Captain s ChoiceChapter 2 The Deckhand
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My Swinging Deckhand free porn video
My career was spent as the owner/operator of a 100' charter yacht in Alaska. It was a high-end operation and not cheap. It wasn't unusual to have 12-15 passengers and up to 20 crew members. Most of my customers over my 30+ year career at sea were at least in their 60's, and sometimes well into their 80's. They had to be well off as the trips lasted 10-15 days, and the daily rate was more than what some people would pay for a week on a large tourist ship. What all of them had in common was lots of money, and many of them were looking for thrills that had little to do with seeing the sights of Alaska. I had many older women sneak into my cabin (or Stateroom, as they are called on board), a few men, and some couples. And they tipped very well for my special services.
Occasionally younger couples would make a trip with me. Such was the case on one trip when a newly married couple joined the boat in Seattle for a trip up the Inside Passage, a famous route followed by most US fishing boats going through Canada to Alaska and back.
Janine was 23 y/o. She was maybe 4'11', about 90#, very pert and cute with a smile that would raise the dead. She was an avid hiker, runner, and SCUBA diver, and was in splendid shape. Her husband, Gene, had been on the swimming team at his university. Like his wife he had blonde hair and a dazzling smile. He was close to 6' and very buff.
As soon as they boarded the boat I knew two things: I wanted both of them, and I was sure it would happen. They were open, fun-loving, very sensual, and enjoyed the flirting I greeted them with.
On the third day of the trip we stopped and the passengers went ashore to hike and have a lunch my crew gave them. That was the perfect opportunity for me: I made it clear to crew and passengers alike that in keeping with Coast Guard regulations I had the right to inspect rooms and private luggage to make sure d**gs and weapons hadn't been carried on board. I knew everybody would be gone for at least two hours, so I immediately headed for Janine's and Gene's room. The early search through drawers was about what I expected: bikini panties, g-strings, not a lot of bras (she had very small breasts), tight pants, short skirts. But went I started through his belongings I had a surprise: he also had panties...a dildo...makeup, a wig...and leather leashes and handcuffs.
I got so hard I couldn't help myself: I took a pair of her used panties and stroked until I filled the crotch with a load of cum.
A day later we ran into some bad weather and I let everybody know that would we anchor in a protected cove until the weather passed. I also let Janine know that if she or she and Gene were up late they could feel free to come to the wheel house. I would be on anchor watch late in the evening, and they could join me for some wine and get to know each other better. I don't drink, but didn't feel the need to say so.
She came up to the wheel house by herself around midnight. Fifteen minutes later I had her sitting in the Captain's chair, legs over the arms of the chair, as I licked and sucked on her hairless pussy. After she came...she was a squirter, which really turns me on...I asked if she and her husband ever played together with others. She said they loved group sex, and had already talked about trying to seduce me. I laughed and told her I planned on seducing both of them as soon as I saw them. She asked what I liked. I knew what he had in his drawers, so I told her I was bi, loved a man dressed as a girl, etc. She told me to wait for them. About 30 minutes later they knocked on the wheel house door, and when I opened it there Gene was, wearing a tight short skirt, dark mesh nylons, a blonde wig, and very sexily made up, almost like the makeup had been applied by a professional. And around his neck was a leather collar, with a leash attached that allowed Janine to control 'her.' My cock was very hard, and she caressed it through my pants. He clearly liked seeing her play with me....and when she unzipped my pants and freed it, he licked his lips and asked to taste it. At first she said no, but then she pulled on the leash until 'she' was on 'her' knees in front of me. Then came the crowing touch: Janine pulled a set of handcuffs from her purse, and handcuffed Gene's hands behind 'her' back. Then Janine took hold of my hard cock, and told him to kiss my cockhead, and run 'her' tongue over it. Janine slapped his faced with my cock, and finally had me take my pants and shorts off so Gene could suck on my balls. Janine got back into the Captain's chair, and with her legs spread and her fingers in her cunt she told me to hold his head tight and fuck his mouth like it was a cunt. It was as good as any pussy that could be imagined, and when I finally came, so did Gene, filling 'her' panties with a huge load. After a few minutes to catch my breath, Janine had Gene guide me into her pussy and play with my balls and ass as I fucked her. She was so small and petite and young looking with her tight hairless pussy tight around the shaft of my prick my fantasies ran wild and as another load of cum built up the fantasies focused on incredible erotic ideas that are best not said here (for legal reasons!). Gene had been fingering my ass as I fucked Janine, and since I am a top I really didn't pay attention to what was happening as I was losing control....until I moaned and started pounding her pussy so hard and as I started cumming in her I realized that he had just driven his cock into my ass. His cock wasn't real big but the idea that he was dressed as a girl but was fucking me as I fucked his wife made me lose control as I had never done before.
It turns out that they had been boyfriend/girlfriend since they were about 15, and he had been dressing as a girl since he was much younger. They came from wealthy families and were able to play all around the world. We had a delightful trip together. He never fucked me again because he would dress and be 'my girl' and I got to fuck him almost anytime it was safe. She, of course, also provided a tight, warm 'home' for my cock.
Occasionally younger couples would make a trip with me. Such was the case on one trip when a newly married couple joined the boat in Seattle for a trip up the Inside Passage, a famous route followed by most US fishing boats going through Canada to Alaska and back.
Janine was 23 y/o. She was maybe 4'11', about 90#, very pert and cute with a smile that would raise the dead. She was an avid hiker, runner, and SCUBA diver, and was in splendid shape. Her husband, Gene, had been on the swimming team at his university. Like his wife he had blonde hair and a dazzling smile. He was close to 6' and very buff.
As soon as they boarded the boat I knew two things: I wanted both of them, and I was sure it would happen. They were open, fun-loving, very sensual, and enjoyed the flirting I greeted them with.
On the third day of the trip we stopped and the passengers went ashore to hike and have a lunch my crew gave them. That was the perfect opportunity for me: I made it clear to crew and passengers alike that in keeping with Coast Guard regulations I had the right to inspect rooms and private luggage to make sure d**gs and weapons hadn't been carried on board. I knew everybody would be gone for at least two hours, so I immediately headed for Janine's and Gene's room. The early search through drawers was about what I expected: bikini panties, g-strings, not a lot of bras (she had very small breasts), tight pants, short skirts. But went I started through his belongings I had a surprise: he also had panties...a dildo...makeup, a wig...and leather leashes and handcuffs.
I got so hard I couldn't help myself: I took a pair of her used panties and stroked until I filled the crotch with a load of cum.
A day later we ran into some bad weather and I let everybody know that would we anchor in a protected cove until the weather passed. I also let Janine know that if she or she and Gene were up late they could feel free to come to the wheel house. I would be on anchor watch late in the evening, and they could join me for some wine and get to know each other better. I don't drink, but didn't feel the need to say so.
She came up to the wheel house by herself around midnight. Fifteen minutes later I had her sitting in the Captain's chair, legs over the arms of the chair, as I licked and sucked on her hairless pussy. After she came...she was a squirter, which really turns me on...I asked if she and her husband ever played together with others. She said they loved group sex, and had already talked about trying to seduce me. I laughed and told her I planned on seducing both of them as soon as I saw them. She asked what I liked. I knew what he had in his drawers, so I told her I was bi, loved a man dressed as a girl, etc. She told me to wait for them. About 30 minutes later they knocked on the wheel house door, and when I opened it there Gene was, wearing a tight short skirt, dark mesh nylons, a blonde wig, and very sexily made up, almost like the makeup had been applied by a professional. And around his neck was a leather collar, with a leash attached that allowed Janine to control 'her.' My cock was very hard, and she caressed it through my pants. He clearly liked seeing her play with me....and when she unzipped my pants and freed it, he licked his lips and asked to taste it. At first she said no, but then she pulled on the leash until 'she' was on 'her' knees in front of me. Then came the crowing touch: Janine pulled a set of handcuffs from her purse, and handcuffed Gene's hands behind 'her' back. Then Janine took hold of my hard cock, and told him to kiss my cockhead, and run 'her' tongue over it. Janine slapped his faced with my cock, and finally had me take my pants and shorts off so Gene could suck on my balls. Janine got back into the Captain's chair, and with her legs spread and her fingers in her cunt she told me to hold his head tight and fuck his mouth like it was a cunt. It was as good as any pussy that could be imagined, and when I finally came, so did Gene, filling 'her' panties with a huge load. After a few minutes to catch my breath, Janine had Gene guide me into her pussy and play with my balls and ass as I fucked her. She was so small and petite and young looking with her tight hairless pussy tight around the shaft of my prick my fantasies ran wild and as another load of cum built up the fantasies focused on incredible erotic ideas that are best not said here (for legal reasons!). Gene had been fingering my ass as I fucked Janine, and since I am a top I really didn't pay attention to what was happening as I was losing control....until I moaned and started pounding her pussy so hard and as I started cumming in her I realized that he had just driven his cock into my ass. His cock wasn't real big but the idea that he was dressed as a girl but was fucking me as I fucked his wife made me lose control as I had never done before.
It turns out that they had been boyfriend/girlfriend since they were about 15, and he had been dressing as a girl since he was much younger. They came from wealthy families and were able to play all around the world. We had a delightful trip together. He never fucked me again because he would dress and be 'my girl' and I got to fuck him almost anytime it was safe. She, of course, also provided a tight, warm 'home' for my cock.
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