Deckhand Adventures 02 - Alexa

*This story is a continuation of Deckhand Adventures 01. Enjoy...

xxx Halloween night xxx

Not saying that it was a bad party, I was just done with my night. Finding myself sipping on a cold beer by the window, I felt like part of the background.

I was so nervous and very excited leading up to this night and in the end, I'm about to leave this Halloween house party uneventfully and unnoticed. I turned to look out the window, guiding some stray hairs behind an ear before reaching for the remains of my drink.

"Pretty chill party, hey?" he asked suddenly and cheerfully.

I almost spat out my beer due to the surprise. I hadn't even noticed James approach. How do I respond? What do I do? I guess my confused expression was enough of a response.

"I was expecting it to be livelier," he added, jokingly dancing a little shuffle.

I giggled quietly and finished the rest of my beer. "Would you care for another? Maybe a drinking partner?" James put his hand out, suggesting he'd take my empty bottle. This was going interestingly. I had hardly said a word yet... I nodded and smiled shyly, following him to the kitchen island for the ice bucket filled with beer.

He grabbed a couple, and, after opening them, handed me one and raised his bottle before taking a sip. I must have blushed and quickly took a gulp of cold beer to cool myself off.

This was it. Let me try something out. I'm tired of being here at this party and wanted to go for a walk down the beach before heading home. He shrugged awkwardly with a smile, I laughed, and started making my way to the door.

I looked back at him suggestingly, wondering if he was going to take the hint and follow me, "So are you coming?" He looked around pretending that there were so many other people, as if I were asking someone else. It was clownish, but the effort was admirable. It made me feel pretty good.

He caught up to me, beer in hand, as I lead the way down the front steps and out into the night.

××× 9 months earlier, February xxx

I squirmed in my seat, shifting left and right to try and ease some pressure, but it was no use. I tried to keep a straight face looking out the windows, the rhythmic pounding of the waves on the boat made my little jeweled plug vibrate just the right amount to have me flustered.

My own little challenge/punishment to myself. I knew that when I got horny, I could get pretty slutty. So I thought I'd put it to the test by trying to keep myself plugged for my afternoon shift on the boat. It had been 3 days prior to this of teasing and edging myself, being careful not to push too far.

This time, I was hardly able to make it through the day. I did my final checks, packed up, and made my way home. It's a 20-minute walk with stairs and some small trails. Perfect. On the walk, I became very aware of the swing of my hips and bounce of my cheeks. It made for a very hot walk home.

By the time I was there, I was practically out of breath. I quickly undressed and got in the shower as soon as I dropped off my backpack at the door. With my naked freedom and welcome warmth of the shower, I slowly eased the plug out of me, shivering as it popped past the widest point.

That evening ended like many before it - with me thinking of what I had done with a certain degree of shame and a greater one of curiosity while washing 2 dildos and a buttplug in the sink. I was exhausted and so satisfied, I didn't dwell on it too much, though. After a little snack and a joint, I was sound asleep and comfortable in bed.

Were they some ex-girlfriend's I had found in my room? Or had I worn my roommate's when she dropped one coming back from laundry? Black lace? The snapping of stay-ups on the thighs.

I awoke suddenly in a sweat. My mouth was so dry I could hardly swallow. I sat up to drink some water. I was too tired to remember what woke me. I figured I don't dream anyway because of the weed so it was either my cat or plainly, my thirst. I tucked myself in once more and quickly fell asleep.

The next couple of days were uneventful at work. It was nice being on the water. The current Master, Caroline, on deck was pretty knowledgeable about the wildlife in the area. She had given her 2-week notice and was happy to be spending more time at home in the coming months. I was just looking forward to my weekend...

On the last day of work that week, I was particularly horny. Having been satiated on my last weekend, I refrained from any sexy self-pleasuring and my aching balls were protesting the build up. As we made good speed across to one of the farther stops, I started to feel the vibrations of boat and waves. What began as a tingle which worked its way from the inside of my thighs to my groin and up to my belly, ended in my need conceal my growing boner by crossing my legs and trying to engage in small talk.

"So what are you most looking forward to this weekend now that it's your last day?" I asked.

"Being in bed and cuddling my cat," replied Caroline.

"That's the best way to spend time off!"

"Totally! With ice cream breaks," she added.

I laughed. "Do you know who I'll be working with next week?" I wondered.

"Oh. Possibly James. You haven't met him yet. He was somewhere in Africa visiting family," she replied cheerfully.

I pondered this for a second and caught myself in a daydream when Caroline continued, "What about you? Any plans?"

I stuttered, "Huh? Umm... No, not really"

At that point the conversation fizzled away as we arrived to our destination and I helped load up the last customers for the day. Sitting down in the vibrating cabin, I did all I could to keep my mind distracted from fantasizing.

Once we arrived to our home dock, I did my final checks after helping everyone off and wishing them a great weekend. I bade farewell to Caroline and wished her luck on her cat cuddling good time.

As I walked home, it started to rain lightly. By the time I got to my place, it was coming down heavily. I knew the weekend would be a cozy one. I crashed shortly after dinner and a shower.

Muffled moan. Quiet and rhythmic smacking sounds. The slip of oiled skin. Or was it sweat? Drooling. Veiny. Tasty. The occasional gag and ecstatic gasp for air. A slurp and a moan. Hard and throbbing. It's really warm.

I woke up sweating with a raging hard-on. Sleeping in boxers, it was poking through the front, the soft sheets gently caressing the head. I shifted to my other side, adjusting my boxers to their proper place in the process. I'm asleep before I have any time to wonder.

I woke up beautifully refreshed and quite early. After getting cleaned up, it was time to start my day. I lubricated and inserted my favorite jeweled butt plug. Found a pair of panties at the bottom of my sock drawer and put them on. Black lace thong. I dug out some thigh high stockings (also black lace), and rolled them up my legs carefully, snapping them in place. Just then I had an odd sense of déja-vu.

I shook my head then reached for my sweatpants, shirt, and hoodie. Walking to the living room, I could feel the heavy metal plug shaking with every step. It caused me to sway my hips as I walked. Tucked in nicely in my thong, I was able to restrain my arousal and instead felt every dribble of pre-cum dampen my panties whenever I sat down or shifted.

Part of the fun for me is the tease and denial, so I sat to roll myself a joint. I try to behave totally normally and keep a poker face as I step outside to have a smoke on my patio. After about 15 minutes, having the butt plug in felt less like an intrusion and more like an accessory. Time for housework.

First things first : kitchen. It's usually such a boring chore to do the dishes and put everything away (even though I have a dishwasher). With my secret under my regular home clothes, it made bending over to reach the bottom rack in the dishwasher a lot more fun. I purposely exaggerated my movements.

Next came the bed. Again, every movement was accentuated and in doing so, I was further stimulated. Only bad girls misbehave, I caught myself thinking. Shush. Get back to work.

My morning continued as such until I was satisfied with my work. Time for another joint as a reward.

Clenching, I could feel myself pucker around the plug. I found myself rocking slightly while I sat, withholding muffled moans in between puffs. I was reaching a tipping point and had to do something about it.

My playdate with myself was set. Bedroom door locked. Towel and oil nearby. My bag of toys emptied with its contents scattered near the towel.

I suctioned my 7" dildo onto the back of my door. Shedding my boy clothes, I knelt down facing it and closed my eyes. I grazed it lightly with my fingertips, imagining the shudder initial contact would give. I hungrily let my tongue fall and leaned in closer.

I could feel it close, though it would be warmer if it were James'. My cock twitched and throbbed at the thought...I haven't even met him yet. I almost drooled. I began to kiss and lick up the sides of my toy, letting myself fall into the fantasy. I gave the balls their fair share of attention, like a good girl. I felt my buttplug grind on a sensitive spot and new dampness forming in my panties.

I was entranced by this fantasy, letting myself go and sucking on that fake cock like I wished I could a real one. I wonder how much of James' I could get in my mouth. I pulled away from my teasing, took a breath, and slowly eased the head in past my lips.

I started bobbing and moving with the length of it. Swirling and flicking my tongue over the textured veins, imagining how it might feel for the cock and the person it belonged to.

Some time had passed when a gag snapped me out of a trance. I opened my eyes to realize my nose was almost touching the door. I moved back, letting the dildo slide out of my throat and mouth, to swallow and gasp for air. This felt oddly familiar and I thought I remembered parts of a dream. Nevermind. Keep sucking.

I worked up to impaling myself on my dildo. Every time I got it balls deep, I would feel my hole tighten around the buttplug. This was reaching another level. Time to step it up.

I went to my bed for my other dildo. This one was thicker. One I couldn't even suck on - I had tried. It replaced the one I had been using so far on the door. I moved my thong aside to pull out my plug. I gave it a light tug and it slowly started to ease out. Once past the widest point, it easily slid out as I moaned.

By now I was sweating and just needed to take my panties off. I also rolled off my thigh highs and stood with my back to the door. With a bit of oil on my hand, I lubed my big toy and myself.

Whatever happened next could only be described as blissful. Standing up and slowly welcoming that thick cock in felt like, I imagined, I was being penetrated somewhere I shouldn't be (perhaps a storage room, changing room showers, or maybe the boat I worked on). As I eased myself onto that dildo, a continuous dribble of pre-cum leaked out that I tried to keep from falling to the ground. I licked up whatever landed on my fingers while arching my back, taking it deeper.

When my cheeks felt the cold door, I paused to revel in how horny I was and how amazing it felt. I was being stretched out, balls deep, by a dildo I could hardly fit it my mouth and it felt so good. I gently rocked my hips back and forth.

In no time I had worked up a smooth rhythm of riding it. I bucked my hips back, shaking the door as I bottomed out. Soon the smooth movements were replaced by roughness; an easy back and forth became quick and deliberate backward slams.

My knees were shaking now and in between sounds of wetness and the door shaking on its hinges were my own moans of pleasure. I want to be taken like this... I pulled on the base of the dildo, releasing the suction from the door and fell forward with it still inside me. I landed on my knees and moved back to secure it lower on the door.

On all fours, I continued to ride, drool, and drip pre-cum until again, my knees were getting sore. I pulled myself off and moved the dildo to the floor.

Laying on my back, I raised my hips to line it up and guided it back inside me. The change of angle was perfect. As I rode the dildo faster and harder, my own cock flopped, helplessly dripping and smacking against my lower belly.

After an unknown amount of blissful ecstacy, I felt myself reaching climax. I continued to drill myself by raising my hips up until the toy had almost slipped out and falling back down onto it - the squish of wet sounds coming from under me as my bum hit the floor.

Without once touching myself, a small squirt of cum oozed out onto my leg. Then, as I slowed down, one more larger one made a streak across my belly. A third shot up and hit my chest. I was moaning and panting frantically. Trying to continue riding through my orgasm was difficult.

My muscles were spasming and I was slipping on the floor from sweat and oil but I continued making an effort to prolong the pounding. I managed to cum another two times before surrendering to gravity and exhaustion. With the dildo still lodged balls deep in me, my insides clenching and squeezing around it, I panted for air.

As I lay there recovering, more cum leaked from me. I lost count and lost track of time and of where fantasy and reality separated. It felt good, though. With some effort, I moved to let my dildo out of me. It squelched to my side and I lay there, spread eagle on the floor catching my breath.

I woke up about 20 minutes later. It smelled like sweat and cum everywhere. I traced a finger across my abs and felt the stickiness of it, bringing some to my lips for a taste. I wished I could've swallowed...

Later, in the shower, while cleaning myself and my toys, I was feeling really good. I felt satisfied and happy. It was so nice to let go and to allow that slutty side of me to escape. While the steam cleared after my shower, I caught my reflection. My face was flushed and my cheeks were rosy. I blushed further, smiled, and turned to get dressed ('normally') again.

The rest of my weekend was filled with relaxation. I enjoyed some good meals, I slept in, I read and watched a movie. It was great to be in my own company. It wasn't until the night before my first day of work that week that I remembered that I'd be working with James. I caught myself licking my lips. I don't even know him! Naughty girl.

xxx

I usually show up to the boat early so that I can do my checks and this started like any other beautiful morning. It was early March and before 7 am, the sun hasn't even peeked over the mountains.

As I was nearing the end of my last voicemail on the request line, I felt the boat rock with the telltale sign that somebody had come aboard. When I looked up, I was greeted by a bright confident smile. He introduced himself as James, who had just come back from Kenya. After some smalltalk getting to know each other, we were underway with a few passengers.

xxx 3 days before Halloween xxx

It was consistently cold now. Days and nights alike were spent bundled up in layers. This was a good time to try it out. 'I mean, why not?' I had thought when I made my online order. There is really no argument against that. I had been wearing panties secretly for a while. Maybe this time, I had the occasion (or excuse) to spill the proverbial beans.

3 days before Halloween, I recieved my package, not unlike the several I've gotten delivered these past couple of months. I opened the box and laid the contents out on my bed. I got a little aroused. This would not do! I couldn't go around getting hard if I was going to wear this to the party. I was convinced I needed to practice.

I was in no condition to try on my new costume. I had to prepare myself and get a practice run (at least to perfect the look). I went to the bathroom with my basket of goods, leaving the costume on my bed.

I always liked to have my bikini area smooth. This time, it warranted for more. I used my trimmer first to get my legs, belly, chest, and arms. I even shaved my beard clean off. Next, I repeated the same with a healthy amount of cream and a razor.

After an attentive shower, I stepped out into a steamy bathroom, freshly shaven leg leading the way. I followed by slowly and carefully oiling myself. Of course, my large metal butt plug was inserted before I went to choose which panties to wear.

For today, it'll be the simple black briefs. My cock twitched as I pulled up my black stay-ups - how they glid over my smooth and moisturized legs. I opened the door to the washroom and strode to my room, happily knowing I'd be home alone until around 5.

I stepped into the red plaid skirt, pulled it up to my waist and zipped it up. Straightening out the pleats, I was happy with the just-above-the-knee length. I could sense the skirt's movements across the top of my stockings.

I put on the blouse, tying off the bottom and slightly revealing midriff. It didn't really matter, though, because I'm sure I would be in my sweater the whole time anyway. Before trying that on, I paused to check myself out in the mirror.

I was feeling a lot of things at once: Amazement at how surprisingly good the costume was on me; shock that I am actually taking it this far; the plug blissfully penetrating me and stimulating as I move; determination to finish with make-up and hair.

I had amassed a meager few pieces of make-up over a few months. Firstly, I needed to conceal where the beard once was. Next came eyeliner, mascara and a wine-red lipstick - simple. Done.

I split my shoulder length hair down the middle and made up a loose braid on each side, finishing them each with a small white ribbon.

As I stepped back from the mirror and my focus changed from close-up to full view, my cock, constricted in the tiny briefs, throbbed and spilled a load of pre-cum. I felt the sticky wetness spread as the panties soaked some up.

Finally, I slipped the black rounded-toe wedges on, buckling them around each ankle. Before standing up, I clipped on the small choker necklace, centering the metal heart. With the heels on now, all the angles change, and it was more difficult to stand. New sensations quivered through me as my butt plug shifted.

Every step with the heels drove the plug sideways as my hips swayed, pushing on my p-spot. I walked a few circles in my room until I was used to the balance and my dick wasn't protesting in arousal. I need to have a smoke. It'll help to pass some time and ease all this excitement.

I walked down the hall towards the coat closet, feeling more stable and confident in my strides. As I was struggling to get one arm into my coat, I heard the front door unbolt and open. I froze, dropping the coat to the floor as my roommate, Katie, came in suddenly and sighed, finally sheltered from the rain.

She was having a hard time taking her boots off and keeping her purse from falling that she hadn't even looked up yet. I did not know what to to, so I just stood there dumbfounded. When she finally freed herself of her rain gear, she looked up and noticed me. She let out an almost inaudible gasp with her double-take.

Silently, she approached me, keeping intense eye contact. Katie came so close, I could smell her perfume. She traced me down my profile with her gaze, stopping as something caught her focus on my skirt. As she straightened out a pleat with one hand, she grasped a label I had forgotten to take off. With a sudden and swift tug, she removed the label.

This whole time I was frozen in place. I could hardly breathe. She was so close and had not yet said a word. I could feel myself starting to sweat when I felt Katie grab the edge of my skirt. As she tugged, the smallest mumble of a moan escaped my lips. Katie's gaze returned to mine, biting her lip slightly as she raised up her hand from my skirt, a size tag and label hanging between her fingers.