A Mutually Advantageous Arrangement

My name is Paul. I'm 42 years old, in great physical shape, and financially sound. I recently sold a startup company for a significant profit, and so it would seem that I have everything I need in this world. Sadly, the one thing I no longer have is the love of my beautiful wife Allison who passed away earlier this year from cancer. For weeks, I could not find the energy or the motivation to leave the house, but recently, I decided to go out and visit some of the places that Allison and I liked to go. I stopped by a popular coffee shop and was surprised to see a young woman who had lived next door to me years ago before her parents had to sell the house because of financial setbacks. I had not seen Megan for years. I was surprised to see how much she had matured. She was sitting by herself and looked very sad, so I decided to go over and talk with her.

"Megan," I said as I approached the table. "It's been years since I last saw you. You have grown into quite the young woman."

"Mr. N!" Megan replied as she looked up to see me. "I was so sorry to hear about your wife's death. I always thought that you were a perfect couple, and you were always so nice to me and my family."

"Please, let's drop the mister stuff. You're an adult now. Please just call me Paul."

"Are you doing all right? I can't begin to imagine how your life has changed."

"It's not easy," I replied. "Every day is a challenge, but I am learning to cope. I came over because you looked so sad. Is everything okay with you?"

"I broke up with my boyfriend," Megan said quietly. "I can live without him, but he was giving me some financial help that I needed to get through my last year at college. My next payment is due next week, and I honestly don't know where I can find the money."

"Can your folks help you out?"

"Not a chance. You remember the money issues that forced them to sell the house next door to you. When I was first accepted at the college, they made it very clear to me that they would not be able to help with the finances. I'm so close to getting my degree, but now I'm very worried that I won't be able to finish my senior year"

Megan and I sat and talked for almost 45 minutes. We caught up on the news in our lives for the past few years, but it was very clear that Megan was completely distraught over her circumstances. I had an idea about how I might be able to help her, but the coffee shop did not seem like good place to talk about it. I asked her if she was willing to stop by my house so I could share some ideas with her about how I could give her some help with the money issues. She said she was free that night and that she could stop by around 7:00 o'clock.

I was thrilled that I might have a real living guest in a house that had been so quiet the last several months. Megan arrived right on time, and since she knew I would probably be in the back yard on the pool deck, she skipped the front door and came through the gate to the back yard. She looked so beautiful. She was wearing a colorful cotton shirt, pastel shorts, and sandals. A perfectly comfortable outfit for a beautiful summer night. I had already set out some snacks and a pitcher of margaritas, and so we quickly settled in for what I hoped would be a relaxing evening. We finished getting caught up on family news and other small talk, and then we began to talk more about Megan's money problems. She told me she had a part time job, but she knew she could never earn enough to pay the tuition bills. I suggested to her that I had the financial means to give her some help, and I asked if she was interested in setting up an arrangement that might help both of us. At this point she looked a little startled, and she asked me what kind of arrangement I had in mind.

"It is clear that we both have some significant needs in our lives right now," I explained. "You have a very pressing need for some cash to complete your college dreams, and I have a desperate need for some meaningful companionship in my life after Allison's death"

"Companionship? Are we talking about social get-togethers like we are doing right now? Or are you thinking about some kind of sexual arrangement?"

"I honestly don't have any preconceived expectations right now. I think we both know each other and trust each other pretty well, so I thought that we might start simply and see where our feelings take us. It seems to me that that's the way all meaningful companion relationships evolve."

"I will have to give this some thought," Megan replied. "It would seem kind of weird to get involved in a relationship with an older man, especially one that I have known since I was a little girl. And I wonder what our friends and neighbors would think about an arrangement like this."

"No one else needs to know," I argued. "My driveway is completely hidden from the street, and so no one would know if your car was parked at my house. I was not planning to meet together in any of the local restaurants or bars, so there would be little or no risk of other people seeing us together. Any financial transactions we might agree on would be done online directly from my bank account to yours."

"Wow, my head is spinning right now. When we met at the coffee shop today and you mentioned that you might be able to help me, I thought you might be thinking of a loan with some very friendly terms for me. How much time do I have to think about this proposal?"

"I would say that the answer to that question is totally up to you. You mentioned that the next tuition payment is due in a few days. As I see it, that is the factor that will shape any other agreements we might make."

As we continued to talk about my proposal over the next half hour, I could tell that Megan was still uncertain about the whole thing. After we had drained most of the pitcher of margaritas, it was clear that that she was getting a little tipsy. Sensing that her inhibitions had been dialed back a bit, I suggested that we go for a swim in the heated pool. Her eyes got wider.

"The water looks inviting", Megan replied quickly, "but I don't have a bathing suit with me."

"No one ever wears swimsuits here," I said with a smile. "Look around you. I purposely installed walls that are high enough to keep nosy neighbors from spying on me."

"That's not true," Megan retorted. "When I lived next door, my brother and I went swimming in your pool all the time. I know very well that we were not naked during those swims."

"You are right that when neighbors swam together at our pool during the day, it was customary to wear swimsuits. But that was a long time ago, and now only adult friends swim in my pool. And I can't honestly remember the last time that any of them were doing it in anything but their birthday suits. Besides, you are a college girl. I have to think that quite a few boys have seen you in the altogether in the dorms or at parties."

"Actually, no." Megan spoke in a subdued tone. "I have only had a couple of boyfriends, and I have not stripped down for any of them. Besides, you are a family friend. I would feel so embarrassed to be naked in front of you."

"Well, then, maybe I have misjudged your possible reaction to the proposal I had hoped to discuss tonight. We have done a lot of small talk and it has been fun to see you again after all these years, but we haven't really gotten to the main reason I wanted to meet with you."

"Now you are starting to scare me," Megan replied. "Did you ask me here to get me naked and have sex with you? I admit I really need money, but I want to do it in a respectful way."

"You disappoint me if that is what you think of me," I replied. "If all I wanted was a few one-night stands because I am desperate for sex, I have the means to do that any night of the week. Since Allison passed away, I have come to realize that what I truly need and crave is companionship. We each have something that the other needs very badly, and I thought that we might find a way to reach a mutually advantageous arrangement."

"If all you are looking for is a companion, why do you need to see me naked?"

"You miss the whole point," I replied. "I asked you here this evening so that we could have a serious discussion about ways that we might help each other. As you mentioned in the coffee shop, you are strapped for funds, and you fear that you will not be able to complete your senior year at college. I am desperately lonely after Allison died, and I have always enjoyed your company. I suggested a swim so that we might both let our defenses down a bit and enjoy the warm water and the beautiful evening. It seemed like it might be a relaxing way to talk more about any agreements we might make. If this seems threatening to you, perhaps I have miscalculated. You are free to leave at any time if I have upset you."

"I'm not upset. And you are right, I really do need the money. It's just that I was not prepared to go skinny-dipping tonight with a family friend."

"It's a matter of trust," I continued. "I need to trust that you will use any money I give you in a responsible way as you say you will. You need to be able to trust me when I promise you that any and all aspects of a possible companionship will be based on the premise that you are free to terminate the agreement at any time you feel threatened or uncomfortable. If the simple thought of swimming in the nude--something that millions of people do every day--is so scary or repugnant to you, I do not think we will get very far in our exploration."

Megan sat down and poured another margarita. She was silent for several minutes and then said "I am trying to steel my courage. As I said before, no man or boy has ever seen me naked."

"It sounds like you are considering the possibility," I replied. "Let me ask you this. Would you find it more comfortable if I were to undress you and you undress me? Allison and I swam nude every night, and she always told me that she found it more exciting and romantic if I stripped her naked instead of undressing herself. She said that she loved the feeling of my strong hands caressing her body as I took off her clothes. We had total trust in each other, and I would like a companionship between us to be based on that same type of trust. Remember that you can always tell me stop at any time you are uncomfortable."

"Maybe it's the booze talking or else you are a master salesman," Megan finally said with an uncertain smile as she stood up. "I think we should quit talking and get in the pool before I change my mind."

I set my glass down and stepped over to her side. "I care for you very much." I told her quietly as I looked into her eyes. "I think you know that I would never do anything to hurt you."

I gestured for Megan to sit for moment while I slipped off her sandals. Then I had her stand again while I slowly pulled her cotton shirt over her head. I think she figured that her shorts would be next, but instead I reached back and unhooked her bra. I think I might have sighed quietly when I first saw her flawless breasts because she made a quick effort to cover herself. I kissed her on the cheek and asked her if she would let me gaze at her beauty. She lowered her arms and actually seemed to enjoy it when I softly caressed each breast.

"I've watched you grow up from a young girl," I said as I continued to caress her soft breasts. "None of that prepares me for the beautiful young woman you have become."

I reached down to unsnap her shorts and gently slid them down her legs. All that remained was a pair of lacy white panties. I looked at her one more time to see if she was prepared for me to continue. Her eyes were wide now, but her simple nod suggested that I should complete my work. I caressed her breasts one more time, then slid my hands down her torso and removed her final garment. I thought she might try to cover her body with her arms at this point, but she stood without apparent shame as I explored her entire body with my eyes. She was more beautiful than I could have imagined.

It was Megan's turn now, so I quickly kicked off my sandals. She surprised me by unsnapping my shorts and sliding them down my legs. Perhaps she wondered if I was wearing anything under the shorts, or maybe she just wanted a first look at the bulge that I had developed as I undressed her. The shirt came next, and she seemed to enjoy running her fingers through my chest hairs. I thought she might just pull my boxer briefs down, but instead, she began to caress my cock through the fabric as if to calculate the size and shape of my equipment. Just when I thought she would never complete the task, she pulled down the front of my briefs to let my cock come springing out. Her eyes became wider when my full cock came into view.

"One of my boyfriends liked it when I stroked the fabric over his cock," Megan explained. I never did get to see the real thing, but I can guarantee you that it was not this large."

Now that we were both naked, Megan took my hand and led me to the steps of the pool. We both eased into the water, and for several minutes, we swam quietly and gazed at the stars above. Eventually I swam closer to her and asked her if I could hold her in my arms. Megan nodded quietly and swam over to me.

"It has been so long since I felt the soft skin of a woman next to my body," I whispered as I began to caress her. "Your breasts and back and legs all feel so marvelous to me right now."

Megan responded by pulling me closer to her and pressing her beautiful breasts against my chest. "Judging by the way you keep poking me with your big friend down there, it's pretty clear that you're enjoying the experience."

Eventually we made our way back to the steps of the pool and I pulled her close to sit on my lap. I wrapped my hands around her breasts, and the two of us sat silently as we watched the stars. When Megan realized how late it was, she started to step out of the pool to get dressed again. I told her that she was in no condition to drive after all the margaritas she had downed, so I convinced her to spend the night in one of my guest rooms. We both dried off and we got her hair as dry as we could, and then I showed her to the guest room. She mumbled something about the fact that she did not have any pajamas with her, but I assured her that if she had been able to swim with nothing on all evening, she would have no trouble sleeping in the same way.

When I looked in on Megan a few minutes later, she was already fast asleep. She was lying on her back half covered by the sheet, and her right breast was fully exposed. I stripped off my sleeping shorts and slid into bed next to her. It felt so good to have a beautiful naked female in bed with me. I peeled back the sheet to reveal her full body, and I gently placed my hand on her breast. Megan's skin was so soft, and for a few moments, I closed my eyes and tried to imagine that it was Allison next to me. When I was sure that Megan was still asleep, I began to gently massage one breast, and then lightly slide over to do the same with the other. Megan stirred slightly but gave no indication that I should stop.

After a few minutes, I began to slide my hand down her abdomen to the silky soft skin near her navel. I let the tips of my fingers make small circles around her stomach as I watched her face for signs that she might be waking up. Emboldened, my fingers continued to move down her abdomen until I felt the first wisps of her downy pubic hair. Still no visible reaction from Megan, so I continued further until I felt the soft contours of her labia. At this point, she stirred again, but did not protest, and so I began to slide one finger into that warm inviting place between her legs. I moved slowly at first, but as I started to feel her juices begin to create some natural lubrication, I slid my finger deeper into that delectable slit.

I knew I had Megan's attention now because, even though she did not open her eyes, she began to make some soft moaning noises and her body began to move slightly with each probe of my finger. I added a second finger to the erotic assault and began a more rhythmic massage as I tried to keep time with her body movements. Within minutes, I could sense that she was fully aroused and nearing orgasm, and so I leaned over and began to kiss her breasts as I continued to stroke her love bud. Her nipples were erect, and I could tell that she was very sensitive to the touch of my lips. At this point, Megan seemed to be in the throes of multiple orgasms. Her legs clenched tighter on my hand and when I thought she might be sated, I started to pull back my fingers. She clenched her legs even tighter, and I could tell that wanted to sustain that feeling for a few more moments. Eventually she pulled away and we both rolled back over on our backs. Megan's eyes were still closed, but she had a satisfied smile on her face. I heard her whisper quietly, "That was amazing. I've never had a man do that to me before."

After a few moments, I was about to sit up and let Megan sleep peacefully when I felt her fingers on my chest. She played with my chest hairs for a short time and then began to trace the contours of my lower abdominal muscles. Her fingers slid even lower as she slowly ran her hand up and down my thigh. At this point, I began to think that either Megan was an expert cock-tease trying to drive me crazy with anticipation or just an inexperienced young woman who was not sure what to do next. Hoping that it was the former, I whispered that her soft fingers felt amazing and that she was free to explore some more. Whatever the motivation, I felt her fingers slide over to my scrotum.

As she tentatively massaged my balls, I had the suspicion that she had never done this before with a man. Buoyed by my quiet moans, she ventured further and began to slide her soft fingertips along the length of my shaft to the tip of my cock and then back again. As she continued this pattern of massage several times, I was going crazy with the sensation. I had not felt this hard for months, and now my satisfaction was literally in the hands of a young woman who had not even seen me naked until this evening. I feared that she might tire of the experience and give up, but instead she intensified her attention to my rock-hard cock until I could hold out no longer. I climaxed dramatically and sent spasms of cum over her hands and my chest.

My heart was still pounding, but I rolled over to get close to her and I whispered in her ear. "You have brought me more happiness and pleasure than I have felt for many months. I think we have begun to explore the possible depths of our companionship. Are you still comfortable with the thought of spending time together with me?

"All I did was touch your penis with my fingers. I thought a guy could never be satisfied unless his wife or girlfriend was giving him a blowjob or screwing him."

"All acts of sexual contact bring pleasure to a man," I explained. "Allison and I realized early on in our relationship that sexual pleasure is one of the greatest gifts that God gave us. We both agreed that we would be foolish if we did not take full advantage of that gift. I enjoyed every time that Allison let me inside her or placed her sweet lips on my cock, but the most intense pleasure I have ever felt is when a woman first touches my throbbing penis with her fingers."

"So I did all right then?" Megan asked with a smile.

"I think the answer to that question is still on your hand and on my chest. There is no faking an orgasm like that."

"In one night, you have already shown me experiences that I never dreamed I would have. I think I will be comfortable exploring some of the possibilities of an arrangement with you. You make me feel so comfortable and loved."

I had planned to return to my own bedroom, but it felt so good snuggling next to Megan. Before we knew it, it was morning, and we were both still lying in each other's arms. I went to the kitchen to make some coffee, and when I heard the shower running in the guest room, I brought two mugs back to the room. My guest room has a large walk-in shower with glass doors, and I stood for a few moments just watching Megan soap up her body. A few moments later, I was standing in the shower with her and exploring every inch of her body with my hands. She returned the favor. Her soapy hands felt marvelous on my throbbing penis, and it did not take long for her to bring me to another amazing orgasm. Megan did not object when I slid my hand between her legs, and I gently stroked her until she whispered that she could take no more. I stepped out of the shower to let her finish getting clean, and I went to my room to get dressed.