The Crossdresser’s Cruise (Closed for Hornyish69)

[PantyMon]

I had lied to my wife about an upcoming “business trip.” I was pretty sure she bought it and instead had planned to go visit her family for the week that I was gone. Luckily, her flight out was the day before mine so after she had left that was when I kicked into high gear.

I had been hiding Amazon packages as soon as they arrived. There was a mountain of Prime boxes stashed in the garage. I brought all these boxes into my bedroom and began opening them like a child on Christmas morning. A black pencil skirt, a short tartan skirt, tank tops, blouses, midi skirts, satin lingerie, nylons, heels, sandals— the works.

About 6 months ago, in a slightly inebriated state late one night I had booked this cruise; the Crossdressers Extravaganza it was billed as. It was for men who enjoy crossdressing but don’t typically have an outlet to express this side of themselves and for any women who enjoyed a crossdresser.

I packed my bag with all my clothes, wig, makeup etc and had one final stop before I headed out on this adventure, i desperately needed a mani and a pedi.

After relaxing at the nail salon, I drove to the airport, cleared customs and had an uneventful flight to Miami where I hailed an Uber direct to the cruise dock. The check in process was simple and soon I found myself alone in my cabin. I unpacked my clothes, hung up what needed hanging and put away everything to make this my home for the next seven days at sea.

Feeling a little shy at first, I did some simple makeup and donned my wig, I put on a cute pair of yellow and white checkered cheeky panties, and a simple white t-shirt bra. I slide into my white leggings, checked my ass to see just how see through they were and I was secretly pleased that you could see the panties I had on. I put on a yellow tank top, and a jean jacket with a pair of white leather sandals.

I wanted to explore the ship, get my bearings of the different decks and find a bar for some fruity over the top cocktail that comes in an unnatural color and usually involves an umbrella.

I sat alone at the edge of the bar, feeling a bit empowered, and was just watching all the comings and goings as the ship prepared for departure:


———-
Hello there.
I’m looking for a fun medium burn, sensual and passionate RP. Where the characters explore themselves and each other. Please feel free to PM me if you want to discuss anything, or feel free to belly up to the bar and introduce yourself.

Hope to hear from you. Cheers

 

[HornyIsh69]

Ish was not a Crossdresser but loved enjoying the part of men dressed like women. Even though he was more into ladies, he did not mind crossdressers. He found them to be cute, and somewhat convincingly sexy. He headed over to the bar to get himself a drink.

Ish Roseblazer was about 5'4, with a broad muscular bodytype and weighed 186 lbs with slight muscles even a visible 6 pack. He was in a sleeveless muscle shirt, khakis and flip flops. He was on a business trip, but this was more of a front to enjoy some crossdressers sucking him off, fucking their tight asses, the works. But right now? He was only here for chitchat as he drank his whiskey the bartender gave him.

 

[PantyMon]

I could feel the glances, the eyes tracing the outline of my body. Secretly it was a little exhilarating and so I shifted my weight on the barstool to provide a few different angles of my curves.

I smiled at you as your nursed your whiskey in that low ball glass at the other end of the bar. I seductively used my tongue to tease the straw in my stupidly fruity cocktail. What the hell was I doing? I thought to myself, but damn it was fun.

It had been a while for me sexually as I found myself in a dead bedroom. Exploring this feminine side was fun, I enjoyed the attention, the flirting, and the glances.

I reached into my purse and pulled out a compact to check my makeup, and I dropped my mirror. I bent down straight legged to pick it up from the floor and I turned in your direction to show off my ass, a little hip sway and the clear outline of my yellow and white checkered cheeky panties were visible under my white leggings.

After collecting my things, I sat back down on my barstool wondering if I took it too far too fast. Mentally questioning my overt behavior which is something I would have never ever done before.

 

[HornyIsh69]

Ish looked at the Crossdresser who was teasing him, growling to himself. "Mmmm... I wonder if she wants a piece of my dick later." He said to himself, noticing how convincingly womanly she looked. It drove him up a wall. Seeing her cheeky panties. The white leggings were hella amazing on her. Seeing her tongue tease the straw as if she was imagining sucking him off.

He chuckles and then watches her going fast but enjoying the show. He walks up to the empty stool next to her.

"Sooo... What brings you on a lovely cruise like this?" He asked her, smiling. Striking a conversation with the crossdresser.

 

[PantyMon]

I take a long sip on my cocktail finishing it. With a finger wave and an eye glance with the bartender he understands I’d like another round.

I turn to face you. Up close I now see just how chiseled you are, even in my fittest of fittest days I never had a six pack like you do. I admire that.

“Hello.” I say in my most feminine voice. “I’m Brooklyn. Well I took this cruise as an escape from my normal life. I’m here to explore all that life has to offer, plus sometimes I just want to feel pretty and sexy.” I say.

The bartender brings me my drink, it interrupts
My train of thought. I thank him.

“So, what about you? What ever gave you the idea that this was a cruise for you?”

 

[HornyIsh69]

"Brooklyn, huh? That's a sexy name." Ish said politely yet lewd. "I'm Ish by the way." He said, slowly extending his hand for a handshake. He noticed the bartender gave him her drink.

"Me? Ah well, I am a man who enjoys seeing some lovely and sexy crossdressing folk who seem really hot." He said, giving Brooklyn some context of why he was here.

He sips his drink, smiling at her. "You enjoying the view here too, huh? What are you looking for on here?"

 

[PantyMon]

“Nice to meet you as well Ish.” I smile as I say that. “So tell me Ish, more about yourself, what kind of activities do you enjoy doing? Have any hobbies? Where are ya from? What do you do for work?” I ask very inquisitively.

I create an intentional pause here and have another sip on my drink.

“As for me? I guess what I’m looking for here, is something I just can’t find in my normal life given circumstances, societal norms, and I’m trying to break free from that if only for this holiday.”

 

[HornyIsh69]

"I'm whether you want to believe it or not, a porn producer. I'm just here to enjoy the sights of the cruise." Ish said to Brooklyn, as she asked him about his hobbies too. "My hobbies and activities are hitting the gym, riding around on my motorcycle, oh yeah, talking to beautiful people like yourself."

He then hears from her about herself taking a break from her normal life. "What about yourself? What's your career, dear?"

 

[PantyMon]

“Well Ish,” normally I’m a corporate whore, I say with a chortle. “I bang on my keyboard for 8 hours a day telling it who’s your daddy and then I go home.

When I’m not working, I try and play outside as often as possible and most of my hobbies are activities that revolve around my that.”

I take another swill from the straw on my drink.

“Ish, it’s been a pleasure meeting you.” I say, but I’m going to retire to my cabin for a bit before dinner.” Not wanting to confess that I’m feeling the effects of my drinks.

 

[HornyIsh69]

Ish smirked while he heard her saying she's gonna retire to her cabin before dinner. "Would you ummmm.... Like to go to dinner with me?" Ish asked her, wondering if she was interested in a little company from the male.

He finishes his whiskey, then returns to his cabin to relax as he smiles. Thinking about Brooklyn herself.

 

[PantyMon]

I smile at you as I stand from my barstool. “Yes, that would be quite lovely.” I respond. “How about I meet you back at this bar at 7 this evening?”

I see you nod in acceptance with a tip of your lowball glass.

“Well then Ish, I’ll see you tonight.”

I turn and walk away as I had back to my cabin.


Once inside, between the booze and the encounter I’m a little turned on. I strip out of my clothing and down to my checkered cheeky panties, and my white bra. I flop onto my bed and began to lightly tease myself. I touch my bra and give the cups a squeeze, I run my fingers all over my body, I trace the outline of my hardening cock on the outside of my panties. I love the supple texture of the fabric and it feels so good. Eventually I begin to stroke myself to a climax where I then drift off to sleep for a mid day nap.

When I awake it’s about 5:30pm and I begin to prepare myself for dinner. I don’t quite think of it as a date, but I’m enjoying the flirting and the attention. I rummage through my closet and find my turquoise blue maxi dress with the long slit up the side to the thighs. I looked at my lingerie, and was really wanting to feel sexy tonight so I decided to wear a satin pink thong with a Lacey back and matching pink satin bra with lace trim details. For shoes I chose a pair of white heels and I was going to wear a pearl necklace.

I got in the shower, and shaved my entire body smooth, and after the shower, I put on my lingerie set. I really loved wearing lingerie and enjoyed just being feee in my cabin in my lingerie. I’d stop every so often and check myself out in front of a mirror, turning and looking at my ass in a lace back thong.

I put on my makeup, not a lot, but just enough. I slipped into my low cut maxi dress. This dress hugged my curves and I could hide nothing. In fact the dress was so tight that I was completely giving off panty lines and you could easily tell not only was I wearing a thong but that it was Lacey in the back. I didn’t care that part made me feel naughty.

Once I was all dressed, wig on, I slid on my white heels and gave a final once over. The pearls hung in the balance of what little cleavage I had. I gave a final twirl for the mirror, grabbed my small clutch purse with my keycard and some lipstick and headed off to the bar.

With each step towards the bar, my hips began to sway and sashay. I was really enjoying the empowering feeling of Brooklyn tonight. When I got to the bar, I was the first one to arrive so I ordered a gin martini with three olives and I sat there enjoying my drink while i waited.

 

[HornyIsh69]

Ish started to look at his watch. He smiled while he took himself a small nap and set his alarm for 6:30 PM so he could prepare for his dinner. It was not a date. Just a friendly dinner with a new friend. Just then, 6:30 PM approached fast. He smiled as he started to shower and clean himself up. He started to get dressed in a suit blazer and pants with a buttoned up shirt.

He headed down the bar, noticing Brooklyn was already there. Ish smiled and says to her. "Is this seat taken?" He asked, noticing how beautiful she was.

 

[PantyMon]

I smiled at you as you ask if the seat was taken. “Yes it is.” I replied and gave a playful long pause….”for you.”

The bartender remembers us from earlier and without hesitation he brings you a whiskey.

“Well, Ish, should we head over to the restaurant? I’m getting a bit hungry.” I ask. I stand off my stool and I stand before you. Your eyes are about direct level with my tits at this point. I catch you staring a little longer than normal so I give a little shoulder shuffle show for you as I watch your eyes eventually look up and lock onto my eyes.

 

[HornyIsh69]

Ish follows Brooklyn to the restaurant. His eyes on her, before then, his eyes were on her tits. Followed by looking into her eyes.

The man had saw her going to a table as he took a chair to move it for her so she can take a seat. "Here you go." He said, being gentlemanly to Brooklyn as he smiles.

He takes a seat at the end of the table. A waitress came over to the both of them and was willing to serve them both for drinks and food.

 

[PantyMon]

I look up at you as your being a gentleman and push my chair in, “thank you ish”

I open my menu and it all looks so good. The steak and lobster, ohhh halibut, I flip through it all and I’m struggling to decide. “Hey Ish,” I ask, “Will you order for me? I just can’t decide and it all looks so good.” I bat my eyes a little bit as I ask.

The waiter returns to our table to take a drink order and I ask for a dry martini with thee olives.

As you order, I think to myself about how I’m here. All dolled up, feeling very pretty in this dress and sexy with the lingerie that I have on underneath.

 

[HornyIsh69]

When Ish notices Brooklyn ordering a dry martini with three olives, he gets a thought that brought him back to those women posing and modeling. Showing their sexy bodies through a martini glass for the magazine ads. Brooklyn, looks really dolled up and reminds Ish of the vodka ad models. "You want me to order for you? Alright. Don't get mad if I order you the same thing I order." He chuckles.

He smiled and then asked for a drink order of a glass of Merlot wine. "I will have the steak and shrimp plate. Make that 2. With asparagus and fries for the sides. The steaks medium rare, please. It's for me and the Madame here." Ish said, smiling.

The perky waitress looks at them both, writes the order down. "I will get those put in. Please enjoy yourselves."

 

[PantyMon]

“Sounds lovely, thanks Ish.” I take a sip of my martini and lock eyes on you. I shyly smile at you. As I set my drink down on the table, I ask you, “so Ish, have you ever …. Um…..” I start to blush a little as I’m not usually this forward a person, “well been with a woman like myself?” Those last words just kind of popped out of my mouth in a low whisper. As k scan the room before I said it. Only to realize that there was a lot of women like me in this restaurant at this moment. Which is where I must have found the strength to ask the question.

 

[HornyIsh69]

Ish smirked as he heard her asking the question. "Why, yes. Yes I have." Ish said to Brooklyn. He starts to point out one of the Crossdressers he had fun with the last time he was on this cruise and yesterday. "Her. That is Erica Marie. She was a fun one. Blonde, sexy and can take it like a woman." He said to her, sipping his wine.

He looks at Brooklyn, then asks her. "Why? You wanna spend some time with me and see where it takes us?" He was actually serious about that, but can tell that Brooklyn had a look on her face when Ish proposed the question to her.

 

[PantyMon]

As you asked the question, I just wasn’t sure exactly how far I wanted this to go. I was enjoying the banter, being a bit of a flirt with you, but I was scared of just being used like a piece of fuck meat, when really I was craving sensual attention. I longed to be treated like a woman, I wanted to made love too. Yes, I also desired to be a submissive good girl too.

All these thoughts went through my head as I heard
You propose your question. Hence why my face registered shyness, a little confusion I was nervous as I had never done this before. Sure I’ve played with plugs and massagers so I wasn’t necessarily worried about the mechanics of it all. Did I really want to cross this line?

I took a long sip from my martini.

“Ish, I’m not just a slut here to be used and tossed aside” I said in a somewhat demanding voice. “I don’t want to be treated like a porn star in one of your movies. “

 

[HornyIsh69]

"No, nonono. That's not was offering. I was actually looking for a sensual attraction from you." He said, silent since the crossdresser that he pointed at wasn't in the mood for the sensual attraction from him. Perhaps it was different with Brooklyn, perhaps a little more. "Sorry if I was saying that I was only looking at you as a notch on my belt."

He said to Brooklyn, hoping she got the next part. "Besides, I believe in being a gentleman in the streets, and behind closed doors too." He said, saving the banter and warranted company.

 

[PantyMon]

My eyes lit up, I smiled. “Well Ish, you certainly are a gentleman.”

Our steaks, shrimp and bottle of Merlot arrived. “Oh this smells delicious and looks amazing.” I exclaim. It was then that I had secretly decided to go all the way with you. I take a bite of my meal, we enjoy casual dinner conversations as we get to know each other better.

As the meal concludes, and we just have our wine to finish. “Well, what should we do next? We could walk the ship’s deck and take in the salty air, or perhaps we go to one of the clubs and go dancing? Really I’m open for anything.

 

[HornyIsh69]

"Walk, and then hit up one of the clubs." Ish suggested since he needed a breath of fresh air. Even with a beauty like Brooklyn. He smiled as he led her the way. Walking around the ship's deck with the beauty.

A few minutes of walking, Ish lead the way again for Brooklyn to head to the first club which was actually in their path of the ship's deck. Smiling at Brooklyn. "I'm a good dancer, so I'm warning ya." He said, chuckling.

 

[PantyMon]

As the salty fresh air hit my ol factory bulbs it just brought a smile to my face. Walking the deck was nice. As we walked and talked I put my arm around yours. I was beginning to feel quite comfortable with you and your company.

The lights and sounds of the club were popping off as we approached. “I’m looking forward to seeing your dance moves.” I said with a smirk as I wasn’t sure if I should believe you, but there was only one way to find out. I grabbed your hand and pulled us straight to the center of the dance floor. We almost immediately found the beat and had our own rhythm soon it seemed we were just in our own little world completely oblivious to any one else in the club. I rested my hands up on yours shoulders as you grabbed my hips and twirled me around.

 

[HornyIsh69]

Just then, an erotic throbbing beat song came on. Ish danced around Brooklyn. "Follow my lead." He said to her, teaching her how to dance erotically while still being a gentleman or a lady in her case. His eyes kept on her.

He grabbed her hips, twirling her around. He slowly moves up close to her.

 

[PantyMon]

As you move closer, I can smell your cologne and I feel a little stirring in my panties. Not growing or anything embarrassing like that. Secretly I’m enjoying your hands on my hips as we move about the dance floor. I move my hands from your shoulder and put my arms around you resting in the small of your back swaying to the music.

my whole life I’ve always been the other person, the guy taking the lead on the dance floor, ordering the dinner, pulling the chair out for my wife. This though was nice for a change, I was finding deep satisfaction in this exploration of a feminine side of self.

I wanted you to slide your hands down and cup my ass as we danced. I wasn’t going to tell you this, I was being a lady after all.

Instead I just looked into your eyes and gazed as we danced.