My name is John, and I own a large sailboat. I make my living taking wealthy clients on Caribbean cruises. My 18-year-old daughter helps out with food service, general maintenance, and cleaning rooms. She has worked with me for three months since she graduated from high school. I'm divorced, and my ex-wife had no problem with Ashley joining me on my sailboat for the summer.

On the first cruise with Ashley, my life was turned upside down. Four wealthy executives and their wives were enjoying a vacation cruise on my sailboat. The men were all in their forties, divorced, and enjoying the cruise with their younger wives.

On the second day of our cruise, I overheard Ed during breakfast, when he was joking with his friends - Joe, Doug, and Dexter.

His buddy, Joe, was laughing and looking at Ed’s wife, Julie, in her skimpy bikini when he said, “I think our wives should all go topless on our cruise. Let’s enjoy ourselves. Julie, why don’t you start the show and remove your bikini top?”

Julie looked at her husband and said, “I’m okay showing off my tits, as long as Ed doesn’t mind.”

Ed shrugged his shoulders and answered, “Why not? This will spice up our vacation, that’s for sure, and I do enjoy seeing naked tits.”

Julie stood up and casually took off her bikini top. She has a sexy body with voluptuous tits, and obviously enjoys teasing men. Her husband, Ed, didn’t seem to mind that his wife was topless in front of his friends.

The other three wives (Jane, Carol, and Nancy) all laughed and removed their bikini tops.

Ashley and I watched the four topless women confidently showing off their naked tits to the men. I have to admit I enjoyed seeing the topless wives.

The weather was perfect with a light breeze and calm sea. Our passengers enjoyed the cruise, laughing and joking with each other. Ashley served beverages and snacks to our guests.

We sailed into a nice cove with a beautiful beach. Our guests all jumped into the water and waded over to the beach. Julie's large tits were flopping and bouncing as she walked. The other three wives had sexy bodies with smaller tits.

Ashley and I straightened the boat, cleaned the breakfast dishes, and made the beds.

Ashley asked me, “Dad, is it normal for the women on your cruises to go topless? I was surprised that all the wives took off their tops in front of their friends. All the husbands got to see the naked breasts of their friends’ wives.”

I chuckled and answered. “Ashley, it’s not unusual for our guests to relax on vacation and lose some inhibitions that are normal in everyday life. Our clients on this cruise seem to be pretty adventurous. It’s our job to make them comfortable. The better job we do, the higher the tips will be when they all leave.”

Our guests returned to the boat after spending two hours on the beach. They all went to their cabins to freshen up for dinner.

We served dinner at 7:30 PM. Everyone was dressed casually. It was obvious that none of the women bothered putting on bras. The outline of their nipples was obvious in rather tight casual tops. Julie wore a sheer white top with her nipples prominently on display.

We served a lot of wine at dinner, and our guests drank more than they should have. The conversation over dinner was somewhat inappropriate. Ashley and I couldn’t help but overhear all the joking.

Joe sat next to Julie and teased her the most. He was drunk and said, “Julie, you are blessed with amazing tits. I think we should visit the wild side of life and switch partners on the cruise. I’d like to fondle your tits and spend the night fucking you. Ed can spend the night fucking Jane. What do you say? Should we swap wives for the night?”

Holy shit. I didn’t know what to expect. I thought Julie was going to slap Joe in the face for suggesting they swap wives. But that’s not what happened.

Julie was also drunk and giggled as she answered Joe, looked at Ed, and said, “Why not? I’m horny and find it really naughty if we switch and fuck each other’s spouses. Let’s do it.”

This turn of events was completely unexpected. I'd never had swingers on my sailboat, which is what I now saw unfolding. Carol giggled and said, "I think I might be interested in swapping with Dexter and Nancy. I've always wondered what it would be like to have a big black cock slide into my wet pussy. We all know Dexter has a massive black cock."

Nancy laughed and answered Carol, saying, "I don't mind sharing Dexter's massive cock with you. But be careful what you ask for. You know the saying, once you go black, you never come back."

Ashley and I watched in amazement as Joe and Julie paired off, followed by Ed and Jane, Carol and Dexter, and Nancy and Doug.

I didn't know what to say, and Ashley didn't say anything either. We cleaned up after dinner, and I suggested that Ashley and I sit on the boat deck and share a glass of wine. I got a chilled bottle of Chardonnay, and we proceeded to the chairs on the deck.

Once we each had a few sips of our wine, Ashley looked at me and asked, "Dad, did I just see our clients switch wives and go to their cabins to have sex with someone they aren't married to? I've heard of wife swapping and swingers, but never knew people actually had sex with people they aren't married to, with the approval of their spouse. I don't know what to think of this, other than to say it's obviously very naughty behavior."

I was stunned, but answered Ashley, saying, "I am just as surprised as you to see our clients switch partners and go to their cabins to have sex with someone they aren't married to. I've heard of this behavior, but seeing it actually happen is a bit surreal."

Ashley and I finished our wine and headed to our cabins to think about what we'd just witnessed. I found myself aroused by the turn of events, knowing Julie was going to fuck Joe and knowing that Carol was going to be fucked by Dexter's big black cock. My cock was erect and hard, so I jerked off with very nasty images in my mind. I made a mess with the jism spewing out of my cock and going all over the bed.

I didn't know what Ashley was thinking. I knew she wasn't a virgin, and she had fucked at least two boyfriends over the past 2 years of high school. I tried not to think about it, but we all know that teenage girls with serious boyfriends consider sex a normal course of events.

The next morning would be interesting. We had breakfast ready at 7:30 AM as we waited for our guests to gather. They all appeared at about the same time, holding hands with their fuck buddies from the night before. Julie was topless and wearing a thong bikini bottom. All I could think of was, WOW!

Everyone seemed surprisingly relaxed. Nancy broke the ice, looking at Carol and asking, "Carol, did you have any trouble getting stretched out by Dexter's massive black cock? I enjoyed fucking Doug, but have to say it did feel different to have a smaller penis in my pussy."

Carol laughed and answered Nancy, saying, "I was so wet with anticipation that Dexter's big black cock easily penetrated my pussy. I'm on birth control, so I didn't have any worries when he unloaded a massive load of creamy cum inside me. I felt like a slut being serviced by a black stud. Dexter fucked me three times during the night, and again about 30 minutes ago before we came to breakfast."

Holy shit, I was embarrassed beyond words knowing that Ashley was hearing the dirty, nasty details of Carol getting fucked by Dexter. Oh well, it is what it is.

After breakfast, we sailed into a port where I needed to pick up supplies. The women were all topless and enjoying the sun as we sailed on calm waters. Once in port, I took the dinghy to the dock to shop and pick up supplies.

Ashey stayed behind to clean up after breakfast. When I returned about an hour later, I was shocked to see my daughter on a lounge chair, sitting with our guests. I was even more shocked to see that she was topless for the old men to ogle her. What the fuck? I knew Ashley had a bikini in her cabin, but she had conservative casual clothes to wear on board with the guests.

Ashley wears small bikinis, just like her friends, at the pool. As a Dad, I'm always embarrassed when Ashley wears skimpy bikinis in front of me.

Ashley saw me pull up to the sailboat and came over to help with the supplies. I didn't know what to say. I had never seen Ashley topless. It was not something I wanted to see, especially knowing the four old men on our cruise were seeing my daughter.

As I got onto the sailboat, Ashley blurted out, "Dad, I know what you must be thinking. I'm sorry I've surprised you with me going topless and letting our guests see me. I am embarrassed you are seeing me topless.”

She continued, “You said we should do everything we can to make the cruise enjoyable for our clients. Dexter asked me to join them on the deck and suggested I put on a swimsuit, assuming I had one. I had my bikini, so I went to my cabin, put it on, and joined them to lounge in the sun. When I walked up to the group, the men all whistled and gawked.”

Ashley continued to explain and told me that Julie told her that she'd never seen a body as sexy as her body. Dexter smiled at her and encouraged her to take off her bikini top.

Ashley was embarrassed as she tried to explain the current situation. She said. “All the men urged me to remove my bikini top. The women also encouraged me to join them topless. I want to please our clients, so I removed my top. I was a little embarrassed with older men seeing me, but I also admit it was liberating. I’ve never done anything like this.”

Dexter walked over to talk to me. He hesitated and then jumped in, saying, “John, I’m the one who encouraged Ashley to join us in a bathing suit. When we saw her amazing body in a tiny bikini, we all wanted to see more. I talked her into going topless.”

Dexter continued, “I’m sure both of you are embarrassed. A Dad doesn’t want to see his daughter topless in public. A daughter certainly doesn’t want to be topless in front of her Dad.”

Ashley tried to smooth things over and said, “I’m the one causing the stress. Let’s all accept it and move on. I’m topless in front of my Dad. I'm on display for everyone to see. I’m going to get a glass of wine.”

The tension didn’t disappear, but Ashley’s confidence and attitude helped.

I put the supplies in the cabinets and joined the group on the deck. Ashley was holding her own as she chatted with the old men and their topless wives. I poured myself a glass of wine and sat in a lounge chair.

The conversation was graphic at times when the four couples talked about having sex with each other’s spouses.

I got up and told everyone I was going to prepare dinner, leaving my topless 18-year-old daughter with a group of wife-swapping adults.

This was only day three of a seven-day cruise. My head was spinning as I contemplated how things would play out, and what role Ashley might play with a group of horny adults on vacation.

Everyone dispersed and went to their cabins around 5:00 PM to prepare for dinner. Ashley came up to me and said, “Dad, I’m sorry if I embarrassed you. I know things took a sharp turn when Dexter convinced me to go topless. Let’s move on. Think of me as another guest or employee and not your daughter.”

I smiled and said, “That won’t be easy, but that’s a good suggestion. As my employee, let’s get dinner ready. Take a shower and put some clothes on for dinner.”

We had a pleasant dinner with normal conversation. We shared several bottles of wine, and everyone was relaxed.

After dinner, Dexter suggested we all sit on the deck and have more wine. I excused myself and went to my cabin. Ashley joined our guests for more conversation and wine.

I would not have been happy at all if I knew what was going to transpire that third night in the Caribbean.

—————

I’ll let Ashley tell you about her last 4 nights and days of our cruise. I was the crew. Ashley was the entertainment.

This next section is from Ashley.

—————

Hello everyone. Ashley here. Going topless on the cruise was never anticipated. When Dexter convinced me to wear a bathing suit and join his group, I knew trouble could follow. My tiny bikini didn’t cover much of my body. I knew the older men would be aroused when I appeared in my tiny thong bikini. And that’s the understatement of the year.

I reluctantly took off my bikini top when the men all but begged to see my naked tits. I felt liberated and aroused when I exposed my tits. My nipples were erect, and I knew the men would get aroused when they gawked at my tits.

When I sat down with a glass of wine, I was the center of attention. All eyes were glued on my all-but-naked 18-year-old sexy body.

Joe summed up what everyone was thinking when he said, “Ashley, you have an amazing body. I don’t think your Dad will be happy when he sees you decided to go topless and expose your amazing tits to us horny old bastards.”

I decided to stake my ground and set the tone of our interaction. Like all cute, attractive young women I know full well what men are thinking when they see naked tits.

I smiled at the group and said, “I’m not sure what might happen over the next four days, but I do think there is a possibility I might allow one or more of the four horny men, who are getting aroused looking at my naked tits, to fuck me. Let’s all just play it by ear."

Joe raised his glass and said, “I’ll propose a toast to the possibility that Ashley will allow me to insert my hard cock into her tight young pussy.”

All the men raised their glasses and simultaneously said, “To Ashley and her tight young pussy.”

The conversation was graphic at times when the four couples talked about having sex with each other’s spouses. I asked Julie, “How did it feel when a man other than Ed penetrated your pussy with his hard cock? Were you aroused and excited as he fucked you? Did you have an orgasm?”

Julie started laughing when she answered, “Ashley, you are a real piece-of-work. Good for you. I loved having another man fuck me. I felt like a teenager getting fucked for the first time. I’m sure you know what that’s like, being only 18. Tell us about your experience when you lost your virginity. I’ll bet that was when you were 16 or 17. Did your boyfriend wear a condom or did he dump a load of creamy cum inside your pussy?”

I felt horny when I answered, “I lost my cherry when I was 16. The details will have to wait for another time. We have four days to have more drinks and continue our inappropriate, naughty conversation. I see my Dad is coming back, and I'll have to face the music when he sees I'm topless and hanging out with our guests."

I was very nervous when I walked up to greet my Dad. I could feel my tits were bobbing and jiggling as I walked, and I wished my Dad wasn't watching. But I knew I had to face the music.

You've already read my Dad's version of what happened when he returned from shopping. We dealt with the situation as best we could. I returned to the group, and we hung out until dinner time.

So, we can return to me getting ready for dinner. I knew I would join our guests after dinner for more drinks, and I also knew my Dad would clean up after dinner and go to his cabin.

It was about 9:00 PM when I joined the group of wife swappers for more drinks. I was happy I had smoothed things over with my Dad, as best I could.

Julie led our discussion after dinner. She smiled at me and said, "Let's pick up where we left off. We all want to hear how Ashley lost her virginity when she was 16. This will be fun."

I chuckled and answered, "I know you're all a bunch of perverts. I had a serious boyfriend at 16, and we fooled around like normal teenagers. He felt me up, I jerked him off, and we progressed to the point where we would get naked at one of our houses when no one was home. Tony wanted to fuck, but I wasn't ready. To please him, I sucked his cock and let him shoot his creamy cum into my mouth. He loved to see me open my mouth and show him how much cum I was about to swallow. I would smile and swallow his entire load of creamy cum."

I knew the men were all getting aroused by my story, so I continued, "The day finally arrived when I was ready for a hard cock to penetrate my tight pussy. Tony and I were naked in my bed. I spread my legs and told him it was time to fuck. He climbed on top, penetrated my pussy with his hard cock, and humped me like there was no tomorrow. He didn't last long, and he shot his creamy cum deep inside my pussy. I felt relieved that I was no longer a virgin, and we could fuck several times a week. We did fuck on a regular basis for the next 18 months or so, when it was time for me to move on and find another boyfriend. I was bored with Tony, and wanted to fuck someone else."

The entire group was staring at me. I had their full attention. It was time for some fun. I took off my top, unhooked my bra, and let my tits flop out. I looked at the men and said, "I want to see some hard cocks. Unzip your pants and let me see what you are packing. I want you to beat off. I'm sure your wives won't mind. They are all a bunch of sluts, so let's get on with some action. I can't wait to see Dexter's massive hard cock."

The men all followed my instructions and sat in their chairs jerking off. No one seemed embarrassed. The wives all took off their tops and sat in their chairs with their naked tits on display. When I saw Dexter's massive hard cock, I thought I was looking at a weapon. The other three men had average-sized cocks, similar to what I had experienced with my two boyfriends.

I went over to Dexter and knelt in front of him. I reached out and started stroking his big black cock. Everyone was watching me. Joe had his phone out, and I knew he was going to record me. I bent over and put my lips around the tip of Dexter’s cock, as I continued jerking him off. I licked his cock, but didn't let him put his full shaft inside my mouth. I could feel Dexter tense, and I knew what was coming. I took my lips off the tip of his cock, and said, "Dexter, I want your creamy cum in my mouth and all over my face. Let me have it all. I'm ready, and I want a real mess."

Dexter unloaded his creamy cum all over my face and into my mouth. Everyone was watching as I looked at them and swallowed. I took my towel and wiped the cum off my face.

I sat down and had a sip of my wine. Everyone was speechless. They stared at me like I was from another planet. Finally, Dexter said, "Holy shit, that was something I never expected. What's next?"

I smiled at everyone and said, "I want to fuck. We have four nights, and I'll fuck each of the horny men. One each night, I want to start tonight with Doug. I'll let each of you decide who fucks who tonight. I'll fuck Doug and then head back to my cabin. I certainly don't want my Dad to know what I'm doing."

The men had all put their cocks back in their pants and were ready to head out. I took Doug by the hand, and we headed to his cabin. Jane went with us, since they had decided this was the night for Doug to fuck Jane. Dexter was going to fuck Julie, Ed was going to fuck Carol, and Joe was going to fuck Nancy.

I was aroused and excited beyond anything I could remember. I was going to be fucked by a horny old man, who was going to put his hard cock into my tight pussy. Jane was going to watch Doug fuck me before he fucked her. This was really nasty, inappropriate behavior by all of us.

When we got to Doug's cabin, we stripped off our clothes. Doug’s hard cock was pointing at the ceiling. I sat on the edge of the bed with my legs spread apart. I was surprised when Jane came over, got on her knees, and put her head between my legs so she could lick my pussy. I’d never been part of a threesome and had never had another woman lick my pussy.

I felt Jane’s tongue enter my pussy. Doug sat on the bed and fondled my tits while Jane went down on me. This was all new to me. I felt my body tense, and I experienced an orgasm that was completely unexpected.

I pushed myself back on the bed as Doug positioned his hard cock at the entrance of my tight pussy. Doug rubbed the tip of his cock on my pussy lips, and teased me by easing his cock inside me and then pulling out. I needed a good hard fuck. I looked at Doug and said, “I need your cock deep inside me. Don’t hold back. Fuck me hard. I’m your teenage fuckdoll. I want your creamy cum inside my pussy.”

Doug didn’t hold back. He fucked me in a frenzy with his hard cock pumping in and out of my tight pussy. He fondled my tits as he fucked my wet cunt. I felt he was ready to orgasm, and wasn’t surprised when he unloaded his jism deep inside me. He collapsed on top of me, exhausted.

Jane had watched me getting fucked and said, “Ashley, that was a sight to behold. Wow. You are a fuckdoll. I look forward to fucking Doug, but I can’t compete with what I just witnessed.”

I giggled and said, “I’m happy that I’m part of your naughty wife-swapping club. I’ll wait until your last night before I let Dexter stretch out my tight pussy. Time for me to go. I’ll see you at breakfast. We have to be careful, so my Dad doesn’t suspect I’m actually getting fucked by his guests.”

The next morning was a little awkward for everyone. My Dad and all our guests had seen my naked tits. Our guests had all seen me give Dexter a blowjob, and Joe had a recording of Dexter dumping a huge load of creamy cum into my mouth and all over my face. And they all knew I had fucked Doug.

We were scheduled to spend the day sailing to another port, so it was a day for our guests to lounge in the sun.

I helped my Dad clean up after breakfast. We didn’t really speak. My Dad broke the ice and said, “Ashley, this cruise has become very awkward for me. You are a beautiful young woman, and I respect that you are old enough to make decisions I might not like. I want you to know I’m okay with you going topless for the rest of our cruise, if that's what you want. Obviously our clients are more than happy to see you. And I can’t argue that our job is to make our guests happy. So, why don’t you enjoy yourself and hang out with our guests?”

What a relief. I said, “Dad, I know I’ve embarrassed you. I’m sorry. I think I’ve set the stage for some big tips on this cruise. Let’s just consider me going topless as part of my job to entertain our clients.”

I went to my cabin and put on my bikini. I joined our guests sitting in lounge chairs on the deck. The four wives were all topless. I greeted everyone, smiled, and removed my bikini top.

I told everyone that my Dad was fine with me going topless for the rest of the cruise. I laughed and said, “To quote my Dad, he said it was my job to entertain the guests and make them happy on the cruise. I hope you will all give me a five-star rating when we return home.”

Everyone laughed, and Doug said, “I think you earned more than five stars last night. Since it’s your job to entertain us, can I put some lotion on your tits so they don’t get sunburned?”

I sat on a lounge chair and told Doug to help me out. He grinned and came over to spread suntan lotion on my naked tits. I felt really naughty as everyone watched Doug fondle my tits. Joe’s new job was to capture my naughty behavior with his phone.

I made sure everyone had plenty to drink. The cruise went smoothly; we had lunch, hung out, and chatted all afternoon. At one point, Doug and Carol said they were tired and wanted to get some rest. As they headed to their cabin. Carol asked me to join them. Everyone smiled and knew Carol had something on her mind other than getting some rest.

I joined them, also knowing Carol had something up her sleeve. When we got to their cabin, Carol giggled and said, “Ashley, Doug told me he really enjoyed fucking you last night. He said you were a real fuckdoll. I wish I could have watched the two of you fucking. I’d love to watch Doug fuck you, if you’re ready for round two?”

I smiled and pulled off my bikini thong as Doug stripped naked. His cock was rock hard. Carol looked at the two of us and said, “I’d love to see your tits flopping as Doug fucks you doggy style. Does that work for you?”

I gave Carol a solid thumbs up, climbed onto the bed, got on my knees, and presented my open pussy to Doug. Doug got behind me, positioned his hard cock at the entrance to my tight pussy, and proceeded to fucK me like a dog in heat. My tits were flopping uncontrollably. What a show. Doug thrust his hard cock deep inside of my pussy and let loose with a huge load of cum as his orgasm overtook his body.

I rolled over onto my back, exhausted. Carol came over to me and gave me a kiss. She fondled my tits and whispered, “Ashley, that was a great performance. I’m impressed that an 18-year-old, with almost no experience, can fuck like a professional porn star. You are a natural fuckdoll. Thanks for letting me watch my husband fuck you with enthusiasm and energy I didn’t know he had.”

I put my bikini thong back on and walked back to rejoin our guests on deck. As I approached, with my tits flopping, I gave everyone a two-thumbs-up. They all knew exactly what that meant, and gave me a quiet round of applause.

I don’t need to share more details with you, since you now know I’m a very naughty 18-year-old slut and fuckdoll. The next three days passed quickly. I was topless almost all day, other than meal time. I fucked Joe, Ed and Dexter over the next three nights.

Dexter stretched my tight pussy beyond anything I thought I could handle. His deep thrusts, and when he buried his big black cock inside me, were unbelievable. I fondled his balls as he thrust his cock in and out of my pussy. He really enjoyed that. He unloaded his creamy cum deep inside me. I felt like a whore, servicing a black stud, and loved every minute of my fuck session with Dexter.

When we returned to port, I wore my professional clothes, as our guests departed with their luggage. They were all smiles. I’m sure you don’t find that surprising.

One after another, they settled up their accounts with my Dad. All four couples told my Dad it was the best vacation any of them had ever taken. As a sign of their gratitude, they all told my Dad to double his fee as their tip for such a memorable vacation.

After they were all gone, my Dad looked at me and said, “Ashley, we both know those tips were remarkable, and I know you were the reason their vacation was so memorable. We have four more cruises booked over the next three months. I have no problem if you decide to join our guests in your bikini as we cruise the Caribbean. And, if the men want you to go topless, I’m also okay if you accommodate them. We both know that was the underlying reason for the huge tips we just got from this cruise.”

I gave my Dad a thumbs up and said, “I’ll make sure all our cruises are memorable, especially for the men, who we both know can be influenced by a young 18-year-old with a sexy body in a tiny bikini.”

That’s all for now. I’m looking forward to more cruises, more topless adventures, and more fucking.