Skipper and the Cabin Gurl

This story takes place on the west coast in the 1990s. It involves several sexual themes including bisexual, homosexual, crossdressing, transvestism, oral and anal sex. All involved are well over the age of 18. While some of this story is based on true life, some are fantasies brought to life. I hope you enjoy the ride!

Stan and Richard the early years:

The Skipper wasn't always a skipper or even owned a boat for that matter. He and Richard started working for the same company in a small interior town several hundred miles from the coast. Stan, (the Skipper) & Richard (later to become Lanna), both enjoyed the outdoors, and shared camping, fishing and hunting trips which never involved any sexual contact at all 'cept for the usual, manly, conversations about women and sex around a campfire. And that, always involved a fair bit of alcohol.

Stan was a bachelor in his early 30's. A short man of midsize athletic build, a bit of a beer belly but not fat by any means. He was well educated, fair skinned with thinning hair.

Richard was about the same age as Stan, but much thinner and very athletic. Richard enjoyed beer as much as any guy his age but was active enough to never really gain a lot of weight or a beer belly. He also, was well educated. However, Richard was married for a time, but for a number of reasons had split up with his wife. The split up was of mutual consent and without any real hard feelings. The novelty of what they had between them, had long worn off, and long periods without any action in the bedroom had bothered Richard and he just really wanted to find someone that shared his interests for many things, including sex.

However, numerous attempts at dating after the split usually ended up with Richard gaining a very good friend who happened to be a girl, rather than a "girlfriend" per se. As a result, Richard spent a lot of time by himself, during which he redeveloped a keen interest he had for his own femininity. But we'll get to that a lil' later.

After about 4 years, of them both working out of the same office, Stan, announced that he planned to apply for a transfer and move to the coast. He always enjoyed coastal living and given that the transfer was to an isolated location, there likely wouldn't be much competition for the job. While Richard was disappointed, to lose a hunting and fishing partner, he did like ocean fishing and suggested that if Stan bought a boat, he would love to come out for a visit and fish salmon with him.

The island that Stan transferred to was very remote. So remote that basic necessities such as fresh produce, milk and eggs were often available only once a month and where women were not only very few and far between, but most all of the few that did live on the island were either married, way too young or way too old for his interest. And, Stan never had a strong commitment to dating anyways.

Richard hadn't heard from Stan at all for quite a while after he moved to the island.

But after a couple years of living in considerable isolation, Stan called Richard early on a Tuesday morning around 2 a.m. He was very drunk...and more than a little marble mouthed, as he babbled on about how much he missed Richard's company and that he treasured the time they had together as well as the many successful fishing and hunting expeditions they had.

More than a little annoyed for the rude awakening so early on a workday and still half asleep Richard asked. "Hey Stan, did you a buy a boat yet?"

To which Stan replied "no...I haven't even started looking for one, actually".

In order to cut the conversation short and get back to sleep, Richard replied, "well Stan, its 2 in the morning and I gotta work in a few hours, so, don't bother calling back till you buy a boat eh" and with that, as Richard was hanging up the phone, he heard Stan reply..."ok!"

Which was very much like Stan and the relationship they had. He genuinely valued Richard's opinion on many things. There never was any arguing or heated discussions about anything. They both just got along very well with each other.

Richard went about his work over the next couple weeks and figured that he likely wouldn't ever hear from Stan again, till the next time he was really drunk at all hours of the morning and needed someone to talk to but, ...later on a Friday he gets another call from Stan, this time at 6 o'clock in the evening, and surprisingly, Stan was sober.

"Hello Richard? Hi, hey its Stan, sorry for calling you so late there, a lil while back. I had a few too many and was feeling lonely, ya know...just needed to talk to ya'...'cause it's been a while."

"Oh, hey, good to talk to ya Stan...you sound a lot more sober than our last chat"! laughing.... "so how ya' doin? Did you buy a boat"? Richard was getting right to the point.

"Well, as a matter of fact, I did". Stan replied. "I bought the exact boat you recommended, aluminum weld 20' with a 220 Yamaha on it. "

"Holly shit"!! "replied Richard... "Really?"

"You bet" Stan says..."and well I'm just getting it ready to do a first cruise and see how she works. She's only about 4 years old...and seems to have everything we need, down riggers, and some gear, Lowrance GPS map system, CB radio, a few crab traps...it was pricey but I figure by the time I leave here I'll get my money back out of her."

"That's fantastic!" replied Richard... "so, when can I come out?"

"Well for Springs, and Coho...I'd say mid to late July would be best."

Stan told Richard he needn't bring much but his clothes, a few big coolers for fish, and a fishing license.

At that Richard could hardly contain his excitement. "That's awesome, I can't wait" I'll just walk on to the ferry if you could meet me on the other side?"

"Oh, for sure, Stan replied, "that's the best way to do it. The ferry terminal is close. Really close, actually, email me your arrival date and time and I'll be there to pick you up."

So, the stage was set for a fishing trip in late July of that summer.

Richards's Feminine Side:

As mentioned earlier, over the past couple years since Stan had left for his transfer to the island, Richard had gone through a separation with his wife. It was mutual, and though they both struggled with the split at first, they remained as friends.

After dating didn't help him find a mate, Richard revisited a longstanding interest he had in developing his womanliness. Richard always had quite a few feminine traits. He was always much more sensitive than most guys. It didn't take much for him to well up watching a movie, or to hear sad news of someone passing. He didn't like a lot of crazy redneck pastimes, like loud cars or motorcycles nor developed an interest in contact sports, like football.

But he did like gardening, healthy cooking, music, the arts and had a thing for fashion and was quite particular 'bout how he dressed. When was married he would get very excited during the few occasions when he was able to talk his wife into wearing lingerie in the bedroom. Which she would go along with merely to keep him happy.

Now with the divorce finalized, Richard was free to explore and develop his feminine interests with a lot more time and privacy to do so.

While Richard always had been fairly athletic, he now spent time researching how he could take his physique to another stage. He also had the time, energy and interest to develop and work on an exercise program that included, in addition to long distance running, sit ups and leg raises to flatten and tone the abs, but also yoga and Pilates exercises to help develop that hourglass figure, with a very thin waist and very little body fat.

With all the time and privacy, he had, and a great deal of determination, he worked on his exercise program daily and with vigour. If certain programs or exercises weren't getting the results he was looking for he would research it and change it up. He enjoyed posing in front of mirrors, and looking at how his shape was quickly manifesting to that of a young woman. He often worked out in tights and sometimes even complimented the look with a sports bra, which not only provided a clear view of his nice, slim flat abs between his rib cage, belly button and waistline but also gave a him a deeper confidence in his femininity. He also experimented with various diets, Phyto estrogenic herbs and massage exercises to stay slim and help develop his breasts. Which surprisingly, worked to a modest degree. He managed to grow his breasts to a B cup and his nipples became very sensitive to touch.

As his femininity grew, so did his interest in fashion, and shopping for women's clothes. He avoided embarrassments of instore encounters by shopping online and would spend hours doing so. His early explorations with lacey bras and panties soon grew to corsets, stockings, & garters. Richard would get so excited whenever his online shopping would arrive in the mail and he had the chance to dress up and model new clothes and styles. He often would find himself shaking like a schoolgirl just opening the packages, rolling nylon stockings on to his feet, smoothing them carefully up his legs and attaching the matching garters.

Richard was blond and blue eyed and so what little chest and leg hair he had on his body was barely visible, but he soon shaved them off anyways, thinking, "no problem, it'll grow back. No one will notice". Fortunately, or unfortunately for hm, it never did grow back. Even the little tufts of hair in his armpits, once removed simply by shaving, never grew back.

The feel of sheer nylon stockings on his hairless legs as he practiced walking in heels, the garters tugging them tight, the feel of his erect nipples rubbing against the satin of a sheer nightie or satin' n 'lace bra sent electric pulses through his body. He experienced a very excited and yet, nervous, arousal. His heart beating loudly and his cock coming to full attention without any other stimulation. It was a sexual high he'd never achieved before. He absolutely loved it!!

The more his figure developed the more his interest in women's fashion and addiction for sexy lingerie grew. His female wardrobe now included sheer mesh skirts, leather and pleated swing dresses, and even a sharp looking women's business suit jacket, matching skirt, and heels. The hot secretary look with a black lacey bra beneath, a see through white collared shirt, complete with a pair of women's glasses? So sexy!! It was then that he decided his female alias would be "Lanna"!

All the while Richard was greatly enjoying his private sessions with his feminine side, he assumed that his body shape and look wasn't noticeable to anyone else. And it probably wasn't, ...to most, thanks to wearing baggy clothes to work and social events, or ...fishing trips. But that was about to change.

Richard's First Trip To the Island:

That summer, about the third week of July, Richard boarded the ferry to take him to the island. The ferry was a large vessel and the trip to the island would take anywhere from 5 to as much as 12 hours, depending on weather and how rough the sea was.

The sailing left on time and was a nice sunny afternoon for a trip across the ocean. No rough seas, no problems. When he got to the island Stan was waiting for him with his pickup and a powerful thirst. They headed to Stan's mobile house trailer where the boat was parked on one side of it. Stan had a flat of beer on ice and the boys cracked a couple while Stan showed off his new boat.

They worked together to load and ready the boat for the next day's trip. While they both had fished the ocean previously, this was the first time they would fish together without a guide or someone who really knew what they were doing.

The next morning, they launched the boat and set out in the fog on their first fishing trip. Partway out to Stan's spot they stopped, baited and dropped a couple crab traps. They would check them on the way back at the end of the day.

They spent a long day out on the ocean in the rain, with not a lot of action on the salmon rods, 'cept for a few rock cod and a couple pink salmon which they weren't interested in, so they headed back early. Checked the crab pots and limited out on very large Dungeness Crab for supper.

Soaked to the bone despite, heavy rain gear, the boys proceeded to drink a lot of beer and discuss ideas to try and get some salmon the next day.

The next day was going to be a blue blazer once the fog burnt off, and sure enough by the time they got out to the salmon grounds the sun came out and was a beautiful morning. A charter boat was fishing the same area and the boys watched them catch quite a few fish while they still weren't even getting a bite.

Richard suggested that the charter boat was trolling much faster than they were, "maybe we need to speed up a little".

"Ahhh, shaking his head, I don't think so. Salmon like their food presented to them slowly", replied Stan however not being one to argue, "but, ok let's give it a try".

"How about we just troll along way behind them but keep up to their pace" suggested Richard as he started removing the layers of rain gear and heavy wool sweaters. While Stan proceeded to speed the boat up.

Completely engaged in catching fish, Richard forgot what he was wearing beneath his raingear. Since his baggy sweatpants from the day before were still wet that morning, he left them hanging in the laundry room and put on a pair of his women's spandex yoga exercise tights. They fit his small frame so well, very comfortable and warm. They particularly hugged his ass very tightly. Wearing them had become second nature to him, so he was completely unaware of just how feminine and sexy they looked.

So, while they trolled along behind the charter boat picking up speed, Stan noticed Richard's beautifully shaped butt and skinny legs and how the spandex tights hugged his body so well. Now, not only had Stan not been with a woman in a couple years, but he also hadn't seen anything like Richard's very feminine butt because there were very few, if any, women on the whole island that had a body like that.

Stan's stare went unnoticed until the charter boat ahead of them began to wave and shout obscenities for them to back off.

"Oh shit, said Stan, I didn't notice we'd crept up so close". Just then Richard's fishing rod bent over and he sprung on to it, fighting to get it out of the rod holder... picking up the slack and giving the rod a tug to set the hook and free it from the downrigger. Out of the water came a 40lb chinook salmon, leaping into the air.

"Woo~hoo"! Richard yelled.

Stan set the motor in neutral as they dropped back from the charter boat. After a 20 minute fight and nearly losing the fish a couple times, he was able to steer their first salmon to the net that Stan lifted into the boat!!

Big cheers and high fives all around and the fish went into the cooler.

Stan turned the boat around and said "huh, guess we gotta troll a lil faster eh? Nice fish Richard!"

Richard reset the lines with fresh herring strips and proceeded to let them back down. Unbeknownst to him, as he bent over the side of the boat to grab the downrigger line and pulley to attach the line, Stan was again fixated on Richard's sexy butt in them tights.

About 20 minutes later another strike this time on Stan's rod and another salmon came to the net. "Good on ya figuring out the speed thing, there cabin boy"

"You betcha, Skipper Stan", Richard smiling broadly, answering back.

Again, the Skipper tended to getting the boat back in motion and in their trolling lane, while Richard tended to Stan's line which required him to bend from the waist over Stan's side of the boat. This time, Richard's butt was just a few inches away from Stan's face.

Stan couldn't help himself any longer and stood up grabbed Richard's waist and dry humped him from behind 4 or 5 times.

Richard pushed Stan back while bent over, and then stood straight up and looked back at the Skipper. "What the fuck?"

"Sorry", Stan replied, backing away, "but man, ... you have a really nice ass!"

Richard was shocked and didn't know what to do or even how he felt about that. He just looked back at the Skipper who grabbed a beer and lit up a smoke.

"Relax, don't worry about it. Have another beer!" Stan said chuckling to himself.

The wind had started to pick up now anyways with the changing tide, so Richard decided it best to put his rain pants back on. The skipper didn't say anything.

They caught a few more fish then headed back.

A very successful day had the boys in a celebratory mood. A feast of salmon on the BBQ, a couple of crab and all the fixins with a nicely chilled bottle of Riesling made for a very nice evening. A couple of drinks of some fine scotch that the skipper brought back from a trip to Scotland, cigars, and lots of laughs and, nothing more said about the dry humping episode on

the boat.

With the long day, and all the alcohol, Richard soon grew tired and headed to bed. Stan stayed up for a while longer and finished another scotch and a few smokes. Then after a long night of drinking, and on his way to his own bed, Stan came into Richard's room and pulled down the bed covers ... Richard half asleep, hardly moved, laying on his side with his ass towards Stan. He had had enough alcohol to not really care at this point.

What are you wearing now?" Stan asked.

"uh, my satin ..thong underwear.. very comfortable for sleeping in." Richard replied sleepily not raising his head off the pillow.

But being too drunk to do anything, anyways...and still a lil shocked, Stan replied with a drunken "Huh. Well ga'night!" and just closed the door and went off to bed.

The next day, both hungover, and needing to supply up, Stan went into town to fill the boat and truck with gas and pick up a few things they needed. Richard decided to stay back and clean up the kitchen and dishes. He decided he might as well do laundry as well, and went into Stan's room to get his dirty laundry and discovered his huge porn collection...which included a dozen or more videos of heterosexual porn, but interestingly, also a few male/male, as well as a few transsexual, and bisexual videos and magazines. Richard nervously looked through the collection making sure to put everything back as it was so Stan wouldn't notice. But he decided to borrow a small European magazine, that carried articles on male to female transformations and stories. Since it was small, he figured it would be easy to conceal in his luggage and the Skipper wouldn't likely notice, given the huge collection he had.

"This will be interesting reading for the long ferry ride back to the mainland he thought."

An hour or so later, Stan returned from town and they spent the day mostly hungover. They took a walk down along the beach to try and shed the hangover fog.

They spent the next few days much the same way, catching more fish, more seafood feasts, and drinking to all hours of the night.

Then it was time for Richard to head back to the mainland and his normal work life with plans to return the next summer.

"Hey it was great having ya here for the inaugural fishing trip...maybe we shoulda smashed some cheap champagne on the bow or something" Stan says as he's shaking Richard's hand at the ferry terminal.

"Nah, Richard replied, "that would be a waste of cheap champagne!! Thanks so much for everything!! It was a blast...and I'm happy to be going home with enough fish to last me til next year probably."

"Right on!!" said Stan, let me know when you wanna come out next year. "

Stan Meets Lanna

The following year in late July, Richard returned to the island for a couple weeks of fishing. This time Stan invited Richard to stay as long as he liked. On arrival, after a few drinks they enjoyed a dinner of fresh crab and coastal venison steaks complete with a nice white sauvignon. Stan then offered Richard a bathrobe and a VHS porn tape.