Somebody Fucked Up - Pt. 01

Finally, the day of my trip was here. I couldn't wait to get on the plane and head down to the islands for a week of rest and relaxation. All I kept thinking of was being by myself.

My name is Debbie and I am 40 years old, single by choice and, if I must say so and I will, not hard on the eyes.

The flight to the island was going to be about three hours which gave me a chance to browse the brochures of the hotel and what was available to do while I was there. The place looked amazing. The chalets were on the beach and spaced out for privacy which was perfect for me because I like being naked when I am taking the sun.

The plane must have caught some tailwinds because we arrived earlier than expected. The resort had sent a car for the guests and transported us to the hotel. The ride was short and the place looked fantastic as we approached it. We piled out of the car and went inside to check in.

Several minutes later, I was being taken to my chalet. It was beautiful from the outside. It was very private as the chalets were spaced a good distance from each other to afford privacy. There was even a six foot high privacy fence on each side of the patio with the ocean view directly visible from the patio. There was even a hot tub.

I went inside and unpacked and noticed there were some clothes in the dresser. I figured the previous guest left them. Then I heard a man's voice, "Hey, what are you doing and why are you in my chalet?"

I looked up at the loft and there was a guy standing there. "Who are you and what are you doing here?"

He came down and introduced himself as Roger. I told him my name. Then we checked our hotel papers only to find out that the hotel booked us both in the same chalet for the week. We looked at each other and headed to the front desk.

I said to the clerk, "Excuse me but you have booked me and this gentleman in the same chalet for this week. Please fix this now.

The clerk looked at us and said, "I can't. There are no chalets available. We are completely booked."

Then Roger said, "So, what do you suggest?"

The clerk told us to wait while she got the manager. A few minutes later the manager, a Ms. Larson arrived. The clerk advised her of the problem and then I asked her what she was going to do. She hesitated for a second and said, "First of all I want to apologize for this mess. The next thing I want to do is make things right for both of you. That being said, your stay here will be on us. That will include meals, drinks and even excursions."

I replied, "That's fine but what do we do about sleeping arrangements?"

She replied, Since we have no chalets currently available, I'm afraid you two will have to share the chalet until another one becomes available. Right now that is the best I can do. The other option would be for one of to cancel your stay here and of course there will no charge and you can return anytime and your stay will be on us."

I looked at Roger and said, "Thank you but we will be back once we make a decision."

And then we left and went back to the chalet. Once we got back I started crying from disappointment. Roger said, "Look, don't cry. This is an easy fix. I'll cancel my stay and come back another time."

"I can't let you do that. It's not right. There has to be another solution."

"Well, we could get married." As he laughed

"That's not funny."

"Listen, we are both adults so why don't we share the place. It won't be so bad. There is a bed in the loft I can use and you will have the bedroom."

"I guess that would be ok, but I like being naked and I was hoping to take the sun that way."

"So do I. Look, you still can. I can be somewhere else when you take the sun and when I'm sunning you can be somewhere else. We can work out a schedule that is good for both of us."

"That could work. We could try it. What do you say Roger?"

"I say we should stay and enjoy ourselves."

"I agree. Let's go tell Ms. Larson."

We went back to the reception desk and saw Ms. Larson and told her we would be staying. She told us just to sign for everything and she will take care of it. We thanked her and went back to the chalet.

Over some wine, we came up with arrangements that seemed like it could work out. After we got everything settled we decided to go out for a stroll around the grounds. As we strolled we got to know one another and even shared some laughs.

I found out that he was single and 41 and never married and owned his own business. I told him I was 40 and single by design. He told me that he never had time to get serious with a woman but would like to.

We walked up and down the beach and decided to have dinner together at the hotel restaurant. By the time we got back to the chalet it was time to get ready for dinner.

"Roger, you want to shower first?"

"Whatever you want. I can wait."

"No. Go ahead. I'll wait until you're finished."

"Ok."

As Roger was showering I picked out the dress I was going to wear...a short black one that showed a lot of cleavage since I wasn't going to wear a bra.

"Shower is all yours Debbie."

"Thank you."

And then I headed to take my shower. I wasn't long and as I came out of the shower Roget saw me wrapped in my bath towel. "Hey, you look pretty good in that thing." As he laughed.

"Thank you sir. Now please get ready while I get ready.

A short time later we were both dressed and all set to go when Roger said, "Wow Debbie, you look fantastic."

"Thank you Roger. You look pretty good yourself."

We laughed as we walked to the restaurant. The dinner was terrific...plenty of it and the wine was excellent. It was even better knowing we didn't have to pay for anything. After quite awhile we finished and headed to their lounge for some dancing. I was beginning to think that this whole fucking mess may not be so bad after all.

We had some drinks and Roger asked me to dance and I accepted. He wasn't half bad either. Finally, it was time to head back to the chalet. When we got in we said our good nights and Roger went to the loft and I went into the bedroom. I got out of my dress and put on a white tank top to sleep in to go along with my thong. Then I went into the bathroom to brush my teeth and as I was doing that, I heard a noise and turned to see Roger standing there.

"Oops. Sorry." Roger said.

"No problem. I'll be right out "

I hurriedly finished and vacated the bathroom. As I was exiting, I looked back and couldn't help but notice how fit Roger looked in his briefs.

That night I was a little restless in bed and tossed and turned until I finally fell asleep.

The next morning I woke up early, showered and put on shorts and tank top leaving off my bra as I wanted to be comfortable. Just as I finished Roger came down, said good morning and headed to the shower. I heard the water running and my curiosity got the better of me and I managed to peek through the edge of the door which wasn't completely closed. I watched as he showered and gasped when I saw him as he turned my way. He had a cock that was bigger than I have ever seen. I quickly moved away and went outside to get some air.

Awhile later, Roger came down in shorts and a t-shirt. "Are you ready to go get some breakfast?"

"As a matter of fact, I am. Let's go."

As we walked to the dining room he asked if I had any special plans for the day. I told him that I hadn't made any. Then he said, "Look, if it's ok with you, we can take a cruise to the other island and do some snorkeling. That is if you want to."

"Thank you for asking. That sounds like fun. I was just going to lie around and take some sun, but yeah I'll join you."

He called the front desk and asked what time the boat was going to leave and he was told it would go in 30 minutes. So we both hurried up and got into our suits and headed to the dock just in time. As we we were going to the island I realized I put on the wrong bathing suit. I put on a white bikini that wasn't lined, one that I used for tanning and one when wet, my breasts and pussy would be almost completely visible. The trip took a half hour to get to the island where we anchored. There were three other couples on board. We were told we had all morning to snorkel and then we would have lunch on the beach before heading back.

Roger and I snorkeled together and the water was crystal clear and it was just fabulous. Before we knew it, we were on the beach getting ready for lunch. I tried to cover myself up up with a towel but it just wasn't working so I said to myself...just fuck it...if they want to look, let them. Then I dropped the towel.

We had lunch then headed back to the main hotel. On the way back, Roger and I chatted and I thanked him for a great time. When we got back I took a shower first then Roger. It was late in the afternoon so we just relaxed on the patio with some island drinks. Then Roger said, as he smiled, "I don't want to be crude or rude but now we are both even."

I looked at him and replied, "Excuse me, but what are you talking about?"

"This morning...when I was showering...I noticed you checking me out. And at the beach, after we finished snorkeling, we are even now."

I turned a beet red and replied, "Oh...you saw? I apologize. I hope you can forgive me."

"It's no big deal. I hope you liked what you saw though." As he smiled, he continued, "I know I liked what I saw today."

I blushed, "I wore the wrong suit today. I use that one for tanning. I'm sorry."

"Don't be. I enjoyed the scenery."

We both laughed and had another round of drinks.

"What are your plans for tomorrow?"

Roger replied, "I was just going to take the sun."

I told him I was thinking about doing the same thing. "Did you have a particular time?"

"No. What time were you going to?"

"Right after breakfast."

"Ok. I'll do the after lunch time."

"Unless...."

"Unless what?"

"We take the sun together?"

"Together? Are you serious?"

"Yes. Only if you promise to behave yourself."

"My dear Debbie, what kind of a guy do you think I am?"

"A gentleman, I assume."

"Ok. Then tomorrow after breakfast we sun."

We both laughed and watched the sun set over the water. God, this was so beautiful. I was glad I decided to stay.

The next morning we went to breakfast which was delicious and then headed back to the chalet.

"Roger, I'm going to get ready to go out to the patio."

"Ok. I'll be down shortly."

I went outside in a short terry robe and removed it and laid on the lounge looking out over the ocean, the sun beating down on my nakedness. A few minutes later I heard, "Here I come, ready or not." And Roger came out naked and sat on the lounge besides me. Neither one of us making a comment about our nakedness. It was like we were wearing bathing suits.

We enjoyed the sun and a few drinks until it was time for lunch.

"Hey Roger, it's lunchtime. Want to get something to eat?"

"I was thinking of ordering from the restaurant and staying here. What do you think?"

"That sounds good."

So, Roger called the restaurant and ordered some food as we remained naked on the patio. It wasn't long before the food was delivered and Roger and I are on the patio, naked. As we were eating I thought to myself...I don't really know this guy and I'm out here, naked having lunch with him and I'm enjoying it.

We chatted over lunch and finally finished. Then Roger said, "Doesn't that water look so inviting?"

"It sure does. It's so blue."

"Let's do it then."

"Do what?"

"Go for a swim."

"Debbie to Roger, we're naked."

"I can see that. Let's go skinny dipping."

"But somebody might see us."

"Roger to Debbie, we just met and we're naked together. Let's get wet."

He got up, took me by my hand and we ran naked to the water and jumped in. I couldn't believe that we did that but it felt so fucking good. We were in the water awhile then we decided to get out and head back to the chalet. I was waking in front and turned back to see where Roger was and when I did, I saw his cock was almost erect. I quickly turned away and kept walking until I reached the patio.

When we got back I told Roger I was going to shower and get dressed and go for a walk. He told me was just going to continue taking the sun.

About 45 minutes later I was walking along the shore taking in the sights. Out in the ocean I could see dolphins playing and it was a magical moment for me. Then my mind drifted back to seeing Roger's partially erect cock. Now, I've seen men's cocks before, after all I am 40 and have been with men, if you know what I mean, but his cock fascinated me. I don't know why. My imagination was running wild as I pictured myself in bed with him fucking me. I tried to get the image out of my mind but I couldn't and I didn't know what to do.

Some time later, I was back at the chalet and Roger was just getting up from sunning. As he got up he didn't see me but I saw his fully erect cock and I knew then that I wanted it. I made some noise and yelled out so he had the opportunity to cover up his erection. To my astonishment he didn't cover up and now we were face to face and his hard cock was in full view. He realized it and quickly tried to cover up.

I laughed and said, "Too late."

His face turned a beet red as he said, "Oh Debbie, I'm so sorry. Forgive me."

"No need to. I enjoyed the view." As I smiled and walked away.

Nothing happened the rest of the day and we went to dinner like nothing ever happened. Dinner was great as was the wine. After dinner, we strolled the resort holding hands when he said, "Debbie, I want to apologize for earlier today. Please forgive me."

"No need to forgive you. I've seen hard cocks before. I am not married because I haven't found the right man but I have been around. And, if I found the right guy, I would never let him get away."

"You know Debbie, I just never found the right woman, what with my business I have never had the time but I can honestly tell you that I like you and hope you like me."

I must have blushed as I stammered out, "I do like you Roger. These last few days have been terrific thanks to you."

"Same here."

Over the next few days we got to know each other a lot more. We did have a lot in common and were very comfortable talking about various subjects. The funny thing was that we both decided to shed our clothes indoors, something that surprised me.

The next to last night we were walking on the beach under a full moon when we stopped and he pulled me toward him and he kissed me. I returned his kiss and I could feel his hardness through his shorts.

Then I said, "Roger, let's go back to the chalet."

"Is there something wrong?"

"Everything is perfect."

We walked back and on the patio we hugged and kissed and I whispered, "Let's go inside."

We went inside straight to my bedroom.

"Are you sure Debbie?"

"Never more sure of anything Roger."

We kissed and undressed and got into bed. We made love the whole night and I enjoyed every minute of it.

The next day we had breakfast delivered and as soon as we finished we were back in bed fucking. God he was so good. I must have had dozens of orgasms and he filled both my holes and mouth with his warm cum, much to my delight.

On our way to dinner we stopped in at the front desk and saw Ms. Larson and I said, "Ms. Larson, Mr. Holmes and myself would like to stay an extra week. Would that be possible?"

Ms. Larson smiled and said, "It just so happens that I just had a cancellation and you will be able to stay the week."

I looked at Roger and as we walked out I said, "If you think the last two days have been good, you are in for a real treat."

He looked at me with a big grin...

Look for Part 2

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