This past Fall we decided to take an impromptu trip to the Big Island – Hawaii. We had not been in years and decided it was a wonderful way to escape from a busy year. I made reservations at a beachside resort on the island's west side and asked Deb to make sure she had several new and sexy swimsuits.

We decided to do a pool day after a refreshing night of sleep. The view was incredible! We got two chairs facing the pool with the ocean in the background. This was a Tuesday morning, so it was not very crowded, and we laughed about getting up early to get chairs when we did not need to. I ordered a drink and we sat and soaked in the sun, view, and relaxation. We spent the rest of the morning working on our tan, cooling off in the pool, and having drinks – by lunchtime, we were starting to have a surprisingly good buzz and ordered lunch.

After lunch, we reclined on our chairs, and I planned to spend an hour or so catching up on some reading. After about twenty minutes, we were interrupted by a middle-aged man asking us a question.

“Is anyone sitting in this chair? If not, would you mind if I camped here?” he said to Deb and me sheepishly.

I looked up and saw a mid-forties man in swim trunks and a t-shirt. He was fit, had a decent tan, and seemed to be alone. As no more chairs were facing the beach, I said to him, “Not a problem with us! We have been here all morning, and the views are amazing!” 

He sat down next to Deb in the chair and began to settle in. I introduced Deb and I and he told us his name was Chad. I asked him how long he had been in Hawaii, which started a pleasant conversation.

“I’ve been here two days – we’re having an annual planning session this week and I had a free afternoon so I decided to catch some pool time,” he said.

“Wow, tough place to have to work!” Deb said to him. “Did you get to bring your wife?” she asked.

“No, I’m not married anymore. Divorced about three years and enjoying traveling and meeting new people with my job,” Chad said. He told us he was a sales executive and traveled regularly so he had plenty of opportunity to do all three.

Chad took off his shirt, and it was pretty evident he worked out regularly. He was solidly built, and I saw Deb giving him a lot of “side-eyes” while he was settling in.

“Chad, what do you do for fun when you’re not working?” I asked him.

“Well, I run quite a bit as I am preparing for my first marathon, and I also play softball with some buddies when I am in town,” Chad replied.

Deb laughed and said, “Running and I don’t agree – I used to run when I was younger, but I can’t deal with the sore muscles afterward!”

“I have the same problem,” Chad replied, “but I have a masseuse that has taught me quite a bit about how to take the pain away – that’s how I survive!”

Being the horn dog that I am, I was already starting to think about what these two together in our room would be like, and Deb already had an interest. Since we had both had a few drinks in us I decided to give it a test.

“Deb, I am going to head back up to the room to shower and relax a bit before dinner tonight. Why don’t you relax out here for a while and I’ll see you back there later?” I said, looking at her lying there in her bikini and feeling no pain.

“Ok, I think I will stay here for a while and finish my tanning session,” she said. I said goodbye to Chad and told him we would see him around later.

I grabbed my things and headed back to the room. I could already feel myself getting an erection thinking about those two sitting there together and what might be. Once I got back up to the room, I opened our sliding glass door to let in the cool breeze and get a view of Deb and Chad down at the pool. They had not moved, but I could see that they were chatting back and forth while they absorbed the rays. I stripped down and jumped in the shower to wash off the lotion and pool, stroking myself thinking about Deb getting hit on by Chad. Once I got out of the shower and dried off, I walked over to the balcony to see what was happening below me.

Surprisingly, Deb was lying on her stomach and Chad was applying sunscreen on her back and legs! He was sitting up in his chair and I could see he was enjoying the view of Deb’s side boobs and ass while he applied it. He was pointing to certain spots on her back and legs, and I assumed he was talking about pressure points and muscle locations. He finished rubbing in the lotion and sat back. Deb turned over and proceeded to apply lotion to her shoulders, chest, and stomach while they talked. I could see Chad’s eyes watching every move while she applied the cream, so I knew he was enjoying the view! I decided to masturbate watching the two of them interact, having visions of Chad taking Deb in the pool. It didn’t take me long to cum, and I cleaned up before Deb got back to the room.

Deb came back to the room about forty-five minutes later, and she was both tipsy and flustered. I asked if she enjoyed her time at the pool and she said she did. I then asked her if she liked hanging out with Chad, and Deb replied, “He is a nice guy! He’s funny and has an interesting life story…I enjoyed talking to him.”

She stripped down and jumped in the shower to get ready for dinner. I told her I was going to walk down and confirm our dinner reservations and would be back shortly. As I was walking through the lobby, Chad was going in the opposite direction up to his room. I said hi and he told me he enjoyed talking to us at the pool. I told him we planned to spend the morning there tomorrow, and Chad said, “Tomorrow is my last day here and I plan on being there as well – maybe I’ll see you there!”

Sex that night was hot, with Deb getting extremely aggressive and coming hard several times. I asked her if she was thinking about Chad when she was riding me and she just smiled and said, “He is pretty hot, but I’m focused on you!.” 

The next morning, we had a quick breakfast and went out to the pool for another relaxing day. As we walked to the lounge chairs, we noticed that Chad was already at the pool and had two chairs next to him that were empty. He saw us walking up and said,” Good morning, you two! I came down early and grabbed a couple of extra chairs in case you decided to come by.”  Deb had a big grin on her face and thanked him for being so thoughtful. She sat down next to him, and I took the chair on the other side.

Deb took her time applying sunscreen and disrobing down to her bikini. We were all talking while getting comfortable, but I could tell through my sunglasses that Chad was eating up the activity happening in front of him while she got situated. We all ordered drinks and sat there talking and laughing for the next hour or so – not feeling any pain and letting the sun and great weather relax us. Chad began telling us about the research he had done on sports massages and how they are used to eliminate pain and discomfort from workouts. He seemed knowledgeable about technique and was even pointing again to several spots on Deb’s back and legs that were key massage areas.

I joked to Deb, “Tell Chad about those leg cramps you have been having!”

“Those drive me crazy!” Deb replied, reaching down to her calves and thigh, and rubbing them,” I always seem to get them after I work out and I thought it was dehydration.”

Chad replied, “It could be that, but could also be just irritated muscles. Do you mind If I touch them?”

“Sure,” Deb replied, “If you can make this go away I will owe you!” 

Chad smiled and moved over next to her chair while Deb turned over on her stomach. He lightly pressed on her legs with his fingers, then moved them circularly on the muscles. I heard Deb lightly moan as she said, “Yes, right there is where it always is sore.” Chad moved up her leg using the same method and I could tell it was effective for Deb based on her reaction.

“It’s hard to get the right leverage and position from these chairs, but that is generally the technique I use anywhere that there is soreness or tenderness,” Chad said as he sat back.

“Deb, did you feel like it helped you? Maybe Chad could do a session for you before he leaves?” I asked with an ulterior motive in mind.

“It helped, but not sure how we would do that?” Deb replied.

Chad quickly responded, “I have a couch in my suite that would work if you are interested, but it’s really up to you.”  It was obvious he had thought about it as his response was automatic.

Deb paused and then said, “Well, I don’t want to have you spend your last day here doing a massage session,” to which Chad replied, “It’s an opportunity for me to practice my technique and also help you out at the same time!”

I suggested we break for lunch and plan on meeting Chad in his room at 2 pm. Chad gave us his room number and told us he would meet us there. Deb and I went to the resort restaurant to grab a bite for lunch, and I ordered another round of drinks. Deb was very relaxed (as was I!) while we ate and talked – Deb did not seem to have any concerns with a private session with Chad, but she did ask if I were coming with her, and I told her I would if she wanted me to be there.

After lunch, we went back to the room to shower and dress, and Deb put on a short sundress with no bra. Her nipples were rock hard, and I did not know if it was due to the alcohol, the cool room, or her excitement about a massage session with Chad!

We walked over to Chad’s suite at the agreed time, and I knocked on the door. Chad answered and welcomed us in. The room was a genuinely nice-sized corner suite with a sitting area, a small kitchen, and a separate bedroom. Chad was in sweatpants and a tight t-shirt, and he showed us the suite including the sofa/settee that was accessible on both sides. We chatted for a bit, enjoyed the view from the window of the ocean, and then Chad asked Deb if she was ready.

“Sure,” she said, “would you like me to lie down here on the couch?”

“Why don’t you sit down first, and I will work on your shoulders to get started,” Chad said as he sat on the end of the couch. Deb sat next to him, and I just grabbed the chair across from them while he began on her shoulders and neck.

“That feels good!” Deb said, “You can use more pressure if you want,” which he did, and it was evident she was relaxing. She had put a light sweater on over the sundress and Chad asked her to remove that so he could access her neck and shoulders. She did remove it, and I sat there watching her nipples stick straight out through the sundress with my excited wife.

After working her shoulders, Chad asked Deb where she was having the most discomfort. She told him her lower back, glutes, and back of thighs were the tightest. Chad stood up and grabbed a large pool towel he had brought back with him and told Deb she could put this over her while he got some lotion. Deb asked, “Put the towel over my clothes or just the towel?”  Chad chucked and said, “Your call, but it’s easier to massage the skin than through clothing.”

Chad went around the corner to the kitchen and Deb stood up, pulled her sundress off, and wrapped the towel around her. I suggested she lay down on the couch and I would cover her, which is what she did.

Chad came back out with some massage oil and saw Deb lying on the couch with the towel draped over her and the sundress across the back of the couch and had a big smile on his face – he was having the same thoughts I was, and I winked and smiled at him as he approached Deb.

Chad asked Deb if he could remove his shirt as he tended to work up a sweat and it would keep him cooler – she had no issue with that and had her head turned away and eyes closed. Chad took his shirt off and went to work on Deb’s lower back with strong, slow, circular motions. To do that he had to lower the towel down to her ass, working her lower back and upper glutes. Deb moaned several times during the pressure, and both Chad and I had a splendid view of Deb's side boob as she raised her arms above her head. He was explaining what he was doing as he moved, and he worked his way up to her upper back and shoulders. Deb was getting very relaxed and commented several times on how good it felt.

Chad told Deb, “I can work your shoulders and back easier if you are on your side. Would you like to turn towards your husband, and I will work from behind? I can get you another towel if you want to cover up.” 

Deb immediately turned to her side, and I was looking at both of her 36D breasts fully exposed. Chad sat behind and over her working her shoulders – I wasn’t that surprised how quickly and immodestly she adjusted as I could tell she was already turned on.  Chad had a magnificent view from above of her right tit and hard nipple as he worked that shoulder. I was already very erect and sat there massaging myself while he massaged her.

Chad moved to her arm and began to roll it between his hands. As he did this, the bottom of his hand brushed against her breast back and forth. Chad looked at me and shrugged his shoulders with a smile. I gave him a thumbs up and he saw I was hard and stroking myself through my shorts. He slid back and told Deb he would do the other side and stood up. Deb very slowly laid on her back with her tits fully exposed and she moved to the other side – this was going exactly where I had wanted it! Chad was looking down at her fully nude top and I could see he had a hard-on pushing against his sweatpants. Chad massaged her other arm with Deb lying on her side with her exposed breasts.

After a brief time massaging the arm, he stopped and sat up – and surprisingly, Deb moved to her back with her breasts in view for all to see! As her eyes were closed, Chad placed both of his hands on her breasts and slowly began to massage them.  Deb didn’t resist and moaned softly as he did this.  Her nipples could have cut diamonds they were so hard, and he gently rubbed around them as he massaged her.

With a grin, Chad said to Deb, “Massaging pectoral muscles is one of my specialties.”

“You’ve had some experience there!” Deb replied.

“Would you like me to continue?” Chad asked hopefully.

“Absolutely – I’m feeling very relaxed now,” Deb answered. As she did she slowly moved her hand to Chad's leg and began to rub up and down through his sweatpants. Her hand moved further up with each stroke until she touched his now very erect cock. “It looks like you need a little massage and stress relief yourself,” Deb purred as she wrapped her hand around his member.

Chad was sitting back on his haunches and closed his eyes while she stroked him through his pants. Deb was still covered in the towel from her waist down and he reached over and pulled the towel off as he lowered his head down to Deb's nipples. He very gently licked around her areolas and nipples before gently sucking on them. Deb moaned loudly and placed her hand on his head. While Chad devoured her breasts, his hand moved down between her legs, and he quickly found her wetness as Deb jerked from the contact on her pussy.

Deb whispered to Chad, “If I am not dressed you can’t be either.” Chad quickly sat back and pulled his pants down exposing a long and fat cock. He was fully shaved, and Deb grabbed his member and began stroking it slowly, massaging his ball sack when she reached the bottom of his shaft. Chad was enjoying it immensely and thrust into her hand with each stroke. So that he didn’t come too quickly, Chad stood and moved to the end of the couch, where he was standing directly between Deb's feet.

“I’ve wanted to taste you since we met!” Chad said as he moved her legs apart and kneeled in front of her dripping cunt. Slowly he kissed the inside of her thighs and worked his way up to her wetness. I thought Deb was going to scream when he touched her clit, and she pulled his head further into her pussy as he lapped up her juices. Too quickly, Deb started to arch her back and I could tell she was on the verge of coming. With a shudder and a loud moan, she came on his tongue, pushing against his head while the waves of ecstasy hit her. Chad continued to slowly finger her pussy while kissing her inner thigh as she came down from her orgasm.

Deb sat up and said to Chad, “Ok, now it’s my turn,” and pulled him gently onto the couch while she moved to the floor. Leaning back, Chad put his hands behind his head as Deb leaned over and licked and sucked on his nipples. She kissed and licked down his stomach until she got just above his cock. She began to slowly stroke it and spit on it to lubricate him while she moved her other hand down to massage his balls. Very slowly Deb took his head into her mouth and ran her tongue around it before making a loud slurping sound as she took his shaft more fully in her mouth. Now it was Chad’s time to moan, and he pushed up into her mouth to get her to take more.

Deb took half of him in her throat and gagged slightly, then allowed the saliva to drip from her mouth to his cock. She hungrily took his erect penis in and out of her mouth, using her tongue around it as she pulled it out. Chad had placed his hand on her head and was encouraging her to go faster and I assumed he was ready to come. Suddenly, he stopped and told her, “As much as I want to come in your mouth, I want to see myself in your pussy.”  He pulled her up on the couch and flipped himself over on top of her. From where I was sitting, now with my cock out and in my hand, I could see them from behind – his body standing between her legs, which she was wrapping around him.

I saw him rubbing his head up and down her wet slit and then ever so slowly moving it into her welcoming snatch as she moaned and pulled him closer. Deb had her legs wrapped around his waist, and Chad was slowly moving in and out of her. Deb was massaging her breasts and playing with her nipples while he fucked her more quickly. Normally we would have asked him to have a condom on or to pull out, but I heard Deb tell him, “Chad, I want you to come in me!”  That made him start to pump harder and I saw him tense up and bury his cock in her, emptying his load deep inside Deb. He stroked slowly for a moment before he pulled out.

They both looked over at me as if they had forgotten I was there! I had deposited a big load in my lap watching this happen and was just slowly stroking myself watching them come down.

Chad commented, “I needed that badly, Rick, and you are one lucky guy. Thanks for letting me experience her!”

I laughed and said, “She chose you, not me. I enjoyed watching her be pleasured. We should all stay in touch and get together again!”

We chatted some more as everyone got cleaned up and dressed, and we said our goodbyes after exchanging contact information. Chad was leaving early the next morning, but we planned to connect again on the mainland. I fucked Deb several times that day and she was wet and willing every time – we are both looking forward to the next encounter with Chad!