Skipper and the Cabin Gurl Ch. 04

The Skipper Gets to Pull Lanna's Plug

This story series takes place on the west coast in the 1990s. It involves several sexual themes including bisexual, homosexual, cross dressing and transvestism, oral and anal sex and in some cases, just regular steamy heterosexual 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. So, grab your jewels, a nice drink and I hope you enjoy the ride!

Dear Readers: In this chapter Lanna bathes in her femininity, enjoying the experience of pampering, cross dressing, and fully engulfing what it would be like to be a sexy woman. All in preparation for the Skipper's return. I realize this might not be everyone's cup of tea, but for us sissy Cd's it is as equally arousing as the act itself. I hope you find the buildup to the sweet sexy climax well worth the read. 💋 Lanna

Exercise is the best medicine

It was still early morning on the island when Lanna headed back to Stan's place after coffee in bed with Holley. She was leaving in a couple days to go back to her own place on the mainland and then back to work after her 2-week fishing vacation with Stan, the Skipper. But she just couldn't shake the deep feelings of guilt for having had so much sex over the past couple days with Holley, while Stan was up island working on a new project.

Lanna had known Stan for quite a few years and he'd always been very good to her, well actually, very good to him, as Richard. But Stan absolutely loved Lanna, ... and Richard for that matter, and he always was more than attentive and considerate to either.

She too had deep feelings for Stan and was struggling with deciding why she felt guilty. Would Stan have had these same feelings if their roles were reversed? It's not like they were a couple, or married, or anything like that. However, she thought about how, over the past couple days, the extent of the sex-capades, the sexual teasing, followed by prolonged, intense fucking she had had with Holley was all way more sex than the couple times with Stan, when she finally came out as Lanna. She just felt that she owed Stan much more than that.

Once back at Stan's place she decided what she really needed right now was exercise. It had been days since she had a chance to go through, what was, her daily exercise and yoga routine, and, she could really use a good long run to give her time to think about all that transpired.

Lanna changed into her green yoga pants and a sports bra, tied her hair back in a ponytail and spread out a large towel on the living room floor.

Stretching and holding her poses in asana felt really good and went a long way to help clear her mind. The poses and meditation also greatly helped with linking her to her femininity. She continued with her routine for 45 minutes.

Looking outside she could see the morning fog was beginning to lift, and it would likely burn off soon, to a nice day of sunshine. She went to her room and dug through her bag to find a pair of running shorts. She found her nice pair of pale pink/white satin Adidas shorts that just covered her cheeks. She would need something to stash her gear though, so it wouldn't be so obvious in those satin shorts. She found a nice white, spandex thong that had a li'l "tuck" pouch in front. Perfect, she thought! That, along with a halter top that matched her shorts and a bandanna not only looked sexy, but helped her feel good about herself, while still trying to shake the guilt. A little catering to oneself goes a long way.

Since it was still fairly early in the morning, there shouldn't be a lot of people or traffic along the road anyways, she thought.

So, she headed out the door to start running down alongside the road. From the mobile court, the road went down a steep hill toward the ocean and then went, either to the right into town, or left, up-island along the beaches for about 30 or 40 kms before heading into the island interior. Lanna decided to go left and just run her blues away.

Starting at a slow pace, her mind tossed the idea of maybe just coming clean with Stan and tell him what had happened with Holley. Maybe Stan would be thrilled and possibly envious that she had such a great opportunity with Holley. But then it could as easily go the wrong way and she would run the risk of upsetting him, and possibly ending their friendship. She really didn't want that.

Holley seemed to be sensitive to keeping their relationship a secret, and, in just a couple of days Lanna would be back in her own home, and all would likely be forgotten by the time she came back ... which would be at least a year from now. That seemed like the easiest way out.

There was still fog and a heavy mist along the ocean. It seemed a bit haunting where the fog was heavier, and the mist gave the air a damp feeling. The seagulls and shorebirds were cackling loudly, but the fog was too dense to see them, and where you could see, it looked like the tide was going out. There was a gentle breeze that felt good on her legs and backside, though, just a bit cool. "Come on sunshine", she said out loud. She decided to pick up the pace to try and warm up a bit. She could feel her erect nipples against the spandex of her bra. Just then a car sped past from behind, tooting the horn at her. Hmm, best keep well over on the shoulder or better yet, once the tide goes out a bit more, she could run on the beach.

Just then another car slowed as it passed her and a guy stuck his head out the passenger side window... "Hoo~wee baby, you just made my day!" with an added sharp whistle.

Lanna smiled. "Well, that felt good, actually!" Lanna enjoying that she could pass enough to get a catcall! But, best play it safe, gurl. With that, she headed down, off the road and started to run along the beach. Though it was damp and wet in spots, it was incredibly beautiful and "when would she get to do this again?" she thought.

After about 30 minutes along the beach she turned around and continued to run back. Staying on the beach, till the incoming tide forced her back on to the shoulder of the road. The sun was now burning through the fog. It was going to be a beautiful day on the island.

She continued to run with the emerging sun at her back and made her way to Stan's place.

Just as she was walking up the hill, wiping the sweat from her brow, she turned towards Stan's mobile home, and saw Holley come out of her place walking towards her with something over her shoulder.

"Beautiful day for a run, Lanna! Look at you! No wonder you have such a hot body! I really need to start doing that soon. Lanna, would you mind if I came in? Just for a minute or so? asked Holley. "I have this bag of goodies for you. I'll only be a sec dear"?

"Sure" said Lanna. "Come on in. Sorry, I need to get some water, though."

Lanna headed straight for the sink and reached above, on her tippy toes and retrieved a glass out of the cupboard. Holley got to admire her sleek athletic body and a brief look at her tight ass cheeks, peeking out of the pink shorts.

"Sweety," Holley starts, "I'm so sorry to have caused you all this grief and guilt and whatever you're feeling. But It was just the heat of passion in the moment, ya know, I didn't mean to put you through anything.

"I mean, you've really helped me out of a deep dark place. That, I couldn't get out of ...until you came along...and believe me, others tried all kinds of things, ...therapists, ... anti-depressants, ..booze, .. get togethers, ... nothing really worked... but you did something for me that I'll never forget, ...and I really appreciate it."

"Oh? Ah geez, I had no idea 'bout all that" replied Lanna with concern.

"Well, losing Frank was really hard on me! Now, I know you're all on for Stan, and you want to spend the rest of your time here, with him, and that's all good, dearie.... I promise I'll stay clear of you from here on... and, of course your secret is safe with me, .... unless, of course, you've changed your mind...and ya know, you want to hang with me today?"

"Oh Holley, I really enjoyed the past couple days with you, and everything that happened was really great...I mean, believe me, ...I ain't complainin'...but I really need to spend the rest of the time I have left here with Stan.. you can understand that can't ya?" Lanna urged.

"Yes dear, for sure! And he's a very lucky guy to have you! Ahhh, it was grand though, wasn't it? Here, I have this bag of stuff for you... look, I have to tell ya something, and you probably won't like this much, but I had to call my sister and tell her all about you..and, I promise, SHE'S THE ONLY ONE WHO KNOWS, ... I swear!" Holly pleaded in a louder voice.

"She said she could tell I had changed, by the tone of my voice. She knew right away, ... and..well, she's very excited to meet you sometime. She really wanted to thank you for what you've done for me, ... AND, she told me she left this suitcase full of stuff here, because crossing borders as a trans person is not easy, ...its downright awful, actually, ....and she didn't want to make it any worse be carrying this bag of sexy clothes, heels, makeup, and jewelry, ..so she left it at my place, in her room. But she really wants you to have it."

"Really?" Asked Lanna, with a broadening smile. "Wow, that's so kind of her. This day just gets better n' better! Thank you so much for this, and for understanding how I feel about Stan. And, ... a big thank you to Stacey for me when you talk to her again, please."

"I threw in a few sun dresses and things that you tried on yesterday. Most of what seemed to fit you much better than they do me. So, hope you will get some wear and use out of this stuff." Oh, and I'll be sure to let Stacey know how much you appreciated it! I hope you get to meet her sometime." Holley replied. "You's two would get along, sooo well!"

"Ahhh, .... I'm gonna miss you, Sweety! Here, come give us a hug, eh?" and with that, they enjoyed a big hug with their heads on each other's shoulders and a couple of tears running down Lanna's cheek.

"Ok, come dear, I better get going before Stan shows up" said Holley as she broke their embrace and flapped her hands in front of her face to keep her tears from coming too.

Lanna Preps for the Skipper's Return

After Holley left, Lanna immediately took the big pink duffle bag to her room and couldn't wait to see what was in it. The bag was full, and everything was wrapped in individual plastic bags.

"Wow, most of this stuff is brand new" she gasped. There were bras and panties, stockings and garters, quite a few cocktail dresses, a pair of open toed heels that looked like they might just be the right size, a full makeup bag, and a beautiful brunette wig with blond highlights. It looked like it was real hair, not synthetic. Very expensive!

And then down in the bottom, was a bag of sex toys. A large dildo, a set of butt plugs in a variety of sizes, a large container of lube, and, as Lanna started to giggle, a pair of handcuffs. All in the original packaging, unopened.

"Wow! That's a lot of stuff!" Lanna sighed out loud. "There's got to be a small fortune of stuff here. Stan~ley? It's game on! We're gonna have us some fun tonight! Whew Hoo!" she shouted out!

She so needed to get ready for this. Starting with a shower, a good shave and some nice perfume. All the things that would help shed her guilt and highlight her excitement for the Skipper's arrival.

Lanna headed to the shower, ensuring that all her parts were thoroughly cleaned, shaved and freshened up. She got out, towelled off, and decided to try one of the butt plugs. She really needed to do this if she wanted to "go all the way" with the skipper. No matter how much it might hurt, she was determined to be prepared, this time.

The butt plug collection had a simple smooth, tapered pink silicone plug in a very small size, and then a medium sized one that looked like a string of beads. There was a long skinny one made of clear, jelly like substance in the shape of a very small penis. Then there was a cute one of medium size with a long pink squirrel-like tail. She gave them all a quick wash with soap and water and dried them off.

Lanna was excited to try them and hopeful they would help cure her fear of anal sex. She got the bottle of lube and dripped a gob on the top of her ass. She caught it with her fingers as it dripped down her crack and she slipped a finger inside very gently, stroking and making little circles around her entry. Going deeper, and deeper each time. 'That's not so bad' she thought. This seemed to be going better than expected with the lube. She then picked out the small one to start. She rubbed it liberally with lube and bent over, reaching behind, and slid it gently to her butt hole. She slowly slipped it in.

"Ow! Fuck!!!, why is that so painful?" she screamed. "Ok, just relax, Lanna" she attempted to coach herself. She tried to rest a bit and took several deep breaths focussing on trying to relax her sphincter to let it in. She pushed it slowly in and out and tried angling it a little deeper each time. Partway through and despite all the lube, it still didn't feel very nice at all.

She waited for a few minutes, leaving it part way inside her and tried to think of something else, while keeping the slow and gentle in and out motion going. Then all of a sudden, it was in. Her sphincter seemed to relax and accept it. She worked it a bit more with slow, gentle nudges and then when she straightened up, it almost slipped out again. So, she towell dried her crack with the plug all the way in and put on a nice fresh pair of thong panties. The band of the thong helped keep it in. She stood up and walked around a bit. All good. The more she moved around, the more she got used to it, the more the pain went away. While the plug continued to arouse her, for some reason her breasts felt full. It was like they felt larger and more prominent.

"Ok, let's get on with the best part! Some nice, sexy lingerie."

Lanna selected a nice lace, padded bra that give her breasts plenty of lift and would continue to give them that "put out there" feeling. She could feel her nipples rubbing against the material. It made her feel very femme and aroused. As well, her freshly shaved mons and balls were ultra-sensitive to rubbing against the nice fresh satin thong panties, while the butt plug continued to remind her of what to was to come. All triggers that kept her focused on being the naughty, sexy seductress she was planning to be for her skipper.

"Ok and now for some nice "Poeme de Lancome" perfume. Such a beautiful scent that lingers in the room for hours." She recalled from the commercial on TV. This was indeed, "special." There was something about wearing perfume that just, "took it over the top", and made her feel so much more sensitive to her femininity. As she caught sniffs of it, she strutted and swayed her hips around the room like a sexy starlet.

"Ooo! This feels so nice!" Lanna said to herself in her sexiest feminine voice.

In Stacey's 'Pink Bag of Goodies' she found a pair of black mesh, bell bottom, see through pants with ruffles.

"Ooo, very sexy" gasped Lanna. She tried them on immediately. They were a perfect fit and she could feel that her 'clitty' was liking them too. The feeling on her skin as the airy see through pants brushed against her legs was rousingly exquisite. "Mm~mm, I wonder what the rich bitches are doing tonight?", she giggled.

Her cock began to swell, and she could feel it leaking just a bit into her thong. "Down boy, not now!" she smiled and whispered down to her crotch. "Your time is cumming! ...Soon!"

She continued to go through the bag, taking each package out and holding it up to see what it was. She found a nice V neck black satin crop top. It was very dressy, like to go with a business suit. She put it on and looked in the mirror to see that it showed off her flat slightly muscled abs quite nicely, and the v neck drew attention to her petite cleavage. Hmm, but it needed a li'l jewelry for the 'finishing look'. She knew exactly what she needed to complement that.

She dug through her own jewelry and found her favourite dainty gold chain necklace that featured an "L", for Lanna, of course. It shimmered and dangled from the lowest part of the chain while it also helped to draw attention to her petite but elegant, firm breasts. She added a pair of matching gold, dangly earrings and a couple of bracelets on each arm. The finishing touches to her 'Lanna look'.

She walked into the living room and went through the stack of CD's. She found Maria Muldaur's "Naughty, Bawdy, n Blue" album and put it on while she went back to the bathroom to tend to her makeup. Humming and singing a few lines while doing her eyes and foundation. Swaying her hips to the beat and admiring her sexy look and confidence.

She donned the wig cap and then her new long brunette wig that was in Stacey's bag! It had nice bangs that hung over her forehead to the top of her eyebrows and long strands that hung nicely down her back, and just to the underside of her breasts in front. She walked back into the skipper's room to use the full-length mirror to check herself out.

She turned and posed from left to right, .... turning a leg out, ... putting her hands on her waist, and then turning her back to look at her ass in the mirror.

"WOW!!! Amazing! If I do say so my~self!" It was like she was a whole new woman. "I'd fuck that!" she laughed out loud and was all giddy with excitement, not to mention more than a bit aroused.

Her outfit definitely needed heels to go with it, ...but, having a bit of housework to do, she didn't want her feet to get all sore and swollen before the Skipper arrived, so she dug out her black flats and wore them for the time being.

She got busy with cleaning up the kitchen a bit, and making a salad, putting a couple bottles of wine in the fridge to chill, and getting the rest of the supper ready.

"Looks like salmon, rice, veggies n salad is the menu for tonight, if we ever get around to it." Laughing again to herself. Lanna enjoyed cooking, listening to music and walking around in her feminine attire, practising her lady like moves. Even if she was alone, it was quality feminine "Lanna time."

The phone rang, it was the Skipper.

"Hey hello Richard" said the voice on the other end of the line.

"Well hell~lllo, there stranger" answered Lanna, in her sexiest femme voice.

"Ooo, that sounds sexy", the Skipper replied. "Hey, I'm sorry, but I'm running a bit late again today. But I should be home by about 6:30, 7 or so. Hey so sorry for the delays and being longer than I thought...but, I got so much to tell ya. And we need to.."

"Oh, ok, no worries", replied Lanna, "Hey, I've got a couple surprises for you too."

"Really? Well, that sounds won~derful babe" ... ok see ya when I get there, Ok? I shouldn't be too much longer here."

Lanna finished with getting the rest of the supper ready and some cleanup. She still had a few hours left before Stan would arrive. She decided she should have the nice maid outfit that Stan had bought for her, all laid out and ready in her room and then put it on once the skipper got home.

She poured herself a tall glass of wine. It was a nice Riesling, that was just a bit sweet. Just the way she liked it. She sat in the living room sipping her wine and planning her greeting.

"We'll have to take it over the top, Lanna! This will be the last chance for a whole year.", she told herself.

"Hey". She got up and went through the CD's. "I think I left an RLJ CD here last year." She wanted to hear Rickie Lee's 'Last Chance Texaco'. "That song's perfect for how I feel right now."