Wendi the Winch Wench

by Tony Tiger

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Mult, Sharing, Swinging, .

Desc: Sex Story: A sailor gal's summer crewing adventure.

NOTE: See the story “Lusty Lori” for more background on some of the characters. This can stand alone but is a sequel to the above.

There was an itinerant sailor wench, the kind that goes from boat to boat as crew as their way of life, who had been sent my way. Wendi was a tall lean blonde in her late twenties. Small tits, big smile, and talented crotch. She was good at sailing and screwing so stayed with me for six months over the winter. She took good care of the boat and my cock so I took care of her material needs. We spent a lot of time together holed up in the winter weather and did a lot more together than the good fucking she was quite capable of. Lots of practice pays off for many things.

In the spring she had an opportunity for a paid crew position on a charter boat in the north Atlantic. That was much better financially than the trade-for-pussy most of her living situations had been for the last five years. She kissed and fucked me goodbye but kept in touch by email every chance she had. Sometimes she wrote several and sent them when she could connect in a port. On her little tablet she didn’t get verbose but they did tell her story.

I missed her a lot but had some intimate friends at the marina that kept me from being lonely. BTW, I’m a live-aboard and the above-mentioned friends are female. But they weren’t like having Wendi in my bed every night.

Her summer can be described by the emails she sporadically sent in kind of a journaling style. Many were more mundane so I have selected the ones you might find more interesting. Wendi’s writing is shown as {}:

The day after she left - {Settled into this 54-foot Morgan center cockpit. My berth is a split V in the bow. Cozy but room for two if intimate. Captain is your age but doesn’t talk as much as you do. Other crew not here yet.}

Two days later - {Other crew here. Luke just turned eighteen and has athletic build. Cute but shy. First charter begins in two days. Will go out later today to learn how she sails.}

{I’m a much better sailor than Luke but he’s really strong so will give him those jobs. Went shopping for provisions. Tired tonight.}

{I’m missing you in my bed. Asked Captain if fringe benefits were available. He got the idea and his cock is a lot like yours. Helped my hornies bit he’s not you. When I went back to my berth Luke gave me a funny look. You know how sound travels in a boat. Don’t know about him yet.}

{Our first passengers came aboard. We have two cabins. Two older married couples. First timers. We motored out and the water was calm. One wife got seasick in the cockpit. I made Luke clean up. Next day with meds she was better. No sex for anybody last night I think.}

{In a quiet anchorage tonight. Odd couples. One had heavy guy and skinny wife. Other couple the opposite. Wives took tops off. Luke didn’t even ogle. I took mine off and he did. :-) }

{Got up to pee and saw skinny wife coming out of the skinny man’s cabin to pee also. She smiled at me and I smelled sex. Crawled in with Captain and got laid. Miss you. Love.}

My note: She’d NEVER used the “L” word before in any context.

{Luke getting more comfortable with me. Saw the little ring you gave me. Asked if I was married. Told him about you. He never had a real girlfriend. Got courage to ask me a question that was driving him nuts. Had I “slept” with the Captain? Told him the ‘F’ word wouldn’t offend me and the answer was yes because I had needs. Did you mind? I said you were realistic like me. I think he wants to fuck me but doesn’t know how to ask.}

{Overnight transit last night All sleeping but me and Luke. BTW, guests like being nude and they are swapping. Luke was at wheel and I go topless as much as can. Teased him with my tits and he got boner. Pulled down his shorts and got a mouthful of cum. A lot saved up I guess. He was grateful. Love.}

My note: I’ve been pretty neutral but supportive in my responses. Didn’t use L word but am thinking on it. Only been in love once and she broke my heart.

{That charter done. A few days layover. Capt had to leave to do business. Took Luke to main cabin and screwed his socks off. Not much skill but lots of energy and quick refill. Lots messier than you or Capt though. Love and miss you.}

{It’s been a few days since I wrote. Luke a horny toad! Would fuck me continuously I think so have to set limits. Twice a day since he started. Captain horny when he got back and figured out Luke had been there too. No problem. New guests tonight. Two younger and unmarried couples. Love}

{Lori and Patti said they are keeping your horns clipped. I’m doing OK but all cocks are not created equal. I miss yours. These guests are about my age and want to be fully nude. Captain says crew can decide for themselves. Luke is shy because he sprouts boners so easily in spite of my draining. Kind of funny. More later.}

{We are on adult cruise now. Guest were not couples but horny singles. Gals cute and stacked, guys well equipped too. Fucking everywhere. Gals got Luke and Captain when guys wore out. I joined in to clean pussies. They eat well too. Had beach orgy around campfire. You’d love it. Wish you were here.}

A week later - {Last bunch wore crew out. This one is four gay guys. Not any fun watching. Not interested in me. Education for Luke though. Glad good sailing weather}

A week later - {Family on board with two teenagers. Kids sharing a cabin. Heard them screwing I think. Girl is hot for Luke and boy for me. Kind of young but last night I had late watch and he came to cockpit with me. Said Luke was with sister. Parents are OK with it. Cool at night so I put blanket around us and jacked him off. Kinda small. Sis will love Luke.}

Two days later - {Sis getting all of Luke. Doing bro too. Capt doing me alone. Weather kind of chilly}

My note: She’d stopped using the L word, probably since I didn’t respond in kind. I missed it and guess I’d better sound more affectionate.


A week later - {We will be without wifi for a quite a while. Am keeping journal on my tablet. Hope my adventures rile your cock up. Missing you too. Love}


Six weeks later - {Hi again. Days getting shorter and cooler. Not much nudity on deck but often in cabin. Mostly older couples. We heard that the honeymoon couple that chartered a month ago and swapped with the best man and woman have split up. Luke is getting pretty manly for his age. Looking forward to being home with you}

My note: She considers my boat “home”. Good!


She sure looked damn good coming through the airport exit with her duffel bag. We squeezed each other for a long time. She was crying.

Grabbing her bag with one hand and her hand with my other one we stopped to get a drink at the bar. She would hardly let go of my hands to pick up her beer. “I’ve got a surprise for you, my dear Wendi. Since it’s two hours back to my boat and you’ve had enough of cramped accommodations, I’ve sprung for a room here at the airport hotel.”

I couldn’t get any further. She started crying again. People looked to see if she was OK but the smile should reassure them. We left the beer and walked fast.

Dinner was room service and the delivery boy got a big hug from a naked tanned-all-over, and well-fucked woman. She put his tip in his underpants and got a grab of hose too, giggling. In spite of staying in shape with two talented women, I was soon worn out.

Fondling my floppy disk, I mean “dick”, she looked at me with a devious expression, “I’ve got a serious question for you. Luke was at loose ends after his first job. I offered he could stay with us for a while. Is that OK?”

I nodded, a bit uncertain. She brightened up and continued, “His flight is getting in right now. I’d like to text him our room number. When you get hard you can take charge of my pussy again but in the meantime he can keep it occupied with meaningful activity.” She paused with a questioning look.

What a rascal! She knew she could convince me. I did love her and knew she’d keep it good for all of us.

“Sounds like a plan. He might have to wait for his turn though. Feels like my wicked wench has revived my willy with her wanton ways.”

She got little sleep with NO complaints!


It’s winter. Luke is still with us. We moved a lot further south to warmer weather. Fun to explore the coastal waterway getting there. I got my six-pack Captain’s license so we take dinner/sunset/overnight and up to week-long cruises.

Wendi had a marketing idea based on her summer job and we are promoting “intimate” charter experiences for one couple at a time. Only one guest cabin. Nudity and sex in a romantic setting is the attraction. We know the secluded anchorages or ones where other cruises like ours go. She screens carefully so we do the adult ones about every other week or so. Luke discovered he is bi also and sucks a mean cock. I got snipped too so we have a variety of offerings for adventurous couples.

Those that are comfortable with on-board nudity are the most fun. Wendi likes to demonstrate to the woman how to pee off the rail (that means over the side). The man gets a hands-on instruction how to avoid pissing on the boat. This has instigated watersports with a few interested couples. We enjoy it a lot. It’s a way to get more intimate with another couple if they aren’t into full swapping.

I’ve got to tell you about a recent week-long charter that Wendi arranged. A couple were flying in from Europe. That was new for us. I met them at the airport. Lucie was twenty with a pixie-like face and a substantial bosom. Her male companion had to be more than twice her age. He was introduced as Erik, her manager/lover. They were on their way to a film shoot and wanted to vacation a bit. She looked familiar but I couldn’t place her.

When we got to the boat and as she changed clothes right in front of me in the main cabin, it struck me. I had salivated over her incredible tits in porn videos as Busty Buffy. I had to sit down. She grinned and said in her delightful Czech accent, “So you know who I am now?” I nodded. She put those beauties in my face and I took turns sucking on them.

Wendi was captivated too and asked, “May I?” so she got a few minutes too. Just then Luke returned with the supplies he had been sent to get. He almost dropped them on the cabin floor. Lucie waved him over and he glommed on to a nipple with his mouth and filled two hands with the rest of that mammary. They were THAT big. He later told us that he fell in love right then.

Lucie/Buffy explained that she liked to have sexual adventures that weren’t being filmed. Studio sex was work and not as satisfying as it looked. She’d be fucking for dollars next week but for now she wanted fun.

She would get it, working on her all-over tan and playing with golden showers in addition to some very imaginative fucking as we found beautiful places to go and be on the water.

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Story tagged with:
Ma/Fa / Mult / Sharing / Swinging /