied. "But not doing any role playing. We're still trying to think of a scenario we'd really enjoy doing. How about you? Do you already have something in mind?"

Paul could see the same look in Deb's face as he saw at Ann's home. She was feeling overwhelmed with choices and didn't know where to begin. However, she didn't have to think before replying. "I've think got a good idea of what I want to do."

Craig brought out two more bottles of wine and by the time they were finished, everyone was feeling relaxed and happy. He then suggested a trip to the hot tub and all the guests readily agreed. Deb and Kyle started to ask about borrowing swimsuits, but when they saw the others undressing where they were, they understood it was going to be a "clothing optional" event. They started to remove their clothing, but Craig and Jeanne weren't wearing anything more than shorts and t-shirts, so they were the first to get naked. Jeanne went up to Kyle and started helping him out of his pants, which encouraged Craig to help Deb with her clothing.

"Ooooo! You're not circumcised," Jeanne exclaimed. Kyle seemed embarrassed by her comment, but it was clear she found it somewhat exotic. "I've never been with a man who wasn't circumcised," she continued with a large smile. "I can't wait to try you out!"

"Let me give you a hand," he said, trying to shift her attention away from his penis. His fingers expertly opened all the buttons on her blouse and pulled the shirttail out of her jeans. He tugged it off of her shoulders and moved down to release the front of her jeans. Deb stood unmoving and looked around the room as he finished undressing her down to her underwear. Jeanne had finished with Kyle and started to lead him by the hand out to the back deck. Paul and Nancy were already getting in the tub and by the time Deb and Craig showed up, it was already looking pretty full.

Everyone scooted around to make room, but since the tub only had five seats, Jeanne opted to sit on Kyle's lap. Nancy sat against Paul and they relaxed while the others did most of the talking. Paul couldn't help but smile as he watched Craig and Jeanne take charge of their new guests. After a few minutes, the conversation ebbed and Craig pulled Deb over to sit on his lap where the two began making out like a pair of teenagers. Jeanne turned to face Kyle and raised her legs out of the water to rest over his shoulders while her hands were interlocked behind his neck to hold herself upright. The way she was positioned not only showed off her flexibility, but it also put most of her weight on her pussy which was on top of Kyle's crotch.

Paul and Nancy engaged in their own make-out session which was punctuated by Nancy's giggles when Paul became especially frisky in playing with her breasts as they floated at the surface of the tub. The tub was overcrowded with the three couples, but no one minded. At one point, Jeanne moved over to show Deb how she could lower herself and direct one of the footwell jets to impact her pussy. Just after Deb tried it for herself, Craig opened an air valve that created a powerful stream of bubbles in the water jets. That elicited a loud "Ahhh!" from Deb as she hung on to Craig and slowly moved her open pussy up and down in the bubbly jet. Jeanne went back to kissing Kyle and their activity could best be described as frenetic.

They remained in the hot tub for just over 30 minutes before Jeanne got out and pulled Kyle along behind her. She bent down and whispered something in Nancy's ear and tugged on her arm which led to Nancy clambering out behind her friend. The threesome picked up towels to dry off in the cool late afternoon air which already had the women's nipples plainly standing out hard. As she finished drying off, Jeanne called over to Deb. "Don't forget, today is 'Sadie Hawkins Day' so you get to pick the man you want to be with!" With a wave to her husband, Jeanne took Kyle and Nancy by their hands and led them inside the house.

"Oh my! I almost forgot about that!" Deb playfully told the two men in the tub with her. "This is going to be such a hard decision. I think the best thing to help me make up my mind is for each of you to 'try out' for the privilege of being my date tonight."

"Oh really?" said Paul as he played along. "You seem to think very highly of yourself. What kind of date do you have in mind?"

"I was thinking that the man I select will get to spend the entire night in bed with me," she replied cooly.

Craig joined in the fun. "You think you can handle one of us for an entire night?"

"Sweetie, it's you that have to be concerned about being able to handle me!" she quipped. "Let's get out of here so you can begin your try-out."

Deb and the two men splashed out of the tub and dried off. As they walked inside, Deb suggested going to the studio room. When they arrived, she told Craig to set up the video camera to record events on the bed. While he was doing that, Deb went to the closet and pulled out some clothes that she had obviously picked out ahead of time and got dressed. She was wearing a very tight white button down blouse with an equally tight knee-length gray skirt. Underneath, she was wearing a matching set of white panties and a bra.

When she rejoined the men, Paul couldn't help but think she looked exactly like the very hot teacher that she was. He wondered if she actually dressed that way when she went to work. Her clothing was easily something a professional woman would wear to the work place, but on her it was incredibly sexy. The only thing missing was a set of stiletto heels to accent her shapely legs.

Turning to Paul, she said, "I've already been with you, so I'm going to let Craig go first. Your job is going to be operating the camera. Think you can handle that?" As she made her last comment, she winked and gave Paul's small, soft cock a playful yank. Without waiting for an answer, she went back to Craig.

"Just stand there a while," she told him as she continued on to the bed. She sat down and leaned to one side on her arm with her legs crossed. She signaled for Paul to start the recording and then looked up at Craig. "Tell me what you're thinking about right now," she told him.

"Umm, how hot you look," he replied.

"Really? That's all?" she challenged.

"Uh, no. I'm also thinking about fucking those big tits," he admitted.

She sat up and cupped her breasts with her hands to lift them slightly. "These are nothing to how big they used to be," she commented. "I used to wear a 40FF bra before finally getting these reduced to a more comfortable size. Have you ever seen a pair of 40FF tits?" she asked innocently, still holding up her breasts.

"Not in person," Craig answered. His hand was already slowly rubbing his soft cock while he watched Deb on the bed.

"I'm a 38DD now, but sometimes I wonder if they're still too big. What do you think?" she inquired.

"No, I think they look great," Craig said enthusiastically.

"I bet you want to see them better, wouldn't you," she teased.

"You bet!"

Deb undid the next two buttons on her blouse so that it was open to a point just below her bra. Her blouse automatically opened up to show the inside of her bra-clad breasts. Paul zoomed in on her cleavage and guessed that she purposely put on a bra that was a little small so that her boobs would squeeze her boobs together and force them to swell over the top of the cups.

"Is this good enough?" she taunted.

"No. I want to see you topless," Craig answered.

"You probably want to see every woman you meet topless," Deb countered. "I'm not like other women, though. I'm better, but if you want to see how much better, tell me what you would do to see my naked breasts."

Behind the video camera, Paul could see Deb was getting into her role, and if that's what she did during cybersex, it was no wonder she had a long list of online male partners. He shifted the camera's view over to Craig and showed him still stroking his cock, which was already half-erect.

Craig thought for a few moments before replying to Deb. "Um, I'm not sure what you mean," he said trying to sidestep the question.

"You know exactly what I mean," she retorted. "If you're not that interested in me, then you can go away and I'll play with Paul instead."

"Oh no. I'm definitely interested. I just don't know what kinds of things you're talking about. What would you like me to do?" he countered.

"Let's start with something simple," she said. "I want to see you jerk off until you're nice and hard so I can see if that little cock of yours is up to my standards."

Craig stroked his cock faster and it took less than 30 seconds to reach its full length. "Bring it here so I can see it better," she demanded.

He moved over in front of Deb and held his cock out resting in the palm of his hand. As she bent down to examine it, he had a clear view down her open blouse and Paul made sure he recorded him looking. Deb ran her fingernail lightly over the head of Craig's penis several times and when Paul zoomed in again. He could see that each pass pressed in harder than the one before. Craig's penis jumped repeatedly in his hand as she teased it. The last thing she did was use her long fingernail to open the slit at the tip of his cock and wiggle it in the small opening. The sharp irritation that shot through Craig's penis made him cringe and he had a sudden feeling like he needed to pee, but couldn't.

"Go back to where you were," she said suddenly. Craig stumbled backward still holding his tormented penis and trying to mentally stop the feeling of irritation at the very end of it. She slowly unbuttoned the rest of her blouse and pulled the shirttails out.

"Are you ready?" she asked Craig who only nodded in reply. Deb reached behind her and released the hooks holding her bra together and her large round breasts surged forward without the restraint that previously kept them in check. She shrugged the straps off of her shoulders, but used one hand to hold the bra over her breasts. Using both hands, she very slowly lowered the bra to reveal her wonderfully perfect looking breasts and their very large areolae. She let go of the bra cups and the hung below her exposed breasts still suspended by the straps hung up under her blouse and over her arms.

"Here you go," she cooed. "What do you think?"

Craig's eyes were fixed on her breasts as if seeing them for the very first time. "They're beautiful," he replied.

"Oh my," Deb exclaimed. "You seem to be getting soft. You need to take care of that."

Craig resumed stroking his cock and had it hard again in just moments. "Mmm, much better," his temptress cooed. "Are you happy now?"

"A little bit," he responded.

Deb pretended to pout. "You don't like seeing me like this? Oh wait! You said you wanted to fuck my big titties, didn't you?" Without waiting for a reply, she waved him to come close again. "Put that thing in here," she directed while holding up her round globes. Craig placed his hard shaft between her breasts and she squeezed them over it.

"Okay, let's see what you've got," she told him. Craig immediately began humping up and down between her boobs and saw her watching the head of his cock nearly disappear between them before remerging and extending almost up to her lips. Paul removed the camera from the tripod and came over to film the action from the top. The view screen filled with the sight of Deb's two alabaster mounds surrounding Craig's red cock while it drove up and down between them.

Deb let Craig fuck her tits for almost a minute before releasing them. "I'm getting bored. Are you satisfied now?" she inquired almost irritably as she shooed him away. Craig stopped his movement and straightened up.

"Not really," he answered as he resumed his previous spot a few feet away from her. Paul went back to place the camera back on the tripod.

Deb looked up at Craig. "Let me guess. You probably want more, don't you; tell me what you want now."

"I want to fuck you," he replied bluntly. "I want to fuck your pussy," he clarified.

"Of course you do," she said dismissively. Every man I've met wants to fuck me. You think I don't hear that every day?" she asked rhetorically. "I'll let you see my pussy, but you have to do something for me," she said.

"What would that be," Craig asked suspiciously. "Well, something I've always wanted to see is one man sucking another man's cock," she replied matter-of-factly. "I'll let you see my pussy if you suck Paul's cock, and if you do a really good job, I'll let you kiss and lick my tasty little cunt."

Craig looked over at Paul who had just straightened up with a shocked look. "Come on," Deb needled him. "You guys think it's so great to see two women together. What's wrong with us seeing two men together? And besides, why should it matter to you if the mouth on your cock is a man's or woman's?" Paul remained silent without indicating agreement with her argument.

"Let me make it easier for you," Deb told him. "This is going to be part of your try out, too. Either play nicely or go away and you'll never have me again."

Paul was dumbfounded by her comment and wasn't sure whether she was joking with him or not, so he remained where he was. Craig was also motionless waiting to see what Paul decided.

"All right," De said to Paul. "Go away and leave us alone."

"Wait. You were serious?" Paul asked incredulously.

"As a heart attack," she said firmly. "What are you going to do?"

Paul's mind was racing. He never expected her obvious role-playing to reach this extreme, yet she was clearly not joking. He managed to push aside his personal feelings and step out from behind the camera. Deb smiled, and told both men move next to her. As Paul stood in front of her feeling very uncomfortable, Craig knelt down and reached out to lift Paul's soft penis up with his fingers. Paul held his breath tried not to think about it when Craig started stroking his cock slowly. When Craig first took the head of Paul's cock between his lips, they heard Deb scoot closer and tell them, "That's what I'm talking about. I want to see how well you can please another man."

Despite Paul's initial revulsion, he couldn't help but react physically to the stimulation of Craig's mouth. He found himself thinking that Craig was actually very good; almost as good as Nancy. His cock started to grow in Craig's mouth and hand and Deb continued providing verbal encouragement to Craig.

Craig was licking the underside of Paul's cock on his way down to suck on his friend's balls when she queried, "Think you can take the whole thing in your mouth?"

He didn't answer, but continued his way down to the base of Paul's cock and then sucked one of his heavy balls up inside his mouth. As Craig's tongue swirled around Paul's nut sack, Paul felt his cock twitching in response. Finally, Craig finished sucking both balls and went back to the head of Paul's shaft. He moved his mouth around the head and then went halfway down the hard rod before pausing. When he started to move further down, he felt Deb's hand on the back of his head pushing him down to go all the way. Her hand remained on the back of his head even after his lips reached the root of Paul's cock and he was having some difficulty breathing. Craig pulled his head up an inch or two, before she forced him back down.

"Go on. Suck that cock!" she told him. "Let me see you take it all the way down your throat!" Deb didn't release his head until he had gone all the way down on Paul several times. He pulled it from his mouth and looked over at her with questioning eyes.

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