A Mutually Advantageous Arrangement Ch. 02

Story Info
Megan's first experience at a clothing-optional resort.
4.3k words
4.65
9.3k
3

Part 2 of the 3 part series

Updated 06/11/2023
Created 08/11/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

For days after my first night with Megan, my mind was reeling with the memories of the erotic pleasures we shared. We had already made plans to be together again on the upcoming Saturday. We talked about spending the entire day together, so I decided to introduce Megan to the nearby clothing-optional resort that Allison and I came to love so much. I was nervous that she would freak out and cancel on me, so I waited until we were driving to the resort before I broke the details to her.

"Megan, I'm not sure how to broach this subject," I started nervously. "I haven't told you everything about the resort we are driving to today."

"Such as...?" Megan replied with a wary look in her eyes. "Is it some kind of swingers enclave or some place where people live out sexual fantasies?"

"Far from it," I answered quickly, somewhat relieved that her speculations were so far off the mark. "The fact is, it is a clothing-optional resort. I might add, it is a family-friendly resort and is one of the most beautiful and highly rated resorts of its kind in the nation."

"You know how modest I am," Megan said quietly. "What made you think that this would be a place that I might like?"

"I admit it was a bit of a gamble, and I am sorry I was not more forthcoming from the start. Allison was a lot like you when I first met her, and it took some convincing to get her to agree to come with me to the resort. But here's the deal. Allison enjoyed the resort from our very first visit, and she is the one who kept asking to go back. It was obvious that the experience helped her to get over some inhibitions, and I really think it was instrumental in helping her to develop a stronger self-image and feeling of inner confidence. I guess I was hoping that you might have the same experience."

"I think it was pretty clear to you the other night that it is not easy for me to get naked. And that was with one person in the dark of the evening. I honestly can't even imagine that I would ever be able to do that in public with other people."

"Again, I'll bring back the idea of trust," I countered. "I've already told you how much I care for you. All I am asking is that you approach it with an open mind. If it turns out to be too intimidating for you, we'll head back home immediately, and I will never raise the issue again."

Megan was quiet the rest of the drive, but I could tell her nervousness was building when we reached the resort entrance. After we checked in at the front gate, I drove slowly through the resort grounds until we reached the lakefront. Along the way we passed a small village of RVs, tennis courts, and pickleball courts filled with people enjoying the summer day in the buff. Megan's eyes were wide as she gazed at more naked people than she had ever seen in her entire life.

"It looks to me like none of these people chose the clothing option," Megan said with a nervous voice. "Are you sure I will be allowed to stay dressed during our stay?"

"Most people come to resorts like this because they like the freedom of being allowed to wear clothing or nothing at all, I explained, "but I assure you that no one will question you if you feel more comfortable dressed as you are. The only place in the resort where nudity is required is the pool and hot tub area."

"Wait, what?" Megan shot back. "All I'm wearing under this sun dress is a bikini. Now you're telling me that I will not be able to wear it if we decide to go swimming?"

"Please try to relax. We don't have to go near the pools if that is a problem for you. The resort is filled with beautiful places for us to relax and enjoy the afternoon. Remember when we talked the other night about trust? I assure you again that I will never ask you to do anything that you are uncomfortable doing. All I ask is that you approach things with an open mind and see where your emotions take you."

I parked the car near the lakefront, and we grabbed a cooler, some towels, and sunscreen before we headed toward the water. I let Megan choose an area for us to sit, and as I expected, she pointed to a couple of chairs that were rather distant from any other resort guests. We draped our towels over the chairs, and then I quickly stripped down and began to apply some suntan lotion. As I popped open a beer, I watched as Megan pulled her sun dress over her head and then quickly sat down in her chair in her sexy bikini. "Are you telling me that if I decide to keep my swimsuit on all day, you are not going to be angry with me?"

"Absolutely not," I assured her as I handed her a beer. "I've noticed that many first timers are a bit reluctant to get naked immediately if at all. Allison was more than a little hesitant the first time we came here together. I will say, though, that I wouldn't be surprised If you eventually spend a good part of the day in the buff before the day is over. If you do, I would be very proud of you, but if feel more comfortable keeping your bikini on, I am perfectly cool with that as well."

Megan applied some sunscreen and lay back in her lawn chair to catch some sun. When I advised her a while later that it was time to roll over, I asked if she would like me to apply more sunscreen to her shoulders, her back, and her legs. She nodded sleepily and so I began to apply the lotion. When my hands reached the back of her bikini top, I asked if it was okay if I untied it so that I could apply the lotion more evenly to avoid sunburn. She nodded again, and I enjoyed the sensation of rubbing the lotion on her flawless skin. When my hands made it to her bikini bottom, I slowly pulled them down a bit so that I could apply some sunscreen.

"Are you enjoying the view" Megan said quietly.

"Actually, yes," I replied. "But I'm really just trying to be thorough in my duties'

"Whatever," she answered. I cautiously eased her bikini bottom down a bit further to apply more lotion. "I guess I know where this is going. How long before my swimsuit is all the way down my legs?"

"Too far? Too fast?" I answered. "I'll back off if you want."

"I'm okay with it. I admit that it actually feels kind of nice to feel your strong hands massaging my bare ass. No one can really see us very well over here, and it is a convenient way to begin to erase some tan lines."

Hearing that, it didn't take long for me to finish the job and pull her bikini bottom down her legs and off. I took my time as I finished rubbing sunscreen over Megan's beautiful naked body, and then I sat back and drank another beer as I admired the view. I kept flashing back to the times that Allison and I soaked in the sun here by the lake over the years, and I felt thankful that I now had another woman to be here with me. I thought Megan might be sleeping, but she lifted her head when she heard music in the distance.

"Live music?" she asked.

"Every weekend," I replied. "There's a small gazebo near the main pool where local performers set up to play. Sometimes it's country/western. Sometimes the old classics from the 60's and 70's. There is also a café near there if you want a bite to eat. They've got burgers and sandwiches and salads."

"Let's go over and take a look," Megan said. "A burger and some fries sound good right now."

"I'm game, but remember what I said as we were driving into the resort. The pool areas are the only places where nudity is required. Are you comfortable with that?"

"I have to be naked just to be in the pool area?" Megan asked nervously.

"No, but I assure you that everyone there will be nude. You are free to put your bikini back on, but you might feel out of place over there if you do."

Megan sat quietly for a couple of minutes, and I could tell she was wrestling with her thoughts. She fumbled around in her beach bag and found her bikini, but then seemed to change her mind as she stuffed it back in the bag. She looked around to see if others were looking at her, but even though none of the other guests were paying attention to her, she still seemed uncertain about what to do.

"Maybe you want to do what Allison did the first time she came here with me. When she finally worked up the courage to go to the places that she knew would be crowded with people, she took a towel with her so that she could cover up in an instant if she felt uncomfortable. That is standard procedure anyway in any clothing-optional or nudist resort. Proper etiquette dictates that people always have a towel to sit on when they're at the pool or the cafe."

That seemed to put Megan's mind at ease a bit, and she stood up and began to wrap the towel around her body. I stepped over to her and suggested quietly that she let me hold both towels as we walked to the pool. I assured her that she could grab her towel anytime she felt the need, but I challenged her to see if she had the courage to make the walk without being wrapped up in her towel. She looked at me with those big, beautiful eyes of hers, nodded quietly, and handed her towel to me.

"Damn. I can't get over how much you remind me of Allison when I first met her," I said as I walked next to her. "She was every bit as modest as you are right now."

"It just seems so surreal to me to be walking around in broad daylight with nothing on."

"When Allison first agreed to let me see her naked after we had been dating for a few months, she told me that she had never let a boy see her in 'all her innocence'. I told her that she looked absolutely beautiful in 'all her innocence' and that it made me feel so good to know that she had enough trust in me to share her beauty with me. I feel the same way right now because I get the feeling that you trust me the same way."

"Did she go swimming the first time you came to this resort?" Megan asked as we got closer to the pool area."

"She and I grabbed a couple of the pool chairs and sat for a few minutes so that she could take in the whole experience. She watched the ritual as people arrived, stripped down, washed up in one of the outdoor showers, and then relaxed in the pool. It did not take long for her to realize that people didn't stare at each other even though everyone was nude. We were in the pool ourselves within half an hour, and after that, the pool was her favorite spot in the resort."

As we approached the pool area, a man came up to us and said "DC! It's good to see you here. We were all so sad to hear about Allison."

"DC?" Megan asked.

"It's the nickname that the resort staff hung on me a while back," I explained. "It's short for 'dot.com'. They all know about the Internet start-up company that I created and that I cashed out with a large profit. I have made some significant donations to the resort."

"Be sure to stop by the office," the man said. "The staff has put together something to express their condolences."

The office was just a short walk from where we were standing, so Megan and I headed there first. When we stepped into the office, Megan noticed immediately that the resort staff were all clothed. At first I wondered if she would grab the towel to cover up, but instead she just stood nervously as I talked to my friends in the office. I think she felt very vulnerable being completely naked in the midst of people who were dressed, but she handled it well.

When we eventually reached the pool, Megan tried not to be too obvious, but her eyes were wide as she looked over a sea of naked guests. I gave her a few minutes to take it all in, and then I said, "When you are finished gazing at more nude people than I am sure you have ever seen in your life, focus on their faces. Their bodies may be all shapes and sizes, but people here generally have one thing in common--they have a self-confidence that comes from the fact that they are comfortable in their own skin regardless of outward appearances. They enjoy the simple gift of body acceptance, both their own and all of the people around them. That is a rare quality that you will not see very often in daily life."

We first headed to the café near the pool and ordered a light lunch. I talked with a few more friends as we ate, while Megan seemed preoccupied with the crowds of nudists lying in the sun and swimming in the pool. Then, as I suspected might happen, Megan announced that she wanted to get in the pool. We showered together quickly and spent much of the rest of the afternoon relaxing in the pool. When we both agreed that we had done enough swimming for the day, we packed up our things and drove back to my house. After admiring Megan's beautiful body all day, I was as horny as I have felt in a long time. On the drive home, I looked over at Megan who was wearing only the sun dress she had used as a cover up earlier in the day. She was slowly running her hands up and down her legs, and I suspected that she was just as aroused as I was.

Once we got back to my place, I quickly mixed a couple of drinks and we both headed out to the backyard. Our first stop was the outdoor shower near the pool to rinse off the last of the suntan lotion that we had applied earlier in the day. I'm not sure if Megan thought it would be a quick shower or not, but once I had lathered up her body, I was inclined to draw out the experience for as long as I possibly could. I stood behind her and let my hands explore every inch of her wet soapy skin. Her breasts felt amazing, and when one of my hands finally made it to that inviting place between her legs, I could tell she was getting very turned on. She squirmed as my probing fingers made their way deeper inside her, and I could tell that her breathing was getting more pronounced each time my fingers found her love bud. My throbbing cock was poking her from behind, and eventually she took the hint and turned around to give me some attention. My knees went a little weak when I felt her soapy fingers on the shaft of my cock. I began kissing her and stroking her breasts as she continued with the most pleasurable hand job I had experienced in a long time.

When I sensed that I was close to climax, I eased away from Megan so that we could both rinse off. I turned off the water and we both began to towel ourselves dry as we walked over to a grassy area near the patio. I laid out a soft blanket on the grass and grabbed the mixed drinks that I had made a few minutes earlier. I motioned Megan to sit on the blanket, and I sat down next to her.

"Why did you pull away in the shower?" Megan whispered. "It felt like you were so close to shooting your load."

"That's exactly why I pulled away. I want the evening to last. If I am going to stay hard to keep up with you, I know I have to pace myself."

We finished our drinks, and then I gestured to Megan to lay back on the blanket. I stretched out next to her as she looked up at the stars. I gave her a passionate kiss on the lips, and then began a slow exploration of her entire body with my lips. I kissed both of her breasts gently and she quietly moaned when I ran my tongue over her erect nipples. I continued down her body until I reached her navel. I let my tongue tickle her there as if to give her a little preview of where I was heading next. She squirmed a bit more once she felt my lips kissing the sweet contours of her labia, and I could sense that she was a little apprehensive as to what might be next.

I had pleasured Megan with my fingers the first night we were together, but my hope tonight was that I could bring her an even more intense experience with my tongue. I continued to kiss that sweet place between her legs until I could tell that she was becoming aroused, and then I eased my way down her body so that I could introduce her to the pleasures of oral stimulation. I slowly worked my tongue between her pussy lips, and as I did, she began to open her legs slightly give me better access. I took the hint and began to probe deeper with my tongue until I was sure I had reached her erogenous spot. This was clearly uncharted territory for Megan. She began to squirm more noticeably as her moans grow louder. I was prepared to take her to an explosive orgasm, but she surprised me and pushed my head slightly away from her body.

"Your tongue feels amazing, but I need something more," Megan whispered. "I need your beautiful cock inside me."

"Are you sure?" I asked quietly. "I wasn't sure you were ready to take that step."

"Yes, Dammit. I spent the whole day gazing at cocks of every size and shape and wondering what it would feel like to have one inside me. I am begging you to fuck me with your beautiful cock."

Needless to say, it did not take much to convince me to fulfill her request. I positioned myself to put the tip of my penis near the sweet opening of her pussy, and I eased her legs apart slightly as I began to enter her. Her reaction was immediate, and it was even more intense then when I had probed her with my tongue. As I continued to slide more deeply into her warm pussy, I bent forward and began kissing her breasts at the same time. We started to move in a slow sensual rhythm. Her body responded each time I thrust a little deeper and that seemed to enhance her pleasure even more. Her moans grew louder and louder, and I could feel that I was desperately close to coming myself. I held out as long as I could, but I eventually succumbed to one of the most powerful orgasms I have ever experienced. I could tell that Megan climaxed at almost the same moment, and for the next several minutes we simply held our warm sweaty bodies close to each other without saying a single word.

When our breathing returned to normal, we both rolled back and gazed up at the stars. Megan was the first to speak. "I still can't get my head around what has happened in my life in just a week. One day I'm sitting in a coffee shop wondering how I'm going to finish my college career, and now a few days later I've had the kind of sexual experiences that I never dreamed were possible. I used to read teenage romance novels and wondered if the lurid pleasures they described were even realistic. I'm lying here wondering how I can ever repay you for what you have done for me."

"Do you remember that I spoke of a mutually advantageous arrangement when I first raised my proposal with you?" I replied. "You have given me something that I feared would never happen to me again after my beautiful Allison died. Nothing will ever replace the deep love that I shared with her, but you have given me a gift that will help me more than you will ever know as I work to move on from my grief."

"I still think I am getting the better end of this arrangement," Megan whispered.

"I am perfectly satisfied with the relationship we are beginning to nurture," I said as I stood up. "I think I will relax in the warm water before we go inside. Do you want to join me?"

We spent the next half hour holding each other in the soothing water in the pool. It felt so good to run my hands over her soft wet skin, and Megan responded by pulling me closer and kissing me passionately. Eventually, I could tell we were both quite exhausted, so we dried off and headed up to my bedroom for the night. We were still naked as we slipped under the sheets. As I moved closer to hold her soft breasts in my hand, my mind was reeling with the memories of the amazing day we had just experienced.

Next morning, I was awakened with the pleasant sensation of Megan's fingers lightly stroking my thigh. She had peeled back the sheets and was gazing at my flaccid penis as she gently massaged my skin. She smiled when she saw that I was awake.

"Until yesterday, I guess I thought that every penis looked alike," she said. "I was amazed at the variety of sizes and shapes. I still liked yours the best."

"Then by all means, feel free to admire it up close and personal. It's yours to inspect."

"That's exactly what I intend to do," she said as her fingers moved to the base of my shaft. "I want to watch it grow to see how hard I can make it."

12