Caught in the act on the charter boat
- 4 years ago
- 24
- 0
Sex Onb My Charter Boat free porn video
I have written about some of my experiences on my charter boat, experiences that were mainly about a tranny who worked on the boat for me, as well as a young couple who I "played" with while they were on board. But most of my stories from the boat involve passengers 50 y/o or older.
Background: Since the early 80's I have owned 4 charter boats that operated in Alaska. Since 1988 I owned/operated a 100' boat that was a very high-end...and expensive...charter operation. I seldom had more than 12 passengers, we explored the east coast of the State for 12-15 days, and my target audience had money.
Occasionally I would have passengers in their 20's, but the 50+ crowd I catered to had money, and they tended to be adventurous. Any time we were anchored in some isolated bay almost everybody would head to the beach and go hiking, scuba diving, bird watching, etc.
Almost every trip in each season there was someone who wanted to 'bed' down the Captain, and I found that even if I wasn't interested in them, there was always a great tip for me at the end of the trip.
I had women who needed fucking and they didn't want their husband know. As often as not the husbands would either watch me with their wife, and occasionally I would spend the evening with the husband. I had a woman on board, Barbara, who was a lesbian and she took advantage of opportunities with women on board who liked pussy. She also was tipped well, and after one trip where she taught a 65 y/o woman the joys of female-female sex, she was handed $5,000 in cash as a thank you. As I said, my passengers were financially well off.
On one trip I had a couple who was in their early 70's. On the first day of every cruise I would have dinner with all of the passengers. During the dinner I knew who I would 'score' with, and I could tell that this couple had sex high on their agenda. At the end of the dinner I used a line that worked very well over the years: "I will be on anchor watch tonight from midnight until 2 a.m. Feel free to join me. I am sure we will have an interesting time." I knew they wanted sexual adventure, and they knew that I knew that.
Both of them were in excellent shape, slim, regal in bearing, and warm and friendly while also being quiet and reserved. When they knocked on the wheel house door I let them in, and was very taken by both of them. She was wearing a short, tight skirt and white nylons. Her breasts weren't huge, but they were full and showed no sag. They did show, however, hard perky nipples unencumbered by a bra. When I openly stared at them her husband asked if I found her exciting looking. He was clearly hard already, and I laughed and said that the stirring in my loins was all the answer I needed to make. And I said I was glad to see he was also excited.
He told me he was excited by imagining what i would do with and to her. She hadn't said anything yet, but I sensed that she liked being submissive, and I suspected that some mild pain might be something she enjoyed. I reached over, and through her blouse I took hold of her nipple and squeezed it, twisted it.....then I kissed her as I continued the nipple play. I started biting her lip, then nibbled along her neck and took her ear lobe between my teeth. Although she winced, she also started breathing harder as she reached down and started massaging my cock through my pants.
I looked at her husband and he winked and gave me the thumbs up. I told him he should pull his monster from his pants and stroke it as he watched. He said "thank you," and I knew that he also had a submissive streak to his personality.
I had a full length mirror on the wall and I made her face it, and from behind I pulled her little skirt up and saw she was wearing nylons, a garter belt, and no panties. Her cunt was shaved and although she was 70, her pussy looked tight and hardly used. "Spread your legs," I told her, "and then spread your pussy lips apart." She hesitated so I slapped her ass real hard. She reached down and spread her womanhood open. Her face was red from embarrassment, which excited me. She started to rub her clit, and I made her quit. "You only do what I tell you to do," I told her.
I told her husband to stand by us and hold her skirt up so her ass and pussy stayed exposed. He held her skirt up, and I slipped a finger into his mouth and told him to get it wet. and then I reached down, spread her ass cheeks, and worked my finger into her ass. He seemed in a trance as I finger fucked her ass....and I gave her permission to masterbate at the same time. As I loosened her asshole he pulled his cock out and stroked it and kept quietly telling me to use her anyway I wanted.
That was going to happen with or without his permission, but I knew it was another step towards both of them being under my control for the entire trip.
Her breathing was rapid and when I reached down to control her hand as she played with pussy I was surprised by how wet she was. She was a squirter, and as she edged closer to orgasm her upper thighs were wet and and she was slipping into her own world of lust. I pushed on her back and she bent over....and I spread her ass cheeks so her asshole was in full view. I told him to take my cock and guide it into her ass. He smiled and yes, he wanted to do that.....but before he did he quickly dropped to his knees, took me in his mouth, and sucked on me. I was content with letting him swallow my load, but he was just getting me lubed with his saliva so I would slip easier into her ass. He sucked on it then spit on the head and then guided me in....she was very tight but she was wanting my cock in her. I started pounding her brown hole as she finger fucked her pussy. In a couple of minutes he moved closer to me.....and came all over my cock as it slid in and out of her tight tunnel. "That is how I want your cock lubed," he gasped.
I could tell she was on the edge, but not quite able to cum.....but I reached around and as I pounded her I took each nipple between my fingers and squeezed and twisted them, and I knew she was feeling the sharp pain of me abusing her breasts, and I found out when her knees started to buckle and she let out a loud, high pitched moan and she was overwhelmed by an intense body wracking orgasm.
I also came, and when I pulled out she just couldn't get the energy to do anything but lay on the floor, but he was all over me, licking my cock and balls and ass, and he continued until he had me hard again. This time I took her pussy and we had a long, slow fuck, as he licked my cock as it slid in and out of her pussy.
They were on board for 12 days and hardly ever went ashore with the other passengers. We had a great deal of intense sex, both explored fantasies, and she finally even had sex with a woman, Barbara, my lezzie deckhand.
That winter they paid my way to Florida to stay with them for a week in their home, which was worth several million dollars.
The next time they wanted to take a trip on my boat I didn't charge them a penny. Giving them a free trip was well worth it since both put much energy into making sure my cock always had a hole....mouth, pussy, mouth....for my cock.
Background: Since the early 80's I have owned 4 charter boats that operated in Alaska. Since 1988 I owned/operated a 100' boat that was a very high-end...and expensive...charter operation. I seldom had more than 12 passengers, we explored the east coast of the State for 12-15 days, and my target audience had money.
Occasionally I would have passengers in their 20's, but the 50+ crowd I catered to had money, and they tended to be adventurous. Any time we were anchored in some isolated bay almost everybody would head to the beach and go hiking, scuba diving, bird watching, etc.
Almost every trip in each season there was someone who wanted to 'bed' down the Captain, and I found that even if I wasn't interested in them, there was always a great tip for me at the end of the trip.
I had women who needed fucking and they didn't want their husband know. As often as not the husbands would either watch me with their wife, and occasionally I would spend the evening with the husband. I had a woman on board, Barbara, who was a lesbian and she took advantage of opportunities with women on board who liked pussy. She also was tipped well, and after one trip where she taught a 65 y/o woman the joys of female-female sex, she was handed $5,000 in cash as a thank you. As I said, my passengers were financially well off.
On one trip I had a couple who was in their early 70's. On the first day of every cruise I would have dinner with all of the passengers. During the dinner I knew who I would 'score' with, and I could tell that this couple had sex high on their agenda. At the end of the dinner I used a line that worked very well over the years: "I will be on anchor watch tonight from midnight until 2 a.m. Feel free to join me. I am sure we will have an interesting time." I knew they wanted sexual adventure, and they knew that I knew that.
Both of them were in excellent shape, slim, regal in bearing, and warm and friendly while also being quiet and reserved. When they knocked on the wheel house door I let them in, and was very taken by both of them. She was wearing a short, tight skirt and white nylons. Her breasts weren't huge, but they were full and showed no sag. They did show, however, hard perky nipples unencumbered by a bra. When I openly stared at them her husband asked if I found her exciting looking. He was clearly hard already, and I laughed and said that the stirring in my loins was all the answer I needed to make. And I said I was glad to see he was also excited.
He told me he was excited by imagining what i would do with and to her. She hadn't said anything yet, but I sensed that she liked being submissive, and I suspected that some mild pain might be something she enjoyed. I reached over, and through her blouse I took hold of her nipple and squeezed it, twisted it.....then I kissed her as I continued the nipple play. I started biting her lip, then nibbled along her neck and took her ear lobe between my teeth. Although she winced, she also started breathing harder as she reached down and started massaging my cock through my pants.
I looked at her husband and he winked and gave me the thumbs up. I told him he should pull his monster from his pants and stroke it as he watched. He said "thank you," and I knew that he also had a submissive streak to his personality.
I had a full length mirror on the wall and I made her face it, and from behind I pulled her little skirt up and saw she was wearing nylons, a garter belt, and no panties. Her cunt was shaved and although she was 70, her pussy looked tight and hardly used. "Spread your legs," I told her, "and then spread your pussy lips apart." She hesitated so I slapped her ass real hard. She reached down and spread her womanhood open. Her face was red from embarrassment, which excited me. She started to rub her clit, and I made her quit. "You only do what I tell you to do," I told her.
I told her husband to stand by us and hold her skirt up so her ass and pussy stayed exposed. He held her skirt up, and I slipped a finger into his mouth and told him to get it wet. and then I reached down, spread her ass cheeks, and worked my finger into her ass. He seemed in a trance as I finger fucked her ass....and I gave her permission to masterbate at the same time. As I loosened her asshole he pulled his cock out and stroked it and kept quietly telling me to use her anyway I wanted.
That was going to happen with or without his permission, but I knew it was another step towards both of them being under my control for the entire trip.
Her breathing was rapid and when I reached down to control her hand as she played with pussy I was surprised by how wet she was. She was a squirter, and as she edged closer to orgasm her upper thighs were wet and and she was slipping into her own world of lust. I pushed on her back and she bent over....and I spread her ass cheeks so her asshole was in full view. I told him to take my cock and guide it into her ass. He smiled and yes, he wanted to do that.....but before he did he quickly dropped to his knees, took me in his mouth, and sucked on me. I was content with letting him swallow my load, but he was just getting me lubed with his saliva so I would slip easier into her ass. He sucked on it then spit on the head and then guided me in....she was very tight but she was wanting my cock in her. I started pounding her brown hole as she finger fucked her pussy. In a couple of minutes he moved closer to me.....and came all over my cock as it slid in and out of her tight tunnel. "That is how I want your cock lubed," he gasped.
I could tell she was on the edge, but not quite able to cum.....but I reached around and as I pounded her I took each nipple between my fingers and squeezed and twisted them, and I knew she was feeling the sharp pain of me abusing her breasts, and I found out when her knees started to buckle and she let out a loud, high pitched moan and she was overwhelmed by an intense body wracking orgasm.
I also came, and when I pulled out she just couldn't get the energy to do anything but lay on the floor, but he was all over me, licking my cock and balls and ass, and he continued until he had me hard again. This time I took her pussy and we had a long, slow fuck, as he licked my cock as it slid in and out of her pussy.
They were on board for 12 days and hardly ever went ashore with the other passengers. We had a great deal of intense sex, both explored fantasies, and she finally even had sex with a woman, Barbara, my lezzie deckhand.
That winter they paid my way to Florida to stay with them for a week in their home, which was worth several million dollars.
The next time they wanted to take a trip on my boat I didn't charge them a penny. Giving them a free trip was well worth it since both put much energy into making sure my cock always had a hole....mouth, pussy, mouth....for my cock.
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