My ex-boyfriend taught me how to be a great sex partner. I did not know how important those skills would be on my new job on a sailing vessel.
PLEASURE CRUISE
Introduction - I work for a boutique hotel that has both a land property and a sailing vessel. The land hotel is located on the shore of Lake Como in Italy. It is in a quaint village right on the shore. It is open year-round but I only work on the sailing vessel and only during the sailing season. I am a college student (wink, wink) the rest of the year.
Part one – Learning curve
I got involved with the sailing industry thru an old boyfriend. He was a few years older than me. We met by chance at an art opening that I was helping a friend manage. His family had money. He overwhelmed me with attention and fun. After we had dated only a few weeks, we flew to Italy where he took me to Lake Como for a month. I was just out of high school when we first met, so I was quite young and innocent. He was trying to impress me, and he did. We sailed for a week on a small sailing ship and later stayed in several hotels along the shoreline of Lake Como for the rest of that month. It was a glorious trip.
My boyfriend taught me all about sex since I was a novice. I was not a virgin, but I was not well versed in how to please a man. He taught me all the ways to make a man happy. He instructed me on the best techniques for giving a blow job. There was a lot more to it than I ever knew. No wonder I never had a steady boyfriend. I did not know the basics of how to suck a dick. They should teach a course of that in High School. Maybe the dropout rate would decline.
Another trick he taught me was rimming his asshole. This would be considered part of the blowjob, so I learned it at the same time. I loved rimming his ass, for some reason. It was so decadent and nasty. I particularly love doing it after he has had a run or played tennis. I like the musky scent of a man’s sweat, and it really gets me going when my face is down there, buried in his crotch. I love having his balls nestled into my face. When I shove my tongue up his ass, my nose is right under his taint. I don’t know if that is a real word, but it is the area between his balls and his butt hole. It is very sensitive, and I love to run my tongue along the area. I nuzzle and lick it as part of my rim job.
If I have the time, and am feeling frisky, I will wet a finger and ease it into his butt hole while I suck his dick. My boyfriend loved me to insert multiple fingers after I got him nice and ready for it.
He also showed me his tricks for getting me off too. Much of what he loved me to do to him, he would likewise treat me to. One thing, of course was him rimming me. I loved having his tongue in my ass. He would bury it inside me, and it felt amazing. Then he would begin inserting fingers, one at a time, until I was fully stuffed with his manly digits. This was usually a precursor to anal sex. He would get my asshole completely loosened, then crawl up behind me and ease his big prick in my back door. I loved the preparation he made to get me ready, and I began to crave his manhood inside my ass. Anal sex became my favorite. My poor pussy didn’t get much action, other than preliminaries. All the finals were performed in my butt.
There were other kinks that this boyfriend introduced me to. He loved to slap my clit as I lay on my back, with his dick in my throat. My legs were spread, and my cunt was open and vulnerable. He really got off on spanking it. He would never warn me. I would be concentrating on sucking his cock; trying to relax my throat muscles so I could more easily deep throat him and would feel a fiery slap of his hand on my cooch. He might repeat it 3 or 4 times in rapid order before I could fully react. I hated it at first but then began loving the sting and vibrations that emanated from his assault. Whenever he slapped my cunt, I would jerk and groan, sending new sensations to his dick when it was lodged in my throat. I learned to climax just from him swatting my cunt, if he did it fast and hard enough.
Another kink that I learned to love was piss play. We would do this in the shower after a long, nasty sex session. He would stand over me as I sat in the tub, and drain his bladder all over my hair, face and in my mouth. I learned to love the salty, tangy flavor of his piss. It made me feel dirty and nasty, which was a sensation I never knew I loved until I met him. I would usually have to rub out another orgasm after he pissed on me.
As wonderful as all his introductions to the pleasures of sex were, my boyfriend had his bad side. After we returned from that Italian trip, he would go away for days at a time and not explain why or where he went. In some social settings he would be rude and condescending to me. He was very domineering. I loved that and hated it at the same time.
By the end of that summer, I was ready to start college. I think my boyfriend looked at me going to school as an opportunity for us to break up, so we said our goodbyes. He was ready to find a new girl to train, and I had enough of his control. We never kept up with each other after we said goodbye.
Part two - On my own.
I began attending college that Fall. But I really felt out of place. With my experiences in Europe and Italy, and the brief life I had been exposed to over there, college life was just not very interesting for me. I finished the Fall semester, then temporarily stopped college. I found a waitress job and worked full time to earn money to get back to Lake Como. That was where my heart was.
I had made good contacts with the owner of the hotel where my boyfriend and I stayed at on the lake. The owner hired me to work on a different sailing ship, much smaller than I had been a passenger on. This vessel had only six staterooms and a different clientele on board that the type of passengers I had traveled with. It was familiar to me yet odd to be on the service side of the travel industry.
This vessel catered to some very rich people, of course, who either own their owned companies, or their family did. These passengers seem to have no concern about money or spending it. They just wanted to have fun. After hours, on this vessel, I soon found out that they had a lot of extra activities going on. Since I was part of the crew, I was also part of the organized entertainment on the vessel.
My official jobs on this vessel were as a waitress, and a maid. I kept the staterooms tidy as a maid and waited on the passengers at mealtime and for cocktails. I had been given a uniform to wear. It was a short, black dress with a frilly white apron in front. The neckline was scooped very low, and my breasts were nearly always about half exposed. I do not own a bra, and I did not know what the ship’s captain would think about the fit of this uniform. It concerned me how it was exposing me. The other girl, Melody, who was the second waitress has the same issue with the uniform, and we both just learned to put up with our tits nearly popping out when bending over to serve a plate or a drink. The passengers sure loved my costume, and nearly everyone complimented me on it, even the lady passengers. I can tell when a woman is interested in another woman, and I learned later that we always had several of those lady passengers on board each trip. They were a welcome change to the horny men who were typical for the passengers on this vessel.
Part 3 – Poker night
The first night after our cruise departed was poker night. This was a great way for the passengers to get to know each other, and to mingle and bond. There was a large table set up in the ship’s central room for the poker game. There were four men and one woman playing this night. The lady was young, beautiful and based on her attitude, she was a free-spirited person, I would say. The drinks were being steadily consumed, and it was me and Melody’s job to keep them coming. I had a trayful for the table and as I would bend to serve each one, my breasts tried to escape their confinement. I didn’t really care, since I knew the tips would be fantastic from these passengers. I would flirt and accidentally rub my chest against the back of the men as I leaned over to bring a fresh drink. It was quite fun to get paid to be flirty. The captain smiled and made it a point to encourage me.
There was an interesting twist to one of the card games. The game was “strip poker by proxy.” To play the game each player put $1,000 into the pot in the center of the table. They played a typical poker hand, and the winner of that hand got to choose which person (it had to be a female) in the room had to remove a piece of clothing. The person chosen got to keep the $1,000 in the pot. So, the lucky person was literally being paid to strip. I was all in for this, and I was happy I had been so flirty. Besides me and Melody, the one lady passenger at the table who was playing told us she wanted a chance at the money too. So, I had a one in three chance of being asked to remove a piece of clothing. Not bad odds for me.
The first hand was over, and the winner chose the lady passenger who was playing to remove a garment. She feigned shock and outrage about having to remove a piece of clothing but then stood and slowly took her shirt off. She wore a bra, and pants, so was still not exposed any more than when wearing a swimsuit. She quickly scooped up the 5 grand that was on the table.
Another 5 grand was thrown into the center of the table. The drinks were flowing. And the hand was won by one of the men I had been flirting with constantly. He knew I did not have on a bra and told me I was the lucky winner. I smiled broadly and untied the white apron I was wearing. Everyone frowned, thinking it was part of the dress. I teased everyone by tossing it on the table. I looked around the table as if to get permission to take the money. The winner gestured for me to do so, and I was suddenly $5 thousand richer.
The game continued. There were several rounds played and each of us women who were serving or playing the game were evenly ***********ed to remove more clothing. Since Melody and I only had our apron, dress and our panties to lose we were at a disadvantage compared to the lady playing poker who had been free to wear more items.
After one of the later hands, I was chosen to win the pot, and it meant I had to remove my black dress. I asked the man who ***********ed me to win the pot to do the honors and unbutton the back of my dress. I turned to the table and shook it from my shoulders. It fell from my shoulders and hit the floor. My breasts wiggled as I shook them loose from the dress. My nipples instantly got hard from being exposed. I could not help but grab my breasts and squeeze them.
As the game went on the lady player was down to bra and panties, and she had a killer body. No wonder she had no hesitation to play, since she probably works very hard to keep in shape. Plus, she was making serious money by being willing to strip.
After a few more hands, the other waitress and I were now only wearing our panties. I noticed Melody had a distinct wet spot in the crotch of her panties, which made them virtually see-thru. I wondered it I was exposed in the same way. I certainly felt wet down there.
I don’t think the captain wanted the lady player to be topless, so he ended the game. He used the excuse that it was not fair to his waitstaff to be nude on the first night of the cruise. The other players lightly grumbled but laughed about it. They seemed to know more about the meaning of “on the first night of the cruise” than I did. I was happy to pocket a lot of money from this game. The funny thing was, I had no pockets. Ha-ha.
Part 4 - Daytime fun
We anchored off the shore of a secluded beach the next day. All the passengers dis-embarked by inflatable boat and landed on the beach. Me and the rest of the crew went ashore with food and drink. We were allowed to wear swimwear today. I had on a very tiny bikini that barely covered me. We fixed a meal and of course set up a portable bar to serve drinks.
A volleyball net was set up and the passengers all were playing. They did not have enough players, so Melody and I were invited to join. We had a wonderful time, and all got shit faced drunk as the afternoon game went on. Someone suggested we take a break and cool off in the blue water of lake Como. Of course, everyone went skinny dipping, and we joined them. I was in the water and instantly surrounded by several of the men who had been playing volleyball. I was groped and felt up by everyone and did not care. It felt great to be part of the fun.
When we were tired of the water antics, we all went back on shore. I found towels for everyone, but did not bother to put on my bikini since everyone else was still naked. I wanted to be a part of the action. One of the guys, pulled me aside and asked if he and I could sneak off. I knew what he was suggesting but was not sure I was allowed to do that. The captain saw our conversation and gave me a thumbs up. So, we found a secluded spot.
The man spread out a towel and I crawled on top of him. I began kissing him and found his erection with my hand. I slithered down and used my mouth to pleasure him as I had been taught by my old boyfriend. The guy I was with went crazy when I used my full technique on him. I loved licking his balls and his butt hole. When I used my fingers to play with his asshole he came in my mouth with a huge discharge of sperm. I love eating cum and when he finished his climax, I collapsed next to him on the towel. When he caught his breath, he returned the favor and licked my cunt until I also had a wonderful climax.
His cock had recovered by then, so he positioned me on my knees and speared me with his lovely cock. I could feel him spread my cunt lips with his tool. He pounded me with abandon. He pulled out and swabbed my asshole with my cunt juices and used that hole until he exploded inside me with another tremendous orgasm. I could feel every spurt of his jizz as he filled my ass with his load. We both collapsed and rested on the towel. I kissed him goodbye and said I needed to get back to work. I put my bikini back on and began serving more drinks until we all packed up and headed back to the ship. It was a wonderful day in the sun.
Part 5 - Private fun
It was only the second night of the cruise, and I was already exhausted from the trip. Having to tend to the staterooms, and be a waitress was tiring. The captain cornered me and asked how I was doing, and I told him it was a great job, but I needed a few hours to recover. He led me to his quarters and told me to take a shower and relax. I jumped in the shower, but soon he was in there with me. That was not the kind of break I was looking for but was not about to refuse the captain anything he wanted. So, we played in the shower for a bit, then crawled into his big bed. I fucked his brains out, knowing that was what he was after. Then I crawled off him and took a nap. He let me sleep until it was dark outside, so I gathered my uniform and got dressed. It was time for the evening meal, so I went back to work bringing drinks to the passengers. I could feel the captain’s jizz draining from my cunt as I bent over to serve drinks.
Thankfully, this second night was more subdued. Many of the passengers had too much sun and so the dining area was nearly empty. I was relieved since it was easier for me. Another passenger, an attractive lady named Jane, had been on the beach with us and asked me over for a private conversation. She was curious about my job and how long I had been doing this work. I told her this was my first time. She said she envied me, being so young and beautiful and having this kind of job. We had drinks together and continued our conversation. She then boldly asked me to come to her room. I was just drunk enough to agree, even though I thought it might get me in trouble. In the back of my mind, I hoped it might help me get a big tip at the end of the cruise, but I would have done it anyway.
When I went to Jane’s stateroom, she was wearing a shear gown that was floor length. She was naked underneath it. Jane was an elegant woman who had a husband with her on this voyage. She was almost in tears when she said he was no longer interested in sex with her. She was disappointed since she thought this trip would rekindle his romantic feelings. She admitted that when we played volleyball, she got very turned on by watching me. She was hoping to get me in her room while her hubby played cards again tonight.
I told her I was grateful for her kind compliments and took her face in my hands and gave her a deep, slow kiss. She melted in my arms, and we fell into the bed. She crawled on top of me and soon we were both naked. We kissed each other and then she began sucking on my breasts. She took my nipples in her mouth and expertly teased them as only another woman can do. I found her wet gash with my fingers and penetrated her with several fingers. I moved down to her steamy crotch and lapped at her inviting cunt. Her clit was swollen and tender. I kissed it gingerly as I pushed my fingers inside her. She gasped and moaned. I continued to fuck her with my fingers, and she grabbed my wrist and forced my entire hand inside her cunt. I fisted her with a fury, and she had a huge orgasm.
She then crawled on me just as her hubby silently entered the stateroom. He was surprised to see her naked ass pointed at him and her face buried between my legs. He motioned for me to be quiet, and he stripped down quickly. He positioned himself behind her hips and shoved his erection into her without her even knowing he was in the room. She lifted her head up from my cooch with a surprised look, then saw his reflection in the mirror. She smiled, then went back down on me. Her husband rammed his dick into her which caused her face to pound against my clit. I was on the verge of an orgasm the entire time he ravished her. I could hold it off no longer and had a monstrous climax. That may have triggered him to cum and he dumped his spunk inside her. She then climaxed again as she felt his load fill her cunt.
The three of us lay there in the afterglow of wonderful sex. Then I got up, kissed her goodnight and slipped out of their room. I hope for the rest of the trip, that they fuck like newlyweds. I am here to help. I stumbled back to my room, still naked, and slept like a baby.
Part 6 – The auction
There were only two of us who were waitressing, Melody and me. We had gotten to know each passenger almost intimately. When you see a person naked on the beach or drunk and frisky on board the ship, you kind of feel like you know them well. The last night of the voyage we were all in the ship’s main room again. The drinks were flowing, and Melody and I were very busy. The captain stood up and announced that there was to be a “charity” auction. And he spelled out the rules.
Melody and I were called up to stand with the captain. He said that due to the intimate nature of our cruise we were going to end the trip with a fitting night of decadent fun. Melody and I were to be auctioned off to the highest bidders. All the money was going to us. We were the “charity”. Maybe that was going to give the winners a tax write-off, I don’t know. We were to be the property of the high bidder for the evening. This was news to me, but Melody seemed to know all about it. I decided to play along. If she could do it, so could I.
The passengers were all hooting and chanting for the auction to begin. The captain first took bids for Melody. There were frantic bids with large dollar amounts being offered. She was amazed at the interest for her. She and I just looked at each other in stunned silence. The bidding for her ended, and cheers went up. It turned out that the winner was the same guy I had fucked on the beach. He must be a horny bastard. Lucky girl. The man came up and claimed his prize. Melody took his arm, and they went back to the table where he was sitting.
My turn was next, of course, and the bidding again was quick and frantic. Every man but the one who bought Melody was bidding like crazy. Even some of the ladies were in on it. I had no idea what prompted all the interest but was elated by their attitude. The bidding for me went astronomical. I could not believe what a person was willing to pay for a night of fun. But money was not the driving factor, it was the prestige of being the “winner”. It seemed to me that Melody and I were really the big winners. I would have fucked any person in the room for free, given the chance, but now I was going to get a huge payday from it.
The man who kept bidding for me was someone I had not had any real contact with. For the entire cruise he kept a low profile, so I was surprised he was so adamant about winning me. My pulse was racing the entire time. When the bidding ended, he stood on his chair, like Rocky, and held his arms up in victory. Wow. I had a lot of expectations to fill, it looked like.
I stepped from the captain’s side as Frank, my winner, approached. I gave him a very passionate kiss and then took his arm, and we sat down at his table. We got acquainted and someone brought each bid winners a giant bottle of champagne to celebrate the event. Frank and I toasted ourselves and had a toast for the captain as well. It looked like it was going to be a fun evening. Then, I was surprised when a wheeled platform was rolled into the room. The tables were pushed back to make room, but all the passengers stood near the platform. I assumed we would go to Frank’s stateroom, but not just yet. The auction was not over. The captain hopped up on the platform and addressed the room. He said, “The winner of each girl has the honor of disrobing them as we stand on the platform”. I was stunned. It is one thing to be drunk and skinny dipping with everyone, but this was an intimate setting, and the guests were all fully dressed and just a few feet away. I felt the color drain from my face as I stared at the crowd. Melody was nervous too, but she apparently had been through this before on a previous cruise.
My bidder, Frank, slowly stood in front of me as did Melody’s winner. Both men carefully unbuttoned our uniforms. Then they pulled them off us and handed them to another person. We were both just standing there, in front of everyone, just wearing panties. Thank goodness for the champagne I just drank which helped remove my inhibitions. Melody’s bidder then carefully put his fingers in the elastic of her panties and pulled them down to her ankles. She calmly stepped out of them. Frank followed and I was soon bare naked too, in front of everyone. My gash was very wet, and I could feel my moisture running down my inner thighs.
Then, both Melody’s bidder and Frank unzipped their pants and tossed them away. What the hell? Frank had an instant erection. He indicated that I should get on my knees and suck him off. I blindly followed his direction and instantly swallowed his cock, balls deep, in my mouth. I was more relaxed once I started working on his lovely cock.
The crowd was silent as Melody and I fellated our high bidders. I could tell there was movement in the room but was totally focused on the prick in my mouth. I wanted this to be his best blowjob ever. Soon, Frank began to make gurgling noises and was beginning to pulse in my mouth. I knew he was close to cumming. He pulled out and jacked his hard-on furiously with his fist and blasted a bucket of cum on my face. I was caught by surprise and did not capture any of his jizz in my mouth like I intended, and my face was drenched with cum.
Melody had the same thing happen to her. Her bidder pulled out and shot a load of spunk on her face too. She was dripping with his sperm. The audience began cheering and applauding. Then I noticed we were no longer alone on the platform. Other men had removed their pants and were standing in line to get their turn to cum on our faces. Apparently, that was the plan from the beginning. Everyone had pooled their money to get the auction prices high enough to get us on the platform.
I turned to the next man closest to me and began sucking his erection earnestly. He stroked my hair as I deep throated his member. Everyone in the room could see what an excellent cock sucker I was and soon he pulled out and blasted my face with more cum. This happened repeatedly until Melody and I had serviced every man in the room. The captain was last and offered his raging erection to me. I latched on to it like it was the last dick I would ever get to suck. He face-fucked me until he was ready to blow his load. Since I knew what to expect, I leaned back on my heels and let him coat my face with jizz. There were even a few ladies who got in on the action. Two women hopped up on the platform, naked, and rapidly diddled their clits until they spewed their juices on our faces. It was a decadent and glorious conclusion to the auction.
Frank led me, practically blinded by the spunk on my face, to his stateroom. I was still naked, of course, and could feel gobs of cum dangling from my chin. It felt so deliciously dirty to have everyone’s spunk on me. He led me to the shower and gently cleaned me up. Then we crawled into his bed. I was able to give him my full treatment and wore his asshole out as I tongued and fingered him to another momentous climax. He then laid me down and serviced my needy cunt until I had a glorious orgasm. We fucked like teenagers until we were both exhausted, then fell asleep. Sometime during the night I woke up and gave Frank another blow job. Then we slept until late the next morning. I don’t know if Frank had a wife or a girlfriend with him on this cruise, but the topic never came up.
The vessel was due into port that afternoon. I had time to get back to my quarters and freshen up before I had to tend to the passengers. Everyone was enthusiastic about seeing Melody and me after last night’s event, and I was greeted warmly by all the men and the ladies too. I was surprised. I would have assumed some jealousy from spouses, but I guess they all knew and were in on the game. Frank, it turned out, did have a wife with him on the trip. She came up and hugged me generously. She said I made Frank’s world when I went back to his room with him. It was something he had dreamed about. I told her how lucky she was because he was an excellent lover. She winked at me and said, “I know”.
I had a private meeting with the captain after all the passengers were off the ship. He told me I was an incredible crew member, and he wanted to see me again on the next cruise. He handed me a check from the auction. It was an astounding amount. And then he gave me a check for my salary and tips. Another huge check. After that, I told him I was ready “to cum aboard, Captain, for the next cruise!”