Thursday evening my man and I found ourselves at our favorite restaurant for Dollar Oyster Raw Bar night. We sat at the bar and chatted with the locals as we ate. Most of them are snooty assholes, but some are characters we have come to know and like or tolerate. This brings us to Captain Tom, who is always very excited to see us and boasts about his life as a seaman. My man still has no idea that Tom and I have been lovers. Tom played it very cool. Personally I think the man is a pompous ass as he is very confident and bold. 

As the night wore on and the wine disappeared, Tom invited us out on his boat the following Sunday, weather permitting. I was quick to say yes, but my man was looking for excuses to not go and said he had plans even though they were not solid. Tom asked if I could come alone and that others had also been invited. I said yes and asked for directions, even though I already knew the way. Tom asked my phone number saying he would text directions and times. I gave him my number. He proceeded to text me the word “Hello”. 

My man didn't care, he knows I like to suntan and tease men and love to let other men know what he thinks is his alone. Little did he know that Tom and I had previously had sex. A few minutes later Tom sent another text. It was a photo of his cock with the note, "I know you miss this."

I returned a message with a picture of myself naked and another note, "What do you think?”

Smirks were exchanged between Tom and I as the night wore on. On the ride home, my man discussed how big of an arrogant ass Tom was, but nice enough to have me on his boat. We talked about how being on his boat with other people like him would be fun, which aroused us both and we went home to a night of awesome love making till we fell asleep cuddling. 

Sunday arrived and my man was in a deep sleep as he didn't get home 2:00 AM. I awoke at 8:00 AM and got ready, shaved all the hair located below my head and put lotion on. I wore a tiny bikini with a shawl to cover my tiny bottoms and texted Tom. He responded quickly with instructions to be at his boat at nine thirty. He also wrote that he had a whole day planned for me. I was so excited I went on the Lush site to tell others I had fun planned, while masturbating until I came. 

I walked to the dock where I met Tom before and called for the launch. The boy in the launch pulled up I could feel his eyes devouring me as he brought the little boat alongside Captain Tom’s. Captain Tom reached down and pulled me aboard. Tipping the driver as he sped off, he picked me up and kissed me, squeezing my ass hard. 

Tom told me it’s going to be a long day and I was in for some fun. When I asked what he had 
planned, he told me I would soon find out. He disconnected his boat from the mooring and we began our journey. I took off my shawl and stood beside him as we sailed off into deeper waters. I leaned on him and felt his cock through his shorts, Tom smiled and asked me if I missed that cock. I told him I could not stop thinking about it. He pulled the rope of his shorts and they fell down exposing his beautiful shaft. He pulled my arm down and said, “Get on your knees and show me how much you missed it.” 

I fell to my knees and lifted it up and began kissing and sucking it as deep as I could. I was enjoying it as he pushed my head onto it, saying things like, “Suck it baby” and asking me if I loved his cock, all while I made slurping noises.

I told him “Yes.”

Tom told me I didn't need my top and untied it throwing it down as he sailed and I sucked away at his hard cock. I gave his balls and ass a little love as part of my ritual of sucking, which I know drove him crazy. 

He stood me up and told me to hold the wheel as he taught me how to steer the boat. Land was in sight, but far off in the distance. I enjoyed steering the boat, as he made some adjustments, then came behind me and helped me sail.

I felt his hard cock on my ass and pushed back into him. He told me to step out of my bottoms and as he slid my bikini off, he had me lean forward so I could still hold the wheel. He began kissing and licking my ass and pussy, which was already wet. I pushed back onto his face and moaned till he brought me to my first orgasm. 

He began fingering me hard and fast, asking me if I wanted him. I moaned 'yes' and he kept asking me to beg him. As I said, “Yes,” he didn't hesitate to slide in balls deep and begin really fucking me hard, while I tried to keep the boat going straight. I was just about to cum again when he beat me to it, filling me with what seemed to be a huge amount of seed. As he withdrew I felt it leak out. He fell out of breath back onto the seat. 

He told me he didn't want to start this early because he planned a surprise for me, but I was too irresistible. He cleaned us both up and we sailed on. I lay out on the deck and caught some rays as the sun beat down on my naked body, totally content with what just happened.

Tom came to a mooring and we began to have a naked lunch while rubbing lotion on areas before we got too much sun. It was around Noon so the day was only half over.

I was so relaxed and happy I nearly missed the sound of a motor pulling alongside our boat. I grabbed a towel to cover up when I heard a loud female voice yell “Permission to come aboard Captain Tom!” 

I covered up and saw Tom help a blonde and a guy on to the boat. I then recognized them as Cindy with her loud yenta voice – arghh. Cindy called out to me and waved and her husband Stan, with a huge evil grin, waved as well.

Part of me wanted to leave as this was a couple from town that I saw regularly at the beach, the market, and of course the restaurant. Cindy came up to me first and saying, “Oh My God, she's already naked.”

Tom and Stan were in conversation as Cindy was driving me batty by pulling at my towel. That all ended when Tom said, "This is how it’s done," and yanked the towel from me for their eyes to see.

I poured another glass of wine and sat down as Cindy began to play with Tom’s cock. It seems they were familiar with what was happening, since Tom told me that all three have dreamed of having me for over a year now. 

Tom wasted no time barking out orders telling them to get naked. I didn’t have much say in the matter as my submissiveness to Tom and the wine took over. Tom spread me open and played with me to show Stan my beautiful pussy, then instructed him to go down on me, which he did. Cindy barked out that she could taste me on Tom’s cock and so it began.

Stan was in his 60's and on a Viagra high. His average cock and saggy balls were ready to go while Cindy had huge fake boobs. She was well kept for her age, probably late 50s, having come from old money and looked good. 

She moaned as Tom was fucking her hard, watching Stan moan a thank you as he licked me all over. Tom soon pushed Cindy over to me and she traded places with her man, going down on me as Tom continued to bark out orders while enjoying the party he created. Stan was in my mouth with the look of ecstasy as I deep throated him and his wife stuck her fingers and tongue in me. Cindy told her man to go on and fuck me.

"Fuck her Stan, you've dreamed about it now go on and do it!" she demanded. 

Stan moved me around to put my legs on his shoulders and he entered me. For his age, I will give him credit, he pumped and sweated till he couldn't hold back and he came inside me. I showed concern and Cindy ensured me he had had a vasectomy then proceeded to lick Stan's cum out of me. Her long nails actually hurt me and I tried to pull away, but Tom was hard again and ready, pushing her face down on me and entering her ass. She moaned and couldn't concentrate on me, so I pulled away and watched Tom pound her till he came in her ass. They all laughed and relaxed and drank wine naked on the boat. 

We took the boat out further and Stan was still hard from Viagra. Cindy pulled me on to her and I let her begin to kiss Stan as they rubbed me all over and Tom steered the boat. Cindy seemed to love my vagina more than I did, she couldn't stop licking or fingering me. Stan was back but a little more forceful, taking me doggy style. Stan told Cindy to get under me sixty-nine and I had my first taste of Cindy. She wasn't bad tasting at all. Stan drilled me as hard as he could slapping my ass in time with his wife licking me.

Stan asked, “What your husband would think of me and my wife fucking you?” I came. 

I love that and I don't know why, but when I'm made to feel like I'm cheating or dirty, it makes me cum. I didn't even have time to say no when Stan entered my ass. It hurt. Some lotion and my juices were the only lube involved. He didn't last long before he came again and Cindy helped clean me up as I got her off. 

I was exhausted and wanted to go home, but Tom wasn't done with me. He got Stan to steer and picked me up and slid me down on his hard monster cock as Cindy helped me balance. He rocked me back and forth and all I could hear was her voice saying, “Isn’t his cock amazing.” Cindy kept telling Tom to fuck me until it ended with Tom bending me over part of his boat. 

After Cindy added lube he began to really fuck my ass hard and it really hurt. I know how happy it makes him, so I let go as he pounded away for what seemed like forever till he came loudly, almost blacking out on top of me. 

I felt great and horrible at the same time, Tom reminded Stan and Cindy not to tell my man or anybody in town. They swore, as hugs and kisses were exchanged. I was told I made Stan's dream come true and Cindy promised to play with my man if it should be required. I know my man wouldn't touch her, but it was nice of her to offer. 

After docking and getting home, I was sore and the sun had taken its toll. I wanted to relax. I ran into the shower and was in there for at least thirty minutes. I knew my man wanted details, so I told him who was on the boat and he felt bad for me. That night I blew him till he fell asleep so he wouldn't touch me since I was sore and tired. 

Sailing is fun… 

I don't know if I want to go back out with Tom.

Move to... New folder

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To understand this journal entry you must read the first Captain Tom story. 100% true.