Skipper and the Cabin Gurl Ch. 02

Skipper and the Cabin Gurl Chapter 2:

Insatiable Holley discovers Lanna

This story is 2^nd in the series "Skipper and the Cabin Gurl" If you haven't read the first chapter you may want to read that one first, so you know who the characters are. But that said, you might get by to start here, if you wish.

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 and in some cases just regular, good ol' fashioned, 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, strap on, grab your jewels and I hope you enjoy the ride!

The Skipper and the Cabin Gurl Bask in the Glow

After Lanna and the Skipper had their first steamy 69 together, Lanna went to the bathroom and cleaned up quickly while the skipper makes a jug of pina coladas in the blender.

They meet again in the living room to sit back and gently ease into and enjoy that after sex glow. This one, was especially satisfying given the couple years of pent up sexual frustration and arousal leading up to the big event.

The Skipper leans his glass towards Lanna's, "here's to yet another successful mission, Lanna!"

Lanna smiling, clinking her glass in unison. Still donning her heels, nylons 'n garters, and black lace bra beneath her white "complimentary" cotton robe. She was smiling broadly, both from the feeling of sexual gratification but also in celebration of her major accomplishment having seduced the skipper and passed as a sexy woman.

"So, Lanna," the Skipper pausing just for a sec, trying to choose his words carefully,

"please tell me why you waited so long to make that happen. You know you had me right from your first trip out. And, hey, I should apologise for accusing you of stealing from my porn collection. I actually left that open and intended for you to find it, hoping that might break the ice." Said the Skipper his eyes pointing toward the floor.

"Well, I thought about all that", replied Lanna, "but wasn't sure how you might react. I didn't want to steer the boat in the wrong direction. And I still have the little book I borrowed, if you need it back. I did get a few pointers in there on male to female transformation." She added, with a shit eating grin.

"All good," Said the Skipper with a big smile on his face, taking in Lanna's sexy appearance, "really fucking good! Actually."

"So, does anyone else know about your crossdressing and being a sissy? uh geez," shaking his head at himself, "sorry again, I don't wanna' use labels that are inappropriate. I just don't know what the proper,...political~ly....correct terminology is, to use here."

"That's ok. That's a commonly misunderstood thing these days, and actually even I'm a little confused on which label applies, but I prefer "CD" or "trans."

"But with regard to, who knows about my crossdressing and sexual orientation? Whatever it is?

Uhm, I think my ex knows. She's never caught me dressed but she mentioned more than a few times about how femme I looked and acted sometimes. And, it was, no doubt, why she wanted a divorce."

There are, or were, a few other, "so called friends", that never contact me or check in on me when they're in town so... they must know something too." Lanna staring off at the walls.

"Well, hey...Fuck them!" says the Skipper. "You don't need them anyhow!!"

"How about work? The company good to ya? Do they give ya the short end when opportunities come up?", he asked sincerely.

"Nah, I have to say the company's been really good. I couldn't say for sure that anyone knows anything there, but, I'm sure it's talked about behind closed doors." Lanna replied with a serious tone. "but no, they appreciate my work and support me on most things."

"Aahh it don't matter" At least,.. here?..For me? I'm really glad you came!" then realizing the double meaning of what he just said and how it applied to the situation, they both burst out laughing.

"But seriously Lanna, you are the hottest gurl I've ever had sex with. And I'm sure there isn't a dame on this whole fucking island that comes close, with that hot looking ass of yours. I'm serious! You've put a lot into your transformation, and it shows!"

With that, they clinked their glasses again and downed the rest of their drink.

"Another?" asks the skipper "and a smoke?"

"Yeah, for sure", replies Lanna.

Lanna makes a quick trip to the bathroom and returns to the living room to find her pina colada and a fresh cigarette in the ash tray waiting for her.

The skipper begins chuckling to himself again and says "I can't believe I just sucked your dick!! It sounds really strange to say it out loud but, it was good, damn it!! I've never done that before. Please, believe me."

Lanna giggling and smiling says... "Yeah, I think we know that, Skip! It was definitely the trigger that let me know that we were all good with it and to relax and enjoy the moment! And, hopefully, there's plenty more where that came from!" laughing and smiling away.

"Ok well, we got some shit to do" says the skipper, "I don't want to get too loaded here and have to drive, so, let's get going. Do you wanna' come to town or stay here and do the cleaning? Or what?"

"Aaa, Lanna says, I'll stay and do the cleanup, I have to clean myself up a little better anyhow" giggling again. "I'll get a supper ready too."

"So, tell me, do you like... being the maid?" asked the skipper, "I mean you do all that cleaning and cooking shit,.. all the time."

"I do, actually. I like being the maid", Lanna laughs. "I could be a real sexy maid if you want me to be. I didn't bring the maid outfit though." Laughing again.

"I bet you could!" grinned the Skipper. And off he went to town.

Lanna went to her room and changed out of her outfit. Since she had housework to do, she wanted to be comfy so went with her nice black satin thong, the light green spandex yoga pants that the skipper liked so much, and a ladies' teal coloured, cropped T shirt, that showed off her slim tummy line, and allowed cool air under it to keep her nipples erect.

Somehow in her mind, once she was out of her lingerie, her femme mannerisms shut off, and she resumed her role as Richard, even though she was still wearing women's clothes.

So, he got busy with cleaning up the kitchen and getting some steak out to thaw, he took inventory of the vegies they had left in the fridge and planned the dinner.

"Hmmm I think we'll need a bottle of red for tonight." Which he happened to have in the porch. A nice full-bodied Merlot that he put in the fridge to chill. Richard liked his red wine, and preferred it chilled just slightly.

He then prepared the rest of the meal so it would be easy to just turn on the burners and heat everything up, and BBQ the steaks when they were ready to eat.

The Skipper returned from town with the boat and truck all gassed up and ready to go for another couple days of fishing. He walks in the trailer with a box all wrapped up, with a bow on it.

"Hey, I got you something while I was in town. Hope you like it. I know I will!" chuckled Stan

"Oh, you didn't? Richard said with a big open smile, "I think I can guess what this is." Richard took off the bow and ribbon & lifted the lid slowly, peeking at what was inside...and then started giggling.

"Yeah, imagine that! Half the time you can't get basic things like milk and eggs here, but... you can get lingerie." Says the skipper laughing.

"Ahh...what a pretty little maid outfit!" Well, thank you Skip, it looks much nicer than the one I have at home. "Oooh," lifting it up out of the box and holding it up to admire it, "this looks like nice quality too,...for a maid", still giggling.

"Are you ok if we save this for another day? Cause, I just took all my makeup and stuff off and..."

"Oh, for sure, no problem" says the skipper as he gets close behind and wraps his arms around Richard, "you're looking fine just the way you are" his hands groping Richard's breasts under the cropped t shirt and rolling his nipples between his fingers.

Somehow, this felt a bit strange to Richard, as he always felt sexier and femme when he was in full drag. However, he did like the warm feeling of a hug, nipple play and Stan's body rubbing against his behind. Stan kissed him several times on the back of the neck. While their bodies arched forward slightly with Stan's crotch now rubbing into Richard's ass.

"Oooo", giggling again, "that feels nice, but I'm just not sure 'bout how I feel about that, just yet. I'm sorry, you'll have to give me some time to get used to that." Says Richard

Smiling re-assuredly Stan releases his hug slowly and turns him around to see his face, "for sure, babe, no problem. Are we having wine tonight?"

"Yeah I have it chilling. Grab a glass I'll pour" replied Richard.

They sat down at the table and finished a great steak supper and three quarters of the bottle of wine. Just as Richard piled the dishes up on the counter, Stan gets really close again placing his hands on Richard's hips.

"Man, just look at that slim waist and those hips, and that ass just drives me crazy.

Come on baby, it's been a long time coming, and I'm ready for another round", as he pushes his crotch up against Richard's ass and into the counter. Richard could feel Stan's cock was swelling, and after the wine he suddenly felt.. different...about the affection "as Richard."

"Hmm that does feel nice", said Richard, as Stan continued to dirty dance and rub right into the crack of his ass.

Richard turned around to face Stan, reached up and put his forearms around stan's neck. Stan reached around lovingly and put his hands on Richard's ass cheeks and pulled him in for a kiss on the lips.

They held the embrace for a few minutes and could feel the temperatures rise.

"Ok. Ok" said Richard, "but not here. Let's go to the bedroom"

So, they ran down the hall, Richard leading Stan with his hand outstretched behind him, and kicked the bedroom door open. Richard turned around and grabbed Stans t shirt and pulled it over his head. He rubbed his hands on Stans' chest. Then put his own arms up in the air for Stan to pull off his ladies T which was slightly tented with Richard's nipples peeking out.

Stan breathing deeply, wrapped his arms around Richard's waist and grabbed the cheeks of that lovely ass that he just couldn't resist. He pulled up close for a kiss on Richard's neck then, methodically kissed his way down to his erect nipples on his tiny breasts.

Now Richard, began breathing deeply. If there was a thing that really turned up the dials for him it was having his nipples licked and sucked gently. It was electric and usually resulted in almost instant arousal.

This was another first-time event. Heavy petting and arousal without the lingerie. Richard arched his back invitingly to provide Stan with room and free access to continue. Then reached down and cupped each of his breasts for Stan to continue to lick his nipples. Stan placed his hand in the arch of Richard's back for support.

Richard's cock was growing rapidly in his spandex yoga pants. It found the opening between his satin thong and his leg. The tightness revealed the full outline of his erection and a moist patch showed on the outside of the yoga pants.

Stan backed him up closer to the bed and let him fall into it and as Richard's legs rose up, Stan grabbed the yoga pants by the waist and pulled them and his panties off. Richard's cock now finally released from the constraint, bounced straight up. Stan stood there for a few seconds looking down at Richard's slim body while undoing the belt on his jeans, pulling them down to the floor.

He dropped to his knees and grabbed Richard's fully erect cock and without hesitation pulled it into his mouth. Licking and sucking the end of it and going the distance. Engulfing it as far down as he could. Bobbing up and down hard and gasping for breath like he was on a marathon or couldn't decide which he wanted first. He came up for air, breathing deeply and shaking his head.

"I can't believe this is happening, but I just can't resist you. I love your cock, I love your ass! I just want to have sex with you all the time."

Richard's eyes wide open with excitement, was also struggling to believe this was happening, but enjoying it immensely.

Trying to put his thoughts of doubt to the background and wondering why he felt the way he did. Was it that this was taboo? Why did he feel that this sex was taboo, but in drag it wasn't? Was it the risk of getting caught that made it so exciting? Was he actually strongly attracted to male bodies, or was he actually just really attracted to Stan? He wasn't sure, about any of that, but in the heat of passion, there was no stopping any of this right now. And it just felt way too good to stop! And he was definitely up for it right now.

Stan let Richard's cock slide out of his mouth and then crawled up on top of him grinding his cock into Richard's crotch. Their cocks sliding against each other and Stan kissing and teasing his nipples again. Then pulling himself upward further he slid his cock up to Richard's chest. Richard pulled his two arms in towards each other to form what cleavage he had with his breasts. Stan slid his cock up and down within the little titty tunnel Richard had made. With every few thrusts Stan's cock would slide far enough for Richard to get it in his mouth and suck it and lube it up for more titty fucking.

With them both panting like dogs in the desert on a hot day, Stan pulled his legs around the outside of Richard's and flipped him over onto all fours. Stan kneeled up straight and brought his cock in line with Richard's perfect ass. He slid it into the crack of his ass and just rubbed it back and forth a few times sliding on his own precum. He arched his back and tried to penetrate Richard, but his cock just slid through again and topped his ass cheeks. Stan tried again this time holding his cock with one hand and Richard's waist with the other, he lined it up and tried sticking it in, it just wouldn't go in. He tried repeatedly but it just wasn't going in.

"Hold it! Hold it!" Richard said loudly, "I don't think I'm ready for that, and it hurts, badly!"

"Let me try with my fingers" Stan said. Stan moistened his fingers and slowly slipped one in, it seemed to be working and Richard was responding by grinding his butt into Stan's finger, but when he tried with his cock or with two fingers it was just too painful.

Richard said "I'm sorry, it's just not working for me, can you just slide between my cheeks and rub yourself off?" Stan reciprocated without saying anything. He was just so excited and wanted to cum, however it happened.

Richard arched his back to give him the best angle to rub his cock on his ass.

Stan put both hands on Richard's hips and continued pulling Richard's waste into his cock saying, "I'd fuck this ass any which way you want me to. God you got a nice ass!" and with that a few more thrusts sent Stan's cock spewing all over Richard's back.

Richard remained in position while Stan finished. With heavy breathing he reached down and caught Richard's erect cock with his hands covered in cum while it was swaying back and forth. A few minutes of slipping, sliding and jerking had Richard cumming all over the bed spread.

They both fell on their sides, trying to avoid the pool of cum. They just laid there catching their breath for a few minutes.

"Wow" said Stan "that was intense!"

"Yeah" Richard replied, "I'm sorry, I just can't do anal"

"Don't worry about it" said Stan, "it was fucking great!"

They laid there for quite a while. Each in their own deep thoughts trying to rationalize what just happened and trying to decide if they were ok with it or not.

Eventually Stan got up and pulled the bedspread off the bed and hung it in the shower to dry. Then came back to bed and cuddled up to Richard spooning him from behind under the covers. They both fell into a deep sleep.

They slept in the next morning and missed the early bite but got up and went out fishing anyways. They had another great day on the water, coming home with 2 more big chinook and 6 Coho.

When they got back to the trailer and parked the boat, Stan jumped up in the boat and grabbed a small Coho out of the cooler.

"I'm going to give one of these to my neighbour, Holley next door. She'll, likely, really appreciate it."

"Yeah for sure", said Richard. "we got more fish than we need here anyways. I'll get busy with cleaning and washing the fish and get them ready for the freezer."

When Stan came back, they cracked beers, while they tended to the fish, and he explained who Holley was.

"Holley came here to marry Frank, who worked for the company as well. But he was killed a few years ago in an accident."

"Ah Shitty" said Richard.

"Yes, it was, said Stan, "they were only married a year or so when it happened. But the company felt bad for her and brought her in a brand new extra wide mobile and put it on the best lot on the site. And, they even found a job for her here in the office."

"Wow", said Richard, "So she stayed?"

"Yup, I mean, they set her up really well, but she went through a lot. They brought in counsellors and everything for her and for the rest of us in the office. I think she's alright now. She's actually pretty nice lady."

With that, they finished up, had supper and a couple drinks and smokes and watched tv after.

During which Stan got a phone call from his boss. He went into the other room to take the call and then came back to the living room

"Well looks like I gotta go back to work for a few days" said Stan

"The company's starting a new project up island and they want me to look after it. It's not gonna get fully started till next week or the week after, but I'll have to go in for a couple days to catch up and get on board."

"Oh. Ok, uh, should I head back home?" asked Richard

"Well you don't have to. You can stay as long you like, but I'll be here n there for a couple days. You can hang out here if you like. "

With that, they called it a night, and each slept in their own beds. Given the long day they had, they both slept very well.

Lanna as the Maid

The next morning Richard got up and had coffee with Stan before he left for work, and then after he left, went back to bed for a while. He felt he could use an extra bit of sleep, and some time to think about all that had happened.

Later, he got up, had coffee and made a list of things to do. Laundry, clean up, etc. He thought about maybe walking down to the beach for a walk later that afternoon.

Since he was going to be doing housework again, he thought, maybe I'll try on that nice maid outfit Stan picked up yesterday.

He went back to his room to have another look at it in the box. It was made with really nice black sheer material, with white lacy trim and the usual, white satin apron on the front and a few white bows and ribbons. There was boning in the body making it corset style with an attached black sheer skirt, and short sleeves which also had white frilly lace trim.

It came with a pair of matching black sheer, thread style thong panties, and of course the black and white head piece to top it off. "Cute" Richard said, smiling to himself.

Just looking at it and feeling the sheer skirt started his juices flowing. Hmm well I've got all day here by myself he thought. Maybe Lanna could come out for a visit?

"Aaa, I should get something done" he said out loud to himself. "Maybe later, "resisting his urges.

So, he got busy with dirtiest jobs first. Dishes and clean up, piling up the empties in the shed.