Into the Deep End
When Ann and James came down to join her several minutes later, they were both smiling broadly and holding hands. Nancy couldn’t help but smile herself as she thought to herself that they had no idea that she knew why he was smiling like that.
“So, did you guys have any plans for today or are you just hanging out with us?” Nancy asked.
Ann looked over at James with a silent question, and then replied, “We really hadn’t made any plans for today. The party doesn’t start until 8 o’clock this evening so if it’s alright, we’d like to just hang out and visit with you guys.”
“Paul went back to his place to take care of some things there and hold a work teleconference at 10 o’clock this morning. He said it would only take an hour or so and invited us all to relax in his pool,” Nancy offered.
“That sounds nice!” Ann responded quickly. Remembering her sister’s somewhat Victorian views, she asked, “What do you think, Nance? I would need to borrow a swim suit from you, if we went. And James would need to borrow one from Paul.”
Her older sister replied, “Sure, but I don’t know if you’ll fit into any of my tops. Your boobs are a little bigger than mine are.”
“I’m not really that big. I’m sure we can get something to work. If worse comes to worse, I’ll just go out and buy a new one,” Ann said. “When do you want to head over?”
“Whenever you want,” Nancy answered. “I’ve got mm taken care of around here. Let’s go up and see what we can find for you to wear.” Ann gave James a quick peck on the cheek. “Back in a bit, dear.”
As they walked upstairs and approached the guest room, Nancy thought once more about her sister’s sexual attitude. She began to realize how far apart they had grown since their teen years when they shared all their thoughts and secrets. Nancy couldn’t understand how her sister could be so casual about sex, especially in front of others, but apparently, Ann’s talk and actions didn’t seem to upset anybody other than her older sister. Nancy suddenly wondered if any of her other sisters knew about Ann and James’ lifestyle?
Nancy went to her dresser and began searching through the drawers for her swim suits. “I’m not sure that I have anything to fit you. I’m a 38B and you look bigger than that.”
As she tossed them out on the bed, Ann began looked at them. “This one’s cute,” she said and held a bikini top up over her chest.
Nancy looked back and frowned. “That one’s pretty old. I can’t remember the last time I could wear a two-piece suit, but back then, I was probably a 38C. It might be a little small on you.”
“No problem,” Ann replied. She quickly pulled her shirt up over her head and released her bra. Tossing both to the bed, she held up the top again and looked at it before sliding it on. She had to adjust the shoulder straps and when she finished, she turned to look at herself in the mirror. It was obviously small on her and her tits were bulging out over the top of the cups. “I guess you’re right,” she told her big sister and then slipped if off.
As she stood there topless while Nancy continued to search for more swim suits, Ann asked her, “Did you enjoy the performance?”
“What?” Nancy said looking up at her. Seeing the knowing smile on her sister’s face caused Nancy to blush. “What are you talking about?”
“You don’t need to pretend. We know you were watching us earlier in our bedroom. We actually planned for it.”
“What do you mean you planned for it?” Nancy asked in confusion.
“Just that,” Ann told her. “We decided that since you seemed to enjoy watching us on the sofa last night, perhaps you’d like to watch the full show. I opened the door partway and when we heard you coming up the stairs, we started making some noise to get to you look inside. “
“Oh my, God! I can’t believe you did that,” Nancy exclaimed. She could feel her face growing hot and flushed with embarrassment.
“Oh, we thoroughly enjoyed ourselves. We like to play and have fantasy sex all the time, and it’s also kinda fun to know someone is watching. We would both check the doorway every now and then to see if you were still there, but we tried not to look too often because we didn’t want to scare you away,” Ann replied. “So, did you like it?” she asked with a wink.
Nancy remained speechless trying to figure out how to respond. A little voice in the back of her mind wanted to say, “Hell yes, I really got off on watching you guys have sex and imagined it was me in there instead of you”, but there was no way she could bring herself to admit it out loud. She looked at her sister standing topless in her bedroom talking openly about her sex life and had no idea how to respond.
Ann saw her stranded in indecision, so she went ahead and broke the silence. “You don’t have to say anything if you don’t want to. I can assume from the look on your face now and the fact that you watched us until the end that you did enjoy it. That makes me happy.” She then turned back to the bed to look through the remaining swim suits to try and find one that fit.
By the time they got on the road, the morning had already become a typical hot, muggy, summer day in Charleston. The air conditioner didn’t have a chance to start cooling the inside of the car before they reached Paul’s home, and everyone was already starting to sweat in the humid heat. Going inside, Nancy gave them a short tour of the house, showing them where Paul’s guest room was, the kitchen, and the porch leading out to the pool deck. Leaving Ann and James in the den, Nancy went to the study to check on Paul.
As she went in, she found him sitting back in his office chair in just his boxers with his headset on and plugged into the computer. She startled him as she came up behind him and put her hands on his shoulders, but the serious look on his face was quickly replaced with a smile when he saw her. Reaching around, he wrapped his arm around her waist and pulled him over onto his lap. Nancy felt a pang of guilt pass through her from her earlier voyeurism as he kissed her and rubbed his hand over her back and waist.
She gave him a quick squeeze and mouthed that she was going to take care of her sister as she rose up from his lap. He nodded in assent, and then returned to the conversation that was continuing over the computer headset.
When Nancy returned to the den, she found Ann had already changed into the one swim suit they found that seemed to fit reasonably well. It was still on the small side and barely covered her breasts, but the bottoms fit well enough. Going to Paul’s bedroom, Nancy found a pair of shorts that James could wear in the pool and brought them out for him to change into. Excusing herself, Nancy returned to the bedroom and changed into her swimsuit, a more modest one-piece affair, and rejoined the others who had shifted outside to the pool deck.
As she walked out into the bright sun, Nancy could sense James watching her and when her eyes adjusted to the brightness, she saw the half-smile on his lips. Ann was sitting in front of him on a chaise lounge chair while he rubbed some sun screen into her back, shoulders, and arms. When he finished, they exchanged positions and she did the same for him. Nancy was already well-tanned from her running as well as the time she spent at Paul’s pool, but began rubbing some sun screen over herself as she sat down in the chair next to her sister.
“This place is great!” Ann exclaimed. “So nice and peaceful with plenty of privacy. If I lived here, I’d be spending time sunbathing here every day.”
“It is nice,” Nancy replied. “And when it starts getting too warm in the sun, it’s nice just to sit out in one of the floating lounge chairs and let the water help keep you cool.”
“Did you guys want a glass of water or something else to drink?” she asked.
“Water or some iced tea would be nice,” Ann responded.
“Water’s good for me, too,” added James as he stretched out on his chaise lounge and closed his eyes to the sun.
Nancy went back inside and checked the refrigerator to see if there was any tea. Pouring a glass for herself and Ann, she filled another glass with ice and water for James and went back outside. By now, Ann had turned over on her stomach and untied the straps holding her bikini top on so she could work on tanning her back completely. Nancy decided to follow suit and after repositioning her chair, she quickly lowered the straps of her suit from her shoulders and pulled it down to her waist keeping herself turned away from the others as she stretched out on her lounge face down.
She felt half-asleep when she heard the door open and looked up to see Paul coming out to join them. He was still wearing just his boxer shorts, which caused her to tell him, “Get back inside and put something decent on!”
He laughed. “I’m perfectly decent. You can’t see anything more than if I was wearing a swim suit. And you know I don’t have any of those anyway.” He pulled a chair up alongside Nancy and reached out to caress her warm back and shoulders. “You, on the other hand, have entirely too much on!” he declared.
Nancy ignored his comment and laid her head back down on the lounge chair and closed her eyes to enjoy the warmth on her back and legs. Across from her, Ann decided she had spent enough time sunning her back and turned over letting her top fall to the side as she settled on her back. Her breasts jutted up in the sun with her small reddish nipples dwarfed by the globes they topped. James gave Paul a knowing grin as they both watched her rub sunscreen over her firm white mounds and down across her slightly round stomach. Nancy continued chatting with Ann on a new topic with her eyes still closed, oblivious to her sister’s display, while Paul and James carried on their own conversation covering work, lawn care, the college football ranking system, the designated hitter rule, and the decline of civilization in general. Their gazes constantly returned to Ann’s pale breasts glistening under a sheen of sunscreen and perspiration in the hot sun.
It wasn’t until almost 20 minutes later when Nancy decided to turn over that she noticed her sister. At that point, she bit back a comment knowing that all it would do is draw more attention to her sister. She also thought the lack of obvious reaction by Paul was a good thing and started to believe that her sister’s partial nudity wasn’t going to result in him saying or doing something stupid and hurtful.
Getting ready to shift her position, Nancy modestly pulled her suit up over her breasts, but left the straps off of her shoulders as she settled back into the lounge. Paul and James had shifted their conversation to discussing the pros and cons of swimwear, specifically bikinis versus one-piece suits using the two women to illustrate their various points. Not surprisingly, the two men both quickly agreed that swim suits were over-rated and the world would be a much happier place without any clothes allowed around the water for women. Ann’s vocal opposition to this idea was loud and immediate. Her counter-proposal was to get rid of clothing for both sexes around pools and at the beach.
“We like to check you guys out just as much as you like checking us out, right Nance?” she asserted.
“You bet! What’s good for the goose is good for the gander,” Nancy replied.
“What do think, James? I think they have a point. Since men’s swim wear is topless, I think women should also be topless,” Paul joked.
“Hey, you don’t have to twist my arm,” said Ann as she peered through half-closed eyes in the sunlight. “I’m all for clothing optional recreation. Come on sis! You need to get with the program!”
Nancy tried to ignore her younger sister and the calls from her boyfriend and brother-in-law for her to drop her top, but they were insistent.
“Come on Nancy! We’ll all adults and we all seen boobs before. Stop being such a prude!” Ann chided.
Realizing she wouldn’t be left alone until she complied, Nancy gave in to their calls and peeled her swim suit down to her waist, revealing her well-tanned top. She was acutely conscious of how her small soft breasts drooped and lay flat along her chest when she reclined and in the back of her mind, she compared herself unfavorably to her younger sister’s near-flawless body. However, if anyone else noticed, they refused to comment on her less than perfect form. Instead, James was the first to state the obvious.
“Mmmmm…. It doesn’t look like this is the first time you’ve sunbathed topless. What’s with all the drama earlier? Are there any other missing tan lines we should know about?” he teased. Refusing to be baited, Nancy coyly replied, “Perhaps,” and left the implied question unanswered. The conversation returned to less titillating topics and Nancy found herself becoming less concerned about her partial nudity in front of her sister and brother-in-law. Once again she was surprised at what she didn’t know about her sister’s life and attitudes. The only other moment where she began to get a bit alarmed was when Ann decided to remove the bikini bottom she was wearing to get a more complete tan. When Ann rolled back over on her stomach, James moved over to apply some fresh sunscreen to her back and shoulders, then down over her bare bottom and legs.
Ann’s whole casual outlook on nudity and sex left Nancy somewhat at a loss, but Paul seemed similarly indifferent which became one less concern for her. It wasn’t until later that she realized she had always equated nudity with sex and here she was in a situation where nudity was not necessarily a prelude or forcing function to have sex. When she thought about it, she had the same feelings when she first started seeing Paul and had to overcome her reluctance to sunbathe topless or completely nude with just him around. She used to kid him about being a closet nudist since he was always walking around his house wearing little or nothing in the mornings as he made breakfast, telecommuted from his study, or just relaxed with her.
It wasn’t much longer before everyone decided to shift back indoors before they became sunburned, but following Paul’s lead, they each jumped in the pool for a quick dip to cool off before heading inside. The cool water caused the women’s nipples to immediately stand out, however Nancy had opted to pull her suit back up in place while Ann jumped in au naturel.
Leaving the pool, they went back into the screened porch to decide what they were going to do for lunch and the rest of the day. Paul’s shorts were too wet and heavy to stay in place, so he kicked them off without a second thought and went naked into the kitchen to make up a pitcher of margaritas and some snacks for everyone. Nancy was dumbstruck by his lack of modesty in front of her already nude sister. James went inside with him leaving the two women to chat alone.
Ann still hadn’t shown any inclination to put some clothes on, which left Nancy feeling a bit disturbed again.
“Aren’t you going to get dressed, now?” she asked.
“Not yet. I was thinking I might want to go back in the pool after a bit. It felt so good just now,” Ann replied.
“I don’t know that I like you sitting around Paul like that,” Nancy said a bit heatedly.
“You need to get over that,” Ann lectured. “A blind person could see that Paul is only interested in you. He might enjoy looking at some women, but believe me, he LOVES you, and I can’t believe he’d do anything to jeopardize your relationship, especially not with me!”
“How can you say that?” Nancy persisted. “You hardly know him.”
“I’ve known him longer than you think. We first met in a swinger’s group when he was with his ex,” Ann confided. “I think the whole thing was her idea, but he went along with it. He stood out a bit among all the men in the group and a lot of the women were interested in giving him a “test ride”, but from everything I saw, he remained devoted to her. Frankly, I wasn’t sure what he saw in her. I thought she was a stuck up bitch and the only reason she wanted to join the club was so she could have more men drool over her and show off her hottie boyfriend to the other women. Everything about her was fake. She had fake boobs, veneers on her teeth, botox on her face, and probably a few other enhancements that weren’t immediately obvious. The only things that she was missing were implants in her ass, because she had what James used to call, an “ironing board behind.” Even her personality was fake. The second best thing that ever happened to Paul was her running off with some dumb bastard. The best thing that happened to him was you, and I bet he knows that!”
Ann’s sudden outburst left Nancy stunned with its revelations. Paul never spoke about his ex-fiancé since their first day together and had certainly never mentioned some of his previous “social activities.” Feeling a bit deflated, Nancy sat back and considered her sister’s statements.
She knew that if Paul was only interested in a woman for her body, he would have never given her a second glance. When she looked at herself critically in the mirror, what she saw was a 55 year old woman with short hair that wasn’t stylish; a face that wasn’t particularly remarkable; two small droopy boobs; almost non-existent hips; and a tummy that bulged out too much as the result of three pregnancies. The only things she did like about her appearance were her toned, muscular legs and arms.
Despite her own misgivings about her appearance, Nancy recognized that Paul never failed to compliment her various body parts whenever the opportunity arose. When the two of them went out together, he always made sure she knew he cared for her by the small gestures and courtesies he extended. She once listened in from the next room as he was talking about her to some of his friends who had been invited for dinner and drinks. She was embarrassed by the praise and admiration he heaped on her for all her accomplishments and talents. When she came back in the room with fresh drinks, Nancy felt a subtle change in how the others looked at her and spoke to her.
As she sat back in her chair silently thinking everything through, she had to fight back the tears that came from own insecurities that kept her from accepting that her relationship with Paul wasn’t temporary until he left her for another woman or doomed to failure because she couldn’t meet his needs. She had become so insular with her life over the past 25 years that it was hard for her to truly open herself up to another person and risk ridicule or dismissal. That was probably why she had become somewhat distant and detached from her sisters, especially Ann and knew so little about what they did or how they thought.
Paul and James returned with a tray loaded with various cheeses, crackers, dips, and chips, plus a large pitcher of margaritas and four chilled glasses. Nancy quickly wiped her eyes and put on a smile to cover up her brief self-reflection. She immediately noticed that James had stripped off his wet shorts to join Ann and Paul in their ‘natural look”.
“Oh hell,” she thought to herself. “It’s just a matter time before they start giving me crap again about keeping myself covered up.” And in a move that surprised herself and everyone else, Nancy stood up, peeled off her swim suit, and leaned over to pick up a margarita before plopping back in her chair. As she sipped it, she was aware of everyone looking at her with approving smiles and their eyes were focused on her face, not the rest of her bare figure. Nobody commented on her sudden change of heart or made teasing remarks and when the conversation resumed, Nancy remained unusually quiet for a short while as she slowly accustomed herself to this novel environment, then slowly joined in with her normal exuberant and lively personality. By the time she finished her second margarita, she had mostly forgotten that no one was wearing any clothing and was enjoying the ribald conversation between Paul, James, and Ann.
When the first pitcher of drinks was finished, Paul got up to make a second pitcher and to replenish the snack tray for everyone. Nancy got up to help and hurriedly followed him into the kitchen.
“This is so bizarre!” she said in a low, excited voice. “How can you be so casual about running around naked in from of people you barely know? I mean, Ann told me about how you guys met at some swinger parties, and I’m sure you saw a lot of men and women without any clothes, but they were all having sex, not just sitting around acting normal.”
Paul looked down at her with a smile, “It’s no big deal unless you make a big deal out of it. When I was in the Navy, we pulled in to some overseas ports where they had nearby nude or topless beaches and all us Sailors had to go see what they were like. Once we got to the beach and saw everyone behaving normally, we started feeling self-conscious for being the only guys wearing any clothing and standing out like a bunch of goofy American perverts. So, we took our clothes off to blend in and after getting over the initial feeling that everyone was looking at us and judging our appearance, we found it wasn’t any different than going to a beach here in the U.S. Once you get past the fear of everyone looking at your body in critical judgement and realize they don’t care that you don’t look perfect, it becomes more enjoyable.”
Nancy moved into his arms and hugged him tightly, enjoying how his body helped warm her cool skin. They kissed briefly and she felt his hands moving over her bottom to squeeze it and pull her up a little higher against him.
“How come you never told me you met my sister at a sex party?” she asked looking back up at his face. “Did you ever screw her?”
“First, I didn’t know she was your sister until she came here last night, and I didn’t want to freak you out by telling you about things I did in the past that I knew you’d have a hard time understanding. And secondly, ‘no’, I never had sex with your sister. I only went to three or four parties. I’m sure if I’d kept going, I would have eventually hooked up with her, but since I met you, I haven’t been interested in screwing other women.”
Nancy took comfort from his statements and laid her head against his chest for a moment. She felt her breasts pressing up against his midriff and thought she felt him stirring between her legs which suddenly made her feel special. Despite her self-criticism of her appearance, it was nice to know that she could still arouse Paul without any effort. Her hands moved down his back and over his nice ass, enjoying its smooth, hard, muscular curves that she always admired. She noticed his hands had begun caressing her back and the softness of her own ass in response to her attentions. She raised her face to meet his and their lips met for another long, soft kiss that left her feeling wet between her legs and Paul’s swelling member rising up against her.
Remembering where they were and their company waiting out on the porch, she forced herself to release him with a smile while muttering softly, “Not now.” Turning back to the kitchen counter, Paul resumed mixing up a fresh pitcher of margaritas and Nancy began replenishing the snack tray with fresh cheese, crackers, and fruit trying to recompose herself.
Without warning, she suddenly felt Paul’s hand moving up between her legs from behind and trying to work inside her pussy. She instinctively tried to close her legs, but Paul’s free hand wrapped around her waist and partially lifted her up to bend her over the island counter. Unable to deal with this new surprise, Nancy was distracted just long enough for Paul to slip two fingers up inside her warm cunt and begin fingering her. She briefly continued her weak protests, but it wasn’t long before Paul had her completely wet and she relaxed as the pleasure mounted between her legs.
Paul paused momentarily to remove his hand and move his body between her thighs, grasping each leg and pushing her further up on top of the island. The coldness of the granite on her skin caused a chill across her body. Nancy moved her arms forward to hold the opposite edge of the counter, as she felt Paul spreading her legs and ass cheeks even wider. Leaning down, Paul began licking and nibbling between her cheeks starting just below her tight little brown pucker and working downward towards her swollen labia. She felt his tongue over her perineum and then licking up the juice from her pussy and trying to reach up inside her, but he met with limited success.
She momentarily forgot about her sister and brother-in-law sitting outside on the porch as she reveled in the feeling of Paul eating her from behind. It was a position she had never tried before meeting him and after the first time, it became one of her favorites. She felt his arms reaching up and around her legs from the inside to help support them while allowing his hands to keep her spread before him. He was practically lifting her waist up off the counter with her upper legs resting on his upper arms and shoulders in his effort to reach further into her pussy and to find her clit with his probing tongue. She sensed his frustration, but could do little to make herself more available.
Paul stood up between her legs and carefully pulled her waist just over the edge of the counter and she looked around to watch him finish stoking his cock to its full length, then move up into her. It easily slid into her dripping wet pussy and he wasted no time in pounding it in. Paul’s hands held her firmly by her hips as he continued thrusting in and out, and Nancy continued to hold on to the edge of the counter to keep her body from rubbing uncomfortably across the smooth cold granite surface. The whole scene reminded her of what she had watched James do to Ann earlier that morning. She became briefly alarmed at the thought of her sister or James wondering what was taking so long and walking in on her and Paul, but at that moment, she felt Paul drawing himself into her and holding her tightly against his pulsing cock as he released it’s warm load into her.
Paul bent over her and kissed her shoulder and neck as while she lay out in front of him, unable to move until he released her. She heard his breath slowing and noticed his cock was rapidly softening inside her before slipping out completely. As he moved out from between her legs, he helped Nancy off the counter to stand and turn around to face him. Her breasts were reddened from being pressed down on the counter surface and she felt a small trail of wetness leading from her pussy down along the inside of her thighs.
“What was THAT all about?” she asked.
“I don’t know,” he replied. “I just saw you standing there and had this sudden desire to taste you, and then one thing led to another,” he continued a bit lamely.
“What if someone walked in on us like that?” she asked.
“The only people around are Ann and James, and it would take a lot more than seeing us have sex to make them uncomfortable,” he answered.
“Maybe, but I’d be too embarrassed for words,” Nancy concluded.
At that moment, they heard the porch door open and Ann walked in the kitchen.
“Hey you two! We were wondering if you got lost or something,” she exclaimed.
“No, we were just getting ready to come back out,” Nancy said as she hurried to get the snack tray and start back outside. Paul finished stirring the pitcher of margaritas before taking it and following Nancy out of the kitchen with Ann close behind.
After rejoining James on the porch, Paul poured everyone a fresh drink and Nancy offered their guests some food from the tray she was carrying. Ann sat back down on the wicker love seat next to James and sipping her drink, she noticed the wetness on the inside of Nancy’s thighs, as well as the obvious post-coital condition of Paul’s cock. Deciding not to embarrass her sister, Ann said nothing but smiled to herself at the recent changes in her older sister and hoping that Nancy would continue to accept and embrace her sexuality through new trying new ideas and experiences.
That evening, Ann and James headed out to their party leaving Paul and Nancy alone for the night. Paul took care of preparing dinner and surprised Nancy with a nice candlelit meal. The soft music and wonderful food left Nancy feeling a bit giddy as he took her bad to his bedroom after their dinner. He helped her undress with surprising gentleness that was a prelude to a long, slow, and passionate love-making. Paul spent nearly 30 minutes kissing, licking and caressing her entire body and it was so relaxing, she felt herself almost falling asleep under his gentle soft touch. When he finally entered her, he took long slow strokes; pausing frequently to just hold her close and kiss her while his cock completely filled her warm pussy.
When they finished, they fell asleep in each other’s arms and never heard their guests finally get back early in the morning. Ann and James left to go back to their home the following afternoon promising to visit more often and extracting a promise from Nancy and Paul to visit their home soon.

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