lesbian sex

Not a Sugar Daddy: Part III

Discussing what lies ahead and beyond.

Spankmasters
May 7, 2024
13 min read
Not a Sugar Daddy Pt. 03exhibitionismvoyeurism
Not a Sugar Daddy Pt. 03
Not a Sugar Daddy Pt. 03

Not a Sugar Daddy: Part III

Tadd's phone started ringing an hour later, with the ringtone he'd assigned for Connie - a snippet of BB King's "Lucille" played. "Hi Connie," he greeted after answering.

She teased, "Hey sexy! How's it hanging?"

Tadd replied cleverly, "Low and soft so far. Lack of stimulation, I expect."

Connie giggled, "Good to hear." Then she paused, "There's something serious I want to tell you. A confession of sorts."

"Um, okay," Tadd responded cautiously.

"Have you ever noticed how often you read these stories?" she asked.

"Well, when I'm not getting any real sex, almost every day if I can find one that turns me on," he replied.

"Since last Saturday when you came to visit and then I went to your place, I haven't read any," she said, sounding a bit fearful.

"So, do you only read them when we're not having real sex?" he inquired.

"Yes," she confirmed.

"Some of the categories of stories you like are Erotic Couplings, Incest, Anal, Lesbian, and Group Sex, right?" he asked.

"Yes, it depends on my mood," she replied.

"Can you tell me about one story you really like?" he requested.

"There's a story about two cousins who have the same birthday. They spent a lot of time together as kids, then separated, and finally reconnected when they were around your age. They had sex, she moved in with him, he found out she also slept with her own adult daughter, the daughter visited and they had a threesome, and so on. It's very well-written and hotter than a Saturday night special," she explained with growing excitement.

"Wow, that sounds interesting," he responded.

"Am I a pervert?" she asked.

"Definitely! How did you know that? Do you also read that site?"

"Yes, but I also write erotica," she confessed.

"What?!? You write erotica!?" he exclaimed, pulling the phone away from his ear because of her scream.

"I've read every story you've posted! I love almost all of them and nearly always give you five stars!"

"So we're like two sides of the same perverted coin, right?" he chuckled.

"Wait! You wrote about the long gaps between when you post stories, right?" she asked.

"Yes. I've never written while I'm in a relationship. It's like when you read, I write, when we're not having real sex."

"Some of your fans will be very disappointed in the future," she predicted.

"Maybe I'll continue to write when we're together, inspired by things we do," he suggested.

"I need to know, are your stories completely fictional or are they based on actual experiences you've had?" she asked.

"Only one of my stories is completely true. Most are based on something that actually happened but are 95% fiction. Have you read the State Rally series?"

"Yes. It felt so real I was sure you'd actually done it."

"The only true event in that series was that, at a State bike rally with a club I belonged to, I was asked to be the third person in a threesome with a married couple. But I turned them down. Everything else I wrote came from me thinking about what might have happened if I'd said yes."

"That's incredible! I'll have to figure out which one is completely true," she vowed.

"Change of subject. Have you thought about when you'd like to retire?" he asked.

"Initially, I was planning to retire at 55, but now I don't want to wait that long. The problem is healthcare insurance," she said. "But if we're together, and I sell my house or lease it out, I can afford private insurance. And since I'm in good health, I won't need a gold-plated plan."

"Interesting," Tadd acknowledged.

"What are your thoughts on our future?" she inquired.

"Honestly, I thought you'd want to work until maybe 60," he shared. "So I figured when we're ready, I'll move up there with you, keeping the cabin for mini-vacations and the like."

"I like that plan," she said, the excitement in her voice evident. "When can you come here?"

How many days of intimacy do you think we require initially? Seven? Eight? Surely not extending up to ten! This time, I couldn't determine if she was genuine or still teasing.

He recommended, "I'll return upstairs when you believe your schedule is less congested for us to spend time together. I don't want to abandon Habitat, but I could always visit on Wednesday nights and remain till Tuesday."

"I adore this notion! I'll arrange my schedule and hopefully you can join me next Wednesday." She expressed delight. "But today has been tiring. It's time for me to conclude. Stay aroused and keep falling for me. I'm already smitten with you, darling. Bye!" She declared and promptly ended the call.

Tadd grabbed a glass of Oban and relaxed to ponder the conversation. He was convinced that she genuinely believed she loved him. He had reservations regarding her feelings, which might be lust instead of love. "The optimal approach," he thought, "is to allow things to chill for a few days. It might be beneficial not to visit next Wednesday but rather give it more time."

He was also drained, so following Tess's exit, he urinated, brushed his teeth, and undressed. After Tess returned, he secured her in her kennel and climbed into bed. He dozed off swiftly, contemplating Connie and how much he missed her closeness.

During the subsequent days, Connie messaged Tadd during the intervals between viewings and closings. They were usually concise, flirtatious communications, while Tadd responded similarly. In the evenings, if she lacked work to do, they phoned. Often, they discussed engrossing subjects like politics or medical advancements or controversies. They concurred on approximately 80% of their opinions and appreciated each other's viewpoints on the remaining 20%. Tadd believed Connie had been marginally influenced by his position, though this was likely due to his more extensive life experience. Interpersonally, she was undeniably his equal.

At the end of each conversation, Connie always proclaimed, "Love you!" as a farewell. Tadd had yet to reciprocate, despite acknowledging to himself that he was enamored with her. During the impending call, he resolved to declare his sentiments.

"Hi Connie! How was your day?"

"Great! I finalized a new property and sealed another!" she exulted.

"Congratulations, champion! Now, could we switch topics?"

"Certainly, what's on your mind?"

"You've probably observed that, while you call me 'love you' each time, I haven't said the same. I've mulled over our relationship and now want you to understand that I'm smitten with you."

"YAAAAAAAAS!!!!!!" she exclaimed so loudly that he had to remove his earbuds. "When are you coming to my place on Wednesday?"

"I had pondered waiting another week as I don't want us to rush into anything quickly. But yes, I want to now," he divulged.

"But are you not ready to move in yet, right?" she astutely determined.

"That's accurate. Let's simply observe how it evolves. We're only two hours apart, so we can conveniently visit each other at any time."

"Alright, I can tolerate that for the present. However, when you arrive on Wednesday, you should pack additional clothes you can leave here, so you'll always have what you need without having to transport them each time. If it's fine with you, I'll do the same when I next visit the chalet."

For the following six months, they adopted this standard routine. With Connie being the top agent in her workplace, she did not operate on Mondays, Tuesdays, and Wednesdays as they were the least busy days for agents. Tadd reduced his sessions with his trainer from Monday and Friday to simply Monday, and joined a gym in Connie's town as well as the one near the chalet. Frequently, she traveled down on Sunday evenings and stayed until Wednesday. If Tadd managed to depart from Habitat in time, they often drove up to her locale that same day, otherwise Connie would head there alone and he'd follow the next day.

Notwithstanding, they engaged in sexual activities, or made love, or had intercourse, every day they were united. Initially, Tadd had been apprehensive about maintaining a steady pace, but the absolute opposite was true. The more frequently they engaged, the sooner he recuperated. He could easily generate at least three formidable erections per day, as long as they were spaced out.

Connie was elated. She couldn't keep her hands, mouth, vagina, and occasionally her ass away from his cock. They had sex in every room of both houses. Connie couldn't decide which one was her favorite. She enjoyed it when he bent her over the kitchen counter and took her from behind. Standing up, her back against the wall, and pounding her so hard her ass cheeks hurt the next day. Pushing her down to her knees and shoving his cock into her mouth for a blowjob. Fucking on the front porch, in the open air, knowing that her voice would carry so the neighbors might hear. And, of course, kneeling her in front of the ass chair and taking her back door.

Both of them reveled in the sex and fucking, but their favorite was always making love. Connie cherished it when he gently went down on her, making love to her pussy with his lips and tongue. Bringing her to an incredible climax and holding her close while she spasmed with joy.

"Honey, would you consider going to Hedonism II?" she asked one night.

"Sure. I've always wanted to see if I could handle a nude beach," he replied.

"I'm sure you can. I'll make the arrangements."

A month later, they checked into their room at the resort in Negril, Jamaica. She had managed to secure a room overlooking the nude beach and ocean. "Remember, there are two beaches and pools - one clothing optional where you can go nude if you like, and this side where nude is compulsory," she reminded him.

"Well, in for a penny, in for a pound. Let's start with a stroll on the nude beach to the ocean. Grabbing towels, they locked the room door and left through the slider to the patio and hot tub. Connie locked the door behind them using the keypad the resort had provided so guests wouldn't have to worry about carrying a key or keycard - an issue when you don't have pockets.

Upon their journey, they saw naked people of all ages from 21 onwards, and with all body types. Some were really attractive. Tadd had been concerned that seeing good-looking naked women would cause him to have an erection, but was pleased to discover that the novelty wore off rapidly.

"Wow," he said, "only here for five minutes and nudity seems completely natural."

"That's because you're incredibly comfortable in your body and in excellent shape, especially for a man your age," Connie explained. "Plus, you and I are always naked at home."

"But not in public," he said as he guided her to a tiki hut bar. They found two stools and ordered drinks. Connie, being the outgoing, talkative saleswoman, immediately struck up a conversation with the couple next to them. They got along well and agreed to have dinner together that evening in the Japanese-themed Harrysan restaurant.

Both of them guzzled the freshly poured drinks from go cups, and back at their room, they soaked in the hot tub while they finished their drinks, dried off, and entered the room. Connie laid a towel on the bed and pulled Tadd down onto her. Despite being flaccid for the entire duration at the nude beach, he was already hard. She found his wetness within her vagina and slowly lowered her hips, sliding his shaft inside her. "Oh god! I adore this feeling!" she exclaimed. He began to thrust in and out of her, savoring the warmth and softness of her pussy. He changed the angle at times, sometimes rubbing against her clit and others caressing her G-spot with his head.

They made love until both couldn't withstand the intensifying tension within them. They came together, both moaning so loudly that guests in the adjacent room might hear.

Tadd remained inside Connie, using his knees and elbows to support some of his weight. He slid down her body until her pussy rested in front of his face. He saw cum and her juices mixed together leaking out of her opening and dripping down to her perineum. He immediately extended his tongue and licked it up, then continued up to her opening.

Pressing his tongue inside her pussy as far as it could go, he licked the inside walls clean as thoroughly as he could. 'When I lick her clean pussy, I think it's the most sumptuous taste in the world. Then I do this and think it is.'

Connie entertained her own thoughts. 'I love that he does this. He's so tender and gentle, it's like a sensual massage of my pussy. I'm the luckiest woman in the world.'

Afterwards, they took a shower together, soaping and cleaning each other. Tadd shampooed and conditioned her hair, but she had no way to return the favor since he kept his bald head shaved smooth.

"So, what are we going to do if Bill and Lucy propose swinging or swapping or something?" Tadd said.

"Alright, soulmate, this is the start of our vacation week. It's important we go slow. You remember, we promised ourselves we'd only indulge in something new if we both agreed on it. We came for the enjoyment of being nude together, not strict swapping. So, just go with the flow."

Dinner was delightful. There were options for sushi and hibachi. All of them ordered various samplers and shared them all. The conversation was lively, as everyone was a newcomer. Each recounted their day and their reactions.

Bill mentioned, "To be honest, Lucy and I often swing with some other couples at home. I didn't mean to offend anyone."

"Why would you think we're not good enough for you?" Connie quipped, but they could tell she was teasing.

"No no, that's not what I meant." Bill hurriedly clarified. "You're so hot and sexy, Connie!"

"And I remember what you have, Tadd!" Lucy chirped in.

Connie and Tadd both laughed loudly. "You have a great sense of sarcasm, Connie," Tadd said, explaining it to the others.

"Bill, before we came, Tadd and I discussed what we would do if you two brought up swapping or swinging. For our first day, we chose to stay away from it. You'll never know what can happen in the next week."

"All right," replied Lucy, "We'll tell you if we're interested in joining, but don't feel pressured if we don't. Okay?"

The two pairs left the restaurant and headed to the dance floor. They danced for a while, even switched partners, but eventually called it a night.

"Are you really tired, hon?" Connie asked after undressing.

"I'll show you tired," he responded, grabbing her wrist and pushing her over the back of an armchair. He brutally fucked her pussy from behind for the next 15 minutes until she climaxed loudly. Followed closely by his release.

On releasing her, Connie shoved him back. She stood up, slid between his legs and engulfed his cock with her mouth. She lovingly licked and sucked, leaving his cock spotless. Eventually, she stood up, kissed him deeply and got into bed. After a few showers, they both fell asleep.

They awoke to the sun beaming through the open curtains. They hadn't closed them. Normally, neither liked sixty-nine as it was difficult to focus on oneself while also pleasing their partner. But this was a vacation, a time for breaking boundaries and exploring. Connie climbed atop Tadd, straddling his face and wrapping his cock in her pussy.

They began indulging each other, trying to enjoy themselves as they focused on arousing their partner. They found that if they split their focus between themselves and their partner, they could finally appreciate the sixty-nine position. Connie kept her orgasm back until Tadd announced, "Damn, dear, I'm going to cum!"

In sync, they reached a mutual climax. They heard cheering and clapping, turned to see two couples standing outside their room, watching them through the open sliders. Being a performer, Connie leaped out of bed, facing them and bowed down, eliciting more cheers and claps. While turning away to get back into bed, she bent over to highlight her pussy and asshole, making the audience clap once more. They walked out.

After breakfast, they visited the clothing-optional zone. Since the restaurants and public areas required at least minimal clothing, Tadd wore shorts and a t-shirt while Connie donned a bikini. Upon reaching the nude area, they reflexively stripped.

Their disappointment turned out to be short-lived. Only a few people were fully naked. They considered if the hour might have been the problem, around ten in the morning. Then they returned to their room, got rid of their clothes, and committed to the nude zone all day.

They swam in the nudist pool, tried ping pong, played pool, and participated in a pickup game of beach volleyball. Scheduled snorkeling lessons were planned for the next day. They played in the community hot tub, mingling with other couples.

After lunch, they meticulously slathered each other with full body sunscreen. They focused on the essential areas- breasts, pussy (Connie), cock and balls (Tadd), and their asses (both). On the nude beach, they discovered two available loungers. They asked if they could use both assuming one of them was taken.

"No, they're both completely free," the woman said, implying that no partner was there.

They spent the entire day in the nudist section, trying out various activities. They played pool, ping pong, participated in a pickup game of beach volleyball, and signed up for snorkeling lessons the next day. Connie and Tadd swam nude in the nudist pool. At the communal hot tub, they enjoyed the company of other newcomers.

When they were comfortable, Connie chatted with the woman, as she frequently did. Tina was a captivating strawberry blonde, appearing to be around 35 years old. "Tina, I'm taken aback to find you here all by yourself," she remarked. "I thought only couples could book here."

Tina clarified, "Oh, yes. I'm here with my husband, but he's handled with something else right now."

"Handled?"

Tina chuckled, "I suppose I can't say that without elaborating. Last night at the dance club, we encountered a couple who we presumed were lesbians. We clicked with Jill and Beth and set up a lunch appointment for today. As we neared the end of lunch, Jill mentioned, 'Tina, Beth and I were wondering if we could borrow your husband for a few hours.' This left us both bewildered.

"Beth swiftly detailed that they were indeed bisexual, although they mostly engaged in lesbian encounters. 'However,' she said, 'both of us enjoy cock from time to time and haven't had any in a while. We'd like to have a threesome with him, provided you're on board with it and he expresses interest.'

"No, I don't wish for a threesome with two hot bisexual women," replied no man in history! My husband agreed and since I didn't have any issues, they left for their room."

"Wow," remarked Tadd, "you must be immensely confident in your relationship to be fine with that."

"Indeed. At home, we try some swinging, so it's not a problem. The only drawback is that I can't cease thinking about what could be happening to them. Presently, my pussy feels like a soaked feline!" Tina said. "Observing the two of you, both naked, additionally isn't aiding the situation. There's an excellent cock and an exceptionally appealing pussy beside me."

"Oh, and it is excellent," Connie advised her.

"And her pussy is likely even more delectable than you can envision," Tadd concurred.

"Is there any chance you two would care to invite another woman to join us in a midday frolic?" Tina suggested.

Connie and Tadd exchanged glances. Up to that point, their sexual connection had remained restricted to just the two of them, but they'd discussed potentially extending their boundaries a bit.

"We would adore to, Tina," Connie said.

"Excellent! Our room is a few doors down on the left," Tina said.

"Ours is just above there," Tadd pointed out, getting up. The ladies stood as well and, picking up their towels, entered Tadd's room.

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